Today let’s debunk a few commons myths and false beliefs using a good dose of surprising evidence. Here are the top ones we explored so far in the newsletters. if you enjoy, go read the entire list of 150+ insights for free.

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Solo founders last longer and earn more, despite investor bias toward teams

Despite investor bias toward teams, solo-founded companies lasted longer and achieved higher revenue than those with multiple co-founders (study of 3,526 startups). The researchers attribute this partly to decision-making agility and absence of co-founder conflict. Separately, 65% of startup failures involve co-founder conflict.

Source: Greenberg, J. & Mollick, E. “Sole Survivors: Solo Ventures vs. Founding Teams.” Working paper, Wharton/NYU.

Only 16% of burnout patients considered themselves fully recovered after seven years

A seven-year longitudinal follow-up found that only 16% of burnout patients considered themselves fully recovered. The brain and nervous system take longer to heal than the calendar suggests. Prevention may be the only reliable cure. Most founders think burnout is a bad week - it is a years-long injury with an 84% incomplete recovery rate.

Source: Glise, K. et al. Seven-year follow-up of patients with exhaustion disorder. Cited in: Almén, N. (2021). “A Cognitive Behavioral Model Proposing That Clinical Burnout May Maintain Itself.” International Journal of Environmental Research and Public Health.

The average founder of the fastest-growing startups is 45, not 25

Analysis of 2.7 million startup founders using US Census and IRS data found the mean founder age at founding is 41.9 years. Among the top 0.1% fastest-growing firms, the average founder age was 45.0. A 50-year-old founder has 1.8 times the odds of achieving a 1-in-1,000 growth outcome compared to a 30-year-old.

Source: Azoulay, P., Jones, B.F., Kim, J.D. & Miranda, J. (2020). “Age and High-Growth Entrepreneurship.” American Economic Review: Insights, 2(1), 65–82.

VCs ask male founders promotion questions and female founders prevention questions, costing women $3.8M per question

Analysis of 189 Q&A interactions at TechCrunch Disrupt found 67% of questions to male founders were promotion-oriented (”How will you acquire customers?”) while 66% of questions to female founders were prevention-oriented (”How will you not lose customers?”). Each prevention question was associated with $3.8 million less funding raised.

Source: Kanze, D., Huang, L., Conley, M.A. & Higgins, E.T. (2018). “We Ask Men to Win and Women Not to Lose.” Academy of Management Journal, 61(2), 586–614.

Expanding choice from 6 to 24 options made people 10x less likely to buy

The “jam study” — participants exposed to 6 options were 10x more likely to purchase than those exposed to 24 options. Choice overload reduces engagement and decision quality. Simplification is a conversion strategy. Every founder building a product with too many features needs to hear this.

Source: Iyengar, S.S. & Lepper, M.R. (2000). “When Choice Is Demotivating.” Journal of Personality and Social Psychology, 79(6), 995–1006.

The least competent founders are the most confident — and cannot see it

People with limited competence systematically overestimate their performance because the skills enabling accurate self-assessment are the same skills their performance requires. Top performers tend to slightly underestimate their competence.

Source: Kruger, J. & Dunning, D. (1999). “Unskilled and Unaware of It.” Journal of Personality and Social Psychology, 77(6), 1121–1134.

Each unit increase in entrepreneurial orientation raises firm failure risk by ~25%

Each incremental unit increase in risk-taking, innovativeness, and proactiveness raised firm failure probability by nearly 25%. The same traits that make founders exceptional also make their companies fragile — unless deliberately counterbalanced.

Source: Entrepreneurship Theory and Practice (2023). The dark side of entrepreneurial orientation.

Sleep problems increase entrepreneurial motivation but undermine the cognitive abilities needed to succeed

Research revealed a paradox: sleep problems may actually increase entrepreneurial motives (through restlessness and dissatisfaction with employment) while simultaneously undermining the cognitive abilities critical for venture success — alertness, creativity, and social competence. This “sleep trap” means the conditions that push people toward entrepreneurship also make them less equipped to succeed at it.

Source: Murnieks, C.Y. (2020). “The Sleep Trap.” Academy of Management Perspectives, 34(1), 42–62.

Entrepreneurship can become an addiction with clinical features resembling substance dependence

Research defined entrepreneurship addiction as excessive or compulsive engagement in entrepreneurial activities despite negative social, emotional, and physiological consequences. Multi-item scales validated six criteria: obsessive thoughts, withdrawal symptoms, self-worth contingency, tolerance (needing more), neglect of other life domains, and negative outcomes.

Source: Spivack, A.J. & McKelvie, A. (2021). “Measuring Addiction to Entrepreneurship.” Journal of Business Venturing Insights, 15, e00212.

29% of entrepreneurs have ADHD, 6x more than the general population

Entrepreneurs reported significantly more ADHD (29%), depression (30%), and bipolar disorder (11%).

Source: Doyle, N. (2020). “Neurodiversity at Work.” British Medical Bulletin, 135(1), 108–125. Also: Freeman, M.A. et al. (2018). Small Business Economics, 52(2), 323–335.

Narcissistic founders set lower goals and longer timelines to protect ego

Narcissism doesn’t make you aim higher — it makes you aim lower to avoid being seen failing. Research on crowdfunding entrepreneurs found that more narcissistic founders set lower goals and longer timelines — suggesting narcissism protects the ego from the threat of visible failure more than it drives ambitious action.

Source: Small Business Economics (2019). Narcissism and crowdfunding goal-setting.

Intrinsic motivation trap: 55% of managers pile extra work on their most motivated employees

55% of managers systematically assigned extra work to their most motivated employees — not out of malice, but because motivation signals capacity. High intrinsic motivation can be both a burnout shield and a burnout risk.

Source: Organization Science (2023). Overloading the willing: motivation as a workload signal.

Moderate procrastination is more creative than none at all

Procrastination has an inverted-U-shaped relationship with creativity. Moderate procrastinators generated more creative ideas than both low procrastinators (who started immediately) and high procrastinators (who delayed excessively). The mechanism: moderate delay allows incubation and problem restructuring without losing engagement entirely.

Source: Shin, J. & Grant, A.M. (2021). “When Putting Work Off Pays Off.” Academy of Management Journal, 64(3), 772–798.

The brain processes beauty and financial value in the same neural circuits

Neuroimaging studies consistently show that aesthetic experience activates the orbitofrontal cortex and ventromedial prefrontal cortex — the same regions involved in reward valuation and economic decision-making. Beauty is unconsciously processed as a form of value.

Source: Brown, S. et al. (2011). “Naturalizing Aesthetics: Brain Areas for Aesthetic Appraisal Across Sensory Modalities.” NeuroImage, 58(1), 250–258.

Serial entrepreneurs who switch industries after failure perform worse because they blame the wrong thing

Founders whose previous venture failed are likely to attribute failure to external causes and change industries. This industry change produced 23–31% slower growth in Chinese data and 18% lower chance of a value-creating exit in US data — because it invalidates the industry-specific experience that was actually valuable. The instinct after failure to try something completely different might be wrong.

Source: Eggers, J.P. & Song, L. (2015). “Dealing with Failure.” Academy of Management Journal, 58(6), 1785–1803.

Work-family conflict in self-employed couples crosses over — one partner’s stress directly harms the other

The crossover effect: one partner’s perception of work-family conflict undermines the well-being of both partners. Work-family enhancement improved well-being primarily for the self-employed partner but did not cross over to benefit the spouse. The costs of entrepreneurship are shared but the psychological benefits are not.

Source: Alshibani, S.M., Olaru, D. & Volery, T. (2024). “The Influence of Work-Family Conflict.” Work, Employment and Society, 38(4), 1128–1147.

People overestimate how crushed they will feel by failure and how good success feels

People systematically overestimate the intensity and duration of their emotional reactions to future events. This “impact bias” leads to flawed decisions. People underestimate their psychological immune system’s ability to recover from setbacks and overestimate how long success will make them happy.

Source: Wilson, T.D. & Gilbert, D.T. (2005). “Affective Forecasting.” Current Directions in Psychological Science, 14(3), 131–134.

A 12-minute guided daily meditation improves entrepreneurial self-efficacy (large effect), creativity (medium), and alertness (small)

A pre-post experiment with nascent entrepreneurs found that a single 12-minute guided meditation session produced significant improvements: a large effect on self-efficacy (d = 0.93), a medium effect on creativity (d = 0.79), and a small effect on alertness (d = 0.44).

Source: Moder, S., Jehle, E., Furtner, M. & Kraus, S. (2023). “Short-Term Mindfulness Meditation Training.” Journal of Business Venturing Insights, 19, e00381.

Four distinct coping profiles exist among entrepreneurs — “Spock Strategists” report the highest well-being

Latent Profile Analysis identified four profiles: Emotional Rollercoasters (27%), Zen Minimalists (39%), Integrated Problem Solvers (16%), and Spock Strategists (19%, high problem-focused, low emotion-focused). Spock Strategists reported the highest well-being across all measures.

Source: Williamson, A.J. et al. (2024). “From Emotional Rollercoasters to Spock Strategists.” Journal of Business and Psychology.

Founders will voluntarily discount the sale price of their company to ensure it goes to the “right” successor

Research on 42 owner-managers found that emotional pricing — price elements driven by non-economic considerations — leads founders to accept below-market valuations to place the firm with a successor they trust. Longer-tenured and higher-performing founders showed greater willingness to sacrifice economic value for perceived “fit.”

Source: Kammerlander, N. (2016). “’I Want This Firm to Be in Good Hands’: Emotional Pricing of Resigning Entrepreneurs.” International Small Business Journal, 34(2), 189–214.

The brain treats aesthetic violations as a form of contamination threat

Aesthetic responses to bad design or ugliness activate the insula — the brain region associated with disgust, contamination detection, and visceral rejection. The brain treats aesthetic violations as a form of environmental threat, not just a neutral preference. Good UX instills a deeply pleasing emotion, and bad UX triggers a deep repulsion. Bad design is the same as rotten food.

Source: Emotion Review (2013). Aesthetic disgust and insula activation.

Founders who anticipate business failure before it happens recover emotionally faster afterward

Research introduced the concept of anticipatory grief as a mechanism for reducing post-failure emotional devastation. Entrepreneurs who psychologically prepared for potential failure experienced lower grief intensity when failure actually occurred. This enabled faster emotional recovery and quicker re-engagement with productive activities, including subsequent ventures.

Source: Shepherd, D.A., Wiklund, J. & Haynie, J.M. (2009). “Moving Forward: Balancing the Financial and Emotional Costs of Business Failure.” Journal of Business Venturing, 24(2), 134–148.

Serial entrepreneurs do not reduce their overconfidence after failure — they maintain comparative optimism

Typical entrepreneurs are somewhat less likely to report comparative optimism following business failure, but serial entrepreneurs who have experienced failure do not appear to adjust their comparative optimism at all. This suggests that the much-celebrated “learning from failure” narrative may be overstated — at least regarding calibration of confidence.

Source: Ucbasaran, D., Westhead, P., Wright, M. & Flores, M. (2010). “The Nature of Entrepreneurial Experience, Business Failure and Comparative Optimism.” Journal of Business Venturing, 25(6), 541–555.

Depression among entrepreneurs predicts venture exit independent of business performance

Analysis of large-scale survey data showed that entrepreneurs experiencing depression were significantly more likely to exit their ventures, even after controlling for firm performance. Depression impairs the cognitive and motivational resources needed to manage a business, creating a vicious cycle: entrepreneurial stressors trigger depression, which impairs performance, which deepens depression and precipitates exit.

Source: Hessels, J., Rietveld, C.A., Thurik, R. & Van der Zwan, P. (2018). “Depression and Entrepreneurial Exit.” Academy of Management Perspectives, 32(3), 323–339.

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Anyone aiming to achieve peak long-term performance is eventually going to push hard against their own mental and physical limits. The question becomes: what will you do then?

The same fire that gets you to break doors open can also burn you to the ground. But that fire can also be rekindled—powering you forward to rebuild yourself post-burnout. Not back to the way things were before, but toward a new trajectory powered by genuine energy and curiosity.

The Biology of Breaking

Burnout is recognized as an “occupational phenomenon” resulting from long-term, unmanaged workplace stress. It involves three core dimensions: exhaustion (feeling drained), depersonalization (cynicism and mental distance from work), and reduced efficacy (feeling incompetent or unproductive).

While not a medical condition, burnout causes measurable neurological changes. Your prefrontal cortex—the region responsible for executive function—physically thins. Your amygdala, the brain’s alarm system, grows larger and becomes hyperconnected to stress regions. Your dopamine system becomes blunted, which is why activities that once brought joy no longer trigger the same response.

The research offers some hope: brain biomarkers elevated during burnout normalize at long-term follow-up. The brain can heal. But notice the timeframe. Not months. Years.

A study tracking burnout patients for seven years found that only 16% considered themselves fully recovered. 73% reported permanently reduced tolerance for stress. One-third were still clinically diagnosed with exhaustion disorder at the seven-year mark.

The brain changes. The brain heals. But the timeline is longer than we imagine.

The Myth of Rest

A dangerous myth about burnout: that a vacation can cure it. It can’t.

Organizational psychologist Nick Petrie’s research is clear—rest isn’t the long-term solution. Yes, rest matters, but it’s not sufficient. Simply stopping doesn’t undo what years of overextension created.

Here’s the paradox: mastery experiences—learning a new skill, creating something, pursuing a challenging hobby—are more restorative than passive rest. Activities that generate new skills replenish depleted resources in ways that lying on a beach cannot.

Researchers distinguish between hedonic wellbeing (pleasure, comfort) and eudaimonic wellbeing—the deeper satisfaction that comes from meaning, purpose, and personal growth. Pleasure alone doesn’t restore you. Meaning does something that rest cannot.

The recovery paradox: doing nothing doesn’t restore you. Doing different things—things that create meaning and build mastery—does.

Burnout Is an Identity Crisis

Recovering from burnout requires relinquishing an identity built on survival energy: the performer, the pleaser, the strong one, the achiever at all costs. Burnout destroys that primal identity. That’s why it feels like death—because in a way, it is.

The research on meaning reconstruction—originally developed for bereavement—applies directly here. Burnout “shatters pre-existing assumptions key to the individual’s self-narrative.” Recovery requires constructing a sense of self that accommodates the reality of what happened, rather than trying to return to who you were.

Theodore Roosevelt understood this after his devastating 1912 defeat. Friends who had competed for his attention now shunned him. He suffered what he called a “bruised spirit.”

His response wasn’t rest. At age 54, he chose to explore the unmapped River of Doubt in the Amazon—an expedition so dangerous that one expedition member wrote, “I don’t believe he can live through the night.”

Roosevelt’s philosophy: “Black care rarely sits behind a rider whose pace is fast enough.”

This isn’t advice to run toward danger. It’s a pattern: the identity that burned out cannot simply be recharged. It has to be allowed to die so something new can emerge.

The question isn’t “how do I get back to who I was?” It’s “who do I become now?”

The Burnout Paradoxes

What causes burnout is counterintuitive. So is how to recover from it.

The Autonomy Paradox: Founders burn out at lower rates than employees—36% versus 50%—despite objectively higher demands. The explanation: high control and autonomy can offset high stress. Founders steer the ship, so the emotional toll is often less severe than for those who bear the stress without the agency.

This reframes the cure. It may not be about doing less. It may be about regaining a sense of control. Recovering from burnout isn’t so much about reducing workload as it is about reclaiming agency over the stories that make up your life and identity.

The Intrinsic Motivation Paradox: Managers assume intrinsically motivated employees will enjoy additional tasks—leading them to pile more work on exactly the people they should be protecting. 55% of managers allocated extra tasks to their most motivated employees. Your passion can backfire. The reward for good work is more work. The reward can become a punishment.

Burnout Lives in Your Body, Not Your Mind

Burnout is embedded in the nervous system. Cognitive approaches can help reframe thoughts around stress, but no amount of willpower or rest will override the biological safety mechanism of a nervous system in protective shutdown.

What many interpret as laziness or lack of motivation during burnout is often a trauma response.

Polyvagal theory offers a clear sequence: state awareness and bottom-up regulation must come first. Cognitive and narrative integration follow. Regulatory conditions must be created before engaging cognitive processes.

Specific interventions with some evidence:

• Breathwork (diaphragmatic breathing, 4-7-8 technique) activates the parasympathetic system

• Nature exposure: spending at least 120 minutes per week outdoors was associated with 59% higher likelihood of reporting good health in a study of nearly 20,000 people

• Cold exposure and humming/singing stimulate vagal toning

Without a specific intervention for your body, burnout recovery may not hold. These small acts done consistently will do the heavy lifting in unconditioning the nervous system after it has absorbed long-term stress.

From Obsession to Harmony

Research on passion distinguishes between two types: harmonious and obsessive.

Harmonious passion involves engagement that coexists with other life areas. Obsessive passion is rigid, compulsive engagement that crowds out everything else. Longitudinal findings confirm that harmonious passion protects against exhaustion. Obsessive passion predicts burnout. This is a fine line many creatives have experienced after launching themselves into a project that took control over their entire lives.

The fire that burned you out was probably obsessive—consuming other parts of life, fed by external validation, impossible to turn off. The fire that can sustain you is harmonious—integrated with the rest of your life, powered by internal alignment rather than external demand.

The Taoists called this wu wei—often translated as “effortless action” or “non-forcing.” Not the absence of effort, but effort that flows rather than forces.

Self-compassion turns out to be one of the most consistent predictors of burnout recovery. Kristin Neff’s research suggests a practice: treat yourself as you would treat a struggling friend. The harsh internal critic that drove you to burnout won’t drive you out of it. Mentally reframing conditioned, negative self-talk is key to enabling self-compassion.

Same Fire, Different Source

Burnout is external fire—demands from outside burning through you, depleting the self.

Burning inside is internal fire—purpose and meaning that generate from within, sustaining rather than consuming.

“Like a bellows: [the Tao] is empty yet infinitely capable. The more you use it, the more it produces.” — Tao Te Ching

That’s the difference. Obsessive fire depletes the more you use it. Harmonious fire produces more the more you use it.

Wu wei. Effortless action. Not pushing through, but flowing from. Flow state is maybe the oldest prevention and cure to burnout there is—a healthy counterweight to what burnout often feels like: swimming upstream. The sense of flow we feel in creative, deep work is wu wei in action. And the reason it’s called “flow” is that it feels like floating downstream, harnessing natural forces rather than fighting them.

That statement about introspection made me pause. I had to wonder, what is he really saying? And how does he even define introspection? No specific framing was given in the interview, so the very concept remains open to your own interpretations.

At the core, the question to ask is an interesting one for this week’s post:
What role and value introspection actually plays in entrepreneurial psychology? And how can introspection backfire on you - in terms of your inner life as a founder: feeling happy, creative, effective and impactful.

Here’s my own interpretation of what Marc means by ‘zero introspection’:
the best founders have just relentless forward motion, this non-stop bias for action. They don’t feel a need to slow down, to reflect deeply on their meaning in life - it’s so painfully evident that their answer lies outside of them, not deep within on the other side of a psychedelic trip. Their purpose is their calling and the existential crisis questions don’t even arise for them given how deeply their motivations burn.

How is introspection different than self-awareness and meta-cognition? Clearly founders are learning machines and so they have to be clear on where they stand and what is required to get to the next stage. Great founders have great self clarity - and that is a useful form of introspection: What works, what doesn’t, what skills to build, what lands well with others, etc.

Executive coaches, leadership retreats, journaling protocols, meditation apps, founder therapy -- all built on the premise that looking inward drives better performance. Billions of dollars circulate around the idea that self-awareness is a competitive advantage and what makes leaders their most effective, best selves.

The introspection paradox is not whether to look inward to find answers, you will. It’s whether you can trust what you find there.

• Introspection: the examination or observation of one’s own mental and emotional processes.

• Self-Awareness: conscious knowledge of one’s own character, feelings, motives, and desires, including an understanding of how one is perceived by others

• Meta-Cognition: awareness and understanding of one’s own thought processes.

The Confabulation Problem

You Don’t Know Why You Do What You Do

In 1977, Richard Nisbett and Timothy Wilson laid out four identical pairs of stockings and asked shoppers to pick their favorite. Position mattered enormously -- people overwhelmingly preferred the pair on the far right. When asked why, every participant gave a confident, detailed explanation. The texture was softer. The color was richer. The knit was tighter.

None of it was true. The stockings were identical. Their brains invented a plausible, coherent, completely fabricated story.

We do not introspect. We confabulate.

Nisbett and Wilson’s conclusion was stark: we have no direct access to our own cognitive processes. What feels like introspection is a post-hoc narrative our brains generate to explain decisions already made by mechanisms we can’t observe. Nick Chater took this further in 2018: “The mind is flat. There are no hidden depths.” The authentic self founders are told to discover -- buried beneath the noise, waiting to be excavated through journaling and breathwork -- may not exist at all.

The Bias Blind Spot

Emily Pronin and Matthew Kugler showed in 2007 that introspection itself fuels the bias blind spot. Looking inward doesn’t reduce bias -- it increases your confidence that you’re unbiased. You examine your reasoning, find it logical (because your brain constructed it to feel logical), and conclude you’re being objective. The person who says “I’ve really thought about this” may be the person you should trust least.

Tasha Eurich’s research drives the nail deeper. After surveying thousands, she found only 10-15% are genuinely self-aware. But the unsettling finding: time spent reflecting does not correlate with self-awareness. At all. The founder who journals every morning, does quarterly retrospectives, has a therapist and a coach and a meditation practice -- that founder may have nothing more than a more elaborate confabulation. A richer fiction. A higher-resolution lie.

“We are all strangers to ourselves. We think we know our own minds, but that is a reassuring fiction.”
— Nick Chater, The Mind is Flat

What Andreessen Is Actually Seeing

Andreessen observes something seemingly real. The founders who “don’t introspect” by analyzing too deeply their inner processes may be avoiding a broken tool. They’ve learned -- probably without knowing the science -- that sitting with their thoughts produces noise, not signal.

The Neural Trap

Same Hardware, Different Programs

In 2015, Hamilton and colleagues found that self-reflection and depression activate overlapping regions of the Default Mode Network -- the brain’s “idle” circuit that fires when you think about yourself, your past, your future. No neurological firewall separates productive self-examination from the recursive self-focused thinking that characterizes clinical depression. The only difference is which program runs -- and you don’t always choose.

Trapnell and Campbell identified this in 1999. Two constructs -- rumination and reflection -- produce opposite outcomes. Reflection correlates with openness and growth. Rumination correlates with anxiety and paralysis. From the outside, they look identical. Same posture. Same brain regions. Different programs on the same processor. The person running the program often can’t tell which one they’re in until the damage is done.

Verbal Overshadowing

Jonathan Schooler’s research on verbal overshadowing revealed that putting intuitive knowledge into words degrades the knowledge. In his original 1990 study, participants who verbally described a face they’d seen became significantly worse at identifying it afterward. Melcher and Schooler (1996) extended this to taste -- wine drinkers who described a wine’s qualities became worse at recognizing it. The verbal description overwrote the richer, non-verbal representation. Beilock and Carr (2001) found the same pattern in skilled performance: conscious monitoring of expert behavior destroys the behavior. That’s why top Olympic athletes aim to approach the most decisive moments of their sports lives by just having fun and enjoying the ride - to avoid freezing up physically due to overly analytical processes.

The instinct to “think through” a decision you intuitively understand -- to articulate your reasoning, make it legible -- may actively degrade the decision. Counterintuitively, that’s why trusting your gut is key, especially in stressful, high-stakes moments.

Breines and Chen (2012) challenge another common entrepreneurial myth: that self-criticism drives improvement. Self-compassion -- not self-criticism -- produced greater motivation to change after failure. The “I need to be harder on myself” narrative is empirically counterproductive. You learn by treating yourself the way you’d treat a founder you respect who brought you the same problem.

The Expert’s Trap

Experience Makes Bias Worse

The “just get more reps” crowd needs to sit down. Hmieleski and Baron’s 2009 study found that experienced founders are more harmed by optimism bias than novices. Not less. More. Experience doesn’t sand down your biases -- it gives them texture and detail, lets them masquerade as pattern recognition. The veteran who says “I’ve seen this before” may be matching a pattern that doesn’t apply, but their confidence makes the mismatch invisible.

Gollwitzer showed why. The moment you truly commit to a venture -- money, reputation, identity on the line -- your brain shifts into an “implemental mindset.” A cognitive filter designed for execution, not evaluation. Disconfirming evidence gets suppressed. Confirming evidence gets amplified. Not a choice. Architecture.

The Failure Learning Paradox

Silicon Valley’s favorite mythology -- “fail fast, learn fast” -- runs headfirst into Ucbasaran and colleagues’ 2011 finding: serial entrepreneurs do not learn from failure. The founders who actually extracted learning were portfolio entrepreneurs running multiple ventures simultaneously, comparing outcomes across contexts. Seems obvious: without a baseline you can’t tell what is luck or skill - and how generalizable the lesson really is.

The broader literature on situated learning suggests that reflection on failure only produces learning within the same domain -- switch industries, and the lessons don’t transfer. Shepherd’s 2003 work explains part of why -- business failure causes genuine grief, with the same cognitive impairment and inability to learn that characterizes bereavement. The window when you most need to learn from failure is precisely when you’re least equipped to.

As a thought experiment, if truly introspection, self-criticism, and failure don’t help you, then what actually does?

The Entanglement Trap

Solomon’s Paradox

In 2014, Igor Grossmann and Ethan Kross studied how people reason more wisely about other people’s problems than their own. They called this phenomenon Solomon’s Paradox, after the king renowned for wisdom about everyone’s life except his own.

The mechanism: when you think about someone else’s situation, self-referential processing decreases. The freed cognitive resources produce measurably better reasoning -- more perspectives considered, more uncertainty acknowledged, more conflicting information integrated. A simple intervention -- thinking about your own problem from a third-person perspective -- restored the same quality of reasoning.

“What would I tell a founder who came to me with this exact situation?” is not a cliche. It’s a cognitive technology. It bypasses the confabulation engine by changing the brain’s mode of self-reference. The advice you’d give someone else about your problem is almost always better than what you give yourself -- because your brain processes it through different circuitry.

This reminds me of a passage in Only The Paranoid Survive, where the Intel team imagined they were fired and replaced by brand new management to think freely about what’s needed for solving the challenge at hand.

Ask What, Not Why

Eurich’s work contains a second deceptively simple finding. The word “why” triggers confabulation. The word “what” produces insight.

“Why did my startup fail?” sends the brain searching for a coherent narrative. It will find one. It will be wrong. It will feel completely true.

“What patterns do I notice across my last three decisions?” activates an entirely different mode -- observational rather than explanatory, collecting data rather than constructing stories. One word. Completely different cognitive operation.

Similarly, you’ll learn so much more valuable, actionable insights from customers if you asked them “what would make our product a 10 for you?” instead of asking them why they like/dislike your product.

Reframing Introspection

What Andreessen Gets Right

Identity-level introspection -- the “Who am I really?” variety -- can reduce entrepreneurial action. Montiel Campos’s 2019 study in the Journal of Small Business Management found mindfulness practices actually decreased initiative in novice founders. Flow states require the prefrontal cortex’s self-monitoring to go quiet -- as Csikszentmihalyi and Dietrich showed, self-consciousness is neurologically incompatible with peak performance. The rumination culture telling founders to “sit with their feelings” and “do the inner work” can become a socially rewarded form of inaction dressed as wisdom. And the mind is never at its best when looping in a vacuum - you need external stimuli - hence why purely inner work without corresponding intentional action is a waste.

On the other hand, the best way for a depressed person to get out of their own self-loathing state is through action - this is where motivation comes from, not the other way around. Action produces meaning, meaning produces motivation.

What Andreessen Gets Wrong

Metacognition -- monitoring and adjusting your own thinking in real time -- predicts venture success. Haynie and Shepherd showed it correlates with sustainability, innovation, and revenue growth. Experience without metacognition makes founders worse. The bias entrenches. The pattern matching ossifies. The confabulations grow more sophisticated.

The “zero introspection” founders Andreessen admires almost certainly practice metacognition. They just call it “learning from the market” or “listening to the data” or “war gaming with my co-founder.” They’ve moved the reflective process outside their own heads -- exactly what the research prescribes.

Beware of the articulate self-narrator with a beautiful, coherent, completely fabricated understanding of why they do what they do. Most people unconsciously tend to explain their behavior using post-rationalization - when in fact the action is the prerequisite to the insights - not the result of a grand idea.

Founders who appear to have zero introspection are often the most metacognitively sophisticated people in the room. They’ve learned that the mind cannot be trusted to examine itself honestly. So they moved the process outside their heads. Built systems to guide their own thinking, forcing a dose of reality to keep them on the path. They have no need to re-evaluate if they could be happier doing something else - that concept is totally alien to someone who found their life’s calling. They ask concrete “What?” instead of emotional “Why?”. Treat their own problems with the perspective of an outside observer.

As Socrates said, the unexamined life is not worth living. But the self-examined life may not be entirely trustworthy. The solution is not to stop examining. It is to stop trusting yourself to do it alone, leaving your mind to run wild. Anchor your self-reflection in action and experiments.

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I call the system Super_Agents and it’s free to use. It’s a personal OS on steroids: flexible, thoughtful, personal, and designed around the way founders actually think and work. The system has over a hundred LLM sub-agents, each with a distinct role, personality, and evaluation criteria. Some plan my weeks. Some coach me on blind spots. Some research, some write, some challenge everything the others produce. Think of it as a team that fits your needs like a glove — a team you train, and help grow in ability over time. You can use it for free.

All of this got me thinking about the essence of expertise, experience, learning, improving, and where humans and robots might overlap in terms of skills acquisition.

What does it actually take to get better?

The answer, it turns out, is the same whether you’re training an AI agent or training yourself. And it’s a bit counterintuitive.

Experience Alone Doesn’t Make You Better

Most founders believe that doing it again — launching another company, running another experiment, taking another at-bat — makes them meaningfully better the second or third time around. Seems reasonable, since entrepreneurship involves pattern matching.

Some evidence shows otherwise. Shaw and Sorensen’s large-scale analysis of serial entrepreneurs found that learning across successive ventures is a “high-noise, low-signal environment.” The progress ratio — total learning relative to starting knowledge — hovers close to 1. Experience accumulates. Improvement? Not reliably.

In 1993, psychologist K. Anders Ericsson defined three modes of practice:

• Naïve practice is repetition with the expectation that volume equals improvement.

• Purposeful practice adds goals and self-monitoring.

• Deliberate practice goes further — it requires a coach who designs activities targeting identified weaknesses, with immediate feedback and forced revision.

He used the modes to run a study on how people try to improve. Most people operate at the naïve level. Even most high-performers stay at the purposeful level. Deliberate practice — where almost all meaningful improvement actually lives — is comparatively rare.

The critical variable is not effort. It’s feedback quality. Using external systems to feedback into the inputs is the special sauce. One on one, real time, contextual feedback is useful and actionable. That’s why the very top player in any sport has a coach. Even if they are the best, they still are subjectively biased. Since they don’t need to identify what to work on themselves, they are free to just do the work to improve. All of this means tighter and better feedback loops.

Therapists don’t improve with experience when patient feedback is delayed or inaccurate — even across decades of practice. Surgeons, radiologists, financial analysts: the pattern repeats. Without timely, specific, and accurate feedback, experience doesn’t compound.

Deliberate practice is about systems design. A personal system that keeps you on the path of small, continued wins, like guardrails that prevent you from steering off too far.

Entrepreneurship is learning in adverse conditions. That is my own definition and also one that applies to antifragile systems, and these same concepts also can be put into action with Claude Code and other autonomous agent models.

Calibration vs. Confidence

Experienced founders develop strong heuristics — mental shortcuts that worked in a previous context. The research is clear: these heuristics become liabilities. The very fluency that signals expertise can mask the fact that you’re pattern-matching to a context that no longer exists.

Without external challenge, experience doesn’t produce calibration. It produces overconfidence that leads to ruin.

Surprise, Not Failure, Is the Best Teacher

Butterfield and Metcalfe documented what they called the hypercorrection effect: when you make an error you were certain about — not a careless mistake, but a confident, load-bearing belief — and then receive accurate feedback, the learning signal is stronger than when you’re corrected on something you already doubted.

The bigger the gap between your confidence and reality, the more powerfully the correction sticks.

Your brain flags the moment: this belief was structural, and it was wrong. Rebuild. The surprise is functional. It captures more attention, produces better retention, and drives faster behavioral change than any feedback on things you already suspected might be off.

The implication is uncomfortable: the most valuable feedback isn’t the kind that catches your known weaknesses. It’s the kind that exposes your confident wrongness — the corrections you don’t see coming.

For founders, this means the advisors who agree with your worldview are performing the least useful version of their function. The real value lives in the person — or the system — that challenges your certainties. With enough specificity to act on, and enough surprise that it actually lands.

For founders with ADHD — significantly overrepresented in entrepreneurship — there’s an additional constraint. Learning from errors requires what researchers call emotion and motivation control: the capacity to sit with the discomfort of being wrong without the nervous system hijacking the cognitive work. The feedback has to be legible enough to process and the environment safe enough to sit with. This isn’t background noise. It’s a first-order constraint on whether the feedback loop functions at all.

The Bar Raiser

Ok so let’s bring everything we’ve discussed so far together in a concrete way. One of the most useful mental models I picked up working at Amazon is the Bar Raiser — a person embedded in every hiring loop whose sole job is to protect the quality standard. An external evaluator with one question: will this person raise the talent baseline overall?

The Bar Raiser works because of what it is, architecturally: an external input, free from groupthink, evaluating against explicit criteria rather than vibes. A feedback loop built into the system by design.

When I started building Super_Agents, this became the most important pattern I implemented. Every team of sub-agents working toward a shared outcome has a Bar Raiser agent sitting outside the workflow. It doesn’t generate. It evaluates. Specifically, it:

• Defines what quality looks like for each agent’s input and output

• Measures those dimensions over time

• Delivers a clear scorecard with learnings — often prompting the agent to redo the work entirely from a different angle

• Aggregates patterns across all agents so the system learns as a whole, not just in parts

The result isn’t magic. It’s the same science, applied structurally. The AI research calls it RLAIF — Reinforcement Learning from AI Feedback — where an agent learns to evaluate its own outputs and improve through that evaluation. What the research shows: the quality of the evaluation function determines the ceiling of the entire system. Not the capability of the generator. The sophistication of the critic.

But here’s where the parallel between human and machine learning differ. AI agents can be reset. Retrained from scratch. You can swap out a reward model overnight. Founders can’t. Your evaluation function — the internal standard you hold yourself to — was formed over decades. Shaped by childhood, by early career feedback, by the first investor who said yes or the co-founder who said you were wrong. It’s not a model you can retrain. It’s a deep psychological structure.

It’s a lot harder for us humans to unlearn our conditioning. We have no factory reset option.

What Every Learning System Needs

Across learning science, entrepreneurial cognition, AI alignment, and error-correction neuroscience — the same architecture emerges:

• An evaluation standard specific enough to act on. Not “do better.” A standard that distinguishes a 6/10 output from a 9/10 and can articulate why.

• Timely feedback against that standard. Not quarterly board meetings. Feedback that arrives while the context is still fresh enough to learn from.

• Forced revision. Not optional. Structural. The system doesn’t proceed until the output has been challenged and improved.

• Regular recalibration of the evaluation function itself. The standard has to evolve. An evaluation function that worked for your first company may be actively misleading for your third.

The Bar Raiser has to be bar-raised too, once in a while.

Have a nice week end.

Selected References

• Ericsson, K.A., Krampe, R., & Tesch-Römer, C. (1993). The role of deliberate practice in the acquisition of expert performance. Psychological Review, 100(3), 363–406.

• Shaw, K., & Sørensen, A. (2016). The productivity advantage of serial entrepreneurs. Journal of Labor Economics, 34(S2), S99–S132.

• Butterfield, B., & Metcalfe, J. (2006). The correction of errors committed with high confidence. Metacognition and Learning, 1, 69–84.

• Mitchell, J.R., Busenitz, L.W., Bird, B., Gaglio, C.M., McMullen, J.S., Morse, E.A., & Smith, J.B. (2007). The central question in entrepreneurial cognition research. Entrepreneurship Theory and Practice, 31(1), 1–27.

• Lee, H., Phatale, S., Mansoor, H., et al. (2023). RLAIF vs. RLHF: Scaling reinforcement learning from human feedback with AI feedback. arXiv:2309.00267.

• Antshel, K.M. (2018). Attention deficit/hyperactivity disorder (ADHD) and entrepreneurship. Academy of Management Perspectives, 32(2), 243–265.

As an entrepreneur, this is one of the most under-appreciated skills to develop.

What I mean by Seeing Around Corners is about picking up on weak signals, spotting messy patterns, and acting with clarity and purpose. Seeing around corners is not the same as predicting the future. Let’s be clear: no one can reliably predict the future.

The best we can do is see the present clearly and act early.

In 1985, Andy Grove asked Gordon Moore a question that would save Intel.

“If we got kicked out and the board brought in a new CEO, what would he do?”

Moore didn’t hesitate: “He’d get us out of memories.”

Grove: “Why shouldn’t you and I walk out the door, come back, and do it ourselves?”

They exited the memory chip business — Intel’s founding product, their identity, still profitable — and bet everything on microprocessors.

In retrospect, it looks inevitable. At the time, it was terrifying.

We talk about founders who “see around corners” as if they have a supernatural gift. They don’t. What they have is a cognitive discipline that scientific research can explain — and that you can practice.

1. Opportunity Prototypes & Recalibration

Robert Baron’s research (Academy of Management Perspectives, 2006) showed that great founders don’t predict the future. They detect meaningful patterns across seemingly unrelated events and connect them faster than anyone else.

Baron studied novice vs. experienced entrepreneurs and found something specific: experienced founders carry richer “opportunity prototypes” — mental templates for what a good opportunity looks like. They don’t just see more. They see differently, because their prototypes have been recalibrated by failure across multiple domains.

Your prototype is shaped by where you’ve succeeded. If you’ve only built in SaaS, your opportunity prototype is calibrated for SaaS. You’ll pattern-match everything against SaaS templates — and miss opportunities that don’t fit the mold.

The founders who see around corners aren’t the ones with the most dots. They’re the ones whose dots come from domains where their existing prototype failed, forcing a recalibration.

Luis von Ahn spent a decade in academic computer science, studying how humans solve problems machines can’t. He built CAPTCHA, then reCAPTCHA — turning those human solutions into labor that digitized books. Then he noticed a pattern: millions of people were voluntarily solving problems online. He associated that behavioral signal with the broken economics of language learning and the engagement loops of mobile games. Duolingo. An academic who’d never built a consumer product saw an opportunity that every edtech founder missed, precisely because his prototype was shaped outside the industry.

You don’t improve pattern recognition by going deeper in your domain. You improve it by deliberately exposing yourself to domains where your current opportunity prototype breaks. That’s where recalibration happens.

2. Alertness Is a Muscle, Not a Gene

Israel Kirzner (1973) defined entrepreneurial alertness as a cognitive readiness to notice what others overlook. He treated it theoretically — but didn’t offer a practical model for developing it.

Tang, Kacmar, and Busenitz (Journal of Business Venturing, 2012) did. They decomposed alertness into three trainable components:

Scanning — actively searching for new information.

Association — connecting new information with what you already know.

Evaluation — judging whether the connection represents a real opportunity.

Most founders only scan. They read industry news, follow trends, attend conferences. Necessary but insufficient.

The real leverage is in association. Deliberately asking: “What does this remind me of in a completely different domain?”

Grove ran all three steps as an organizational system, not just a personal habit. He didn’t just scan Japanese manufacturing data — he associated it with a pattern he’d seen in other industries where a cheaper, good-enough competitor displaced the incumbent. He evaluated it as a “10X force” — not normal competition, but a fundamental shift. Then he embedded that scanning-association-evaluation loop into Intel’s culture. “Only the paranoid survive” was an organizational alertness system.

You need less information and more association across domains.

3. Signal Fatigue

How many signals should you act on?

Gali, Hughes, Morgan, and Wang (Entrepreneurship Theory and Practice, 2024) studied 804 large US tech firms over 18 years. Their finding: every one-point increase in Entrepreneurial Orientation — risk-taking, innovativeness, proactiveness — increases the risk of firm failure by 24.9%.

The data is about firms, not individual founders. But the mechanism — irreversible resource depletion from too many bets — operates at every scale. Each initiative that doesn’t work burns resources that can’t be recovered. The entropy accumulates. Abrupt strategic changes compound the risk further, especially for firms already underperforming.

Founders who see around every corner and act on every signal exhaust their resources chasing optionality. The discipline isn’t in seeing more. It’s in choosing less.

Jensen Huang understood this before anyone. In the mid-2000s, NVIDIA was printing money from gaming GPUs. Huang killed profitable consumer product lines to bet on CUDA — a platform for general-purpose GPU computing that almost no one was asking for. The gaming industry thought he was insane. He saw AI and scientific computing coming a decade early. But the move that mattered wasn’t the bet on CUDA. It was the disciplined killing of revenue lines that would have diluted the bet.

Before acting on any signal, two questions:

1. What does this bet cost if it fails? (Not just money — attention, team energy, opportunity cost.)

2. Can I absorb the loss and still fund the next bet?

Don’t act on all the signals. Let them sit. Keep narrow and focused. Be intentional about the signals you choose to ignore — and hold yourself to it.

4. Uncertainty as Possibility (Not Anxiety)

Psychological entropy — the uncertainty that creates anxiety that creates paralysis — is the bottleneck between knowing and acting.

Noubar Afeyan built Moderna on a thesis that mRNA could be a platform, not just a therapy. For a decade, every pharma company that looked at mRNA saw a drug delivery mechanism — one application at a time. Afeyan, whose prototype was shaped by founding 60+ companies through Flagship Pioneering, saw a programmable infrastructure. The scientific community was skeptical. Investors were lukewarm. Afeyan held the uncertainty for ten years before COVID validated the platform thesis. That’s not conscientiousness. That’s emotional regulation at a scale most founders never face.

The pathological version is the founder who appears conscientious but cannot adapt. Rigid plans, polished decks, meticulous control — all masking an inability to hold uncertainty. The plan becomes the prison. Conviction without calibration.

Seeing Around Corners

Step Mechanism Practice SEE Pattern recognition Expose yourself to domains where your prototype fails. Recalibrate, don’t just accumulate. NOTICE Entrepreneurial alertness Force the association step: “Where have I seen this before, in a different context?” SELECT Signal discipline Resource audit before every bet. Kill bad bets fast. Subtraction > addition. ACT Emotional regulation Check your state before deciding. Clarity, not anxiety. The plan serves you; you don’t serve the plan.

To boil it down: Grove saw that his main business was toast and that Intel needed to hard pivot — and he was right to be paranoid. Grove scanned Japanese competition (SEE), associated it with historical displacement patterns (NOTICE), chose the single bet — microprocessors — and killed memory (SELECT), then held the terror of abandoning Intel’s founding product long enough to execute (ACT).

He didn’t predict the future. He was seeing around the corner.

"The real voyage of discovery consists not in seeking new landscapes, but in having new eyes." — Marcel Proust

Happy Sunday ✌🏻🌕

Read Tao of Founders

Sources: Baron (2006) · Kirzner (1973) · Tang, Kacmar & Busenitz (2012) · Gali, Hughes, Morgan & Wang (2024)

“The eye movements of expert players show that the first idea that comes to mind directs attention toward sources of information consistent with it and away from inconsistent information.” — Bilalić et al., Why Good Thoughts Block Better Ones

When experts see a familiar solution, their eyes lock onto it. Eye-tracking data shows they literally stop seeing alternatives. The first idea that feels familiar directs their attention toward confirming information and away from contradictory information. They can’t unsee what they know. They are conditioned.

This is called the Einstellung effect. And it explains why it can actually be harder to succeed as a second-time founder.

The Expertise Trap

We all tend to default to what is familiar and avoid what is unfamiliar. A founder who scaled Company A through SEO can’t see that Company B needs community-led growth. Not because SEO is wrong — because their pattern-matching from past success has become rigid. What worked before feels like “how it’s done.” The mental model that enabled the first win becomes the cognitive cage for the second.

“Empty your mind, be formless. Shapeless, like water. If you put water into a cup, it becomes the cup. You put water into a bottle and it becomes the bottle. You put it in a teapot, it becomes the teapot. Now, water can flow or it can crash. Be water, my friend.” — Bruce Lee, Longstreet (1971)

Jeff Bezos understood the danger of limited and rigid beliefs. He tried many times to launch Amazon’s marketplace before landing on the right approach. Amazon Auctions failed. zShops failed. Some founders would have developed learned helplessness around third-party selling.

But Bezos compartmentalized. In his 2016 letter to shareholders, he wrote: “I believe we are the best place in the world to fail (we have plenty of practice!), and failure and invention are inseparable twins.” He didn’t let domain failure generalize. When Marketplace (third-party sellers on the same product pages) worked immediately, he wasn’t surprised. He’d treated each failure as insight, not identity.

Success validates your mental models, which then calcify into asymptotes — invisible ceilings you can’t see past. The better you get at something, the blinder you become to alternatives. Expect to have to unlearn and relearn many times in your entrepreneurial career — any piece of knowledge or insight sooner or later becomes obsolete. Constant reinvention is crucial, and it starts with the willingness to begin again, and again — perpetual self-reinvention.

Invisible Mental Asymptotes And Self-Growth

Eugene Wei, the first analyst in Amazon’s strategic planning group, wrote in 2018 about “invisible asymptotes” in business — growth ceilings companies hit before they see them coming. Amazon’s was shipping fees. Customers hated paying $5.99 at checkout, no matter how good the selection. It capped purchase frequency and customer acquisition. Prime didn’t just solve this; it reframed the cost as a subscription.

Wei’s system’s thinking framework is brilliantly simple: identify the asymptote before you hit it by asking, “What would prevent 10x growth from here?”

Now the real insight: the way Eugene answered this question is brilliant. He didn’t only interview current (happy) customers. He found the ones that did not buy — those that had the intention but somehow got turned off.

Unless you actively seek this kind of interaction, it will be entirely invisible to you. Of course existing customers’ input can be valuable, but if you want to reach product-market fit, your time is best spent uncovering the silent killers of your product — those things that stand in the way of potential customers giving you their money. Go find what the data won’t tell you.

In other words, the steep and direct route to product-market fit is to talk to almost-customers and ask them what was missing for them to convert. Everyone knows they should talk to their users — but I rarely see anyone trying to learn from someone who didn’t buy. And with them lies all the invisible blockers you can’t see.

The asymptote also applies from the inner side of entrepreneurship.

How will you know what stands in the way of 10x-ing your own personal growth if you don’t honestly try to surface and debunk your own imposed beliefs?

Most of the ceilings you’re hitting aren’t real constraints. They’re mental models that served you in the past - and so you’re attached to them. They prevent you from seeing clearly what is needed. They are conditioned patterns — the opposite of thinking from first principles. Your job is to make the invisible blockers visible, so you can make a plan to address them.

Mental Asymptotes

1. Capability Asymptotes

“I’m not technical.” “I’m not a salesperson.” “I can’t do accounting.”

Carol Dweck’s later research acknowledges that people can hold different mindsets about different attributes — growth-oriented about product but fixed about fundraising. Some founders who master one domain (engineering) unconsciously install fixed mindsets in adjacent domains (sales, hiring) by treating them as innate talents rather than learnable skills. Under pressure, even growth-minded founders slip into fixed thinking. Stress amplifies domain-specific ceilings.

2. Reference Point Asymptotes

Kahneman and Tversky’s anchoring research shows initial reference points disproportionately shape what feels “realistic.”

The YC batch effect works because it shifts reference points. When your batchmates aim for unicorns, $20M exit offers stop feeling like “great” and start feeling like “small.” You’re not more capable — your ceiling was anchored.

Geographic asymptotes work the same way. A Montreal founder vs. a San Francisco founder observes different peer groups and adopts different ceilings. Ambition is contagious, but so are asymptotes. One might come to believe they can’t build anywhere outside of SF, while others come to believe they can totally build a great company from anywhere. A lot of this isn’t about the ecosystem per se, but the places you have been exposed to.

3. Borrowed Asymptotes

Most of your limits aren’t yours. You internalize social constructs as ground truth.

“Solo founders can’t scale.” “B2B SaaS needs an LTV/CAC of 5 and a 12-month payback.” “You need an elite pedigree to raise from top VCs.” “Consumer social is dead.”

These feel like thoughtful wisdom. They’re asymptotes disguised as data points. They might be correct — but recognize the risk of not challenging them first. I’d bet a lot of startups regret taking large amounts of funding at high valuations, not understanding this meant a death warrant if interest rates rose and multiples compressed.

Listen to any successful founder’s story and there is almost always a time where they seemed crazy to not listen to others - and that pushback led them to success directly. That’s why a lot of the entrepreneur’s role is to be an astute contrarian: to be willing and able to go against the convention - thanks a heavy dose of independent thinking and earned insights.

Many founders tend to raise with a mimetic mindset: X raised $ from Y, so why not us too? It takes a different type of founder to shy away from doing what they can and focus on what they should.

Albert Bandura’s research on vicarious experience shows seeing someone “like you” succeed expands your self-efficacy ceiling. But it works in reverse: seeing people accept limits installs those limits in you. You don’t consciously choose these beliefs — you internalize them from investors’ mental models, industry “best practices,” accelerator gospel, peer group consensus. None of this is great for original thinking.

Edwin Land wasn’t from the photography industry, so he didn’t know what was “impossible.” When Polaroid’s engineers said instant photography couldn’t work, Land treated it as an engineering puzzle, not a ceiling. His outsider status was an asset. As he once said: “From then on, I was totally stubborn about being blocked. Nothing or nobody could stop me from carrying through the execution of the experiment.” He refused to accept industry asymptotes he’d never learned. And he won.

Sara Blakely, founder of Spanx, had the same advantage. No business school meant no MBA asymptotes about “how to scale consumer products.” So she just went for it.

4. Learned Helplessness Asymptotes

Martin Seligman’s research on learned helplessness shows repeated failure in one domain can create either domain-specific helplessness or generalized helplessness, depending on your explanatory style.

Pessimistic explanatory style: “I failed at fundraising” becomes “I’m bad at business” becomes “I’m not cut out for this.” The domain-specific failure contaminates adjacent domains. Permanent, personal, pervasive.

Optimistic explanatory style: “That pitch sucked” (specific, temporary, external). The failure stays contained. Try again with a different approach.

Even successful founders develop learned helplessness in small domains — hiring, media, partnerships — from repeated early failures. They come to hate that part of their jobs and so they more or less avoid dealing with it. The asymptote feels like reality: “I’m just not good at X.” But it’s always learned, not inherent. You impose that belief on yourself, it just isn’t reality.

Breaking Your Asymptotes

Find Peer Groups

Bandura’s vicarious experience mechanism: seeing someone “like you” succeed expands your ceiling.

Solo founders without peer groups develop artificially low ambition because they lack reference points. Join communities not just for resources but for reference point expansion. Watch how other entrepreneurs navigate constraints you thought were immovable. Read biographies or listen to the Founders podcast to build a diverse set of tools and models as inner resources, so you can more easily see when your views are conditioned — you’ll have a contrasting background to compare your own patterns against (e.g. what would X, Y, or Z do in my situation?).

For me the sweet spot is a peer group who is around your own stage / life situation, so they can related, and also people who are able to give you 1:1 direct, relevant feedback that helps you address what you don’t see.

Question the Patterns from Previous Success

After a big win, the dangerous move is assuming your approach is universal. Instead, take a detached stance and identify:

• What worked because of that specific market, moment, or team?

• What might work differently in a different context?

• Where am I pattern-matching when I should be thinking fresh?

Reframe Domain Failures

When you fail at something specific (fundraising, hiring, media), don’t let it generalize.

Not: “I’m bad at this” (permanent, personal, global)

Instead: “That approach didn’t work” (temporary, external, specific)

Compartmentalize. A failed pitch doesn’t mean you can’t raise — it means that pitch didn’t land. A bad hire doesn’t mean you can’t hire — it means your process needs adjustment. Keep the failure contained to the domain so it doesn’t install a global ceiling.

Only by shedding light on your invisible asymptotes can you understand and address them. Don’t focus on what you can see — focus on what is left unseen, what is missing, what you don’t know that you don’t know. Like Wei did, you can learn from what is (your customers) but more importantly from what isn’t (non-customers) — and remain open to wherever that leads you.

Quick Ask: Help me decide what to write next. Share your ideas, feedback and opinions. Just reply to this email or add in the comments below on web.

Have a nice weekend ✌🏼

Read Tao of Founders

His autobiography includes a chapter called “Deal with Your Dark Side.” It’s not about competition, market risk, or strategic failure. It’s about rage. Shame. Emotional extremes that built an empire and nearly destroyed the man behind it.

A partner described working with him: “Paul could be abusive. He could be hostile. But he could flip that and be phenomenally gracious. There was constant turmoil. You never knew what was expected of you.”

I wrote Tao of Founders to share with other founders how I am learning to cope with my own emotional extremes. Last year I also wrote a post on neurodiversity and entrepreneurship. Many of you reached out to share your own ADHD, ASD, dyslexia stories, and so on.

What’s incredible is how little we still know about what actually drives ADHD. For better or worse, it is an entrepreneurial “disorder” — found in around 29% of diagnosed entrepreneurs, six times the rate in the general population.

This is Part 2 of that neurodiversity post. I want to explore the things I found most surprising, misunderstood, and under-discussed about ADHD specifically. It’s not a condition you can diagnose with a scan. Diagnostics rely on subjective observations of behaviours and brain patterns. ADHD affects such a wide range of executive functions, with no clear cause-effect relationships between dysfunctions and real-life symptoms, that it took me years to understand how it shows up — how it affects my brain, my moods, my energy, my physiology.

This is the part of ADHD nobody talks about in founder culture. Not the “hyperfocus superpower.” Not the “risk-taking edge.” The emotional dysregulation. The shame after the outburst. The hypersensitivity to rejection. The chronic inability to fully recognize your own worth. The constant feeling you should be doing something else that burns you to the ground. Now let’s get real.

ADHD is NOT about attention

Dr. Russell Barkley, a leading ADHD researcher, has argued that ADHD should be renamed Self-Regulation Deficit Disorder. His reasoning is simple: the fact that someone with ADHD can hyperfocus on a startup for 16 hours but can’t file taxes proves it’s not an attention problem. The attention works fine. The executive control over where to direct it doesn’t.

ADHD breaks down seven self-regulation skills simultaneously: self-awareness, impulse inhibition, attention management, working memory, error detection, emotional regulation, and problem-solving under pressure. “Focus” is just one visible casualty of a much deeper systems failure.

When you frame ADHD as “attention deficit,” the solution seems obvious: try harder to pay attention. Use a timer. Close your tabs. But when you frame it as a self-regulation deficit, the solution shifts entirely — toward designing systems, environments, and external scaffolding that do the regulating for you.

This is exactly what many ADHD founders unconsciously do. Orfalea couldn’t sit still in an office, so he became “chief wanderer” — visiting Kinko’s stores instead of managing from a desk. He couldn’t read well, so he built a culture of delegation and trust. He couldn’t operate a single machine in his own company. It didn’t matter. He redesigned the job around his brain instead of forcing his brain into the job.

Many ADHD people feel rejection more intensely

Here’s the thing most people — including many clinicians — get wrong about ADHD: the most impairing symptom isn’t even in the diagnostic criteria.

Emotional dysregulation — the inability to regulate emotional responses proportionally — affects 55% of adults with ADHD at a severity level exceeding 95% of the general population. Over 60% report quick anger, impatience, and emotional overreaction. Less than 15% of people without ADHD report the same.

Yet it’s nowhere in the DSM. The diagnostic manual describes ADHD as an attention and hyperactivity problem. The emotional core — the engine driving everything else — is invisible in the official definition.

This emotional core has a name most founders won’t recognize: Rejection Sensitivity Dysphoria. RSD describes the unbearable emotional pain triggered by perceived rejection or criticism. Not “feeling bad.” A physiological response so intense it can be confused with a panic attack.

For founders with ADHD, handling rejection is harder. By default, they might interpret a VC “no” as personal annihilation, or obsess over one negative customer review while ignoring a hundred positive ones, or people-please until overcommitment leads to burnout.

Quite a paradox: the people who need the thickest skin are often the most sensitive to rejection.

And underneath the rejection sensitivity lies something older: shame. A chronic sense of a deficient self. Children with ADHD receive way more negative messages than their neurotypical peers. Corrections, criticisms, “pay attention”s, “try harder”s, disappointed looks. Often, this creates a reservoir of internalized stigma that no amount of adult achievement can drain.

People with ADHD are wired differently and know they are different. The question is whether they view being different as good or bad. Many evolve in an environment that pushes them to take a negative view of their own makeup.

In Scattered Minds, Gabor Maté puts it precisely: “ADHD adults don’t have low self-esteem because they are poor achievers — it’s due to low self-esteem that they judge achievements harshly.”

The founder who can’t celebrate wins. Those too hard on themselves. Those who move the goalpost after every milestone. Those who dismiss compliments because “it wasn’t that hard.” This isn’t ambition. It’s low self-esteem in disguise.

“I’m sorry” is the most common phrase in the ADHD vocabulary — apologizing for existing, for having problems, for taking up time. When I saw this fact I felt attacked. I thought I was just being Canadian by saying sorry when I don’t know why I’m saying it. It wasn’t humility or being nice. It was subconscious shame.

Another cruel paradox: successful ADHD founders often carry more shame than their struggling counterparts. Because success proves you “should” be able to handle everything. Every slip becomes moral failure rather than neurological reality. The mask gets heavier the more there is to protect.

Temporal blindness makes everything urgent and important

There’s a concept in ADHD research called temporal myopia — being nearsighted to time. Barkley first described it in a 1997 paper: just as nearsighted people can only see objects near them clearly, people with ADHD can only deal with things near them in time.

For the ADHD brain, there are only two time zones: now and not-now.

Not-now is infinity. Tuesday and 2035 occupy the same cognitive space. A Slack message and a quarterly strategy decision carry the same felt weight, because the future doesn’t exist emotionally — only the present does.

David Neeleman, the founder of JetBlue (and three other airlines), puts it this way: “I have an easier time planning a 20-aircraft fleet than I do paying the light bill.”

This isn’t a humble brag. It’s the literal experience of a brain that can envision a ten-year future but cannot feel the difference between “three months from now” and “three years from now.” The vision is real. The timeline is fog.

For founders, temporal myopia creates a specific pattern:

• Urgency bias: Everything feels equally urgent because the future doesn’t register emotionally. You respond to the Slack message before the strategy memo because both exist in “now.”

• Sprint-crash cycles: Without an internal sense of time passing, you work 16-hour days until you collapse. There’s no “pace yourself” signal. The crash isn’t burnout in the usual sense — it’s a full executive function shutdown.

• Planning horizon collapse: You can improvise brilliantly through today but structurally cannot distinguish near-term from long-term decisions.

Here’s the counterintuitive part: time blindness may actually help in early-stage startups. The inability to feel how far away an outcome is makes ADHD founders more willing to endure the “valley of death” — that brutal stretch between product-market fit and real traction that kills most companies.

It is much easier to design a job around your brain than to redesign your brain around your job

Orfalea didn’t start Kinko’s because he was a visionary. He started it because he had nowhere else to go.

“It didn’t take long for me to conclude that I was, basically, unemployable. The only hope for me was to go into business for myself.”

He was fired from serving ice cream. Fired from a gas station. Fired from delivering newspapers. That seriously affected his self-worth. He remembers once sitting in his car after being fired and crying for hours. Then came the turning point: he decided that since he couldn’t please anyone else, he might as well try to please himself. I also had a similar epiphany after I got fired, and I realized then I would never be able to become the best version of myself as an employee — I had tried for 10 years before it dawned on me that trying to fit into this path would make me miserable and unsuccessful.

The common interpretation for why ADHD is so prevalent among entrepreneurs is that ADHD makes you a risk-taker, and risk-takers become founders. The reality is less glamorous. For many of us, the conventional path was never available. Entrepreneurship isn’t the brave choice. It’s the only door that was open. You just didn’t really fit anywhere else. Some are born knowing this, others like me will take decades to realize this — and that’s fine.

The point is: something interesting happens when you’re forced to build around your deficits. Orfalea couldn’t read, so he hired people who could and trusted them completely. He couldn’t sit still, so he walked 1,200 stores and spotted patterns that desk-bound managers missed. He couldn’t operate the machines, so he focused exclusively on what came out of them and whether customers wanted it.

His company became an architecture of compensation — systems designed to work around one person’s limitations that accidentally became competitive advantages. The delegation culture. The management-by-wandering. The customer obsession born from pattern recognition, not market research.

Similarly, Kamprad at IKEA invented an entire product naming system — beds named after Norwegian towns, chairs after men’s names — because his dyslexia made numerical codes impossible to remember. A personal workaround became one of the most recognizable branding strategies in retail history.

None of these founders succeeded despite their flaws. They succeeded because it forced them to take a whole different approach.

One thing Orfalea had that many don’t: a mother who saw him clearly and encouraged him to lean into his own difference, his own unique quirks — not to be embarrassed by them.

In psychology, this is called attunement: seeing possibility instead of deficit. The data suggests most ADHD children don’t get that counter-programming. The drive to build, to prove, to achieve — how much of it is vision, and how much is the internalized shame from being and feeling different, from not quite fitting in?

Post-exit identity crisis

People with ADHD tend to have three times more issues with addictions than the average population. The largest one might be workaholism. It starts from the sense that no matter what you do, how much you do, you should be doing something else.

The ADHD brain runs on what Dr. William Dodson calls an interest-based nervous system. Neurotypical brains motivate through importance, priority, and consequences. ADHD brains motivate through passion, interest, novelty, competition, and urgency. When Dodson asks his patients, “If you could get engaged and stay engaged, has there ever been anything you couldn’t do?” — the majority respond: “If I can get engaged, I can do anything.”

Startups are the perfect drug for this nervous system. Constant novelty. Urgent deadlines. Competitive pressure. Social feedback. The 16-hour days aren’t discipline — they’re the experience of a brain finally getting the stimulation it craves. The founder isn’t working hard. They’re self-medicating.

The ADHD founder cycle typically goes like this:

1. Hyperfocus phase: Intense, productive, euphoric. Hard work feels fairly easy.

2. Overcommitment: Can’t say no because each new commitment delivers a dopamine hit.

3. Exhaustion: Executive function goes offline. Not just tired — cognitively disabled.

4. Crash: Full shutdown. The kind of burnout that isn’t fixed by a vacation.

5. Shame: “Why can’t I just be consistent?” And the cycle restarts, fueled by self-recrimination.

Maté describes typical ADHD weekend despair: “Enveloped in enervated lethargy... neither active nor able to rest.” If you’ve ever spent a Sunday unable to work and unable to relax, scrolling your phone in a fog of restless paralysis — that’s not laziness. That’s what happens when the external scaffolding disappears and there’s nothing left to regulate you.

Remove the work and the stimulation system collapses. This is why post-exit depression is so common among founders. Why people go from a $100M exit to starting over within months. They can’t handle the stillness. The void feels like hell — so they feel compelled to keep achieving beyond reason.

Hyperfocus is not a superpower

It’s the same dysregulation from the other end.

Hyperfocusing also denotes poor attention regulation: it’s the opposite extreme of tuning out. The ADHD brain that can’t sit through a board meeting and the ADHD brain that codes for 14 hours without eating are exhibiting the same dysfunction. One is the accelerator stuck on. The other is the accelerator stuck off. Neither is being steered.

A lot of hyperfocus-proud founders remain unaware of the rest of the cycle above, which leads to crash and shame over and again.

You don’t get to claim hyperfocus as a desirable feature while treating distraction as a bug. They’re the same broken regulation system. The ADHD brain works perfectly — when it wants to. That’s not a superpower. That’s a machine you can’t control.

I say this as someone who does hyperfocused sessions and greatly enjoys the creative flow that comes often with a deep, intense focus. The crash that follows — the inability to do basic tasks for days afterward, the guilt, the sense that the “real me” showed up for 14 hours and then vanished — that’s the price. And the price is hidden because the output is visible but the collapse happens in private. I used to expect myself to push and hyperfocus all day every day — and now I try to leave buffers between those intensive periods, a needed buffer to recharge my executive function batteries.

If you give me the choice between hyperfocus and consistent-yet-sustainable focus, the latter wins long term, hands down. Hyperfocus needs to be used sparingly to actually work, otherwise it will make your ADHD symptoms much worse. Hyperfocus draws heavily on your executive functions, hence why it has a cost and needs a counterbalance in mental recovery.

Oh, and ADHD reduces your life expectancy

This stat comes from Barkley’s longitudinal research. Contributing factors: lower health maintenance, higher rates of smoking, shorter sleep, less exercise, poorer nutrition, risky behaviour. These aren’t lifestyle choices but downstream consequences of self-regulation failure compounding over decades. People with ADHD have a higher rate of substance abuse disorders — unsurprising if you chronically struggle to regulate executive functions and emotions.

But by the same vein: treatment can add most of those years back. Medication, therapy, environmental design, self-understanding — they work. Not because they “fix” ADHD, but because they provide the external regulation that your internal system can’t.

If the problem with ADHD is executive regulation, then the solution also lies in executive regulation. And the word executive says it: you can override your default primal conditioning by strengthening and maintaining your executive functioning. I’m not a doctor, but that’s what I understand all treatments are aimed at: sports, meditation, sleep, unstructured time, prescription drugs, and trying to attend fully to one thing at a time.

To attend means to stretch toward. To extend yourself. The cure for attention deficit isn’t another productivity system or app. It’s extending genuine attention — toward yourself, toward the wound underneath the mask, toward the parts you’ve been pretending don’t exist.

Orfalea’s mother didn’t cure his ADHD. She saw him. That was enough to change the trajectory. Most, if not all, of the downsides that ADHD entails can be managed with the right support. But understanding yourself is the critical first step — recognizing that part of you in your own thoughts and body, then designing systems to self-regulate and diffuse your overstimulated nervous system. And all of this is only possible by first accepting and valuing your own individual wiring — all quirks included.

Stop trying to fit in and you will find your place.

Have a nice Sunday ✌🏻🌖

Gui

Read Tao of Founders

Sources:

• Barkley, R. “ADHD and Life Expectancy.” Reported in American Journal of Managed Care (2019).

• Barkley, R. Factsheet on Executive Functions and Self-Regulation. russellbarkley.org.

• Maté, G. (1999). Scattered Minds: The Origins and Healing of Attention Deficit Disorder.

• Orfalea, P. & Marsh, A. (2005). Copy This! How I Turned Dyslexia, ADHD, and 100 Square Feet into a Company Called Kinko’s.

• Dodson, W. “Secrets of the ADHD Brain.” ADDitude Magazine.

• Neeleman, D. Faster Than Normal Podcast, Episode 66.

• Sandland, B. (2025). “Neurodivergent Experiences of Rejection Sensitive Dysphoria.” Neurodiversity (SAGE Journals).

• Kooij, J.J.S. (2025). “New Developments in Adult ADHD.” World Psychiatry (via PMC).

I recently had a personal insight about feeling like I constantly have too much going on. When I decide to take on a task or role, I didn’t notice there’s a hidden future tax on my time. Some things keep asking for more of your time and attention; others have a clear end point at which you no longer need to invest time or mental energy. That’s another framing on infinite vs. finite games. Infinite games are, well, infinite, and they tend to expand in size and importance over time. Finite games have a clear finish line at which point you can decide to stop or play again.

What sort of tasks keep demanding more of your time, attention, and energy? A family, a startup, Ironman training — these are things you should constantly be working on. They usually require a long-term commitment in order to do well.

On the other hand, finite tasks are, for example, automating your personal admin or delegating non-essential tasks. Or perhaps you commit to a creative project and know ahead of time what the end state will be.

This idea makes it clear why some things tend to just take all my free time away — and those infinite games compete with each other. Those big rocks compete with each other in such a way that I feel I’m always falling behind on one or many aspects at any point in time.

Bloat comes from unseen, future, and growing demands. Now the filter is whether doing something leads to doing even more in the future. You can play only so many infinite games that self-perpetuate before they compete with each other.

It’s freeing to know that, with that simple question, I’m protecting my future self from creeping, ever-growing demands that made me feel like I’m stuck in midlife molasses.

The Science of Bloat

In 2021, a team at the University of Virginia published a study in Nature that should have made every founder stop and stare. Across eight experiments with 1,153 participants, they found that people generate 8 additive suggestions for every 1 subtractive suggestion. Eight to one.

The Lego experiment made it visceral. Participants were given an unstable structure with a single wobbly column. Removing one block fixed it — for free. Adding blocks cost ten cents each. In the control condition, 59% of participants added unnecessary bricks rather than removing the one that was causing the problem. They paid money to make something worse because their brains couldn’t see the absence as a solution.

Your brain defaults to adding because subtraction is cognitively expensive. You can’t see, feel, or sense a void, so you have to work harder to grasp emptiness; your senses can’t help you. Removing instead of adding often feels very counterintuitive, awkward and uncomfortable. That’s our biases talking.

Removing, editing, curating are System 2 operations — slow, deliberate, effortful. Addition is System 1 — fast, automatic, comfortable. Your brain is basically choosing the drive-through over cooking. Every. Single. Time.

And even when you do think of subtracting, loss aversion pulls you back. Losses loom approximately twice as large as equivalent gains. In the famous endowment effect study, people given a mug demanded roughly twice the price to sell it as non-owners were willing to pay to buy the same mug — simply because it was already theirs. Cutting a feature feels like losing a limb, even when the feature adds no value.

A French replication confirmed the addition bias — but found that just telling people “remember you can also remove things” increased subtractive thinking 2.5x. The addition bias is default, not fate. You can override it. But only if you remember it’s running.

Parkinson’s Law

Northcote Parkinson wrote about the collective implications of the addition bias, initially in The Economist in November 1955. Between 1914 and 1928, the British Admiralty grew its officials from 2,000 to 3,569 — a 78% increase. During that same period, the Royal Navy shrank by a third in personnel and lost two-thirds of its ships. Fewer ships, fewer sailors, more bureaucrats. Parkinson found that organizations naturally bloat at 5-7% annually, regardless of how much actual work exists. He called it a law. It was really a diagnosis.

Bureaucratic entropy seems as predictable as thermodynamic entropy.

“Work expands so as to fill the time available for its completion.” - Parkin'son’s Law

The biology here is uncomfortable. In your body, programmed cell death — apoptosis — keeps tissues healthy by ensuring cell death exactly balances cell division. When that balance breaks — when cells refuse to die — the result is cancer. The cells aren’t malicious. They’re just growing. The problem is that nothing is stopping them.

Organizations are the same. University administrative staff grew 240% between 1975 and 2005 while faculty grew 50%. The ratchet effect means every hire, every tool, every policy creates dependencies that resist deletion. Researchers call it organizational debt — the slow accumulation of zombie processes and legacy policies nobody remembers creating.

In last week’s “Entropy-neurship“ post, I talked about channeling entropy. This is a unique role founders can play to help shape better systems: companies, public institutions, etc.

Why? As we’ve seen, people are biased toward adding and doing more — and need a reminder that they can, and probably should, also be removing. Employees need to perform and prove their value, usually by taking decisive actions. Doing nothing as a strategy tends to get less social approval — and is harder to defend when things go wrong. (Were you lazy? How do you measure the impact of doing nothing?)

The meta-evidence is clear. An integrative review of empirical studies found that constraints consistently benefit innovation, with a sweet spot of moderate constraint (Acar et al., 2019). And founder CEOs produce 31% more citation-weighted patents than professional CEOs; when a founder departs, innovation drops by roughly 44% (Lee et al., 2016).

Founders are the ones incentivized to get it right — to make the right decisions, to design the right solutions. And this is why they are typically the only people inside a company who are able and willing to design by reduction — and question whether something should exist at all.

The Scar Tissue

Nassim Taleb wrote that “knowledge grows by subtraction much more than by addition.” Knowing what NOT to do is more durable than knowing what to do. But that knowledge comes from scar tissue — from the deletions that went wrong.

The secret is subtraction. Not once, but always. Constantly.

Strategic subtraction is about design tradeoffs. To delete well, be clear on what is being removed and what the impact could be:

1. “If I removed this, what would break?”

2. “Am I cutting cost or cutting capability?”

3. “Am I optimizing for efficiency or for discovery?”

Designing by subtraction is clearly not the same as cost cutting. In fact, one is about efficiency, the other is about innovation (very inefficient). The key is that removing should set you up for a better future — not destroy your potential. With that frame, the right type of strategic subtraction is a form of investment.

As we’ve seen last week, the right way to harness entropy is to channel it, not fight it — so the right way to subtract has to be in harmony with a broader whole: removing to reallocate energy better.

“We shape clay into a pot, but it is the emptiness inside that makes it useful.

We cut doors and windows for a room; but it is the empty space that makes the room livable.

We work with being, but non-being is what we use.”

— Lao Tzu, Tao Te Ching, Chapter 11

The Japanese have a word for this: Ma. The intentional negative space. The silence between notes that gives the melody meaning. The empty wall that makes the painting visible.

Every wisdom tradition found this independently. Taoism teaches that non-being is what we use. Buddhism’s sunyata holds that emptiness is the undifferentiation from which all things arise. Michelangelo defined sculpture as “that which is fashioned by the effort of cutting away” — the artist reveals, not creates.

Perhaps the founder’s most important work is invisible. The features you didn’t build. The hires you didn’t make. The markets you didn’t enter. The meetings you didn’t hold. Nobody sees the absence. Nobody applauds the product you killed before it shipped.

But the absence is what lets everything else exist and flourish.

Happy Sunday ✌🏼🌖

Read Tao of Founders

Sources

• Adams, G. S., et al. (2021). People systematically overlook subtractive changes. Nature, 592(7853), 258-261.

• Fillon, A., et al. (2025). The Overlooking of Subtractive Changes: Replication and Extension. Journal of Creative Behavior, 59(1).

• Kahneman, D., & Tversky, A. (1979). Prospect Theory. Econometrica, 47(2), 263-291.

• Kahneman, D., Knetsch, J. L., & Thaler, R. H. (1990). Experimental tests of the endowment effect. Journal of Political Economy, 98(6).

• Parkinson, C. N. (1955). Parkinson’s Law. The Economist.

• Kerr, J. F., Wyllie, A. H., & Currie, A. R. (1972). Apoptosis. British Journal of Cancer, 26(4).

• Matejka, M., et al. (2024). The Ratchet Effect. Management Science, 70(1).

• Kocak, S. A., et al. (2024). Organizational debt. PLOS ONE, 19(11).

• UC Berkeley (2023). Twenty-year study on prescribed burns.

• Ginsberg, B. The Fall of the Faculty. Johns Hopkins University Press.

• Lee, J. M., et al. (2016). Are Founder CEOs Better Innovators? S&P 500 Firms.

• Acar, O. A., et al. (2019). Creativity and innovation under constraints. Journal of Management, 45(1).

• Iyengar, S. S., & Lepper, M. R. (2000). When choice is demotivating. JPSP, 79(6).

• Govindarajan, V., et al. (2025). Strategic Subtraction. Harvard Business Review.

• Larsen, B., & Luna, B. (2024). Cognitive control during development. Journal of Neuroscience, 44(26).

• Taleb, N. N. (2012). Antifragile. Random House.

• Lao Tzu. Tao Te Ching, Ch. 11.

“Everything subject to origination is subject also to dissolution.” — The Buddha

An overwhelming majority of founders report experiencing anxiety, depression, or burnout in one form or another. Four times the rate of the general population. You’ve most likely been there if you’ve ever stared at the ceiling at 3am, wondering why building feels so much like dying. Creation is hard and it takes a mental toll on everyone.

Burnout is linked to chronic stress, prolonged cortisol spikes, and mental exhaustion. What if burnout was in fact caused by something even more fundamental: not grasping the laws of thermodynamics?

When it comes to chaos, do you believe your role is to reverse entropy? To fight it? To negate or neutralize it? Life itself is an act of entropy-reversion so it is tempting to view our roles as changing the very course of the universe by reversing entropy that would other be left unchecked.

Entrepreneurship is entropy-neurship. Anti-fragility is a core value of mine. Thriving on chaos, being pro-entropy, or gaining from disorder as Nassim Taleb puts it. This is definitely a powerful mindset to adopt for entrepreneurs.

But like most values, you can take it too far. Chaos is a paradox and so founders should understand the nuances of how to approach entropy, disorder and how to do so in a way that will not result in burnout—which is, in terms of thermodynamics, caused by you trying to swim against the tide of physics, causing you to deplete your stamina when you come in contact with entropy.

To sum up the scientific evidence in a single insight: The founder’s job isn’t to defeat entropy—it’s to channel it properly.

Entropy Reframed

In 1944, physicist Erwin Schrödinger asked: How does life exist when everything tends toward disorder? His answer: life doesn’t violate thermodynamics—it exploits it. Organisms import order (food, sunlight) and export disorder (heat, waste). The universe’s entropy still increases. Life just redirects where.

In 2013, MIT physicist Jeremy England took it further. His research suggests that matter naturally self-organizes to dissipate energy more efficiently. Life isn’t an accident—it’s thermodynamically inevitable. We exist not despite entropy, but because of it. We are the universe’s way of accelerating its own decay.

What does this mean for founders? Your startup is a dissipative structure. You both accelerate and reduce entropy, but the net is that you cause more entropy.

Think of Amazon: it absorbs massive energy (capital, talent, attention), transforms it (into logistics networks, cloud infrastructure, retail algorithms), and disperses it (as products, wages, warehouse labor, competitive pressure).

The order Jeff Bezos created—next-day delivery, cloud computing, the everything store—came at the cost of disorder elsewhere: Main Street retail upended, warehouse workers competing against robots, competitors bankrupted, disruption of infrastructure technologies.

Technology companies are disruptive, and disruption is definitely increasing entropy. Therefore the role of the founder is not to reverse but to channel entropic expansion to advance their mission. The question isn’t whether you’ll pay the thermodynamic cost. You do. The question is how you’ll pay it.

Unknowingly, most founders pay for it with their bodies. That’s why the majority of us feel anxious, depressed, and overwhelmed in one way or another. Handling entropy isn’t a sustainable activity and so you need to recharge your literal batteries like a phone once in a while.

The Founder’s Mind on Chaos

A 2025 study using fMRI brain imaging found that entrepreneurs’ brains literally value uncertainty differently. When shown gambles with unknown odds, entrepreneurs assessed ambiguous bets 16% above their expected value—while non-entrepreneurs discounted them. Same information, opposite valuation. The uncertainty that repels most people attracts founders.

It’s not just perception. It’s structure. The study found increased gray matter volume in the anterior insula—a region linked to risk perception and detecting risky situations—among experienced entrepreneurs. Their brains had physically adapted to processing chaos.

In 1997, Saras Sarasvathy at UVA’s Darden School discovered something unexpected while studying how expert entrepreneurs think. She gave 27 founders a 17-page problem set and recorded them thinking aloud. What she found upended conventional wisdom.

Non-entrepreneurs use causal reasoning: set a goal, gather information, predict outcomes, execute the plan. Entrepreneurs use what Sarasvathy called effectuation: start with what you have, limit downside, treat surprises as opportunities, co-create the future with partners. They don’t try to predict—they make prediction unnecessary.

The difference is profound. Causal thinkers ask: Given this goal, what resources do I need? Effectual thinkers ask: Given these resources, what goals become possible?

One approach fights uncertainty. The other makes friends with it.

Research on entrepreneurial cognition confirms founders process incomplete information differently. Robert Baron’s work on pattern recognition shows entrepreneurs “connect the dots” faster—seeing opportunity structures where others see noise. They’re not smarter. They’re wired to extract signal from chaos.

Even their neurology cooperates. Studies show entrepreneurs make decisions faster thanks to better hemispheric synergy—their left and right brain communicate more efficiently. They respond more quickly to stimuli and feel more in control under pressure.

Here’s the reframe: Founders aren’t people who absorb chaos. They’re people who see order in it that others can’t.

The high burnout rate makes more sense in that context. Founders do hard work, yes, but they’re also doing different - and taxing - cognitive work.. They’re constantly translating between the chaos they perceive as opportunity and the order everyone else needs to function. That translation is exhausting.

Complexity theorists have a term for where founders operate: the edge of chaos—the transition zone between order and disorder where innovation emerges. Too much order kills creativity. Too much chaos kills execution. Founders naturally live in the narrow band between.

Innovations rarely emerge from stable systems. They emerge from bounded instability—systems dancing at the edge. That’s where founders live. Not because they’re reckless. Because that’s where new futures get made.

Burnout as Entropic Waste

Walk into any founder gathering. Seven of eight people in that room are experiencing anxiety, depression, or burnout—

Entrepreneurs struggling with business failure show measurably elevated cortisol. Your body is literally paying the thermodynamic cost of the order you’re trying to create.

One finding offers hope: founders who set clear boundaries are three times less likely to experience severe burnout. Boundaries are entropy barriers. Without them, chaos floods into every domain of your life.

It might help to reframe those moments of burnout. You’re not weak. You’re paying the unavoidable cost of creating order in a universe that trends toward chaos. Rest is key to physically handle that chaos load, that entropy toll.

The Rigidity Paradox

“There is an immutable conflict at work in life and in business, a constant battle between peace and chaos. Neither can be mastered, but both can be influenced.” — Phil Knight, Shoe Dog

Too much entropic energy may cause you to burn out. The natural tendency for many is to increase structure, since structure is a way to transform disorder into order, isn’t it?

Yes and no. Success creates structure. Structure becomes rigidity. Rigidity kills.

The timeless pattern: You succeed → you invest in what worked → you build organizational structure around it → that structure resists change → you can’t adapt when the environment shifts → you die.

Company lifespans have collapsed from 67 years in the 1950s to a projected 15 years by the 2030s. Half of the Fortune 500 from 1999 had disappeared just ten years later.

Clayton Christensen built his career on the simple fact that “there is something about how decisions get made in successful organizations that sows the seeds of eventual failure.”

Consider Nokia and RIM. Both of them had the entire smartphone market to themselves before Apple came along. Both failed to recognize that software would matter more than hardware. The very strengths that made Nokia and RIM dominant—their hardware expertise, their carrier relationships—became the rigidities that prevented adaptation.

Nokia and RIM didn’t fail because they were stupid. They failed because they were successful. Their success created structure. Their structure became rigid. Their rigidity killed them. The entropic toll of success is real. The order you create can become the cage you die in.

Entropy Judo

The way to approach entropy is like a judo master uses the opponent’s mass and movement to throw them onto the mat. This is the concept of Wu Wei—”the art of effortless action” in practice.

“The river is not pushed from behind, nor pulled from ahead. It falls with gravity.” — Alan Watts

The river doesn’t fight the rock. It flows around it. And over time, it carves the canyon.

A startup example of this kind of judo move is what we commonly know as a “pivot”—a sharp turn in your product direction to avoid failure. Similar to a Tomoe-nage, executing a pivot needs you to channel the impending chaos and use its momentum to toss it on the mat.

Stewart Butterfield did the startup equivalent of this judo move twice. In 2002, he co-founded a company to build a multiplayer online game called Game Neverending. The game failed. They were running out of money. Apparently, as he was vomiting from the anxiety of impending bankruptcy (not all heroes wear capes), he had a realization that led to a masterful pivot.

While the main idea was tanking, a photo-sharing feature was actually working. So instead of fighting the dying game, he pivoted. That feature became Flickr. Yahoo acquired it.

Then he did it again. In 2009, Butterfield started another game company. The game Glitch launched in 2011, failed, and shut down in 2012. Worse this time: 15 consecutive failed pivots over 18 months. A tearful meeting where he laid off nearly his entire team.

But again, he noticed what was working. The internal chat tool they’d built was actually good. That tool became Slack. Salesforce bought it for $27.7 billion.

Two failed games. Two billion-dollar exits. The difference wasn’t luck—it was direction. Butterfield didn’t fight his failing games. He surfed the wreckage. He looked for and followed what was working instead of forcing what wasn’t.

I can’t wait for Stewart to start his next gaming startup.

Policies Prevent Adaptation

“We held a party to celebrate the tenth anniversary of the last time I made a decision.” — Ricardo Semler

Some founders don’t just accept entropy. They embrace it as an operating system.

In 1980, Ricardo Semler took over his father’s Brazilian manufacturing company at 21. Within days, he fired 75% of the senior executives. Then he started dismantling everything that looked like traditional management.

Semco has no job titles. No organizational chart. No headquarters. No written policies. Semler calls it “a policy of no policies.” Workers set their own schedules—not flexible schedules, their actual hours, chosen entirely by them.

Workers set their own salaries. Not suggested ranges. Their actual pay. The prediction was chaos. The reality: people generally paid themselves fairly, because they knew their colleagues would see the numbers.

Workers choose their managers. And they evaluate those managers publicly. If a manager consistently scores poorly, they’re out. Meetings are voluntary. If nobody shows up, the topic wasn’t important.

Semler himself became deliberately irrelevant. “We held a party to celebrate the tenth anniversary of the last time I made a decision.”

Semco grew from $35 million in 1990 to over $100 million by 1996. They achieved 27.5% annual growth for fourteen consecutive years.

Here’s what Semler understood: policies prevent adaptation. So Semler removed the structures that create entropy resistance. He let the system self-organize. He didn’t fight entropy—he removed everything that was fighting it.

The result: a company that adapts continuously, because nothing prevents adaptation.

The Path

While founders seem to have more tolerance and appetite for chaos and ambiguity than most, it is also important to understand that entropic resistance will cause physical damage leading to burnout, and entropic channeling requires rest and removing rigidity that prevents your adaptation.

Entropy is best approached from a place of harmony - to go along with it, not against it. Channelling entropy is not a sustainable act and it will leave your depleted - mentally, physically. This is thermodynamics and you can’t beat physics.

Entropy can be effectively channelled when best understood:

• Ask given the situation or resources, what (news) goals become possible?

• Are you channelling entropy toward a mission worth the cost?

Happy Sunday ✌🏻

Read Tao of Founders

I know this sounds backwards. Much of startup culture sits on big goals, reality distortion fields, and founders who refuse to accept limits. But a meta-analysis of 11,819 entrepreneurs found something that counters the conventional wisdom: the same psychological machinery that makes founders bold also makes them defensive. Ego is both sword and shield—and most founders can’t tell which one they’re holding.

But here’s the deeper problem: when we say “ego,” we might not even be talking about the same thing. Ego holds many various (and contradictory) views, so framing the different interpretations of ego is vital to think through the matter effectively.

The Definition No One Agrees On

Ryan Holiday’s Ego is the Enemy is the de facto startup text on the subject. It has powerful applications and this book really did a huge favour to reinvigorate Stoic philosophy by packaging timeless ideas into modern packaging. Holiday’s definition of the ego is “the enemy of what you want and of what you have.” Ego in that sense is bad, suppress it, and stay humble or you’ll cause your own demise.

But Holiday isn’t using “ego” the way Freud did.

Freud’s ego is the conscious mediator between your drives and reality—the “man on horseback” managing your instincts. In his model, ego isn’t the enemy; it’s the thing keeping you functional. Without ego, you’d be pure id—desire without restraint.

Jung went further. He saw ego as the center of consciousness, subordinate to something larger he called the Self. The problem isn’t ego itself—it’s ego inflation, when you mistake your conscious identity for the whole of who you are.

Eastern traditions take it somewhere else entirely. In Hinduism, ahamkara (”I-making”) is the false identification of your true self with impermanent things—your job title, your net worth, your reputation. Buddhism goes further: anattā means there is no fixed self at all. Ego isn’t an enemy to be fought—it’s an illusion to be seen through.

The word ego carries the weight of psychoanalysis, spirituality, pop psychology, and hot takes simultaneously.

So when Holiday says “ego is the enemy,” he explicitly isn’t talking about Freud’s ego. When Eastern traditions say “transcend ego,” they mean stop identifying with the story you tell about yourself—not stop believing in yourself.

The founder reading ego advice faces a choice they don’t know they’re making: are they trying to suppress a dangerous impulse (Holiday), calibrate a spectrum disorder (clinical), or dissolve an illusion (Eastern)?

The prescription depends entirely on which diagnosis you accept.

The Sword Ego

This is the ego we know. The one that makes you quit your job, bet your savings, and tell investors your idea will change the world. The ego that wants you to become immortal, validated by the whole world, an historical figure to be remembered for centuries.

Research confirms this type of ego-centric energy works—at least initially. The meta-analysis found that narcissism correlates positively with entrepreneurial intention (rc = 0.24). People with high ego try to start things. They take swings others won’t take. They have to believe they can do exceptional things to want to take the jump.

VCs have learned to pattern-match for this. The “reality distortion field” isn’t a bug—it’s a feature they’re selecting for. The confidence to walk into a room and pitch something that doesn’t exist yet. The self-belief that lets you ignore the 90% failure rate and assume you’ll be the exception. Maybe all of invention and progress relies on some degree of “big ego energy” in order to imagine and achieve anything new.

The assumption underlying all of this: ego equals boldness equals good, as long as it’s channeled properly. Ego can be a force for good, not the enemy—and that’s a paradox I frankly struggle to harness as a founder.

But there’s a version of ego we don’t discuss much—and it might be the more dangerous one.

The Ego Shield

In a study of crowdfunding entrepreneurs, researchers found that the more narcissistic founders set lower goals and longer timelines than their less narcissistic peers. Let that sink in. The high-ego founders weren’t swinging for the fences. They were playing it safe.

The mechanism is ego-protection. If you set a goal you can’t fail to hit, you protect your self-image from public rejection. If you give yourself extra time, you build in excuses. What looks like “being realistic” or “conservative planning” may actually be higher ego, not lower—it’s armor against the possibility of falling short where everyone can see.

Clinical psychology has a name for this: vulnerable narcissism—the hypersensitive, status-protecting variety that looks like introversion but is driven by the same entitlement as its grandiose cousin. The grandiose narcissist attacks. The vulnerable narcissist withdraws. But beneath both: the same contempt-proneness, the same entitlement, the same antagonism.

The crowdfunding study had a punchline. Backers detected this pattern and funded these founders less. The market sees through armor. People sense when someone is playing defense instead of offense—even when that person doesn’t sense it themselves.

Going 0 → 1 Rewards Ego

Recent research suggests ego isn’t uniformly good or bad—it depends on when. A 2024 study put it this way:

“Narcissism is a tw-sided sword for founders. In the early stages of a company, many of the founder’s tasks can benefit from narcissistic tendencies. In the later stages of a company, that might shift to overwhelmingly negative effects.”

The 0→1 phase—ideation, founding, early fundraising—rewards ego. You need unreasonable self-belief to start something from nothing. You need to project confidence before you have evidence. You need to convince people to join a company that might not exist in a year.

Conversely, the 1→100 phase—scaling, managing, iterating—punishes it. You need to listen to customers who tell you your product is wrong. You need to hire people smarter than you and actually let them do their jobs. You need to kill your darlings when the data says so.

The trait that makes you start the company makes you unsuited to run it. Very few founders end up the CEO of a public company.

Narcissism correlates with passion for inventing but not passion for scaling. The visionary founder archetype—brilliant at creation, terrible at operations—isn’t a personality quirk. It’s a predictable consequence of the same psychological machinery.

A systematic review found that “while narcissism makes potential entrepreneurs have higher entrepreneurial intentions and greater willingness to take risks, it also prevents entrepreneurs from discovering opportunities, acquiring resources, and learning from failure.”

What gets you here won’t get you there.

Want to Fund My Big Ego?

A team analyzed the crowdfunding outcomes of entrepreneurs they ranked on a narcissism scale.

• Low narcissism: underfunded. The founders didn’t project enough confidence to attract backers.

• High narcissism: also underfunded. The founders projected so much confidence that it repelled people—or they’d set defensive goals that signaled weakness.

• The sweet spot was in the middle.

This is the calibration problem. There’s an optimal zone, but it’s not at either extreme. Too little ego and you never start. Too much ego and you can’t course-correct when reality pushes back.

Multiple wisdom traditions arrived at the same place through different routes:

• Confucius: “To go beyond is as wrong as to fall short”

• Aristotle: The golden mean; virtue as balance between excess and deficiency

• Stoicism: Humility without self-abnegation; confidence without arrogance

• Clinical psychology: Healthy narcissism—adequate self-love, not too little, not too much

• Taoism: Balance of opposites; the middle way as dynamic equilibrium

The Visibility Problem

The symptom of too much ego is not being able to see you have too much ego. This is the fundamental challenge. You can’t use a broken instrument to measure whether the instrument is broken.

This is perhaps the only point on ego where all traditions converge:

• Jung: Ego inflation is “narcissistic delusion that the ego is the self”—you don’t see it because you’re inside it

• Buddhism: The illusion feels like reality; you can’t see the prison from inside the prison

• Tolle: “Awareness and ego cannot coexist”—the ego hides when observed

• Clinical psychology: Narcissistic grandiosity correlates with unrealistic self-assessment

• Stoicism: Marcus Aurelius constantly warned himself against becoming “another Caesar”—he knew visibility required vigilance

The usual narrative told on Steve Jobs casts him as proof that massive ego works—the reality distortion field, the perfectionism, the impossible demands. But the overlooked chapter tells a different story.

Jobs was publicly fired from Apple in 1985, by the board he’d helped create, from the company he’d co-founded. This wasn’t a strategic transition. It was a humiliation.

The years that followed—NeXT, Pixar—weren’t exile. They were recalibration. Jobs learned to work with teams differently at Pixar. He learned to build organizations, not just products. When he returned to Apple in 1997, something had shifted. The ego was still there—you don’t launch the iPod without ego—but it was channeled differently. Calibrated.

When Jobs gave his famous Stanford commencement speech, he delivered the line we all remember: “Stay hungry, stay foolish.” But listen to the context. He said it after describing his lowest moment, after being publicly rejected by the company he’d built. It wasn’t a prescription for ambition. It was a prescription for humility. Stay in beginner’s mind. Don’t assume you know everything.

Engineered Humility

Ed Catmull built something different at Pixar. Jobs clearly did learn from that approach.

“Sometimes, magic happens. And by magic, I mean the ego has left the room.” - Ed Catmull

But Catmull didn’t just hope for humble people. He built systems that neutralized ego:

• The Brain Trust: Senior creatives critique each other’s films—with no authority to mandate changes. This removes power structure from feedback. You can hear what’s wrong without someone forcing you to fix it, which makes you actually listen.

• Hiring smarter: “He was more qualified for my job than I was... I felt this fear—if I hire this guy, my boss will realize.” But Catmull hired him anyway. That hire became Pixar’s co-founder.

• Power dynamics: “If a powerful person talks, they’re setting the tone in the room. And we don’t want them to set the tone.” So powerful people speak last.

The result: 22 films, 15 Academy Awards, $14 billion-plus box office. The most consistently successful creative studio in history.

This is what ego calibration looks like when it’s systematized.

The Echoism Trap

We’ve spent most of our time on too much ego. But the inverted U has a left side too.

Clinical psychology has a name for deficient ego: echoism—the Echo to Narcissus. Where narcissists take up too much space, echoists disappear. They dissolve themselves into others’ needs until there’s no self left to lead.

What does too little ego look like in founders? Never starting because surely someone else smarter must have tried already. It looks like burnout, self-sacrifice without boundaries. It looks like accepting bad advice because you don’t trust yourself and your gut.

Eastern traditions warn about this too. “Non-attachment” misunderstood becomes self-abnegation. The Bhagavad Gita doesn’t advise Arjuna to stop acting—it advises acting without attachment to outcome. Too little ego isn’t spiritual attainment; it’s a different kind of trap.

Walt Disney was fired from a newspaper job. His editor’s remarks: “You lack imagination and have no good ideas.” His first animation company failed completely, leaving him broke.

Disney didn’t reframe rejection as “they don’t understand my vision” (grandiose). He didn’t quit to protect his self-image (defensive). He absorbed rejection without it destroying his self-worth or inflating his ego into defensiveness. Same story for Edison and Dyson. Any good inventor has to clearly see their work as independent from their own self-worth to make meaningful progress in spite of burning, continuous failure.

This isn’t ego-as-sword (attacking). It’s not ego-as-shield (avoiding). It’s something else: persistence without attachment. Acting without needing validation or avoiding rejection.

Awareness as the Path

Ego isn’t a duality, it isn’t good or bad. Ego is a tool: a sword and a shield.

The question isn’t “do I have too much ego?” You can’t answer that accurately—by definition, excess ego distorts self-assessment. The real question is: what tool am I using right now?

The founder wielding ego as sword is taking risks, attacking markets, betting on vision. They’re making asks they’re not sure they’ve earned. They’re building something that might not work, in public, where failure is visible.

The founder wielding ego as shield is setting safe goals, avoiding feedback, protecting self-image from the possibility of falling short. They’re staying in comfortable positions because stretching would mean risking exposure. They’re calling it realism.

The calibrated founder isn’t ego-less. That’s not the goal and probably isn’t possible anyway. The calibrated founder is ego-driven too. And simply aware that their ego will always lead to blind spots. They’ve built systems—people, practices, feedback loops—that tell them what they can’t see themselves.

Ego is mostly invisible to us. We all tend to think we have less ego than we actually do. The best way to know how much ego we really do project is to ask others what they really think—if you can stomach it.

Founders roll through dozens of decisions each day. Your role demands that you spend hours evaluating, comparing, and deciding what is best for you and your startup. The quality of those decisions ultimately determines the quality of your work.

Decisions and Trade-offs

Decisions require you to judge and to establish preferences. You apply a form of judgment on everything you do: hiring, building products, writing emails, communicating priorities with your team, and so on.

Good decisions are about making good trade-offs: what to keep, what to discard, what’s important, what to ignore. Good decisions command you to define mental shortcuts, also known as heuristics, that will help you move forward without too much effort.

Good decisions and good trade-offs boil down to focus. You don’t need to have the full picture if you can focus on the most important things. In fact, you’ll likely never have the full picture before making a decision. Jeff Bezos looks for 70 percent certainty in order to make most decisions. That is the trade-off Amazon is willing to make with most decisions, embracing speed and learning over completeness.

The Risk of Harsh Judgment

Good decisions usually demand you reach a conclusion based on your imperfect information, imperfect judgment, and imperfect timing. Dealing with a constant stream of decisions each day, small and large, made with incomplete information, invites a new habit to form in your mind: you tend to jump to conclusions.

Jumping ahead is good from a decision speed and agility viewpoint. However, jumping to conclusions as a habit can encourage you to judge readily, sometimes harshly.

I’ve definitely noticed that pattern getting stronger in my mind as my founder journey goes on. With each decision piling up through the years, I feel, well, judgier. By trying to decide faster, I sometimes forget to suspend my own preconceptions. Past a certain point, I stop listening with the intent to understand; rather, I listen to confirm my decision. I haven’t always listened as well as I should have. Listening closely to customers, employees, and partners is probably the lifeline of entrepreneurs, a prerequisite to doing anything of value. Judging harshly makes it so much harder to see the finer nuances of reality as it is. It took me a while to learn how judgment creates separation.

Judgment and Relationships

Many of us are quick to judge, yet we don’t want to be judged by others. Imagine the last time someone judged you mistakenly because they had imperfect information. Maybe they jumped to conclusions or failed to give you the benefit of the doubt. How did that make you feel? No one enjoys feeling judged unfairly.

Harsh judgment can be very damaging to relationships. The moment someone feels judged harshly by someone else, two things will likely happen. Either the person being judged agrees with the judgment and feels shame, or they disagree with the judgment and feel anger. There are no scenarios I can think of where harsh judgment leads to a positive interaction.

As therapist, author, and Buddhist teacher Tara Brach explains:

“Judgment is when we’re making others bad. The deal is, as far as I can tell, we get accustomed to it. We get accustomed to demoting people in our minds and in our hearts. We get accustomed to the distance it creates.”

For a founder, judging people from a place of “bad others” can be devastating to your team. Constant judging will soon turn to blame. It will be felt and heard by your colleagues and your loved ones. Feeling judged, or avoiding being judged, shuts people down. Judgment prevents them from doing their best work because they fear blame and shame.

Pixar’s Braintrust

In Creativity, Inc., Ed Catmull, co-founder of Pixar, explains how fear of judgment hindered creativity. Employees hesitated to share ideas because they feared negative judgment. Pixar shifted the focus from critiquing the person to evaluating the idea itself. This subtle change fostered a more open and creative environment, where team members could share and explore unproven ideas without fear. Debate the ideas, not the people.

“People hasten to judge in order not to be judged themselves.”

— Albert Camus

The Weight of Harsh Judgment

Over time, harsh judgment builds into an emotional burden. This negative energy dampens your spirit. Judgment accidentally trains the mind to be rigid. The more you believe you know, the harder you become to satisfy. With this mindset, you think no one else can match your standards. You end up intolerant and exhausted.

This same rigidity almost hindered Patagonia’s mission. Founder Yvon Chouinard judged employees harshly for not sharing his passion for sustainability. Turnover was high. Over time, he learned to balance discernment with tolerance, educating rather than blaming. That shift built Patagonia’s enduring culture of inclusion and activism.

From Harsh Judgment to Wise Discernment

Harsh judgment separates. Wise discernment connects. Discernment notices without condemning. It keeps empathy, compassion, and open-mindedness intact.

The Zen story of the two monks captures it best. One monk carried a woman across a river, breaking a rule. Hours later, the younger monk judged him. The elder replied: “I left the woman by the river’s edge. Yet you still carry her in your mind.”

Judge Kindly

“We can never judge the lives of others, because each person knows only their own pain and renunciation. It’s one thing to feel that you are on the right path, but it’s another to think that yours is the only path.”

— Paulo Coelho

Read Tao of Founders

On Vision & Execution

“Don’t undertake a project unless it is manifestly important and nearly impossible.” — Edwin Land, Founder of Polaroid

Land possessed an extraordinary capacity for mental visualization—an ability to see entire complex systems in his mind before building them. With over 500 patents to his name, he embodied a rare fusion of scientific genius, artistic sensitivity, and philosophical depth.

→ Read more

A fearless mind free from expecting results is a powerful combination: this is the mindset of someone with nothing to lose. What would you keep doing even if failure was assured?

Outstanding founders believe their success is inevitable, while expecting—even relishing—failures and adversity along the way. If you can find true inner motivation regardless of success or failure, then nothing can stand in your way.

→ Read mo

“You always start with a fantasy. Part of the fantasy technique is to visualize something as perfect. Then with the experiments you work back from the fantasy to reality, hacking away at the components.” — Edwin Land

This “work backwards” approach—starting with the ideal end state—lets you clearly visualize what you want and track whether you’re moving closer to your goal. Jeff Bezos likely took a page from Land’s book.

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“My whole life has been spent trying to teach people that intense concentration for hour after hour can bring out in people resources they didn’t know they had.” — Edwin Land

During critical development phases, colleagues reported Land would work for 72 hours straight while maintaining peak cognitive function. More importantly, he modeled a behavior that led his employees to also behave with extreme focus.

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On Design & Taste

Beauty coordinates human cognition and social organization. It reduces physiological stress, freeing mental resources for complex tasks. It restores attention that demanding work depletes. And—most importantly—it synchronizes emotional states across groups, enabling collective action.

When we remove roads, society visibly breaks down. When we remove aesthetic infrastructure, society breaks down in diffuse ways we’ve learned to ignore.

→ Read more

The most common founding motivation isn’t ‘I spotted a market inefficiency.’ It’s ‘I experienced something ugly and felt compelled to replace it with something beautiful.’

Jobs was offended by ugly computers. Dyson was aesthetically bothered by inelegant solutions. Chesky wanted travel to feel humane. The aesthetic violation came first; the business case came later. This is founding as aesthetic protest.

→ Read more

Bureaucratic, extractive, inhuman systems don’t emerge because evil people design them—mostly. Most emerge because no one insisted on a ‘not-shitty-experience’. It’s our role as entrepreneurs to revolt aesthetically against ugly products, services and systems.

Only entrepreneurs have the freedom and incentives to ask: “But is it beautiful? Is it humane? Is this how things should work?” If founders don’t insist on good taste, who will?

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On Curiosity

“The noblest pleasure is the joy of understanding.” — Leonardo da Vinci

Leonardo’s driving force was an insatiable curiosity—a need to understand everything about the world around him. He didn’t fight his curiosity—he weaponized it.

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“He saw beauty in both art and engineering, and his ability to combine them was what made him a genius.” — Steve Jobs, on Leonardo da Vinci

It’s very powerful for creatives to master art and science. Having range produces more and better ideas.

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The best things have no exit plans. They just keep becoming. Your startup will end. Your product will be replaced. Your technology will be obsolete. But the questions you ask, the connections you make, the possibilities you open—these can echo through centuries.

Leonardo’s legacy may not be in what he finished, but in what he began. His “failed” flying machines laid groundwork for aviation. His “abandoned” engineering projects presaged modern hydraulics, optics, and robotics. Perhaps his biggest contribution was finding and asking questions worth asking for many generations.

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On Commitment & Differentiation

“The best you could say for it was that it was lonely and painful. But as I started to win by greater and greater margins I did it more and more, because I knew the reason for my success was that out on the sand dunes I was doing something that no one else was doing. Difference itself was making me come first.” — James Dyson

Stand out by zeroing in on the few things others can’t or won’t do. Total commitment unlocks cognitive resources normally wasted on backup planning.

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“What I’ve learned from running is that the time to push hard is when you’re hurting like crazy and you want to give up. The moment you should accelerate is the moment you’re the most tired. Success is often just around the corner.” — James Dyson

Persistence and knowing when to push harder despite exhaustion distinguishes those who succeed from those who give up just before breakthrough.

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“Business marries you, you sleep with it, eat with it, think about it much of your time. It is in a very real sense an act of love. If it isn’t an act of love, it’s merely work, not business.” — Estée Lauder

The level of commitment needed to build something significant cannot be sustained without genuine love for the work itself.

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70% commitment yields only 20% chance of success, while 100% commitment jumps to 75% probability.

This isn’t motivational rhetoric but empirical fact. Partial commitment creates partial results. Go All-In.

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On Focus & Intention

“When you focus by saying no to something, you experience a mini-death: you say goodbye to a relationship, an idea, an expectation somewhere down in the future. It sucks to grieve. But actively grieving makes room for you to grow into your higher potential.”

Focus isn’t an intellectual problem—otherwise you’d have solved it already. The emotional drivers that hinder focus overpower conscious thought. Focus is an emotional skill disguised as an intellectual one.

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“Focus means saying no to something with every bone in your body screaming yes.” — Steve Jobs

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“I have always believed that if you stick to a thought and carefully avoid distraction along the way, you can fulfill a dream. My whole life has been about fulfilling dreams. I kept my eye on the target whatever that target was.” — Estée Lauder

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“What I do better than anything else is cut out distractions. If a system isn’t working efficiently, I can see where it’s jammed, eliminate the problem, and find a way to keep everything moving forward.” — Paul Van Doren, Founder of Vans

An organization’s focus rests on its leader’s ability to focus.

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“With time, your ability rises to the level of your intentions. If you focus only on what you perceive as feasible today, you end up selling yourself short in the future.”

James Cameron worked on Avatar for 15 years, deliberately choosing projects that push boundaries. By being highly intentional, he embraces the discomfort of monumental tasks that scare other directors away.

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“Goals can make you greedy. Perhaps the biggest downside of chasing your goals is how difficult it is to stop the goalpost from moving after you reach the initial target. While humans innately seek to push our limits, a sense of having and being enough is the highest form of wealth one can have.”

Don’t use goals to escape from a today you wish was entirely different. Create goals that start with your current reality, and build with it.

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On Failure & Resilience

The Stockdale Paradox: holding high and low expectations simultaneously.

Soldier James Stockdale observed that the most optimistic prisoners often fared the worst. Outstanding founders believe their success is inevitable, while expecting—even relishing—failures along the way.

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“Failure is not something that happens at one point in time. Failure is a door. To me failing feels like stepping out of a room, and into a new one. There is continuity with failure; the end of something always means the start of something else.”

Anything worth doing requires doing things wrong first to learn to do them correctly eventually.

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“Just because something doesn’t do what you planned it to do doesn’t mean it’s useless.”

Post-it notes, microwaves, Viagra, Play-Doh—many modern inventions were initially intended to solve another problem. Edison was keen to challenge his own flawed assumptions.

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You overestimate how bad failure will feel and how long it will hurt.

People systematically overestimate the intensity and duration of negative emotions from bad outcomes. Founders who understand this can take bigger risks knowing recovery is faster than anticipated.

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On Identity & Purpose

“I am also all of what I’ve lost.”

Paul Van Doren reflected on outliving his wife, friends, and business partners. Your success won’t shield you from loss. What remains isn’t just what you built—but who you became in the process.

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“Imagine you are building a Jenga tower: the higher you stack expectations, the more unstable your identity becomes as a whole.”

The higher the expectations you place on yourself, the harder it becomes to experience satisfaction in who you are at this moment.

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“No dream is as great as the person you might become by remaining true to it.”

The best goals center on becoming, not doing or having. The most rewarding aspects of reaching your goal lie in your chance at improving, each step of the way.

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“How you climb a mountain is more important than reaching the top.”

— Yvon Chouinard

This philosophy shaped Patagonia’s most consequential decisions, from choosing ethical manufacturing partners to rejecting shortcuts that boost short-term profits.

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10,000 Iterations

You’ve likely heard that it takes 10,000 hours of practice to become a world-class expert in your field of choice. This idea was originally shared by Malcolm Gladwell in his book Outliers: The Story of Success.

Although the 10,000 hours theory makes sense, people tend to miss the real point of it. The amount of time you put in counts less than the quality of each hour of work you put in. What you do during those hours is what truly matters.

Iterations Over Hours

When it comes to mastering the craft of entrepreneurship, I’ve found that 10,000 iterations is a better measure of progress than 10,000 hours.

Thomas Edison iterated over 10,000 prototypes of various inventions—and holds a record 1,093 patents under his name. Those patents include the phonograph, the electric lightbulb, and the storage battery.

James Dyson iterated over 5,000 prototypes before launching his first bagless vacuum cleaner. The Wright brothers’ first airplane, James Dewar’s Thermos flask, Graham Bell’s telephone, and Edwin Land’s instant camera each required over 1,000 iterations before gaining mass appeal.

Most iterations do not produce genuine breakthroughs. They provide subtle and marginal improvements. Still, those small changes compound as you spend time learning your field of choice, guided by a trial-and-error process, pushing the boundary of your expertise, year after year.

Craftsmanship Is Inefficient

Some aspects of your life can and should be approached with maximal efficiency, like managing email. But when it comes to developing your craft, efficiency is not the way to go. There are no shortcuts.

Real craftsmanship requires the inefficiency of iterations. Craftsmanship is inefficient because there are no paved routes to get to the very top in terms of quality and excellence—just like you can’t just drive your car up Mount Everest.

Craftsmanship, by definition, cannot be mass-produced. You have to earn your craft. This is the case for mastering any field, whether you are a Swiss watchmaker, an Olympic athlete, or an entrepreneur.

In other words, you can’t just clock in your 10,000 hours as efficiently as possible and passively expect greatness. This is not math. You can’t compensate for sloppy work by doing more of it. Deliberate and tedious practice is what actually helps you improve.

Paradoxically, you get better faster by relishing the hard and boring work while others are looking for shortcuts. Very few people have the mindset to keep doing just one thing, fully dedicated to their craft, for 10 years or more.

Patience will always be in short supply. But with enough time, even the smallest of improvements stack up to tangible breakthroughs. As a craftsman, as a maker, doing the inefficient work is what sets you up for what isn’t attainable today.

“What you choose to work on, and who you choose to work with, are far more important than how hard you work.”

— Naval Ravikant

Focus Compounds

For those driven by craftsmanship, the privilege to work on meaningful and creative challenges, with trusted friends inspiring/pushing each other is entrepreneurship’s greatest reward. Once you know your direction, and who to go with, then it all comes down to focus—applying time, effort, and deep care toward reaching your dream.

People are much better at thinking linearly than thinking exponentially (calculus, a branch of mathematics covering exponentials, happens to be the high school subject with the highest failure rate). Consistent focus is an advantage hidden in plain sight.

It is immensely challenging to focus on just one thing and stick to it for years while the world around you is screaming for your attention. Most people quit too soon because they get discouraged or bored; they change their priorities midcourse, mistakenly thinking their approach is not working. But all they had to do was keep focused long enough to let the compounding work.

Getting results always seems to take longer than imagined. But that’s not a reason to stop.

“The first rule of compounding: Never interrupt it unnecessarily.”

— Charlie Munger

The Tale of the Clever Girl and the Greedy Raja

In a small Indian village, a clever young girl found herself facing a greedy raja during a time of famine. The raja was hoarding all the city’s rice reserves, unwilling to help his people.

As a way to save the people around her, the young girl asked the raja for just one grain of rice, doubled each day, for 30 days. The raja agreed without hesitation.

As the days passed, the raja began to realize what he’d gotten into. By the end of the month, the exponential growth of the rice amounted to 77 tons, emptying his reserves.

The wise girl understood the power of compounding and ensured that the people received the food they needed.

This tale shows how difficult it is for the human mind to grasp the sheer power of exponential forces, and just how powerful a daily streak can become with enough time. Consistent focus is the magic ingredient of - a compounding force.

The Five-Hour Rule

An uninterrupted daily streak is all it takes for compounding to take off, assuming you persist long enough to get results. Getting the benefits of consistency is about making the time, usually three to five hours, to focus on the hardest and most creative part of your job—and to prioritize it every day.

Productivity researcher Anders Ericsson found that the top performers in various fields seem to max out at three to five hours of creative work daily. For example, he notes that many established authors “tend to write only 4 hours per day, leaving the rest of the day for rest and recuperation.” He also found that the top violinists at a prestigious music college practiced, on average, 3.5 hours per day.

Meaningful creative work is tiring. Because of the intense concentration needed for creative work, I usually run out of mental fuel before I run out of time. When you’re doing something challenging, it is better to manage your energy than your time.

Feeling tired, unmotivated, or distracted is also part of the course. Expect it. Plan for it.

Five hours leaves room for distractions to come up during the rest of your day, because whether important or trivial, some random things will undoubtedly demand your attention. Give yourself a buffer, a dedicated time to be less effective. Block out those five hours, then leave the remainder of your day for whatever else that comes up.

You can’t do five hours? No problem—start small and work your way up. As Greg McKeown, author of Essentialism: The Disciplined Pursuit of Less suggests, block out two hours to work on a single goal. Use this time to work on your most important priority for the day, the month, the year. If needed, start with as little as 15 minutes. Just start blocking time and aim to expand. Just. Start.

In the context of entrepreneurship, five hours of creative work can look like coding, designing a new product, talking to customers, or researching your market for insights.

Internal meetings are generally useless for creative work, but they can help organize teams to work better. In general, I find that meetings do not have the same creative output as asynchronous, hands-on tasks. There are always exceptions of course, but usually deep creativity aligns with solitude and clarity of mind.

Many creative masters have embraced their own version of the five-hour rule. Stephen King writes around five hours per day, as does J. K. Rowling. Jerry Seinfeld too. Arnold Schwarzenegger trained as a bodybuilder for five hours per day, and later trained to become an actor for five hours per day. Leonardo da Vinci, Paul Graham, Winston Churchill—the list goes on.

“Intense concentration…can bring out resources in people that they didn’t know they had.”

— Edwin Land

Consistency and Trusting Your Process

Believing in your creative process is a key ingredient for consistency and focus. The initial period, when you start putting in effort but have yet to see any results, is going to test your resolve. That is true especially when you’re creating something never done before.

Although you never know how new things will turn out, consistency inevitably speaks for itself. Sticking with the process is what makes you creative. The more you believe this statement is true, that your success is unavoidable and solely a matter of time provided you focus consistently well, the more likely you are to stick to your goals.

Trust the creative process and it will guide you.

Also, choosing consistent focus over hard grind also means you can relax for the same result. You’re going to do and feel a lot better when you enjoy the journey instead of straining so much.

“I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.”

— Bruce Lee

Happy Sunday ✌🏼🎄

Read Tao of Founders

Now that we’ve explored the psychology of beauty and how good taste and design are core to a functioning society—not accessory—let’s bring it home by talking about beauty, taste and design in the context of entrepreneurship.

This last part explores the WHY and HOW of pursuing beauty and good design in all aspects of entrepreneurship with evidence-based insights.

The pursuit of beauty is itself a core entrepreneurial driver—as fundamental as the desire to solve hard problems or grow as a person. It’s not decoration on top of ambition. It is its own form of ambition.

A 2025 study from Lund University found that founders who scored high in aesthetic sensitivity were far more likely to pursue mission-driven ventures. Not slightly more likely—dramatically more likely. Beauty wasn’t their branding strategy. It was their selection criteria for what problems were worth solving.

A 2023 European study on “design authorship” found that designer-founders typically start companies to materialize a personal creative vision—not to maximize financial returns. Research on creative entrepreneurs found the same dynamic: creative founders consistently ranked aesthetic integrity and craft above profit maximization.

Beauty is a form of intrinsic motivator and north star that guides them towards their grand vision. When the work itself is rewarding—when refining the solution generates its own satisfaction—motivation becomes self-sustaining. You’re not drawing down willpower. You’re tapping into something that replenishes itself.

“Once you have tasted flight, you will forever walk the earth with your eyes turned skyward, for there you have been, and there you will always long to return.”
— Leonardo da Vinci

Research on aesthetic openness shows that people high in this trait experience a dopaminergic response when encountering or creating harmonious patterns. For these founders, the refinement loop is pleasurable. Tuning a feature until it feels right. Rewriting copy until it clicks. Reworking a brand system until it achieves coherence. These aren’t costs to minimize—they’re intrinsically rewarding, like playing music or solving an interesting puzzle.

This changes the economics of persistence. The founder who finds refinement tedious spends willpower with every iteration. The founder who finds refinement pleasurable generates energy. Over multi-year timescales, this difference compounds dramatically. The most impactful, driven founders are building something that will outlive them, chasing elegance using a form of aesthetic obsession: Jobs, Edwin Land, Dyson, Chesky. Those founders directly and openly attacked the status quo using aesthetic obsession to drive bold, innovative and meaningful designs.

Taste as Perception, Not Preference

As I said, taste is known to be entirely subjective. Beauty is seen as preference. However as we have seen from scientific insights from our brains and collective stance on beauty, beauty might be subjective, but it does serve an objective, real evolutionary function. The research tells us that taste is a cognitive resolution enhancer. It literally helps you see more of reality.

A study from the University of Liège put serial entrepreneurs in fMRI machines and found distinctive neural connectivity patterns. Compared to managers, successful founders showed stronger connections between regions associated with cognitive flexibility (the right insula) and exploratory decision-making (the anterior prefrontal cortex). The researchers interpreted this as enhanced ability to toggle between exploring new possibilities and exploiting what works.

But notice what this neural architecture also enables: aesthetic judgment. The same circuitry that lets founders flexibly consider multiple options is the circuitry involved in perceiving patterns, recognizing elegance, and sensing when something “fits.” Aesthetic sensitivity and entrepreneurial cognition aren’t separate capabilities—they share neural substrate.

This is why Harvard Business Review’s work on “aesthetic intelligence” matters for founders: leaders who can sense when something no longer looks or feels right in their product, brand, or environment are detecting problems earlier. Sensitivity to aesthetic violations functions as early warning for deeper issues—cluttered flows, “Frankenstein” UI, incoherent features, off-brand behaviour, messaging drift.

Good design is high-fidelity information compression: it filters noise and presents signal in an intuitively graspable form. When a founder says “this feels elegant,” they’re often recognizing—subconsciously—that the model compresses a complex reality correctly. When something feels “off,” that’s often your brain detecting a mismatch between the model and reality before you can articulate why.

Beauty operates as a diagnostic tool for entropy. Systems often become ugly and messy before they become a real problem. The founder who can see these patterns has a perceptual advantage unavailable to the one who only reads dashboards.

This also explains why research on highly sensitive persons found that high-sensitivity individuals performed equally or better than typical entrepreneurs in opportunity recognition. Emotional and aesthetic sensitivity isn’t a liability—it enhances pattern detection. The same attunement that makes someone notice a slightly off colour palette makes them notice a slightly off market signal.

Enough With Ugly Experiences!

When you look at what many legendary founders describe as their founding moment, it came from aesthetic offense. They encountered something ugly—a clunky process, an inhuman interface, a graceless experience—and they just couldn’t tolerate it.

Jobs talked about being offended by the ugliness of existing computers. Dyson was aesthetically bothered by an inelegant solution. Chesky wanted travel to feel like something other than a sterile transaction. Whitney Wolfe Herd built Bumble because the existing dating experience felt degrading. Brian Armstrong started Coinbase because sending money internationally felt absurdly clunky for the digital age.

These weren’t primarily efficiency arguments. “This is ugly” preceded “this could be 10% more efficient.” The aesthetic violation came first; the business case came later.

The most common founding motivation isn’t “I spotted a market inefficiency.” It’s “I experienced something ugly and felt compelled to replace it with something beautiful.”

This is founding as aesthetic protest. The bureaucratic, clunky, inhuman systems that accumulate in mature industries aren’t just inefficient—they’re offensive to people with developed taste.

In their minds, the founders who build genuinely new categories aren’t attacking competitors, cornering the market and disrupting incumbents. They’re proposing a new aesthetic standard for how things should work. They’re saying: “Here’s what good looks like in this domain”—and the market reorganizes around that vision. Taste is a clear and comprehensive vision of how things should be.

There’s also a structural reason this matters beyond motivation. Beautiful systems degrade gracefully; ugly systems accumulate “design debt” and collapse under complexity. Across architecture, software, and biology, systems with fewer arbitrary exceptions and cleaner forms are easier to scale and maintain.

Think about what this means practically. A product with coherent design principles can absorb new features without becoming a Frankenstein. A company with aesthetic coherence in its culture—how decks look, how meetings run, how people talk to customers—can scale without losing its identity. An ugly system, by contrast, accumulates exceptions, workarounds, and special cases until the complexity becomes unmanageable. That’s why the simpler designs seem to win every time.

In fact, You can assess anti-fragility simply by looking at aesthetic coherence. Beauty is structural resilience.

Why is taste-as-a-skill so under-appreciated?

If beauty is this valuable, why isn’t everyone already investing in it? Perhaps biases explain why aesthetics remain a mispriced opportunity for those who developed good taste.

STEM training generally devalues beauty. Engineering education frames aesthetics as “nice-to-have”—something you add after functional requirements, if there’s time. It’s not treated as a variable in trust, perceived quality, or cognitive load. Yet research on product perception shows that aesthetics significantly shifts how people assess performance and reliability. Users judge well-designed products as more trustworthy and competent—before they’ve even used them.

MBA training ignores it. I was that person. Business education focuses mostly on quantifiables: CAC, LTV, unit economics. But customers choose primarily based on how offerings make them feel. Metrics tell you nothing about how a customer thinks and decides. Spicy take: “you can’t manage what you don’t measure” is bullshit. Numbers have a place sure, but qualitative data is actionable data.

Startup culture tends to overlook it. Lean startup and MVP culture have pushed us to ship early and ship ugly. Scrappy can be helpful, but as we’ve seen, beauty scales better while ugly is confusing and complex to users—sometimes that triggers a visceral negative response in them.

“Ugly but working” is celebrated as scrappy pragmatism. Polish is dismissed as vanity. Studies on product aesthetics demonstrate that form heavily shapes perceived function, trust, and willingness-to-pay.

Taste is actually a capability that sharpens with intentional practice. Research on aesthetic education shows that exposure to aesthetic training enhances creativity, adaptability, and entrepreneurial capability.

Treat your environment as curriculum. Work with well-designed tools, spend time in beautiful spaces, study products and brands with strong aesthetics. The architect Christopher Alexander argued that harmony with your surroundings creates inner coherence and better design judgment. Your inputs shape your outputs.

So much of being a great founder comes down to how you design the environment for your team, your customers, yourself to flourish. A bad environment (bad system) will beat a good founder every time.

Develop aesthetic intelligence deliberately. Keep a swipe file of interfaces and objects you find beautiful. It really comes down to looking. Beauty can be found in anything, if you know how to look for it.

Good design skills and principles transcend any individual field. Simply explore what makes something great, better than the other products and alternatives. This is the starting point for understanding what makes a good design. From experience: great designs tend to be universal in nature. The design is beautiful when you zoom in and when you zoom out. It looks just as gorgeous from inside as outside.

“When you’re a carpenter making a beautiful chest of drawers, you’re not going to use a piece of plywood on the back, even though it faces the wall and nobody will ever see it. You’ll know it’s there, so you’re going to use a beautiful piece of wood on the back. For you to sleep well at night, the aesthetic, the quality, has to be carried all the way through.” — Steve Jobs

Research on functional diversity shows that teams combining design, engineering, and business backgrounds outperform homogeneous groups. The same applies to individuals. The founder who understands typography, knows why certain code architectures are elegant, and can feel when a business model has too many moving parts has more aesthetic bandwidth than the specialist who only knows one domain. Seeing beauty is a lot about pattern recognition, and so being a generalist across domains is helpful to connect various, seemingly unrelated patterns. That is where innovative insights come from usually—your fresh-yet-informed perspective.

The Founder’s Ethical Dilemma

Here’s where I wanted to end this 3-part piece on the psychology of good taste. The imperative of good design goes way beyond beauty. Good design is also about doing the right thing for everyone.

Good design is positive sum. It refuses predatory patterns in product: dark user patterns, addiction loops, deceptive layouts. For all its glory, the internet and AI still have a long way to go to be well-designed for humans. In fact the internet traffic is a majority of bots, so humans might not even be the center of the experience after all!

Beautiful, humane products respect users rather than extract from them. Research on moral elevation shows that exposure to ethical beauty—witnessing virtue, experiencing humane design—actually increases prosocial behaviour. Feelings of beauty are more intense when shared with others, prompting others to further seek and appreciate beauty, further reinforcing pro-social bonds. Ethical beauty proves to us that there is goodness in others, further building trust within communities.

If entrepreneurs don’t insist on good taste, who will?

Managers tend to optimize for efficiency (and their reputation) within existing constraints. Their job is to hit metrics and deliver or exceed high expectations, not question whether the metrics are worth hitting in the first place. To them a questionable tactic that lifts conversion 2% is a win they can bank in the metrics. That’s how we ended up with disgusting telephone customer service lately.

Likewise, investors are incentivized for returns within existing playbooks. The fund’s incentives don’t include “is this beautiful and humane?” The engagement loop that’s technically legal but ethically questionable? That’s growth. These people also may have a reputation at stake, so employees and investors do not have the incentives to insist on good design—quite the opposite in fact.

Taste as founder’s superpower

Only entrepreneurs and similar creators have the freedom—and often the desire—to ask: “But is it beautiful? Is it humane? Is this how things should work?”

The founder is typically the only person in the ecosystem with both the skin in the game, incentives and the aesthetic sense to insist on something better. If founders abdicate this role, no one else fills it. That’s why many public companies struggle after the founder(s) depart. At the societal level, given just how valuable beauty is and how under-appreciated it is, founders have the collective duty to insist on good design, educating and advocating others so we come to recognize the value of good taste beyond ‘vibes’.

Bureaucratic, extractive, inhuman systems, in person or online, don’t emerge because evil people design them - mostly. Most emerge because no one insisted on a “not-shitty-experience”. It’s our role as entrepreneurs to revolt aesthetically against ugly products, services and systems—that sort of reaction is always required to challenge the status quo and to invent a better solution.

Closing the Loop

Let’s summarize the core entrepreneurial insights we’ve explored in the last 3 posts.

• In Part 1, we explored how beauty and value share neural circuitry—your brain can’t tell the difference between “this is beautiful” and “this is valuable.”

• In Part 2, we saw how beauty operates as social infrastructure—coordinating communities, reducing collective stress, producing measurable returns in health, safety, and social behaviour.

• In Part 3, we saw how the pursuit of beauty is itself a founder superpower. It’s an intrinsic motivation that sustains effort when external rewards fail. It’s a perceptual capacity that reveals opportunities others miss. It’s a competitive advantage precisely because it’s systematically undervalued by the training most founders receive.

Founders have the unique skills, worldview and incentives to stand for good taste, to insist on beauty because it is truly valuable, and to teach good design principles.

That’s the work of great entrepreneurs. Not just building companies, but building beautiful systems, products worthy of standing the test of time. Not just solving problems, but solving them tastefully. Henry Ford, James Dyson, Edwin Land, and many other great founders spent their entire careers painstakingly perfecting the design of their cars, vacuum cleaners or instant cameras.

They understood that beauty for its own sake was worth pursuing and felt a strong responsibility in pushing the limits of their designs to new frontier, while maintaining a simple and coherent vision of their end goals.

Happy Sunday ✌🏼

Read Tao of Founders

In Part 1, we explored how your brain processes beauty and value through identical neural machinery. The orbitofrontal cortex can’t distinguish between “this is beautiful” and “this is valuable.” That explained individual behavior—why customers pay premiums for well-designed products, why aesthetic violations trigger threat responses, why founders with great taste build products people trust intuitively. We focused on the micro.

Today we explore the macro—how beauty operates at the scale of communities, cities, and companies.

Research points to collective sense of beauty as infrastructure, essential to human flourishing like roads, hospitals, and electrical grids. Infrastructure enables coordination at scale. Roads coordinate movement. Electrical grids coordinate energy. Communication networks coordinate information.

Beauty coordinates human cognition and social organization. It reduces physiological stress, freeing mental resources for complex tasks. It restores attention that demanding work depletes. And—most importantly—it synchronizes emotional states across groups, enabling collective action.

When we remove roads, society visibly breaks down. When we remove aesthetic infrastructure, society breaks down in diffuse ways we’ve learned to ignore. But research in the last 10-20 years clearly shows: failing to invest in beauty is tangibly costing us, and good design provides very high returns.

What Ugliness Costs Us

After World War II, cities in both Europe and US faced massive housing shortages. The response was guided by modernist ideology: function over form, efficiency over beauty, forgetting how brutalist and monotone buildings would feel for those living or working in them.

Take, for example, the Pruitt-Igoe in St. Louis— a 33 eleven-story towers complex.

Elevators only stopped on every third floor. Residents on floors without elevator access had to walk up or down a flight of stairs from the nearest stop. Long, interior hallways had no windows and were shared by dozens of apartments.

The idea for these design choices was to save construction costs and create more “efficient” vertical circulation. In practice, it meant long, unsupervised corridors and stairwells where crime flourished—and residents with groceries, strollers, or disabilities were stuck. Occupancy plummeted from 91% in 1957 to 35% by 1971. Crime made the complex unlivable. It was demolished in 1972, only 17 years after it was built.

Oscar Newman’s research compared Pruitt-Igoe with Carr Square Village across the street—a row-house development with identical demographics that remained fully occupied and trouble-free. The difference was design. Landings shared by two families stayed well-maintained; corridors shared by twenty became disasters; lobbies shared by 150 were a crime scene.

The validation came in Dayton, Ohio. When Five Oaks implemented Newman’s “defensible space”, design that allows residents to naturally monitor and take ownership of the areas around their homes, in the 1990s, overall crime fell 25%, violent crime fell 50%, traffic dropped 67%. These weren’t social programs. They were design decisions.

In the UK, similar large high rise complexes were erected post WW2. Alice Coleman’s research at King’s College London surveyed 4,050 blocks containing over 106,000 dwellings. Litter, graffiti, vandalism, and crime were exponentially more prevalent in high-rises than in streets of houses—far more than population density could explain. Robert Gifford’s meta-analysis of 99 studies found 55 documented negative psychological effects from high-rise living: higher rates of depression, neurosis, and social isolation. Children in high-rises developed fewer friends and showed less-developed social skills. All of this due to dubious design choices!

The post-war experiment proved that utilitarian design ideology—the belief that beauty is secondary—imposes massive costs in crime, mental illness, and community disintegration.

If you think good design is expensive, you should look at the cost of bad design - Ralf Speth, ex-CEO, Jaguar/Range Rover

Beauty delivers a collective ROI

Crime and Violence. In Chicago, researchers studied identical public housing buildings that differed only in vegetation. Buildings with trees and grass experienced 52% lower crime rates. In Philadelphia, greening vacant lots ($1,600 per lot) reduced gun violence 29%, returning over $200,000 in six years—a benefit-cost ratio between 47:1 and 125:1.

Man-made beauty produces similar effects. Philadelphia’s Mural Arts program tracked crime around 500+ streets with murals installed 2007-2023. Crime dropped 42%. Effects persisted up to seven years.

Mental Health. The Philadelphia greening study found depression symptoms decreased 41.5% among nearby residents, and notably 68% for residents below the poverty line. Colin Ellard’s research even measured skin conductance while participants walked past different facades. In front of Whole Foods’ blank glass facade, arousal and mood “took a dive.” Participants described it as “bland, monotonous, passionless” and quickened their pace to escape. One block away, at varied storefronts, they showed high excitement and reported feeling “lively and engaged.” The physiological signature of boredom appeared within seconds.

Healthcare. Roger Ulrich’s landmark study compared surgical patients with nature views versus brick wall views. Those viewing nature required 22% less pain medication, experienced hospital stays 8.5% shorter, and needed weaker analgesics. This single design decision—window orientation—could save $93 million annually across U.S. surgical recoveries.

Richard Taylor’s research found that fractal patterns—the self-similar structures in nature, traditional architecture, and great art—reduce stress by up to 60%. Traditional buildings contain these patterns through ornamentation. Modernist buildings systematically eliminate them.

Learning. Students in daylit classrooms learn 20-26% faster and score 7-18% higher on tests—the difference between a C and B student, achieved through window placement. Children show 2-3x greater sensitivity to environmental design than adults. ADHD symptoms significantly improve with brief nature exposure.

Productivity. Sacramento call center employees with vegetation views handled calls 6-7% faster, generating $2,990 annual gains from a $1,000 window investment—four-month payback, 299% first-year return. Retail stores adding skylights saw 40% sales increases.

Social Behavior. Charles Montgomery’s study assigned participants to pose as “lost tourists” near either active facades (high visual interest) or blank walls. Pedestrians near interesting storefronts were nearly five times more likely to help, and four times as many offered to physically escort the tourist. Beautiful environments transform how strangers treat each other.

The list of beneficial consequence good design, good taste and beauty offers goes on. Clearly there seems to be many ways beauty impacts our collective behaviours.

Why Groups Fail at Valuing Beauty

If beauty has such positive returns and ugliness costs us dearly, why isn’t everyone already investing in design? At the collective level, there are friction points that can hinder understanding and investing in good design.

Split incentives. The developer who saves on landscaping doesn’t pay for the crime increase. The building owner who skips skylights doesn’t suffer the productivity loss—the tenant’s employees do. The hospital administrator who approves cheaper windows doesn’t pay for extra pain medication.

Diffuse benefits. When a beautiful public space reduces stress and increases cohesion, benefits spread across thousands of people in ways no single entity can monetize. The value is real to user, but no one can profit from it.

Cost structure blindness. Research suggests 10% of absences trace to architecture lacking nature connection—costing $2,000-2,500 per employee annually. But because it shows up in HR metrics rather than facilities metrics, no one connects it to design.

As an entrepreneur, the failure of markets to properly price in the value of good taste and design is your opportunity.

The Collective Experience

Individual aesthetic experience activates reward circuitry. But shared aesthetic experience activates additional systems. When people experience beauty together, their brains show greater activation than experiencing identical stimuli alone. Choral singers report significantly higher wellbeing than solo singers—despite identical musical engagement. The difference isn’t the music. It’s the sharing.

This upends how we think about aesthetics. Western philosophy treats aesthetic judgment as individual contemplation. But neuroscience suggests beauty’s primary evolutionary function isn’t individual pleasure—it’s group coordination.

Anthropologists puzzled for decades over why all human societies invest extraordinary resources in aesthetic elaboration. Rituals, ceremonies, decorated spaces, elaborate costumes—massive expenditures with no obvious survival benefit. Why would evolution preserve such waste?

The returns come through social cohesion. Durkheim called it “collective effervescence”—the bonding that transforms isolated individuals into communities capable of collective action. Religious ceremonies worldwide represent humanity’s first “total works of art,” fusing song, dance, costume, and visual display into experiences that create shared identity.

Remove the aesthetic components from these rituals and they fail to produce cohesion. The beauty isn’t decorative. It’s the coordination mechanism.

This explains why some products become cultural phenomena while functionally equivalent competitors languish. Apple users don’t just prefer Apple products individually—they form communities around shared aesthetic values.

The design becomes a coordination mechanism, allowing users to identify fellow tribe members and reinforce each other’s commitment.

Products that nail aesthetics create synchronized experience among users—the neural equivalent of singing in harmony. Products with poor design prevent the collective states where communities form.

What about invisible (moral) beauty?

There’s a form of beauty with nothing to do with aesthetics—and it activates the same neural machinery.

Jonathan Haidt’s research on “moral elevation” documents what happens when we witness exceptional virtue: a stranger helping someone in need, an act of unexpected kindness. The response is physical—a warm, open feeling in the chest, attention turning outward, a desire to become better ourselves.

fMRI studies confirm that moral beauty and facial beauty activate overlapping regions in the orbitofrontal cortex—the same area that processes aesthetic and economic value. When we see someone do something beautiful, our brains process it through the same circuits as seeing something beautiful.

The behavioral effects are striking. In one study, participants who watched an uplifting video subsequently spent twice as long helping with a tedious task—40 minutes versus 20 minutes for controls. They weren’t imitating what they saw. They were “inspired in spirit, not in kind.”

Moral elevation functions as social coordination. When we witness virtue, we’re physically moved to propagate it. Beauty in one form generates beauty in another. The system is designed to spread.

The Weird Principle

One piece of research challenges the assumption that beauty must mean pleasant and immediately appealing. Studies on transformative experiences show that “unfamiliar and uncomfortable settings”, prove particularly effective for growth contexts. Cognitive dissonance appears necessary for genuine transformation.

Medical students in high-stakes simulations showed increased resilience through uncomfortable aesthetic contexts. The transformative potential originated from “disruption of pre-existing expectations triggering self-reflection.”

This suggests optimal aesthetic environments may need to challenge and provoke rather than merely soothe—particularly when the goal is growth rather than recovery.

The distinction matters for anyone building products intended to change how people think. Beauty that confirms expectations is pleasant but not transformative. Beauty that violates expectations in the right ways forces the cognitive work that produces lasting change. That’s why you may find something weird at first before you come to appreciate the beauty.

Entrepreneurial Implications

Your aesthetic choices determine what kind of community forms, who your users are, whether they bond or remain isolated individuals who happen to use the same tool, and whether they become advocates who recruit others. Good design choices are applicable in all decisions, small and large. Hone your taste, learn the timeless principles behind good design, and value taste as what it is: a transformative, meaningful, powerful and worthy endeavour.

The value of good taste can be hard to measure. Don’t mistake lack of numbers for lack of value.

If you view aesthetics as optional, you’ll optimize for features, price, and efficiency—and consistently underperform on dimensions you don’t know you’re competing on.

The companies that do best understand beauty as infrastructure, as coordination system. They invest in aesthetic quality the same way they invest in engineering quality.

The collective implications on beauty takes us to our part 3 - the final part. We will explore why and how to build great taste as a founder.

Happy Sunday ✌🏼

Read Tao of Founders

I was recently reflecting on the beliefs and ideas that most changed since starting my founder journey over 10 years ago. As I wrote in Tao of Founders, keeping your mind fluid and updating faulty beliefs is the logical approach to long term success. Given just how dynamic our world is, holding on to your expired beliefs is very risky.

It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so. - Mark Twain

I most changed my mind around beauty and taste since embarking on my own founder journey. Before I became a founder, I used to believe that beauty & aesthetics were somewhat accessory, luxury ideals that had no hard economic purpose in business. The pursuit of beauty, I thought, was only a concept relevant to the tortured poets and painters of this world. Maybe having trained as an accountant, an MBA, working at Amazon, etc. had led me to worship the gods of data as a religion founded on the belief that a business is first about numbers, quantifiable progress, cost-benefits, and efficiency above all. Anything important should and could be measured. No room for intangibles. To me, beauty in business was like a nice cherry on top, just to be cute- not an integral ingredient of great, enduring businesses.

Turns out qualitative data is usually the most direct, 3D insights with the customer, the market, the product. Quantifying anything always introduces a compression, a loss of resolution - it moves the reality of a single user to a collective statistic. You go from a 3D representation to a 2D representation. Just using numbers won’t tell you anything about how customers think, how they use your product, etc. Good luck making good product decisions without a detailed mental model of your customers. Most humans are confused, conflicted, living imperfectly, making imperfect and emotional decisions. You can’t find that anywhere in the numbers.

It’s hard to convey just how important beauty is in entrepreneurship.

This is where taste comes in. Having great taste enables you to boil down what truly matters for your customers, your product, what to focus on, how to stand out, how to balance things out, and also how to win, how to become a better person, a better team.

We will take a science-first approach to understand why ultimately developing great taste can be a founder superpower.

I’ll use various research insights from different fields to convince you that developing good taste is:

1. Valuable for guiding founder personal growth

2. Extremely valuable for economic and social progress

3. Extremely under-explored as source of competitive advantage

Beauty is purely subjective, so it’s hard to express just how valuable building good taste can be - it’s one of those things you have to see for yourself to fully understand. Even today when I meet my non tech friends, I struggle to communicate to them just how important good taste is. They probably see me as a design snob. That said, beauty is everywhere, if you know how to look for it.

“Everything has beauty, but not everyone sees it.”
― Confucious

Part I: The Science of Beauty

This is a three-part series on the science of beauty, and how it creates real, meaningful economic and social value that founders can harness as a way to become more unique and gain a competitive edge. My goal: at the end of the posts I will have clearly expressed, with science-based evidence, just how valuable good taste is. So valuable that I now believe that the intangible, subjective aspects of a business that relate to good taste and good design are actually what drives most differentiation, most competitive advantages.

Today we will discuss the scientific fundamentals that show the purpose beauty plays and how valuable it can be, looking into modern research from biology, sociology, psychology, and any other fields of science. With that core understanding of the science of beauty, the second part will discuss its role in building businesses and how great founders deliberately hone their sense of taste and design. The last part will bring it all together to provide tools and mental concepts for entrepreneurs who want to harness taste, beauty and design to propel their founder journey.

Your brain on beauty

Your brain can’t tell the difference between beauty and money. When neuroscientists put people in fMRI scanners and show them beautiful faces, paintings, or designs, specific brain regions light up—the orbitofrontal cortex, the ventromedial prefrontal cortex, the nucleus accumbens. These same regions activate when people evaluate prices, assess investment opportunities, or calculate expected returns. The neural machinery that processes “this is beautiful” is identical to the machinery that processes “this is valuable.”

This isn’t a metaphor. It’s neurological fact.

The luxury industry was built on this insight. In luxury, price is part of the design. It shapes the object’s beauty before the eye even sees it. The more expensive something is, the more people expect it to be extraordinary—and the brain works hard to confirm it. People rate wines, chocolates, and experiences as better tasting when told they are more expensive. It doesn’t matter if they are really more expensive - just being told they are is enough to increase perceived value.

This close pairing of beauty and value in the mind explains why founders with sophisticated aesthetic judgment—Jobs obsessing over corner radii, Chesky treating design as strategy, von Koenigsegg approving carbon fiber weaves—aren’t indulging in superficial perfectionism. They’re optimizing the same neural systems that make products feel valuable to customers.

The question is: why did your brain evolve this way? Why does beauty trigger value assessment circuits at all?

Beauty as Survival Technology

The evolutionary answer is simpler than you’d think: your ancestors who found the right things beautiful survived and reproduced more successfully than those with different aesthetic preferences. Beauty isn’t arbitrary cultural conditioning—it’s ancient pattern-detection technology that evolved because it predicted value.

Consider facial beauty, the most studied domain in evolutionary aesthetics. Why do humans across vastly different cultures respond similarly to facial symmetry? Because symmetry signals developmental stability—the absence of genetic mutations, parasites, or environmental stress during growth.

Cross-cultural studies show remarkable consistency: people from isolated tribal societies who’ve never seen Western media respond to the same facial features as people in New York or Tokyo. They prefer averageness (faces near the population mean), symmetry, and specific proportions—not because culture taught them to, but because these features predicted reproductive value for hundreds of thousands of years.

Your aesthetic preferences didn’t emerge from art history classes or fashion magazines. They emerged because your ancestors who found healthy mates attractive, fertile landscapes beautiful, and nutritious foods appealing left more descendants. Beauty evolved as a proxy for adaptive advantage—a shortcut your brain uses to identify what matters for survival.

This is why babies as young as two months old prefer attractive faces before they’ve had time to learn cultural standards. Your aesthetic sense isn’t taught—it’s inherited.

Your Brain’s Prediction Machine

But evolution explains why beauty matters, not how it works mechanically. What’s actually happening in your brain when you perceive something as beautiful?

The answer comes from predictive processing theory: your brain is constantly generating predictions about sensory input and rewarding itself when predictions prove accurate. Aesthetic pleasure is the subjective experience of successful prediction—your brain giving itself a dopamine hit for pattern recognition efficiency.

This is called “processing fluency.” When visual information resolves into coherent patterns quickly and efficiently, you experience that resolution as beautiful. Research on visual perception demonstrates this through simple experiments: patterns people rate as most attractive are precisely those that compress most efficiently—where complex information can be reduced to simple rules.

Your experience of beauty is your brain celebrating its own computational success. The “aha!” moment of aesthetic appreciation is neurologically similar to solving a puzzle—both are dopaminergic rewards for successful pattern recognition. This is how your brain tags important information for attention and memory.

The Neural Circuitry of Beauty and Value

Here’s where it gets interesting for founders: the neural systems that evolved for aesthetic judgment don’t stay confined to mate selection or landscape evaluation. They get co-opted for other domains where pattern detection and value assessment matter—including economic decision-making.

Brain imaging studies show that the orbitofrontal cortex (OFC), critical for aesthetic judgment, is also central to economic valuation. The OFC integrates sensory information with reward prediction to compute subjective value—whether you’re evaluating a potential mate, a piece of art, or a business opportunity.

This isn’t convergent evolution where different systems coincidentally use similar architecture. It’s the same system doing the same computation—assessing whether something is worth attention, approach, and investment—across different input domains.

Research on neuroaesthetics documents this explicitly: “The neural systems underlying aesthetic appreciation and those underlying reward-based decision-making are substantially overlapping, suggesting beauty is processed similarly to more utilitarian forms of value.” When Jobs says a design “feels right” or Chesky describes an interface as having the “right energy,” they’re accessing neural value-detection circuitry that evolved to identify mates and resources.

Beauty as Social Cognition Training

There’s another evolutionary function beauty serves that’s less obvious: art and beauty function as training simulations for social cognition.

This is the Tooby and Cosmides argument: fiction, art, and aesthetic experience evolved because they let you simulate social scenarios without real-world consequences. When you watch a tragedy, read a novel, or engage with visual art depicting human relationships, your brain runs simulations of social dynamics—modeling others’ mental states, predicting consequences of actions, understanding coalitional relationships.

These simulations train the neural machinery you need for real-world social navigation. Someone who’s consumed thousands of hours of narrative fiction has run cognitive simulations of vastly more social scenarios than their actual lifespan would permit.

This explains why aesthetic engagement correlates with enhanced empathy, better theory-of-mind capabilities, and superior social cognition. It’s not that empathetic people prefer art—it’s that engaging with art trains empathy through repeated simulation.

For founders, this matters because entrepreneurship is fundamentally a social cognition task. You need to model customer psychology, predict team dynamics, understand partner motivations, navigate investor relationships. The founder who’s trained their social modelling systems through aesthetic engagement has practiced these skills thousands more times than someone who hasn’t.

The Chills Factor

One of the most intriguing findings in aesthetic neuroscience is the phenomenon of “aesthetic chills”—the physical sensation (goosebumps, shivers, hair standing on end) that some people experience during intense aesthetic appreciation.

Research on aesthetic chills shows this correlates with specific neural activity: increased activation in reward circuitry and decreased activity in threat processing. Chills represent a peak aesthetic experience—when your pattern detection systems recognize something significant enough to trigger physiological arousal.

Here’s what’s surprising: the capacity to experience aesthetic chills predicts personality traits that matter for entrepreneurship. The NEO Personality Inventory includes “experiencing chills from beauty” as a marker for Openness to Experience. High Openness predicts both aesthetic sensitivity and entrepreneurial opportunity recognition—not coincidentally, but because they’re manifestations of the same underlying cognitive capability. That openness could partially explain why people tend to be more creative and more open to perceiving beauty when they are younger.

“Youth is happy because it has the capacity to see beauty. Anyone who keeps the ability to see beauty never grows old.”
― Franz Kafka

People who experience aesthetic chills have more sensitive reward systems for pattern detection. They notice subtle patterns others miss. This is exactly the cognitive profile that enables opportunity recognition: noticing patterns across domains (technology trends + demographic shifts + regulatory changes) and recognizing when they combine into valuable opportunities.

You can train this. Studies on music education show that musical training increases frequency of aesthetic chills by enhancing predictive processing capabilities. The capacity for peak aesthetic experience isn’t fixed—it develops through deliberate practice with pattern-rich environments. As a musician myself, I can attest how this skill-building transfers directly to any other creative work.

The (excellent) book Range by David Epstein supports the same findings—people pursuing varied interests tend to outperform in their main profession.

Beauty as Social Coordination Technology

The neuroscience of individual aesthetic judgment tells only half the story. When people experience beauty together, their brain’s reward systems show greater activation than when experiencing identical stimuli alone.

This isn’t about social validation or peer pressure. It’s about beauty’s primary evolutionary function—not individual pleasure, but group coordination. When your ancestors gathered for rituals combining song, dance, costume, and visual display, they were using aesthetic experience as social technology for emotional synchronization, cultural transmission, and collective meaning-making.

Recent research reveals the mechanism: synchronized neural activity across participants during collective aesthetic moments. When choral singers engage in group performance versus solo singing, they report significantly higher wellbeing—because shared aesthetic experience activates additional neural circuitry for social bonding.

Your product’s aesthetics don’t just trigger individual reward circuits—they create conditions for social coordination among your users. When people collectively appreciate your product’s design, they’re neurologically bonding as a group around shared aesthetic experience.

Consider why some products become cultural phenomena while functionally equivalent competitors languish. Apple users form communities around shared aesthetic values. The beauty of Apple products serves as coordination mechanism, allowing users to identify fellow tribe members and synchronize around common standards. This isn’t marketing. It’s evolved social technology.

The same pattern appears in ceremonial contexts across cultures. Religious rituals worldwide represent humanity’s first “total works of art”—aesthetic experiences fusing multiple sensory channels to create what Durkheim called “collective effervescence,” the emotional bonding that transforms individuals into communities. Remove the aesthetic components—the music, the costumes, the choreography—and they fail to produce social cohesion. The beauty isn’t decoration on top of function. It is the function.

For founders building products used by teams, this matters enormously. Well-designed collaboration tools create conditions for synchronized experience—the neural equivalent of singing in harmony. Poorly designed tools fracture attention, disrupt flow, and prevent the collective states where teams operate most effectively.

Research on transformative aesthetic experiences shows “unfamiliar and uncomfortable settings” prove particularly effective for growth contexts. This explains why products that push aesthetic boundaries often create stronger bonds than conventionally “pleasant” designs. When Tesla’s minimalist interiors first appeared, they violated automotive design conventions. The aesthetic discomfort was intentional—forcing users to rethink assumptions about what cars should be, creating stronger identity commitment through the resolution of that cognitive dissonance.

Your aesthetic choices set the stage for social coordination, determine what kind of community forms around your product, and influence whether users bond collectively or remain isolated individuals who happen to use the same tool.

When Prediction Fails: Aesthetic Violations

Understanding how aesthetic violations work illuminates the predictive processing model. When something violates your aesthetic expectations—faces with wrong proportions, visual compositions with jarring elements, music with unexpected dissonance—you don’t just feel neutral. You feel negative affect. Sometimes strongly negative.

Research on aesthetic disgust shows it activates the insula, the brain region processing contamination threats and physical disgust. Why should a poorly designed interface trigger disgust circuits evolved for avoiding rotten food?

The answer connects back to prediction. Your brain interprets large prediction errors as potential threats. Something that violates your learned patterns might signal danger, confusion, or unreliability. Aesthetic violations activate threat-processing systems because unpredictable environments were dangerous for your ancestors.

Users don’t just fail to appreciate poorly designed products—they experience active aversion. Studies on user experience show that aesthetic quality failures increase perceived difficulty, decrease trust, and activate stress responses even when functional performance is identical. Bad aesthetics aren’t neutral—they’re neurologically threatening. Bad taste makes bad founders.

This explains why founders with aesthetic judgment build products people trust intuitively. Good design reduces prediction error, activates reward circuitry instead of threat circuitry, and makes users feel safe and competent. You’re not optimizing for decoration. You’re optimizing for neural comfort.

Perceiving Beauty in Nature

One of the strongest pieces of evidence for evolutionary aesthetics is cross-cultural consistency. Despite dramatic differences in cultural history, isolated populations show remarkable agreement on what they find attractive.

When shown nature photographs, indigenous populations with no history of Western landscape painting preferred the same types of scenes: savanna-like environments with water sources, varied vegetation, and long sight lines—exactly the landscape features that would have indicated resource-rich habitats on the African savanna where humans evolved.

Studies of color preferences show similar patterns. Across diverse cultures, people prefer blue and green hues (colors associated with clear skies and vegetation) over brown and gray (colors of decay and waste).

Culture absolutely shapes specific aesthetic preferences—what clothing styles signal status, which body modifications indicate beauty, how spaces should be organized. But culture operates on top of universal foundations. Culture customizes the details, but the underlying mechanisms are evolutionary universals.

Why All Of This Matters for Founders

The science of beauty highlights what I had previously missed: when you optimize for aesthetics, you’re not adding superficial polish. You’re targeting ancient neural machinery that assesses value, makes predictions, and drives decision-making. So much of beauty and taste comes down to pattern recognition - a very useful trait for any founder.

It’s important to understand how assessments of beauty happen in milliseconds, using the same systems that evolved to identify valuable mates, resources, and environments. All of this subconscious mental work informs precisely how a customer feels, their experience and whether they want to choose you again or not.

In part 2, we’ll continue to explore the links between beauty and value collectively.

Happy Sunday ✌🏼

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Sooner or later, most founders encounter a life situation that feels so challenging, so painful, and so humbling that it brings them to a moment of surrender. As difficult as these moments can be, overwhelming struggle is a normal part of your hero’s journey. With the benefit of age and experience, I’ve come to see more clearly that the way I embrace my lows is what ultimately defines my fate. So I embrace those lows by welcoming the difficult emotions too. Pain can be the ideal teacher, if you let it be. Surrendering is not the same as giving up.

Expectations and Struggle

Although painful mistakes in entrepreneurship are guaranteed, I believe that founders can save themselves some emotional struggle by understanding how the expectations they create influence their emotions.

Given that you’ve become good at solving problems for a living, you might be tempted to approach everything as a problem to be solved. I love solving problems, sometimes even when there are no problems to begin with. With only a hammer, everything starts looking like a nail. But life is ultimately more than hammering nails. Life is a voyage, not a puzzle.

As crazy as it might sound, you don’t have to fix anything. If you’re seeing problems to solve everywhere, you might want to reevaluate how you form your expectations. Maybe that’s where a lot of these troubles are coming from.

Expectations are beliefs and assumptions you hold about the future. On one hand, holding high expectations can be a self-fulfilling prophecy. Expecting excellent work might help your team rise to your high standards and achieve something they didn’t know they had in them. On the other hand, low expectations can save you from the brutal sting of failure and disappointment.

When should you have high or low expectations? High vs. low expectations is another duality paradox. From my own experience, expectations should adjust based on the time horizon—the larger the time horizon, the larger the expectation. Finally, expect to be disappointed a portion of the time. That includes your expectations of yourself. Your expectations should leave a margin of error—we’re all flawed, complex, and unpredictable humans.

Positive Expectations or False Hope?

James Stockdale was held captive for over seven years during the Vietnam War. He observed that the most optimistic prisoners often fared the worst, because they were crushed when their expectations were not met, having falsely expected, for example, that they would be released by Christmas Day.

Stockdale maintained his will to survive by accepting the powerlessness of his reality while retaining faith that he would eventually prevail. This mindset, termed the “Stockdale Paradox,” involves balancing unwavering faith in eventual success with the discipline to face a brutal reality.

This paradoxical mindset holds high and low expectations simultaneously: high expectations in the long term, low expectations in the short term. It’s an attitude I’ve observed among outstanding founders too. They believe their success is inevitable, while expecting, even relishing, failures and adversity along the way. Managing your expectations effectively saves you emotional turmoil.

The Fruit and the Labor

Steve Jobs was famous for repeating the old adage “The journey is the reward.” To me, the biggest factor in Jobs being one of history’s most impactful founders was his ability to hold both extremely high and low expectations simultaneously.

He chose his journey for the journey itself, with no expectation of outside success, motivated intrinsically to “make insanely great products,” wherever that might take him, all while letting go of any expectations of specific results. Jobs held very high expectations in terms of the quality of design, but he focused on the act of creation itself.

Today Jobs is remembered for his successful products, but we forget he shipped a bunch of failed product ideas: the Apple Lisa, NeXT Computer, Newton handheld, Macintosh TV, and iTunes Ping to name a few.

“The journey is the reward” is a timeless and universal mantra. The Bhagavad Gita, an ancient Hindu scripture written around 200–400 BCE, explores a crucial paradox that founders encounter to this day: how to pour yourself into your creative calling while detaching from expectations of results.

“You have a right to perform your prescribed duties, but you are not entitled to the fruits of your actions. Never consider yourself to be the cause of the results of your activities.”

— Bhagavad Gita, chapter 2, verse 47

Embracing this philosophy made Jobs bolder and more tolerant of failure. When he returned for his second stint at Apple in 1997, he was looking at failure dead in the eyes. The company was weeks away from bankruptcy. Without pressure to conform to high market expectations, Jobs could see clearly what Apple needed and went on to lead one of the most epic turnarounds ever.

Unimpeded by fear, he felt more apt to make the concentrated, contrarian bets that gave us the iPod, iPhone, and iPad.

A Fearless Mind

A fearless mind free from expecting results is a powerful combination: this is the mindset of someone with nothing to lose. Think about this: What would you keep doing even if failure was assured?

If you are doing something hard and new, try starting with the assumption that failure is the likely scenario. Because it is. Assuming failure in this case is not pessimism; it gives you freedom to do your best work.

If you can find true inner motivation to pursue your path regardless of success or failure, then nothing can stand in your way. Choosing your “hill to die on” ultimately helps you clarify your deepest intentions.

Defining and owning your symbolic hill creates a healthy distance between you and your expectations for the future. Find something you want to create so badly, something that needs to exist so much, that it makes all your sacrifices worthwhile in the end.

Fruit Without Attachment

Paradoxically, when you don’t expect results and don’t buy into fear of failure, your labor might yield more “fruit” than you could ever get otherwise.

What should you do when all these bounties come your way? Help others and further your sense of purpose. These fruits were not for you to expect nor hoard. Sharing the abundance in your life will only multiply your wealth.

The Buddha taught that generosity brings happiness at every stage of its expression. We experience joy in forming the intention to be generous. We experience joy in the actual act of giving something. We also experience joy in remembering the fact that we have given.

“You have not lived today until you have done something for someone who can never repay you.”

— John Bunyan

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If I had to distill the very essence of founder mentality in terms of what distinguishes (and somehow predicts) the sharpest, most powerful aspects of entrepreneurial mindset, would come down to a “holy” triad - which we’re going to explore in this post:

1. Seek more ownership - and leverage it

2. No one is coming to save you- you are your own saviour.

3. Creation beats consumption - every time

Entrepreneurial Intentions and actions that align to those three things will by definition set you apart as entrepreneur. I’ve seen those principles in action in the last decade and these are the very essence of what makes an excellent founder vs. an average one.

Always seek more ownership

Adopt a pro-ownership mindset—psychologically owning every outcome (good or bad) in your business. You are always responsible for what happens to you and how you respond, even if events are not your fault, even if you made a mistake and it’s your fault. It doesn’t matter whose fault it is, you are responsible. Responsible to own your outcomes and own the way you respond to a challenge. Own it.

Research on psychological ownership shows it’s a powerful motivator: when you feel truly responsible for the venture, you act more like an owner, fuelling creativity, persistence, and hope. This contrarian approach counters the common human tendency to deflect responsibility. Look for those traits in your employees, usually the best type early stage employees tend to be good at spotting and tackling opportunities without being prompted to. They just seek more ownership and autonomy, and they are able to do so with increasing ownership because they are able to think and act just like you would as an owner.

Just by being willing to be accountable, you become contrarian. That by definition sets you apart from the average person. So few people in public institutions are willing to publicly own their mistakes, to take the blame when something goes wrong. In addition to social incentives to not stick your neck out too much, most public employees have no skin in the game. Even If they did ask for more accountability they wouldn’t really be in a position to gain proportionally (incentives design is a topic for another day).

Ownership and accountability brings you leverage. By running towards the fire when others escape, you earn recognition and you unlock more options. You used ownership to be fully accountable for and associated with solid outcomes. People will in turn trust you with bigger opportunities.

“You can’t build a reputation on what you are going to do.” — Henry Ford

Psychological ownership fuels action: When people feel like owners, they go beyond their formal roles. Ugwu et al. (2025) found a strong link between psychological capital (a mix of self-efficacy, hope, optimism, resilience) and entrepreneurial behavior. Those who mentally “owned” their work would “identify opportunities, take a risk and explore it until the result is achieved, not giving up to constraints and challenges”.

For a founder, always seeking more ownership means treating every problem as your problem—and thus something you have the power to solve. Research shows that when people feel high ownership, they don’t easily give up—they “take risks and explore opportunities until the result is achieved, not giving up to constraints”.

As a founder, it becomes a superpower to instil an entrepreneurial mindset with your team, setting the right environment for the team to naturally feel like they own their work, their product, the entire destiny of your startup. When leaders empowered their people, those with proactive personalities showed higher resilience—implying that an ownership attitude under stress helps one “develop positive…resilience”.

Caveat—don’t over-identify to the point of harm: Taking ownership is productive; becoming the company is dangerous. Psychologists warn that over-identification with your venture can increase emotional risk and volatility. Lin et al. (2024) caution that when a founder’s personal identity is too tangled up with the startup, every setback feels like a personal attack, leading to severe stress or decision paralysis. The key is to care deeply and take responsibility without losing a separate sense of self. Think of it as “Own the ship, but remember you are not the ship itself.” This distinction lets you stay resilient—you can weather storms without sinking your self-worth.

Save yourself

The logical conclusion of a pro-ownership mindset is that you shouldn’t expect others to be responsible for saving you in hard times. When adversity hits, many people consciously or subconsciously hope for a saviour, an external event that will magically fix everything—just at the right time.

Similarly, we tend to seek happiness in external events instead of remembering that we shouldn’t make our well-being conditional on things outside of our control. Movies often depict those epic saviour moments—usually at the final scene when our hero is about to get killed, an old friend or some other external, unexpected force comes into play to neutralize the vilain and save our hero at the last second. I guess we tend to see this pattern a lot in Hollywood because our human minds is drawn to that sort of stuff— on a subconscious level, I think we all secretly hope to be saved. Of course this is magical (and flawed) thinking.

This self-rescue mindset is high agency in action. By all means you should ask and seek help from other people. But you shouldn’t expect any single person, event, or anything to somehow save you, or even change your life at once. Stop fooling yourself. You need to make your mission happen all on your own.

That’s why entrepreneurship is hard. We don’t talk enough about the struggle that comes from wrestling with your issues, on your own, without expecting anyone else to care. While it might sound bleak, it is more constructive to start your day with the premise that no one cares - unless you give them a good reason to!

Just like a pro-ownership mindset, a self-rescue mindset has clear links to entrepreneurial resilience. Founders with an internal locus of control—i.e. save yourself—believe outcomes stem from their own actions, not external forces. This mindset has tangible benefits. Hamzah & Othman (2023) found that internal locus of control in entrepreneurs led to better business performance and life satisfaction through improved competencies. In their study, “beliefs based on internal attributions…define entrepreneurs’ destiny,” linking to positive venture growth and personal well-being.

Internal locus is about control beliefs; self-efficacy is belief in your skills and capacity. High self-efficacy means you’re confident you can do what needs to be done on your own. Unsurprisingly Research by Olabimtan & Jaiyeola (2025) highlights that entrepreneurs with strong self-efficacy tend to take initiative rather than waiting on others.

Research by Farradinna et al. (2019) on young entrepreneurs showed that those with a strong internal locus perceive obstacles and difficulties as challenges to be conquered. They “see themselves as an important factor determining their own success”. This trait closely ties to hope and persistence—believing you have control breeds a fighting spirit. That same study also linked internal locus with fostering hope and success expectations.

Entrepreneurs with a self-rescue mindset trust their own ability to solve problems, which naturally reduces over-dependence on advisors, mentors, or luck. (A founder with low efficacy might defer every decision to an “expert” or constantly seek validation, whereas a self-efficacious founder will gather input but ultimately make and act on decisions.) Self-efficacy correlates with proactive behavior, higher innovation, the courage to act independently and to take unpopular yet necessary actions.

Self-rescue is largely about self-regulation. Believing “it’s on me” also means managing yourself in tough times. Internal locus and self-efficacy work best when paired with self-regulation—the ability to control your emotions, focus, and actions. Farradinna & Fadhlia (2019) found that internal locus of control contributes to higher psychological resilience especially through self-regulation. Essentially, confidence + emotional discipline is a potent combination.

If you think you’re in control, you act like it, build relevant skills, and ultimately get better results. Hoping for a saviour is a subtle way to give up your sense of control. By contrast, those with an external locus saw “no such consequences.” The research provided “compelling evidence of the adverse consequences of relying too heavily on fate or external assistance”.

Caveat—guard against overconfidence and blindness. Here’s the contrarian twist—believing in yourself is good, but too much self-belief can backfire. High self-efficacy without humility can morph into overconfidence, causing founders to ignore feedback or risks. Zhao & Wibowo (2021) caution that when entrepreneurs’ self-efficacy goes unchecked, it can “blind [them] to essential market signals” and prevent them from acknowledging mistakes. Being your own saviour shouldn’t mean ignoring advice or red flags—like dismissing user complaints or mentor warnings.

Scholars call this the “optimism paradox”: the same optimism that drives you can also deafen you to criticism. The key is to balance internal confidence with external awareness. Use your self-efficacy to take bold action and use your self-awareness to course-correct.

Creation over consumption

“Everything around you that you call life was made up by people that were no smarter than you.” — Steve Jobs

The last trait that sets the entrepreneurial mind apart is the fundamental belief that a creativity-oriented life is the antidote to a passive, consumerist way of life. If life was a play, would you watch it, or be in it? Most people just watch life go by, totally unaware they can actually be a character in the play, that they can join and even shape the unfolding of events.

Steve Jobs made that excellent point that stuck with me over the years: “When you grow up you tend to get told that the world is the way it is, and your life is just to live your life inside the world,” Jobs said, describing the invisible script most people follow. “Try not to bash into the walls too much... but that’s a very limited life.”

Jobs believed that once people understood that they too could shape the world, influence it, and leave their own imprint, a fundamental shift would happen—and there’d be no going back.

Jobs urged people to abandon the passive belief that life is a fixed structure in which one simply plays a role. Instead, he saw life as a pliable force, waiting to be pushed, shaped, and questioned. That’s a creativist take on life—one that is the opposite of consumerism. Given how little friction there is today to accessing more online content, buying things online, consumption has become easier (and even encouraged). Consumption goes beyond the material; it puts us in a state of always desiring, reaching for more, while creativity lets you truly enjoy what you already have inside of yourself: your ideas, your creative energy. These are compounding forces.

“You can’t use up creativity. The more you use, the more you have.” — Maya Angelou

What does that look like in practice? Anything that shifts the default from observation to action. Writing instead of reading. Playing music instead of watching TV. Nothing wrong with passive consumption here and there, but be careful if this becomes your default mindset. Rest is not the same as passive consumption by the way—rest is also best done when taking a proactive stance to it.

“It is better to create than to learn! Creating is the essence of life.” — Julius Caesar

More precisely, creating is the single best way to learn as a founder. I did an MBA from a fancy school and took all the entrepreneurship classes. It mostly motivated me—I ended up learning the real lessons only when I created my own startup. If you’re an engineer building a bridge, you certainly need to study how other bridges are built, and think carefully before you start acting.

Entrepreneurship is different. The only way to think well as a founder is while in action. The only way to learn fast and increase your odds of success is action. Action, thinking and learning are one and the same in entrepreneurship. Assume your actions are what shape your thinking, and your actions prove to you that the world is malleable.

Evidence from small business research suggests that resilience comes more from agility and experimentation than from elaborate planning. Branicki & Sullivan-Taylor (2018) studied how small and medium enterprises (SMEs) survive disruptions. They found that, unlike big firms which rely more on formal plans and buffers, resilient SMEs focus on “capacities to cope with uncertainty,… generating personal relationships, and activating the ability to experiment and think creatively in response to crises.” In short, no better way to learn than on the fly.

Further, formal planning has limits—“Rather than encouraging formal planning and redundancy… practice should pay greater attention to building capacities to cope via experimentation and creative thinking in crises”. In other words, be a maker, not a meticulous planner, if you want to bounce back fast. Don’t spend your time on a business plan; spend your time building the thing instead.

Many founders fall into the trap of information overload, sometimes as a ‘smart’ way to procrastinate. I do that with podcasts that are super interesting but somehow change nothing about what I do or how I act. I wouldn’t let myself watch trash TV, but I somehow find listening to podcasts more justified. Even if I learn something it’s still a hidden form of procrastination given that knowledge is of no real application in my life.

Will AI make founders of the future more creative or more passive?

In my opinion, AI will only increase that mental gap between creativist and consumerist way of life. AI can greatly enhance your ability to consume more and better information, just like it can also greatly enhance your creativity, your creative output and the effort needed in the process.

The more AI technology we have at our disposal, the more important the perception of “shaping versus consuming” becomes. Ultimately AI is just an accessible tool, and creativity and impact will be increasingly defined by how intentionally humans engage with AI technology, which will define how AI is used for what purpose.

Conclusion: the triad reinforces itself

If you want to become always more entrepreneurial, these are the mental attributes to nurture. The entrepreneurial triad—pro-ownership, self-rescue and creativist traits—all reinforce each other towards ever greater individual impact and agency, and that’s why they really fit well together as a triad. Based on my experience, these are the most powerful, distinctive beliefs I’ve observed among the founders I respect and admire most—these are the few, rare things that truly sets them apart from average.

Have a nice Sunday! 🌕 ✌🏼

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