“He who is attached to things will suffer much.” — Tao Te Ching, Chapter 44

Startup culture encourages total commitment - and usually rewards those most obsessive about growing their company. And yes, commitment is a prerequisite to doing hard things.

Obsessive tendencies among high performers is not an innate traite. It is the predictable output of a an ecosystem — accelerator interview, weekly metric, demo-day deck, quarterly board — that selects for, rewards, and amplifies obsessive patterns among founders. While obsession can motivate us, it usually isn’t a sustainable source of energy and drive over the long term.

The Two Passions

In 2003, the Quebec social psychologist Robert Vallerand published “Les passions de l’âme: On Obsessive and Harmonious Passion” in the Journal of Personality and Social Psychology. Drawn from four studies of more than 900 participants, the paper did what motivation research had mostly avoided. It refused to treat passion as a single thing. It split it.

Vallerand’s Dualistic Model of Passion distinguishes two ways an activity gets internalized into the self. Harmonious passion is an autonomous internalization — the activity is freely chosen, integrated with the rest of the person’s identity, in flexible relationship with the rest of life. When the founder closes the laptop on Friday night, harmonious passion lets the laptop close. Obsessive passion is a controlled internalization — the activity is internalized under pressure, often because self-worth or social approval has become contingent on it, and it sits rigidly at the center of identity. When the founder closes the laptop, obsessive passion does not. It rides home in the car. It runs in the shower. It wakes the founder at four to check Slack.

The two variants look identical from the outside. They produce the same hours, often the same output, sometimes the same revenue. The downstream physiology is opposite. Harmonious passion predicts flow, positive affect, sustained performance, and life satisfaction. Obsessive passion predicts rumination, life-domain conflict, anxiety, depressive symptoms, and burnout. A 2020 meta-analysis by Pollack, Ho, O’Boyle, and Kirkman, pooling 106 samples and 38,481 participants in the Journal of Organizational Behavior, found obsessive passion correlated with burnout (ρ = .46), emotional exhaustion (ρ = .31), and psychological distress (ρ = .14). Harmonious passion correlated negatively with all three. Same word. Two physiologies.

The construct ports cleanly into entrepreneurship. Melissa Cardon’s 2009 Nature and Experience of Entrepreneurial Passion in Academy of Management Review is the canonical adaptation. Five years later, Murnieks, Mosakowski, and Cardon tested the dualistic version in 221 entrepreneurs: passion rises with how central the entrepreneurial role is to the founder’s self-concept, and when centrality crosses a threshold, harmonious tips into obsessive. The same identification that drove the founder forward becomes the mechanism through which a venture setback is metabolized as personal annihilation. The founder does not have a hard quarter. The founder is the hard quarter.

The split is measurable, with a validated seventeen-item scale translated into more than twenty languages. The venture-capital pipeline, run end to end, puts founders on the wrong side of it.

How the Funnel Manufactures the Wrong Variant

Walk a founder through the modern venture funnel and watch what each stage selects for.

The first filter is the pitch. Every accelerator interview, every seed deck template, every founder-to-VC intro is built around a question that sounds neutral and is not. How committed are you? The socially acceptable answer, the one that produces a term sheet, establishes that nothing in the founder’s life is allowed to compete with the company. It’s a form of signalling.

The second filter is the cadence. Demo day exists, structurally, to produce a sixty-second pitch and a hockey-stick chart. The published growth target is five to seven percent week-over-week, with ten flagged as elite. A weekly metric is a weekly identity referendum. Founders inside that cadence stop measuring time in months and start measuring it in increments of self-worth. The cadence itself, before any specific advice is given, holds the founder’s nervous system hostage to the seven-day moving average. Paul Graham’s Do Things That Don’t Scale celebrates this: the Airbnb founders, he writes admiringly, “always just flown back from somewhere,” rolly bags in tow at the YC dinner. The essay reads as inspiration. In the Vallerand framework it also reads as a clinical case file — rigid persistence, life-domain conflict, identity collapse onto a single activity.

The third filter is the mythology. The founder slept under the desk ( I did that for a while) . The founder mortgaged the house. The founder missed the wedding. The founder ate one meal a day. The founder did not see their kids for a year. These are not incidental color. They are credentials — the way the protagonist signals to investors, journalists, and future hires that the activity has been internalized in a controlled rather than autonomous way. The genre is, almost without realizing it, a genre about obsessive passion presented as virtue. YC president Garry Tan recently warned founders against celebrating “sleepless” work culture — useful, and a measure of how thoroughly the inversion has happened.

Aggregate the filters. Selection at the front door for obsessive tendencies. Cohort cadence that converts weekly metrics into weekly identity mini-crises. Cultural mythology that rewards life-domain collapse with status. Cap-table mechanics that lock the identity-metric coupling in for the duration.

Predictable physiology — burnout, rumination, relational damage, depression — shows up in 49% of founders with a personal mental health history and 72% with mental health concerns, as Michael Freeman’s UCSF/UC Berkeley team documented across 242 entrepreneurs in Small Business Economics.

How Athletes Approach Obsessive Passion

Elite athletics ran the same experiment for a long time and broke a lot of athletes doing it.

Björn Borg won eleven Grand Slams and walked away from tennis at twenty-six. Asked why, he told reporters in 1983: “I started to play tennis when I was nine. I think I had a tennis racket in my hand twenty-two hours a day. Now I want to live.” Andre Agassi, eight-time Grand Slam champion, opened his memoir Open with a sentence that could have been pulled directly from the Vallerand obsessive subscale: “I play tennis for a living, even though I hate tennis, hate it with a dark and secret passion, and always have.”

Suzy Favor Hamilton ran in three Olympics on a body she had been taught to override; she later wrote in Fast Girl that the medal stand felt like a hostage situation she could not name. None of these were personal failures. They were the predictable physiological output of a training culture that, like the venture funnel, selected for and amplified obsessive identification with the activity.

What happened next is the part the founder world has not copied. The federations did not tell athletes to be tougher. They added counter-pressures. In 2013, the European College of Sport Science and the American College of Sports Medicine issued a joint consensus statement on the prevention, diagnosis, and treatment of overtraining syndrome that became the operating standard. The International Olympic Committee followed in 2016 with its own consensus on load management, framing athlete health as a load-recovery continuum rather than a willpower competition. Periodization — structured cycles of build, peak, and recovery — became non-negotiable across endurance sport. Recovery weeks were written into training plans, not improvised on bad days. Coaches were re-credentialed in load monitoring. Sport psychologists became standard staff. Eating-disorder protocols were federated through the IOC.

In January 2024, the NCAA approved new mental health best practices requiring every member institution to designate a licensed mental health provider for the athletic department, screen every athlete annually with a validated psychological-distress instrument, and maintain documented referral pathways to clinical care. The institutional posture had inverted: psychiatric load became the federation’s problem to absorb, not the athlete’s to suppress. When Simone Biles withdrew from the Tokyo 2020 team final, citing the “twisties” and her mental health, USA Gymnastics did not strip her credentials or replace her on the roster. They sent in a sport psychologist. Naomi Osaka pulled out of the 2021 French Open over press-conference anxiety; the WTA’s response, after a clumsy first week, was to publish new media-rights guidelines.

The athletes did not get tougher. The federations did. The counter-pressures were structural, not personal. It took roughly thirty years of measurable harm before they admitted they were the variable that needed to change.

The contrast with the founder ecosystem is structural and exact:

Counter-pressure Elite Athletics Venture-Backed Founders Mandated annual mental health screening NCAA Best Practice #2, 2024 None Licensed mental health staff embedded on site Required at every NCAA D-I program None Credentialed load-management protocol IOC, ECSS/ACSM consensus None Recovery cycles in the training calendar Periodization, mandatory rest weeks None Overtraining as a recognized clinical entity Yes, since the 1980s No founder-equivalent diagnosis Identity-flexibility programming Standard at Olympic training centers Mythology rewards identity collapse

Every row exists because the underlying activity, left to its own incentives, manufactures obsessive identification with itself. The counter-pressure is the difference between durable performance and a body count quietly attributed to the bodies that delivered it.

Establishing Harmonious Passion

Given that the fundraising funnel tends to selects for obsessive over harmonious passion, what does an individual founder do to keep the harmonious variant intact in their lives?

The first move is diagnostic. The Vallerand passion scale is freely available. The harmonious items describe an activity integrated with the rest of life — this activity is in harmony with the other activities in my life. The obsessive items describe an activity that has overrun the perimeter — I have difficulties controlling my urge to do my activity, if I could, I would only do this activity. Most founders, asked honestly, can already feel which side of the line they are on. Naming it is not weakness. It is the baseline an Olympic athlete gets in their first week.

The second move is to build the counter-pressures venture capital did not. A periodized week with a non-negotiable low-load day. A relationship — partner, friend, sibling, parent — that is not contingent on company performance and is therefore allowed to puncture the identity bubble when it starts inflating. A licensed clinician on call who can distinguish a hard quarter from the early signs of major depression, a distinction the founder cannot make from inside their own head. A recovery practice — sleep, aerobic base, time outdoors — treated as a load-management instrument, not as a wellness reward for shipping. None of this is soft. All of it is the founder version of what an Olympic strength coach hands an athlete on day one.

The third move is identity diversification. The Vallerand model does not say founders should have less passion. It says passion is a problem when it is the only support holding up the self. Ian Thorpe won five Olympic golds, retired at twenty-four, and was hospitalized for depression two years later; his autobiography names the single-identity collapse explicitly. Eliud Kipchoge, the only person to run a marathon under two hours, runs about 200 km a week and then goes back to a training camp where he sweeps the floor, takes a long nap, and writes in a journal. “Only the disciplined ones in life are free,” he likes to say — and the discipline he is naming is the discipline to stop. A founder with a single identity has nowhere to go when the round does not close. The protective factor is not less commitment. It is more identity surface area. Music, family, faith, friendship, craft — not distractions from the company, but the redundancy that keeps company stress from becoming existential stress.

The Tao Te Ching keeps returning to the idea that the activity that holds nothing back will exhaust itself, and the one that holds something in reserve will outlast it.

The founder who keeps a portion of the self outside the company is not less ambitious. They are in fact the opposite - meticulously aiming to keep going for a long time.

Identity foreclosure is a psychological state where an individual commits to an identity, values, or career path—sometimes assigned by parents or society but not always—without exploring alternatives. Defined by high commitment and zero exploration, identity foreclosure often leads to later life crises when these premature, rigid roles are challenged.

What Identity Foreclosure Is

The concept comes from the developmental psychologist James Marcia, who in the 1960s extended Erik Erikson’s work on adolescent identity formation into a fourfold typology. Marcia argued that mature identity is the product of two processes: exploration of alternatives, and commitment to a chosen path. The status that matters here is identity foreclosure — commitment without exploration, locking into a role early, often inherited or socially scripted, without ever having tested the alternatives.

The Four Identity Statuses

• Identity Diffusion (Low Exploration, Low Commitment): Individuals have not explored options and have not committed to any direction. They often feel indifferent or confused about their future.

• Identity Foreclosure (Low Exploration, High Commitment): Individuals have made commitments to a role or belief without engaging in exploration or questioning.

• Identity Moratorium (High Exploration, Low Commitment): Individuals are actively exploring, questioning, and experimenting with various alternatives but have not yet made firm commitments.

• Identity Achievement (High Exploration, High Commitment): Individuals have passed through a period of exploration (moratorium) and have successfully made firm commitments to specific values, goals, and beliefs.

In 1993, Britton Brewer, Judy Van Raalte, and Darwyn Linder published a paper titled “Athletic Identity: Hercules’ Muscles or Achilles Heel?” in the International Journal of Sport Psychology, introducing the Athletic Identity Measurement Scale — a validated instrument that quantifies how much an individual identifies with the athlete role. The paper explored dual-edged dynamic:

Strong athletic identity correlates with greater motivation, training adherence, and performance, and simultaneously correlates with vulnerability when the identity is threatened by injury, deselection, or retirement.

The scale has since been used in over a thousand studies, and the meta-analytic finding is unambiguous: athletes who score high on identity exclusivity experience markedly worse outcomes during career transitions.

Albert Petitpas and Thaddeus France connected this directly to Marcia: the athlete who has never explored an identity outside sport has foreclosed prematurely on a single self. The very thing that produces the performance produces the vulnerability.

The numbers on what happens when that vulnerability meets a transition are concrete. A systematic review of psychological distress among retired elite athletes reports depression prevalence ranging from roughly 5% to 29%, with clinician-assessed studies clustering above 20% — meaningfully higher than population baselines.

Approximately 20% of retiring athletes experience the transition as an outright crisis. Lavallee and Robinson’s 2007 qualitative study of retired women’s artistic gymnasts is the most vivid: participants described feeling “incredibly lost,” unable to find a replacement for the unidimensional self-concept the sport had built. The retirement was, for several of them, traumatic.

These are not soft findings. These are the predictable consequences of a system that selects for total identification and provides no easement into what happens when the role ends.

The Founder Version

Now look at the founder side and notice that we have built a near-identical selection mechanism with none of the surrounding clinical apparatus.

The empirical literature on founder identity is mature and largely consonant. Murnieks, Mosakowski, and Cardon’s 2014 paper “Pathways of Passion” in the Journal of Management, based on structural equation modeling of 221 entrepreneurs, established that entrepreneurial passion rises and falls with how central the founder role is to a person’s self-concept.

High identity centrality drives self-efficacy and action in entrepreneurs — but when centrality crosses a threshold, harmonious passion converts into obsessive passion, which is associated with rumination, conflict with other life domains, and psychological distress when the venture is threatened.

Matthew Grimes’s 2018 field study of 59 founders in the Academy of Management Journal made the failure mode operational. When founders treat their ideas as extensions of self-concept, external feedback intended to improve venture viability is processed as identity threat, producing resistance to revision. The pivot — the single most important survival behaviour of a young company — becomes psychologically unavailable to the founder whose identity is fused most tightly with the original idea.

The most precise framing comes from Eliana Crosina and Michael Pratt’s 2024 paper in Organization Science. Their three-year inductive field study of first-time founders found that the founder-venture identity relationship is not a fixed trait. It oscillates. Founders move between identification — seeing the venture as self-defining — and distancing — seeing it as a separate object.

Founders who can move flexibly between the two states make better strategic choices: they pivot when pivoting is correct, persevere when it is correct, and exit when it is correct. Founders who cannot distance make worse choices across all three. The capacity to step in and out of the role identification is key.

The Infrastructure Athletes Built and Founders Did Not

Athletes have built, over thirty years, the explicit vocabulary and resources for understanding and managing identity foreclosure, normalizing the conversation, and intervening before the transition cracks a person. On the other hand, founders have built none of that — and are at risk of being blindsided by the intense void that the foreclosure brings once the entrepreneurial journey concludes.

For example, sport psychology has developed AIMS as a screening instrument. In short, it evaluates three distinct areas: Social Identity (role as an athlete), Exclusivity (self-worth based on performance), and Negative Affectivity (emotional response to poor outcomes). There is no founder-equivalent inventory that I know of.

Sport psychology has Life Development Intervention, developed by Danish, Petitpas, and Hale in 1993, a psychoeducational protocol explicitly designed to use sport as a vehicle for transferable life skills and identity exploration outside the role. It assumes the elite athlete will eventually transition out of sport and that the transition will be survivable only if exploration of other identities has been scaffolded during the career, not after.

Olympic committees have integrated career assistance programs along these lines for more than two decades. Founders have nothing structurally equivalent. No accelerator curriculum teaches identity flexibility.

It is no wonder that 75% of business owners regret selling within a year (Exit Planning Institute, 2013), or that only 22% say post-exit life matches their dreams (Yale SOM, 2025). Worse, 70% of post-exit founders did zero planning for life after (Yale SOM, 2025, n=52, $10M+ exits).

Why It Is Structural, Not a Personal Failing

The obvious read of a post-exit identity collapse is that the founder was “too obsessed.” The over-identification is not a personal character flaw. It is produced by the environment the founder is required to operate in, and any founder who refused to over-identify would, in expectation, produce a worse company.

Consider what venture backing selects for. The investor underwriting a seed check is paying for monomania. They want a founder who will think about the company in the shower, at dinner, at three in the morning, on the day their child is born. Pitch decks compete on how thoroughly the founder has fused themselves with the problem. The founder who says, on stage, that they are interested in many things and this is one of them, does not close the round. The selection is explicitly rewarding the all-in behaviours, those that set you up for identity foreclosure later on.

Once funded, the operating environment compresses identity further. Compensation pays in equity — a single-asset concentration in the company. The social environment narrows to founders, investors, and employees, all of whom are talking about the company. Cognitive bandwidth narrows because the cadence forbids anything else. The founder becomes a person whose conscience, calendar, finances, friendships, and sense of competence all share a single substrate.

Athletes faced this dilemma and resolved it through institutional design rather than individual willpower. Federations made career transition programs mandatory. Universities required student-athletes to declare a major outside athletics. Sport psychologists built protocols that asked athletes to articulate roles outside the sport on a recurring cadence throughout the career. The intervention was not “be less of an athlete.” It was “be also something else, deliberately, with a coach, on a schedule.” It was structural, and it worked because it did not depend on the athlete spotting their own foreclosure from inside the foreclosure.

The Operational Reframe

Identity flexibility is a strategic skills that can be developed, and the founder who treats it as such will, on average, build a better company and survive the transitions the company forces on them.

Explicit identity work can help you move fluidly between identification and distance. This work will look different for everyone: journaling, creating a third place, practicing a creative hobby. Each is meant to insert enough space between you and your own identity as a founder to loosen up a bit, and gain clarity from a less involved sense of self. Again, elite sport has been advocating for explicit identity reframing protocols for decades.

Sooner or later, the transition out of the company happens to every founder. This isn’t a rare thing — yet we seem to ignore how much of a transition it demands for us to rethink our whole life narrative, fully choose who we are and what we value. The first step is to let yourself imagine your life outside of your startup and what that your identity will rely on once that day comes and your entire self-definition shifts from under you.

In 2024, neuroscientists at Carnegie Mellon recorded something no one had ever visualized before: the exact moment a brain chokes.

They were tracking neural population activity in the motor cortex of primates performing precision tasks under varying reward conditions -- a model that closely mirrors human motor architecture. When the reward got large enough, neural activity literally migrated away from the region responsible for successful execution. Not because the subject was nervous. Not because they were distracted. Because they wanted it too much.

The finding, published in Neuron by researchers at Carnegie Mellon and the University of Pittsburgh, overturns the comfortable narrative that choking is about anxiety or lack of preparation. It is neither. It is a collapse in motor preparation triggered by over-motivation -- the neural equivalent of a system overload at the exact moment the stakes demand peak output (Smoulder et al., 2024, Neuron).

If you are a founder who has ever walked into a Series A pitch knowing everything cold and still blanked on your own unit economics, this paper explains what happened inside your skull.

Neural Collapse

Motivation improves performance -- up to a point. Increasing the reward signal sharpens neural discriminability: the brain gets better at distinguishing between successful and unsuccessful movement patterns. Your pattern recognition tightens. Your decision-making accelerates. You become, in every measurable sense, sharper.

Beyond that threshold, the excessive reward signal induces what the researchers call a “spread” in neural activity -- motor preparation diffuses away from the precise neural region that produces successful execution. The brain does not shut down. It does not freeze in the way we colloquially describe stage fright. It actively reorganizes itself into a less effective configuration. You are not failing to try. You are trying so hard that the trying itself degrades the machinery.

Consider the inverted-U of confidence the performance literature has documented: overconfident athletes reduce preparation effort, develop arrogance that impairs coachability, and underestimate opponents. But under-confident athletes hesitate, second-guess, and withdraw. The sweet spot is calibrated confidence -- realistic, not maximized (Lochbaum et al., 2022, International Journal of Environmental Research and Public Health). The same inverted-U applies to motivation itself. You need enough to perform. Too much, and the neural preparation collapses.

Practice Can Paralyze

Paradoxically, the expertise you develop can make things harder for you when making a decision. Experts store skills as implicit programs. Years of deliberate practice compress complex decision chains into automatic routines that execute without conscious oversight. This is what expertise is -- the conversion of effortful, step-by-step processing into fluid, chunked execution. Much of the performance of the world experts in a field happens from years of repeated, deliberate practice that more or less makes the finest details of their craft more or less unconscious - i.e. the repeated behaviours become more or less engraved in your own psyche.

Under high-stakes conditions, the brain shifts from automatic to explicit processing. You begin consciously monitoring the routines that were running perfectly well without supervision. And this monitoring -- this well-intentioned attempt to ensure everything goes right -- is precisely what causes it to go wrong. Beilock’s research demonstrates that pressure triggers explicit monitoring of proceduralized skills, which “de-chunks” integrated sequences into their component parts, degrading the speed and fluidity that define expertise (Beilock, University of Chicago).

That moment you start second guessing yourself is not because you were under-prepared. You were over-monitoring. Your expertise was intact. Your conscious mind just decided to supervise it into dysfunction.

Here is the counterintuitive point: a mild distraction -- humming a tune, counting backward, focusing on a single external target -- actually improves expert performance under pressure. Because the distraction occupies the conscious mind just enough to prevent it from interfering with the automatic routines that produce expert execution. The expert performs better when part of their attention is elsewhere.

“Highly skilled golfers are more likely to hole a simple 3-foot putt when we give them the tools to stop analyzing their shot, to stop thinking. Even a simple trick like singing helps prevent portions of the brain that might interfere with performance from taking over.” — Sian Beilock

This only works for experts. Beginners have no automaticity to protect. They need conscious control. But for the founder who has done the reps, who knows the material cold, who has built the pattern library through years of experience -- trying harder is the wrong prescription.

And the practice paradox makes this worse: deliberate practice explains less than 1% of performance variance at the elite level.

A landmark meta-analysis by Macnamara, Moreau, and Hambrick examined 34 studies involving 2,765 athletes and found that once you reach the top tier, everyone has accumulated enormous practice volume. The variance between top performers is driven by factors beyond practice -- psychological traits, perceptual-cognitive abilities, and the capacity to perform under conditions that disrupt automaticity (Macnamara et al., 2016, Perspectives on Psychological Science).

Among experienced founders, the same holds. You have all done the reps. You have all built the pattern libraries. What separates you in the room where the stakes are highest is not how much you prepared. It is whether your mental preparation survives contact with pressure.

The Two Zones: Flow vs. Clutch

Flow state. The zone. The effortless absorption where time disappears and everything clicks. Csikszentmihalyi’s framework has dominated performance psychology for fifty years, and for good reason -- it describes a real and powerful experience. A 2023 study, the first to focus specifically on flow among startup founders, found that founders enter flow during creative tasks, strategic work, and product development (PLOS ONE, 2023)

But flow has a precondition that makes it structurally unavailable in the moments where you need performance most.

Flow requires challenge-skill balance in a low-threat environment. It emerges when the task matches your ability, when goals are clear, when the context feels safe enough for absorption. Building product in your apartment at 2am. Writing the deck alone in a coffee shop. Debugging a system architecture problem with your co-founder on a whiteboard. These are flow environments.

A Series A pitch is not a flow environment. A board meeting where the company’s survival is at stake is not a flow environment. An acquisition negotiation with a corporate development team that holds all the leverage is not a flow environment.

These are pressure environments. They demand a different state entirely.

A 2025 review in the Journal of Applied Sport Psychology by Jackman, Swann, and colleagues documents a paradigm shift in how researchers understand peak performance. The field is moving from a single-state model to what they call a “multiple states paradigm.” Excellent performance arises from at least two distinct psychological architectures: Flow (effortless, absorbed, no ego involvement) and Clutch (effortful, intense, high deliberate engagement under pressure). Both produce peak outcomes. They run on different cognitive machinery (Jackman et al., 2025, Journal of Applied Sport Psychology).

Flow emerges through positive events and open goals. Clutch states emerge under pressure with specific goals and a conscious decision to increase effort. Flow feels like effortless mastery. Clutch feels like controlled intensity. Both are legitimate paths to excellent performance.

You can’t use flow to deal with clutch situations. Many founders will naturally try to relax into unknowns and threats. They try to find the zone. They try to make the high-stakes pitch feel like building product. And when the effortless absorption does not arrive -- because it cannot arrive in a threat environment. They are choking because they are trying to reach the wrong zone.

The founders who perform best in high-pressure moments are not the ones who have learned to make every situation feel like flow. They are the ones who have learned to operate in Clutch: deliberate, aware, effortful, and fully engaged with the pressure rather than trying to transcend it.

The data on emotional suppression confirms this. Research shows that athletes who suppress emotions -- the “tough it out, show nothing” approach in locker rooms -- produce less power output and report more physical exhaustion than those who acknowledge and regulate through reappraisal or acceptance. Suppression consumes the same executive function resources you need for performance. The stoic founder archetype -- the one who walks into the room projecting unshakable calm while internally fighting their own nervous system -- is not just psychologically costly. It is measurably counterproductive (Dr. Paul McCarthy, 2025).

Clutch is not suppression. It is engagement. It acknowledges the pressure and works with it rather than pretending it does not exist.

Sports Insights for Founders

I suspect the inner life of athletes and entrepreneurs are more similar than different. Here are 5 findings that are directly actionable in your own life. Small and simple shifts in your thought patterns can make a huge difference in your own ability to remain calm and able under pressure.

Reappraise anxiety as excitement

Over 90% of people, when they feel pre-performance anxiety, instinctively try to calm down. This is the inferior strategy. Alison Wood Brooks at Harvard demonstrated that saying “I am excited” -- out loud, literally one sentence -- before a high-stakes performance shifts the cognitive appraisal from threat to opportunity and measurably improves outcomes across singing, public speaking, and math. Anxiety and excitement are physiologically identical -- same heart rate, same cortisol, same sweaty palms. The only difference is the label. Trying to calm down requires a costly downshift in arousal. Relabeling as excitement preserves arousal congruency and redirects it toward approach motivation (Brooks, 2014, Journal of Experimental Psychology: General).

Focus on external cues to get out of your head

A review of approximately 100 studies by Gabriele Wulf found that externally focused attention -- on the effect of the action rather than the mechanics of the body producing it -- consistently produces superior performance across nearly every motor and cognitive task studied. Internal focus (”Am I speaking clearly enough? Am I making eye contact? Is my body language right?”) activates conscious monitoring of automatic processes. External focus (”What is the investor’s key concern? What decision am I driving toward? What does this person need to hear?”) lets the trained system execute while directing conscious resources where they belong (Wulf, 2013).

In the middle of a pitch that matters most, stop auditing your performance. Start tracking the room.

Use strategic distraction before the highest-stakes moment.

This is the hardest one to accept, because it violates everything we have been told about focus and preparation. But Beilock’s research is clear: for experts, a mild cognitive distraction in the moments before execution prevents the conscious mind from hijacking automatic routines. Count backward from seven. Hum a melody. Focus on a single sensory detail in the room -- the temperature of the water glass, the texture of the table.

By doing so, you are protecting your automaticity from your own conscious interference. The founder who walks into the biggest meeting of their career thinking about what they had for breakfast may outperform the one who spent the last twenty minutes in intense mental rehearsal -- because the first founder’s expertise can run without a supervisor.

Talk to yourself in third person.

Research by Ethan Kross and Jason Moser demonstrates that third-person self-talk reduces emotional reactivity within one second, without engaging any additional cognitive control systems. EEG data show a rapid reduction in brain-potential markers of emotional reactivity, and fMRI confirms it happens without increased prefrontal control activity. It produces psychological distance at essentially zero cognitive cost. It is fundamentally different from suppression or forced positive thinking, both of which consume mental resources you need for the task itself (Moser et al., 2017, Scientific Reports).

Write about your worries for ten minutes before you walk in.

Anxious thoughts consume working memory -- the same finite mental workspace that runs your decision-making, your recall, your ability to think on your feet. When the working memory is occupied by suppressed worry (”What if they say no? What if I forget the numbers? What if they see through me?”), there is less bandwidth for the actual task. The expressive writing protocol developed by Ramirez and Beilock is brutally simple: ten minutes, pen and paper, write out every worry. The act of writing externalizes the anxious thoughts, freeing the cognitive bandwidth they were consuming (Ramirez & Beilock, 2011, Science).

Before an important meeting or presentation, find ten minutes and a piece of paper. Write out everything you are afraid will happen. Then fold it, put it in your pocket, and walk in with a working memory free of worry mind chatter.

Handling Pressure is a Skill

“The most exciting part of my work is showing that you can get better at things with practice... The idea that you’re not born a choker or a thriver, that everyone has to practice.” — Sian Beilock

Mental pressure is a stressor on your system - just like heavy weights are stressors for your muscles. With the right dose and approach, that pressure can deliver improvements that lead up to becoming less susceptible to neural collapse in high stakes moments.

“People say to me all the time, ‘You have no fear.’ I tell them, ‘No, that’s not true. I’m scared all the time. You have to have fear in order to have courage.’”

Next time you feel like seizing up, ask yourself what lies on the other side of you fears.

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.

Read full list

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.

How did you like this post? What do you want to read about? Please share and I’ll add you to my secret list for exclusive posts and thoughts.

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

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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.

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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.

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“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.

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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.

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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 ✌🏼🎄

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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 ✌🏼

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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 ✌🏼

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