The Dark Side of ADHD in Entrepreneurship
The dark side of the Kinko’s story is that the company was built, at least in part, on emotional extremes, most of them my own.” - Paul Orfalea, founder of Kinko’s
Paul Orfalea built Kinko’s into a $2.4 billion company. He was expelled from four schools, graduated eighth from the bottom of his class of 1,200, and was fired from every job he held — including scooping ice cream. He has both dyslexia and what he describes as “ADHD to the max.”
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:
Hyperfocus phase: Intense, productive, euphoric. Hard work feels fairly easy.
Overcommitment: Can’t say no because each new commitment delivers a dopamine hit.
Exhaustion: Executive function goes offline. Not just tired — cognitively disabled.
Crash: Full shutdown. The kind of burnout that isn’t fixed by a vacation.
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
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).