Note: The following is a first-person narrative inspired by real challenges common to entrepreneurs and patients navigating mental healthcare. It is a work of creative nonfiction; details, identities, and timelines have been altered. It should not be read as a factual account about any specific individual associated with TOMS.
After I sold TOMS Shoes for $400 million I was misdiagnosed with bipolar disorder — and it almost cost me everything
The day the wire hit my account, everyone told me I should feel triumphant. Friends sent champagne. Journalists wanted quotes about purpose. Advisors urged me to take a victory lap. The deal we had spent years courting had closed. The brand I started out of a backpack and a camera bag had become shorthand for do good, buy better. We built clinics, delivered shoes, and inspired a generation of founders to put meaning in their margins.
But when the applause faded, something in me broke loose.
For a while it looked like energy. The sale validated a thesis that had consumed my twenties and thirties. I flooded the calendar with plans: a new fund for social enterprises, a documentary, a retreat center. I said yes to every conference. If there were 24 hours in a day, I would use 25. I slept four hours a night, sometimes two. I started waking with my heart sprinting and a mind that felt like it was typing six different sentences at once. To quiet the static, I’d run ten miles at 5 a.m., then open my laptop while still drenched in sweat.
To friends and investors, it was familiar: classic founder mode. Work would make the noise go away. But the noise doubled back. My patience thinned. I spoke too fast and interrupted people I loved. I made impulsive decisions I’d never have tolerated from a first-time manager, let alone myself. I cried in an Uber on the way to a keynote, then walked onstage and told 3,000 people that everything was great.
A week later, after two nights without sleep, I stood in my kitchen staring at the sink and couldn’t remember how faucets worked.
I got help — or so I thought. A friend connected me to a psychiatrist who saw founders and C-suite clients. He met me after hours, took a quick history, and scribbled in a notebook while I described the past month. He asked about family history, substance use, risk-taking. He asked how often I felt “on.” Then he closed his notebook and said four syllables that stitched themselves into my identity: “This is bipolar.”
I nodded. If there was a diagnosis that explained my alternating superpowers and meltdowns, I was ready to accept it. He prescribed a mood stabilizer, suggested an atypical antipsychotic “just to smooth things out,” and told me we’d talk about therapy later. He encouraged me to think of bipolar as a gift and a discipline: the same thing that might have powered my company could be redirected, with the right meds, toward my next act.
Within a week I felt like someone had stuffed wool into my skull. My mornings, once a sprint, became molasses. I gained twelve pounds. My inbox gathered flags like a protest. The board I’d just joined wondered why I missed two meetings. My partner asked if we could talk about the way I seemed to disappear into blank spaces in the middle of conversations.
I doubled down. If the prescription was right, then the side effects were my price of admission. I told myself that “stable” meant good. What I didn’t say out loud: I couldn’t write a coherent paragraph. I’d start a sentence and watch it wander into a cul-de-sac. The creative spark — the improvisational thread I’d followed through dusty villages, pitch decks, and pop-up shops — flickered. At night I lay still, hearsay spiraling: You’re broken. You were never the visionary; you were an accident. This is who you really are without adrenaline.
Two months later, the press ran a profile about my “post-exit awakening.” I stared at the headline and felt like a fraud. In private, things were breaking. I forgot my niece’s birthday. I bailed on a volunteer trip. I rescheduled couples therapy and then skipped it without calling. When my partner said, “I can’t do this anymore,” I felt something shatter that the medication couldn’t blunt.
It took a second opinion to slow the free fall.
A longtime mentor — grizzled, kind, unfooled by myths we tell about founders — listened to my story and asked a single question: “How many hours were you sleeping, really?” He sent me to a clinician known for diagnostic workups that last longer than a PowerPoint. Over the course of a month, she coordinated with my primary care doctor, ordered labs, reviewed my travel records, spoke with my partner and two colleagues, had me wear a sleep monitor, and had me track my mood four times a day. Nobody had ever looked at my life like a data visualization. It felt invasive. It also felt like care.
Here’s what we found: my thyroid was out of range, likely swinging for months in a way that can mimic anxiety and agitation. My resting heart rate was elevated. My sleep was shattered. Caffeine, which I once treated as a harmless productivity tax, had escalated into a quiet dependency. I wasn’t cycling through mania and depression. I was burning down the wiring that kept my mind and body communicating honestly.
Did that mean I didn’t have bipolar disorder? It meant we didn’t have enough evidence to call it that. Bipolar is a clinical diagnosis that depends on observing discrete episodes over time, history, and collateral information. My first psychiatrist had seen me at my most depleted and most wired and connected dots that fit a familiar picture. The picture might have been right someday; it wasn’t right then.
We tapered my medications carefully under supervision. We treated the thyroid issue. I started cognitive behavioral therapy for insomnia and, for the first time since high school, protected sleep like a core meeting. I cut out caffeine for a month. I learned how to tell the difference between a surge of inspiration and a red flag. “Become a student of your nervous system,” my therapist said. “You’ve outsourced that job to your calendar.”
The sensation of my mind clearing was not cinematic. It was slow. One morning, I wrote a page in my notebook and didn’t hate it. I noticed a tree on my block I’d never really seen though I’d passed it a thousand times. I apologized to my partner without justifying myself. We didn’t fix everything in a day. We held hands while we waited to see which version of me would come home from the clinic.
Here’s what nearly cost me everything wasn’t just a misdiagnosis. It was the willingness — eagerness, even — to grab a definitive label in a moment of panic because it offered certainty. It was the speed of the system that served me. The same concierge medicine that gave me access robbed me of friction. In the space where questions might have lived, I got a prescription.
Entrepreneurship makes this worse. Founders are rewarded for leaning into extremes. Investors love velocity. Customers love spectacle. Teams love clarity. When your company’s identity fuses with your own, any physiological state that gets you to a metric can feel like a virtue. The first time someone called me a machine, I smiled like they’d seen my truest self. Machines don’t need sleep.
I don’t blame the first doctor. He saw a pattern. He tried to help. I do think we need a different playbook for high-output performers in crisis. We need intake processes that privilege longitudinal assessment over quick categorization, especially for diagnoses that carry a lifetime label. We need integrated care that screens for medical mimics of psychiatric symptoms — thyroid conditions, sleep disorders, medication effects, substance use — before we put someone on meds that can dull the very capacities their work and relationships require. We need to normalize second opinions in mental health the way we do for cardiac surgery.
And we need founders to stop treating ourselves like exceptions to biology. The mythology of the sleepless visionary doesn’t just burn people out; it blurs the boundary between trait and symptom. Hypomania is not a strategy. Insomnia is not a brand.
There’s a version of this story where I lose the company I was incubating, alienate the people I love, and wind up in a profile that turns my unraveling into pulp. I brushed up against that. A board seat went to someone else. A friend I’d known for twenty years stopped returning my texts. The team I’d just recruited started asking whether I could be present for a full day. The word liability snuck into conversations.
What saved me wasn’t grit. It was humility, and the right kind of help. It was a partner who set boundaries and stayed anyway. It was a mentor who believed curiosity is a form of care. It was clinicians who asked better questions than, “Does this sound like you?” It was the admission that I’m not a brand; I’m a person whose brain lives in a body that keeps score.
I still wrestle with identity in the aftermath of that sale. Money didn’t solve the problem of who I am without the chase. It did strip away excuses. I’m learning that purpose isn’t a stage or a press release. It’s taking my vitamins and telling my team I’m logging off. It’s texting my niece a dumb meme on a Tuesday because she’s twelve and memes are love languages. It’s investing in founders and asking about their sleep before their burn.
If you’re an entrepreneur reading this and some part of your chest tightens with recognition, here’s what I wish someone had told me on day one:
– Don’t diagnose yourself with a thread you saw on social media, or let a single 50-minute session define your life. Seek comprehensive, integrated care.
– Treat sleep like an unbreakable contract. If the people around you celebrate you for breaking it, reconsider who’s around you.
– Check your labs. Rule out medical causes. Drink water. Take a walk without your phone.
– Build a small circle who can tell you when your “best” looks scary. Believe them.
– If you do start medication, do it with a plan, a timeline, and informed consent. Know what you and your clinician are trying to treat.
– Remember that you are not your output. Your company needs your judgment more than your velocity.
TOMS taught me that business can be a vehicle for generosity. This chapter taught me that generosity has to start at home. I nearly lost the people and work that matter most to me because I confused a story about myself with the truth of my body. The label wasn’t the enemy. The rush to wear it was.
I used to wrap up speeches with a flourish about changing the world. These days I end with something smaller and, for me, harder: Go to bed. Call your doctor. Ask for help. The morning after I finally slept eight hours, I stood in my kitchen, turned on the tap, and watched water flow like a miracle. It still does.
