Lesson 1: Do the work that doesn’t look like work.

Despite your wildest career dreams coming true, you’ll feel empty inside, devoid of the passion, joy, and clarity you once had. For most of your life you’ve dismissed mental health, therapy or rest as optional luxuries for “soft” people. Founder CEOs aren’t soft. Just “be stronger.” Six years in, life loses its color. After the umpteenth consecutive weekend hiding from the world, lying in bed all day and stress eating your unfelt emotions, you’ll start wondering… This doesn’t seem normal. Am I depressed? What is depression? You’ll wear a brave smiling mask Monday to Friday while feeling lost and hopeless for another six years. What’s the point of life? Why do I exist? The burnout doesn’t help.

Looking back, you’ll see so clearly that everything was happening for you, not to you. Because you avoid conflict, intense conflict will find you. Because you struggle to feel your feelings, your heart will be cracked open. Because you’ve searched for meaning and worth outside yourself, you’ll be forced to look within. Who am I? What are my values? Why do I exist? Do I love myself unconditionally? All your healthy and toxic patterns are rooted in these questions. Nonjudgmental self-curiosity is your friend. Excavate your subconscious. It’ll be scary and uncomfortable. Your ego will resist. But it’s worth it. You’ll learn that fear is expensive for business. That much of your suffering is self-inflicted and preventable. And that your best leadership comes from love and service. And sometimes, love demands the uncomfortable action you’ve been avoiding - firing someone, saying no to a board member, etc.

All the business stuff - customer acquisition, fundraising, building an executive team, etc - is important. But you’re smart and scrappy. You’ll figure it out. The most impactful (and most challenging) opportunities are within. The highest-return work won’t look like work at all - rest, journaling, community, therapy, meditation, etc. Anything that helps you shift from fear to love. Self-mastery is the ultimate game. Do the inner work.

Lesson 2: Cry More. Seriously.

Heavy is the head that wears the crown. Your decade as CEO will feel terribly lonely. You will carry a lot and hurt in silence. You’ll be world-class at shoving your emotions aside and distracting yourself with work. Unfortunately, emotional debt collects interest. It will fester in your subconscious, manifesting as addiction, insomnia, passive aggressiveness, exhaustion, resentment, and other toxic behaviors.

At your 2019 annual sales kickoff you’ll watch two hundred colleagues crush it with their presentations and workshops. You did very little, and yet all the right things happened. It feels incredible. As you bring the kickoff to a close with a few words, you’ll be overwhelmed with gratitude and pride. You’ll unexpectedly burst into tears in front of everyone. Yikes! How embarrassing! Strong CEOs never cry. You’ve cried maybe five times in your whole life. And yet, multiple colleagues will share that they’re ready to run through walls because of your vulnerability. And it feels good to let it out. What’s going on? Eventually you’ll learn a timeless leadership truth - people follow hearts first. Minds second.

All your life you’ve believed that you have to be perfect and strong. That only weak people show emotions. Fear has conditioned you to guard your heart with toxic positivity. The 5 Dysfunctions of a Team will teach you that teams need trust and healthy conflict to achieve great results. And what builds trust? Vulnerability. Teams that seek and speak truth instead of harmony outperform those that do not. When you own your messiness and name your emotions out loud, it gives others permission to do the same. Your shared humanity builds stronger bonds and encourages more honest conversations. Programs like Leaders in Tech (based on the legendary “Touchy Feely” Stanford GSB class) will help you develop your emotional literacy. You’ll realize how in your head you’ve been, disconnected from your body, where emotions live. You’ll learn how to identify when you’re feeling sad, angry, proud, grateful, and the full richness of human emotions. You’ll learn how to express those emotions in healthier ways and value their intelligence. You’ll see the gap between what you say/do and how you really feel, and how your inauthenticity hurts yourself and others around you. In these moments, your heart already knew what to do - fire someone sooner, say no, ask for help. Your mind was just too preoccupied to listen.

Eventually you’ll learn that there’s nothing braver than asking for help. That the people who love you will show up for you in ways you didn’t believe you deserved. Just talking about stuff helps. As you share your deepest darkest secrets and cry more, it gives others permission to do the same. Turns out you’re not the only one who’s fighting a battle. Suddenly the journey doesn’t feel so lonely.

Lesson 3: Surrender.

Your harsh inner critic will drown out your inner cheerleader. Building a billion dollar company won’t make you happy. You’ll meet wildly successful business leaders with all the money, power, and status. And yet, they are miserable. Joyless. Friendless. Addicted. Unkind. You used to crave what they have but now it doesn’t seem so appealing. Deep down, a tender, knowing voice whispers. Something needs to change. Maybe it’s time to redefine success. You’ll wonder if it’s time to step down as CEO after sprinting for a decade and hitting a wall. But your stubborn ego will be too scared and proud to let go. And it certainly doesn’t like big change. Your company, your role, and your identity are now one and the same. People won’t like me if I’m not a CEO.

Sitting with ayahuasca in the darkness of the Mexican jungle will give you the tough love you need. It will be the most challenging experience of your life, ten times more so than building a company. This is the deepest darkest stuff that you’ve been avoiding your whole life. The deepest, darkest emotions you've avoided your whole life: resentment, anger, sadness, shame, and guilt. It’s time for your ego to die. The caterpillar must enter the void so that the butterfly can emerge. But your ego is white-knuckling and not letting go.

The plant medicine is wise and powerful beyond comprehension. She may be tough, but she always wants the best for you. She holds up a fierce yet compassionate mirror of truth that you cannot lie to. After much reflection, the medicine helps you realize that business is just a game. Your self-worth is not tied to your job title, company valuation, or employee count. The medicine shows you how much you people-please. You never needed approval from others. It’s okay to say no and be disliked and rejected.

Stop trading your truth for false harmony. Clear is kind. And kindness is king.

You’ll realize that you’ve always done your best, even when it didn’t feel like it. And so is everyone else. If you could have done better or differently, you would have. Giving yourself and others more grace does not lower your standards. With more reflection and medicine, the master lesson reveals itself.

Everything you needed was already within you. You didn’t have to achieve, perform, please, or prove. You were, are, and will always be a human being, not a human doing.

You belong. You are worthy.

Love? You mean that messy, mushy emotion that we can’t objectively measure? Yes. At first glance, love may seem antithetical to business. How do rainbows and peace signs win in a cutthroat corporate world? I challenge this framing of love. Love can be fierce and tough. And sometimes, it must be. Fear seduces us into short-term comfort and distorts everything. Love endures short-term discomfort in service of long-term flourishing.

I often confused fear with strength and responsibility. I now see how many of my well-meaning decisions negatively impacted our business. In my weakest moments, I’d default to the easy choice, not the right one. For example, I’d hire an incredible leader who’d deliver amazing outcomes in their first few years. But as our business scaled into a different stage with different needs, they’d struggle to adapt. Despite clear feedback, it was no longer working. It was time to part ways. (Side note: these were the most heartbreaking moments of my career). But my fear delayed the decision for months. What if they took it poorly and spoke ill of me? What if their loyal reports follow them out? What if they join a competitor? What if I can’t find the right person to fill their shoes? How will I find the time to manage their team in the interim?

If I really loved this person, I’d want them to be in an environment where they’re set up for success, working for someone who believes in them. If I really loved my team, I’d find the right leader for them, now. If I really loved everyone, including myself, I wouldn’t waste more precious time. In that moment, love demanded courage. Love demanded having the hard conversation now, despite the pain. Not acting sooner was cowardly. It also signaled low standards and a lack of accountability. My avoidance hurt my team and company, and cost us hundreds of thousands of dollars or more.

My pattern of toxic avoidance and attachment repeated itself in different forms.

• I waited too long to step down as CEO. Despite struggling with severe burnout and depression for several years, I kept grinding as if everything was okay. I’d put on a cheerful mask in the morning and come home exhausted in the evenings. The bad kind of tired. I was terrified of losing what had become my primary source of identity and self-worth. My ego also led me to believe that the business would fail without me. During this period I made many suboptimal decisions. My team deserved a leader who could think clearly and give 100%.

• I sometimes didn’t speak up for fear of displeasing others and/or looking stupid, especially in my boardroom. I struggled with impostor syndrome. What do I know? These successful people I admire and respect must know better. I now realize that while it’s important to keep an open mind, usually no one knows their business better and cares more than its founder(s). Some of our missteps might have been avoided had I more fiercely advocated for myself.

• I focused almost exclusively on what could be improved and rarely praised others. I feared that celebration would make us complacent. One company-wide survey highlighted a common theme around lacking pride in our accomplishments. Nothing was ever good enough. One particular comment has stayed with me - “Jason walks around the office with a scowl on his face. He seems stressed or pissed off a lot.”

Fear shows up everywhere in business.

• Fundraising. I’m scared to share my true vision ➡️ Investors fund a version of the company that I’m not all-in on

• Hiring. I’m scared that I won’t ever find the right candidate ➡️ Settle for someone who doesn’t actually want to be here

• Sales. I’m scared of asking for more money ➡️ Undersell our value

• Product. I’m scared of shutting down a product that isn’t working ➡️ Keep wasting precious resources

• Management. I’m scared of looking bad ➡️ Perpetuate a culture optimized for optics over learning and truth

Whether it’s changing customer needs, ruthless competition, constant rejection, layoffs, investor pressure - the reality of business is not for the faint of heart. There is some truth to Andy Grove’s famous line: “Only the paranoid survive”. Many espouse the killer instinct necessary to compete against those who would eat your lunch. The founders and CEOs I coach often ask “Will leading with love make me complacent? Will I lose my hustle?” This assumes a false tradeoff between love and hustle. The right question is “Is my hustle fueled by love or fear?”

Hustle, high standards, competitiveness, grit, ambition, etc. are not inherently good or bad. It’s about the fuel. Fear burns hot. Love burns long. Through this lens, every behavior has its healthy and unhealthy manifestation.

Both my fear and love shaped our culture and decisions. Dirty fuel can feel so good. In the moment, it feels comfortable and addictive. But eventually, the piper must be paid. Fear can win the quarter. Love wins the decade.

In that moment, I forced a smile. We had won the lottery. My 25-year-old self was grinning ear to ear, his wildest dreams exceeded. And yet, somehow I felt empty. Why isn’t this enough? If exceeding my wildest dreams doesn’t make me happy, what will? I had chased this goal for a decade, ready for the pot of gold at the end of the rainbow. Surely, this success would make me feel worthy. Surely, I would belong. Unfortunately, it was a mirage. I couldn’t fill the hole in my heart with more of what created it.

In that same week, my friend Brian was taking Coinbase public at an $85 billion valuation. I was thrilled for Brian. He gave us a shot when he was an engineer at Airbnb, who then became our first customer. Back then, Airbnb was “just” a billion-dollar company. When he left to start Coinbase, I recommended him into YC. Coinbase then became an early customer and helped us a lot. Without Brian, our trajectory might’ve been very different.

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But as I received notes of congratulations that week, all I could think about was how Coinbase accomplished so much more than us in less time. I didn’t build what Brian built. My billion-dollar company isn’t enough. I’m less than. I was fixated on what was missing, unable to appreciate all the good in my life. Comparing myself to others instead of my past self meant that even miracles were never enough. I had defined winning and losing within a finite game. The problem wasn’t the goal. It was that I kept moving it. I didn’t need a bigger win, I needed a different source of self-worth. Tying my self-worth to external measures like valuation was a recipe for misery. I’m certain that if we went public at an $85 billion valuation, I’d compare myself to businesses trading at a trillion-dollar valuation. I’d still feel inadequate.

Nothing in life is free. Every version of success comes with a cost. The question isn’t whether we’ll pay. It’s whether we’re conscious of the price. After a decade of sprinting as CEO, I was most depressed and burned out when we became a unicorn. I had gained more than 100 pounds from stress eating and not exercising. I did lasting damage to my body. I skipped family vacations and friends’ weddings and birthdays. My identity as a competitive, successful winner improved my local maximum at the cost of my global one. I had won on one dimension, but lost on many others. Was this winning? Was it worth it?

I didn’t invent my take-no-prisoners drive. It blossomed from my culture. Moments of praise (or lack of it) and criticism. An A wasn’t enough. It had to be an A+. I built a belief that my worth had to be proven. That success meant becoming someone. That if I had no value if I wasn’t producing. While I have no regrets, it’s now clear that I wasn’t really in the driver’s seat. Much of my journey was driven by my subconscious fear, ego, and scarcity mindset. So of course I couldn’t feel happy when we became a unicorn. Of course I burned out and struggled with depression. When we run on dirty fuel, the engine eventually breaks.

Ambition is healthy. It keeps us hungry. But ambition without enoughness is a toxic bottomless hunger that cannot be fed. “I’m not enough. I need more.” Some may contend that enoughness and ambition can’t coexist. This confuses enoughness with toxic complacency. Enoughness is the healthy soil from which sustainable, meaningful ambition emerges. There’s no tradeoff. We can believe both “I am enough” AND “I want more - but I don’t need it”. We should strive for greater heights - but from a place of love, service, and abundance, instead of fear, ego, and scarcity. Clean vs. dirty fuel.

These days, I try to approach work with less to prove. I’m still wildly ambitious, but I try to be less attached to the outcome. I’m trying to be kinder to myself and celebrate every moment. I still catch myself slipping back into old patterns… it’s not easy to rewrite my operating system from within. It’s like unlearning a language I’ve spoken my whole life. If I could go back in time, I’d tell my younger self that it’s OK to want to win - you just don’t need to. You’re enough as you are, forever and always. ❤️

My productivity obsession was fear and ego wearing a costume. I needed to be seen as a hard worker. It was my identity. I derived self-worth from it. I was scared of being judged as lazy and uncommitted. Truthfully, I was already judging myself. I wore my nonstop back-to-back calendar like a badge of honor. I stacked my trophy case with 80+ hour weeks. I got drunk on busyness. Almost always last to leave the office. Look at me, I’m working so hard. I’m setting a good example for my team. But by the end of the day I was too tired to do meaningful work. I’d just mindlessly scroll Slack. Read articles. Stare at a blank screen. My time would’ve been better spent resting, exercising, or seeing friends.

Even rest felt uncomfortable. If I’m not grinding, I’m failing. I’d step away but never truly unplug because a good leader is always there for their team. After nine years of sprinting as CEO, I finally took a six-week sabbatical. “Call me if there’s an emergency.” When I returned, my colleagues said that I was a different person. Calm. Positive. Thoughtful. Energized. Unfortunately, it wasn’t enough to fully refill my tank. My burnout and depression were irreversible. Elite athletes treat rest and recovery as part of the work. We should too.

As we scaled, my need for control and maniacal attention to detail worked against me. I focused on everything, which meant that I focused on nothing. Yes, sometimes Founder Mode is needed. But I wanted perfection everywhere. I’d send a 2 AM email calling out a typo in a support ticket. Occasionally, it was a good use of my time. More often, it was a toxic outlet for my stress, anxiety, and insecurity. I bottlenecked my team. More hours. More context switching. Less impact. Local maximums over global ones.

Now I ask leaders three questions:

1. Have you ever had a day where you got more done than an entire week?

2. If we audited your past quarter, what % of your hours actually moved the needle?

3. How would you work if no one rewarded busyness?

We say we value results. But we often signal that we value activity and visible effort. We reward the fastest reply, not the best thinking. The loudest voice, not the insightful question. The firefighter, not the one who prevented it. Winning over learning. Our teams optimize accordingly. And we wonder why we’re not moving the needle.

Hours worked is a vanity metric. We currently optimize Time ➡️ Impact. This is broken. When the Time vs. Impact curve goes sublinear, the solution isn’t more hours. It’s to change the slope.

The real equation is Energy ➡️ Impact. When we’re not feeling inspired, focused, and creative, we shouldn’t force output. We should change state. Travel. Dance. Watch a movie. Meditate. Whatever it takes to get back to flow.

To be clear, I’m not anti hard work. I’m a fan of 100 hour weeks if we’re in flow. If we’re inspired. But mindless low-impact work is just motion without progress. A traditional 40+ hour week isn’t discipline. It’s an Industrial Age ghost haunting our Creative Age. Stop clocking in and out. Start compounding impact. Or don’t. Just be honest about what it’s costing you.

Side note. Last year I was diagnosed with severe ADHD. “A Ferrari mind with bicycle brakes”1. It means that my attention scatters, and so does my impact. A task that should take an hour might take two. I’m honestly impressed that I was as successful as I was. And I would’ve been even more successful if I had gotten help sooner. I suspect many founders are in the same boat. Neurodivergence is both a superpower and a liability. I encourage proactive diagnosis, and if you have it, learn how to manage its downsides. Knowledge is power!

I stepped down as CEO at the end of 2020 after nine years of sprinting. Looking back, I wish I had the courage to do so sooner. More importantly, I wish I’d worked in a way that didn’t burn me out. We obsess over markets, strategy, and competition. But the biggest risk to my company wasn’t any of those. It was me. I now believe that burnout is the greatest destroyer of enterprise value.

To be clear, I have no regrets. I’m insanely proud of our success. I’m also certain that we would’ve been even more successful had I worked more sustainably. Unfortunately, almost every founder I know also burns out. As our companies become more successful, we lose our creativity and joy. We become shells of our former selves. It doesn’t make sense. Our customers, teams, and investors all lose when we can’t play at our best. Imagine Serena Williams or Tom Brady having a career-ending injury at 22 years old.

How I Burned Out

1. I lived a one-dimensional, unbalanced life. I was maniacally obsessed with work and poured every waking minute into it. I couldn’t sleep. My mind wouldn’t stop ruminating. I didn’t make time for family, friends, and hobbies.

2. I denied myself truly restful breaks. I went nine years without a real vacation, convincing myself it was “leadership”. I believed that a real break would make me look checked out and uncommitted. “If I’m not working hard, they’ll judge me as lazy and work less hard”.

3. I tried to control everything. I didn’t trust anyone to do it as well as I could. I struggled to let go of my baby. Even when I “delegated”, it was often with a watchful eye over my shoulder. I needed everything to depend on me. It made me feel important and valuable.

4. I strayed from my Zone of Genius. I believed that a CEO had to do it all and be good at everything. I got stuck in my Zone of Excellence - tasks I can do with sheer willpower but that don’t energize me, e.g. budget reviews, OKR planning etc. I should have focused on what I’m naturally best at - recruiting, visioning, product, etc.

5. I didn’t ask for help. I was so in it. I refused to believe that I needed help. I judged vulnerability as weakness. I wasn’t aware of my unhealthy insecurities and coping mechanisms until far too late. I avoided therapy, peer support, meditation, and other forms of inner work until far too late.

Of course, not all hard work is toxic. And not all obsession is unhealthy. But I was past that point. As my company grew, so did my fear and ego. I sprinted even faster on a hamster wheel of my own creation, optimizing for a local maximum, not a global one. Inevitably, I hit a wall. Game over.

Most founders aspire to build enduring businesses. If we’re lucky, we get to work on something we love for ten, twenty, or more years. But we reward ways of working that make endurance nearly impossible. We forget that the goal isn’t to win the race. It’s to still want to run.