Formidable

“How do you become a successful founder?” I was on the edge of my seat, alert, ears perked up like a puppy.

“Be formidable,” my YC partner said, “Do what you say you will.”

I remember the old YC offices before Garry Tan put them on social media. They're down in Mountain View, over the river and through the woods from Google. Old warehouses and industrial buildings with walls lined with neon orange foam, like an insane asylum built for startup founders.

There were relics, pictures and posters, on the wall. “Make something people want.” A picture of the Stripe founders doing a Collison installation. A line chart of the Trough of Sorrow.

There was something very special about it.

When I think of product-market fit, I think of the YC offices back then. YC did one thing, they picked startups. That's it. It didn't matter if they had flickering fluorescent lights or one-week-old tacos filling 30-pound aluminum trays. They focused on the one thing they were really good at, the one thing that mattered.

At the time, I didn't think about what my YC partner said, I acted instinctually. I thought formidable simply meant grit. If you promise to work out every day, you wake up at 5:30 AM, do a hundred squats, sit-ups, and pushups, then eventually, you become a superhero.

My first idea out of YC was pure grit. Every day, I walked the strangely depopulated streets of San Francisco, wandering into local businesses, interrupting their actual work with a useless sales pitch.

Fortunately, COVID knocked me off my ass. All my customers closed down. And I deferred just weeks before Demo Day.

When I pivoted, I did it on a whim. As Spinoza might say, "There is action, and there is passion." StartPlaying was passion. A COVID-19 baby. Co-founded with a high school friend and a serendipitous user I interviewed.

And we caught fire. We hit hyper growth, bottled lightning that many startup founders would climb a mountaintop waving a 10-foot iron pole to capture.

It was at that point I turned StartPlaying into a living hell (see The Selfish Ideology). I made a catastrophic hire, and learned a valuable lesson. It's only after you steer your ship off a waterfall that you truly know you're at the helm.

Nearly two years after that hire, we were on an off-site in Indianapolis. One so stressful, it induced good behavior, exercising twice a day to prevent a case of chronic pain similar to a repeated kick in the balls.

On the last day, I walked the streets with my co-founders. The city was hollowed out. An American icon laid low by the opioid epidemic. Boarded windows. Empty husks of filigreed buildings.

Devon dragged me and Jared from bar to bar. And I was slowly learning how effective alcohol is as an emotional analgesic. We ducked into this half empty dive and Devon ordered us three High Life’s, nasty things, only tolerable in good company.

We clinked glasses. I tuned out the surrounding voices. I had to make a hard decision.

The catastrophic hire had dragged our company to a standstill and left me with the ominous feeling that it was all my fault. Maybe if I stepped away, bowed out, or handed over the reins, the problems would go away. The pain would stop.

“I feel like we've gotta fire them.”

That night I learned something incredibly important about being formidable. You have to trust those around you. You have to open up. I told Devon and Jared how I felt. And lo and behold, they felt the same thing. They stood behind me, backed me up. They validated me. They helped me make a hard decision.

You see, feelings are signposts. They let us know something's wrong. I had a feeling to pivot during YC, even though our partner recommended doing Demo Day. And I had a feeling we needed to let this employee go.

Feelings aren't reasons. They're not rationales. They're not plans. And acting instinctually on them can cause more damage than what you were initially trying to prevent.

That's why trust is so important. You don't need to say, "I'm 100% going to do X. It’s a guaranteed slam dunk.” All you need to say is, "I’m thinking about X. What do you think?"

You uncap the bottle such that a single mentos doesn't cause an explosion. And you delegate your quixotic thinking to the super consciousness of conversation.

It was at that moment that we were formidable. We made a hard decision. We incorporated good judgment, building out a plan and fallbacks instead of firing on the spot. And we followed through. I did what I said I would.

It took us a month to pull the trigger. And a year to take our leaky trawler and turn StartPlaying into a finely tuned speedboat.

Nothing in the world will give you more confidence and instill a greater sense of agency than creating paradise out of your self-made hell.

We built StartPlaying into something special. The best place I ever worked. By 2025, we were growing and solidly profitable. The team was ecstatic. We were shipping fast, measuring honestly and accelerating our learning loops.

Then I had another feeling. “I'm thinking about leaving.”

I was at a steakhouse with Tom, a friend and mentor from a16z. He smiled and gave me a shoulder hug that only two straight men can pull off with grace, and then proceeded to order every meat on the menu.

Tom helped me talk through this feeling. Just like my co-founders before him, he validated and supported me.

I told him about the catastrophic hire and the lesson that came after. That the more I worked at startups, felt the hard frets of reality against my calloused fingertips, the more I believed success and failure were mine to own.

Tom looked a bit starry-eyed, then leaned over and told me a story.

When Tom was a kid, he worked as a caddy. There was a man that worked as a landscaper at the same golf course called Ciro. He was an immigrant. And that job was one of three he held. He worked 18 hours a day, seven days a week. “If I even worked one day that hard, it would kill me.”

Ciro took those earnings, and remitted them back to his family.

So if grit had anything to do with success, why wasn't this man a billionaire? My argument seemed refuted. Luck seemed to define success, as inescapable as the event horizon of a black hole.

After dinner, I knew what I had to do. I prepped like hell.

Once you make a hard decision, there's catharsis. This feeling of tension in your shoulders slacking. You're ready to rest under your own vine and fig tree. But that's not what I did.

Every previous job, I went in with a better reputation than I left with. I'm not proud of that. This time I wanted to leave StartPlaying in the best state possible. I wanted a win-win for the employees, game masters, players and investors.

And I could do it. All it required was trust and grit.

I built out new CEO MOCs. I ferociously communicated with investors. I created processes that ran themselves.

And I left StartPlaying better than I found it.

I almost tear up writing that. Because it's incredibly hard to do. Because it matters so much. I was so proud and appreciative of many employees telling me that this was the best place they've ever worked. The greatest team and the greatest company.

Six months later, I sat in Marlowe, a little brunch spot in downtown San Francisco. Devon and Jared sat comfortably at my side. We'd been planning the departure for months. I invited Nick, an investor and advisor, to join us.

“Jared and I are leaving StartPlaying.”

“Why?”

Ah, the thrust and riposte. The over-specified question. The dreaded utterance of the 25th.

“StartPlaying doesn’t need me anymore.”

"Don't you own the company? Can’t you make it need you?" Nick looked at me puzzled. "Isn't that just a cop-out?"

I was dumbstruck. I did own the company. Couldn't I make it as challenging as I wanted?

In fact, if I wanted to be formidable, wasn't I violating a promise by not taking StartPlaying to its fruition?

He was right. The answer was a cop-out. Because it wasn't exactly the truth.

I had this strange feeling as I was planning my departure. It felt like I had succeeded. StartPlaying helped thousands of people make a living and created the best gig economy job on the planet. It connected lifelong friends, caused books to be written, officiated a marriage between two members that met on the platform, and, of course, created the first StartPlaying tattoo.

So, there was reason enough to be ecstatic, ebullient.

But wasn't I failing? Wasn't I not formidable? There was this great divide between my conscious and unconscious.

Looking back, maybe this is exactly what I wanted from StartPlaying. Maybe I didn't want to build the next trillion-dollar company, not this time. Maybe I wanted something that would be a win-win for everyone involved.

Maybe unconsciously, I wanted this all along.

I thought back to Ciro, the man that should have been a billionaire. "Maybe what he wanted was to be a good father, a good husband." Maybe consciously or unconsciously, he was getting exactly what he wanted. The same as we all do.

When it comes right down to it, most of us just act on instinct, instead of thinking for ourselves. We ask: “How do I become successful?” Instead of: “Why do I want to be successful, and what does it mean?” We ask our friends and mentors how to achieve something we might not even want.

Instead of consciously confronting hard decisions, we have the world make the decision for us. We slack off at work, waiting for the boss to take action. Or have an affair, forcing the partner into a decision.

Our unconscious directs our lives, and we call it fate.

But being formidable requires being fully awake. Bringing your unconscious conscious. Recognizing what you truly want rather than what you said you did.

Two weeks after Marlowe, I lunched with Nick one more time. This time I explained the truth. Why I was making this decision. We had one of our best discussions, talking about life, the future and what we really thought.

So why am I leaving? I'm leaving because I did what I wanted. I built StartPlaying into a great company. I created a whole new profession. And I helped, really helped thousands of people along the way. I wasn't forced out. I didn't hate my job, in fact, it was the best job I ever had.

I close the door behind me without opening a new one, and plan to fall in limbo until I know what I truly want next. And while I don't know what I will do, I do know what I will be when I find it. Formidable.

Thanks to: Spriha, Brent, Seth, Devon, Jared, Gena and Tom for reading the drafts.