A year or so back I got fired from my startup. I was the first co-founder. I’ve been struggling with my sense of identity and purpose since. Tonight I hosted a solo-founder dinner at my place; six seats, half gals, half guys, all people I’ve either gotten to know or really connected with in the time since.
The rules were simple; everyone here has committed to founding a company and everyone here is without a co-founder. In South Park Commons terminology, we aren’t quite in negative one and we aren’t quite at zero. We’re somewhere in the messy middle. Only one pair had met each other outside of tonight; it was a cold open and I flubbed it. One of the gals gave us a push, Rose & Thorn, and jumped in seeking romantic relationship advice. Vulnerability and grit in equal measures. Our resident romantic, a man I’ve known for over a year but haven’t every truly connected with, weighed in with stark wisdom and a tone that said more about how he’d earned it than any story could’ve.
Another of the gals, she’d just moved into the city, explicitly to build her startup. She’d flown in from Dallas after hoofing it at an industry conference for half a week. She’s not LARPing; none of us are, but we’re all alone. We welcomed her to the city, and though she was last to answer the prompt, and the night was taking its due, the group stayed to hear her tale.
We talked about why we do this; why do we build companies. Is it that our needs were unmet as children? Is it an immortality project? Is it a chip on our shoulder? Are we broken? Hands go up. Debates are had. We dive down rabbit holes and offer advice. We challenge each other. Our resident philosopher walks us through the five defining fears: insecurity, stagnation, failure; I’ve forgotten the others. Maybe I wasn’t afraid of those? We stack rank them, we caveat them, we drink wine and smoke vapes. We talk about addiction. We talk about psychosis, family trauma and boxing. There was 7.5lbs of flat iron steak and somehow it’s dwindling.
Frameworks are exchanged, debated, and discarded. The Learning Engine is debated alongside the cost of failure. Those of us with expectations of performance in our upbringing cringe and buck under the idea that failure is inevitable, healthy, and required. Someone asserts that people are not kind and our boxer says you need to fight and defend yourself. I say they’re wrong, I take the table and I fight the finality, the binary nature of it. They let me rant, they sooth me, they point out the nuance, I thank them and cede the topic and the mic.
We talk about the co-founder search. The petty fights. The relationships we’ve lost in the hopes that friends or family could be that ally. We lament the cost of it all. Some of us think we work better with a partner; others are silent. The cost of a co-founder; the distraction of searching, the value of success, the phases of leadership, what it means to be CEO. It flows alongside the wine, the nicotine, the lights dimming because I forgot to turn off the timer that usually sends me to bed on time.
It’s interesting to reflect on what we didn’t talk about. Runway. Traction. Risk. Go To Market. AI. Some simply weren’t mentioned, others were a footnote or an asterisk at best. I’ve heard about SF founder dinners. I’ve hosted a couple. I’ve never achieved this level of intimacy; of openness, of tolerance and space.
We’re all motivated by something; and some of us don’t yet know what it is. If there’s one thing tonight has made clear to me it’s that the old adage “Powerful people have command over others. Great people have command over themselves.” is true.
Thanks friends.