Keep going

The biggest surprise first-time founders experience is the total lack of external validation in their day-to-day professional lives. Working a real job with a boss, if you’re doing a good job, comes with a steady stream of “good jobs” and “attaboys” to validate your progress. Those are then reinforced every year or two with promotions and raises. Meanwhile the company’s headcount growth and successive funding rounds will make it feel (correctly or incorrectly) like your personal success is going hand-in-hand with the company’s overall success.

None of this exists when you start your own company. Folks sometimes assume VCs provide this structure: That there must be some system of milestones, picking winners, and orchestrating follow-on rounds. No amount of telling would-be founders that there’s no “behind the curtain” replaces the experience of realizing it’s just you and the market.

In my experience, the biggest cause of death in early stage startups is founders giving up, and the root cause of giving up is the inability to cope without external validation. I have seen companies truly run out of money, but in my experience that is rarer than you might think. More common, in my small sample size of friends and angel investments, is the email that 40% of the runway remains but the team has decided to pack it in after a year or three of giving it an honest effort.

Once my first company was growing revenue (about three years after founding!), it grew revenue about 10X/year. It turns out that Modelbit, which has had roughly a year of growing revenue, has actually grown faster than that. But Periscope didn’t feel successful at all in that year, and Modelbit similarly does not feel at all successful. Why not? The answer is bracing and clarifying: It’s because we are not yet successful. Nor were we that year at Periscope. At a job, we’d have a boss saying “good job” and “you hit the target we set for you” to make us feel good about our meager progress. As a founder, there is only the unavoidable truth: that nearly all the things we need to prove to realize our goals are still unproven. 

How do we get there? There is only one way I know of: By inches. By grinding, or if you prefer more violent analogies, with lead bullets. Another sales channel experiment next week. Another feature that might unlock an expansion tomorrow. Another product direction that might open up a new market next month. Another message that might get a prospect to open a sales email this weekend. In another year, if we're lucky, we'll look back and see it all compounded again. But of course, that's far from guaranteed.

Maddeningly, I have been unable to predict who will have the grit to grind through the early years. Probably an exception is multi-time founders who know what they’re getting into, but even then, I’ve seen folks decide at some point in their lives that they just want something that’s a little easier day-to-day. I get it.

For me, there are three things that help. First, I try to embrace that lack of external validation. It’s a myth: An illusion that someone else is creating for me. I cultivate pride in the knowledge that consensual illusions are for other people. I don’t need that shit, or so I tell myself staring at the ceiling late at night. Second, I curate a day-to-day routine that brings me joy. A coffee-making ritual in the morning. Taking the long way to work, on the train by the water in summertime. Saturdays writing a little code for the feeling of accomplishment. 

Third, fleetingly, is the understanding that self-worth really does not come from all this anyway. If you think it’ll all feel better when you exit for millions, I have bad news for you. The week I sold my company, a guy in a bar at SFO airport asked me about the rumpled suit I was wearing. I told him, proudly, I’d come from a press hit about selling my company that week, and was now flying directly to see my brother get his Ph.D. (Mom had a good week that week.) The guy said, and I quote: “Huh.” And then turned back to the basketball game. It turns out that the validation from business success is fleeting, but the validation from hugging your family is long-lasting. 

A weird thing about being a second-time founder is first-time founders calling you for answers to unanswerable questions. A common one is the seed-stage company that has been wandering in the desert for a while, making some progress, but without any breakout success. What to do? The only thing you can do: Keep going.