Funding

Think of each funding round as part of an ongoing strategy—a multi-stage game, where every decision has ripple effects on the long-term trajectory.

The next year will be challenging for startups. Promising companies will struggle. Many will fail. The only consolation is that the “era of indifferent capital” is coming to a close — may it never return.

Even for strong startups, fundraising is a marathon that requires near constant attention for 8–12 weeks. The process is punishing, and riskier than you might imagine. You need to prep for it as seriously as you would a race.

The “Series A crunch” sometimes still feels real. It dooms many startups that could otherwise have easily survived if they had been more strategic about their seed-stage fundraising.

There’s no good way to tell your board that you’ve blown a quarter, or your superstar head of data science is jumping ship to Google. Still, breaking bad news is a key skill for founders and delivering it well is often what keeps a company alive.

When I used to write for Wired, a cold email was the lowest probability way to get press, but it still worked with some regularity. Cold emailing a VC is a similarly low-percentage play, and many of the best VCs in the world advise against the practice. Still, it does work from time to time.