Funding

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.

For some entrepreneurs, raising capital is effortless. When you see a company raise tens of millions of dollars, series after series, especially if they have few other milestones to promote, you know you’re in the presence of a world class presenter. Fundraising is a startup super power, just like consumer product instincts and B2B sales acumen. Some founders are just “natural athletes” who possess a knack for storytelling paired and charisma, typically topped off with some credibility in a prior venture.

We’ve been trained by infomercials that “But wait, there’s more!” is a powerful sales pitch. Not surprisingly, this approach is used frequently by entrepreneurs pitching their startups. Somewhere between slides 12 and 15, the passionate founders take a breath, clear their throats and declare “But the real opportunity in this business is …”

Getting courted by investors is an exciting milestone for any start-up. But when the VCs start calling, don’t let their enthusiasm cloud your judgment.