F*CKWITS: How To Tell If An Investor Will Fund Your Startup

Tim Jackson
Lessons From CEOs
Published in
9 min readJul 26, 2019

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Crying newborn baby: metaphor for the undecided VC
Don’t always assume that VCs are rational adults

A checklist for triaging out timewasters, some thoughts for what to do when they fail to qualify, and a useful fundraising aphorism

“I don’t understand what’s going on,” said Gunther. “I’m spending so much time talking to investors, I barely have any time left to run my company. I’m going to meetings, taking phone calls, rushing from one cafe to the next, and responding to dozens and dozens of email inquiries and requests for documents. Yet I don’t feel the fundraising is any further ahead than it was two months ago. They’re all still interested. But all they do is ask for more information. What a load of f*ckwits.”

Gunther is one of the CEOs I coach. He’s very bright, and his business is interesting and growing, though not as fast as he’d like. Once we started digging a little into his investor problem, it became clear that there were several things going wrong. None of the investors felt any sense of urgency, so nobody was in a hurry to move things forward. Gunther himself didn’t have a clear idea of what the process ought to look like. But the most important problem was that much of his time was being spent talking to investors who, frankly, weren’t going to close. And he didn’t have a good way of identifying who those investors were.

Most of his time was spent talking to…

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Tim Jackson
Lessons From CEOs

Startup founder, former Economist and FT journalist, CEO coach, and seed VC at www.walking.vc