Q:  What three things would take a VC from ‘maybe’ to ‘yes’?

A true maybe — nothing. As the other answers have noted.

A typical VC meets 100-300 start-ups a year himself, plus all the others he has to meet that other partners bring in.

Funds 1-3.

Gets excited about 2-10.

Gets ALMOST interested in 11-50. The “maybes”.

Maybe really means almost. Which, since you are only going to do 1-3 deals a year in many cases … means No.


But … the thing is, it turns out, a lot of maybes from Bigger VC Firms end up being Yeses. Just — in the next round. The I-Want-to-Invest, But-It-Just-Doesn’t-Fit-My-Model-Today Maybes.

Sometimes, a maybe really is a No, but I Believe In You the CEO, and I’ll Pay More Later When You Prove it More. Often, this is simply — “It’s just too early”. This especially happens with Series A and B VCs that meet founders a stage too early for their sweet spot.

Then, when a VC that invests multi-stage truly believes in the CEO, especially a first-time CEO or a pre-traction second-time CEO, they pass for now. They want to invest, but it just isn’t there enough yet. It stresses the investment box too much.

But they are happy to pay more, for more progress, later. They already believe the CEO is a winner. They just need to see her get it a little further to fit their box.

Net net, you’d be surprised how many Series A and B VCs “passed” on the round before. They pay more later, and in exchange, get more progress. It’s OK for them.

These VCs are often your best candidates for the next round.

The ones that truly believed in you, and have huge funds, but didn’t quite get there … keep them closely in the loop for the next time.

Here’s just one example from the other day.  An investment, 2 years in the making:

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