I’m wrong more than I’m right, but when I’m right, I’m really right


Everyone loves a good underdog story and Airbnb’s is no doubt a standout, where Brian Chesky and team fought and fought to succeed only by virtue of their sheer will and determinism.

It’s no surprise that Brian’s post on 7 Rejections went viral. It’s a collection of investor rejections when they were trying to raise $150,000 for 10% of Airbnb. Today they are valued at $24 billion.

After Brian posted 7 Rejections, Chris Sacca posted a tweetstorm revealing his “anti-portfolio” of all the successful startups he passed on early:

All this just shows you how hard it is to distinguish which startups will succeed or fail when they’re starting out. However, don’t let this narrative fool you. The truth is that an investor doesn’t have to be right all the time to be good.

I’m reminded something I heard Chris Sacca say on a podcast. I tried to Google for it but I couldn’t find the source — but it was something like:

I’m wrong more than I’m right, but when I’m right, I’m really right


Early stage investing may be really hard but if you have the right formula, you can do it in a way where you can be wrong often and still do spectacularly.

Need evidence? Here’s some back of the envelope analysis from Dan Primack a few months ago on Lowercase, Chris Sacca’s firm:

If you update Uber’s fair market value from the $62.05 per share mark in the Lowercase doc to the new $133 per share figure, the fund’s overall return multiple on committed capital climbs to a whopping 216x. Or, in real dollars, nearly $1.3 billion on just under $6 million in call-downs (including approximately $23 million in cash and stock distributions for exited companies).

-Fortune: Exclusive: Is this the best-performing VC fund ever?

Chris Sacca may be wrong a lot, but by some measures, he has the best formula in venture capital.