P077: Now That I’m a Huge Success, Let’s Look Back at All of My Hard Work

It was a sweltering Sunday afternoon in St. Louis and I was nursing a Bud Light, cooling down after spending the previous hours running an orbital sander over the deck with my dad, when Twitter started to vibrate. There was a faint sense of subtweeting in the air; discussion of Airbnb started to proliferate. Then super-investor Chris Sacca posted a series of tweets about some times that he passed on investing in what would become big businesses. I followed those tweets through to the epicenter of this activity, rolled my eyes publicly (as you do) and then went on with my day. In retrospect, Twitter wasn’t literally vibrating, it was most likely a temporary side effect of that orbital sander.

Monday morning: woke up vaguely irritated by the Airbnb thing. Went back and read it again to make sure that I didn’t misread it the first time. 4000+ recommendations on Medium. 2800+ RTs and 2600+ faves on the tweet with an especially strong showing from the congrats twitter crowd. Is it possible that I’m missing the point? Re-read the piece again to make sure… nope, it’s still the CEO and co-founder of Airbnb calling out investors who passed on his company with a half-hearted Hang in There Cat tacked on at the end. Still irritated, but at least I have something to write the newsletter about.

Tuesday: I’ve reached the rationalizing stage. Everybody loves Airbnb, and deservedly so – it’s a legitimately useful and transformative service, disruptive in all the best ways and the kind of illegal that isn’t super risky but still makes you feel like you’re cool for sticking it to The Man. To build a successful company, much less anything of this scale, is a tremendous achievement and of course we should celebrate hard work and the overcoming of obstacles. Michael Jordan got cut from his high school team (or did he?!?) and carried that chip on his shoulder for 35 years – saving 7 emails isn’t so strange. Besides, who’s going to feel sorry for the venture capitalists that missed out on Airbnb? When you’re company is valued at $24 billion, VCs are pretty much the only target for punching up, right?

And yet…

VCs must send dozens of those emails every day but the only ones we see screenshotted on Medium are the ones that get sent to pre-horn unicorns – a classic case of small sample size. It’s extremely difficult to be a successful venture capitalist but the table stakes are so high that the terms “success” and “failure” have non-traditional meanings in the VC world. Look no further than Bessemer’s legendary “anti-portfolio” for an taste of what this must be like.

The firms that passed on Airbnb had their reasons. If there’s a young entrepreneur out there that derives strength or comfort from Chesky’s post, that’s awesome, but it’s easy to say “nobody ever believed in me” now that everybody believes in you.

Periodically yours,

Bob Sherron