Chris Sacca has made his living of making the right investments, but even the best sometimes miss out on good opportunities.
The "Shark Tank" investor and founder of Silicon Valley venture capital firm Lowercase Capital told CNBC that he has what he calls an "anti-portfolio" – companies that he wished he'd invested in but didn't.
First on the list is home-sharing platform Airbnb.
"I told the founders of Airbnb on one of their first pitch days that it would be dangerous, that somebody would be renting a room in somebody else's house and get murdered and the blood would be on their hands and that probably cost me a couple billion dollars," Sacca told CNBC in a TV interview on Thursday.
Airbnb is now nearing a valuation of $30 billion, according to several media reports.
Ephemeral messaging app Snapchat – which is owned by Snap Inc after a recent rebrand – is the second company on Sacca's anti-portfolio. When Snapchat first launched in 2011, it had a stigma about it because of its disappearing photos feature that allowed people to send risqué images.
This was enough to make Sacca pass at the time.
"The Snapchat guys came up to me after a talk once, and I said I'm really flattered but the pics of your junk... really? So I passed. Later I told my business partner ten years younger than I am and he lost his mind. (He said) 'do you realize what Snapchat is?' That probably cost me a billion dollars or two," Sacca told CNBC.
Snapchat is now worth around $10 billion, according to various reports, and is slated to go public next year.