Missed Unicorn Investments

Shaan shares a story about several major investment opportunities he and his friends missed in their early days in Silicon Valley.

"There were so many opportunities right under my nose that I was blind to. For example, the founders of Calm were in our early mastermind groups. Alex was talking about how hard it was, saying 'it's hard to raise money right now.' We were just like 'dude it's a cool app, you should stick with it.' That's a $2 billion+ company now.

Then there was Alex McCall who started Clear. I remember thinking this guy's amazing - I should invest in Clearbit. I went to his office, loved the energy. At the end he told me he was buying up Stripe shares when Stripe was at $2 billion valuation. Everyone knew Stripe was amazing - the best startup in Silicon Valley. Now I would give anything for Stripe shares at that price - it's like a 100x from there.

Even Loom was in our mastermind. I remember trying to mentor Shai saying 'don't worry, you'll figure it out, maybe it's not this one but when you get to your real game you're gonna be good.' Greg missed it too - it was called OpenTest.co back then.

If I could go back and whisper strategy advice, I would say: invest in all the smart people you know, invest in all the expenses on your P&L, and don't try to be Mark Zuckerberg. The things that sound kind of niche and funny are actually better signals than what VCs are saying is going to be huge."