Missed Stripe Shares

A story about a missed investment opportunity in Stripe shares when they were valued at $2B.

"Alex McCaw came over one day and we were catching up. He went on to start Clear. I remember thinking this guy's amazing - I should invest in Clearbit. I went over to his office, we hung out. I loved the energy of the office. I was like even if I just felt this office energy, I knew they're building a winner in here.

At the end, I started asking more questions like 'what else are you doing?' He told me he was buying up Stripe shares that were available at a $2B valuation. Everybody knew Stripe was amazing - it was the best startup in Silicon Valley. I had this opportunity to buy Stripe shares at $2B, but I thought I was too late. I thought 'man, I wish I could've got in earlier.'

Now, the things I would give for Stripe shares at $2B... it's already like a 100x from there. That was proven right."