Buckley's Stripe Secondary Win

A story about how Josh Buckley made a successful investment in Stripe by buying secondary stock early.

"I was hanging out with Josh Buckley one day, and he told me he was buying secondary stock of Stripe as much as he could get. I asked him why, since I wasn't doing that. He said he just thought Stripe was a great company and there was secondary stock available.

When I questioned the valuation, which was already $2 billion at the time, he simply said 'Yeah, but Stripe's going to be big. I think Stripe's going to be huge, so I'm just buying up secondary.'

Now Stripe is valued at around $20 billion, so he took essentially a no-risk bet and 10x'd his money on a private company that was already a unicorn. It wasn't doing like 10% a year - that's a 10x appreciation."