Josh Buckley

Josh Buckley 10x'd his money buying Stripe secondary stock at $2B

Sam recalls his friend Josh Buckley buying as much Stripe secondary stock as he could when the company was already valued at ~$2B. Sam dismissed it at the time; Stripe later hit ~$20B, making it a near-no-risk 10x. The framing: which $5B company today could become a $500B company?

“And he was like, yeah, I just think Stripe's a great company and there's secondary stock available and I'm just buying it. I'm like, well, what's the valuation? It's already like a $2 billion company. He's like, yeah, but it's like, Stripe's gonna be big. He's like, I think Stripe's gonna be huge, so I'm just buying up secondary.. And now, so Stripe's valued now at like $20 billion.”