Ev Williams

How Chris Sacca turned a $25K Twitter bet into billions

Shaan recounts Chris Sacca angel-investing $25K into Ev Williams' startup that became Twitter, then aggressively buying employee shares whenever someone needed cash (e.g. to pay for a wedding), accumulating 10-15% of the company by IPO and becoming a billionaire.

“Anytime there was an opportunity to get shares in Twitter, he took it. Some employee is leaving the company, he's like, hey, I'll buy your shares. Somebody needed to pay for a wedding, he's like, cool, let me buy some of your shares and then you get some money for your wedding. And he over time accumulated this huge position in Twitter, like I think 10-15% of the company by the time it IPO'd, and it made him a billionaire because of how big of a position he had accumulated.”

Clubhouse as a one-month network arbitrage in early Silicon Valley

Shaan describes hopping into early Clubhouse rooms to meet hard-to-reach Silicon Valley people (like Ev Williams) who'd never take a coffee but would shoot the shit at 1 AM — a network arbitrage window that closed once the masses arrived.

“And so I thought there was like this arbitrage, network arbitrage opportunity where you could just like get on Clubhouse early and meet a bunch of cool people. Like, I, you know, we hung out one night with Ev Williams and I talked about, you know, like Twitter early on and shit like that. And like, that was cool. I would have never otherwise had that conversation.”

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