Sacca's Investment Journey

A story about how Chris Sacca went from law school student to billionaire through aggressive betting and conviction.

"Chris Sacca took his law school money and started day trading in the stock market during the dotcom boom. He took $25,000 and turned it into $10 million, then went in the hole $4 million.

But what really made him successful was how he bet on Ev Williams when he started what became Twitter. When he saw Twitter was a winner, he went all in in a way most people don't. Most people would have let their small check sit and hoped Twitter becomes something. Instead, he quit his job, started showing up at the office every day focused on growth. He personally went fundraising for the company even though he wasn't part of it - he was out there pitching investors to invest in Twitter.

He ended up buying a billion dollars worth of Twitter stock before it went IPO and became their first or second largest shareholder at IPO. He made a billion dollars off his Twitter holdings because he knew when you have a winner, you have to go all in."