The world’s greatest investors: Chris Sacca

Chris Sacca was born in May 1975 and studied law at Georgetown University. During this time, Sacca used his student loans to start trading stocks. He turned $10,000 into $12m by making leveraged trades, only to lose it all and end up $4m in debt (which he eventually repaid). After spells in law and at Google, he started his own venture-capital firm, Lowercase Capital, in 2007. He is also well known for appearing on the TV show Shark Tank (similar to Dragons’ Den).

What is his strategy?

To invest in a range of tech firms before they go public, maintain close relationships with the founders and guide them as they grow.

Did this work?

Lowercase doesn’t disclose returns. But documents leaked to the press show that, between 2010 and 2015, Lowercase’s flagship fund returned 447% in cash to investors, and has unrealised stakes in tech firms that it claims take returns to an additional 7,600%. An early stake in Uber may have taken total returns to 216 times the initial investment, which would make Sacca one of the most successful venture capitalists ever. He has a personal fortune of $1.2bn.

What was his biggest success?

Sacca first invested $26,000 in Twitter in 2006, then bought more shares in the following years, using $1bn of outside money to buy from employees just before the company went public in 2013. He sold most of the shares in 2015, when the share price was around double current levels. Overall, he made $5bn for himself and his investors from the company.

What lessons are there for investors?

Value investors often feel uncomfortable increasing their investment in a company that has seen its share price increase. However, there is some empirical evidence that letting your winners run, and selling your losers, can boost returns.