Chris Sacca (his Twitter) was an early investor in Twitter and is the founder of Lowercase Capital. They invest in startups, acquire later stage companies, and advise businesses and funds of all sizes on strategy and execution. This interview is from 2011.
- In the late 1990s, Chris Sacca used his student loan to start a company within the lawsuit industry - not to pay tuition. But he realized the idea was bad, he didn't have the skills needed, and he didn't have any investors. So before he ran out of money, he began day-trading stocks with the remaining money. This was during the buildup of the tech bubble so he made a huge profit from the trading. When the bubble exploded, his wealth decreased from 12 million to -2.8 million. His surroundings had convinced him that he was a stock market genius - so he thought he knew something. When the stock market crashed, he thought he was just unlucky. He was now 25 years old, no network, and had to find a way to make 2.8 million.
- To make back the money, he got a law degree, moved to the Valley where he began working as an attorney. During the night, he tried to find more work as a freelancer - he wrote business plans, helped people to sell, advised startups, so he could get $50 here and $100 there. But his bad luck didn't en here: he was laid off four days before 9/11 - an event that made the economy even worse.
- He had tried to attend networking events, but no-one wanted to give him any jobs. To turn the trend, he decided to create a company with a serious name. When he attended the same networking events, he now got several jobs. One of these jobs would end with a job at Google. After the Google IPO and a few other sold companies, his net worth was back at zero in 2005.
- It was also revealed that Kevin Rose once had financial troubles. He had to borrow money and his car was repossessed.
- If you can't get a job at a company, show the company that you can make them money. For example, Ryan Graves, who is now working at Uber, wanted to get a job at Foursquare - but they didn't want him. So Ryan Graves took matters into his own hands by finding customers to Foursquare on his own and then he visited Foursquare again and told them he had customers he wanted to give to them.
- It may be a good idea to be quiet while you are developing your product - or competitors may come and get you.
- Invest in what you understand. Chris Sacca didn't invest in Zynga because he didn't understand the gaming industry.
- Even though Chris Sacca has been successful, you shouldn't always listen to him. He argued how he had objected ideas, but then it turned out the ideas really worked.
More articles in the same series: Lessons learned from the Foundation interviews