Just weeks shy of his 42nd birthday on May 12, Chris Sacca announced that he was retiring from investing in startups. After being fired from his first job, he worked a stint at Google on business development and mergers and acquisitions. Sacca then founded Lowercase Capital in December 2007. The venture capital firm became an early investor in Uber, Twitter, Instagram, Twilio and Kickstarter. Those bets, and others, have granted him a net worth of $1.22 billion.
The brash investor is known as much for his embroidered cowboy shirts as he is for his investing savvy and brashness. He’s appeared as a guest judge numerous times on Shark Tank and will play himself in an upcoming TV movie called Start Up.
For Chris Sacca’s 42nd birthday, here are 10 wise quotes on investing and startups.
On how to become rich
“People get out ahead of themselves in debt with spending on all of their desires. But if you learn to live pretty simply and well, well under your means, you feel incredibly, incredibly rich and that frees you up and gives you the option to start something new, to leave the job you’re not excited about, where there might be a glass ceiling on you. Just don’t spend your money and you’re well on your way to becoming a millionaire.”
On what it takes to start your own business
“You have to ask yourself, you have to be honest. Do you really have what it takes? Are you incredibly unreasonable? Do you have an irrational sense of the inevitability of the success of what you’re building, or are you just here because it’s fashionable?”
On wearing a uniform
“It also reminded me that the number-one risk in business is starting to take yourself too seriously and starting to believe your own BS a little bit too much. These shirts really reset that expectation.”
“A deep appreciation for politics comes from empathy for our fellow human beings and their diverse paths through life.”
On the likelihood of success in investing
“When you get into investing, your default stance should be ‘No,’ because most deals suck. Most deals won’t make money. Most companies will fail.”
On the qualities of his favorite entrepreneurs
“These guys are learning, they’re modeling, they’re constantly researching, they’re gathering data.”
On simplicity vs. complexity
“Simplicity is hard to build, easy to use and hard to charge for. Complexity is easy to build, hard to use and easy to charge for.”
On how to impress him
“The most successful and ambitious people out there know to create value before asking for anything in return. You want to get my attention? Start doing some of my work. … Distinguish yourself through your hustle and your initiative.”
On how to pitch
“The decision-maker on the other end is still a human being with a spouse, kids, who likes music and movies, so start with something that they can literally emotionally attach to.”
“The only way I know to be awesome at startups is to be obsessively focused and pegged to the floor of the deep-end gasping for air. I succeeded at venture capital because, for years, I rarely thought about or spent time on anything else. Anything less than that unmitigated full commitment leaves me feeling frustrated and ineffective.”