Subscribe to Entrepreneur for $5

10 Quotes on Good Bets and Making It in Business From Top Tech Investor Chris Sacca

The man who made early bets on Uber, Twitter and Instagram turns 42 on May 12.


Just weeks shy of his 42nd birthday on May 12, announced that he was retiring from investing in startups. After being fired from his first job, he worked a stint at on development and . Sacca then founded Lowercase Capital in December 2007. The firm became an early investor in Uber, , , Twilio and Kickstarter. Those bets, and others, have granted him a net worth of $1.22 billion.

David Paul Morris | Bloomberg | Getty Images

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 and will play himself in an upcoming TV movie called Start Up.

Related: Shark Tank Star Chris Sacca's Missed Opportunity With Snapchat Proves You Should Read Your Email

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."

On politics

"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."

Related: 35 Killer Quotes From the Stars of Shark Tank

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."

On focus

"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."

Entrepreneur Editors' Picks