Get All Access for $5/mo

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.

By Stephen J. Bronner

David Paul Morris | Bloomberg | Getty Images

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.

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."

Stephen J. Bronner

Entrepreneur Staff

Contributors Editor

Stephen J. Bronner is contributors editor at Entrepreneur.com. He occasionally writes about food and fitness.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Science & Technology

No More ChatGPT? Here's Why Small Language Models Are Stealing the AI Spotlight

Entrepreneurs can leverage this growing tech to create innovative, efficient and targeted AI solutions.

Franchise

Earn $680K a Year with This Wedding Industry Franchise

Wed Society stands out as a unique player in the world of home-based franchises, catering specifically to the recession-resistant wedding industry with franchisees generating an average annual revenue of over $680,000.

Marketing

10 Effective Growth Marketing Hacks and Strategies for Your Startup

Working at a startup can feel like building a plane while you're trying to take off. Use these ten marketing tips to effectively grow and sustain your startup.

Productivity

My Employees Taught Me These 5 Lessons on Productivity

Entrepreneurs should focus on understanding and catering to individual work patterns and needs rather than enforcing one-size-fits-all productivity methods.