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16 Weird Things We've Learned About Uber's Billionaire Co-Founder Travis Kalanick The frugal billionaire recently inked a deal for a $36.4 million penthouse in New York City.

By Stephen J. Bronner

entrepreneur daily
Michel Porro | Getty Images

No matter what you think of Travis Kalanick, there's no debating the success of the company he built. Users of Uber have hailed more than a billion rides in more than 600 cities across the globe since Kalanick co-founded the San Francisco-based company in 2009. Uber's success has netted Kalanick a fortune that's at least $1.4 billion, after he sold about 29 percent of his shares. The company was most recently valued at $48 billion.

Uber has changed the transportation industry, dragging it into the world of smartphones kicking and screaming.

Related: The Rise and Fall of Uber and Travis Kalanick

Kalanick's time as CEO of Uber was marred by controversy, including an investigation into rampant sexual harassment at the company that ended in his recent resignation. Still, Uber's success is the envy of the startup world.

On March 7, Kalanick announced via Twitter that he has created a venture capital fund, 10100.

Click through the slideshow to read some interesting things we've learned about Kalanick.

David Paul Morris | Getty Images

Early life

Kalanick grew up in Los Angeles and ran track and played football. He got interested in entrepreneurship early on, selling knives door-to-door for cutlery company Cutco.

John Nordell | Getty Images

First business

When he was 18, Kalanick and a partner started an SAT prep business, New Way Academy. Kalanick apparently scored 1580 on his SATs.

Related: Just Who Has the Right Skills to Turn Uber Around?

Chris Ratcliffe | Getty Images

Family background

Kalanick may have taken inspiration for his career from both of his parents. His father, Don, was an engineer, while his mother, Bonnie, who died in a boating accident in May, worked in retail advertising for the Los Angeles Daily News. His brother, Cory, is a firefighter, and he also has two half sisters, one of whom works at beauty company Rodan + Fields.

Geri Lavrov | Getty Images

The dropout

He became interested in computers in his youth and learned to code by the time he was in middle school. He would later attend the University of California, Los Angeles, to study computer engineering, only to drop out in 1998 to pursue entrepreneurship.

File sharing

His first two companies involved file sharing. Scour, a service that allowed users to share media files, was founded in 1998 and filed for bankruptcy in 2000 after facing a $250 billion copyright infringement lawsuit. At one point, the 13 employees of Scour reportedly shared an apartment, which strained the electrical system.


Skirting the IRS

Kalanick's second company, Red Swoosh, opened four months after Scour shuttered in 2000. To save money while operating the company, Kalanick moved back to his parents' house before relocating to Thailand in 2006. The company once withheld income taxes from employee paychecks -- which is illegal -- but Kalanick was able to raise money from investors to pay the tax bill. Red Swoosh was sold to Akamai in 2007 for about $19 million. Kalanick became a millionaire.

Related: Travis Kalanick Stepped Down, But Uber's Problems Won't Be Instantly Solved

Gov. Travis?

Remember when seemingly everyone ran for governor of California? Kalanick almost entered that fray. In 2003, he took a registration form to run and even registered, which positioned him as an independent candidate.

Gilles BASSIGNAC | Gamma-Rapho | Getty Images

Wii Tennis wiz

In his spare time, Kalanick used to passionately play Wii Sports Tennis, and investor Chris Sacca once claimed that Kalanick was ranked the second best player in the world.

The "jam pad"

The house Kalanick bought after selling Red Swoosh became known as the "jam pad," because many young entrepreneurs visited to discuss ideas. Gary Vaynerchuk and Box co-founder Aaron Levie were among those who crashed on Kalanick's couch. The house even had its own Twitter account.

Brash and abrasive

Kalanick is known for his aggressive and abrasive leadership style and brashness when it comes to skirting the law. He once posted a cease-and-desist letter to Instagram and captioned it, "Charming greeting card from a taxi cartel representative."

John Tlumacki | The Boston Globe | Getty Images

The workaholic

Kalanick is also known for being somewhat of a workaholic. On at least one occasion, he was seen working on a spreadsheet on a laptop at a strip club.

Buddy Mays | Getty Images

Hot tub Kalanick

Kalanick apparently has a superhuman ability to stay submerged in hot water for long periods of time. "Travis can spend eight to 10 hours in a hot tub," Chris Sacca once said. "I've never seen a human with that kind of staying power in a hot tub."

Related: 20 Weird Things We've Learned About Elon Musk

David Ryder | Getty Images

The 14 values

The Uber co-founder is a big fan of Amazon. He took inspiration from its 14 leadership principles to create 14 values for the ride-hailing company. Of course, those include the maligned "Always Be Hustlin'," "Meritocracy," "Toe-Stepping" and "Principled Confrontation."

Qilai Shen | Getty Images

Sex rules letter

In a 2013 letter to employees about an upcoming party in Miami, Kalanick laid out rules for employees to have sex with each other. He ended that part of the letter with, "Yes, that means that Travis will be celibate on this trip. #CEOLife #FML."

David Paul Morris | Getty Images

Inappropriate leadership

Kalanick made a lot of bad decisions as CEO, but one of the most egregious happened in 2014, when he accompanied Uber Senior VP of business Emil Michael and several other employees to a Korean escort bar. The incident was later reported to Uber's human resources department.

Kevork Djansezian | Getty Images

The frugal billionaire

Despite his wealth, Kalanick is known for being frugal. A former employee of Kalanick's at Red Swoosh remembers one time when they went out to lunch: Kalanick "forgot his wallet." He's also proudly admitted to flying coach and staying at cheap hotels. For years, he rode an old motorcycle to work, even in pouring rain. Of course, he rides in Ubers, too, as seen in the now infamous video of him yelling at a driver released earlier this year.

Still, it seems, he does make big purchases. The Wall Street Journal reports that Kalanick recently closed a deal on "a glamorous New York City penthouse for about $36.4 million." The 6,655 square-foot apartment has four bedrooms, a private elevator and a rooftop terrace with a private heated pool and outdoor kitchen.

Stephen J. Bronner

Entrepreneur Staff

News Director

Stephen J. Bronner writes mostly about packaged foods. His weekly column is The Digest. He is very much on top of his email.

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