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Wences on top of hill during the day with gray hoodie and tan jacket looking past camera for a portrait
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The Doer

Source: Jonathan Sprague/Redux

FROM PATAGONIA TO SILICON VALLEY

Wences Casares: The Reluctant Serial Entrepreneur

Why you should care

He’s sailed the world, hosted international business dinners in his Chilean castle, and sold companies for more than a combined $1 billion – but Wences Casares says don’t be blinded by the glamor.

In the land of Silicon Valley where people thrive on thinking of fancy and glamorous ways to describe their jobs, Wences Casares is a fan of stripping away the shine.

”I often feel that being an entrepreneur is a fancy way of saying you are a doer,” says Casares in a phone interview. “Entrepreneurs are really good at getting things done.”

To say the 39-year-old Argentine has “done” a lot would be an understatement. He’s sold multiple companies for a combined total of more than $1 billion. His first company became Argentina’s first internet service provider. His second company, Patagon, was an online brokerage firm acquired by Banco Santander, a Spanish bank, for $750 million. He also created Wanako Game, sold in 2007, and Lemon Bank, sold in 2009. Last month he sold Lemon Wallet , a digital wallet platform, for $42.6 million to Lifelock, an identity theft protection company, and joined the company to run their mobile business.

I get nervous when young first-time entrepreneurs say ’I want to be a serial entrepreneur.’ I feel like that’s saying, ‘I want to get married many times.’

“I am not proud of being a serial entrepreneur,” says Casares in his Argentine accent. ”I’d much rather be a one-time entrepreneur. The people I admire are not serial entrepreneurs.” He lists Bill Gates and Michael Dell as examples of role models. Casares might think his multiple businesses signify a kind of failure, but others would differ. Big-time investor George Soros told a TechCrunch reporter that Casares is one of the best entrepreneurs he’s ever backed. He keeps a low profile in the Valley, but Casares is well known and widely admired in Latin American business circles.

Right profile of George Soros with small headset attached to his head

George Soros, investor and Casares supporter

Source: Corbis

“I get nervous when young first-time entrepreneurs say ’I want to be a serial entrepreneur.’ I feel like that’s saying, ‘I want to get married many times.’ Don’t get married if you want to get married many times,” he says, adding, ”Every time you sell a company it hurts a little.”

Another painful aspect of entrepreneurship? Getting kicked out of your own company. Casares says his first company, Argentina’s first internet service provider, did “incredibly well but was basically stolen away” when he naïvely signed papers he shouldn’t have signed. He came to work one day and the security guard told him he’d been fired. “I thought I was on hidden camera. I went from having nothing to having the most successful company in Argentina and went back to having nothing.”

It was a harsh lesson, but it led him to start Patagon, which sold for hundreds of millions of dollars. After that sale he sailed around the world with his wife and children for three years, blogging about their adventures.

Family is important to Casares, who credits his parents, who were Patagonia sheep ranchers, with teaching him how to be an effective “doer.” He grew up on the ranch as the eldest of four. The ranch was isolated, which not only made Casares incredibly close with his family, it taught him an important lesson. ”Everything you need to get done, you have to do it yourself. You can not call a plumber, you can not complain to someone to fix a road. If you want the road fixed you have to do it yourself.”

He received a Rotary Club scholarship to visit the United States as an exchange student in high school, and lived in western Pennsylvania. ”The scholarship changed my life. I fell in love with this country. I find people here to be very straightforward, they have an attitude that everything is possible.”

He made his way back to Buenos Aires for college, but ended up dropping out to start an internet service provider. His background and lack of connections made raising capital difficult. Meetings with potential investors were disappointing. “The first question you get is, ’Who is your father? What private school did you go to?’ If you don’t have the right answer, the meeting is over.”

Image on left, Linda speaking in green top towards right of screen, image on right is a Bel Pesce headshot wearing black. Both on black backdrops

Linda Rottenberg and Bel Pesce

”That’s a pity, but it’s changing now.” Casares is attempting to help speed up that change by mentoring youth both in South America and Silicon Valley. He’s referred to as a role model by people in the Valley like Bel Pesce and Endeavor CEO Linda Rottenberg. “He embodies this ‘pay it forward’ spirit that tells our entrepreneurs if they want to make a lasting impact, it’s not enough to create jobs and achieve great exits,” Rottenberg told Fox News . ”It’s important to inspire and mentor the next generation.”

His life may sound ideal: vast money earned, a castle in Chile where he hosts asados (barbecue dinners) for entrepreneurs and repeated business success. But part of Casares’ mentoring is making it clear that being an entrepreneur is often about failure.

“This is not for most people. If you are doing a good job, most days you are going to be worried. There are a few amazing moments, but nobody writes about the entrepreneurs that don’t make it. Nobody writes about the days you spend worrying.”

Twelve years ago he met a man with an impressive job at corporation in Mexico who asked Casares for advice on a business idea. Casares convinced him to quit his corporate job and become an entrepreneur. Six years later, the man came to see Casares. He was unrecognizable – bald, out of shape, downtrodden and aged. “He says, he’s broke, divorced and depressed, and he did what I said. I felt terrible. He wasn’t blaming me, but I felt responsibile in a way.”

Now, Casares has transformed the way he gives advice. He says that if you have an idea and you wouldn’t be able to forgive yourself if you didn’t try it, no matter the consequences, only then should you go forward.

“If the idea of being broke, divorced, depressed gives you pause – then don’t do it. People don’t like when I say that, but that’s honestly how I feel.”

Update: In March 2014, Wences Casares announced he had raised funds for a new bitcoin and vault startup called Xapo. He is the founder and CEO.

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Meet The Author Lorena O'Neil

Lorena covers religion, LGBT rights and feminism. She is also unusually fascinated by Instagram dictators.

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