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Karl Jacob pitched his startup LoanSnap to Richard Bransonduring a kiteboarding trip and walked away with the billionaire's backing for its $8 million Series A in 2018.
Jacob was an early advisor to Facebook, and says his experience working in the early days of social networking reinforced his belief in taking bigger risks and bigger failures.
According to Jacob, founders and investors need to be more comfortable with failure and more patient with teams trying to unseat massive entrenched industries.
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Karl Jacob was riding high.
The former Facebook advisor had just started LoanSnap, an AI-powered platform for mortgage lending, and was kiteboarding in the summer of 2018 on Necker Island, one of the sport's premier locations owned by billionaire Richard Branson. Jacob was on the island for an entrepreneurs' retreat, courtesy of an invite passed along by a friend. When Jacob climbed out of the crystal clear waters for lunch, he noticed Branson off by himself.
"It's something I've learned if you see an opportunity like that you take it," Jacob tells Business Insider. "We started talking about our sessions and our tricks and jumps and he eventually asked what I did. When I told him I started a mortgage company, Richard turns to me and with a big smile and says, 'Interesting, I own four of those. We should talk.'"
Read More: Google's AI venture fund is leading a $3.85 million round into a startup that's trying to reinvent the industry for homeowners insurance
According to Jacob, kiteboarding has many parallels with starting a business. There are plenty of risks and anything can go wrong at any moment. People who succeed in both environments share many qualities: they are adventurous, open to risk, and comfortable with failure.
"It's a more natural way for people to meet," says Jacob. "My conversation with Richard started around the sport and ended around business, and our first impressions of each other were about the sport. You know this person is competitive and adventurous and overcame their fear, which is a big part of being a good entrepreneur."
Jacob explains that he is more prone to taking risks now than when he was younger. He emphasized the importance of having investors aligned with longer term goals and bigger risks, and pointed to Pinterest's public offering Thursday as evidence of those risks paying off.
"If you are going after a big space with game changing idea, you better have patient investors that understand you will fail and you will fail a lot before you make it," Jacob says. "Pinterest is one of the best examples of that. It took [Pinterest cofounder and CEO] Ben [Silbermann] seven years to get Pinterest to work. People who have the discipline to fail and try again, they ultimately win."
In the weeks following Jacob's serendipitous kiteboarding trip, he closed LoanSnap's $8 million Series A led by True Ventures. Branson was among the company's backers. SEE ALSO: Founders Fund made its first alcohol investment. Here’s how the 28-year old woman who founded the company is trying to change drinking culture for the better.
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