Meet Sam Yagan, The “Nerd King Of Online Dating”

CNN Money has declared Sam Yagan, co-founder of OkCupid and CEO of Match Inc., the "nerd king of online dating." I can't say it's the most flattering nickname I've ever heard, but I'm pretty sure Sam is too busy taking Scrooge McDuck-style dives into piles of money to care what CNN thinks of him.

Nicknames aside, CNN and Fortune actually seem to think quite highly of Yagan, who was recently included in the '40 Under 40' list and profiled by the magazine.

Yagan's journey to become one of the most famous names in the online dating biz started with almost no dating at all: he was engaged to his high school sweetheart, and his first company was a CliffsNotes-alternative called SparkNotes. Both ventures went well: he is still married to his high school girlfriend, and SparkNotes sold to iTurf, Inc. for $30 million in 1999.

Despite his early success, Yagan was hesitant to call himself an entrepreneur. He sought out desk jobs, but no one would hire him. "It turns out that if you're a 24-year-old whose only line on their resume says CEO, you are totally unemployable," he says.

Yagan's next project was eDonkey, a P2P file-sharing service (like Napster for video) that initially looked promising but was shuttered after pressure from record labels. Then Yagan had a new idea:

"I hated meeting people at bars when I was single, because it's all about the looks and the funny line," he tells Fortune. "I don't have the looks to compete at a bar, and I'm not that funny. So the last thing I want is to be in a situation where that's what I'm competing on. I'd rather be on OkCupid or Match, where I can write a 300-word essay about myself that's really good."

OkCupid was born in 2004, and a year and a half after it was acquired by IAC, Yagan was made CEO of IAC's entire Match Inc. division. Between Match.com and the many other sites included alongside it, like OurTime.com and BlackPeopleMeet.com, Yagan's segment was responsible for $713 million of IAC's 2012 revenue of $2.8 billion.

His approach to the competition is simple, and it's working. "You're going to launch, you're going to get some success, [and] I'm going to buy you for cheap because you don't have another bidder," he explains. "And then my business has grown."

Yagan's success seems unstoppable. He is now very active in the development of Tinder, a dating mobile app also owned by Match that he believes is one of the most exciting things to come out of the company in a long time. But always lurking in the background is his passion for entrepreneurship, and it seems likely that, one day, he'll leave the dating world behind in search of a new challenge to conquer.