Episode Details

Geoff Cook has built a small empire of successful meeting and dating apps—beginning long before anyone ever swiped right on Tinder—by following a philosophy of fearlessly trying new things. 

“Ten years from now, what will I have regretted—losing half a million dollars or not having done the thing that I wanted?”

Of course, the fact that he has a half a million dollars to lose in the first place should be some indication that a lot of those risks have paid off. Thanks to a series of auspicious business decisions, starting with a profitable essay and resume editing business he launched as a sophomore at Harvard, Cook is living proof that experimentation lies at the heart of a successful startup career.

While his fellow Harvard-attendee Mark Zuckerberg was busy refining Facebook, Cook launched his own spin on a social media platform. Rather than focusing on adding friends that users already knew in real life, his platform would be geared toward meeting entirely new people. So myYearbook was born.

Today, myYearbook has evolved, changed hands, and expanded to encompass a whole collection of meeting and dating apps, all housed under The Meet Group, where Cook serves as CEO.

“I tend to be a tinkerer,” he says. “I’ll push forward an idea even if it seems strange, just because it’s an itch and just keep moving the ball forward. Sometimes, opportunities fall out of that, and sometimes you just lose a lot of money. But it’s an itch I had to scratch.”

In this instance, Cook’s itch proved to be so much more.

Extracurricular Activities 

Cook started his first business in 1997 when, while still writing college essays of his own, he decided to put his economics classes to work and start a small side hustle editing his classmates’ papers and resumes.

But in astoundingly short order, EssayEdge and ResumeEdge had scaled to millions in revenue, and the Thomson Corporation was knocking at his door with an acquisition offer.

So Cook sold his first business in 2002, and just like that, he had the seed money to begin his first post-grad venture. But it wasn’t until he was in his mid-20s, when the social media era had just begun, that the light bulb flicked on.

“The thought was that there needs to be a place to connect to people you don’t know,” he says. “It seemed both MySpace and Facebook were heavy into connecting to your real life friends.”

Teaming up with his brother and sister, who were both still in high school, he created a social network designed to introduce rather than deepen existing friendships. Using games and his search algorithm, making new connections was simple.

All they needed now were users. Luckily, the Cooks had the perfect in.

At Montgomery High School in Skillman, NJ, where both of the younger co-founders were still in school, myYearbook rolled out in 2005. In the first two weeks, there were hundreds of users. Within nine months, there were over a million.

But the road to a million required some clever maneuvering.

“I think we built a pretty good mousetrap in the beginning, but we had nobody in it,” he says, laughing. “What really helped it take off was…we were able to create this great quiz app that ended up getting millions of users every month.”

Reminiscent of today’s Buzzfeed quizzes, users would take a quiz to determine what Seinfeld character they were most similar to. They would then share their results on their MySpace profile, and when a friend—intrigued to learn whether they were an Elaine or a Kramer—clicked on the link, it whisked them away to myYearbook where they were invited to register.

“Quizzes are a very high-uniques business,” Cook says. “You get a lot of uniques, but you get very few page views per unique, because you only basically need to see the quiz and