Cliff Lerner Turned His Business Failures into the Entrepreneurship Playbook

It was 2005, and Cliff Lerner had a revolutionary idea:

What if online dating actually worked?

At the time, modern online dating was in its early stages, and was a pretty awful user experience. If you were lucky, you’d exchange a few emails with someone, set up a date, then discover at the last minute that your date had flaked.

For busy professionals like Cliff, the process was a waste of precious time.

In response, Cliff founded SNAP Interactive, which created one of the first apps on Facebook, AreYouInterested. It had all the hallmark features we see on dating apps today—swiping, connecting via mutual friends, and showing mutual interests.

“I knew immediately that we’d created something special. After 40 days, we had a million users. One year later, we had 10 million users. We eventually reached 100 million users and we were the fastest growing dating app in the world.”

Suddenly, Cliff’s small start-up went from eight employees trading at a nickel a share, to 50 employees and being valued at nearly $200 million.

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