NYC Architect Turned Entrepreneur, Lori Cheek Reverse Engineers Online Dating

It had happened to me a thousand times during my NYC commute — spotting that intriguing stranger on a train, in a café, crossing the street, at baggage claim, etc. and nearly 999 of them got away.

Handing someone a business card could have been one answer, but I was entranced by the mysterious gesture of handing it to the object of your affection and removing the personal details included on a typical business card, which is simply too much information to hand to a total stranger. A person’s name on a card, alone, could potentially lead you to their front door.

My solution to the problem would apply a personal approach to online dating by moving the initial encounter offline with a smooth physical introduction.

So, in May of 2010, I launched Cheekd.com—my solution to the 999 missed opportunities I’d personally experienced. Shortly after launch, the New York Times proclaimed, “Move over, Match.com” and coined Cheek’d as “the next generation of online dating.”

Best Success Story:

The most memorable story to date would probably be the call from Oprah Winfrey’s studio after they’d read about my business in the NYTimes. They asked for a deck of cards and a photo of me followed by a short phone interview.

I cried for nearly an hour. I called my parents to tell them and they couldn’t even understand what I was trying to say, then my mom couldn’t stop crying which made me start crying all over again. I couldn’t believe my “little” dating card idea had lead to a call from Oprah.

My life has pretty much been turned inside out (in the most amazing way) from that day forward.

Biggest Startup Challenge:

My biggest challenge was overcoming doubt.

Building Cheek’d has been a very lengthy marathon. After coming up with the idea, I risked everything I had and knew. I spent my entire savings account and left my 15-year career in design and architecture.

I’m no longer building structures; I’m building relationships and it’s the most powerful decision I’ve ever made.

#1 Tip for Entrepreneurs:

Live your dream relentlessly.

Connect with Lori on Twitter and Facebook.

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Photo: Javier Oddo