After Brutal ‘Shark Tank’ Rejection, Tech CEO Reinvents Her Dating Business

'They all told me to go die in a hole and I did the opposite'

Ms. Cheeks. (Photo: Lori Cheeks)
Ms. Cheek. (Photo: Katya Nicholas)

The last time we talked to Lori Cheek, she and her dating app—then called Cheek’d—had just been coldly rejected on national television by Kevin O’Leary, Mark Cuban, Barbara Corcoran, Robert Herjavec and Lori Greiner. Now, almost a full year since her admittedly cringeworthy Shark Tank episode aired, the New York-based CEO has completely reinvented her company, and is ready to share it again with the world.

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“They all told me to go die in a hole,” Ms. Cheek told the Observer, in reference to the Sharks, “and I did the exact opposite.”

Okay—the words “die in a hole” didn’t exactly escape any of the Sharks’ lips, but there’s no denying they had issues with Ms. Cheek’s original product. The way it worked, users could pass flirty ice-breaker cards to cute strangers they spotted in the real world; then, those strangers could log onto Cheek’d and discover the dating profile of the person who’d just handed them a card.

The Sharks had some biting, though arguably fair criticisms—namely, that if you could muster up the courage to pass someone a Cheek’d card, couldn’t you just give them your phone number?

“I don’t think it was constructive how they gave me the feedback,” she said, “but I heard it, and I decided to make a change.”

Ms. Cheek said she was incredibly nervous when she pitched her product to the Sharks. (Photo: ABC)
Ms. Cheek said she was incredibly nervous when she pitched her product to the Sharks. (Photo: ABC)

Though we spoke to her over the phone, we could sense Ms. Cheek bubbling as she talked about the new iteration of her product (now called Cheekd, sans apostrophe), which celebrated its launch, appropriately, on Valentine’s Day. The app is designed as a solution to missed connections for smartphone-addicted singles, who might spend so much time looking down at their screens, “the love of their life could walk right past [them],” Ms. Cheek said. “It prompts people to pay attention to what’s happening in the real world.”

The app sends users alerts when other compatible Cheekd users are within a 30-foot radius of them.

“There’s a hot guy at the end of the bar, and you may not know he’s there,” she continued. “You look down at your phone, [and see] Jack N. is 30 feet from you.”

The app also keeps a list of every potential match you pass during the day. Maybe you’ll discover there’s a cute guy with whom you’ve ridden the subway a bunch of times on the way into work, but who you’ve never noticed was there.


“The next morning, you’ll see each other again, and it’s going to force you to talk to each other,” Ms. Cheek said. “I think it’s going to be a little awkward, but at least you’ve kind of already said hello.”

And here’s the super cool part: because Cheekd uses Bluetooth, it doesn’t require an Internet connection to function. That means it works in places like airplanes and subways, where missed connections tend to occur more frequently.

Most importantly, the new Cheekd leaves behind the flaws the Sharks pointed out in her old app.

“It’s taking the awkwardness out of slipping people that card,” she said. “Sometimes it was hard for me to do, and it was my business.”

Cheekd, re-invented. (Photo: iTunes)
Cheekd, re-invented. (Photo: iTunes)

But bouncing back from rejection—on national TV, no less—wasn’t always easy. After Shark Tank, Ms. Cheek said she felt a general “gloom” over her business. To move forward, she found a new business partner, Roger Chinchilla, who bought out her old partners and is now an equity shareholder. She also found support in special Shark Tank Facebook groups—groups where entry is only granted to people who’ve appeared on the show. Members share feedback, resources and help each other promote their businesses.

The next steps for Ms. Cheek? Building up Cheekd’s user base, and bringing on investors who can provide marketing dollars. She’s currently fantasizing about an ad campaign for New York’s L Train.

Is Ms. Cheek worried, we asked, that investors are going to shy away from her product, having seen how badly it initially fared on Shark Tank? She said she’s “not worried about that for a second.”

“I think investors ultimately invest in people,” Ms. Cheek said. “If they know how hard I worked at this the first time, they’re going to know how hard I’ll work on this the second time.”

After Brutal ‘Shark Tank’ Rejection, Tech CEO Reinvents Her Dating Business