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Unbuttoned with Lori Cheek of Cheekd

Two weeks ago, I asked for introductions to "inspiring women". Admittedly, a pretty broad query, but I wanted broad responses. For The Thread's new Unbuttoned with series, I'm thrilled to introduce you to some pretty incredible women. Inventors, survivors, powerhouses. Our second feature is Lori Cheek #boss of the dating app Cheekd. She's got cajones, and some serious style chops to boot.

Lori has an amazing story, here it is, in her own words:

I’m Lori Cheek, a NYC based architect turned entrepreneur, Founder and CEO of Cheekd-- a mobile dating app that makes missed connections obsolete.  After working in architecture, furniture and design for 15 years, I came up with an idea that lead me into the NYC World of Tech and am now solving missed connections. I completely threw away my design career and I'm no longer building structures, I'm now building relationships.

Seven years ago, I was out to dinner with a friend & architectural colleague and I had excused myself from the table.  When I returned, my handsome friend had scribbled on the back of his business card, “want to have dinner?”  As we were leaving the restaurant, he slid that card to an attractive woman at a nearby table. He left with a pending date.  I left with an idea...  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 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.  In May of 2010, I launched—my solution to the 999 missed opportunities I’d personally experienced.  Shortly after launch, the New York Times proclaimed, “Move over,” and coined Cheek’d as “the next generation of online dating.”

After four tumultuous years of building my startup with the wrong partners, lots of bad decisions and some major rookie mistakes, I was determined to find a way to take my business to the next level … and what better way than to apply to ABC’s Shark Tank. In September of 2013, I found myself walking down that scary shark infested hallway into a stare off with 5 of the harshest millionaire investors in the world. I’d never been more nervous in my entire life. When I proclaimed I was going to change the population with my reverse engineered online dating business, serial entrepreneur and Dallas Mavericks owner, Mark Cuban, rolled his eyes, called me delusional and immediately snapped, “I’m out.” Billionaire investor, Kevin O’Leary, demanded that I quit my “hobby” and shoot my business—my passion– like a rabid dog.  After getting shot down by all five Sharks, I looked them in the eye and said, “Trust that you’ll all see me again.”

Although those final bold words of mine ended up on the cutting room floor (adding insult to injury), in the 48 hours after the broadcast, received a record breaking 100K unique visitors and our inbox filled up with thousands of emails insisting that the “Sharks” were “out of their minds” for not investing. A little under 50 of those emails were from interested investors. Since the Shark Tank aired in February of this year, I found the missing link from years before. I’ve gotten a CTO on board who’s helped facilitate and finance the new face and technology behind the new Cheekd. The newly launched dating app allows users to solve missed connections with a new technology that was not available when the patented Cheekd idea was launched in 2010. It was only a matter of time and I’m thankful I didn’t take the Sharks advice to quit and move on.

Cheekd has been the most powerful thing that’s ever happened to me.  Building this business has been an incredible learning experience. I’ve taken a major risk (both financially & mentally) and surrendered my career in architecture & design, but my heart and mind are in this project every waking moment. I’ve never been more dedicated to anything. Despite the occasional overwhelming stress, it’s been loads of fun.  I feel like I’m living the American Dream—I’ve given birth to an invention.  I’ve gone from 15 years of helping others build their dreams to a life finally dedicated to building my own. It’s the most rewarding feeling.


In a world full of naysayers and critics, I love Lori's story. She sticks to her instincts and won't take "no" for an answer, Mark Cuban be damned.

Unbuttoned with Lori Cheek

Style icon: Victoria Beckham
Favorite heroine: Maria Von Trapp
Dream lunch date: with Richard Branson at Pastis (which sadly closed in 2014)
Favorite cliché: A chain is only as strong as it’s weakest link.
Personal motto: Hustle until you no longer have to introduce yourself.
Idea that changed your life: The lightbulb moment in 2006 that inspired my career change from architecture to a dating business
Always trying to improve: my physique
Most envious of: Sofia Vergara
Most inspired by: Steve Jobs
Fashion item you would ban: Crocs
Favorite piece in your wardrobe: An Emporio Armani Black Fur Hat
Biggest extravagance: My Soho House Membership
Can’t bare to spend on: Insurance
Irrational fear of: Dying
Brains or beauty: Brains
Audrey or Katharine Hepburn: Katharine
Jennifer Lopez or Lawrence: Lawrence
Diamonds or pearls: Diamonds

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  • Thank you @Constance & @Nina. I just loved this interview with Lori. Check back every Monday for more Unbuttoned with…



    lindsay @ vaughan on

  • Love it! What a wonderful stylish woman! Great interview!

    Constance on

  • Very interesting post. I enjoyed reading.

    Nina on