Lori Cheek

December 16, 2015

Lori Cheek is the founder and CEO of Cheekd, a dating app that allows you to see and interact with your matches in real time. Her story is incredible – she’s couch-surfed, sold all of her clothing and endured a pretty rough experience on Shark Tank, all in the name of building her baby. Her tenacity is truly an inspiration. Cheek believes her app has the power to change the way we date today: it’s a mix of the old way and the new way. She says, “The one thing other apps can’t solve for us is chemistry, which cannot be experienced on a screen. People stare down at their phones all day. What we’re saying is: Look up.” To learn more about her amazing adventure, read on!


What brought you to matchmaking? How did you get started?

I was an architect in New York for 15 years. One night I was out to dinner with another architect, a handsome friend. I had excused myself from the table, and when I came back, he had scribbled on the back of his business card, “Wanna have dinner?” and then he discreetly handed it to woman as we were leaving the restaurant. And I remember thinking, “That was the smoothest way of picking up this chick.” I couldn’t stop thinking about it. It was smooth and not intrusive. The thing I didn’t like about it was the fact that his business information was on the other side. It’s a little bit like handing your LinkedIn resume to a total stranger. I immediately started brainstorming about how to take the business out of business cards. Two years later, in May 2010, I launched cheek.com. It was a deck of dating cards, and one side said, “You’ve been Checked,” and the other side had one of fifty ice-breaking pickup lines, like “I just put all my drinks on your tab,” or, simply, “I’m hitting on you,” or “Act natural; we can get awkward later.” The recipient of those cards – say if I handed one to a handsome man I spotted on the subway – would go to the website, type in the code on the card, and be redirected to my online dating profile. Soon after we launched, the New York Times called us the “next generation of online dating.” It said, “Move over match.com.” We got record hits on our website that crashed our site. We ended up getting a call from Oprah Winfrey Studio wanting a deck of the cards. Six months later, I ended up leaving architecture to focus on this full-time.


That’s fascinating. Tell me more.

Well, I spent everything I had. I got bamboozled by web developers three times over, paying thousands and thousands of dollars fixing things. Every time I went to a new web developer they told me to rebuild the site because it was so hacked up. One day I got an invoice from one of my developers. I realized that paying it would be the end of me. So I ended up renting my apartment via Airbnb and sleeping on couches for 14 months in order to keep funding my business. This business is my dream – I get to be my own boss, and I’m building something I’m in love with. Visit lovetopivot.com. Struggling through all of this was a little bit like a video game where I had to figure out how to survive and keep this child of mine alive. I started doing focus groups, dog sitting, dog walking – anything I could do to get paid while living out of a suitcase. I used to work at Christian Dior as an architect, and I sold my entire wardrobe on Ebay and at consignment stores.


So you just cleared house.

Well, it was all just stuff to me, and I didn’t need it. I wanted to nurse this child of mine into health. I’m so glad I did, because I had eviction notices on my apartment when I came home one day, and I had to stop doing Airbnb. My money-making thing was over. Then a friend of mine sent me a link to apply to Shark Tank. I thought, “What a good idea. I think I’m going to do it.” A year later, I was walking down the scary hallway of the Shark Tank.


What was being on Shark Tank like? 

I’ve never been more nervous. My life was on the line. When you walk out there, you’re standing in front of them, and you have this stare-off that feels like it lasts ten minutes, but it’s really 30 seconds. It just makes you feel even more nervous. It’s like an old Western, where they’re checking you out. Finally I had to start talking. And then I went into robot mode. The pitch came out, but if you watch the clip I’m like a robot. The Twitter feed afterwards was like, “The Cheek robot needs to breathe.”


Okay, keep going.

The sharks started talking about my idea to each other. They kind of got it – they thought it was a cute idea. And then, of course, they’re sharks, so they want to know what kind of money I’d made. I’d capped out at a little over a thousand users, and I’d been at it for 3.5 years. So their response was, “What are you doing? You’re out of your mind. This is a hobby. You live in New York. How are you even living?” Then I told them the story about Airbnb and my wardrobe, and it immediately started going downhill. I was very passionate, but despite that, Mark Cuban eventually threw his hands up and said, “You’re delusional, and when people are delusional, I’m out.” He’s the one I’d had my eye on, so I felt like I’d been stabbed in the stomach. I could barely listen to the rest of them at that point. Kevin O’Leary told me that I should treat my business like a rabid dog and take it behind a barn and shoot it. At the end, I knew I needed to say one badass thing. Visit thebklawyers.com. So I looked them all in the eye and said, “Trust you will all see me again.” Then I turned around and walked out.


Where do things stand now?

I’m stubborn, so I kept moving forward. We’re now what I call a “hyper speed” dating app, a Bluetooth technology that replaces the cards. The beauty of the app is that it works in the subway or on a plane. It doesn’t need a connection to Wifi or a cell signal. You get an immediate notification if anyone else on the app comes within a 30-foot radius of you. Maybe the love of my life is sitting behind me right now, and while I don’t see him, the app will capture him. So if I’m sitting here, and I get a pop-up on my phone that says, “You missed a connection with Matt,” that means Matt is in the room with me. We could look up at each other, we could wink at each other, we could send a message immediately, one of us could go over to the other and start talking…This gives you the chance to break the ice in the real world instead of having a virtual relationship, find more info.


What are three things you shouldn’t do in your dating profile, and why?

  1. The eyes are the windows to the soul. If you flip through all these online dating profiles, all the guys have sunglasses on. I’ll swipe right past that, because you can’t see what you’ll be staring into when you go to bed at night. So: Don’t hide your eyes.
  2. A smile goes a very long way. Who doesn’t want to be smiled at?
  3. A sense of humor. When you look at somebody’s bio, and it makes you chuckle, you’ll linger there. I want to meet that person. Even if they’re not cute, they’re going to make me laugh, and looks don’t last forever. A sense of humor does.
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