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Lori Cheek

by margit


Lori grew up in Taylorsville, Kentucky. She now is a die hard New Yorker and living and breathing the city. She resides on the 'Lori Cheek Side' of town.




In my book, there are a couple of damn good reasons why you should quit your job and move on: First - you found something new that you are insanely passionate about, secondly - you are tired of building someone else’s dream instead of your own and thirdly - you are doing it for love! And if all three apply? Lucky you, because that means you are on a mission and nothing can stop you! How do I know? Well, let me tell you about Lori, founder and CEO of the dating app CHEEKD! whose primary goal it is to take the awkwardness out of the first interaction between two strangers, in order for egos to no longer stand in the way of love.

Lori is a Southern girl, born and raised in a tiny, one stop light town in Kentucky and even as a little girl she was constantly dreaming of the world out there beyond her hometown limits. Always creating, forging and inventing growing up, she was looking for an education that would allow her to apply her creativity to a future career. When she came across the Architecture Program at Kentucky State University, that was one of the top 5 in the nation when she was in high school, it seemed like a no-brainer. An internship during her studies brought her to New York for the first time. She immediately fell for the magic, the diversity and the energy of the city and knew one day soon she would come back. Graduation Day came around and her first move was to pack up a U-haul, her cat and her two best girlfriends and drive to Manhattan, the place that she still calls home.

She spent 15 years at high-end design and architecture firms and when I met her, we were both working for the same company only in different locations. Every time I came to New York for business, I would ask my colleagues: Who is the new girl? Only to find out that it was Lori who had switched things up in the style department again. She is a chameleon, always reinventing herself, bursting with creativity and energy and happiest when she is with people, she can make meaningful connections with. Connections - that is what it truly is all about for her and maybe for almost all of us.

The concept behind CHEEKD! was born on a random night in February of 2008, while she was at a restaurant having dinner with a friend. As they were walking out, she witnessed him slide his business card with a hand written note saying 'Want to have dinner?' to an attractive woman at a nearby table. He left with a pending date and Lori left with an idea … How many times had she spotted an intriguing stranger on a train, in a café, crossing the street, at baggage claim and nothing happened? How many times was she just unsure of what to say, their reaction or that of bystanders? In 99% of all cases they got away and Lori was left thinking about what could have happened. “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.”

Her solution to the problem was to keep the smooth move of the personal approach, but then provide a neutral platform to initiate next steps and engage with each other online. She launched cheekd.com in May 2010 and shortly after the New York Times proclaimed: “Move over, Match.com and coined Cheek’d as “the next generation of online dating.”  

My heart and mind are in this project every waking moment. I feel like I’m living the American Dream—I’ve given birth to an invention. I’ve built a brand and a company and thousands of people are using the service all over the world. It’s the most rewarding feeling.

Building her business has been an incredible learning experience for Lori with all the ups and downs you can imagine. She left a high paid job in a field she was familiar with to enter the, to her completely unknown, entrepreneurial and tech area. She took major risks - both financially and mentally - and at times underestimated the amount of work and dedication it needed to succeed. "Everything takes twice as long as you think and often costs twice as much as you’d imagine." I've followed along her journey and watched her get inventive when she wasn't able to pay herself a salary for 4 years, I watched her grow and fall and get back up again, only to take it all to the next level. There is nothing she's ever been more dedicated to. "My heart and mind are in this project every waking moment. I feel like I’m living the American Dream—I’ve given birth to an invention. I’ve built a brand and a company and thousands of people are using the service all over the world. It’s the most rewarding feeling." 

Today the hopeless romantic is revolutionizing the world of online dating by introducing real world social interaction back into the mix. Using physical cards, you can entice people in a very spontaneous, fun and easy way to get in touch with you online or get notified by the new CHEEKD app, when someone who meets your criteria is within 30 feet of you. If you’re near a potential spark, the app makes sure you know about it, so you'll never miss a connection again. 

Lori knows it takes guts to put yourself out there whether you are trying to bring up the courage to approach a perfect stranger or whether you start something from scratch and put it all on one card, in broad daylight for everyone to see your struggles, your mistakes, your learning curve. It’s the fear of rejection, the fear of humiliation that holds most of us back. Fueled by an incredible self-belief and perseverance, she is showing us that we have nothing to loose by jumping over our own shadow and being true to ourselves. We only win, for all we ever wanted in life is on the other side of fear.



What would you say were the biggest obstacles and challenges you had or have to overcome on your way?

I really had no idea what it took to build a business, but I’ve taken a crash course by building one. I couldn’t even begin to count the number of times I’ve failed over the past few years.  I’ve learned to welcome mistakes and even joke that I’ve learned so much from them that I’m going to keep making more of them on purpose so I keep getting smarter. After coming up with the idea, I walked around in circles for over a year trying to figure out how to build my business and 2 guys came on board to 'help me'. I couldn't have made a worse choice of a team in my life. If I'd known what I know now ... Team is EVERYTHING. I just wish someone had told me the importance of having the right team surrounding me. The technical aspect of my business has been one of the bigger challenges I've faced and it's the one thing I definitely would have approached differently from day one. 

What helped/helps you overcome them?

When most people would have quit, I kept going. I've embraced this business like it's my five-year old daughter. I've made so many sacrifices to keep this business alive and I'm fueled to never give up. Quitting is not an option for me. In the midst of my struggles, last year, I found the missing link from years before. After shuffling around equity, I’ve gotten a CTO on board who’s helped facilitate the new face and technology behind the new Cheekd. We’re on a ramp right now and we’re ready to fly.

What do you consider most important in your life? What makes you happy?

My friends and family … surrounding myself with supportive friends and family during my entrepreneurial journey has trumped everything. It's been an intense struggle and I couldn't have made it this far without these amazing people cheering me on to the finish line. Happiness? I’m happy that I’ve had this opportunity to succeed as an entrepreneur. A light bulb moment in time changed my life forever. I’ve gone from 15 years of helping others build their dreams to a life finally dedicated to building my own.