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“Physical fitness has been a savior for my mental health while enduring these continuous debilitating legal attacks over the past several years. The only thing I had left to fight for was my mind and health,” says Lori Cheek of Cheekd.

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Taylorsville, Kentucky, native Lori Cheek was featured in Today’s Woman’s February 2011 issue, sharing about her newly created dating website Cheekd, which also provided subscribers with eye-catching calling cards to hand to captivating strangers they encountered in everyday (or night) life. Each card had a different ‘cheeky’ phrase, i.e., ‘I’m totally cooler than your date,’ ‘I’m hitting on you,’ and Cheek’s personal favorite: ‘I just put all my drinks on your tab.’

Almost 10 years later, Cheek, after 25 years in New York, has relocated to the Nulu neighborhood of Louisville — her move mostly prompted by the social distancing requirements of COVID-19 stopping Cheekd in its tracks.

Every time I’ve seen a photo of her anywhere in the 10 years since we last spoke, it seems that no matter what professional knocks life has thrown at her since 2010 (i.e., repeated patented lawsuits by the same person), to me this is a woman whose gaze exudes ‘I NEVER give up…no matter what.’ Cheek’s unsuccessful 2014 appearance on ABC’s Shark Tank is a perfect example of something that would have psychologically crushed many potential business entrepreneurs, but not her.

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“I’ve got a laser-focused vision to succeed, and will do almost anything to keep my business flourishing,” Cheek says. “As long as I can remember, I’ve been extremely stubborn — an unfortunate characteristic, which has ultimately been my lifeline while bringing my vision to life. When most people would have quit, I only hustled harder. I could be the walking poster child for the age-old statement ‘what doesn’t kill you only makes you stronger.’”

As to her business goals from her new home base, she says, “My plan is to consult/mentor startups in Louisville and to help develop the local startup ecosystem, as I see so much potential and feel as if I have so much to contribute. In the meantime, I’ll be working on a pivot to my existing dating app and have a stellar new app idea based on my own experience being new in town here and trying to network/meet new people in a somewhat unsocial time of purposefully distancing.”

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Cheek has also been lecturing for over nine years. “Sharing my journey and inspiring other aspiring entrepreneurs has become a newfound mission of mine,” she says. “As I’ve personally been trying to revolutionize the world of online dating by introducing real world social interaction back into the mix, I know it takes guts to put yourself out there, whether trying to work up the courage to approach a perfect stranger, or start something from scratch and put it all on the table in broad daylight for everyone to see your struggles, mistakes, and failures. It’s that fear of rejection…the fear of humiliation, that holds most of us back,” she adds, before concluding:

“One of the Great Masters of our time, George Addair, said it best — Everything you’ve ever wanted is on the other side of fear.


“My secret to happiness is starting each day with a thankful heart and as soon as I wake up, I start the coffee maker then I roll out my yoga mat and do 30 pushups, 100 sit-ups and 3 rounds of one minute planks followed by a quick stretch. It takes less than 20 minutes and not only does it get my heart pumping and immediately wake me up, it gives me a calm start to the day! Then I grab my coffee, crack open my laptop and begin the entrepreneurial grind already 200 calories lighter! So first thing in the morning, I’m already feeling healthier, stronger, and motivated to conquer the day with a fresh mind and body.”

P.S. Check out the 2001 Today’s Woman article on Lori Cheek and her business.

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