Life Lessons:
Lori Cheek


*Are you happy at the moment?

Ecstatic! I couldn’t be happier… I’ve surrendered my 15-year career, bulldozed through my savings, yet a moment in time (a light bulb moment), a split second, 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.

*If you could go back and say anything to your 16-year-old self now – what would it be?

Dream big, Little Cheek—Your dreams can come true… Trust me. I know.

*What’s the most important thing you’ve learned this year?

I’m learning to trust the journey even if I don’t quite understand it. 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.

*What do you most want to achieve in the next 12 months?

With a newly launched mobile app in my hands, I’ve got a lot to conquer in the next year. The online & mobile dating market is extremely saturated, but I do believe I’ve got the IRL (in real life) twist to our app that may change the way people start to connect. My mission over the next 12 months is to make Cheekd a household name for singles looking to make meaningful connections in the real world.

*What’s your secret to happiness?

My secret to happiness is starting each day with a thankful heart, surrounding myself with people that make me happy and making sure I spend all day loving what I do.

*What one ritual or practice keeps you grounded?

I hit the gym religiously every day. It’s where I relieve my stress and get my head around the day’s activities. It’s the one place I feel like I don’t have to be connected to the outside world and I leave feeling healthier, stronger and motivated to conquer the day with a fresh mind and body.

*What’s your biggest regret?

As a trained architect, I had no idea what I was getting into building a business. After coming up with the idea, I walked around in circles for over a year trying to figure out how to bring my idea to life. Finally I found two guys to help me (I couldn’t have made a worse choice of a team in my life). They both had the same skill set, are no longer involved in my business and they left owning over 20% equity. If I’d known what I know now… The people you surround yourself with are EVERYTHING. I wish someone had emphasized the importance of having the right team on board when getting started. Four years later and a little shuffling around equity, I found the missing piece to my puzzle- I’ve recently gotten a business savvy CTO on board who’s helped facilitate and finance the new face and technology behind the newly relaunched Cheekd.

*What’s the most important lesson you’ve taught your kid(s)?

No kids!

*What bad habit would you most like to change about yourself?

Worrying has got to be my worst habit. Building a business can be extremely stressful and overwhelming, but I’ve noticed that successful people don’t allow set backs to affect their state of mind because they know that with a little thought and a lot of action, they can turn the circumstances back to their favor.

*Aside from motherhood/fatherhood and marriage what are you most proud of in your life?


*When were you happiest?

I’ve never been happier in my life than now. I feel like I’m living the American Dream—I’ve given birth to an invention. I’m an architect turned entrepreneur and I’m no longer building structures. I’m now building relationships and it’s the most rewarding feeling.

*What ten words best describe you?

Determined, Ambitious, Stubborn, Passionate, Funny, Creative, Energetic, Fit, Stylish and Fabulous!


Lori Cheek — Architect turned Entrepreneur, Founder and CEO of Cheekd— a mobile dating app that makes missed connections obsolete. Lori, a Shark Tank Veteran, was recently listed as “The Digital Dating Disruptor” and “One of the Top 10 CEOs to Watch.” A University of Kentucky Architectural Graduate, Lori is no longer building structures. She’s now building relationships.