Lori Cheek – Turning disadvantages into business opportunities

Feeling under-appreciated as an employee, a nonexistent work-life balance, financial struggles, getting out of bad relationships – these are the most common triggers that push women to become entrepreneurs. Tell us about your trigger?

In my 16 years of working in the corporate world of architecture and design, I despised the idea of working 40+ hours a week to start what felt like “living” at 6 pm. I wanted to live to work and create a lifestyle instead of a “job,” and that’s exactly what I set out to do. 

During my career, I was constantly coming up with ideas to build my own business, but none of them was powerful enough to ultimately take the leap until one night at dinner with a colleague, I came up with an idea that would take online dating to a new level.

How did you come up with your business idea?

In February of 2008, I was out to dinner with an architectural colleague. He’d spotted an attractive woman at a nearby table and scribbled, “Want to have dinner?” on the back of his business card and slipped it to her as we were leaving the restaurant. He left with a date. I left with an idea. 

After over two years of brainstorming how to remove the “business” out of the business card, I launched Cheekd – a deck of ice-breaking dating cards with a unique code that leads the recipient to the privacy protected online dating profile of the mysterious stranger who slipped them the card where the two could start communicating online. It was like online dating but backwards. 

We’ve since pivoted Cheekd into a hyper-speed mobile dating app that gives users the ability to never miss a real-life potential “love connection.”

Have you had support from someone, even if just encouragement? Who was that and how did it help you?

Back in 2010, we’d hired a web developer off of NYC’s Craigslist to help fix our broken website. Years later before I found myself flying out to LA to film my coveted spot on ABC’s Shark Tank, Roger (my Craigslist developer from so many years before), came to me and said he’d been watching my hustle for several years, hadn’t stopped thinking about my business and wanted to get involved.

He ended up buying out my business partners, became my CTO (a crucial missing link to my business) and helped facilitate and finance the new face and technology behind the pivoted version Cheekd. Roger ultimately became my business partner, my investor, my mentor, my support system and my personal angel in so many ways.

Female entrepreneurs are often underestimated and overlooked. Have you ever felt at a disadvantage?

I always try to turn a disadvantage into an opportunity. While women are making enormous strides in the entrepreneurial world, men continue to dominate. In response, I find that the smaller business network of women is extra supportive of one another.

I’ve tried to embrace the ratio as being a female founder on the scene. It’s easy to stand out at events and I always joke that as a woman in the startup world, you never have to wait in line for the restroom!

Some say it’s hard work, others say it’s talent and resourcefulness that play a crucial role for success in entrepreneurship? Which traits have been instrumental for your success so far? And why?

I’ve got a laser-focused vision to succeed and will do almost anything to keep this business flourishing. I’m actually not surprised by my determination because as long as I can remember, I’ve been extremely stubborn. When most people would have quit, I only hustled harder. 

I think my personal approach, passion and dedication mixed with my relentless conviction that failure is not an option has been the recipe that has lead to my current success. I could be the walking poster child for the age-old phrase “what doesn’t kill you only makes you stronger.” 

No matter what… in the end, I’m going to have a magical story to tell.

What excites you the most about being an entrepreneur?

Entrepreneurship has been the most powerful thing that’s ever happened to me.  Building my business has been an incredible learning experience. I’ve taken a major risk (both financially and mentally) and surrendered my career in architecture and design, but my heart and mind are in this project every waking moment. I’ve never been more dedicated to anything. I’m living the American Dream—I’ve given birth to an invention. I’ve gone from 16 years of helping others build their dreams to a life finally dedicated to building my own. Instead of reading the book, I’m finally writing it.

Share with us some of the worst business advice you’ve ever received?

I had a potential advisor many years ago that kept trying to nail the power of saying “no” into my head to just about everything. I agreed with the sentiment to a point, but saying “yes” is how I’ve gotten this far in my venture. I could write a book about how many things I’ve said “yes” to that’s lead me to so many amazing opportunities and if it didn’t lead to an opportunity, it lead to a new friendship.

You’ve got a high stake investment opportunity. Pitch your business in 150 words.

The Cheekd dating app sets itself apart from other apps because it gives you the option to interact with a match before starting a virtual relationship with the compatible user. After setting up your page and what you’re looking for, Cheekd will then send you notifications when a potential match is nearby. Instead of encouraging users to continue to hide behind a screen, Cheekd pushes you to engage in social settings while paying attention to potential matches in the area. Our new dating app gives us the power to light the spark face-to-face first and leave the talking for later.

And because Cheekd uses Bluetooth, you’ll get a notification if someone who meets your criteria is within 30 feet of you. If you’re near a potential spark, Cheekd makes sure you know about it. It’s like online dating but it starts in the real world.

What’s the best piece of advice you’d give to inspire aspiring entrepreneurs?

My strongest advice for others considering taking the entrepreneurial leap is that if you truly believe in your idea, give up excuses and doubt, surround yourself by an incredible support network, bulldoze forward and don’t look back because you’re about to be on the journey of a lifetime.

What are your goals for the upcoming year?

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Any final words to end this interview?

A New Yorker of 25 years, I recently relocated to my home state of Kentucky and am working on a new app idea inspired by my own struggles trying to network, meet and date new people in a new city during an extremely unsocial time of purposefully distancing. My solution will allow users to have a more organic, yet virtual way, of making connections for anything from business, networking, fitness, friendship, hobbies or anything with anyone all over the world!