I had the pleasure of interviewing Lori Cheek, an architect turned entrepreneur. She’s the 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.

Thank you so much for doing this with us! What is your “backstory”?

After graduating from the University of Kentucky in 1996, I moved to New York City and started as a sales assistant at a furniture company. Over the next 15 years, I climbed corporate ladders in architecture, furniture, and design firms, making my way to a six-figure income. I worked for firms such as Goldman Sachs, Vitra, and Christian Dior.

For an architect, I managed to land some pretty fabulous, high profile positions that flew me all over the world. This allowed me a life of shopping, dining out, and traveling — like it was actually my job — but it never lead to happiness.

My days in the corporate world felt like time was standing still. No matter how many mornings I’d find myself in trouble for being tardy, I would show up at work 15- 20 minutes late and have my bags ready to jet out the door at 5:59pm.

I despised the idea of working 40+ hours a week to start what felt like “living” at 6pm. I wanted to live to work and create a lifestyle instead of a “job,” and that’s exactly what I’d set out to do.

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

Why did you found your company?

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 lead 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.”

What is it about the work you’re doing that’s disruptive?

Our dating app sets itself apart from our competing billion dollar companies because it gives you the option to interact with a match before starting a virtual relationship with the compatible user.

After setting up your profile and desired filters, 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, it doesn’t require an Internet connection to function so connections can be made on the subway, a plane… anywhere — 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.

We all need a little help along the journey — who have been some of your mentors?

Unfortunately, I’ve never had any specific mentors but I’m extremely thankful for the endless support from my friends and family. My entrepreneurial journey has been an intense struggle and I couldn’t have made it this far without these amazing people cheering me on to the finish line.

How are you going to shake things up next?

Aside from my mission in hopes of connecting people in the real world, my other passion is fitness. I, personally, am always looking to make workout buddies and can rarely get my own network to join me.

My new app idea is to connect like-minded people that can connect to work out together. I think it’ll be such an amazing motivation for everyone to stay committed while making friends at the same time.

Can you share 3 of the best words of advice you’ve gotten along your journey?


Eight years into the entrepreneurial hustle, I’ve learned that entrepreneurship is being on a mission where nothing can stop you. It will take twice as long as you’d hoped, cost exceedingly more than you’d ever budgeted and will be more challenging than anything you’ll ever try but if you give it your all and refuse to give up, you can trust it will be the ride of a lifetime.

I could be the poster child for the saying, “what doesn’t kill you only makes you stronger.” No matter what, this has been the most rewarding journey of my life and in the end, I’m going to have a magical story to tell. My advice to other aspiring entrepreneurs is to be brave and follow your instincts. You can’t cheat the grind, but if you give it your all, you can trust that the payoff will be worth it.


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 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). They both had the same skill set, are no longer involved in my business and they owned nearly 20% equity.

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. I needed a CTO.


My father always told me a kid, “it’s not what you know, it’s who you know” and that statement has proven so true after all these years.

One of the most fruitful tools in building my business over the past eight years is in the power of networking and taking every advantage possible to meet new people; Efficiently communicating and never dismissing a single soul — you never know who you’re talking to, who they might know or how they’d be able to contribute.

What’s a book/podcast/talk that’s had a deep impact on your thinking?

Matt Cutts’ TED talk probably had a bigger impact on me than anything. It was all about challenging yourself to do something new in 30 days. I’ve been an avid guerrilla marketer since the launch of my business in May of 2010. My tactics have lead to articles in The New York Times, Forbes, The Irish Times and many more equivalents all over the world.

It’s easy to get lax about my most creative marketing tool to date and Matt’s talk often penetrates my brain in the morning to leave the house with new guerrilla marketing tools on a daily basis.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

I don’t get star struck by many entrepreneurs but Richard Branson is an absolute phenomenon to me. He did what he loved and money followed.

Worth billions of dollars, he started his first magazine at the age of 16 and now his Virgin brand covers everything from telecommunications to space tourism. As I’ve been building my dream for over six years, I feel like there’s so much to learn from other successful entrepreneurs. Richard Branson is one of the greatest tech & business minds of our time and I believe that even at this stage of my business, he’d have some powerful guidance and advice to potentially push us to the next level.

And now that our dating app works in flight (via Bluetooth), I’ve got high hopes of partnering up with Virgin Airlines to help Cheekd users join each other’s Mile High Clubs.

How can our readers follow you on social media?






Originally published at medium.com