Meet Lori Cheek – architect turned entrepreneur, founder, and CEO of Cheekd— a mobile dating app that makes missed connections obsolete. Lori is a Shark Tank veteran and was recently listed as “one of the trailblazing entrepreneurs to watch in 2021.” A University of Kentucky architectural graduate, Lori is no longer building structures– she’s now building relationships.
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Table of Contents
Thank you for joining us today. Please introduce yourself to our readers. They want to know you, some of the background story to bring some context to your interview.
Lori Cheek: 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 6 pm. 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.
In February of 2008, I was out to dinner with an architectural colleague in NYC. 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 and in May of 2010, I launched Cheekd.com– a dating service that the New York Times coined as “the next generation of online dating.”
You are a successful entrepreneur, so we’d like your view point, do you believe entrepreneurs are born or made? Explain.
Lori Cheek: Definitely born… My parents were both in the school system— my dad a principal and my mother a high school counselor. On the side, they had many entrepreneurial ventures that ranged from owning properties, farms, dairy cows, an antique business, a farm machinery business and so many more things. I saw as a young child how rewarding it was for them to own their own businesses and how ultimately fruitful and rewarding it was for them. My first job was actually working at one of their gas stations. As young as I can remember, my parents enrolled me in everything that my small town in rural Kentucky had to offer— dance lessons, piano lessons, swimming lessons, gymnastics, 4H and Girl Scouts- I was always the top cookie salesperson in my troop. When I got into Junior High, I started track, cross country, tennis, cheerleading and joined every club I could possible join including the Future Business Leaders of America (little did I know I’d become one one day).
As a very creative and ambitious kid, I started making jewelry and hair accessories when I was 15 years old. Once I’d nailed my craft, I sold my creations to friends and family and by the time I was 17, I’d made enough that I could have opened my own store but needed to start my official college education studying architecture. One of my friends back in the day had nicknamed me “Roxy,” so I named my new venture “Designs by Roxy.” I created the coolest packaging and went door to door in some of the big cities in Kentucky to consign them to their stores. It wasn’t enough to make a living but it definitely helped pay some of the bills through school and fueled my desire to ultimately become the entrepreneur I am to this day.
If you were asked to describe yourself as an entrepreneur in a few words, what would you say?
Lori Cheek: I’ve gone from 15 years of helping build someone else’s dream to a life dedicated to building my own– Entrepreneurship to me is to be able to spend your life in your own way. I no longer have a job, I have a lifestyle and am miraculously always working but I’ve never been happier because I love what I do.
Tell us about what your company does and how did it change over the years?
Lori Cheek: Cheekd initially launched as 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 backward. We’ve since pivoted Cheekd into a hyper-speed dating app that gives singles the ability to never miss a real-life potential “love connection.” After setting up your profile and desired filters, Cheekd will then send you notifications when a potential match is nearby.
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 which starts in the real world.
Thank you for all that. Now for the main focus of this interview. With close to 11.000 new businesses registered daily in the US, what must an entrepreneur assume when starting a business?
Lori Cheek: DON’T EXPECT SUCCESS TO HAPPEN OVERNIGHT:
I wish I’d known that building a business doesn’t make for an overnight success. I believed so much in my idea that after our launch, I thought I was going to be a billionaire by the end of the year! 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.
Did you make any wrong assumptions before starting a business that you ended up paying dearly for?
Lori Cheek: Biggest epic mistake I made over the past 12 years? When we got covered in the New York Times soon after our launch in 2010, we got site traffic from all over the world until Cheekd.com crashed (mild nightmare). Once the site came back to life, we got orders all over the country.
The Cheek’d business model is based on a recurring subscription model once users make the initial dating card purchase. It was the biggest day in the history of Cheekd. Soon after, we realized that our web developer based in London had the button ticked “OFF” that captured our users’ credit card information and were unable to enroll them into our recurring subscription. With hundreds of new signups, we lost nearly $30,000 from this simple mistake. I joke now that our London-based web developer is lucky that he didn’t live in America at the time. We immediately hired someone else and got that button fixed.
If you could go back in time to when you first started your business, what advice would you give yourself and why? Explain.
Lori Cheek: EMBRACE YOUR MISTAKES:
Upon taking the leap into the entrepreneurial world, 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 building my business over the past decade. I’ve learned to welcome the mistakes and even joke that I’ve learned so much from them that I’m going to keep making more of them on purpose. I’ve taken a crash course in building a business and failing has probably been the greatest lesson of all.
What is the worst advice you received regarding running a business and what lesson would you like others to learn from your experience?
Lori Cheek: I had a potential advisor 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 led me to so many amazing opportunities and if it didn’t lead to an opportunity, it led to a new friendship.
In your opinion, how has COVID-19 changed what entrepreneurs should assume before starting a business? What hasn’t changed?
Lori Cheek: Although we’ve been hit by the most disruptive and challenging crisis of our lifetimes, some sort of normalcy will eventually prevail and we must approach these trying times as we would any other roadblock. This period should not only be used to evaluate your business and its current state but to imagine the opportunity ahead whether that involves a pivot, a full-throttle re-launch, or simply an intense game plan to bounce back. Most importantly, now is the time to abandon any self-doubt and to surround yourself with positivity as those who endure this treacherous storm, will only come out stronger and the reward will be that much greater in the end.
What is a common myth about entrepreneurship that aspiring entrepreneurs and would-be business owners believe in? What advice would you give them?
Lori Cheek: A very welcomed piece of advice came to me early in my journey from a fellow female entrepreneur that I’d forward on to other aspiring entrepreneurs— “Failure can be the fastest route to the finish line.”My riskiest business move that ultimately lead to getting funded and my company’s pivot/ re-launch taught me that there’s no such thing as bad press!
After four tumultuous years of building my startup with the wrong partners, lots of bad decisions, and some major rookie mistakes, I was determined to find a way to take my business to the next level … and what better way than to apply to ABC’s Shark Tank. In September of 2013, I found myself walking down that scary shark-infested hallway into a stare-off with 5 of the harshest millionaire investors in the world. I’d never been more nervous in my entire life. When I proclaimed I was going to change the population with my reverse-engineered online dating business, serial entrepreneur and Dallas Mavericks owner, Mark Cuban, rolled his eyes, called me delusional, and immediately snapped, “I’m out.” Billionaire investor, Kevin O’Leary, demanded that I quit my “hobby” and shoot my business—my passion– like a rabid dog. After getting shot down by all five Sharks, I looked them in the eye and said, “Trust that you’ll all see me again.”
Although those final bold words of mine ended up on the cutting room floor (adding insult to injury), in the 48 hours after the broadcast, Cheekd.com received a record-breaking 100K unique visitors and our inbox filled up with thousands of emails insisting that the “Sharks” were “out of their minds” for not investing. A little under 50 of those emails were from interested investors. Since the Shark Tank aired in February of this year, I found the missing link from years before. I’ve gotten a CTO on board who’s helped facilitate and finance the new face and technology behind the new Cheekd (we raised 5 times the amount of money I went seeking on the show!). The newly launched dating app allows users to solve missed connections with a new technology that was not available when the patented Cheekd idea was launched in 2010. It was only a matter of time and I’m thankful I didn’t take the Shark’s advice to quit and move on.
While the physical cards worked anywhere in the world and were a perfect way to break the ice, we found a few barriers; the main one being that our users were still quite intimidated to walk up and slip a card to a total stranger. Looking into alternatives of ways we could change the platform, we discovered a way to make these IRL encounters much easier and less intimidating via a mobile solution.
What traits, qualities, and assumptions do you believe are most important to have before starting a business?
Lori Cheek: I think the most important traits an entrepreneur must have are perseverance, tenacity, resilience and a huge dose of self-belief.
I, personally, have 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 led to my current success. I could be the poster child for the statement “what doesn’t kill you can only make you stronger.” No matter what… in the end, I’m going to have a magical story to tell.
How can aspiring leaders prepare themselves for the future challenges of entrepreneurship? Are there any books, websites, or even movies to learn from?
Lori Cheek: NEVER UNDERESTIMATE THE POWER OF NETWORKING:
The most important lesson I’ve learned in networking (which I’d wish I’d known years ago) is to take 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.
When attending networking events, I find that it’s most advantageous to go alone so that you’re forced to talk to new people. I find it wise to do your homework, in advance, and if the attendee list is publicized, go ahead and make note of those you’d like to meet before the event.
Lastly, is to understand everyone is there for a similar reason and for the most part want to make new connections, so don’t be shy; just walk up and introduce yourself– the only thing you have to lose is an opportunity. Making real-life connections (just like my business idea) has been the most helpful tool in helping Cheekd grow. In the world of business and networking, I recommend that you never ever leave home without your most essential “old school” networking tool– your business (or calling) card. Even in the crux of the digital age, business cards are thriving for a reason– it’s still the single fastest way to share who you are, what you do and how how you can be contacted.
When I decided to launch a dating startup, I had no idea what I was getting into. I was an architect that just came up with an idea I felt so strongly about, that I had to make it happen. Infusing myself into the NYC tech scene was the first very helpful and crucial step. Networking has been the most fruitful tool to date.
You have shared quite a bit of your wisdom and our readers thank you for your generosity but would also love to know: If you could choose any job other than being an entrepreneur, what would it be?
Lori Cheek: With my 11 years of startup experience and knowledge, I’d love to mentor other hopeful entrepreneurs while helping develop the local startup ecosystem as I see so much potential here in Kentucky and feel as if I have so much to contribute.
Thank you so much for your time, I believe I speak for all of our readers when I say that this has been incredibly insightful. We do have one more question: If you could add anyone to Mount Rushmore, but not a politician, who would it be; why?
Lori Cheek: 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 think he’d be the perfect addition to this epic memorial.
Jed Morley, VIP Contributor to ValiantCEO and the host of this interview would like to thank Lori Cheek for taking the time to do this interview and share her knowledge and experience with our readers.
If you would like to get in touch with Lori Cheek or her company, you can do it through her – Linkedin Page
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