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.
Please tell us a little bit about your company – what is Cheekd all about?
Cheekd reimagines online dating with a dating app that removes the “missed” from “missed connections.” 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.
Tell us a little bit about your background and how you started your company?
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.
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 app that gives singles the ability to never miss a real-life potential “love connection.”
What are your plans, how do you plan to grow this company?
My plan is to expand and create a spin off. 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!
What was the biggest problem you encountered building this product? and how did you overcome it?
When we got covered in the New York Times nearly over ten years ago, our site got traffic from all over the world until Cheekd.com crashed. Once the site came back to life, we got orders all over the country. The Cheekd business model was based on a recurring subscription model once users made their initial purchase. 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 got that button fixed. I learned one of the most valuable lessons of my career, which is to test your tech again and again and again and then test it again.
What were the top mistakes you made starting your business and what did you learn from 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 own nearly 20% equity. I quickly learned the importance of having the right people on your team. 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 out of the gate.
How do you separate yourself from your competitors?
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. 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.
What is one thing that you do daily to grow as an entrepreneur?
My secret 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. I also 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 is the one thing you wish you knew before starting your business?
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. Over a decade 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.
What has been your most effective marketing strategy to grow your business?
DIY Marketing- The growth of my startup has been solely dependent on PR and marketing alone. I’d hired a PR firm several months before our initial launch in May of 2010 and paid nearly $10,000. The firm claimed to have reached out to more than 300 bloggers, resulting in a couple of articles of little consequence. But I soon realized I had more passion for my company than any agency could and decided to take on the task of PR on my own.
After I launched my business in May of 2010, I simply mailed a lone black Cheek’d card that read, “this card could change your life.” in a plain black envelope to 20 of the main journalists in New York City. This stunt cost $12.50 and a few weeks later, we were featured on the cover of The New York Times Styles Section and coined as “the next generation of online dating.”That article lead to our site crashing for hours, orders from hundreds of customers all over America, inquiries from all over the world and finally this email from Oprah Winfrey’s Studio:
“Hello, I am a producer at The Oprah Winfrey Show. I am looking to talk to Lori Cheek about Cheekd.com. I can be reached at 312.633.**** Thank you and I look forward to hearing from you soon.”
We never ended up on Oprah, but the interview with their studio could have been the most exciting day of my life! I’ve been doing my own PR for the past 10 years. Ten thousand dollars lighter and many years wiser, I’ve been covered in just about everything from The New York Times to Tech Crunch, Inc., Entrepreneur, WSJ, Fast Company, Inc, Entrepreneur, Elle Magazine, Forbes, Crain’s NY, CNN and even landed myself in a coveted spot on ABC’s Shark Tank.
If you only had $1000 dollars to start a new business, knowing everything you know now, how would you spend it?
I’d put it towards an online course so I could personally learn how to code.
What’s your best piece of advice for aspiring and new entrepreneurs?
While resilience and self-belief are two of the most crucial characteristics of successful entrepreneurs, my strongest advice to other aspiring entrepreneurs is if you truly believe in your vision, give up excuses and doubt, surround yourself with a supportive and positive network, then get ready for the hustle of your life. You can’t cheat the grind, but if you give it your all, the payoff will be worth it every last minute of it. Take the leap!
What is your favorite quote?
My favorite quotes that keeps me fueled every day of my entrepreneurial journey:
“You just can’t beat the person who never gives up.”
– Babe Ruth
How can we get in touch with you?
You can visit my company website Cheekd.com, find me on social media via Facebook, Twitter, Instagram, and LinkedIn.
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