Lori Cheek | Founder, Cheekd

"Hustle until you no longer have to introduce yourself.”

How do you start your day?

With 30 pushups, 100 sit-ups and 3 rounds of one-minute planks while the coffee’s brewing—then it’s time to start the grind.

Who inspires you?

Richard Branson

What’s the best piece of advice you’ve ever received?

Surround yourself with the people you want to become.

What do you need to get you through each day?

Cardio workouts.

What are you reading?

Ask Gary Vee—that’s actually the name of the book.

Recent/ favorite quote:

“Hustle until you no longer have to introduce yourself.”

Briefly describe your business and inspiration for it.

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” thanks to a cross-platform low energy Bluetooth technology, which sends users an immediate notification when someone (within their criteria) comes within a 30-foot radius of them. It’s real-time and works on a subway or a plane without any cellular connection.

How has your passion fueled your business?

I’ve always been extremely social and a huge networker—it’s been my most fruitful tool in building Cheekd. I’m constantly making connections for those around me, and in return, I feel like if I don’t know the person I’m looking for, someone I know will. And now I’m even giving people all over the world a tool to help them find the most incredible connection that exists: love. My idea has become more than just a business over the years—it’s become my mission.

What made you decide to become an entrepreneur?

I’ve always had “the itch,” but it was kind of an accident that it happened so drastically. After working in architecture and design for 15 years, I came up with an idea that lead me into the NYC world of technology. Now I’m no longer building structures—I’m building relationships.

What was the tipping point for realizing you had a good business?

A few months after our launch, we popped up on the cover of the Styles Section of The New York Times: “Move over, Match.com, this is the next generation of online dating.” A couple of days later, I got a call from Oprah Winfrey’s Studio asking for an interview.  I knew I had gold in my hands. Soon after, Cheekd went global with customers in 47 states in America and 28 countries internationally.

What has been the key to your success?

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 poster child for the statement “what doesn’t kill you can only make you stronger.” No matter what, in the end I’ll have a magical and cheeky story to tell.

What lessons have you learned along the way that you wish you would have known at the beginning of your start-up career?

I wish I would have 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! Six 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. No matter what, this has been the most rewarding journey of my life. 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.

What challenges did you face in the early days of being the Founder of your own business?

As a trained architect, 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 in building my business over the past few years. 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—failing has probably been the greatest lesson of all.

What is the biggest mistake you have made in your business to date and how have you moved past it?

When we got covered in the New York Times nearly five years ago, 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 from over the country. The Cheekd 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.

What would you have done differently?

Having brought the wrong team on board when I first started building my business nearly five years ago. I wish someone had told me the importance of having a technical co-founder on board when I started out. I had a team, but the two gentlemen I brought on had the same exact background. I didn’t need two of the same skill sets. 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.

What is the biggest challenge you have had in your business to date and how did you pull through it?

The financial struggles have definitely been the most challenging aspect of my business. Coming from a career of making nearly $120K a year, living a pretty fabulous life traveling, dining out and shopping like it was my job in one of the most expensive cities in the world, I came up with an idea that I had to bring to life.

In May of 2010, I launched Cheekd.com. After finishing off my savings from my 15-year career in architecture, I had to get extremely creative to continue funding my business, and that is where the financial sacrifices began. I made nearly $75,000 by selling my designer clothes at consignment shops and on eBay, doing focus groups, secret shopping and by selling my electronics and other odds and ends around my apartment on Craigslist that all went straight back into my business. The biggest chunk of cash came from renting out my West Village Studio in NYC on AirBnB, while couch surfing for 14 months, where I nearly got evicted and ultimately lost my lease of 5 years in my gorgeous apartment. I’m in much better shape now, but me initially bootstrapping my startup led to most of the hurdles I faced building Cheekd.

And finally, 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 five 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.” Then 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.

Around 50 of those emails were from interested investors. Since the Shark Tank aired in February of 2014, I found the missing links from years before. We’ve raised five times the amount I’d sought on the show and I’ve gotten a CTO on board who’s helped facilitate and finance the new face and technology behind the new Cheekd.

When self-doubt hits, what do you do?

I’m learning to trust the journey even if I don’t quite always understand it. It’s been a magical ride.

What aspects of being a start-up entrepreneur do you like or dislike?

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 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. Despite the occasional overwhelming stress, it’s been loads of fun. I feel like I’m living the American Dream—I’ve given birth to an invention. I’ve gone from 15 years of helping others build their dreams to a life finally dedicated to building my own.

Are there any go-to resources that you have found useful to run your business?

After running a small business for nearly 6 years, I’ve learned to never underestimate the power of networking. My advice is to take every advantage possible to meet new people—efficiently communicating and never dismissing a single soul, because you never know who you’re talking to, who they might know or how they’d be able to contribute.

What has been your best strategy for selling your product or service and what have you learned along the way?

Creative Marketing. One of my favorite stories to date was from Dublin’s Web Summit when over 800 startups were exhibiting (90% of them were men) and I decided to stand out by wearing Angel Wings throughout the conference. When I was checking out of my hotel to head back to NYC, I looked down at Judy Dench on the cover of the Irish Times and there I was right next to her (me on my laptop with my Angel Wings—inside there was another 1/4 page picture mentioning my business). The entire country of Ireland was now aware of Cheekd.

How did your experiences in the corporate world prepare you for entrepreneurship, or not?

Architecture is the art, science and business of building and requires an extreme social awareness and understanding of social change as well as a strict attention to detail and design. These elements of my previous corporate career have been crucial in my attempts to reverse engineer an existing industry by simply adding an element of human interaction to a seemingly saturated online dating market. My design background has also been extremely beneficial in giving me an innovative approach to building my business, designing the brand and marketing the product.

What do you think the most important attribute a female entrepreneur/ business owner can possess? 

Perseverance, tenacity, resilience and a huge dose of self-belief.

What do you do outside the office to help you stay creative/productive?

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. 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 would you say to another woman who asked you if they should take the leap and start their own business?

My advice for others considering taking the leap is if you truly believe in your idea, give up excuses and doubt, surround yourself by a trusted and talented team, bulldoze forward and DON’T. LOOK. BACK.