The Life Of An Entrepreneur: Interview With “The Digital Dating Disruptor” Lori Cheek

Screenshot from TEDx Talks

Lori Cheek is an NYC based architect turned entrepreneur, Founder, and CEO of Cheekd that removes the “missed” from “missed connections.” After working in architecture, furniture, and design for 15 years, she came up with an idea that lead her into the NYC world of technology and dating. She has been coined “the Digital Dating Disruptor,” listed as one of 12 “Inspirational Women in Tech to Follow and as one of AlleyWatch’s 20 most awesome people to know in the NYC tech scene. She’s also a Shark Tank Vet, a TEDx Speaker and has been featured in Forbes, The NY Times, Wall Street Journal, Huffington Post, The NY Observer, Entrepreneur Mag, Fast Company, Inc Magazine and so much more.

When most people would have quit years ago, she only hustled harder to keep her dream alive! She could be the walking poster child for the age-old phrase, “what doesn’t kill you only makes you stronger.” It wasn’t an easy ride but she’s never been happier in her life. A lightbulb moment 9 years ago changed her life forever, she left her $120K a year (60 hour work week) design job and now she owns a business that Wired Magazine recently questioned, “Is this the future of online dating?” She has gone from 15 years of helping others build their dreams to a life finally dedicated to building her own.

StarCentral Magazine recently caught up with Lori Cheek and here’s what went down:

Could you please tell our readers a brief background about yourself and how you started your business?

I’m Lori Cheek, an NYC based architect turned entrepreneur, Founder, and CEO of Cheekd that removes the “missed” from “missed connections.” After working in architecture, furniture, and design for 15 years, I came up with an idea that led me into the NYC world of technology and dating. I completely threw away my design career and I’m no longer building structures, I’m now building relationships.

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 backward. 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.

Can you describe your journey to success? When did you start? Did you ever imagine you would become this successful?

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 age-old phrase “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.

What are you currently doing to maintain/grow your business?

Social media and international PR coverage have both been our strongest tool for growth other than our epic brutal bloodbath on ABC’s prime time reality show, Shark Tank, over four years ago. It’s one of the most-watched television shows in America and not only did we gain an outrageous number of customers after it aired but our episode re-airs on CNBC all the time. We always get a blast of users downloading our app all over the world after it airs.

What social media platforms do you usually use to increase your brand’s awareness?

We’re on all of them but mainly use Facebook, Twitter, Linkedin, Pinterest, and Instagram.

What is your main tactic when it comes to making more people aware of your brand and engaging your customers? How did your business stand out?

Over the past eight years, our business has been featured in dozens of the most prominent news and technology websites including The New York Times, Washington Post, The Wall Street Journal, Forbes, Tech Crunch, Inc, Fast Company, Wired Magazine, and countless others.” We’ve been very fortunate to have the press on our side. We’ve built a unique way for singles to break the ice. We’re giving our members a new real-life tool to use as an alternative to missed connections taking place every day.

While there are over 102 million single adults above the age of 18 in America alone, a 25-year-old online dating industry is experiencing serious fatigue and has failed to create a viable alternative to the existing online model. People want to make connections in the real world. We are doing our best to give our customers the most organic, unique real-life experience based on initial chemistry and that’s what has consistently made us stand out above the others.

What form of marketing has worked well for your business throughout the years?

I discovered early on that in a very saturated startup space, it’s crucial to make a splash. Creative marketing quickly became my forte. Not only has it paid off in so many amazing ways, but it’s also been loads of fun. I’ve managed to land myself in The New York Times, The Washington Post, TechCrunch, Fast Company, Inc., Shark Tank, Forbes and many many more publications all over the world. One of my favorite stories 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 (I have a dating business). When I was checking out of my hotel, 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). Ireland knew about Cheekd.com.

How did your brand stand out from the rest of the other brands out there that is similar to your niche?

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.

What money mistakes have you made along the way that others can learn from (or something you’d do differently)?

When we got covered in the New York Times nearly eight 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 user’s credit card information and was 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.

What have you learned in the process of becoming wealthy that others can learn from?

My definition of wealth has changed drastically since I started my business in 2010. 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 & mentally) and surrendered my career in architecture & 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 gone from 15 years of helping build someone else’s dream to a life dedicated to building my own– Success 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.

What new business would you love to start?

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.

If you could go back in a time machine to the time when you were just getting started, what would you do differently?

Having brought the wrong team on board when I first started building my business nearly five years ago. If I’d known what I know now… 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.

If you could go back in a time machine to the time when you were first making a name for yourself, what advice would you give yourself?

I wish I’d been able to tell myself 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. 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.

Do you have any favorite business-related or personal development related books that you can recommend to other entrepreneurs?

My favorite brain fuel right now is Smarter Faster Better by Charles Duhigg— an engaging read where the author shares all sorts of fascinating secrets of being productive in both life and business. He explains how in today’s world, managing how you think rather than what you think can transform your life. Not only has the book helped me reassess my daily motivation and goals, but it’s also helped me create some interesting new productivity hacks to allow me to get things accomplished smarter, faster and better.

As an avid guerrilla and creative startup marketer/ tech startup founder, another one of my favorite business books is The Purple Cow by Seth Godin. It’s all about standing out from the masses and transforming your business by being remarkable.

One of my favorite quotes out of this book::: “You must design a product that is remarkable enough to attract the early adopters – but is flexible enough and attractive enough that those adopters will have an easy time spreading the idea.”

What is the best advice you have ever been given?

Surround yourself with the people you want to become.

What advice would you give to a newbie Entrepreneur setting up their first business?

My strongest 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.

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