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Startup Lessons From Lori Cheek, the Digital Dating Disruptor

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An idea for a business can come at the most interesting times.

For Lori Cheek, it was while she was out having dinner with a friend and colleague when the light bulb went off for her, leading her to create a dating service where people actually connect in person first.

That was six years ago.

Known as the "Digital Dating Disruptor," Lori is taking the New York City tech scene by storm with Cheek'd, an online dating platform with a twist.

Lori Cheek is the founder and CEO of Cheekd.com. Lori was recently named on Women 2.0's list of "New York's Top Lady-Led Startups," and as one of the top 10 CEOs to watch by American Express Open Forum.

Lori stops by today to share her lessons learned as a first-time entrepreneur.

JB: How did a dinner out with a friend and colleague lead to a business idea?

LC: 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 of how to remove the "business" out of the business card, I launched Cheekd.com. Sporting pick-up lines such as "Act natural, we can get awkward later" and "I'm hitting on you," Cheek'd, coined by The New York Times as "the next generation of online dating," introduces a personal approach to online dating by moving the initial encounter offline with a smooth physical introduction.

JB: You had an amazing career in architecture, working for such companies as Christian Dior, Vitra and Karkula, when you decided to launch your business. When did you know it was the right thing to do, leaving your career behind and going all in to launch your business?

LC: A couple of days after we were covered in The New York Times, I received this message in my inbox:

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 [phone number redacted]. Thank you and I look forward to hearing from you soon.

We never made it onto the Oprah show, but I definitely knew I was onto something big. After months of feeling like I was cheating on my employer by working on both jobs simultaneously, I decided to take the plunge. I quit helping my boss build his dream and decided to focus on building my own.

JB: What were the first couple of years like? What valuable lessons did you learn?

LC: Upon starting out, 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 over the past several years. I've learned to welcome mistakes and even joke that I've learned so much from them that I'm going to keep making more of them on purpose so I keep getting smarter. If I'd known what I know now.... I just wish someone had told me the importance of having a technical co-founder on board when I began building my business. 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.

JB: You have a fearless tenacity about you. You exude passion for your business. How has this helped you make it through the tough times?

LC: 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. 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 will ultimately lead to my 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 and cheeky story to tell.

JB: You have been a master at bootstrapping your business. What have you learned about finding capital to keep your business going?

LC: I could definitely write the book on bootstrapping. After finishing off my savings from my 15-year career in architecture, 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 N.Y.C. on AirBnB while I couch-surfed for 14 months, nearly got evicted and ultimately lost my lease of five years in my gorgeous apartment. It's a little like having a child, where material possessions and even lifestyle begin to lose their priority. I've learned that anything is possible if you want it badly enough, and that if, in turn, you work hard enough, the money will follow. It took over three years, but the money finally found this extremely determined entrepreneur.

JB: You have been called one the biggest hustlers in the New York City tech scene. From doing interviews to TV to speaking to growing your network through attending events, it seems like you are everywhere. How has this helped you and your business?

LC: I definitely have taken advantage of every resource possible to help spread the word about my business. On a shoestring budget, I quickly learned that I had to get creative about how to build brand recognition. I've gone around the world and back pitching my business and speaking about my mission of changing the world of online dating. Not only does practice make your pitch-perfect; you never know who might hear your story. I take the stage or a spot in front of a camera every chance it's offered, and it seems as if every time I've shared my vision (whether it be in a newspaper, a blog, on TV or at an event), the experience almost always transpires into a new opportunity. One of my favorite quotes is "Hustle until you no longer have to introduce yourself." It's wild: After all the years of running nonstop, almost everywhere I go someone screams out, "Cheek'd!"

JB: Congratulations on making it onto Shark Tank. What was it like to pitch your business to the Sharks? What did you learn from the experience?

LC: By nature I am a very fun, brave, brash and incredibly confident gal, but there was something about the journey down that high-stakes hallway that freaked me right out. After all, my business and my passion were on the line, and I was throwing myself to the Sharks! As I stood there waiting for the gigantic wooden doors to open, my heart was beating in my throat, and I suddenly panicked that my "numbers" were going to make me look like a total idiot for putting as much time and money into this business as I already had.

Truth is, I didn't actually believe I'd walk out of there with a deal. What I did know was that if my episode got selected to air, 8 million people were going to know about Cheek'd and how determined I was to see it succeed no matter what.

Kevin O'Leary demanded that I quit my "hobby" and shoot my business -- my passion -- like a rabid dog. I remember when he started to tell me that story, my head completely went somewhere else. I didn't even hear it and didn't know the story until I actually watched my segment air. When I was standing in front of them and they'd all shut me down, I still knew there was no way I was going to quit.

And as I imagined, the day after my episode aired, my inbox was flooded with thousands of emails insisting that I not give up and that the Sharks were out of their minds. I learned the age-old lesson that there's no such thing as bad press.

JB: What advice would you give women entrepreneurs thinking about starting a business?

LC: My advice for other women in the entrepreneurial world 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.

JB: In May, Cheek'd celebrated four years in business. Congratulations! You have a lot of exciting things coming up. Could you share what's next for Cheek'd?

LC: After four years of Cheek'd and the physical cards, we've decided to take the eco-friendly flirting route and are going totally mobile. We've hired one of the hottest development teams in the U.S. to rebuild our app. In a few months we'll be a brand-new Cheek'd (logo, technology, concept, etc.). It's a very exciting pivot for us that will allow singles all over the world to never miss a potential love connection -- in the real world.