“I’m an architect turned entrepreneur and I’m no longer building structures. I’m now building relationships.”

Lori Cheek, Founder and CEO of Cheek’d. Lori focuses her efforts on product, marketing and public relations. Prior to launching Cheek’d, Lori worked in architecture, furniture and design for 15 years for companies such as Christian Dior, Vitra & Karkula. Trained as an architect, Lori began her career with multiple project management roles in New York City focusing on architectural interiors. She holds a BA degree in Architecture from the University of Kentucky.

Cheek’d bridges the gap between online dating and real-world romance by providing members with physical cards that they can use to entice people from the real world to flirt with them in the virtual world.

MO: How did you come up with the concept for Cheek’d?

Lori: Nearly five years ago, I was out to dinner with a friend & architectural colleague and I had excused myself from the table. When I returned, my handsome dinner date had scribbled on the back of his business card, “want to have dinner?” As we were leaving the restaurant, he slid that card to an attractive woman at a nearby table. He left with a pending date. I left with an idea… It had happened to me a thousand times during my NYC commute—spotting that intriguing stranger on a train, in a café, crossing the street, at baggage claim, etc. and nearly 999 of them got away. Handing a business card could have been one answer, but I was entranced by the mysterious gesture of handing it to the object of your affection and removing the personal details included on a typical business card, which is simply too much information to hand to a total stranger. A person’s name on a card, alone, could potentially lead you to their front door.

My solution to the problem would apply a personal approach to online dating by moving the initial encounter offline with a smooth physical introduction. In May of 2010, I launched Cheekd.com—my solution to the 999 missed opportunities I’d personally experienced.

MO: Can you elaborate on the transition process from being an architect to becoming an entrepreneur? What’s been the most challenging aspect? On the flipside, what’s been the most fun or liberating aspect?

Lori: I’d always found it extremely frustrating getting paid to build someone else’s dream and have always had a burning desire to do my own thing. It was a split second in time that inspired me to leave my career and I felt so strongly about the idea, there was literally no turning back. I really didn’t know 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 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 so I keep getting smarter. Ultimately, Cheek’d has been the most powerful thing that’s ever happened to me. I feel like I’m living the American Dream—I’ve given birth to an invention. I’m an architect turned entrepreneur and I’m no longer building structures. I’m now building relationships. I’ve built a brand and a company and thousands of people are using the service all over the world. It’s the most rewarding feeling.

MO: Can you talk about the development process from initially having the idea to taking it to market and any early obstacles you faced?

Lori: After walking in circles for an entire year with this glowing light bulb above my head, I met a couple of startup guys at a Mardi Gras Party who also found my idea “genius.” We sat down that Monday and started building what became Cheek’d. I was thrilled that I had a couple of people to assist me with all of the unknowns out there (incorporation, patent, trademark, legalities, writing a business plan, forecasts, etc. etc.). Unfortunately these two guys I’d decided to bring onto my team had the same skill sets. I didn’t know that years down the road, my biggest struggle, technology, is what that third partner should have represented. It took an entire year to launch Cheek’d and several weeks after, we were featured on the cover of the New York Times Style Section and coined as “the next generation of online dating.” The article crashed our site, but we still managed to get orders all over the world as a result of the article, but soon after we realized that the button that was meant to capture everyone’s credit cards to enroll them into the recurring subscription was turned off… In other words, a potential loss of nearly $12,000. I’m still on a mission to find a talented and trusted CTO to join my team.

MO: What’s one marketing strategy that’s worked well for you?

Lori: My best marketing strategy has been to not just think outside the box but to completely get rid of the box! Be creative. Think Guerilla. My marketing tactics were recently mentioned in a business newspaper from my college town in Kentucky: “Lori Cheek works New York City as if she were the secret love child of Carrie Bradshaw and guerilla marketing guru Jay Conrad Levinson.”

I spend a lot of my time guerilla marketing, sidewalk chalking my URL and slipping Cheek’d Cards into pockets, hoods, bags, etc. My favorite story to date would be the personal Lori Cheek’ng of Hip Hop Mogul, Russell Simmons: http://www.observer.com/2010/style/russell-simmons-gets-cheekd-chanel-soho-opening. Here’s another opportunity I took to Cheek Rapper, Flo Rida, on Stage at a Samsung Smart TV Launch Party sponsored by Klout a couple of months ago: http://youtu.be/SQVtjRUcaE0

And lastly, a couple of other videos on how I worked the Tech Convention at SXSW: http://youtu.be/caB11uFHNi8 (doing the robot) and out on the streets: http://youtu.be/SLZ-rKcmxK0. At this year’s NY Tech Day last month, I built a kissing booth with a “Kiss-starter” Campaign and apparently drew the most attention in the whole lane of online dating. On Valentine’s Day, I dressed like Cupid and stood in Union Square giving away Cheek’d cards– alone (mortifying, yet successful). On Halloween, my team dressed up like life-sized Cheek’d cards, we marched the Village Voice Halloween Parade and handed out Cheek’d cards that said, “boo.” to the bystanders.

I’ve gotten so good at my offline marketing technique, I was asked to teach a course on it earlier this spring: http://www.eventbrite.com/event/4478589582#

MO: Startups typically need to pivot and evolve their business model over time, especially as customers start to use the product or service. Can you provide some advice or lessons learned to entrepreneurs on pivoting while keeping your business moving forward at the same time?

Lori: People have been advising me to consider pivoting Cheek’d for nearly two years now. I’m so stuck to this concept and it’s existing model that I can’t personally get inspired to take their advice, but I do find it crucial to communicate with and listen to your customers as well as to keep abreast of the market and trends in your industry in order to make certain you’re always on the right track.

MO: I had a look at your site and blog and it looks like you’re having a pretty great time. What’s the most challenging aspect of your job?

Lori: My biggest challenge would be continually overcoming doubt. Building Cheek’d has been a very lengthy marathon. After coming up with the idea, I risked everything I had and knew. I spent my entire savings account and left my 15-year career in design & architecture.

There have definitely been many days where I just didn’t know what to do anymore or how to best focus my efforts. With my design background, I really didn’t know anything about building a business. It’s been a major struggle over the past few years and I’ve just had to look myself in the mirror on numerous occasions and convince myself that I can do this. I’ve come this far and there’s going to be no looking back. I’ve given this my all. It may take time, but I’m not going to quit. Failure is not an option.

MO: Now that you’ve gained some impressive traction, how do you plan to keep the momentum going?

Lori: Seeing as I’ve bootstrapped Cheek’d with my own money since day one, I’ve finally come to my senses and have decided to raise some money. With a little boost, I feel I can make the technological upgrades to my site and improve the overall user experience. My main goal with funding is to build a strategic partnership with a brand consistent with the Cheek’d flavor in the travel, nightlife or apparel industries. I’ve applied for Season 5 of ABC’s shark tank and I’ve never been more prepared to swim with sharks.