Lori Cheek gave up her career in architecture to solve the problem single people had of wanting to connect with the attractive stranger at the next table or next seat without giving away too much information. She formed Cheek'd and now, instead of building structures, she's helping people build relationships.

What made you decide to start a home business?

After working as a NYC Architect for 15 years, I came up with an idea that lead me into the NYC World of Tech and am now solving missed connections one card at a time.


I completely threw away my design career and I'm no longer building structures, I'm now building relationships.

Why did you start the business you did?

Nearly five years ago, I was out to dinner with a friend and architectural colleague, and I had excused myself from the table. When I returned, my handsome friend 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 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.

What steps did you take to get started?

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.). They helped me get my idea off the ground and into market and now I'm successfully building and branding Cheek'd from my Studio apartment on NYC's Lower East Side completely solo.

How did you get your first customer/client?

After launching my website in May of 2010, I had to figure out how to tell the world about Cheek'd. It wasn't just going to go international on it's own. I had to get creative about how to market my business on a shoestring budget. I decided to target 20 of the major editors in New York by messengering a sole Cheek'd card that read, "This card could change your life." in a mysteriously packaged black envelope. A few weeks later we were coined by the New York Times as “the next generation of online dating.” A few days after that, I found 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 312.633.**** Thank you and I look forward to hearing from you soon.”

We never made it on to the Oprah show, but I knew I was onto something big. Three years later, I've got customers in 47 states in America and 28 countries internationally.

How do you market your home business?

My best marketing strategy has been to not just think outside the box, but to completely get rid of the box! Be creative. Think guerrilla. 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 Guerrilla Marketing guru Jay Conrad Levinson.” I spend a lot of my time guerrilla 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. Here's another opportunity I took to Cheek Rapper, Flo Rida, on Stage at a Samsung Smart TV Launch Party sponsored by Klout earlier this year.

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.

What are your biggest challenges?

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.

What are your biggest successes?

After decades on my own relentless pursuit for love, one day last summer, I was sitting solo at a Crab Shack in Montauk and with no AT&T signal, I decided to toss my best friend, “iPhone,” into my beach bag and when I looked up, a mysterious, gorgeous man in Ray Bans and a baseball cap sitting right next to me said, “Nice tattoos.” I handed him the Cheek’d card that reads, “Let’s meet for a drink.” We met for that drink and we’re engaged to get married this year!

What do you know now that you wish you knew when you started?

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.