Lori Cheek, Digital Dating Disruptor 

Lori Cheek is the CEO of Cheekd.com — the reverse-engineered dating site called “the next generation of online dating” by The New York Times.

Lori, a veteran competitor of ABC’s Shark Tank, was recently listed on the American Express Open Forum as “The Digital Dating Disruptor” and “One of the Top 10 CEOs to Watch,” and focuses her efforts on product, marketing, branding and public relations for her venture. 

A graduate of the University of Kentucky, where her focus was architecture, Lori is no longer building structures. She’s now building relationships…one card at a time (see Cheek’d.com for more on their innovative method re: first encounters between potential daters).

Lori is one of “Alleywatch’s 20 Awesome People In New York Tech You Need To Know” — but why limit that simply to tech? With her enthusiasm, energy and Southern drawl, Lori is just one of those now-living-in-the-Big-Apple New Yorkers you need to know – especially if you want an invite to her annual Kentucky Derby party.

She is always hustling – partly because she’s an entrepreneur, and partly because she’s curious as to how many singles there are in the world, and why they can’t find each other. A daydreamer who acts on her dreams, Lori would rather take a chance on doing what she loves than failing at what she doesn’t really want to do anyway.  Read on for more about this very modern entrepreneur.

Who are your heroes?
Richard Branson, Keith McNally [an ultra-successful restaurateur in New York City for over 30 years], Steve Jobs, Lucille Ball & Beyoncé.

What is your current challenge?
$$$ !

Your greatest achievement?
Getting through my recent TEDx Talk.  It’s probably the second most nervous I’ve ever been in my life. Having watched hundreds of inspiring TEDx speakers, it was extremely intimidating knowing my talk would soon be amongst them on the TEDx channel for the rest of the world to see.

What is your motto?
“Hustle until you no longer have to introduce yourself.”

Why are you an entrepreneur?
I had a lightbulb moment in 2008 that wouldn’t go away, so I decided to bring my idea to life. My idea has become more than just a business over the years… it’s become my mission.

What problem are you solving?
Missed connections.

What problem would you like solved?
Hate.

Item you wish you had invented?
Electricity!

Biggest regret?
Having brought the wrong team on board when I first started building my business nearly five years ago. If I’d known then 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 exact same 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.

Which talent would you like to have?
If one can consider this a talent, omnipresence would come in very handy in my overbooked life.

Best pat on the back you’ve ever received?
I’d say recently getting listed in The AlleyWatch List of 20 Awesome People in the NY Tech Scene You Need To Know About .  I was listed with nineteen other people I massively admire.

Advice you wish you’d had (or had followed)?
That being an entrepreneur is journey and not a destination…and to look forward to failure, which ultimately teaches you how to succeed.

Your pitch in 140 characters?
“I’ve invented a dating tool for people to break the ice in the real world.”

 Your bio in 6 words?
“New York City’s Digital Dating Disruptor.”

 The Twitter follower you can’t live without?
 My most supportive follower,  @AssistantNikki.

Your nails on a chalkboard moment?
Watching my pitch to the sharks on ABC’s Shark Tank from earlier this year. I’ve never been more nervous in my entire life. My heart was beating in my throat as I walked down that scary hallway into the tank. I could barely mutter my presentation, which I could have done in my sleep in any other situation. The stakes were high and I freaked out.

The J.O.B. you’d actually like?
I own it!

Biggest misconception about being an entrepreneur?
The amount of work, perseverance and dedication it takes to succeed.

 Inc. or Rolling Stone or…..? Which magazine cover?
Inc.  It’s my favorite TrepLife mag!

What are you reading?
My TweetDeck — the quickest way I find out about pretty much anything I care to know about.

What book is your must read?
Who Moved My Cheese? It’s a quick, powerful and motivational read.

What book did you read that would have been put to better use as a doorstop?
I can’t say I have one. I have such limited time that I rarely read a book that hasn’t come highly recommended.

If I wanted to do what you’re doing…what’s your advice?
Give up excuses and doubt; surround yourself with a trusted and talented team; bulldoze forward and DON’T LOOK BACK.

What conference would you like to keynote?  
Fast Company’s Innovation Uncensored—I’d be honored to be amongst the innovative, inspiring roster of visionaries lined up to share their ideas, advice and solutions to an equally interesting audience.

Short cut, long route, road less travelled? What’s your roadmap?
I feel like I’ve taken a six-year journey without a map. Even as a trained architect, I had no idea what it took to build a business, but I’ve taken a crash course by building one.

Podium you’d like to stand on?
I don’t know if this counts, but I want my own talk show!

What makes you LOL?
Currently LOL’ng at everything on Doublie’s new app, which has a gallery of ready-made celeb & pop culture overlays that you can insert seamlessly into your mobile pictures.

What’s the most important startup/entrepreneurship lesson you’ve learned?  
That the most crucial thing you can do is to learn from your mistakes. Embrace them, make them quickly and don’t make them again.

What would be the title of your biography?
“You’ve Been Cheek’d!” 

Your Ferris Bueller moment: if you could goof-off/skip out for a day, what would you do?
I’d crash a swanky NYC hotel first thing in the morning and hit their gym for a workout, after which I’d lounge by the rooftop pool with a BFF, a bottle of champagne, a dozen oysters and a Scrabble board — then let the day organically unwind from there.

One place in time you’d like to visit?
The Roaring 20’s– not only do I love the fashion, I’m obsessed with swing dancing!

Part of the trick to staying focused?
Focusing on staying focused. There are so many distractions happening on my phone and laptop while I’m trying to work that I have to force myself to ignore things I’d often rather be doing. It’s a serious challenge when I refer to my five inboxes – alone — as a game of Space Invaders that isn’t nearly as fun as the real thing.

You take a three-hour ocean tour and get stranded — what three  items do you have with you?  
My iPhone, a bottle of Sancerre [white wine], and my solar charger.

One last thing:  what’s the question I should be asking you? 
Why was quitting your job the best decision you ever made? Answer: because Cheek’d 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 & design, but my heart and mind are in this project every waking moment. I’ve never been more dedicated to anything. I feel like I’m living the American Dream — I’ve given birth to an invention. 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.

Photo: American Broadcasting Company