Work-At-Home Success Profile: Lori Cheek the Digital Dating Disruptor


Lori Cheek is an Architect turned Entrepreneur, Founder and CEO of Cheekd— a mobile dating app that makes missed connections obsolete.  Lori, a Shark Tank Veteran, was recently listed as “The Digital Dating Disruptor” and “One of the Top 10 CEOs to Watch.” A University of Kentucky Architectural Graduate, Lori is no longer building structures. She’s now building relationships.

1) How did you get started working from home?

After running my startup for over six years, I’ve tried working from just about everywhere in NYC… a handful of co-working spaces, a members only club called The Soho House, coffee shops and even sometimes at a bar! The place I’ve found I have the most focus is at home at my kitchen table. I find a great Spotify channel, put on imaginary blinders and buckle down for hours on end. I save so much time in the day because I never have to a). get ready b). commute and c). leave for coffee or lunch because they’re always at arm’s reach. There’s always reliable wifi and no one is around to distract me.

2) How did you choose the work-at-home career you do?

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 backwards. 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.

3) How did you get started (basic initial steps)?

After walking in circles for an entire year with this glowing light bulb above my head (my idea), I met a couple of startup guys at a Mardi Gras Party who also found my idea “genius.” We sat down that following Monday and started building what became Cheekd. 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.). Within a week, we had a business plan and immediately began sourcing our web developers and designers and were on the path to building my business which just turned 6 a couple of weeks ago.

4) How did you get your first client or customer or job?

Our first customer came from a simple Facebook Posting the day we launched our business. It was one of the most exciting moments of my adult life!

5) How do you market your business?

Creative Marketing. One of my favorite stories to date 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 to head back to NYC, 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

6) What does your usual day look like?

I’m miraculously somehow always working. I start the morning off with emails & coffee. Afterwards, I hit the gym religiously every day for about 90 minutes. I even catch up on social media, reading articles and emails while on the elliptical trainer for an hour. I usually cook a very healthy lunch then straight to the office where I meet my interns. We work for a few hours together then I usually head out to networking and startup pitch events where I continue to spread the word about my business. I’m usually home by 9 and often cook dinner with a glass of wine, catch up on the emails from the end of the day then hit my pillow by 11pm. Although I never stop, I love what I do, so I love every minute of my days.

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

I wish I’d known 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! Six 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.

8) What advice would you give someone who wants to work from home?
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.

Website: Cheekd

Twitter: @loricheeknyc

Facebook: Cheekd

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