Pop Quiz, Monday with Lori Cheek, Founder & CEO of Cheekd

The Pop Quiz, Monday is a fun little exam that we love to give to savvy business owners. The examination is not a surprise after all since the interviewee already knew about the questions in advance. However, we can always pretend and have fun with the scenario of a young entrepreneur sitting in class nervously biting on their pencil. They are ready to take a pop quiz on a chapter that they were supposed to read the night before. Instead, they played Metroid all night on their SNES (Oops, this was me in high school). The real purpose of the pop quiz is that this is a fun way to introduce business tips from real-world experiences that you can not learn in a classroom. We want to thank our entrepreneur for being a good sport and volunteering their time to answer a few questions to help our community grow from their knowledge.

I want to introduce you to our guest today who will be taking our Pop Quiz Monday.

Can you please tell everyone your name?
Lori Cheek

Photo credit: Lori Cheek

What is your job role?
Founder/ CEO of Cheekd

Tell us about your company?
Cheekd reimagines online dating with a new app that makes missed connections obsolete. Our dating app gives us the power to light the spark face-to-face first and leave the talking for later. And because Cheekd uses Bluetooth, it doesn’t require an Internet connection to function so connections can be made on the subway, a plane… anywhere— You’ll get a notification if someone who meets your criteria is within 30 feet of you. If you’re near a potential spark, Cheekd makes sure you know about it. It’s like online dating, but it starts in the real world.

What do you love most about your job?
Cheekd 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 & 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. Despite the occasional overwhelming stress, it’s been loads of fun. I feel like I’m living the American Dream—I’ve given birth to an invention. I’ve gone from 16 years of helping others build their dreams to a life finally dedicated to building my own. It’s the most rewarding feeling.

What motivates you to get up every day and go to work?
I’ve got a laser-focused vision to succeed and will do almost anything to keep this business flourishing. I’m 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 has to lead to my current 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.

How do your co-workers inspire you?
Although I work remotely from my co-workers, they are an absolute inspiration to me. They’re always filled with positivity and laughter no matter how difficult a situation may be. They give me fuel to be a better force within our business every day.

How do you have fun at work (team building, pranks, etc..)?
n/a (we all work remotely from each other)

What are some of the challenges of your job?
The financial struggles have been the most challenging aspect of my business. Coming from a career of making nearly $120K a year, living a pretty fabulous life traveling, dining out and shopping like it was my job in one of the most expensive cities in the world, I came up with the idea that I had to bring to life… In May of 2010, I launched Cheekd.com. After finishing off my savings from my 15-year career in architecture, I had to get incredibly creative to continue funding my business, and this is where the financial sacrifices began… 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 NYC on AirBnB, while couch surfing for 14 months, nearly got evicted and ultimately lost my lease of 5 years in my gorgeous apartment.

And finally, after four tumultuous years of building my startup with the wrong partners, lots of bad decisions and some major rookie mistakes, I was determined to find a way to take my business to the next level … and what better way than to apply to ABC’s Shark Tank. In September of 2013, I found myself walking down that scary shark infested hallway into a stare off with 5 of the harshest millionaire investors in the world. I’d never been more nervous in my entire life. When I proclaimed, I was going to change the population with my reverse engineered online dating business, serial entrepreneur and Dallas Mavericks owner, Mark Cuban, rolled his eyes, called me delusional and immediately snapped, “I’m out.” Billionaire investor, Kevin O’Leary, demanded that I quit my “hobby” and shoot my business—my passion– like a rabid dog. In the 48 hours after the broadcast, Cheekd.com received a record-breaking 100K unique visitors, and our inbox filled up with thousands of emails insisting that the “Sharks” were “out of their minds” for not investing. A little under 50 of those emails were from interested investors. Since the Shark Tank aired in February of 2014, I found the missing links from years before. We’ve raised over five times the amount I’d sought on the show, and I’ve gotten a CTO on board who’s helped facilitate and finance the new face and technology behind the new Cheekd.

What are some lessons learned from a past project that you can share with us?

Upon leaping into the entrepreneurial world, I 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 building my business. 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. I’ve taken a crash course in building a business and failing has probably been the greatest lesson of all.

What advice would you give to someone who is starting in your industry?
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.

Thank you for taking our pop quiz today. You get an A+ for effort. You can learn more about our interviewee and their business by visiting them on the web:

iTunes app: https://itunes.apple.com/us/app/cheekd/id807619613?mt=8





Author: Ricky Singh, MBA

Editor of The Startup Growth.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.