Rejection From All 5 Sharks Did Not Prevent This Entrepreneur From Succeeding

Before Lori Cheek speaks at the 2016 Entrepreneur 360™ Conference, learn more about the Shark Tank veteran.

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By Entrepreneur Events

Lori Cheek

What happens when an entrepreneur gets rejected from all five investors on Shark Tank? She becomes successful, that's what.

Lori Cheek, who is slated to speak at the upcoming Entrepreneur 360™ Conference on November 16 in Long Beach, Calif., is a living testament of taking failure and turning it into motivation for a successful business. The architect-turned-entrepreneur founded Cheekd, an online dating site, in 2010, and then in February 2014 she appeared on Shark Tank. While she was not able to secure a deal from the Sharks, she received a large amount of fan mail—a few of which were from other investors.

Ahead of her presentation at the Entrepreneur 360™ Conference, she opens up about this experience and more.

The following interview was lightly edited for brevity and clarity.

Why do you do what you do?
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 and mentally, and surrendered my career in architecture and 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 15 years of helping others build their dreams to a life finally dedicated to building my own. It's the most rewarding feeling.

What's one thing you wish you'd known before starting your business?
Cheek: I wish I'd known that building a business doesn't make for an overnight success. 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.

What has been the most difficult part of growing your business?
Cheek: The financial struggles have definitely been the most challenging aspect of my business. Coming from a career of making nearly $120,000 a year, living a pretty fabulous life traveling, dining and shopping, I came up with an idea that I had to bring to life: In May of 2010, I launched After finishing off my savings from my 15-year career in architecture, I had to get extremely creative to continue funding my business. I made nearly $75,000 by selling my designer clothes at consignment shops and on eBay, participating in paid focus groups and secret shopping, and selling my electronics and other odds and ends around my apartment on Craigslist–that all went straight into my business. The biggest chunk of cash came from renting out my West Village studio in New York City on Airbnb, while couch surfing for 14 months, nearly getting evicted and ultimately losing my lease of five years.

What's the riskiest move you've taken in your business? Any lessons learned?
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 five 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, Mark Cuban rolled his eyes, called me delusional, and immediately snapped, "I'm out." Kevin O'Leary demanded that I quit my "hobby" and shoot my business, my passion, like a rabid dog.

After getting shot down by all five Sharks, I looked them in the eye and said, "Trust that you'll all see me again." Although those final bold words of mine ended up on the cutting room floor (adding insult to injury), in the 48 hours after the episode aired the following February, received a record breaking 100,000 unique visitors and our inbox filled up with thousands of emails insisting that the Sharks were "out of their minds" for not investing. About 50 of those emails were from interested investors, and finally, I found the missing link from years before (that came with five times the amount of money I'd sought on the show.) I've gotten a CTO on board who has helped facilitate and finance the new face and technology behind the new Cheekd. The newly launched dating app allows users to solve missed connections with new tech that was not available when the patented Cheekd idea was launched in 2010. It was only a matter of time and I'm thankful I didn't take the Sharks advice to quit and move on. Lesson learned: Never ever give up on your dream.

What's the worst business advice you've ever received?
Cheek: I had a potential advisor a while back that kept trying to nail the power of saying "no" into my head to just about everything. I agreed with the sentiment to a point, but saying "yes" is how I've gotten this far in my venture. I could write a book about how many things I've said "yes" to that's led me to so many amazing opportunities. If it didn't lead to an opportunity, it led to a new friendship.

What's the one thing you do every day to remain sharp and focused?
Cheek: My secret is starting each day with a thankful heart, surrounding myself with people that make me happy and making sure I spend all day loving what I do. I also hit the gym religiously every day. It's where I relieve my stress, and it's the one place I feel like I don't have to be connected to the outside world. I leave feeling healthier, stronger and motivated to conquer the day with a fresh mind and body.

Do you have a kooky or funny customer story?
Cheek: My favorite story was probably when I got pulled up on stage by Flo Rida and stayed on stage with him until I managed to get a Cheekd card in his back pocket. I had people stopping me for weeks afterward saying, "you're that Cheekd girl from the Flo Rida concert!"

Be sure to follow Cheek on Instagram and Twitter, and secure your tickets now for the Entrepreneur 360™ Conference in Long Beach, Calif. here. Seating is limited, so pick them up today for the exclusive opportunity to meet and network with hundreds of other business owners and thought leaders.

Interested in applying for the 2017 Entrepreneur 360™ List? Click Here.

Entrepreneur Events

Entrepreneur Staff

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