How One Entrepreneur Turned a Smooth Pickup Move Into a Growing Business

How One Entrepreneur Turned a Smooth Pickup Move Into a Growing Business

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Lori Cheek, founder and CEO of dating app Cheekd, says starting a business and finding romance are very similar, “I think taking a little risk in life in any realm is often something that pays off in the end. I always say there are so many opportunities, and you have nothing to lose except that opportunity.” Cheek’s business is helping people grab those opportunities to connect with each other, “We are a dating app that connects people in the real world. Instead of flipping through strangers and beginning a virtual conversation, this is about making connections with people that are within a 30-foot radius of you,” she said. “The nice thing about it is that it works on Bluetooth, so you can be on an airplane or on the subway and still make these connections without any Wi-Fi or cell signal.”

Cheek recently spoke with us to share what she’s learned through the ups and downs of growing her business.

A Dinner Proposition Turned Business Idea

I was an architect working in design and architecture for 15 years in New York City. I was out to dinner with a guy in 2008 and he slipped a business card to a woman. On the back of his card, he scribbled, “Want to have dinner?” I couldn’t stop thinking about how he ended up going on a date with this girl he handed his business card to. He met her in the real world. He didn’t interrupt her dinner. I had this light bulb that went off in my head about building a dating business that helped people connect in person like that.

Financing Cheekd

I worked at my full-time job as I got the business off the ground. It took a while to build a website and get everything up and running. In fact, it took about 2 years from the day I got the idea to the day our business launched. I tried to keep my job for as long as I could until this became my full-time gig after we launched.

I was very good about saving my money, which I had saved for my future. But, I found something that was way more interesting than my future, which was the “right now” of building my dream. I have not taken out any loans, but I’ve gotten help from my family along the way. I’ve done a lot of side jobs to fund the business after I quit my full-time gig.

There was a point after 4 years of running my business on this bootstrapped shoestring budget that I ran out of funds. That’s when I decided to apply to get on ABC’s “Shark Tank.” As soon as I started talking about the money my company had made, things went downhill quickly and nobody funded me. But, the day after the show aired, my inbox was filled with thousands of emails. Seventy-five of those were from investors. Everybody was telling me this was a great idea and that I shouldn’t quit. I wasn’t going to quit anyway, but it was really nice to hear from so many people who were just cheering me on and telling me to keep going.

I had a partner that had come on a little before I went on “Shark Tank.” After it aired, my partner and I sat down one day and decided to regroup and rebuild our business. At that point, my partner ended up investing five times the money that I had asked for on “Shark Tank,” so that’s where I finally got a chunk of money to build what we have now, which is our app.

I have business credit cards. I ended up getting my first American Express credit card when I launched the business. I was still in good financial terms personally, so I didn’t have any difficulties getting credit for the business. We paid venders and suppliers on terms earlier when our business was focused on cards rather than our app. Now, we do not.

Our app right now is free, so we don’t have any money coming in. We will charge eventually, but we need to get enough users so that it makes sense to start monetizing.

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Business Challenges & Rewards

The most challenging thing about starting a business was having no idea what I was doing at first. I was a trained architect starting out. I pretty much gave myself an MBA by building my own business. I had a huge learning curve. The other most difficult thing has been the financial struggles. There was a point where I ended up renting my apartment out on Airbnb for 14 months while I lived with friends to fund my business. I’ve done a lot of crazy things to keep my business alive. But, it’s my dream and I’ve never been happier.

The most rewarding thing is absolutely leaving my full-time career of helping someone else build their dreams to live a life of building my own dream.

Mistakes & Lessons Learned

The biggest mistake you can make as a business owner is getting the wrong people on board, and I did exactly that. When I had my idea, there were these two guys at a Mardi Gras party who I told my idea to. They were like, “It’s genius! Let’s sit down and we’ll help you bring your business to life!” I was just happy to have two people who were like, “Yay! Let’s go!” They were business guys who had the same skill set. I ended up giving equity to both of them. I didn’t need two of the same skill set. I pretty much threw away 15% equity to somebody who was a clone of the other guy. I had a tech business, so I needed a tech person as that other partner.

The one thing I know I’ve done right is my PR and marketing. You can’t pay for a lot of PR, like getting in The New York Times or Inc. or Fast Company, but I’ve been in everything. A lot of the PR I’ve gotten has actually been around the failure I’ve been through, but about being resilient and bulldozing forward even in the face of the trauma I was dealing with.

If you truly believe in what you do, give up doubt, give up excuses, surround yourself with a trusted and talented team, bulldoze forward and don’t look back.

What’s Next for Cheekd?

My partner and I are actually building the next version of Cheekd, but for business. Imagine you go to a networking event or an expo or a conference and you’ll know who’s in the room. It’s pretty much going to be like LinkedIn, but in the real world. That’s the next step for us. We also are going to build out our Cheekd app on Android.

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About the Author — Ashley Sweren is a freelance marketing writer and editor. She owns her own small business, Firework Writing (http://www.fireworkwritingonline.com/), located in San Jose, California.

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