Q&A

Tech CEO Loses on ‘Shark Tank’, Is Visited by On-Set Therapist

Lori Cheek's dating service was rejected by the sharks — but she's still determined to make it successful.

Ms. Cheeks and a Cheek'd card (Screengrab: YouTube)

Ms. Cheeks and a Cheek’d card (Screengrab: YouTube)

Ever wonder what it would be like to quit your high paying job to start a company, then watch it get rejected by five rich strangers on Shark Tank

Us, too. So we caught up with Lori Cheek, the entrepreneur whose dating service, Cheek’d, met exactly that fate on the network TV show last Friday.

Ms. Cheeks used to be a highly paid architect. Then she quit her job to start Cheek’d. The company was on the brink of failure last year, so presenting it on a game show seemed like the only option left.

“I’m an architect no longer building structures,” she insisted before her pitch. “I’m now building relationships.”

Love-starved singles can use Cheek’d in one of two ways: the way that costs money, or the free way. Either pay $20 to $25 for a stack of flirty Cheek’d cards you hand out to strangers, plus $9.95 a month for a membership, or download the app for free and pass out virtual ice-breaking cards to nearby strangers.

Ms. Cheeks says she found a fiancé using her own product, but Cheek’d was still rejected by all five sharks.

How did you feel after watching the Shark Tank episode?

I knew what was going to happen because I was there, but I didn’t remember it was that bad. My presentation was awful — that’s not even me. I think I was so psyched out. I’ve never been more scared in my life. I knew what I was walking into with my numbers… [the pitch] was just mortifying.

How did you prepare for the pitch?

The pitch that I did with the sharks, the producers work with you. I wrote the pitch and they fine-tuned it with me – you practice it with them. I had been so cheeky with them when I was practicing, and it just went totally awry. You have this stare-off with [the sharks] for 30 seconds – whatever nerves you had before, that takes it up to another notch.

What do you think went wrong?

[Cheek'd only had] a little over a thousand paying customers. There was no way I was going to get out of that. That was the answer that shot me down — there was no lying. You can’t go on the Shark Tank and lie about your numbers…

…I just don’t think they got it. I wasn’t even really able to get my point across. What I’m doing is solving missed connections — [for example], the train door’s closing, and there’s an opportunity you might never get again. You get this chance to say hello. I think it’s a very romantic real life way to meet, when we’re in this mode of constant technology connection. [The sharks] would never even need anything like this. They probably don’t remember how difficult it was to find someone. 

Was there a moment you knew it was all over?

When I was in there, it felt like five minutes into it, I knew it was going to go down. I really liked Mark [Cuban], and he was the first one that went out. I really had my eye on him. With his personality, I thought he’d be a great partner for me. 

Was there anything that surprised you about the experience?

It just was so intense. I almost felt like I had been drugged, and I climbed Mount Everest building this business, and once I got to the top, someone kicked me off the mountain.

When you leave there’s a therapist that comes and sees you in your trailer. I was in there with my fiancé and my web developer, and we were drinking wine and [the therapist came in and] I was like… “I’m fine.” 

Even though you got shot down on Shark Tank, are people paying more attention to Cheek’d?

My inbox is just flooded with feedback and praise, and people saying the sharks made a mistake. There’s tons of investors in there. I think it was great. Our site crashed for a couple minutes! We got almost 100,000 unique visitors. We’re definitely peaking right now, that’s the good news, too. Our android app went live Friday. I don’t think we’re near 1,000 [downloads] yet, but it’s okay. It still has a few bugs in it. Its not in the Apple store yet, but it should be any day…

… I’m just celebrating the fact that 8 million people watch the show. It’s like the whole city of New York watching the show. Someone sent me a Google analytic that we got more searches this month than OkCupid or JDate, which is huge.

Since the Shark Tank filming you’ve sort of started over — you’ve redesigned the site and launched a new mobile app. If Cheek’d was barely surviving at the time of filming, how is it still alive now? How are you funding everything?

I have a CTO now. He bought out my old partners. He owns a chunk of my company, has savvy business sense and is the solution to everything that’s gone wrong with Cheek’d previously. It’s been a blessing.

So even though the sharks weren’t interested, this whole thing seems like it was a positive experience for you.

I remember after it had gone so badly, I walked out and I’m like, this has got to get on television. I don’t care how bad it was. I kept saying, “Do you think it was bad enough that I’ll get on?” I just want to tell people about what I’m trying to build…

… I just don’t want people feeling sorry for me. This is going to be life-altering in one way or another. I feel like this app is going to be a game changer. I think it’s going to be the next Tinder. Call me delusional, but we could be the next Tinder.

Here’s Ms. Cheek talking about Cheek’d:

Follow Jordyn Taylor on Twitter or via RSS. jtaylor@observer.com