When My Sugar Baby Became My Business Partner in a Tech Startup

Ever since I graduated from business school, I have been serious about wanting to start a tech company on my own. Originally, the idea was to do it with my best buddies from high school. We had always had the dream together when we were a group of four nerdy guys playing around with programming on my family's computer. Our idols, predictably, were Steve Jobs and Steve Wozniak, and we thought that the four of us would create the next big tech empire.

The thing is, people change. It’s something that’s been incredibly difficult for me to accept throughout my entire life, to be honest. For example, I took it as a personal affront when two of my buddies from this friend group told me that they were no longer interested in pursuing tech: one decided to become a high school teacher, and the other one went to culinary school. I put all my faith in the third friend who did actually go to business school with me, but then felt all the more devastated when he dropped out to take a stable job because his girlfriend got pregnant.

I’ll be totally clear about it: I had always been kind of a loner and an outsider, but losing those guys really shook my faith in other people. I felt like I couldn’t trust anyone, and that if I wanted to pursue a dream, I’d have to just do it on my own.

Well, something else that I realized is that being a tech genius will only get you so far. I had the skills to create something really good. But I simply couldn’t find a big idea that would translate into a successful tech startup because I had a hard time connecting with an audience. Who was my buyer? What did the consumer want? What was missing in the market?

I tried plenty of ideas and all of them flopped, one right after the other. I ended up taking a soulless job at a tech firm. And sure, the pay was exceptional; I was able to buy a house and a very expensive Dobermann Pinscher named Chance. But creatively, I felt like I had sold out, and I, totally unconsciously, blamed my old buddies for letting me down.

Anyway, that kind of lack of faith in humanity made it difficult for me to maintain a romantic relationship, as you can imagine. I opted instead for sugar dating, because it allowed me to go out on dates with beautiful women who told me exactly what they wanted and expected and were willing to offer. There didn’t have to be any emotional connection if I didn’t want there to be.

Of course, that changed when I met Judy. Actually, that changed when Judy met my dog. Most women who came over wanted me to put Chance in another room; he was quite intimidating, after all. But Judy instantly connected with him. And he immediately opened up to her, something that he didn’t often do with new people. Judy told me that she was trying to make it as a professional dog trainer, but was using sugar dating as a way to sustain her lifestyle until she could figure out a way to make a stable income.

I asked her what the problem was that was keeping her from doing dog training full-time, and she said that it was just difficult to compete with the thousands of free dog training videos online. No one wanted to work with an in-person trainer anymore, now that they were able to get free content from YouTube or a 30-second reel.

She seemed disappointed by the shift away from in-person training, and I asked her to elaborate.

“It’s just frustrating that people don’t recognize the benefit of one-on-one training. The online videos are far too general, and they don’t take into account the thousands of different variables that I’m trained to consider when putting together a training plan. Everything from the weather to the type of harness a dog is using to whether he’s slept well the night before can all factor into a training session. And I see it time and time again that people try using these overly general videos, and then the training doesn’t work, and they give up and put their pet up for adoption.”

I could see that Judy was visibly upset talking about this. I hadn’t met anyone so passionate about something in a very long time. I loved to see it, honestly. It was the first time in a long time that I also felt passionate about anything, and an hour before, I hadn’t really given much of a thought to dog training at all.

That night, I had trouble sleeping. I couldn’t stop thinking about what Judy had said about dog training. I was so restless that I went to my desk and started writing down ideas.

As soon as it was late enough in the morning to be polite to call, I asked Judy if she would meet me for breakfast. Which she did.

I think she was surprised to see that I had arrived early and laid out all of my papers of notes across the table. I explained to her, shuffling aside pieces of paper to make room for her coffee, that I wanted to start a tech startup with her. The idea was to create a platform of dog trainers who could offer virtual training sessions for a monthly fee. There would also be options for ongoing questionnaires and check-ins, progress tracking, and other features.

Once she had picked up her jaw from the floor, I could see that Judy wasn’t only flattered but also excited and motivated. She asked what she would need to do, and we spent the next two hours brainstorming and putting together an action plan.

That was two years ago, and I’ve been constantly surprised at how much Judy has filled in the gaps that I simply didn’t have the skills for myself. She brought the “human” element into every aspect of the platform. She was the one who knew what the consumer would want, what kinds of app features would be necessary for a successful training session, and how to make dog owners stay motivated. Without her, we would simply be recreating the many pre-recorded video platforms that already existed in the market. She was adamant about making the process personal, which meant that it catered to really serious dog owners.

But more importantly, Judy taught me how to trust people again and not just assume that everyone was flaky and out for their own interests. Her passion for dog training was inspiring to me, and it showed me that, for all the interest that I had in tech and business, what really lacked in my life was human connection. Maybe it sounds overly dramatic, but Judy renewed my faith in humanity, and I found myself eventually developing real feelings for her.

They always say that you should keep romance and business separate, but blending the two was the secret sauce I needed to finally get the tech startup I always wanted.

Oh, and Judy and Chance are still best buddies to this day. And he’s a much better-behaved dog as a result!