The College Grad and the Tech Visionary

When I was in college, I was on top of the world. I was excelling in all of my classes. Playing collegiate softball. I had a ton of friends. I was living in a bubble, and I loved my bubble. It was the best.

Of course, bubbles pop, and graduation was a big wake-up call for me. My friends, who had studied microbiology, political science, and applied mathematics, were all going on to internships or right into the workforce.

I was…not.

I had nothing lined up. I had studied communications, which I thought would have opened me up to many different avenues, but in reality, only made my path vague and undetermined. Many of the job listings I applied for wanted more specialized studies or experience in the field. Luckily, I had a waitressing job, and my rent was paid through the summer, so I just told myself to stay calm and trust that the universe had something waiting for me.

As it turns out, the “something” was actually a “someone,” named Mervin.

Mervin was my sugar daddy, but before that, he was one of my most faithful customers. I had started sugaring about a week after graduation and happened to see Mervin, whom I recognized from work, on the sugaring site that I was using. My college town isn’t that big, so I knew that he likely already saw my profile, and in order not to make it weird at work the next day, I sent him a playful message, something like, “Fancy meeting you here!”

His response was really sweet, actually. He said that he had always found me to be beautiful and would love to have a date with me. But he didn’t want to make things awkward for me at work and would be happy to change diners if I felt uncomfortable.

I told him not to worry about any awkwardness and that I would be sad if he switched diners. “You’re a good tipper,” I teased him. We set up our first date for a couple of days later and thus started my one and only sugaring summer.

I say one and only because it’s been five years, and Mervin and I are no longer in business together, on any front. Let me explain.

That summer, he had told me about how he was ready to build his own start-up but didn’t know what to focus on. He had tried blockchain and hit a wall. He had considered starting his own sugar dating site, but changed his mind. He was throwing ideas at the wall, and nothing was sticking.

During most of these conversations, I stayed pretty quiet. I wasn’t really sure how to advise this wealthy tech guy as someone who was fresh out of college and, frankly, broke. So, I listened and nodded and asked follow-up questions as best I could.

This all changed when one day, I showed up to our date with my phone in my hand. I try to never be distracted on a date, even when we’ve been seeing each other for a while, but I had been going back and forth with this guy about renting out a baseball field for a softball tournament I was organizing. He was so flaky and kept changing the rates on me, so I had been scrambling trying to find another venue. And with summer coming to an end soon, I was so stressed and doing everything I could to just make sure this one last tournament went well.

Mervin was more than understanding. He seemed really interested in my predicament. He had all kinds of questions about how often this happens, and what the protocol was for deposits and cancellations. Were some fields better to play on than others? And had any fields ever been double-booked?

I wasn’t sure why Mervin was so invested in this softball drama; it seemed beneath him, but I was grateful that he was nice enough to pretend to care. What I didn’t know was that Mervin was actually following the thread of an idea, one that would change both of our lives.

Mervin showed up to the softball game that weekend, which was sweet. I don’t even remember what the final score was, but I remember him sitting in the stands in a suit and baseball cap, looking like somebody's uncle. It was adorable. He bought a few rounds for the whole team at the bar afterwards and then took his leave so that “us young gals could go crazy without a chaperone.” I walked him out to his car.

That’s when he told me that he had a new idea for an app, one that he was sure was going to work. He looked surer and more excited than I had ever seen him before, and I asked for more details.

“Let’s have lunch tomorrow, and I’ll tell you everything.”

I’ll admit that I had partied a little harder with the girls after the tournament than I had anticipated, so I showed up to our lunch date with sunglasses and a big bottle of ice water. But what Mervin told me next completely shocked me out of my hangover.

“I’m starting an app where local sports teams can rent out venues for their practices and games. And I need you to help me.” I was sold before he even finished the full pitch.

Over the next year, my job was to be Mervin’s liaison between sports venue owners, as well as oversee our marketing strategy. It was a lot of work for one person alone, but I left my waitressing job to jump on the project full-time. Mervin made it easy: he paid one year of my rent up front and started paying me for my work right away. He said, “If it’s not off the ground in a year, we’ll find you a fancy office job in marketing.”

And of course, Merv and I were still sugar dating, which might have complicated things if we weren’t such a good pair. We set up some pretty good ground rules right from the start that would allow us to separate our dating life from our professional life. In other words, when we were on a date, we didn't talk about work. When we were at work, people thought we were a traditional couple, but there was no PDA or anything inappropriate.

By the end of the first year, it was clear that this app was going to stick around in a big way. Everyone I knew who played sports was on the app, and we were expanding to major cities in the area. We were hiring new people all the time, and now I didn’t have to reach out to sports venues; they came to us. It was only a matter of time before the app really found its wings and went national. I could feel it.

And I was really proud of what we were accomplishing. It was incredible, honestly. But it never really felt like mine. Yes, I was the inspiration, and I helped get it off the ground. But I also wasn’t ever totally comfortable with the fast-paced, stressful start-up environment. It was starting to get to me.

At the start of the next summer, I sat down with Mervin to talk about how I had been feeling. I made sure to tell him how grateful I was for everything he had done for me. I literally would still be waitressing and applying for jobs if it weren’t for this break. But I told him it was time for me to move on. I wanted to start my own career before this one made it impossible to leave.

Mervin was initially upset, I could tell. He had heard no from so many people over his years in tech start-ups, and he didn’t think that his close business partner would also say no to him. But he gathered himself and pulled me into a hug.

“I want to introduce you to someone in New York. Let’s start planning a trip.”

As I said, five years later, Mervin and I aren’t working together anymore. The person he introduced me to in New York was the CEO of one of the marketing agencies I most admired. I never thought they would ever let me in the door, let alone hire me. But they had already heard about Mervin’s new app and were impressed by our first-year marketing strategy. They took me on for a trial basis, and I was officially hired two months later.

Mervin and I still talk, from time to time, although we ended our sugar relationship when I moved to New York. Whenever he’s in town, we always make a night of it, and I get to hear all about whatever new start-up he’s working on (he sold the venue rental app at just the right time, savvy businessman that he is). Sometimes I feel overwhelmed by how much he’s done for me, but he always reminds me, “You did all of this yourself. I was just the person who bet on you. I know a good investment when I see one.”