When the Student Became the Teacher: How I Taught My Sugar Daddy to Rebrand His Business for the Digital Age

When Phil and I met, he was doing well for himself. He had a personal training business that was beloved locally, and he had a loyal following. Even past students who had moved away would regularly call him and ask him to put together training plans or just to talk about how their progress was going. And he had quite the roster of famous or wealthy clients who kept him in a good place financially.

I mean, he was doing so well within his niche that he had enough expendable income to take on a sugar baby, yours truly. It’s not like I had any really extravagant needs by any means. I was happy with a middle-of-the-road arrangement: an allowance that would help me move into a slightly bigger place and cover groceries and salon appointments.

Phil also offered me free personal training, which was a huge plus. I loved how technical he was in his approach and how he was able to explain kind of complicated concepts in layman's terms.  By the end of each training session, I knew exactly why we were working on certain muscles or areas of the body and what I could do for recovery. It was very different from every trainer I had before, who had just told me, “Do these 5 reps and then do these 5 reps, and then we’ll call it a day.”

Clearly, Phil was doing something different, and his passion shone through his work.

But after dating Phil for a few months, I could tell that he was struggling emotionally. He was frustrated. He wanted to expand, but he wasn’t even sure how to do that as one guy. Like, he could train others in his style, but how much can you really scale up when you’re expanding one trainer at a time?

At first, I didn’t give him my opinions because I know sugar babies who have pissed off their partners by coming in with unwanted advice. But Phil started asking me what I thought, and if I had any ideas.

Mind you, Phil had zero online presence at this time. He was working entirely through word of mouth, and he was just lucky enough that his wealthy clients were willing to recommend him to other equally wealthy new clients.

So, when he asked me if I had any ideas about how he might move forward and reach more people “my age,” I told him the truth. He needed a social media presence. He needed a website. He needed to give people the option to book online for a free consultation.

At first, he kind of pushed back and told me that what he really valued was face-to-face interaction. He didn’t like the idea of being in front of a camera or talking to people through a screen. I reminded him that it was one of the best ways that he would be able to connect with a larger audience. And that people would really benefit from his style. He said that he wanted time to think about it, but he came around fairly quickly. Of course, he had no idea what the next step should even be.

“This is your world,” he told me, “Can you help me?”

And that’s how I became Phil’s social media manager.

To be sure, I didn’t go into sugar dating because I wanted to take on a full-time or even part-time job. Just like Phil has his talents, my talent is being an excellent sugar baby, not a social media manager. But I have to admit that I liked it more than I expected. I would spend a couple of days a week following Phil around to his different sessions and filming him while he worked. And, because he had such great relationships with some of his more well-known clients, we got some seriously major viral videos early on.

Before long, we were monetizing long-form videos on YouTube and accepting brand deals on social media. And of course, Phil was also staying true to his in-person clients and taking on even more as he got more name recognition.

As Phil got more and more successful as an influencer, the dynamics of our relationship changed, too. I don’t mean that in a bad way, necessarily. As the money came in, Phil made sure that I was getting a fair share plus extra. And we started to see each other as business partners. Any kind of decision that he had to make about his personal brand was something that he would bring to me first. He was the star, of course, but he trusted my judgment above anyone else’s. And he made sure to tell me often how big a role I played in him reaching his goals of expanding.

Looking back, I can also recognize how much I helped Phil, especially in those early days. He was pretty awkward in front of the camera and didn’t know what to say or what kind of content to create. I was always there with some jokes to loosen him up and a general outline of what each video should include.

But it got to a point where I didn’t really want to do it anymore. It’s not that I didn’t like it or that Phil was hard to work with. It just took away all of the romance between us. I stopped getting excited about dates that we would plan that would be outside of working hours because we would inevitably talk about work anyway. For any romantic vacations we planned, we had to make sure there was content creation built in.

I was starting to burn out, and perhaps not surprisingly, Phil was the first person to notice. And it wasn’t because I was getting snippy with him or doing a bad job. It was actually because I was struggling with the personal training. Working out was feeling like a total drag, and I started dealing with some injuries that I had never had before. When it came to weightlifting, I was plateauing, and Phil could see it.

After a workout one day, as Phil was helping to massage my shoulder that was giving me trouble, he asked if there was something I wasn’t telling him.

“Sometimes,” he said, “Our bodies do a better job of telling us when it’s time to make a change before our brains catch on.”

I was kind of surprised by the words that came out even as I said them: “I think maybe we should break up.”

Phil was totally taken aback. Just like I was. He took his hand off my shoulder.

“No, I don’t know if I mean that,” I said immediately. “It’s just that this is kind of straining to be both your sugar baby and your business partner. I feel like I’ve been a better social media manager and let the romance and the fun go to the wayside. And, so have you. I don’t want to hurt your feelings, but it’s true. I care about you a lot, and I’m not ending things. I just think maybe one part of our relationship should change, or end.”

Phil leaned back and put his hands over his face. At first, I thought maybe he was crying, but when he lowered his hands, I could tell that he was smiling in relief.

“You scared me,” he said. “I’m so glad you said something because there’s something I’ve been wanting to do for a little while now, and this is the perfect chance.”

He reached over and grabbed my hand.

“You’re fired,” he said. “Not as my sugar baby. As my social media manager. I can hire someone else. Your allowance will stay the same. But you’re right. I’ve been expecting you to take on roles that are totally unreasonable. You’re awesome in this role, don’t get me wrong. It’s going to be a pain to find someone who can fill your shoes. But I want you back. I want to enjoy this with you.”

To celebrate, we booked a trip to the beach and started drafting a video that would explain why Phil would be off social media completely for two weeks. I was so excited to go back to being the sugar baby, the workout student, the mysterious girl who would sometimes show up in the background of Phil’s videos.

It was exactly where I wanted to be.