Meet Tracy Benson of Obsesh. Obsesh is a real-time sports platform connecting consumers to top athletes and personalities. We had the opportunity to speak with their founder, Tracy Benson, to learn more about her wild journey from a college athlete to a digital pioneer to a visionary to a founder. You can follow her journey on LinkedIn and Instagram. Learn more about Obsesh, their team and their incredibly cool platform and follow them on LinkedIn and Instagram.

What’s your story? How did you get here?

Initially I was an athlete. I played volleyball for a couple of years after college but really couldn’t make any money. I thought it was just too early in the industry, but it turns out, 25 years later, there is still the same issue. I moved on and have spent a career growing and building consumer-led brands that are largely in the lifestyle space. I have an extensive background as a chief marketing officer and chief digital officer and now for the last several years as the CEO of a growing startup. 

For Home Depot, it was home improvement when I didn’t even own a home. I built and scaled that company as the first venture in my career and it was perfect. I turned my experiences as a competitive athlete into the competition of growing and scaling a business, and I did that for about 600 stores. In that experience I found my way into what I felt was a better point of view around marketing. 

I started out in the agency business in experiential marketing and then went into digital and then did all the traditional marketing and media. What I really loved was the ability to connect consumers and brands together around the right messaging, the right moments, the right activation and how to bring that to life.

During that time I went back for my MBA and I got practical experience plus the academic side and ended up being the head of digital for Best Buy. I helped build and set up all the systems that they have in place – mobile commerce, social commerce at the time, social media, customer support over social, digital advertising integration with our TV and our print and radio and our membership programs. It was great to start it, get it fired up and rolling. 

I mean, it was such a hairball for a big $50 billion company. The cool thing is I learned a lot, I did a lot and I made a lot of mistakes. Through it all I kept my passion in the sports and the lifestyle marketing space. I got to work with Beats by Dre when it was just a napkin idea and I got to leverage the power of Best Buy to do a three year exclusive to help it grow from $0 to their first $40 million. 

At that point I was kind of addicted. I was the startup engine inside that big beast. Skip ahead and I was able to take my startup entrepreneurial mindset to a high growth startup. Then I came back to my true love, helping athletes be able to connect, transact and create a financial future and do it with an “easy button.” After a long career in the digital space, I am now the CEO of Obsesh, a sports platform connecting athletes with fans and brand supporters. 

When you went out for funding, what did that look like?

This is a great and complex question as it has a lot to do with market dynamics and the problems you’re solving. When I first started out, my CMO mindset was, I gotta make sure there’s really a problem there before I invest my time, energy and money. I initially didn’t go for money, I spent my time on what is the problem? After twenty years, do we have the right to solve it? I spent about seven months testing ideas and working with a variety of athletes. At the time, college athletes couldn’t monetize themselves. We gathered all of this data and feedback and then tried to figure it out. 

As I figured out the business model, we took the route of applying for startup accelerators. We had a lot of people that were confused. They didn’t understand the sports business. They thought it was interesting, but they couldn’t wrap their head around a peer-to-peer model. 

There was one accelerator we wanted which was very sports specific. They’re the best in the world. They only accept 6-8 companies and you work very in-depth with their team, almost like an MBA. It isn’t cookie cutter. We got accepted into that accelerator program along with some generic business accelerators. We decided to go with Stadia’s accelerator and that really kicked off our funding. They led the pre-seed round. Coming out of the benefit of a demo day and having this entire industry help shape our model and poke holes, we raised a full round in four months. We used the funding to build out our minimal viable product (MVP). Now we are going out for our next round, a more formal seed round, but the market conditions are different which creates its own challenge. 

What keeps you up at night?

Trying to maximize our growth during really tough market conditions. For the first time, athletes in college can monetize their own marketability. It’s a super early evergreen market. On one side the complexity keeps me up at night on how we continue to educate and fund the resources to drive that education, and then the other side is that the fundraising environment is incredibly difficult. 

Have you had to pivot since your initial solution? 

Yes, I think we pivot realistically and in very micro ways almost everyday because we are learning new things. This is to be expected when working with a market that is used to dealing with regulation after regulation versus the now deregulated system. I pivot almost every day, however I think I’ve made two meaningful pivots. One is that initially our business model was based on a commission percentage of what athletes transacted in the marketplace. What we found was it was a slower market to get going, especially in the first many years. We had to add more to the revenue model and switch from just a commission base to a lower commission and a SaaS model because the upfront cost of getting athletes going was higher than expected. That was a big pivot for us.

The second pivot came about when we were initially focused on the pro market, the Olympic market and the independent niche athletes because niche from a marketability standpoint is where the passion lives. So the pivot came when the college market was deregulated. Similar to the cannabis market, it was all deregulated all at once. We shifted our focus to the college market due to pure volume. This deregulation came in July 2021. The college athletes just knew a jersey, they didn’t know they could monetize their name, image and likeness. The first year we had 227 great athletes express interest but then it got complicated when we went back to the school. The schools were telling them to just focus on being an athlete and that pulled the kids back. The first year we only saw about 5% of athletes and then the next year closer to 20%. We also saw athletes like women soccer players learning it wasn’t just for the quarterback of the football team. Real success cases are hard to wrap your head around when people are making $3 million or $13 million, they feel it is achievable for them. They didn’t realize they could come home with an extra $1,000 a month and that would be meaningful to them in college.  

Do you have any pets and or what is your favorite beverage?

I have a relatively new pet, Joan Jett. You can follow her on Instagram, she’s an Aussie Poo. 

What is your favorite beverage?

Gin and tonic with cucumber mint, no lime, Fever Tree Tonic and Hendricks. I love it.

Would you consider yourself a risk taker or how did you learn to embrace risk taking?

I’ve always been a risk taker. What I’ve had to learn to do over the course of my career is a balance of practical application with risk. My natural DNA is hard work, like an athlete. It takes 1,000 reps to get that one shot then it takes 10,000 reps to take it twice. I’ve always been the one to take the risk. I had to learn how through my MBA, my experience leading teams and building products and markets. 

What do you think is a misconception about being a founder? 

A few misconceptions are that it’s easy, you have all the time in the world and everybody will love your product. When it comes to fundraising, a misconception is that you just need a great idea and a great product.

What is something that fits into the “If I knew then what I know now” category?

I have a high tolerance. You can’t be a Chief Marketing Officer in a consumer led business and not work at 1000 miles an hour because it is such a dynamic marketplace. I feel like I’ve had more tolerance than most. What I know now is you have to have the most creative, strong team around you, especially when you’re smaller and more things are under a microscope. And so you have to play above your weight when you’re in a startup. I wish I had a really great business development and sales function. I also wish I could go back and be focused and framed on how you are doing your routines of the day.