Episode 1: Mit Winter • Creative Contract Construction

Moneyballers: Inside the College Front Office

Episode 1: Mitt Winter on NIL, Revenue Sharing, and College Front Offices

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Introduction

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Welcome to Moneyballers: Inside the College Front Office.

We’re your hosts, Nick Siscoe and Luke Bogus, co-founders of Dropback.

With the revenue-sharing era of college sports upon us, championship-caliber teams will be fueled by creative, competitive, collegiate front offices.

Here on Moneyballers, we'll be learning from the brightest minds and emerging innovators in the new College Front Office, with the goal of equipping our listeners with tools and tips to give their teams a competitive edge.

Our first guest is none other than Mitt Winter. If you follow NIL on Twitter, then you already know Mitt – one of the most prolific voices in sports law. Mitt is an attorney at Kenny Hertz Perry Law and a partner at Winter Sports Law. He collaborates with athletic programs across nearly every major conference to navigate the new era of college sports and help them find competitive edges within the bounds of ever-changing rules and regulations.

Luke and Mitt dive into a wide-ranging conversation – from creative revenue-share contract construction to how schools are navigating athletic reputation within the guidelines of the NCAA’s NIL bylaws.

There’s a lot to cover, so let’s get into it!

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Guest Introduction

Luke: Mitt, welcome to the Moneyballers podcast. Thanks for joining me, man.

Mitt Winter: Yeah, thanks for having me on. Appreciate it.

Luke: Pumped to dive into this. You’re one of the foremost voices in the NIL space, so let’s jump right into it.

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Question 1: NIL Evolution & Preparedness

Luke: You’ve been in this industry for a long time. You saw NIL come up in 2021, and now with revenue-sharing on the horizon, you’re seeing even more changes. You’ve worked with a lot of collectives and schools.

How is the way schools are preparing for revenue sharing now different from how they prepared for NIL back in 2021?

Mitt: Yeah, I would say the big difference is that now every school understands that NIL is going to be a huge part of running their athletics programs moving forward.

When July 1, 2021 hit and the NCAA NIL rules changed, there was wide variation in preparedness. Some schools were doing nothing; others had been planning for a while. Back then, schools were caught a bit off guard, especially with the interim policy that came into play after the Alston decision.

Now, though, schools are taking NIL very seriously. Even though the House settlement hasn’t been finalized yet – and may not be until April or May – schools are already planning as if it’s going to happen. Everyone’s getting their NIL compensation plans in order.

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Question 2: Cutting-Edge Strategies

Luke: That’s super true regarding the increased preparedness. But there’s still a lot of variability in how schools are approaching NIL.

On one end, there’s the basics – how much to spend on football versus basketball, men’s versus women’s sports, etc. But what are some of the more cutting-edge strategies or innovative things you’ve seen schools doing to get ahead?

Mitt: I think the most interesting thing right now is how schools are valuing their athletes. That runs the gamut from:

• Coaches simply saying, “We think these are the most valuable players or positions”
• To using advanced third-party tools to project and quantify value

There’s a lot of variability in which tools schools are using, and that’s where some schools are trying to gain an edge. As you know, the House settlement imposes a finite cap on NIL compensation. That means schools need to make smart decisions about how they allocate those resources – both across teams and within teams.

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Question 3: Cap Circumvention Strategies

Luke: On that thread, when the House settlement news broke, it didn’t take long for people to start talking about cap circumvention strategies.

Is that going to be as prolific as people are predicting? Or do you think most programs will stick to the rules?

Mitt: I think it’s TBD. A lot will depend on how effective the new rules around collectives and booster involvement will be. If the rules are strictly enforced, and people realize collectives can’t operate like they used to, the cap could hold up.

But if enforcement is lax, you can bet some programs will test those limits to stay competitive – especially at the highest levels. It’s another uncertain period where being a little more aggressive could give you an advantage.

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Question 4: The Next Arms Race

Luke: In the past, the arms race in college athletics was about:

• Pre-2021: Building the best facilities
• Post-2021: Raising the most money to pay athletes via NIL

Post-2025, if the cap holds, the arms race shifts. What’s the next big battleground for competitive advantage in recruiting?

Mitt: It’s going to come down to two main areas:

1. Resources to hit the cap: Schools need to ensure they have the funds to hit the cap as it increases over time.
2. Third-party NIL deals: This includes working with collectives, securing brand partnerships, or helping athletes find NIL opportunities.

A good example is Memphis and their deal with FedEx, where FedEx puts significant money into NIL deals with Memphis athletes. That’s a differentiator.

Another area is the contract terms schools offer – such as including bonuses or creative structures to incentivize athletes.

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Question 5: Front Offices in College Sports

Luke: I saw that Clemson just announced they’re formally building out a front office for their athletic program. Is this going to be a trend?

Mitt: Yes, but it’ll vary. Some schools are saying, “You’re now the GM,” but those people might lack personnel experience. Other schools are hiring individuals with NFL or pro sports backgrounds to run their front offices.

I think over time, more schools will adopt the latter model because managing NIL contracts is a huge job. Schools are essentially combining multiple pro sports teams (football, basketball, baseball, etc.) into one program and asking someone to negotiate all those contracts. It’s a massive undertaking.

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Closing Thoughts

Luke: Mitt, this has been super valuable. Any final tips for athletic departments navigating this period?

Mitt: Just use all the resources you have available right now. We’re in a transitional period as schools move toward House settlement implementation and away from collectives. Things will likely get smoother over time, but for now, it’s all about navigating these next 6-12 months as effectively as possible.

Luke: Thanks, Mitt. Appreciate your time.

Mitt: Yeah, thanks for having me on!

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Outro

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