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How I am seeing the field across sports, media, entertainment, wellness and CPG

March Madness is in full swing. Brackets are busted (Sorry Gator Nation), buzzer-beaters are flowing and Massachusetts’ own AJ Dybantsa showed why he should be the #1 pick in June. What’s missing? The Cinderella story… unless you want to count the 11-seeded Texas Longhorns as that. 

In 2025, there were just 13 “upsets” - tied for the fewest since 1985 and the Final Four featured only No. 1 seeds. Last year was chalk, and this year is trending the same way (12 upsets so far with Texas and Iowa accounting for 4 of those). The magic isn’t really disappearing, it’s merely being bought out. We all know it and see it. 

This edition won’t be a discussion on the lack of mid-major upsets and the state of the transfer portal… though I’d be happy to give my $0.02 on that over a beer with any of you. 

Let’s focus on the economics at hand. The bill for college athletics has come due - and more schools than you’d expect have no idea how they’re going to pay for it.  

We’ve covered the shift to a revenue-sharing model and that schools are now ‘permitted’ to directly pay athletes up to $20.5mm annually. That’s already table stakes to run a competitive program. Here’s the issue though: most schools were losing money before this mandate launched. 

In 2023, the average FBS athletic department earned $79mm in revenue and spent $98mm. Playing this example out, that’s a $19mm deficit for schools that now adds in a $20.5mm revenue-sharing distribution. Pretty quickly this ‘average’ institution is staring down a $40mm deficit. Washington State Senator Maria Cantwell laid this out in stark terms in her open letter to D1 university presidents.

Now, let’s look at some individual schools. The numbers are still staggering. Michigan faces a projected deficit of nearly $27mm for the 2025-2026 academic year, on top of a $19mm YoY revenue decline since they had one fewer home football game. Colorado is in a similar boat. Even with the Deion “bump”, the university's preliminary budget shows a $27mm shortfall as athletic expenses project to hit a record high by more than $20mm. Schools aren’t keeping the need for additional revenue quiet either - check out the announcement on Colorado Athletics official website:

Academic leaders across the country are noticing this as well. Karen Weaver, a director of the collegiate athletics certificate program at the University of Pennsylvania said “Every school is going to have to look at its financial statements and make decisions on endowment spending or even cutting programs to sustain athletic revenue-sharing models…The sector is already under tremendous financial pressure.”

Here’s what I am looking at: the schools that are moving the fastest aren’t waiting for alumni to donate more or hope that the media deals can make up for it. They are starting to think like businesses themselves. 

In April 2025, Kentucky created Champions Blue, LLC — transferring its entire collegiate athletics operation into a new entity. Boise State, Clemson (Clemson Ventures), Michigan State (Spartan Ventures), Texas Tech, and West Virginia have all recently formed LLCs or forged partnerships with private entities to house the commercial arms of their athletic programs. Utah has taken this further than anyone, as they are set to seal a $500mm+ capital investment from Otro Capital, a sports-focused PE firm founded by former Redbird Capital executives. Alexander Baker of Millennial Mandamus put together a great visual for this Otro x Utah tie-up:

These moves make a lot of sense structurally. But a re-structure and injection of capital doesn’t solve the bigger issue: schools still have a long-term revenue shortfall. They need to leverage their brand power and athletic prowess to create new, stable and recurring ways to generate revenue. If not, significant changes like cutting sports or departments are coming.

Think about what major college athletic programs actually have: millions of passionate alumni. A brand with emotional equity. Content. Events. Relationships. Loyal communities that rival professional franchises. And yet, only a seemingly small percent of that loyalty has been turned into a real revenue driver for the school.

The schools that figure out how to activate their fan and alumni base as a commercial engine and not just a donor list will build a real structural advantage. The ones that don't will keep running deficits and making increasingly desperate moves to fill the gap. That’s exactly what Waypoint is building for - every Athletic Director and Chief Business Officer should be taking that meeting.

A mini investment memo on the stars of tomorrow

The Company: Waypoint

The Business in a tweet: College fan loyalty is one of the most monetizable assets in America and nobody has cracked it yet. Waypoint thinks travel is the beachhead, building the infrastructure later that makes its purpose-driven Crowd Commerce approach scalable across college athletics. Through a university branded travel booking portal for universities, alumni and superfans can combine savings on their travel and lodging plans with the satisfaction of their school getting a cut of every transaction.

The 101: 

If you are interested in learning more about Waypoint or want to speak directly with the management team, please respond to this email or reach out directly to [email protected]

Comparables:

📶The Signal (No Huddle’s Take):

Major college athletic departments are sitting on one of the most concentrated loyalty assets in America. Thousands of wealthier-than-average, emotionally engaged alumni and fans, with almost no commercial infrastructure to engage them beyond a “donate here” button. 

Here’s what makes Waypoint’s model structurally different from every other revenue solution being pitched to athletic departments right now: it doesn’t ask fans to do anything new. They don’t need to donate more, show up to another event or buy another package. Waypoint is simply meeting fans where they are and when they are spending - take the trip you were already planning, just book it through this portal. That’s a fundamentally different psychological proposition, and the BYU conversion data suggests that fans get it immediately. 

This structural change in college athletics is inevitable. We are seeing a surge in colleges spinning out commercial arms, hiring business-focused personnel, and in some cases taking on outside capital. NIL-era financial pressure is real and the multi-million dollar annual gaps don’t close themselves. Waypoint has the product-market fit and is ready to help with a white-labeled solution right now. 

The early BYU data is no fluke. A 6% booking conversion rate, under $3 cost per registration, and 94% re-book intent proves that the thesis is directionally correct. People will redirect travel spend to support their school.

What’s also easy to miss in those numbers is the data flywheel being built underneath every booking. Every booking teaches Waypoint something about high-income fan travel behavior that no one else has. The 10th, 20th, 50th schools on the platform won’t just add revenue, they will all see sharper targeting, better campaigns, and higher conversion. It looks like a travel booking company. It’s actually a compounding data business. 

The NIL angle is also a sleeper. Waypoint’s model gives every athlete trackable earnings tied to something they feel comfortable naturally promoting. That’s a smarter pitch than another NIL package built for a five-star recruit.

Waypoint’s product roadmap also gets me excited. Can they create a “bucket-list” experience that helps fans get tickets, transportation, lodging, and tailgates all in one place while also kicking back proceeds to their school? Can they ink a credit card partnership that “boosts” points for bookings made in the portal, giving fans yet another reason to book here and not through Expedia? 

University sales cycles are slow by nature, but Waypoint's white-label model is designed to reduce friction, and the financial urgency schools are facing right now is doing some of the selling for them.

If you are an early-stage investor, involved in college athletics or have a strategic relationship into the space, you need to take a deeper look at Waypoint. The thesis is clean, the data is early but real and the upside case is one of the more interesting ones I’ve seen in sports tech. 

If you’re interested in learning more and meeting the Waypoint team, respond to this email or reach out to [email protected].