A note before we begin -

In August of 2023, while I was bouncing around the NFL, I took my first job in sports, media, and entertainment investing.

By this point, I had a firm grasp on the broader VC world, especially its intersection with human performance technologies and other sport-adjacent categories, but nothing had prepared me for what I was stepping into.

The institutionalization of sports as an asset class was happening in real time as the Big 4 was fresh off of opening up to private equity investment, dozens of emerging leagues were launching week after week, and new funds began flooding the zone.

I wanted to better understand the industry from the ground up, and I had just written my 60-page Senior Thesis on “Venture Capital Decision Making Following the Burst of the Dot.com Bubble” at Princeton University, so naturally I felt the compulsion to dive into the data in search of the patterns underneath it all.

Over the following two months I wrote a research white paper on the “Future of American Sports Investing,” and I titled it Evolution.

This white paper set out to articulate my understanding of the evolving landscape of the burgeoning sports, media, and entertainment asset class.

I didn’t know it at the time, but this exercise would go on to build the foundation of my career as a sports investor and lay the groundwork for what would eventually become this publication, 🧭 At the Center.

It’s now three years later, I just got married, took some time off, and just got back and settled, so Part IV now delivers the debrief.

To prepare for this essay, I printed off the original Evolution white paper and took a pen to it.

I graded it just as I would any other investment thesis, and what followed was an inspired hour of ideating on the patterns that have shaped the evolution of sports as an asset class in recent years.

Unlike Parts I – III, this paper is written by me in present day (September 2026) and is actually informed by multiple years of boots-on-the-ground experience as a sports private equity investor.

I have cut my teeth, got my deal reps, built my network, gone down year-long rabbit holes (college athletics), built a publication and podcast engine, and learned a ton in the years since.

So today I impart some of that knowledge onto you, my reader.

Here, is where I will tell you where my original thesis was right, wrong, and where I completely missed.

Class is in session, let’s begin. 📝 📝 📝

🎙️ I’m back!

+ Brent Peus and Dominyck Bullard brought the HEAT with one of the best theses I’ve ever heard surrounding Emerging Leagues as IRL Marketing Ecosystems. Check it out!

What held are the structural claims I made, underneath which sits what I am naming “the pattern of endurance.”

Endurance is the property an institution acquires only by surviving time, and it cannot be manufactured, accelerated, purchased, or delegated.

Tradition and history are not manufacturable overnight. Properties accumulate meaning and cultural relevance over time, regardless of the amount of capital raised or virality of its content.

The Masters and Wimbledon are enduring. LIV Golf clearly is not.

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My first observation is that most of what I got right in my original thesis were observations of endurance. These are still true in 2026 because they are timeless.

My argument in 🧭 Monopoly (Part I) was that sports as an asset class has exploded because sports are uniquely monopolistic in nature and that there are a convergence of trends deepening that monopoly.

This monopoly clearly still exists across three dimensions:

Live sport remains the only reliably scheduled mass gathering of simultaneous attention in a fragmented attention economy, and its scarcity has only gotten more disproportionate, which is precisely why the valuations of these franchises continue to climb.

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I said, before AI reached escape velocity and the Enhanced Games spent $250k on AI clip farming. Not to mention the pounding of the “AI vs. Anti-AI” drum by sports investors everywhere.

The NFL now sits at 9 international games per season across 4 continents, and Roger Goodell has been sure to let everyone know that a non-US franchise is to be expected. If I were a betting man, I’d put $10 on that happening before his brand new contract extension (which is 95% incentive based) runs out in 2031.

The MLB is dominating East Asia (thank you Ohtani and Yamamoto), and the NHL's 2025 4 Nations Face-Off (USA vs. Canada vs. Finland vs. Sweden) was the highlight of the 2024-25 season.

Three months after writing this, Shohei Ohtani signed a $700M contracts with the Dodgers and the entire continent of Asia made a mass exodus from Anaheim to Elysian Park.

And while I never could have predicted Taylor Swift in a million years, one 3-year, $100M Amazon Wondery deal later and the Kelce brothers are officially America’s darlings with a new media property for the ages.

Media rights escalation held for all of the reasons the paper stated, capped off by the NBA's 2.6x re-pricing upwards to $76B over 11 years. Streaming has entered the space in a BIG way:

The U.S. blew through the original forecast of a $30B sports media rights market by 2025, and now it only costs $1000 across 9 different platforms to watch every NFL game this year :)

Read this JP Morgan Sports Media Almanac for a killer breakdown.

The punchline: the Big 4 will keep compounding because 5 buyers cannot afford to lose them, but every second-tier property that cannot assemble at least 3 bidders is already deflating.

While I completely missed on prediction markets (more on that later), Nick Jonas and Kevin Hart have been driving around on my TV in their 30-second commercial screaming at the top of their lungs that “DraftKings is available in all 50 states.”

A recent Betterment survey of 1,000 retail investors found that 52% of Gen Z investors have redirected money intended for investing toward sports betting, and 26% of Gen Z investors treat sports betting as "a deliberate part of their long-term financial strategy."

Oof.

Bingo.

Stan Kroenke and Jerry Jones are in a fight to the death over who is the better horizontal integrator, and while Stan owns more real estate than most governments, I might have to tip my hat to the man behind “America’s Team”.

The Dallas Cowboys are the Disney of the NFL.

Disney takes owned-and-operated IP (Snow White) and launches a movie, a record, merchandise, and eventually a ride at Disneyland. 

Each node monetizes the same core IP in a different form . . . the classic "Disney flywheel" business model.

The nodes eventually out-earn the core IP, because core IP is capacity-constrained.

The Cowboys' core IP is football in Dallas on Sundays. They have a monopoly on that IP, but it caps out at just 8 home games per year.

Everything else is the platform: Real estate, catering, corporate hospitality and events, Miller (not Bud) Lite, a Cowgirls series on Netflix, WrestleMania, Final Fours, and TX high school football championships. 

All of it is the IP flywheel of "America's Team."

The most profitable franchise in sports, and the core IP is the smallest part.

The Jerry Jones playbook is now being replicated by every single Big 4 and Tier 1 European soccer club, not to mention the light speed at which every Power 4 University in the country is adopting versions of this idea.

Like I said, bingo.

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These hit because they were structural observations of what is enduring downstream of examining why they have already endured throughout history.

I have the receipts to officially prove that I was an early pioneer of the NCAA to English Premier League historical parallel, and I’m here to collect my flowers.

I mapped a 3-wave sequence for the amateur to professional arc of the Association:

While the Super League + CBA has yet to be resolved, the others held:

This truth, when applied to the WNBA, helps explain why Cathy Engelbert just announced her "retirement" and why player-centric, equity-heavy leagues like Unrivaled and Project B have been able to get off the ground.

The balance of power in basketball, and the subsequent leverage that the player associations have, is just different when compared to football.

The NFL continues to demand more from its players (hello expanding international slate + an inevitable 18th regular season game) because they can, and in 2024 they finally began financing like a corporation by opening their cap tables up to private equity (alongside new tech billionaires entrants).

Meanwhile Kawhi Leonard got a $700K slap on the wrist, and Steve Ballmer flipped a nickel ($30M) to the NBA league office on top of five forfeited first-round picks and a one-year suspension.

As the MLB CBA negotiation plays out in real time, with owners pushing for a hard salary cap and a lockout looming, most players will wish they had the same leverage as the NBPA.

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I got almost all of these wrong, some of which I got really wrong.

The PLL stands as the lone survivor of emerging leagues I was directionally correct about thanks to this year’s $100M Series E led by Joe Tsai and Ares.

We will get to why all of my predictions failed down below.

Hint: they aren’t enduring.

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Jason Wright at Project Level would tell you that women's sports assets resemble small-cap stocks with high growth potential.

Monarch Collective and Alexis Ohanian would both agree with him, as each have poured millions of dollars into blue-chip women’s sports assets over the past 3 years.

A few highlights:

And of course I’m missing plenty of other examples. Women’s sports are hotter than ever, and franchise valuations have climbed even higher than anticipated just 3 years ago.

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Now for my favorite part, my failures!

Turns out that when I first got into sports investing, the only thing I could wrap my head around was the TopCo. → franchise model.

I thought it was the only path forward for emerging leagues, and while some have executed on it, it's safe to say I missed on a lot because of it.

My "franchise fallacy" assumed that franchises are what create fandom, but turns out it’s the other way around.

What I have learned since is that most of these emerging leagues have a relationship with their fanbase that is predicated on content, not on ritual and ceremony.

Instagram, TikTok, YouTube and every other digital touch point will absolutely pique Gen Z's interest, but that interest has no staying power, because those fans aren't participating in the rituals, tradition, pageantry and heritage of the league the way they would with college football, for example.

If you’re just content, you’re just content.

And that translates to an audience whose stickiness depends on the next dopamine hit, which is not a long-term strategy.

If you are not building something enduring, then you won’t survive.

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Wrong.

In November 2025, Apple and the MLS agreed to tear up the ten-year contract early, ending it after the 2028/29 season instead of 2032.

Season Pass, the paywall my entire thesis rested on, is gone. Every match now sits inside a standard Apple TV subscription, and while the MLS will collect roughly $50M more over the shortened term ($200M for 2026, $107.5M for Feb-May 2027, $275M for 2027/28 and 2028/29), Apple got its exit clause.

The MLS got the boot the second Apple realized the league could not, on its own, move subscriptions for them.

Apple opted instead to put Brad Pitt in a rocket ship with wheels, make a summer blockbuster about it, and then go buy the rights to something sexier. One five-year, $750M deal later, F1 is the crown jewel of Apple's sports strategy and the MLS is bundled inventory.

As for the state of soccer in the U.S., it seems to be the case that the Messi hype stayed rather local to Miami.

And while the World Cup was electric for a few peak summer weeks, it is hard to tell what degree of long-term effect it will have on the MLS. Grassroots development is measured in years.

Larry Berg was named to succeed Don Garber as commissioner in 2027, so I feel good about the overall direction of the league. But he will have his hands full given the mess that the Vancouver Whitecaps are in, so stay tuned for what happens there.

Takeaway → streaming is not an automatic win for emerging leagues.

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This didn't happen (yet), and I did not expect them to launch the WLL.

Their $100M Series E, led by Ares and Joe Tsai, was underwritten on the PLL remaining a TopCo. model for a little while longer. The tour format turned out to be the thing keeping the engine humming, not the thing holding it back.

Takeaway → tour format > TopCo. → franchise model

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The contrast to the PLL is the MLC, which was much quicker to franchise after raising $120M in 2022 to launch, backed by Satya Nadella and Ross Perot Jr.

The six franchises all operate independent P&Ls but play centrally at Grand Prairie Stadium outside Dallas each June and July, collectively sharing ownership of the venue.

There is a mandate from the MLC for each franchise to build its own cricket-specific stadium in its home market within the next few years, which means five of the six will divest their ownership in Grand Prairie and roll those proceeds into a new build elsewhere.

That should act as a catalyst in those markets, but the MLC has clearly struggled to keep pace with the rest of the global game:

The 2024 T20 World Cup, which the U.S. co-hosted, came and went. It was the most-watched edition in the tournament's history (500 million), and it added almost nothing to the MLC.

That gives me real concern about how much cricket's inclusion in LA28 will actually do for the league.

While the MLC does technically, and in practice, have a monopoly on the sport of cricket in the U.S., the uncomfortable truth is that a legal moat adds minimal incremental value when you are building a league for a niche sport that caters to a niche diaspora.

The IPL will compound forever because they sit on an entire subcontinent that already has the obsession. Building that from scratch is very difficult.

Takeaway → a legal monopoly is only worth the TAM underneath it

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The MLP doesn't exist anymore.

After running a promising "pickleball is taking over America" campaign from 2021 to 2023, it turns out that mass participation struggles to convert into a successful professional league.

A few reasons why I think that is:

The MLP had to merge with its rival, the PPA, into the UPA in 2024, and then fold that combined company into a rolled-up HoldCo., Pickleball Inc., in 2026, in order to raise the capital the sport's ecosystem needed to flourish.

Pickleball Inc.: a tour and a league (PPA Tour and MLP), a retailer (Pickleball Central), a software provider, a media arm, a court builder, and stakes in Picklr and DUPR, on a combined 2025 revenue base north of $140M.

$225M from Apollo Sports Capital will go a long way. But I would venture to say that Apollo underwrote the consumer businesses in the HoldCo. and treated the league as the marketing budget.

This reminds me of how the initial investors in LOVB underwrote the youth development and academy system, with the pro league as the cherry on top.

A precise inversion of my original thesis, which held that the league was the asset and the ecosystem was the halo.

Meanwhile the APP Tour, run by my good friends at Intersport, is raising more hand-to-mouth and is focused heavily on the Asian market. No franchises. Instead they are trying to be the ATP of pickleball, a live event touring model. I think that could be the better bet.

Pickleball will always have to fight a characterization of amateurism, and as tennis and padel come roaring back, the air is getting real thin.

Takeaway → mass participation ≠ successful league

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The UFL merger happened, and it didn’t matter.

2026 regular season attendance averaged 10.5k, down 20% YoY after a 5% drop in 2025. The 2026 championship game drew 988k viewers, flat with 2025 and down from 1.6M in 2024.

Multiple teams have had to shut their doors or relocate. Memphis, Michigan and San Antonio were out for 2026. Columbus, Louisville and Orlando came in, all three moving into soccer-specific stadiums rather than cavernous NFL-scale venues, and the two-conference format collapsed into a single eight-team table.

The NFL will continue to see spring football as a feeder league it can pull a few bubble players from, but America has not built up the habit of watching football in the spring.

Football is a fall game. Reversing that fact in the psyche of Americans will always be an uphill climb.

Not to mention that the NCAA ate the talent pipeline.

The developmental logic of spring football was that it would become the #2 destination for players who could not hold an NFL roster spot. Many of those players were guys like me, 1-3 years out of college.

Then NIL, revenue share and an eligibility landscape now being redrawn in federal court turned college football into a place where athletes can stay for a 5th and 6th year, earn real cash, and simultaneously improve their odds of making the NFL, bypassing the spring football pipeline altogether.

Takeaway → the popularity of a sport does not always transfer to a new format

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Big oof.

Regional eSports franchises is literally a horrible idea.

The Overwatch League, whose $20M franchise slots I cited as proof the model was working, was shut down by Blizzard at the end of 2023, inside of three months of my writing that sentence.

Two months later Blizzard handed the sport to Saudi Arabia's eSports organization, and the center of gravity is now the eSports World Cup.

The franchise model in eSports was a spectacular failure, and it failed for a reason that should have been obvious to me: geography is meaningless in a sport played over the internet by an audience organized entirely around individual creators.

What survived is the layer I completely ignored: the talent and infrastructure.

The audience is real and enormous; it just lives on YouTube/Twitch and belongs to the creators, not the leagues.

Capital that went into the representation, tooling, or distribution companies rode the eSports wave much longer than capital that bought a franchise.

Gaming should live on YouTube and stay in the hands of the creators. If I want exposure to it, I would rather own the agency business every single time.

Takeaway → think about more of the ecosystem than franchises/leagues

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Who let me think this?

The MLR never raised the $100M, and from its peak of 13 teams in 2022, the league is down to six for 2026. Club after club was unable to operate in a sustainably profitable manner.

The 2031 Rugby World Cup is on American soil and will help the popularity of the sport, but it is five years out and there is no guarantee it translates into MLR success.

Rugby has flat out struggled to commercialize the way you would think it could, given a global fanbase World Rugby puts around 800 million:

Takeaway → the obvious deals are probably harder to execute than you think

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I never expected the irrationality of all irrationalities to bull-in-a-china-shop the balance of sport.

The NCAA's NIL mania has flipped everything on its head, negating my thesis around the rise of feeder leagues and rewriting the calculus for every player entering the professional ranks.

The 2023 draft turned out to be the high-water mark, the G League Ignite and Overtime Elite both shut down or pivoted, and college became the highest-paying developmental league in the country.

Funny how a 100+ year-old institution turned out to be one of the most disruptive forces at play in the American sports landscape.

I remember hearing about the FBI raiding 26-year-old Shayne Coplan's apartment days after the 2024 presidential election and thinking, "who is Polymarket and what is the big deal?"

Little did I know that DraftKings, FanDuel, BetMGM and the rest of the sportsbooks were just the tip of the betting iceberg.

Kalshi, Polymarket and Novig were the triple AAA-bomb. They have completely pulverized the landscape as we knew it, and everyone is walking around with the radiation poisoning.

Charlie Baker has petitioned the CFTC twice for tighter rules and the NCAA now "vehemently opposes" Kalshi listing markets on the transfer portal. Adam Silver has said the NBA will treat prediction markets like gambling and is backing a federal sports betting czar.

Meanwhile, everyone else lined their pockets.

LeBron left DraftKings for Polymarket. Giannis took an equity stake in Kalshi and then starred in their NBA Finals campaign. The NHL signed landmark partnerships with both Kalshi and Polymarket, and MLB made Polymarket its exclusive prediction-market partner, as both platforms more than doubled their valuations past $20B.

The AGA projects $29.5B in legal NFL wagering at state-regulated sportsbooks for the 2026 season, flat YoY. RotoWire projects NFL trading volume on prediction markets will more than double to $36.8B, blowing past its own $32.3B estimate for sportsbooks.

Sports account for roughly 80% of Kalshi's total volume, and an estimated $5.1B of it came from 18 to 20 year olds.

I got the idea right (sports betting) and the mechanism completely wrong.

As Apollo, Ares and RedBird would all attest, it is private credit, not equity, that provides the best risk-adjusted returns in sports investing.

Private credit satisfies an investor's appetite for downside protection through a contracted return, while simultaneously enabling flexible and bespoke capital solutions by tying the underwrite to specific revenue streams.

Blue-chip sports media rights have been repriced upward for decades at double-digit CAGRs, and stadiums offer deep wells of ticketing, sponsorship, hospitality, parking and concessions revenue that can pay back a facility funding upfront renovations over a defined period.

RedBird is applying the instrument to collegiate athletics. Its Collegiate Athletic Solutions vehicle struck the first league-wide private capital deal in college sports with the Big 12: a conference-level infusion starting at $12.5M at a fixed rate over five years, plus an opt-in credit facility of $30M per school at 10%, repaid out of future conference distributions, with RedBird collecting a $1.25M annual retainer.

Pau Gasol's €55M, 25-year deal with Liga F and Apollo Sports Capital's $2.6B capital injection into Yankee Global Enterprises are two of my favorite examples of just how creative this instrument can get.

Ari Emanuel's articulation of the "anti-AI bet" broke the internet and has become table stakes vernacular across the industry writ large.

Gary Vee calls it the rise of analog, and you'll hear phrases like "scarce assets" thrown around, but the argument goes something like this:

As AI scales and automates more facets of the global economy, the relative scarcity and value of assets rooted in identity, community, and authentic human connection will disproportionally increase.

Functional tasks will be commoditized, but the assets that create meaning and facilitate collective participation will not.

Cultural IP, live experiences, and the institutions that gather people around shared identity are structurally irreplaceable.

But beyond the brilliance and simplicity of this thesis, what I have found to be the most fascinating is the way that it actually manifest itself structurally in real live event HoldCo. platforms.

This will certainly be its own full 🧭 At the Center post soon, but companies like MARI, HYROX, Liberty Media, Teton Ridge, Natural Selection Tour, Intersport, and Milky Way Park are some of my favorite companies, period.

Speaking of Milky Way Park, as the K-shaped economy continues to accelerate and the largest wealth creation event in history mints a new class of nine-figure net worths out of the mega-cap AI complex, selling ultra-luxury IRL sporting experiences has never been easier.

Companies like ALUM are bringing luxury condos and membership clubs to college towns across the country, while Real SLX builds the white-glove VIP layer so that their ultra-high-net-worth clients have something to do after they fly private to the Super Bowl.

Versions of this idea reach us commoners as well, just look at the success of Cosm and the Sphere.

MrBeast proved you could build a media empire to sell chocolate bars, so institutional capital found Good Good Golf ($45M) and Dude Perfect ($100M) and decided to run the same playbook with a sports twist.

Substack and Beehiiv grew to equip creators with every tool they might need to put out quality niche content, and the cost of creating and distributing that content fell officially to zero (or close enough to it).

Once advertising dollars shifted from traditional media toward new media creators, Source Media Group realized it could position itself at the center of multiple mega-trends and build a unified ad network for YouTube golf, launching with Bryson DeChambeau and Grant Horvat. Brilliant.

As for content-to-commerce flywheels, I make two distinctions:

(1) Content-to-audience.

The model most people default to. Create quality content, build a large following, and sell directly into that audience through apparel, CPG, live events, and more.

Ex: Dude Perfect, Good Good Golf, MeatEater, and Mr. Beast

(2) Content-to-access.

The “commerce” here is the asymmetric access, deal flow, and advisory work that comes from producing the kind of content that niche, high-intent, and highly engaged B2B audiences want.

Ex: Acquired, TBPN, All-In, Molly O’Shea, and The Joe Pomp Show.

But can run a sponsorship playbook, but the CPM logic is not the same.

Not all eyeballs are created equal, and the recent wave of new media acquisitions (Open AI / TBPN) signals a growing desire by both VCs and category leaders to own the practitioner conversation layer itself.

AKA, sports business is becoming it’s own highly valuable new media niche.

We used to raise 10-year, closed-end (with two +1 extensions), 2/20 management fee and carry on a blind pool of committed capital funds. That type of fund is dead.

The death is in two directions at once:

(1) Permanent capital.

Continuation funds, long-dated (15 to 30 year) vehicles and investment HoldCo. models took sports investing by storm once everyone realized that sports as an asset class necessitates permanent capital.

These are intergenerational assets and cultural IP. Media rights get repriced every ~10 years, and the real estate underneath them is a real, cash-flowing, permanent asset. Jerry Jones made billions by holding the Cowboys for 35+ years, and funds should look to do the same.

10-year funds are having liquidity problems because their only exit comes in the form of secondaries, limiting their ability to deliver DPI, which is why we have begun to see in-house capital markets groups stood up inside firms like Arctos.

(2) Independent sponsors.

Sports is hot, and there has been a flooding of the zone by people who want in. Not everyone can raise large swathes of capital, but many can raise smaller amounts for specific deals.

Deal-by-deal SPVs are commonplace, but the reality is that 2/20 structures are becoming harder to justify.

Compensation is of course to be expected in order to manage the SPV. But LPs are beginning to go direct into these deals, so absent a true and unique level of access, control or value-add that warrants higher compensation, 1/10 or a management fee that steps down as capital is returned are the clear routes forward.

At the end of revisiting and grading my original Evolution whitepaper, I flipped to a blank sheet of paper and wrote down every single trend, theme, and pattern that I could think while the juices were flowing.

I am certainly missing some, but based off of all of my observations, writings, discussions with industry leaders, podcasts, analysis of mega-trends, and diligence on specific sports, media, and entertainment investments/M&A deals . . .

These are the bullet points of what I believe are the key takeaways for the continual evolution of sports as an asset class.

This list is not exhaustive, but let me put you on game:

This concludes my four-part essay series on the Evolution of sports as an asset class.

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