The Sports Advisors podcast is a biweekly roundtable discussion for decision-makers, hosted by their peers, on the stories that actually matter and their second-order effects. It is actionable intelligence from senior operators who have actually built, bought, sold, programmed, monetized, and scaled sports businesses.

In the latest episode, The Sports Advisors talk challenger leagues as investments. The Professional Women’s Hockey League announced its first outside investment, a reported $100 million buy-in from Larry Tanenbaum’s Kilmer Sports Ventures and Ilitch Companies in June. The Premier Lacrosse League also recently closed on a $100 million Series E financing round led by Ares funds and Brooklyn Nets owner Joe Tsai.

We discuss the markers of long-term viability, what institutional capital wants to underwrite, where liquidity could come from, and which properties appear best positioned to scale.

The cast for the fifth episode in a row includes:

As always, you can connect with a member of the JohnWallStreet Advisory team by sending a note to [email protected]. In fact, we encourage it!

Key insights and takeaways from the 50-minute conversation:

Predicting Long-Term Viability

The investment case around sports properties is often reduced to media rights upside. But sophisticated investors buying into challenger leagues start by identifying signals that suggest the property will endure.

So, what are the strongest predictors?

“It's where the youth market is going. Youth equals participation. Participation equals family. Family equals decision-maker and where [it is going to spend their] disposable income,” Brody said. “Data [is another], and I also hear a lot about how technology [can be integrated] into [a given] entertainment platform from the investment community.”

The Institutional Pitch 

Early money in challenger leagues is often passion-led. But as properties mature and begin to seek institutional capital, the pitch must evolve into a legitimate investment case.

“Many founders are wrapped [up] around [the idea that their sport] is ‘the next NFL’. I tell them to never [make] that [comparison] again,” Crakes said. “What you want to do is [convey the property has] a market that is underserved, it's complementary to these larger trends [like the experiential economy, the changes in viewing habits, and rise of discovery platforms that have made live sports more valuable], so that an investor [can take] a portfolio approach.” 

Paths to Liquidity

One of the most-asked questions about league-level investments is how investors will gain liquidity. As challenger league properties develop, those showing signs of long-term viability should begin to see several potential exit paths emerge.

“There's the typical pass it on to the next PE firm. There's [leagues], like the PWHL [and PLL, that] as they scale [will] set themselves up to then go look at local owners for the single teams,” Shah said. “And then there could also be a roll-up. We saw the PLL already did a merger with their competitor [Major League Lacrosse]. So, there's at least three realistic scenarios that could happen in a pretty short time horizon. For [savvy well-connected investors, like] Tanenbaum and Ilitch, [these are opportunities to] get in early, provide the access [needed to create upside], make the impact, and then also potentially have an exit if [they] wish.”

Picking the Winners

We wrapped the episode by asking each of the Advisors to select one challenger property they would invest in and explain why. Their answers offered a window into how smart money is evaluating a crowded landscape of leagues still trying to establish their footing. 

“I'm a huge fan of what Athletes Unlimited is doing with softball. [Just look at] the ratings for women's college softball,” Kelly said. “[But] they could do a little bit of a better job promoting the fact that they're THE pro softball league. This isn't the WNBA [or] the women's version of X. [AUSL is] it. Softball is a women's sport. So, domestically [there] is such a big opportunity for [that league].” 

We agree, which helps to explain why JaneWallStreet is hosting At The Table Live, a breakfast and intimate conversation with AUSL Commissioner Kim Ng (along with Jomboy Media CEO Courtney Hirsch), on July 13 in Philadelphia. The discussion will center on the strategic value of league relationships. You can request a seat here. 

📺 Watch the full episode on JohnWallStreet’s YouTube page.
🎧 Listen or watch on Spotify.

Catch previous episodes of The Sports Advisors on JohnWallStreet’s YouTube channel, including discussions on the Saudi Public Investment Fund’s decision to stop funding LIV Golf after the 2026 season, speculation around Vancouver Whitecaps FC potentially relocating to Las Vegas, the 2026 World Cup serving as a stress test for the modern sports business model, and a much-needed sports betting reality check.

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The next episode of The Sports Advisors will be released on Wednesday, July 15.