🔊 Inside DraftKings’ $250 Million Bet On The Future

This week, news broke that DraftKings, a leading daily fantasy sports and sports betting platform, is acquiring predictions platform Railbird as it prepares to launch a mobile platform called DraftKings Predictions in the coming months.

DraftKings Predictions will allow customers to trade regulated event contracts on real-world outcomes across finance, culture, and entertainment.

According to FOS, DraftKings will pay up to $250 million for the total acquisition of the platform. They will pay $50 million upfront, with an additional $200 million in performance incentives, although the specifics of these incentives are unclear.

Why Does This Matter?

Unless you've been completely off the grid, you've heard about the boom in prediction markets.

These exchanges let users bet on everything from political elections to sports games and crypto prices.

Right now, the space is dominated by two players: Kalshi and Polymarket.

Earlier this month, Kalshi raised $300 million at a $5 billion valuation.

On the other hand, Polymarket is closing a $2 billion investment from the New York Stock Exchange operator.

These two companies, both now worth billions, are dominating a space that barely registered on most people’s radars a year ago.

But the regulatory issues are messy.

Kalshi is fighting multiple court battles over “illegal sports offerings,” and Polymarket is only now planning to reopen to US users, nearly four years after being effectively banned by the Commodity Futures Trading Commission (CFTC).

So, how does all of this impact DraftKings and most importantly all sports betting platforms?

Well, despite the legal hurdles, the prediction market's competitive threat is real and isn’t going away.

DraftKings and Flutter shares plunged more than 10% after Kalshi launched customizable parlays, one of the key differentiators that traditional sportsbooks had maintained.

Prediction markets also operate on thin fees of 1–2% versus sportsbooks' 8–10% vig.

Not to mention, they're available in all 50 states, including locked-out markets for sportsbooks like California and Texas.

DraftKings and others can't fight the market.

They have to join it, which is exactly what this acquisition represents.

Traditional sportsbooks still have advantages at the moment such as massive scale, established state licenses, and deep partnerships with leagues and media.

But prediction markets are quickly forcing rapid adaptation into new products and pricing models.

Now, the question isn't whether prediction markets will replace DraftKings and other sportsbooks.

It's how quickly will sportsbooks evolve before market share starts to fade.

• CR Fitness Holdings Secures $350M. CR Fitness Holdings, the holding company for Crunch Fitness franchises, has raised a $350 million strategic investment from global investment firm Sixth Street as the group looks to add more than 100 clubs over the next five years. CR Fitness currently operates nearly 90 clubs across Florida, Georgia, North Carolina, Texas, and Tennessee. North Castle Partners, which led a majority investment in 2019 and recapitalized the business in 2022, remains the largest shareholder in CR. The deal also includes a new senior debt facility provided by Golub Capital (more here).

• CourtReserve Secures $54M. CourtReserve, a leading club management software platform, announced that it has secured a $54 million strategic growth investment from Mainsail Partners, a growth equity firm investing in vertical SaaS businesses. The investment will help fuel accelerated product development, enhance customer service and support, deepen integrations, and expand the company’s market reach to sports facilities across North America. CourtReserve serves over 2,000 clubs and five million players worldwide (more here).

• Michezo Sports Raises $2.5M. Michezo Sports, a Bengaluru-based sports infrastructure startup, has raised $2.5 million in a pre-Series A funding round led by Centre Court Capital, with participation from Rainmatter, the investment arm of Zerodha. Founded in 2019, the startup offers end-to-end services like design, construction, and maintenance of sports facilities. The startup plans to expand into new areas such as swimming pools and civil sporting infrastructure while strengthening its distribution platform for sports equipment and materials (more here).

• Ilitch Sports + Entertainment Invests In TGL’s LA Golf Club. Ilitch Sports + Entertainment (IS+E), the business arm of the Detroit Red Wings, Detroit Tigers, and The District Detroit, announced it has invested in the Los Angeles Golf Club (LAGC) of TGL presented by Sofi. As part of the relationship, IS+E will serve as LAGC’s sponsorship agency of record and act as an extension of LAGC’s internal team. LAGC is owned by Alexis Ohanian (Seven Seven Six), and IS+E joins an investor group with Serena Williams, Venus Williams, the Antetokounmpo brothers, Alex Morgan, Michelle Wie West, Shonda Rhimes, and Good Good Golf (more here).

• FirstTracks Sports Ventures Invests In Austin FC. FirstTracks Sports Ventures, managed by Jon-Erik Borgen and part of the ownership group behind NWSL expansion side Denver Summit FC, has completed its investment in Austin FC at a valuation of $912 million. The Borgen family joins investors Jenny Just and Matt Hulsizer, co-founders of PEAK6 Investments, billionaire Nvidia board member Tench Coxe, Magnetar Capital managing partner Dave Snyderman, and Tanuj Gulati, co-founder and former CTO of Securonix. The stake in the team was not disclosed (more here).

• Hudl Acquires Athletic Data Innovations. Hudl, the global leader in sports performance analysis and video technology, announced the acquisition of Athletic Data Innovations (ADI), a cutting-edge athlete monitoring software platform. For over 15 years, ADI has provided advanced analytics to top-tier sports organizations globally. This strategic acquisition is Hudl’s 18th and expands its capabilities in human performance and strengthens its commitment to providing professional teams with the most sophisticated tools available. Financial details were not disclosed (more here).

• Unrivaled Sports Acquires Football 'N' America. Unrivaled Sports, the youth sports holding company founded by Josh Harris and David Blitzer, announced the acquisition of Football ‘N’ America (FNA), a flag football business cofounded by former Saints quarterback Drew Brees. Unrivaled Sports has over 20 youth sports-related companies in its portfolio. FNA marks the fourth flag football business in the portfolio, along with Under the Lights Flag Football, New England Flag Football, and All-American Flag Football. Drew Brees will remain closely involved. Financial details were not disclosed (more here).

• NHL & Kalshi Announce Partnership. The NHL, Kalshi, and Polymarket announced a new multi-year agreement, with Kalshi and Polymarket both being named as the official prediction market partners of the NHL. Kalshi and Polymarket are the fastest-growing prediction market companies in the US. The opportunity provides the two companies with access to official NHL proprietary data and rights to use NHL marks, logos, and official designations on their platforms and products. Kalshi’s and Polymarket’s brokers and merchants will also be able to use NHL marks and logos to identify the Polymarket and Kalshi products that they make available (more here).

• PIF’s SURJ Sports Investment & ATP Announce Partnership. SURJ Sports Investment, the sports investment arm of Saudi Arabia's Public Investment Fund, and ATP announced the launch of an all-new ATP Masters 1000 tournament to be hosted in Saudi Arabia. Saudi Arabia will become the tenth ATP Masters 1000 host, joining the existing nine tournaments in Indian Wells, Miami, Monte-Carlo, Madrid, Rome, Toronto/Montreal, Cincinnati, Shanghai, and Paris. The agreement marks a new era for global tennis and a major sports transformation in Saudi Arabia, bringing the most prominent names in the sport to the country. The Saudi tournament will begin as early as 2028 (more here).

• Chelsea FC & FPT Announce Partnership. Chelsea Football Club and FPT, one of the largest information technology service companies in Vietnam, announced an expansion to their existing partnership, in which the Asian Pacific technology company has been named a Principal Partner for the 2025-26 season. FPT will be represented on the sleeves of the Chelsea FC men’s, women’s, and academy kits. The two companies first joined forces earlier this year in an innovative collaboration to transform the club’s digital capabilities, enhance fan engagement, and bring fans from across the world closer to the club (more here).

• Genius Sports & Croatian Basketball Federation Announce Partnership. Genius Sports, one of the world’s leading sports tech and data companies, announced a new partnership with the Croatian Basketball Federation (CBF) to introduce advanced data and AI-driven technologies across Croatian basketball competitions. At the core of the deal is GeniusIQ, the company’s AI-powered data platform designed to capture and analyze player and ball movement using automated tracking cameras installed in arenas. Through GeniusIQ, coaches and analysts gain access to real-time data covering player speed, spacing, defensive rotations, and other key metrics. (more here).

• PGA Tour & Good Good Golf Announce Partnership. The PGA TOUR and Good Good Golf, a popular YouTube golf brand, announced a new partnership in which Good Good Golf will become the title sponsor for next year’s fall tournament. The Good Good Championship is set to be played in November of 2026 at Omni Barton Creek Resort & Spa's Fazio Canyons Course in Austin, Texas. It will be broadcast on the Golf Channel and three other properties produced by PGA TOUR Studios. The golf influencer brand, founded in 2020, recently raised $45 million in funding and has nearly 2 million YouTube subscribers and 1 million Instagram followers (more here).

• Global Payments & Harris Blitzer Sports & Entertainment Announce Partnership. Global Payments, a leading worldwide provider of payment technology and software solutions, and Harris Blitzer Sports & Entertainment (HBSE) announced a multi-year global partnership in which Global Payments will be the Official Payment Technology Provider for the Prudential Center, the New Jersey Devils, and the Philadelphia 76ers. Global Payments will integrate Genius, its point-of-sale command center for business operations, across all food and beverage locations for the Prudential Center and the Devils (more here).

• Jimmy Butler Joins San Diego Wave As A Minority Investor. Golden State Warriors Forward Jimmy Butler has officially joined the NWSL’s San Diego Wave ownership group. The club was valued at $120 million in October 2024 after the Levine Leichtman family acquired the team from Ron Burkle. Butler also joins retired San Diego Wave star Alex Morgan, who joined the ownership group in May of this year. Financial details and Butler’s equity in the team were not disclosed (more here).

• Travis Kelce Invests In Six Flags Entertainment. Super Bowl champion Travis Kelce is teaming up with Jana Partners, an activist investment firm, as well as consumer executive Glenn Murphy and technology executive Dave Habiger, to invest in Six Flags$FUN ( ▼ 8.36% ), the parent company of Cedar Point and Kings Island. The group is injecting around $200 million to acquire a 9% stake in Six Flags Entertainment. They plan to engage with the company's board to revitalize branding, improve operations, and assess leadership (more here).

• The Business Model Behind The Baller League. A new UK soccer league took social media by storm earlier this year. Still, rather than multimillion-dollar signings and giant stadiums, the Baller League’s players earn in the hundreds of dollars each game, and the entire league is played in a 6,000-capacity former handball court in East London. So how did a six-a-side league of perceived lower-league soccer players become so big that it ended up selling out London’s O2 Arena? And how much more can it grow (more here)?

• Sixth Street CEO Alan Waxman On Sports Investing & Identifying Opportunities. Sixth Street is a leading global multi-strategy private capital investment firm with over $115 billion of assets under management. Alan Waxman, Co-Founding Partner, CEO, and Co-Chief Investment Officer at Sixth Street, explains how the firm identifies opportunities across asset classes and sectors, from sports to real estate to tech, and Sixth Street's approach to investing, including its TAO strategy. He also shares takeaways from his time working at Goldman Sachs in this Talks at GS with Goldman Sachs Chairman and CEO David Solomon (more here).

This week’s guest on the Vetted Sports podcast is Matt Rizzetta.

Matt Rizzetta is Founder and Managing Partner of Underdog Global Partners, which owns, operates, and advises on assets that unlock unique experiences, provide exclusive access, and target attractive return profiles.

Rizzetta is an entrepreneur and global executive with an exemplary track record of acquiring, operating, and scaling companies across media, sports, and entertainment platforms worldwide.

In this episode, we discuss:
‣ How Matt got started investing in sports
‣ What many investors get wrong about the sports asset class
‣ Launching Underdog Global and why now was the right time to do so

Check out the full episode here: Apple | Spotify | YouTube