In this episode of The Deal, entrepreneur Joe Pompliano tells hosts Alex Rodriguez and Jason Kelly about his rise in the sports media landscape, potential directions for sports valuations and future trends in sports media.

In this episode of The Deal, entrepreneur Joe Pompliano tells hosts Alex Rodriguez and Jason Kelly about his rise in the sports media landscape, potential directions for sports valuations and future trends in sports media.

When sports, business and culture collide, there’s often a deal to be made. Join Alex Rodriguez and Bloomberg correspondent Jason Kelly as they get the inside track from corporate titans, sports champions and game-changing entrepreneurs on investing, strategy, reinvention and the ones that got away. The Deal is a Bloomberg Podcasts and Bloomberg Originals series that’s passionate, relaxed, insightful and inspirational. If you think you know these icons, prepare to be surprised.

Hosts:

Alex Rodriguez is chairman and chief executive of A-Rod Corp, an investment firm that backs startups and partners with global companies across real estate, sports and entertainment. While best known as a fourteen-time All-Star and World Series champion with the New York Yankees, Rodriguez is now an owner of the Minnesota Timberwolves and Minnesota Lynx sports teams and an on-air analyst for Major League Baseball.

Jason Kelly is the chief correspondent of Bloomberg Originals. During his two decades at Bloomberg, Kelly has served as executive editor of Bloomberg Television, hosted Bloomberg Businessweek on television and radio, and also hosted Power Players and Next in Sports series. He’s also the author of two books, The New Tycoons, about the global private equity industry, and Sweat Equity, an inside look at the business of fitness.

When sports, business and culture collide, there’s often a deal to be made. Join Alex Rodriguez and Bloomberg correspondent Jason Kelly as they get the inside track from corporate titans, sports champions and game-changing entrepreneurs on investing, strategy, reinvention and the ones that got away. The Deal is a Bloomberg Podcasts and Bloomberg Originals series that’s passionate, relaxed, insightful and inspirational. If you think you know these icons, prepare to be surprised.
Hosts:
Alex Rodriguez is chairman and chief executive of A-Rod Corp, an investment firm that backs startups and partners with global companies across real estate, sports and entertainment. While best known as a fourteen-time All-Star and World Series champion with the New York Yankees, Rodriguez is now an owner of the Minnesota Timberwolves and Minnesota Lynx sports teams and an on-air analyst for Major League Baseball.
Jason Kelly is the chief correspondent of Bloomberg Originals. During his two decades at Bloomberg, Kelly has served as executive editor of Bloomberg Television, hosted Bloomberg Businessweek on television and radio, and also hosted Power Players and Next in Sports series. He’s also the author of two books, The New Tycoons, about the global private equity industry, and Sweat Equity, an inside look at the business of fitness.

The Deal with Alex Rodriguez and Jason Kelly

Inside Joe Pompliano's Sports Media Playbook

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/63124303-a00a-4016-9046-b1a2011180c5/transcript

Jess Pegula has spent her life around elite sports — both as one of the best tennis players in the world and as part of the family behind the Buffalo Bills and Buffalo Sabres. Beyond competing at the highest level, she’s become an influential voice in the future of professional tennis through her role as a player representative for the Women’s Tennis Association, giving her a rare window into both the business and competitive sides of the industry.

In this episode of The Deal, Alex Rodriguez and Jason Kelly sit down with Jess to talk about lobbying for change in professional tennis, balancing the interests of players and management, and what she’s learned from growing up around major sports franchises. Jess shares lessons from her parents Terry and Kim Pegula on leadership, team building and adapting to different personalities. She also discusses the unique culture of Buffalo sports and how her experiences in tennis and sports ownership have shaped the way she approaches business and competition.

You can also watch this interview on YouTube.

Jess Pegula has spent her life around elite sports &mdash; both as one of the best tennis players in the world and as part of the family behind the Buffalo Bills and Buffalo Sabres. Beyond competing at the highest level, she&rsquo;s become an influential voice in the future of professional tennis through her role as a player representative for the Women&rsquo;s Tennis Association, giving her a rare window into both the business and competitive sides of the industry.
In this episode of The Deal, Alex Rodriguez and Jason Kelly sit down with Jess to talk about lobbying for change in professional tennis, balancing the interests of players and management, and what she&rsquo;s learned from growing up around major sports franchises. Jess shares lessons from her parents Terry and Kim Pegula on leadership, team building and adapting to different personalities. She also discusses the unique culture of Buffalo sports and how her experiences in tennis and sports ownership have shaped the way she approaches business and competition.
You can also watch this interview on<a href="https://www.youtube.com/show/VLPLqq4LnWs3olXQamF7u9PM3_Q1RhkUBIZu?sbp=KgtKUm1lcVBRLWpSa0AB"> YouTube</a>.

Jess Pegula on the Business of Tennis

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/0ca18986-c05e-46c5-b6b8-b45000e7982e/transcript

Alan Waxman’s Sixth Street Partners has a deep conviction in sports. Over the past five years, Alan and his firm have taken a minority stake in teams in most major professional leagues, including: the Boston Celtics, the San Antonio Spurs, the San Francisco Giants and FC Barcelona. In 2024, Sixth Street became the first investment fund to take a controlling interest in an American pro team with the NWSL’s Bay FC. And as of September 2025, Sixth Street owns a 3% stake in one of the biggest names in sports- the New England Patriots.

In this episode of The Deal, Alex and Jason sit down with Alan live at Bloomberg Invest. Alan tells the story of getting the call from Robert Kraft and why Sixth Street is one of only a handful of PE firms approved to invest in the NFL. He also shares his view on international growth opportunities in the NBA, why a historic NWSL expansion fee paid off and how far away we are from institutional capital taking a controlling stake in an NFL or NBA team. Finally, Alex and Alan give their takes on how to “fix” professional baseball.

You can also watch this interview on YouTube.

Alan Waxman&rsquo;s Sixth Street Partners has a deep conviction in sports. Over the past five years, Alan and his firm have taken a minority stake in teams in most major professional leagues, including: the Boston Celtics, the San Antonio Spurs, the San Francisco Giants and FC Barcelona. In 2024, Sixth Street became the first investment fund to take a controlling interest in an American pro team with the NWSL&rsquo;s Bay FC. And as of September 2025, Sixth Street owns a 3% stake in one of the biggest names in sports- the New England Patriots.
In this episode of The Deal, Alex and Jason sit down with Alan live at Bloomberg Invest. Alan tells the story of getting the call from Robert Kraft and why Sixth Street is one of only a handful of PE firms approved to invest in the NFL. He also shares his view on international growth opportunities in the NBA, why a historic NWSL expansion fee paid off and how far away we are from institutional capital taking a controlling stake in an NFL or NBA team. Finally, Alex and Alan give their takes on how to &ldquo;fix&rdquo; professional baseball.
You can also watch this interview on <a href="https://www.youtube.com/show/VLPLqq4LnWs3olXQamF7u9PM3_Q1RhkUBIZu?sbp=KgtKUm1lcVBRLWpSa0AB">YouTube</a>.

Alan Waxman is a Sports Superinvestor

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/128021d1-cb5b-4c8d-b6a6-b44901158ce1/transcript

Baseball and softball are both having a moment. The 2025 Women’s College World Series was the most watched ever, with 2.4 million people tuning in to game 3. On the baseball side, almost 11 million people watched Venezuela beat the U.S. to take the 2026 World Baseball Classic title. The audience for both sports is growing, and LSU softball star and baseball media analyst AJ Andrews is one of their most enthusiastic ambassadors.

In this episode of The Deal, Alex Rodriguez and Jason Kelly talk to AJ about how the MLB must embrace player authenticity in order to flourish. She also shares how a conversation with ESPN’s Jessica Mendoza changed her career trajectory and why the future of softball lies in storytelling. Finally, AJ and Alex compare notes about the benefits of being an athlete turned broadcaster.

 

Baseball and softball are both having a moment. The 2025 Women&rsquo;s College World Series was the most watched ever, with 2.4 million people tuning in to game 3. On the baseball side, almost 11 million people watched Venezuela beat the U.S. to take the 2026 World Baseball Classic title. The audience for both sports is growing, and LSU softball star and baseball media analyst AJ Andrews is one of their most enthusiastic ambassadors.
In this episode of&nbsp;The Deal, Alex Rodriguez and Jason Kelly talk to AJ about how the MLB must embrace player authenticity in order to flourish. She also shares how a conversation with ESPN&rsquo;s Jessica Mendoza changed her career trajectory and why the future of softball lies in storytelling. Finally, AJ and Alex compare notes about the benefits of being an athlete turned broadcaster.
&nbsp;

AJ Andrews on What's Next for Baseball and Softball

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/b0963dcf-1342-44d2-ab38-b4420110d995/transcript

Inside Joe Pompliano's Sports Media Playbook

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