The Deal with Alex Rodriguez and Jason Kelly

In this episode of The Deal, Monarch Collective's Jasmine Robinson tells Alex Rodriguez and Jason Kelly about the business case for investing in women's sports leagues. Jasmine explains how her $150 million fund decided to invest in the NWSL and how she sees future growth opportunities for women's sports.

(Corrects to remove reference to the WNBA in first paragraph.)

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In this episode of The Deal, The Chernin Group's Jesse Jacobs tells Alex Rodriguez and Jason Kelly about a few of his notable deals, including Barstool Sports, the Professional Lacrosse League and his recent venture in Unrivaled Sports alongside Josh Harris and David Blitzer. Jesse shares his unique approach to business, the impact of digital media on sports and his thoughts on the evolving landscape of college and youth sports markets.

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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.

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In this episode of The Deal, Jessica Gelman, chief executive of Kraft Analytics Group, tells Alex Rodriguez and Jason Kelly how she navigates the intersection of business and sports with a special focus on the transformative impact of data analytics. Alex and Jason also discuss Willie Mays' legacy and the lessons they learned from Reggie Jackson at a celebration of the Negro League.

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With all the money pouring into sports these days, big-time investor Marc Lore says he has an additional metric for success: happiness. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, Lore lays out his thinking on some of his deals, including a few with Rodriguez. 

Lore and Rodriguez initially tried to buy the New York Mets, a race they ultimately lost to billionaire hedge fund manager Steven Cohen. Then came the Minnesota Timberwolves and Lynx, and the pair jumped. There’s currently a lot of happiness in Minnesota about the Timberwolves’ performance, given their initial success in the NBA playoffs.

The 52-year-old Lore made his fortune as an entrepreneur through a series of startups, including Diapers.com and Jet.com, which he and his partners sold to Amazon and Walmart, respectively. Those experiences pushed him toward a near-obsession with company culture and mission. He’s created a framework he dubs VCP—which stands for “vision, capital and people.”

The capital in Lore’s equation has come quickly and seemingly easily. Diapers was sold to Amazon for more than $500 million and Jet.com was acquired by Walmart for about $3.3 billion. Yet, Lore insists the drive was about more than the cash, a lesson he learned with the Diapers deal.

“After the money was wired to our bank account, we sort of said, ‘We should be celebrating right now,’” Lore says. “And we’re like, depressed. And it just goes to show you, it wasn’t about the money. Like the mission that we had set out was kind of crushed with the sale to Amazon.”

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Stephen A. Smith says he’s always been ambitious, but nothing fueled a burning drive to succeed like being fired from ESPN. His exit from the sports network in 2009 radically changed how he felt about himself, Smith says—and how he wanted to make a living.

After ESPN and Smith parted ways, he began the long road back, starting on radio and leveraging his experience as a print journalist to develop sharp points of view. He eventually built a following whose size effectively made his return to TV inevitable. 

After resuming his position in front of the camera, Smith quickly helped remake the modern sports media landscape. Now 56, he’s widely credited (or derided) for the “hot take” version of sportscasting that now dominates ESPN, Fox Sports and social media. It’s literally in the name of his flagship ESPN morning show, “First Take,” which he initially popularized with Skip Bayless. It now features Smith with a rotating cast of sparring partners, as well as moderator Molly Qerim. 

Yet Smith has constantly stretched himself beyond ESPN—and sports—most notably through his podcast, The Stephen A. Smith Show, which he created and runs through his own production company. With more than 600,000 subscribers to its YouTube feed alone, Smith says he’s more convinced of his ability to flex that popularity for another record contract with ESPN (his current deal is up next year).

You can also watch The Deal on Bloomberg Originals, YouTube or Bloomberg TV.

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Serena Williams revolutionized tennis—that much is unquestioned. With her sister and fellow superstar Venus beside her and father Richard behind them both, Williams went on to transform the way the world looks at tennis stars. Having now put her racket down, she has moved on to the world of finance and started her own venture capital firm, Serena Ventures. But this time, she’s doing it all on her own. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, Williams explains just how these early financial lessons formed the basis of success in her second act.

In tennis, Williams is widely regarded as the greatest of all time. In business, she exudes similar ambition for her growing business empire. Williams says she’s built a team that she trusts while staying intimately involved with every major decision. Diving into the details is something she’s known for—Williams was literally at the table for her first big shoe endorsement deal, with Puma.

Serena Ventures has invested in more than 20 companies in its first fund, and that’s in addition to the dozens of angel investments Williams has made. She’s also focused much of the firm’s energy on investing in companies run by traditionally underrepresented founders, especially women and people of color. (Only 2% of venture capital goes to companies led solely by women, while just 1% goes to firms with Black founders.)

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Mark Shapiro has a habit of making the unlikely happen. From marrying Ultimate Fighting Championship with World Wrestling Entertainment to making the call to hire Stephen A. Smith at ESPN, Shapiro finds a way to get deals done. Now, as president and COO of Endeavor and TKO—the publicly traded combination of WWE and UFC—he and Ari Emanuel are reshaping sports, media and entertainment. On the latest episode of The Deal with Alex Rodriguez and Jason Kelly, Shapiro reveals their guiding principle: Even in the most turbulent of media worlds, people love to watch games.

Shapiro made his name as the brash young head of programming at ESPN, greenlighting some of its most iconic programs, including Pardon the Interruption, the long-running talk and debate show hosted by Tony Kornheiser and Michael Wilbon. It was also Shapiro who overruled his direct reports by bringing in Stephen A. Smith for an audition, a decision that catapulted Smith to the very top of the sports media pyramid and redefined the medium around hot takes. (Smith is a guest on an upcoming episode of The Deal).

The pair work together still, with Smith now represented by Endeavor’s talent arm. Shapiro and his partner Emanuel (made famous by the fictional Ari Gold on Entourage) have built Endeavor into a multifaceted entertainment company heavily invested in sports. Its biggest deal was creating TKO, which went public last fall and now has a market capitalization of $16 billion.

Amid all the dealmaking, Shapiro—who in between ESPN and Endeavor ran Six Flags—says he’s focused on creating situations where talent inside his shop and out can keep moving forward.

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Future Hall of Fame wide receiver Larry Fitzgerald said he always expected to be coached. Just not by a Wall Street banker. So when Frank Bisignano—then a senior JPMorgan Chase & Co. executive and now CEO of Fiserv—pushed a twentysomething Fitzgerald to think about life beyond the National Football League, it changed his trajectory.

That led to a series of internships between football seasons, touching on everything from venture capital to real estate and mezzanine financing. Fitzgerald played football for more than a decade after his run-in with Bisignano, spending his entire pro career with the Arizona Cardinals. But thanks in part to that first internship (at JPMorgan), he’s since invested in more than 160 companies, ranging from tech firms to an Indian cricket team. One of his breakthrough business moments came in 2020, when he joined the board of Dick’s Sporting Goods Inc., a publicly traded retailer that now has a market capitalization of about $16 billion.

Arguably among Fitzgerald’s most interesting deals is one tied to his oldest passion: chess. He started playing as a kid, an effort by his parents to focus a restless young mind. His public affinity for the game led to a meeting with Danny Rensch, the “chief chess officer” of Chess.com. Fitzgerald invested in the company and played in a celebrity tournament. He even allowed Chess.com to create a bot trained on his previous matches.

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Twenty-five years later than expected and following several false starts, women’s professional soccer looks to finally be planting long-term roots. And at the center of it all is one of the icons of a US championship team.

Brandi Chastain, whose electrifying penalty kick in front of more than 90,000 screaming fans at the Rose Bowl sealed the 1999 Women’s World Cup, is a co-owner of Bay FC, the latest franchise to join the fast-growing National Women’s Soccer League (NWSL). So what’s the difference with this league, this time, after two earlier failures? Solid investment for the long haul. 

The moment seems to have arrived for women’s soccer, as it has for the broader profile of women in American sports. Bay FC was taking the field this spring just as the women’s edition of NCAA March Madness kept breaking its own records, driven by outsized performances and personalities like Caitlin Clark and Angel Reese. This new era of attention and support for women’s sports hasn’t seen its equal since Chastain’s famous, jersey-shedding celebration of her World Cup victory. That team—and its successors—produced stars that broke through into the broader public consciousness: Carli Lloyd, Alex Morgan and Megan Rapinoe among them.

But all that excitement needed money to sustain it. These days, Chastain has linked up with Sixth Street Partners, a global investment firm that’s developed a business case for women’s sports. 

Now, Chastain says, it’s up to her and her fellow owners to leverage not just the money, but the expertise. That means blending her experience as a World Cup winner, Olympic gold medalist and coach with the analytics generated across reams of Sixth Street spreadsheets to produce a winning team.

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