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).

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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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