Are Billionaires Done Investing In AI Startups? Here’s the Surprising Thing They’re Betting On Instead.

Goldman Sachs says 25% of family offices already invest in sports. Another 25% want in. A $225 million pickleball deal explains why.

By Jonathan Small | edited by Dan Bova | Jun 08, 2026
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While AI deals dominate the headlines, the ultra-wealthy spent May betting on sports, says CNBC. Family offices made 51 direct investments last month, headlined by a $225 million investment in Pickleball Inc., the parent company of Major League Pickleball, led by Tom Dundon’s family office and Apollo.

The deals went beyond pickleball. Michael Dell acquired a 25% stake in the Las Vegas Raiders as part of a Silver Lake-led group. David Adelman‘s family office co-led a $12 million Series A for PlayerData, a UK startup making GPS-enabled smart soccer balls and vests. A Goldman Sachs survey found 25% of family offices already invest in sports and another 25% want in, drawn to the sector as an inflation hedge.

The pickleball numbers might sound surprising, but the sport now has 24 million players and has been the fastest-growing in America for five straight years. The deal values the combined entity at around $800 million. Wealthy investors have decided this is no longer tennis’s little cousin.

While AI deals dominate the headlines, the ultra-wealthy spent May betting on sports, says CNBC. Family offices made 51 direct investments last month, headlined by a $225 million investment in Pickleball Inc., the parent company of Major League Pickleball, led by Tom Dundon’s family office and Apollo.

The deals went beyond pickleball. Michael Dell acquired a 25% stake in the Las Vegas Raiders as part of a Silver Lake-led group. David Adelman‘s family office co-led a $12 million Series A for PlayerData, a UK startup making GPS-enabled smart soccer balls and vests. A Goldman Sachs survey found 25% of family offices already invest in sports and another 25% want in, drawn to the sector as an inflation hedge.

The pickleball numbers might sound surprising, but the sport now has 24 million players and has been the fastest-growing in America for five straight years. The deal values the combined entity at around $800 million. Wealthy investors have decided this is no longer tennis’s little cousin.

Jonathan Small Founder, Strike Fire Productions

Entrepreneur Staff
Jonathan Small is a bestselling author, journalist, producer, and podcast host. For 25 years, he... Read more
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