Saquon Barkley told Front Office Sports this week that he had to sell his stake in Polymarket. NFL rules bar players from investing in or endorsing sportsbooks and prediction markets, and the league counts prediction markets as gambling. "I was in it before, but no bueno," Barkley said.

In September 2025, Polina Pompliano's The Profile listed Polymarket among Barkley's private investments, alongside Anthropic, Anduril, Ramp, Cognition and Neuralink. He usually writes checks of $250,000 to $500,000 into companies that have already shown growth, and he is a limited partner in Founders Fund and Thrive Capital.

Barkley said the NFL briefs players before every season on new endorsement and investment rules, and he invested before the league barred prediction markets. The NFL confirmed the ban on Wednesday but wouldn't comment on his case. In January, the NFLPA said players can't endorse or act as brand ambassadors for Kalshi or Polymarket. The league's betting partners are DraftKings, FanDuel and Fanatics, and it has asked the Supreme Court to treat sports event contracts as state-regulated gambling.

The NBA went the other way this week, naming Kalshi and Polymarket its preferred prediction market partners. NBA players can endorse prediction markets and hold up to 1% of a gambling or prediction market company, but they can't promote or trade NBA event contracts. LeBron James's Polymarket deal reportedly pays him $15M a year, almost 4 times his $3.9M salary with the 76ers, meanwhile Giannis Antetokounmpo is an investor in Kalshi.

The NHL, MLB and MLS also have prediction market deals, and FOS reported MLB's exclusive Polymarket deal could be worth up to $300M over four years. That leaves the NFL as the only major US league without one. Retired players aren't covered by the rule: Marshawn Lynch and Richard Sherman invested in Kalshi in April through Factory Holdings, a family office platform.

For athletes building portfolios, the league's investment policy decides what they can keep. Barkley bought into Polymarket under one set of rules and was forced to sell under the next.

The Deal: In November 2025, Upside, the cash-back app for gas, groceries and restaurants, launched an Ambassador program through NIL Club. NIL Club activated 12,668 athletes, and each one got a personal referral link to share with teammates, roommates and family.

The Spend: Upside and NIL Club have not disclosed the program's budget or what ambassadors earn per referral, however…

The Result: Ambassadors referred 5,323 people, with 1,884 of them signing up, a 35.4% conversion rate. 596 made a verified purchase, which is 31.6% of sign-ups. The first purchases came in January 2026, and the program is still running. NIL Club reports these figures from Upside's referral tracking; they are platform-reported and not independently audited.

Why It Worked: The link went to people who already trust the athlete. Upside is also an easy product to recommend to this group, and NIL Club notes that athletes drive constantly, to practice, games and around campus. The program worked through volume: 12,668 ambassadors produced about 42 referrals per 100 athletes. NIL Club also reports a separate Upside campaign that turned 3,000 clicks into 1,500 verified users, a 50% click-to-signup rate.

via NIL Club, Upside

Peak Saunas, founded by Austin Laudenslager, sells full-spectrum infrared saunas for the home. They sell only through their own site, and every model ships with a red light therapy panel, a lifetime warranty, and free lifetime access to the Peak Wellness Club, a guided app with daily sessions and 30-day programs.

Peak says it now has more than 10,000 sauna owners and monthly revenue went from $330,000 to $1.12 million in 6 months after it brought in OPTYO to run its performance marketing, rebuild its website, and produce content in-house.

If you are a founder building in sports, tech, or wellness, OPTYO helps sports, fitness, and wellness brands grow their online presence by improving how they market and reach customers. Reply to this email and we can connect you with Andre.

Jordan Clarkson is a 13-year NBA vet and 2026 champion in his 2nd with the New York Knicks. He was the 46th overall pick in 2014, won Sixth Man of the Year in 2021, and became the first Filipino-American to win an NBA title this summer. He re-signed with New York on a 1-year, $3.9M deal. He also holds Filipino citizenship, plays for Gilas Pilipinas, and has a large following in the Philippines.

Off the court, Clarkson is an early investor in Barcode, the plant-based performance drink co-founded by Kyle Kuzma, alongside Carmelo Anthony and Victor Wembanyama. Axum Capital Partners agreed to buy a controlling interest in the brand this August.

He has a long-term partnership with Lululemon, has worked with Aldo and Camp High, and teamed with KidSuper on a custom suit and sneaker for Paris Fashion Week as part of a Meta campaign. He is also building his own label, Seventy-Eight Studios, starting with pop-ups and essentials.

Next up, he wants partnerships where he has creative input, with brands he can actually wear and make an impact. Connect with Jordan and his team here!