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ESPN of Pickleball: From Newsletter to Multi-Sport Media Holdco

The Story

Shields entered pickleball with an explicit positioning bet. “Once his father discovered pickleball and built a court, Shields decided to launch a pickleball business with the mission of becoming ‘the ESPN of pickleball’” (Source 3).

The positioning became self-fulfilling. “We very quickly realized there was a major appetite for pickleball news,” Shields said. “So, we launched an Instagram, jumped on Facebook, started publishing news on our blog. Before we knew it, we became this ESPN of pickleball” (Source 1).

His thesis on why the position was open: “By existing, we’re giving validity to the sport. Any sport worth its salt has media coverage, and pickleball didn’t have that. These larger media organizations aren’t covering it, because they don’t see it as a big enough opportunity, [but] the people within this niche are starved for content” (Source 1).

By 2022, Shields had moved to Austin to pursue an MBA at UT Austin’s McCombs School of Business and joined SEAL, the school’s nine-week summer accelerator (Source 2).

“Shields’ goal entering SEAL was to see if his success with pickleball could scale to other emerging sports” (Source 2).

He summarized the program’s value: “SEAL forced me to sit down at least once a week and think, is this something that we can go do?” (Source 2).

The output of that process: Upswing Sports, a parent media platform. “Upswing Sports is a media platform that serves the emerging sports market including pickleball, Formula One, cycling, esports, disc golf, and much more” (Source 2).

Upswing’s own positioning: “Delivering digestible sports news in niches that need it. Upswing Sports is a newsletter-first media company focused on underserved niches and emerging sports markets” (Source 4).

As of February 2023, “the company’s profit margins are over 50%, and the startup just hired its fifth full-time employee” (Source 2).

“While Shields has received numerous offers to acquire the company, he’s turned down every last one” (Source 2).

Lesson for Creators

A “media company” positioning is more powerful than a “creator” positioning when the niche has no incumbent media coverage. The ESPN-of-pickleball framing did three things: (1) it told brands and athletes what kind of relationship to have with The Dink — coverage, not promotion; (2) it made the business sellable as a platform across more than one show or newsletter; (3) it gave Shields a credible reason to expand into emerging sports under Upswing Sports without losing focus. Crucially, the positioning came before the audience existed — Shields named the destination, then built toward it. Personal-brand creator businesses cap out at the operator’s personal output. Media-company-as-creator businesses can hire, expand into adjacent niches, and command higher margins because the brand carries weight beyond any individual.

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