In The Money · 2026-07-22 · 31 min
What happens when a former consumer brand founder gets tired of the working capital grind, spots a broken format in adult recreational sports leagues, and decides to engineer the conditions for adults to actually make new friends? Tommy Flaim, Founder of Silly Pickles, joins In The Money to break down one of the more unexpected growth stories in the consumer space, a pickleball league that started as a side hustle managed on Microsoft Excel, hit a waitlist of over a thousand players in its first few seasons, and is now in 75 metro areas across the US, Canada, and Australia doing $6 million in run rate on just $750K raised.
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