Scaling pickleball leagues: zero to 65 cities in 18 months
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Scaling pickleball leagues: zero to 65 cities in 18 months
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In this episode, we sit down with Tommy Flaim, founder of Silly Pickles, to unpack how he built one of the fastest-growing adult rec sports communities in the country.
Tommy shares his journey from investment banking to launching (and winding down) his first startup, and how he stumbled into building a scalable, software-powered league model that’s now live in 65+ cities.
We discuss:
• Why most adult rec leagues fail to attract young professionals
• How Silly Pickles scaled to a $3.4M run rate in 18 months
• The franchise-style operating model behind 100+ facility partners
• Raising capital while building custom software from scratch
• What founders should know before quitting their job
Guest: Tommy Flaim, Founder, Silly Pickles
🌐 Silly Pickles: sillypickles.com