Scaling pickleball leagues: zero to 65 cities in 18 months

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 jobGuest: Tommy Flaim, Founder, Silly Pickles🌐 Silly Pickles: sillypickles.com