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