From $100 to a $30M Private Equity Exit: Lessons from Serial Entrepreneur Lenny Feinstein (#28)

Exit Algorithms · Mar 4, 2026 · 52m

In this episode, I sit down with Lenny Feinstein, a serial entrepreneur who bootstrapped multiple eight-figure businesses from the ground up and successfully exited both a commercial cleaning company at $30 million in revenue to private equity, and a 512-unit property management portfolio in Tampa.​

We discuss:

– Lenny's unconventional journey from juvenile delinquent and hitchhiker to building a cleaning company from a $100 investment and a moped, serving over 1,000 restaurants a night across 30 states.​

– Why undercapitalization is one of the most brutal lessons in scaling, and how taking…