
Episode 500: From Broke to Billionaire: Stephen Cloobeck’s $3.3B Mindset
From Habits and Hustle
Published 11/7/2025

From Habits and Hustle
Published 11/7/2025
Stephen Cloobeck didn’t climb the ladder. He built his own. In this episode, we talk about what it really takes to grow a billion-dollar company without a business degree: and why integrity, discipline, and grit beat credentials every time. We get into his biggest pivots, how mentorship shaped his…

Dan Fleyshman

Paul Alex Espinoza

Andy Frisella

Charles Schwartz

Joseph Shalaby

Heather Monahan | YAP Media

Sean Kelly

IBH Media