Offsite
The Offsite Podcast is a candid, behind-the-scenes catch-up with host Jordan Gal and the friends, founders, and thinkers he admires. Each episode kicks off with real talk about work—what’s hard, what’s going well, and what’s unfolding in the moment. But just as important is what’s going on outside the lines of work: personal growth, ambition, envy, burnout, and the chaos of building while being human. With a rotating cast of co-hosts, the show is as much about chemistry as it is about insight.
This is a podcast about making sense of the mess and meaning of modern work and life, without taking ourselves too seriously. Honest updates, sharp takes, and the occasional therapy session, all recorded with a mic, a laugh, and a glass of something nearby.
Brought to you by Rosie, the AI-powered phone answering service for small businesses.
- Update frequency
- every 11 days
- Average duration
- 58 minutes
- Episodes
- 8
- Years Active
- 2025
Good Stress
Jordan Gal hosts Craig Hewitt, founder of Castos, in a raw conversation about entrepreneurial stress and competition. Craig's deep expertise in podcasting and YouTube content creation shines as he sh…
Bootstrapped Web Update
Should you build your audience before you build your product?
Jordan Gal reconnects with Brian Casel for their first Bootstrapped Web reunion in eight months, diving deep into the realities of scali…
"Drop In" Jesse Schoberg of Drop-In Blog
Is the "bootstrap or die" mentality actually killing your business growth potential?
Jordan Gal hosts entrepreneur Jesse Schoberg, co-founder of Drop-In Blog, a headless blogging platform that seaml…
From 200 Employees to Questioning Your Purpose - The Post-Exit Reality
What happens when you achieve your goal but lose your purpose?
Jordan Gal sits down with his brother Assaf just two weeks after Assaf closed the sale of his six-location Crunch Fitness franchise empir…
The American Wolf
Is the era of grinding and hustling finally over for smart founders?
Jordan Gal hosts fellow entrepreneur Christian Genco in this candid conversation about the "two wolves" battling inside every found…
Nothing Works
What's the real reason traditional SEO and content marketing are dead?
Jordan chats with Chris Gimmer, who's bootstrapping GoodMetrics.io and co-founded Snappa.com, and Craig Hewitt, CEO of Castos p…
Talk Story with Henry Poydar - AI and Authentic Leadership
What if the greatest human technology isn't AI or the internet, but something much simpler?
Host Jordan Gal welcomes serial entrepreneur Henry Poydar, founder and CEO of Steady, an AI-powered coordina…
Zero Percent Concerned
How do you balance honesty with effective marketing in 2025?
Welcome to the inaugural episode of the Offsite podcast. Host Jordan Gal, founder of Rosie AI, teams up with seasoned entrepreneurs Rob W…