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.
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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.
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 Walling and Aaron Francis for our first episode. Rob Walling, founder of TinySeed and host of Startups for the Rest of Us, brings 15 years of podcasting experience and deep SaaS expertise. Aaron Francis runs Try Hard Studios and co-hosts Mostly Technical, focusing on screencast education and course creation. Both guests offer contrasting perspectives on building sustainable businesses - Rob through his venture fund and content empire, Aaron through his personality-driven education business.
The trio dives deep into the realities of running different business models, from Jordan's VC-backed growth strategy to Aaron's bootstrapped course business to Rob's venture fund operations. They explore the psychological challenges of founder life, including comparison traps and social media facades. "What I find myself and others like yourselves is that it does hold us back in our marketing because we are too shy, too real, too careful," Jordan observes. How do successful entrepreneurs balance authenticity with effective marketing? What's the real difference between income-focused and outcome-focused business strategies?
In This Episode:
(00:00) Welcome to the Offsite Podcast
(01:13) How Rob Walling Helped Jordan Break Into Tech
(06:14) What Rob and Aaron Are Working on This Week
(14:18) The Psychology of Comparison and Competition
(21:57) Why Authenticity Can Hold Back Your Marketing
(24:49) Jordan's Board Meeting Experience as a VC-Backed Founder
(32:04) The Challenge of Running Non-SaaS Business Models
(38:31) How to Make a Podcast Good - Expert Advice
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About the Show
Jordan Gal, founder and CEO of Rosie AI, hosts the Offsite Podcast where he teams up with rotating entrepreneur friends to explore what's happening in their work and beyond. After successfully building and selling CartHook, Jordan now leads a VC-backed company while sharing candid insights about the realities of startup life. The show combines real-time business updates with deeper conversations about founder psychology, growth strategies, and the personal side of entrepreneurship that rarely gets discussed publicly.
Resources:
Rob: https://x.com/robwalling
Aaron: https://x.com/aarondfrancis
Jordan Gal: https://www.linkedin.com/in/jordangal/ Rosie AI: https://heyrosie.com/ Startups for the Rest of Us Podcast (Rob Walling)
Mostly Technical Podcast (Aaron Francis & Ian Landsman)
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.
