Offsite
Offsite
Podcast Description
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.
Podcast Insights
Content Themes
The podcast delves into themes like entrepreneurship, mental health, personal development, and the intricacies of startup culture. Episodes feature discussions on various topics such as balancing authenticity with marketing in 2025 and the human aspects of storytelling in business, providing listeners with relatable insights and actionable advice.
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 scale when the funnel’s already working?
Jordan reunites with Brian Casel of Builder Methods for their biannual check-in. Jordan’s pushing Rosie from unichannel to multichannel, adding SMS to phone answering with a bold 5M ARR goal for 2026. Brian’s hitting his stride with Builder Methods Pro, where YouTube content fuels his membership business—December already matching November’s revenue halfway through. “The funnel is working as it stands today,” Brian notes. But he’s feeling the pressure: can one platform sustain growth? Both founders tackle the challenge of doubling down on what works while strategically diversifying. What happens when success creates its own constraints?
In This Episode:
(00:00) The Biannual Bootstrapped Web Update Returns
(02:01) Finding Focus Beyond the News Cycle
(07:16) Building With AI: Claude and Cursor Are Game Changers
(23:14) Rosie’s Big Leap: From Unichannel to Multichannel
(36:40) The Challenge of Selling Additional Products
(49:30) Builder Methods Growth Strategy for 2026
(54:33) Leveraging YouTube Content Across Multiple Platforms
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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:
Brian Casel: https://x.com/CasJam
Rosie AI: https://heyrosie.com/
Disclaimer
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