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.
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 coordination intelligence platform. Henry has had extensive experience with multiple exits and backing from notable investors, including the founder of Red Hat. The conversation explores Henry’s philosophy that “the greatest human technology is a story” and his belief that authentic storytelling must never drift between personal, investor, and sales narratives. What makes storytelling so crucial for entrepreneurs? How do you maintain authenticity while scaling your message?
The discussion spans personal reflections on parenting and family dynamics to deep dives into AI pricing models, competitive positioning, and the challenges of category creation. Henry shares insights on building high-performing remote teams through trust, shared context, and balanced autonomy. Topics include the evolution of San Francisco’s tech culture, the tension between outcome-based versus user-based pricing in AI, and concerns about career paths in an increasingly automated world. Jordan and Henry examine how middle children develop natural storytelling abilities and debate the future impact of AI on entry-level careers.
In This Episode:
- (00:00) The Greatest Human Technology Is A Story
- (12:42) San Francisco’s Tech Culture Transformation
- (20:24) Competing Like New York Bankers in Silicon Valley
- (28:23) Where Are You in Your Storytelling Journey
- (35:03) Creating Shared Context for Remote Teams
- (43:01) Middle Child Dynamics and Natural Storytelling
- (50:16) Pricing Challenges in the AI Era
- (57:40) Labor Replacement and the Future of Careers
- (1:01:40) Learning to Think vs Rote Memorization
- (1:03:17) This Is Water and Reaching for the Stars
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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:
Henry Poydar: https://x.com/henrypoydar
Steady: https://www.steadyai.io/
Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/
Disclaimer
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