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.
All content for Offsite is the property of Jordan Gal and is served directly from their servers
with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
Are you selling AI solutions or business outcomes? (One makes money, one doesn't.) Jordan Gal hosts Craig Hewitt, founder of Castos and an AI content creator deep into his "100 Days of AI" project, alongside Chris Gimmer, co-founder of Fathom Analytics who just launched Good Metrics, a privacy-first analytics platform. Should OpenAI go public at a trillion dollars? The trio debates whether we're witnessing a bubble or the beginning of something bigger. Craig reveals why ChatGPT is "the worst AI tool" for his work—blasphemy or insight? Chris shares the painful decision to delay his launch for months after infrastructure issues. They tackle working from home versus office space, the coming wave of household robots, and why selling AI solutions directly might be the wrong approach. When will you have a robot in your house?
In This Episode:
(00:00) Music, Mood, and Getting Into Work Mode
(06:05) The Work From Home Versus Office Debate
(12:32) OpenAI Going Public at a Trillion Dollars
(20:09) Craig's 100 Days of AI and Why ChatGPT Isn't the Best
(26:29) Chris Launches Good Metrics After Infrastructure Delays
(34:56) When Will You Have a Robot in Your House?
(35:33) Selling AI Solutions Versus Selling Business Outcomes
(42:54) Vibe Running Your Company and Analytics Reality
(48:10) Multi-Channel Attribution and Why Data Is Always Fuzzy
Share with someone who would benefit, like and subscribe to hear all of our future episodes!
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: Craig Hewitt - Twitter/X: https://x.com/TheCraigHewitt Chris Gimmer - Twitter/X: https://x.com/cgimmer Rosie AI: https://heyrosie.com/
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.
