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.
Episodes
What if charging upfront actually converts better than free trials for your product?
Jordan Gal sits down with Ruben Gamez, founder of SignWell and creator of BidSketch, for a tactical deep dive into SaaS fundamentals. Ruben built two successful products despite never finishing high school—a testament to execution over credentials. Should you charge upfront or offer free trials? The duo...
Are you building a business that fits your personality or following someone else's playbook?
Jordan Gal hosts Jon Ewalt, founder of Roaster Tools, a comprehensive ERP system built specifically for specialty coffee roasters. After selling his Portland coffee roastery, Jon dove into software development nine years ago and has been "playing catch up" ever since. Now base...
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? Th...
Could sharing your most shameful moment actually accelerate your career?
Jordan Gal teams up with fellow entrepreneurs to discuss work and life beyond business. In this episode, Jordan sits down with returning guest Christian Genco,a software engineer and entrepreneur navigating the challenges of scaling products while maintaining focus. Christian recently welcomed hi...
Could a single technical person who enjoys talking to customers really build a ten million dollar business alone?
Host Jordan Gal sits down with Jesse Hanley, founder of Bento, an email marketing platform, for an exploration of contrasting entrepreneurial approaches. Jesse operates solo from Fukuoka, Japan, building Bento into a single-digit-millions business through ...
What price are entrepreneurs willing to pay for presence?
Jordan Gal, founder and host of Offsite, reconnects with Henry Poydar, CEO of Steady, to discuss the personal and professional transitions of being an empty nester entrepreneur. Henry, who recently dropped off his twin boys at college, reflects on the emotional journey while pivoting Steady from a per-user pric...
Are you still hiring humans when AI could 10x your output for a fraction of the cost?
Jordan Gal hosts entrepreneur Christian Genco on the Offsite podcast, where they dive deep into optimizing personal performance for business success. Christian,...
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 shares his "100 Days of AI" experiment—publishing daily videos to build authority in the AI space. The discussion reveals how both founders are pivoting from traditional SaaS playbooks to...
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 scaling SaaS businesses. Jordan shares Rosie's rapid growth to $1M ARR in eight months, followed by painful plateau challenges when advertising optimization went wrong. "Bad dat...
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 seamlessly integrates blogs into existing websites. Jesse, a nomadic founder currently between Bangkok and Europe, shares his journey from bootstrap mentality to embracing enter...
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 empire. After 13 years building a 200-employee oper...
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 founder. Genco, creator of File Inbox and seasoned ...
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 podcasting platform, about the current state of customer acquisition. Gimmer explains building ...
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 exte...
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 ...
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