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 pr...
Jan 08, 2026•57 min
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 dissects data from both their companies, revealing counterintuitive truths about friction and conversion. "Eve...
Nov 19, 2025•50 min
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 based in San Miguel de Allende, Mexico, Jon discusses the challenges of building desktop software with long development cycles while p...
Nov 12, 2025•41 min
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 ...
Nov 05, 2025•52 min
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 his second child and shares insights on balancing creative work with reactive demands. What's the real cost of constant interruption...
Oct 29, 2025•1 hr 2 min
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 patience and deliberate choices. What drives a founder to stay lean while his company scales? The conversation traces back to 2012...
Oct 22, 2025•1 hr 21 min
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 pricing model to team-based pricing for their AI copilot for teamwork. "You get 18 summers with your kids, and then it's over," Henry ...
Sep 24, 2025•1 hr 1 min
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, a solo developer building File Inbox, shares his recent breakthrough with sleep onset insomnia through a carefully crafted supplement cocktail including melatonin and creatine. "I can create these tools now where I'm hunting," Christian explains about h...
Sep 18, 2025•1 hr 6 min•Ep. 9
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 toward distribution-first strategies. "The most important thing on YouTube is the packaging," Craig explains, detailin...
Sep 10, 2025•52 min
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 data is worse than no data," he reflects on lessons learned from over-relying on analytics. Brian discusses his pivot to Builder Meth...
Aug 27, 2025•1 hr 4 min
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 enterprise sales. After hitting a growth plateau at seven figures, Drop-In Blog pivoted their positioning and hired full-time marketing...
Aug 06, 2025•59 min
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 operation across Brooklyn, Bronx, and Queens, Assaf shares the emotional reality of transitioning from entrepreneurship to uncertainty. "Every day when you have a thing, you have a North Star, you have a purpose," Assaf reflects. "And now it feels like there...
Jul 23, 2025•55 min
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 bootstrapper, brings 12+ years of SaaS experience to discuss the eternal tension between "enough" wealth versus relentless growth. Both founders dig into their personal motivations, from Gal's immigrant drive to "slay the dragon" to Genco's struggle betw...
Jul 16, 2025•1 hr 3 min
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 Good Metrics as an alternative to Google Analytics, while Hewitt reveals how hiring marketer Mark Thomas increased trials by 30%. The conversation digs into AI's impact on marketing automation, with Gimmer n...
Jul 09, 2025•1 hr
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 ...
Jul 02, 2025•1 hr 5 min•Ep. 2
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 cre...
Jun 25, 2025•51 min
