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 Methods, a creator-first approach focusing on building with AI, growing his YouTube channel from 2,000 to 12,000 subscribers. How do you balance YouTube content creation with monetization? Both founders explore the tension between data-driven decisions and gut instincts while building sustainable, profitable businesses. 
 

In This Episode:  

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 
Jordan Gal: https://www.linkedin.com/in/jordangal/ 
Rosie AI: https://heyrosie.com/

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 staff in Eastern Europe. "After a plateau for about a year, all of a sudden doing a demo doesn't sound so bad," Jesse admits, about his evolution from credit-cards-only to enterprise contracts. The conversation explores remote team building, the global talent arbitrage, and how Jesse discovered AI-powered SEO as their hook for LinkedIn growth. How do founders know when it's time to abandon their original playbook? 

In This Episode:  

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: 
Jesse Schoberg: https://x.com/JesseSchoberg  
Jordan Gal: https://www.linkedin.com/in/jordangal/ 
Rosie AI: https://heyrosie.com/ 
 

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's nothing." The conversation explores the ten-month deal process, the weight of managing 200 employees, and the challenge of finding what's next. What does freedom actually feel like when you've spent over a decade grinding? How do you process relief, guilt, and the search for new purpose?

In This Episode: 

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:

LinkedIn: Assaf Gal https://www.linkedin.com/in/assafgal/

Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/

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 between minimalist philosophy and capitalist ambition. What drives someone to want "millions of dollars post-tax in a personal bank account"? How do you balance family life with business obsession? The conversation reveals the raw psychology behind entrepreneurial success and the frameworks top founders use to navigate major decisions.

In This Episode: 

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:

Christian Genco: https://x.com/cgenco

File Inbox: fileinbox.com

Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/

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 noting that Python scripts can identify potential customers on Twitter and Reddit. "Nothing is working for us" in terms of new acquisition channels, admits Hewitt. How are seasoned entrepreneurs adapting their strategies when traditional marketing playbooks fail? The trio also discusses AI-powered SEO strategies and the challenges of scaling beyond paid advertising in today's saturated market. 
 

In This Episode:  

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: 
 

Christopher Gimmer: https://x.com/cgimmer 

Craig Hewitt: https://x.com/TheCraigHewitt 

Jordan Gal: https://www.linkedin.com/in/jordangal/ 
Rosie AI: https://heyrosie.com/ 

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: 

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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/

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 creation. Both guests offer contrasting perspectives on building sustainable businesses - Rob through his venture fund and content empire, Aaron through his personality-driven education business. 
 

The trio dives deep into the realities of running different business models, from Jordan's VC-backed growth strategy to Aaron's bootstrapped course business to Rob's venture fund operations. They explore the psychological challenges of founder life, including comparison traps and social media facades. "What I find myself and others like yourselves is that it does hold us back in our marketing because we are too shy, too real, too careful," Jordan observes. How do successful entrepreneurs balance authenticity with effective marketing? What's the real difference between income-focused and outcome-focused business strategies? 
 

In This Episode:  

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: 
 

Rob: https://x.com/robwalling 

Aaron: https://x.com/aarondfrancis 

Jordan Gal: https://www.linkedin.com/in/jordangal/ 
Rosie AI: https://heyrosie.com/ 
Startups for the Rest of Us Podcast (Rob Walling) 

Mostly Technical Podcast (Aaron Francis & Ian Landsman)