Bootstrapped Web Update

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:  

• (00:00) Catching Up After Eight Months Apart 

• (05:33) Croatia Travel and European Vacation Wisdom 

• (10:31) Mixed Results and Growth Challenges in 2025 

• (16:00) When Advertising Data Leads You Astray 

• (25:05) The Creator-First Approach to Building Business 

• (35:15) YouTube Growth from 2,000 to 12,000 Subscribers 

• (46:50) Finding Product-Market Fit Through Customer Stories 

• (58:19) Surveys and Data Collection Strategies 

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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: 
Brian Casel: https://x.com/CasJam 
Jordan Gal: https://www.linkedin.com/in/jordangal/ 
Rosie AI: https://heyrosie.com/

Chapters

• (00:00:00) - Off-Site Podcast
• (00:00:44) - Bootstrapped Web: REQUEST FOR REQUEST!!
• (00:01:54) - Summer Fun: Margate, New Jersey
• (00:03:41) - Did You Guys Chase C crabs on the Beach?
• (00:04:38) - How's the summer going?
• (00:05:32) - A Girl's First Vacation
• (00:09:50) - How We're Feeling About 2019
• (00:16:20) - How To Manage the Sales funnel
• (00:18:52) - Post-Holidays Thoughts
• (00:21:00) - Building a Business with AI on YouTube
• (00:28:09) - Bobbie Methods: Future of Courses and Sessions
• (00:35:25) - How to Build a Startup with a Payload
• (00:42:23) - Reasons We Should Stop Advertising
• (00:47:59) - AI Voice for Oil Changes
• (00:53:51) - For Businesses, No Apps for Your Phone
• (00:54:26) - Lessons on How to Build with AI
• (01:01:50) - Rosie's New Homepage