Good Stress

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, detailing his shift from $19/month models to higher-value consulting. They explore AI tools like Manus for scaling outreach and debate whether conventional marketing still works. How do you compete when everyone has access to the same AI tools?

In This Episode:

• (00:00) Better Than Yesterday But Still Stressed

• (04:10) The Great Lock-In of September to December 2025

• (08:57) Email Marketing Project with Mark Thomas

• (15:46) YouTube Strategy and the 100 Days of AI Experiment

• (26:10) Confronting the Reality of AI Competition

• (36:05) Building Integrations in Hours with Claude Agents

• (46:01) The Opportunity in Corporate AI Training

• (53:20) Positioning for the Coming Job Market Disruption

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

Chapters

• (00:00:00) - The most important thing on YouTube
• (00:00:20) - Off-Site Podcast: How To Get Out Of Recession
• (00:03:20) - What is it about stress in the year?
• (00:06:09) - Summer Business: Will It Slow Down?
• (00:08:25) - How to Send More Emails
• (00:12:13) - How To Avoid Legal Issues With Text Messages
• (00:14:25) - How to Do a Podcast and a Video Every Day
• (00:18:17) - How To Make a Video on YouTube
• (00:20:59) - How to Make a Scriptment on Screen
• (00:22:04) - Jordan on Making His Own Ad
• (00:24:00) - The Competition in AI Voice
• (00:29:17) - How to Get More Out of Content Marketing than B2C Marketing
• (00:31:36) - How to Cheat at AI-based Deals
• (00:33:50) - Kastos Integrations: The Right Partner for AI?
• (00:39:14) - Onboarding and the Drop Off Points
• (00:40:57) - A Hundred Day Project: Building an Audience
• (00:42:20) - B2B AI Training
• (00:46:34) - The Future of Small Law Firms
• (00:49:19) - How to Build a Billion-Dollar Business With AI