OSL Podcast: What a Fractional CTO Really Thinks About Vibe Coding, AI Prototyping, and the Future of Software

Jason Margolin, a seasoned tech professional and fractional CTO, joins Rob Woodhead to talk about a career that started with self-taught HTML at 13 and wound its way through Meta before landing in the world of startup advisory.They get into the big question on every non-technical founder's mind right now: how far can you actually get with AI-assisted prototyping before you need real engineering firepower? Plus, what's genuinely changing about the speed at which senior engineers can move, and what does good AI integration actually look like in practice?

Expect honest conversation about:

• Teaching yourself to code before Stack Overflow existed
• What working at Meta really teaches you about scale
• How non-technical founders can use AI to prototype and de-risk their ideas
• Where vibe coding hits its limits (and why that matters)
• The AI product helping GP practices manage appointment booking
• What the best fractional CTOs actually do for early-stage businesses

A must-listen for anyone curious about where AI is taking software development, and what it means if you're building something without a technical co-founder.