How Many CTOs8 Jul 2025

How GenAI Is Changing the Two Guys in a Garage Founder Story

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome tech entrepreneurs and avid scuba divers Justin Wolf and Joe Malek to share the story behind their generative AI–powered scuba guidebook and community app. What started as a side project became a test case for building fast with LLMs and pushing the boundaries of what small, technical founding teams can accomplish.

The conversation dives deep into the reality of building with GenAI: the tools, the tradeoffs, and the surprising limitations. Along the way, they explore philosophical questions about human creativity, AI collaboration, and how founders might rethink MVPs, product-market fit, and even team size in this new era. From fighter jets and PACT tests to the Wall Street Journal's AI film experiment, this wide-ranging conversation connects code, culture, and curiosity in a way only How Many CTOs can.

00:00 Introduction and Welcome
00:36 Meet the Guests: Justin Wolf and Joe Malick
02:10 The Birth of a Scuba Diving App
03:22 Challenges and Solutions in App Development
06:27 Generative AI: A Double-Edged Sword
14:15 Technical Insights and AI Tools
21:29 Future Plans and Testing
26:43 The Importance of Control in Development
27:10 Automated Testing and PACT Tests
28:23 Wall Street Journal's AI Film Experiment
30:15 AI's Limitations and Human Creativity
32:06 AI in Fighter Jets: Human vs. Machine
33:55 The Future of AI and Human Intelligence
42:35 Generative AI and the Future of Work
47:12 The Role of Marketers in the Age of AI
50:18 Final Thoughts and Inspirations

Resources:

How Many CTOs Pod: https://howmanyctospod.com
Scott Porad: https://www.linkedin.com/in/scottporad/
Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/
Justin Wolf: https://www.linkedin.com/in/justinjwolf/
Joe Malek: https://www.linkedin.com/in/jomalek/

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