How Many CTOs
Brad Hefta-Gaub & Scott Porad
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Recent Episodes
S2E22 Removing Bottlenecks, Not People with Stephanie Sylvestre
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad is joined by guest Stephanie Sylvestre, founder of AvatarBuddy, an AI company started 10 years ago to help people be the…
S2E21 Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a high-performing engineering team that has effectively cleared its product backlog while using…
S2E20 Navigating the Future: Gas Town and Bespoke AI Agents
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss Brad's viral LinkedIn post arguing that AI has collapsed the economics that drove generalized…
S2E19 Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss spec-driven development and SpecKit, starting with Brad's story of a product owner resisted…
S2E18 A Fundamental Shift: Change Management, Psychological Safety, and AI's Impact on Engineering Leadership with Dr. Adam Link
In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by Dr. Adam Link, former senior engineering manager at Coinbase, who shares his background leading global…
S2E17 An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the recurring question: when it's appropriate to hire a VP of Engineering and how to divide…
S2E16 Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a conversation Scott had with coworkers after discovering Confluence connected to Google Drive…
S2E15 Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" interview Miguel Carranza Spanish-born co-founder/CTO of RevenueCat, who describes discovering…
S2E14 The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub talk with Nick Cawthon of gauge.io, who shares highlights from RSA 2026 and his career designing UX…
S2E13 Balancing Innovation and Safety: CTOs Check-In About AI Evolution
In this "What's on your mind?" episode of the "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how non-engineers using AI tools are increasing risk, with Brad…
S2E12 Engaging Employees in Security Appreciation with Robert Siciliano
In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub welcomes Boston-raised security speaker Robert Siciliano, who traces his path into security from early experiences with…
S2E11 Building Trust with AI: David Espindola on the Path Forward
In this episode of "How Many CTOs Does It Take?" podcast, Scott Porad hosts solo and interviews technologist David Espindola about AI. Espindola explains his path from engineer at fast-growing…
S2E10 Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub talk with Carter Huffman, CTO and co-founder of Modulate AI, about his path from machine learning work…
S2E9 Introducing the ADLC: The Agent Development Life Cycle
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" open with Super Bowl reactions and a meme about non-fans describing plays, then pivot to the ai.com…
S2E8 The Evolving Role of Tech Leadership with Philip Rosedale
In this episode of "How Many CTOs Does It Take?" podcast, Brad Hefta-Gaub is joined by guest co-host Philip Rosedale to explore the multifaceted role of a CTO, comparing it with the CEO position.…
S2E7 Predictions and Reflections: One Year Anniversary of the How Many CTOs Does It Take? Podcast
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" reflect on the first year of the podcast's publication, discussing Scott's ongoing questions about…
S2E6 Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub explore the evolving landscape of interviewing for programmer positions in the age of AI-assisted…
S2E5 From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub sit down with Ritesh Patel, co-founder of Ticket Fairy. Ritesh shares his journey from coding and…
S2E4 From the Dress Code to the Bottom Line: A CTO Business Primer
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the interplay between tech and business. Starting with comments about their own scruffiness and…
S2E3 The K-Shape of AI Development: Managing Digital Interns
In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub yet again delve into the transformative impact of AI on software engineering. Brad shares his 2025…
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How Many CTOs has published 73 episodes since February 2025, covering topics in Business, Entrepreneurship.
How Many CTOs is currently highly active with new episodes weekly. Average episode length is 39m.
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