How Many CTOs? Podcast Episodes
Welcome to the "How Many CTOs?" Podcast, hosted by Brad and Scott, where we dive deep into the intricate world of Chief Technology Officers. Each episode features candid conversations with guest CTOs who share their real-world experiences and insights on a wide range of topics. From building and upleveling high-performing engineering teams to managing and communicating the impact of tech debt, we cover it all. Discover strategies for measuring engineering productivity, refining processes, and balancing innovation with structured methodologies. Learn from experts about decomposing monolithic systems and keeping up with the latest technology trends. Whether you're a current or aspiring CTO, our podcast offers practical solutions and valuable advice to navigate the ever-evolving landscape of technology leadership. Tune in and join the discussion on overcoming the common challenges faced by CTOs today. Don't forget to subscribe, rate, and review! #TechLeadership #CTO #techpodcast
91 episodes
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S2E40Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between
TaskRabbit's overnight AWS region migration from us-west-1 to us-west-2, describing the months of preparation, detailed runbook, large war-room call,…
S2E23Understanding The Fear: Adaptive Leadership in the AI Age
Growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring leaders to disrupt old stabilizing practices. They…
S2E38Simplifying Tech Through Empathy and Understanding with Frank Bravo
Is joined by guest Frank Bravo, a Bay Area technologist who spent 30 years as CTO in local media, helping put a newspaper's full editorial content online…
S2E37Managing Skepticism: Balancing Tradition and Technology with AI
How AI is changing software engineering referencing Kent Beck's idea that AI makes much existing knowledge less useful while making a smaller portion far…
S2E36From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing
Scott Hanson, founder and CTO of Ambiq, a company focused on ultra-low-power chips for "intelligence everywhere," with 300M+ units shipped into wearables…
S2E35Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher
Andy Boettcher, Chief Innovator of DoubleTrack, a boutique data and AI consultancy. Andy recounts his 33 years across systems, development, with 13 years…
S2E34The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave
Jack Moldave of Eyebot, a company he co-founded nearly six years ago to make getting glasses as easy as buying shoes by enabling on-demand vision tests…
S2E33Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery
A leadership conversation where three senior stakeholders wanted different outcomes from engineering: delivering faster, maximizing utilization, or…
S2E32The Pace of Innovation: Systems Thinking for Faster Engineering
Open with travel and sports talk, including World Cup rules, then pivot to Scott's change-management training on systems thinking and unspoken norms. They…
S2E31Method to the Madness: A CTO Framework for Systemic AI Adoption
How CTOs must frame narratives that help teams organize around ideas, inspired by how Scott explained his company's AI work to a non-technical friend. The…
S2E30There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin
Are honored to interview Robert "Uncle Bob" Martin, who recounts his 60+ year programming journey from a three-bit binary device and years of assembly to…
S2E29Is Uncle Bob Right? Reading Code vs. Architecting the Future
How Robert "Uncle Bob" Martin—author of Clean Code and Agile Manifesto signer—sparked online controversy by saying he no longer reads the source code…
S2E28Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers
Token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and broader industry moves to optimize tokens. The hosts argues…
S2E27This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI
How managing armies of coding agents can be physically draining, likening it to context switching in flat organizations. Scott references Yuval Harari's…
S2E26From Chaos to Control: Bringing Specification Driven Design to Vibe Coding with David Bauer
Is joined by Dr. David Bauer of Axonis AI, who shares how his background in distributed computing, startups, and the U.S. intelligence community led him…
S2E25Introducing Skein and Beaker Stack: Using AI Agent Engineers to Ship SaaS Faster
In this special episode of " How Many CTOs Does It Take? " podcast, hosts Scott Porad and Brad Hefta-Gaub discuss Brad's experiment proving that AI can…
S2E25AI and the Data Swamp In Your Backyard with Ben Wilcox
Guest Ben Wilcox, CTO and CISO of ProArch, a Microsoft-focused data and AI system integrator. Wilcox describes his path into system integration, from…
S2E23Pioneering Music Education with John von Seggern
Brad Hefta-Gaub interviews John Von Seggern, founder/CEO/CTO of Future Proof Music School, about his shift from musician and online educator to building…
S2E22Removing Bottlenecks, Not People with Stephanie Sylvestre
Is joined by guest Stephanie Sylvestre, founder of AvatarBuddy, an AI company started 10 years ago to help people be the best version of themselves.…
S2E21Pioneer or Perish: How and When to Evolve Your Engineering Org Toward the AI Development Life Cycle
A high-performing engineering team that has effectively cleared its product backlog while using AI heavily, including a senior engineer who surprised Brad…
S2E20Navigating the Future: Gas Town and Bespoke AI Agents
Brad's viral LinkedIn post arguing that AI has collapsed the economics that drove generalized SaaS, enabling more bespoke software for underserved SMBs…
S2E19Uncovering Hidden Ambiguities: Why Product Managers Need to Adapt to AI Tooling
Spec-driven development and SpecKit, starting with Brad's story of a product owner resisted SpecKit because it produced "too many words," alongside…
S2E18A Fundamental Shift: Change Management, Psychological Safety, and AI's Impact on Engineering Leadership with Dr. Adam Link
Is joined by Dr. Adam Link, former senior engineering manager at Coinbase, who shares his background leading global teams through highly technical…
S2E17An Ideal Partnership: How and When to Split CTO and VP of Engineering Duties
The recurring question: when it's appropriate to hire a VP of Engineering and how to divide responsibilities so the CTO can better align product,…