How Many CTOs

Brad Hefta-Gaub & Scott Porad

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

  1. 1 day ago

    Method to the Madness: A CTO Framework for Systemic AI Adoption

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss 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 hosts outline four intertwined AI workstreams: getting AI to handle increasingly complex engineering (from functions to features to systems), moving toward autonomous "dark factory" software development, scaling AI adoption through standards and systems (shifting from organic experimentation to systemic usage, like AI code review and possible security/architect review agents), and managing token spend, including discussion of token-maxing incentives, looping, and interest in local inference and vendor lock-in mitigations such as AWS Bedrock. The episode also includes numerous anecdotes from the hosts engineering teams and time as parents. 00:00 Cold Open 00:45 Recharge Week Catchup 02:02 Sapiens and Storytelling 03:14 Cognitive Revolution Explained 05:11 AI Elevator Pitch At Baseball Game 06:42 Three AI Workstreams 10:35 Complex Engineering with AI 11:30 Building SaaS with Agents 13:05 Dark Factory Automation 14:30 Scaling Standards and Systems 17:41 Organic to Systemic Adoption 19:41 Scouts and Shared Conventions 20:49 Spec Driven Development Debate 21:33 Middle Ground of Feature Brief 23:31 Security and Architect Agents 25:02 Token Spike Story 28:42 The Innovation of Reuse 29:40 Token Management Debate 33:08 Looping Burns Tokens 35:09 Local Inference and Privacy 38:43 Vendor Lock In and Bedrock 41:58 CTO Narrative and Framework 44:32 Wrap Up and Credits   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/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AIRevolution #Automation #TokenManagement #AIInnovation #ComplexEngineering #AIAdoption #FutureOfAI #TechEnthusiast #VendorLockIn #EngineeringExcellence #SoftwareStrategies #AIInsights #CTOCommunity #AIStandards #TechPodcast #EngineeringLeadership #OrganizationalChange #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding

  2. 4 Aug

    There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 C, C++, and Java, to now using AI agents to code. He explains how the Agile movement emerged from the design patterns community, Extreme Programming, and the 2001 Snowbird meeting that produced the Agile Manifesto. He argues Agile arose as a response to failed upfront analysis/design and emphasizes feedback, small iterations, and early discovery of uncertainty, while noting Agile was later overtaken by project managers and certification-driven Scrum. Martin discusses the ongoing tension between business roadmaps and engineering uncertainty, advising ranges over firm dates, and connects Agile lessons to AI coding: neither big upfront specs nor "vibe coding" works without strong engineering disciplines enforced by deterministic tools (tests, static analysis, CRAP metric), enabling developers to step back from reading syntax while still guiding quality. The episode ends with a discussion on the future of training engineers and the possibility of an apprenticeship model of learning. 00:00 Cold Open 00:20 Meet Uncle Bob 01:24 First Computer Memories 03:19 From Assembly to C 05:04 Coding With AI Agents 07:00 How Agile Was Born 12:04 Why Waterfall Failed 19:01 Agile Gets Hijacked 21:23 Roadmaps vs Reality 26:21 Agile Lessons for AI 30:52 Agent Myopia Risks 31:40 Deterministic Tooling 32:48 CRAP Metric Whip 34:29 I Don't Read Code 38:14 Assembly to C Lessons 41:29 Abstraction History Repeats 43:14 AI Broke The Plateau 48:09 Agents In Practice 52:14 Quality Gates For All 56:03 Training New Engineers 58:26 Apprenticeship Model 01:00:38 Closing Thoughts 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/  Bob Martin: https://x.com/unclebobmartin Bob's book: Clean Agile: Back to Basics  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #Agile #UncleBob #AgileManifesto #AgileDevelopment #AIRevolution #FutureOfTech

  3. 28 Jul

    Is Uncle Bob Right? Reading Code vs. Architecting the Future

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss 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 produced by his programming agents. They unpack his argument that strong "control systems" like automated unit and end-to-end tests, static analysis, and architecture acceptance criteria can replace line-by-line review, shifting human attention to higher-level architecture and justification. The hosts debate the limits of this approach in legacy systems lacking tests, explore how CTOs create quality through hiring and checks-and-balances, and emphasize spot-checking high-risk work such as one-way-door decisions, infrastructure migrations, data model design, and surprising estimates. They also consider building architecture/security agents and why Uncle Bob's opinions carry influence. 00:00 Podcast Kickoff 00:58 Who Is Uncle Bob 03:01 Agentic Coding Controversy 04:18 Quality Controls Over Reading 06:39 Legacy Code Testing Problem 09:49 Belligerents in the Debate 10:47 What Code Reviews Catch 12:31 Agents for Architecture Security 15:35 Multiple Reviewers Probability 17:41 CTO Checks and Balances 18:48 AWS Region Move Rollout Plan 20:27 Data Center War Stories 22:16 Reviews as Conversations 23:15 Beyond Reading Code 24:11 Presenting Upward Forces Clarity 25:44 CTO as Company Voice 27:49 Spot Checks and Breakpoints 29:11 When to Dive In 30:05 Data Intuition Stories 33:08 Debugging Big Estimates 36:08 Uncle Bob Agents 39:39 Why We Care 42:05 Wrap Up and Credits 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/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #UncleBob #Agile #AgileManifesto #CleanCode #AIAgents #CodingRevolution #AIinTech #LegacySystems #QualityControl #AgenticProgramming #EngineeringExcellence #TechDisruption #ProgrammingWisdom #AgilePrinciples #CodingGiants #TechEvolution #ModernEngineering

  4. 21 Jul

    Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and broader industry moves to optimize tokens. The hosts argues companies should focus on value and learning rather than premature token optimization, while still adding circuit breakers to prevent runaway costs. They explore shifting to local inference and open-weight/open-source models for cost, privacy, and control, citing concerns about vendor policy changes like Fable's retention and classifier behavior. The conversation expands into how AI shifts bottlenecks from coding to product management, experiments pairing product and engineers using SpecKit, and how AI may realize Agile's iterative promise. They close on distribution as a key frontier and the career opportunity of being early in AI, likening it to the early internet era.   00:00 Cold Open 00:27 Podcast Kickoff 00:46 Anniversary Trip in Maui 02:54 Copilot Budget Surprise 05:15 Token Panic Backlash 07:54 Value Over Tokens 13:33 Local Models Rising 15:46 SaaS Apocalypse Talk 17:29 Cycle Time vs Value 20:19 SpecKit Pairing Experiment 22:43 AI Meets Agile Promise 24:50 Spec First Agile Debate 29:40 Builders VS Managers 31:40 Scaffolding Vibe Coders 32:29 Distribution Is Hard 35:51 Snoring App Niche 38:43 Targeted Ads Reality 40:07 Open Source Pushback 42:11 Three Pressures On CTOs 44:56 Privacy And Data Control 53:38 Frontier Models Trust Issues 56:19 Three Truths For Teams 58:09 Early Internet Lessons 59:44 Wrap Up And Credits   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/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #Entrepreneurship #TokenMaxxing #LocalInference #AI #AIProgramming #AIAssistedProgramming Agile #Innovation #OpenSource #Privacy #OpenWeight #AIRevolution #Leadership #Innovation #AgileDevelopment

  5. 14 Jul

    This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how managing armies of coding agents can be physically draining, likening it to context switching in flat organizations. Scott references Yuval Harari's "Sapiens," connecting the cognitive and agricultural revolutions to modern pressures. The hosts debate whether AI causes coding skills to atrophy and blocks junior engineers from becoming seniors, framing "pulling the slot machine lever" as shipping code you don't understand. Brad shares a pre-AI story about copying Stack Overflow code for a 3D triangle point test, leading to lessons about ambiguity and understanding. They argue this cargo-cult behavior predates AI, though AI makes laziness easier, while curiousity can accelerate learning. They also discuss "taste" as effective engineering opinions, shifting skills toward interrogating LLMs, and a potential K-shaped industry split between WYSIWYG builders and engineers closer to the metal. 00:00 Cold Open 00:21 New Listener Surprise 01:36 Managing AI Agents Burnout 04:26 Sapiens and Cooperation 07:46 AI Complaints Are Engineering 08:49 Slot Machine Coding Metaphor 09:41 Stack Overflow Triangle Story 15:41 Cargo Culting and CopyPasta 16:30 Juniors to Seniors in AI Era 23:42 Curious vs Lazy AI Use 27:08 Models Improve and Safety 28:39 Engineering Is Shaping 29:58 Junior Vs Senior Judgment 31:03 What Is Taste 34:22 Engineering Job Shifts 37:25 Curiosity Still Wins 39:59 Build Stuff To Grow 44:04 Learning Through Debugging 46:25 Managing LLM Atrophy Risk 49:55 Pair Programming And Market Pressure 53:31 K Shaped Future 55:29 Wrap Up And Credits 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/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #StackOverflow #CargoCulting #JuniorvsSeniorEngineers #JuniorEngineers #SeniorEngineers #AI #AIProgramming #AICoding #AIAssistedCoding #AIAssistedProgramming #SlotMachines #InnovationVsComplacency #ProgrammingLife #CodingChallenges #ArtificialIntelligence #LazyCoding #SoftwareSkills #AIInCoding #EngineeringChallenges #DeveloperJourney #InsideTech

  6. 7 Jul

    From Chaos to Control: Bringing Specification Driven Design to Vibe Coding with David Bauer

    In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub 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 to Axonis AI's federated data layer used for federated learning, data fusion, semantic ontologies, and decision intelligence. Bauer describes how encouraging engineers to use any LLM tool led to incorrect, unreviewable PRs and broken releases, especially in security-critical areas, as MCP tooling sprawl made tool selection unreliable. Axonis rebuilt its development workflow around specification-driven design with extensive automation, agentic workflows, Git hooks, and spec-centric Agile tracking, shifting engineers from code-centric work to "vibe speccing" and system understanding. They prioritize end-to-end integration tests as the primary quality gate, keep integration test implementations tightly controlled, and automate much of GitLab interaction while using their own compliance/attestation tooling to tie decisions to evidence across the company. Brad and Bauer engage in a healthy debate about the need for unit tests in the age of AI-assisted programming, and they end the episode by discussing how to empower engineers who focus on identifying and solving business needs, rather than the minutia of the actual coding. 00:00 Cold Open 00:27 Meet Dr David Bauer 01:15 Axonis AI Origin Story 02:54 Why Startups Must Use AI 04:42 When Vibe Coding Breaks PRs 07:29 Team Scale And Pain Points 08:29 MCP Tool Sprawl And Gateway 10:21 Specification Driven Design Fix 18:49 Quality Gates And Integration Focus 21:44 Unit Tests Debate Begins 26:22 Robot Test Validation 28:04 Unit vs Integration Tests 29:51 Vibe Speccing Workflow 32:52 Engineers as PMs 34:55 Compliance Tooling Attestations 38:36 Federated Data Evidence 40:17 Advice for Engineering Leaders 43:24 Specs Beyond Engineering 45:56 Making Specs Consumable 49:26 Wrap Up and Credits Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  David Bauer: https://www.linkedin.com/in/dr-bauer/  Axonis AI: https://www.axonis.ai/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #VibeCoding #IntegrationTesting #AI #AIAssistedCoding #AIAssistedProgramming #ProductDevelopment #Agile #SpecificationDrivenDesign #SystemDesign #AIInTech #AgileProcesses #LeadershipDevelopment #ContinuousIntegration

  7. 30 Jun

    Introducing 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 dramatically boost output for teams with strong engineering practices. Brad shares an MIT-licensed open-source SaaS template called Beaker Stack, which includes web and mobile scaffolding, CI/CD for preview/staging/production, automated setup, observability, email tooling, and Stripe-based tiered billing with feature gating. He then uses it to build Skein, a cloud-hosted shared "memory backplane" served via an MCP endpoint that lets multiple AI tools and agents read/write memories with strong security controls and auditing. Brad describes hiring four AI agent "engineers" (Diego, Mei, Rahul, Sarah) with persona "soul files," running them in Nanocloud/Nanoclaw containers for security, coordinating work via Telegram and GitHub, and applying spec-driven, test-heavy guardrails to ship Skein in about 10 days of part-time work. Scott asks questions about Brad's process, and the two hosts debate how different perspectives effect an engineer's process, be they AI agent or human coworker. A video version of this episode can be found on the How Many CTOs YouTube channel! 00:00 Cold Open 01:05 AI Velocity Thesis 02:16 Shipping SaaS Every Six Weeks 04:37 Beaker Stack Tour 08:11 Meet The AI Engineers 09:52 Agent Workflow And Reviews 12:11 Building Skein Shared Memory 14:45 10 Day Build And Metrics 18:51 How Skein Uses Beaker Stack 24:20 Under The Hood Supabase Vectors 25:50 Admin UI Walkthrough 26:27 Managing Agent Workforce 26:49 Nanoclaw Security Containers 28:59 Telegram Agent Ops 30:32 Agent Personas Backstories 33:31 Thinking Hats Perspectives 37:25 Human Loop Guardrails 41:47 Marketing Distribution Channels 47:18 Factory Vision Rapid Launch 48:46 Wrap Up Credits 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/ Skein: https://getskein.ai/ Beaker Stack website: https://beakerstack.com/ Beaker Stack GitHub: https://github.com/Artificer-Innovations/BeakerStack #techpodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #SaaS #Engineering #Development #BeakerStack #Skein #TechInnovation #AIRevolution #AIEngineering #AIAssistedCoding #AICoding #AIProgramming #AIAssistedProgramming

  8. 23 Jun

    AI and the Data Swamp In Your Backyard with Ben Wilcox

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview guest Ben Wilcox, CTO and CISO of ProArch, a Microsoft-focused data and AI system integrator. Wilcox describes his path into system integration, from cloud transformation and building managed security services, and now focused on helping customers adopt AI securely. The discussion centers on enterprise "data swamps," where unstructured, stale, and sensitive data create inaccurate AI outputs, and the new security risks as connectors make information easier to access. Wilcox argues organizations need stronger data governance, classification/labeling, segmentation, and purging, and should start with narrow, high-value AI use cases supported by cleaner data pipelines to improve accuracy and drive stakeholder buy-in. The hosts debate whether AI truly hallucinates or if faulty answers come from poor data, and whether the need for guardrails is anything new. Wilcox ends the episode reminding listeners that they are not alone in managing complex data. 00:00 Cold Open 00:22 Meet the Guest 03:00 What System Integrators Do 06:44 Modern SI for AI 09:39 Enterprise Data Swamp 15:08 Governance and Classification 17:41 Getting Budget Buy In 21:21 Bad Data vs Hallucinations 23:23 Bad Data Slows Everyone 24:43 Bronze Silver Gold Layers 26:53 Selling Data Debt Fixes 28:30 Scoped Copilot Show And Tell 31:04 AI Exposes Old Data Issues 33:11 Fusion Teams And Guardrails 37:00 Agents Need Real Controls 43:24 Defaults YOLO And Reviews 46:18 Wrap Up And Credits 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/  Ben Wilcox: https://www.linkedin.com/in/ben-wilcox/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #CISO #ProArch #Microsoft #SystemIntegration #AISecurity #DataSecurity #AI #DataSwamps #CloudTransformation #DataManagement #Cybersecurity #SystemIntegrators #Innovation #DataGovernance #CloudSolutions

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About

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

Information

  • Creator
    Brad Hefta-Gaub & Scott Porad
  • Years Active
    2025 - 2026
  • Episodes
    82
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    How Many CTOs

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