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. 19h ago

    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

    50 min

  2. Jun 23

    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

    48 min

  3. Jun 16

    Pioneering Music Education with John von Seggern

    In this episode of "How Many CTOs Does It Take?" podcast, 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 AI features using tools like Claude Code, n8n, and MCP servers. John describes the school's personalized learning approach using an AI chatbot "Cadence" integrated with student history and curriculum, hosted on LearnWorlds, and explains solving integration limits by creating an MCP server and scraping LearnWorlds pages into a mirror database for context. They discuss security and brittleness concerns with AI-built software, using audits and cross-checking between Codex and Claude, and how models enable refactoring. John outlines a hybrid org where human teachers handle advanced artistry via live workshops and mentoring, supported by an internal agent "Nova," and shares advice: state big goals upfront and have AI ask questions to clarify plans. The episode ends with a discussion on the future of AI generated music, and how AI can be a powerful tool for good. 00:00 Cold Open: People Still Matter 00:20 Meet John Von Seggern 02:40 From No Code to Claude 06:41 What The Platform Does 08:42 LMS Choice LearnWorlds 09:33 Context And RAG Logic 11:26 Building An MCP Server 12:16 Scraping For Lesson Data 16:02 Music Mindset For Systems 17:29 Vibe Coding Risks 20:14 Refactoring As Models Improve 22:49 Guardrails For Agents 23:13 Democratizing Code Limits 26:26 Supervising Agents Anywhere 28:39 Building Nova Business Brain 30:34 Hybrid School Team Setup 33:35 Advice: Ask 100 Questions 36:24 AI Music Future Debate 40:53 Look On The Bright Side, Closing Thoughts 43:22 Wrap Up And Credits   Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  John von Seggern: https://www.linkedin.com/in/johnvon/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #MusicEducation #TechInnovation #AIinEducation #Entrepreneurship #FutureProof #MusicTech #AIRevolution #MusicIndustry #Innovation

    44 min

  4. Jun 9

    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 best version of themselves. Sylvestre argues for "AI plus human" rather than job elimination, and tells the story of how AvatarBuddy evolved from early research and prototypes to joining the OpenAI developer community in 2021, using teenagers for requirements and testing, and adopting curated "data vault" approaches (RAG) to improve results. AvatarBuddy provides managed AI-as-a-service, building and managing AI agents and advising clients, with tight controls on configuration. Sylvestre discusses her consulting process of AI opportunity mapping to identify root bottlenecks, with examples like reducing email overload by capturing requirements, creating digital twins for executive review, accelerating marketing work, and shortening month-end close, while warning that AI built without software engineering understanding can amplify security risks. The episode ends by affirming how AI not only allows for efficiency, but support for unique working styles that boosts morale. 00:00 Cold Open 00:34 Meet Stephanie 00:53 AI Before It Was Cool 03:04 Choosing AI Over VR 04:40 AvatarBuddy Origin Story 05:37 Early Prototypes and Testing 07:34 OpenAI Access and Launch 09:41 Data Vault Approach 10:33 What AvatarBuddy Does 11:48 AI Configuration Risks 12:11 Why AI Needs Software Basics 16:53 How Engagements Start 17:54 Opportunity Mapping Session 19:11 Prepared vs Unprepared Clients 22:38 CEO Bottleneck Twin 24:10 Blank Page Productivity 27:31 Scaling With Automation 28:57 Measurable Process Gains 32:10 Service Plus Product 32:57 IP As Differentiator 35:14 Personalized Agents Moat 39:37 Work Your Own Way 40:23 Find Stephanie Online 41:13 Podcast Wrap Up Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Stephanie Sylvestre: https://www.linkedin.com/in/stephanie-a-sylvestre/  Avatar Buddy: https://avatarbuddy.ai  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #Automation #FutureOfWork #AvatarBuddy #EliminateBottlenecks #AI #AIAssistedProgramming #AIRevolution #AIAndBusiness #AIAdvisory #BusinessOptimization #RemoveBottlenecksNotPeople #AIInsights

    42 min

  5. Jun 2

    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 AI heavily, including a senior engineer who surprised Brad by running agents overnight to automatically perform fast, high-quality GitHub PR code reviews via a webhook-driven harness. The engineer built an opinionated, RAG-backed "world-class code review" skill set that pulls new PRs from selected repos, reviews them with defined criteria, and posts comments, highlighting the need to articulate engineering judgment rather than relying on gut feel. They explore how models and agent frameworks are becoming commoditized, making the key differentiator the ability to assemble components and codify professional, reusable skills. The conversation turns to how teams should integrate AI into the SDLC, balancing experimentation with a shared, periodically updated "long-term support" approach and quality gates, plus examples like agents generating test coverage and proposing fixes for failing tests. 00:00 Cold OPen 00:25 Podcast Intro And Banter 01:09 Mind Blown By AI Team 03:25 Overnight Agent Code Reviews 06:02 Make Your Opinions Clear 09:05 Models Vs Frameworks 12:32 Standardizing Team AI Use 14:43 LTS For Agent Workflows 15:51 Automate Repeated Tasks 21:52 SDLC First AI Second 25:04 Quality Gates And Automation 28:27 Agents For Tests And Bugs 30:55 Future Of Engineering Taste 32:40 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 #EngineeringExcellence #AIInnovation #TechInnovation #FutureOfWork #AIDriven #AIAssistedProgramming #AIAssistedCoding #AIProgramming #AICoding #SDLC #ADLC

    33 min

  6. May 27

    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 SaaS, enabling more bespoke software for underserved SMBs and vertical niches. They debate practical examples like a plumber-specific CRM versus highly custom workflows for a regional law firm, including concerns about long-term maintenance, fragmentation, and risk. Brad contrasts "overnight magic" agent claims with what he sees in fractional CTO work: teams using AI within disciplined engineering practices and quality gates to deliver far more output, though not fully autonomous "dark factories" yet. They explore Scott's hands-on Gas Town workshop experience building a fantasy football app with multiple agents, noting orchestration value, tooling immaturity, resource constraints, and confusing nomenclature. The episode ends with why experienced operators still dismiss AI for production code and whether agent frameworks will be custom-built or marketplace-driven.   00:00 Cold Open 00:14 Show Intro and Hosts 00:58 Viral LinkedIn Post Read 03:28 "Agree... Sort Of" Nuance 04:40 Plumber CRM Example 08:36 Law Firm Workflow Doubts 11:37 Engineering Reality Check 14:29 Gas Town Workshop Demo 17:34 Factory Setup and Risks 20:28 Why Leaders Still Doubt AI 22:26 AI Naysayers 24:10 Massive PRs 27:42 Monorepo Momentum 29:07 Engineering Joy 31:10 AI Mistakes 33:19 Agent Personas 37:04 Agent Marketplace 38:54 K Shaped Future 41:15 Trust But Verify 42:30 Wrap Up 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 #AIRevolution #AIAgents #AIAssistedCoding #AIAssisstedProgramming #BespokeSoftware #GasTown #TechInnovation #FutureTech #DigitalTransformation #TechLeadership #CTOInsights #TechTrends

    43 min

  7. May 19

    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 SpecKit because it produced "too many words," alongside Scott's example of accepting a 60,000-line pull request by reviewing the spec instead of the code. They reflect on how product owners often can't define what they want until they see it, and how software work is usually clarified through ongoing back-and-forth dialogue. SpecKit surfaces hidden ambiguity by generating questions product owners hadn't considered, changing what used to become ad hoc decisions, bugs, or debt. They argue speed enables tighter iteration, but also pressures product to "know what they want," raising job-impact fears for engineers and possibly product managers too. Their conversation prompts ideas for training, collaborative workflows, and even self-design—tempered by the continued need for standardization and cross-functional expertise. The episode ends with the hosts reflecting on buisness ideas that never came to pass, and affirming that now value comes down to how well the problem can be described. 00:00 Cold Open 01:18 Product Is The Hard Part 02:26 Fast Teams Meet Specs 04:34 Too Many Words Pushback 05:10 Review The Spec Not Code 08:00 Coder To Reviewer Shift 10:20 Why POs Avoid Specificity 13:01 Surfacing Ambiguity Shock 17:43 Two Hour Sprint Loop 19:35 Jobs Changing Anxiety 23:39 Problem Versus Solution Trap 25:56 Vibe Tools And Self Design 26:49 Real Estate CRM Anecdote 28:28 AI Rewrites Software Economics 29:31 Self Design Simple Specs 31:00 When Standards Matter 32:23 Training Product Owners 36:05 Jobs Converge Under AI 37:49 Three Pane Spec IDE 40:40 AI Comes For PMs 44:29 Founder Moats And Copies 46:24 Missed Spotify Moment 48:19 RealNetworks Almost Made YouTube 51:36 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 #SpecKit #SpecDrivenDevelopment #ProductManagement #AI #ProductOwners #CodeReview #QualityGates #IterativeProcess #UserStories #AIAssistedCoding #Spec

    53 min

  8. May 12

    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 teams through highly technical transformations in fintech and crypto, including major infrastructure migrations. They discuss whether different kinds of change require different leadership approaches, emphasizing that change management is fundamentally about people. They discuss how fear makes change harder, so leaders must create psychological safety by providing "air cover" and managing messaging up and down. Adam notes that good managers must handle hard conversations like layoffs and performance issues with empathy while recognizing these outcomes aren't always personal decisions. He offers advice for engineers moving into management, including a tongue-in-cheek analogy that managers "test in production," and describes a challenging EC2-to-Kubernetes migration where success required strong technical credibility, hands-on help, and attention to team psychology. Adam and Brad compare blameless vs egoless retrospectives, discuss leaders defending engineers behind the scenes, and highlight the need for real remediation like error budgets or vendor changes. The conversation closes on AI as a fundamental industry shift, debate over the loss of hand-crafted coding vs enduring need for problem understanding, concerns about the junior-to-senior pipeline if entry roles disappear, decision fatigue from AI agents, and optimism about smaller teams producing better products with fewer bugs. 00:00 Cold Open 00:31 Podcast Intro Guest 02:24 Change Management Basics 03:49 Defining "Air Cover" 06:50 Hard People Decisions 10:19 Managers Test In Prod 13:38 Big Cloud Migration 17:34 Hands On Migration Help 21:04 Failure Friendly Culture 23:41 Blameless vs Egoless Retros Debate 28:56 Managing Up After Outages 30:19 Accountability And Error Budgets 31:38 Vendor Failures And Remediation 33:53 AI Adoption And Resistance 34:44 Craft Versus Assembly Line 37:52 AI As Mid Level Engineer 41:17 Business Value For Juniors 45:11 Pipeline And Decision Fatigue 47:15 Specs Waterfall Meets Agile 49:07 Summary And Closing Thoughts Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  Dr. Adam Link: https://www.linkedin.com/in/adamlink/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AIRevolution #EngineeringCulture #ChangeManagement #LeadershipSkills #AIAssistedProgramming #AI #FinTech #Crypto #

    51 min
See All (76)

Trailers

Ratings & Reviews

5
out of 5
5 Ratings

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
    76
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    How Many CTOs

You Might Also Like