How Many CTOs

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a Pragmatic Engineer talk on the state of the tech industry in 2026, focusing on what changed and what hasn't. They argue this is a "golden age" of building software due to AI, while acknowledging current "creative destruction" that may ultimately make the industry leaner. Key changes include agentic software factories where people increasingly don't read code, and a shift toward open-weight models for cost and data-sovereignty reasons, including local/on-prem inference. They note core software fundamentals (system design, resilience, security, validation) and organizational friction (alignment, clear requirements) remain unchanged. They also explore remote work's evolution, speculate about smaller squads and team structures, and end by deferring "what broke" and "what's next" to a future episode. 00:00 Episode Teaser 00:26 Show Intro and Banter 01:28 Time Travel and Quantum Aside 02:49 Was Tech Better Five Years Ago 04:47 AI Tools Golden Age 06:53 Creative Destruction Now 07:59 Reverse Engineer Anything Debate 11:03 Remote Work Then And Now 13:31 Pragmatic Engineer Summary Setup 14:50 Agentic Factories and Open Models 17:47 Open Weights Local Inference 24:14 What Has Not Changed 26:19 Org Structure And Smaller Teams 31:47 Wrap Up and Next Episode Preview 32:24 Credits and Outro 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 #TechIndustry #AgenticSoftware #QuantumMechanics #RemoteWork #SystemDesign #OrganizationalFriction #CreativeDestruction #FutureOfTech

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview software pioneer Kent Beck about his background (JUnit, test-driven development, extreme programming, Agile Manifesto, and his book "Tidy First?") and his current focus on "augmented development" with AI, which he calls a "genie." Beck argues that while AI shortens the build–feedback loop, it can also remove productive struggle that builds competence, agency, and flow, leaving developers exhausted and hollow. He critiques the "agent" metaphor, long tool latencies, and productivity measured as more code, proposing tools optimized for sub-second feedback, smaller safe increments, and even pushing changes to production thousands of times a day. Beck predicts programming demand will rise (Jevons Paradox), but warns mid-level "paycheck" developers must adapt. He advises leaders to use the tools themselves, build trust, and adopt via the technology adoption curve rather than mandates and layoffs. 00:00 Cold Open 00:22 Meet Kent Beck 04:31 Early Computing Origins 07:49 XP and AI Shift 11:29 Augmented Development Feel 13:06 Struggle Builds Competence 17:18 Beyond Agents Metaphor 20:39 Toil Versus Struggle 25:03 Flow and Feedback Loops 27:38 Amanuensis Junior Programmer 29:52 Manager Mode Reality 32:54 Optimize for One Second 36:35 Tech Cycles And Humans 41:01 Jobs And Jevons Paradox 46:56 Rethinking Productivity 52:15 Limbo Micro Deployments 56:01 Tool Seeds Sharing 59:34 Debugger Joy And TDD 01:02:19 Leading Adoption With Trust 01:08:57 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/  Kent Beck: https://kentbeck.com/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #AIRevolution #ExtremeProgramming #AgileManifesto #KentBeck #TechPioneers #FutureOfCoding #AIConversations #CodingCommunity #AIChallenges #HumanSideOfTech  

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss 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, minor cleanup issues, and why periodic region moves can serve as valuable "hygiene" to relearn and document complex systems while advancing disaster recovery and business continuity. They then explain tabletop exercises as structured incident-response drills designed to uncover gaps in process and documentation, sharing scenario ideas like data deletion, token leaks, cloud outages, ransomware, and internal actors, including an embezzlement case where the perpetrator joined incident response. The conversation touches on an alleged AI sandbox escape involving Hugging Face, then debates claims that "unit tests are dead," arguing AI makes end-to-end testing easier but unit, integration, contract, and mutation testing remain important—especially for edge cases and dependency failures—and that agents can now generate extensive test coverage.   00:00 Cold Open Banter 00:35 Light Bulb Struggles 01:12 TaskRabbit Region Move 05:23 Tabletop Exercises Explained 10:06 Designing Scenarios 13:37 Insider Threat Tabletop 16:51 AI Sandbox Escape Story 21:19 Unit Tests Are Dead 25:16 Why E2E Misses Edge Cases 28:30 Mutation Testing Explained 31:25 Integration Tests Basics 33:23 Contract and API Testing 38:27 Third Party Outage Example 41:55 Golden Age of Validation 43:59 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 #AWS #AWSMigration #DisasterRecovery #TabletopDrills #TabletopExercises #UnitTesting #EndToEndTesting #APITesting #Microservices #IncidentResponse #UnitTestsAreDead #UnitTestsAren'tDead #TestingStrategies #AIStories

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring leaders to disrupt old stabilizing practices. They explore concerns that AI lowers the barrier for others to change systems, increasing accountability, on-call risk, and architectural drift—problems that existed pre-AI but are now intensified. Their proposed response is to strengthen the software factory/SDLC with non-human, deterministic guardrails: robust automated tests, CI/CD quality gates, mutation testing, and better observability, rather than human gatekeeping or fiefdoms. They share examples of risky AI agent behavior (attempting to access credentials to reorder Jira tickets) and real-world harm from AI claim adjudication pilots, concluding that best practices are now the floor and that engineers who build quality gates become more valuable. 00:00 Cold Open 01:04 AI Fear in Engineering 02:00 Adaptive Leadership Moment 03:55 Software Factory Mindset 06:10 Fear of Accountability 08:09 Old Problem New Pressure 11:58 Non Human Quality Gates 13:41 Scaling Creates Fiefdoms 16:34 Architecture Agent Example 20:26 Apocolyptic AI Concerns 23:51 AI in Medicare Risks 32:29 Best Practices Are Floor 33:41 Wrap Up and Subscribe 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 #SoftwareFactory #AIChallenges #EngineeringManagement #AdaptiveLeadership #QualityGates #TechTalkingPoints #InnovationStrategy #LeadershipInsights #TechInnovation #AIThreat #AIFear #AIInTech

In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub 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 in 1994, and now serves as CTO at ProLegal, a legal services startup. Frank describes modernizing an old Act! database into a custom CRM, launching ProLegal Suite, and building systems that integrate with Uber and Lyft to schedule client rides on a lien. He explains how ProLegal uses AI to analyze case documents and train models on company-specific context, while keeping humans in the loop and reviewing AI-generated code. The conversation focuses on simplifying technology for non-technical users, the importance of shared terminology, troubleshooting and telemetry, and advice for CTOs on communicating clearly without acronyms.   00:00 Cold Open 00:41 Meet Frank Bravo 01:28 From Newsrooms to Startups 05:01 Building ProLegal Tech 08:18 AI in Legal Funding 12:04 Translating Tech for Humans 17:34 Choosing the Right Solution 18:41 Picking Podcast Topics with AI 21:58 Trust and Tech Backlash 26:01 How Fast Tech Changed 28:09 Phones as Invisible Tech 29:30 Wi-Fi vs Internet Confusion 32:30 Wired Beats Wireless 33:13 Buffering and Brand Names 34:33 Explaining Tech Simply 38:28 Empathy Through Support 41:49 AI as a Thought Partner 43:35 Telemetry for Troubleshooting 46:21 Career Through Line 48:50 Where to Find Frank 49:39 Show Credits and Outro Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  Frank Bravo: https://www.linkedin.com/in/fabravo/  Your Tech Makeover Podcast: https://www.yourtechmakeover.com/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #LegalTech #TechSimplified #AIInsights #ProLegal #InnovativeTech #BridgingTech #FrankBravo #Telemetry #TechBacklash #Trust #Troubleshooting