How Many CTOs

Brad Hefta-Gaub & Scott Porad
  • 5.0 (5)
  • Technology
  • Updated Weekly

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. 4d ago

    Beyond Cost Reduction: AI in Revenue Generation and Innovation with Andy Boettcher

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Andy Boettcher, Chief Innovator of DoubleTrack, a boutique data and AI consultancy. Andy recounts his 33 years across systems, development, with 13 years in Salesforce, and how his career shifted into data/AI full-time after ChatGPT's 2022 release. The group compares manufacturing's precise cost estimation to software's people-driven unpredictability, then explores moving beyond AI for cost takeout toward top-line revenue lifts. Andy emphasizes mindset—curiosity, open-ended questions, and "always assuming you're wrong"—and argues resistant engineers will be replaced by those using AI. They discuss using AI as a peer, agentic workflows, real-time CX intelligence for renewals/upsell, ethics, and the need for human-in-the-middle quality gates, scoring rubrics, and trustworthy PR artifacts. 00:00 Cold Open 00:18 Meet the Guest Andy 02:15 Micro Estimating Story 04:17 Why Software Estimates Fail 05:55 DoubleTrack and AI Work 08:15 Revenue vs Cost Takeout 10:39 AI as Peer Partner 13:35 Curiosity New Mindset 17:30 Learning to Prompt Better 20:49 Agents and Orchestration 23:05 Managing Teams of Agents 25:09 Real Time CX Signals 27:09 Scraping The Corners 29:07 Ethics Of Live Upsell 30:17 Async Agents In Practice 34:47 Trust And AI Slop 40:29 Agent Driven Code Reviews 44:52 Rubrics And Quality Gates 48:24 Final Advice And 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/  Andy Boettcher: https://www.linkedin.com/in/andyboettcher/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #Innovation #Data #RevenueGeneration #MachineLearning #BusinessStrategy #DataAnalytics #BusinessGrowth

  2. Sep 1

    The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview 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 and prescriptions in retail settings. Jack explains Eyebot's kiosk experience in Walmart Vision Centers, including intake questions, visual acuity testing, touch-free refraction and glasses scanning, and remote review by licensed optometrists/ophthalmologists with prescriptions returned in under 15 minutes. He discusses navigating FDA regulation as a Class I medical device using risk assessment (FMEA), a quality management system, and traceability, and shares why venture capital helped fund regulated hardware R&D. The conversation also covers Eyebot's doctor portal and network, limits versus comprehensive eye exams, potential future screening as a Class II device, and the challenges and culture required to merge hardware and software development with over-the-air updates and manufacturing partners. 00:00 Podcast Cold Open 00:51 Eyebot Mission 02:04 Founders and Origin 04:43 Access Stories 07:19 FDA Basics 10:30 FMEA Risk Analysis 13:17 Quality Systems 15:43 Funding Realities 16:53 Walmart Kiosk Flow 20:29 Touch Free Design 23:50 Remote Doctor Network 26:57 When to Refer Out 27:48 Minotaur Care Model 28:48 Doctor Shortage Solution 33:38 Hardware Software Moat 35:05 Formlabs Playbook 38:46 Leasing and Upgrades 40:11 First Launch with Walmart 48:35 Suppliers and Scaling 49:52 Culture and Closing 51:53 Outro 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/  Jack Moldave: https://www.linkedin.com/in/jackmoldave/ Eyebot: https://www.eyebot.co/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIAssistedCoding #AIAssistedProgramming #AIProgramming #AICoding #VisionCare #Innovation #MedicalDevice #Eyebot #EngineeringExcellence #HardwareDevelopment #SoftwareIntegration #DigitalHealth #FutureOfHealth #RegulatoryChallenges #EngineerSpeak #TechSolutions #MedTech #HealthcareInnovation #VisionCareAccess #MedDevice #SoftwareHardwareBlend

  3. Aug 25

    Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a leadership conversation where three senior stakeholders wanted different outcomes from engineering: delivering faster, maximizing utilization, or delivering on time—highlighting unclear norms and expectations in the software delivery system. The hosts argue you can't optimize all three at once, note that maximum utilization is a poor goal (systems perform better below 100% utilization), and debate prioritizing speed versus schedule. Scott favors being on time with about 80% accuracy to avoid sandbagging and support business dependencies like launches, while Brad generally prioritizes going fast, especially in early-stage or learning-focused contexts, with "within reason" expectations. They add an unspoken distinction between innovation organizations and manufacturing organizations, and observe that projects often go off schedule due to unclear requirements, shifting scope, or faulty early assumptions. 00:00 Cold Open 01:04 Velocity Tradeoffs Debate 03:07 On Time 80 Percent Rule 03:56 Innovation Versus Manufacturing 05:03 Why Utilization Misleads 06:43 Stage Dependent Speed 09:32 Quality And Launch Systems 11:56 One Project Always Late 12:51 Why Projects Derail 14:41 Front Load The Hard Parts 15:50 Wrap Up 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 #Velocity #Productivity #Utility #ResourceManagement #GoFast #GoFastBreakThings #ProductManagement #SpeedVsAccuracy #InnovationCulture #Innovation #EfficientTeam #Efficiency

  4. Aug 18

    The Pace of Innovation: Systems Thinking for Faster Engineering

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 explore a meta-question: if non-engineering teams couldn't tell engineering to "go faster," what would they change to increase engineering throughput? Using AI as a lens, they argue the bottlenecks become: deciding what to build, keeping a prioritized "shovel-ready" backlog, and handling downstream constraints like training users, releases, and integrations. They emphasize learning feedback loops, including studying what went right, and discuss long-horizon thinking for durable platforms. The conversation touches on Spain's mail-based customer service requirement, balancing innovation vs basic fixes (TaskRabbit categories), intentional tech debt, and ideas from Eric Ries's book "Incorruptible," plus examples of enduring companies like Costco and century-long businesses. 00:00 Cold Open 00:31 Podcast Kickoff Banter 00:44 Mountain Adventure Recap 01:37 Sports Week Highlights 03:53 Change Management Systems 05:10 Elevator Norms and Rules 07:51 Meta Question On Speeding Up Engineering 09:56 Instant Code Bottlenecks 12:03 Shovel Ready Planning 14:29 Downstream Release Constraints 19:35 Build the Right Stuff 24:59 Learning Loops and Postmortems 28:01 Spain Side Quest 30:23 Stop Forcing Revenue Targets 34:01 Mission Metrics And 3M 39:42 Innovation Versus Basics 42:37 AI Changes Tech Debt Math 49:03 Think In Decades 53:38 Costco Mission And Hotdogs 56:00 Subscribe 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 #EngineeringInnovation #SystemsThinking #R&D #Innovation #ProductManagement #ResearchandDevelopment #BusinessStrategy

  5. Aug 11

    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

  6. Aug 4

    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

  7. Jul 28

    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

  8. Jul 21

    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

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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
    86
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    How Many CTOs

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