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. 2D AGO

    Where Does the Alpha Flow?: Rethinking Software Value in the Age of AI

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a conversation Scott had with coworkers after discovering Confluence connected to Google Drive and Slack, raising questions about whether to rely on tools like Confluence or a generic layer like Claude to aggregate knowledge and enable agents. A colleague suggested "alpha flows to where building happens," prompting Scott to question whether he agrees, what engineers actually need from AI (clear specifications), and whether customer insights and business needs matter more than internal documents. The hosts explore different types of builders, how clean data becomes a differentiator once tooling is ubiquitous, and define "dirty" or stale data through examples of conflicting documentation and misleading dashboards. Brad argues that as the building gets easier, the value shifts to market understanding and especially to the spec, not the code, while both conclude that ultimately, advantage comes from strong guardrails for correctness and value. 00:00 Cold Open 00:26 Podcast Setup And Topic 00:52 Confluence AI Discovery 02:32 Alpha Flows To Builders 03:51 Six Big Questions 07:36 Long View On Differentiation 09:12 Specs And Translation Layer 13:15 Design Levels And Personas 17:24 Moats Disappear In AI Era 20:41 Security And Exploit Agents 21:54 Mythos And Free Code 22:33 Specifying What Matters 23:23 Agent Strip Mining Products 24:42 Dirty Data In Knowledge 28:30 Stale Docs And Deletion 30:31 Bias And Interpretation 32:08 Ready Aim Shoot Debate 34:49 Specs QA And Guardrails 37:30 Where Value Really Flows 39:29 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 #AITransformation #DataDriven #Innovation #Automation #DisruptiveTechnology #AIFuture #AITrends #InnovationInAI #AIForBusiness #TechRevolution #AIInsights #AIRevolution #EthicalAI #AIAssistedCoding

    41 min

  2. APR 21

    Product-Market Fit and Pragmatic AI: Insight from RevenueCat's CTO Miguel Carranza

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" interview Miguel Carranza Spanish-born co-founder/CTO of RevenueCat, who describes discovering subscription billing pain while building the Elevate app and turning that hard, "boring" problem into a YC-backed business. He explains RevenueCat's scale (billions of API requests/day) and the resulting priorities: product-market fit, reliability/security, and sustaining culture in a fully remote team across 27 countries. Scott and Brad commiserate with Miguel about avoiding platitudes in company values by grounding them in specific principles—always be shipping, customer obsession, ownership, balance, pragmatism, and healthy paranoia—reinforced through public shout-outs and performance expectations, plus examples of choosing customer support over strict entitlement. The discussion covers AI's tailwinds, internal adoption, standardizing workflows, a rule that PR authors must understand every line, and why auto-generating PRs from bug reports still requires context and triage. 00:00 Cold Open 00:24 Meet Miguel Carranza 01:06 From Spain to Startups 02:28 Subscription Billing Pain 04:50 Building RevenueCat 09:49 Scaling and Reliability 11:16 Culture as a CTO Job 14:31 Defining Company Values 16:56 Pragmatism and Paranoia 19:16 Making Values Real 23:24 Values Over Talent 24:39 Daily Value Decisions 24:58 Slack Support Dilemma 26:28 Pragmatic Customer Fixes 28:38 Culture Fit Reality 30:02 AI Era Product Fit 35:06 Organic AI Adoption 37:28 AI Coding Guardrails 40:49 Bug To PR Debate 44:48 Engineering Identity Shift 47:30 Closing Thank Yous And Plugs   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/  Miguel Carranza: https://www.linkedin.com/in/miguelcarranza/  RevenueCat: https://www.revenuecat.com/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #SoftwareDevelopment #StartupSuccess #StartupCulture #TechEntrepreneurship #Innovation #AI #AIRevolution #AIAssistedProgramming #AICoding #RevenueCat

    49 min

  3. APR 14

    The Most Optimized Blue: Differences Between UI and User Experience Design with Nick Cawthon

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub talk with Nick Cawthon of gauge.io, who shares highlights from RSA 2026 and his career designing UX for InfoSec/SecOps/DevOps tools. Nick argues that modern dashboards increasingly look the same, so strategists and researchers must find the nuances by designing for the human factor. He explains how research-driven UX reduces fatigue and errors caused by behaviors like endless scrolling, swivel-chair context switching, and inconsistent layouts. The group discusses how B2B security users want speed and clarity rather than "stickiness," why UI is often confused with UX, and how product-led vs engineering-led cultures affect outcomes. They debate whether agent-led/AI companies truly understand UX, why poor UX persists (strategy, impatience, capitalism), the role of humility, what's measurable in UX, and whether cheaper engineering will shift investment toward design.   00:00 Cold Open 00:30 Podcast Intro Guest 01:09 RSA Conference Context 02:29 Design Shift Since iPhone 03:53 Human Factor in SecOps 04:40 Research First UX 04:54 Scrolling And Swivel Chair Fatigue 09:59 Consistency Notifications Workflow 11:14 B2B Speed Over Stickiness 12:56 Why We Repeat Mistakes 14:09 UX vs UI Value 18:23 Engineering Product Design Dynamics 20:25 AI Agents Deployed Engineers 22:33 Design Strategy Takes Discipline And Patience 25:47 Why Bad UX Persists 29:18 Measuring Experience 30:07 Title Suggestion 32:46 AI Chat Interfaces 36:49 Patterns and Commoditized Design 38:46 Code Gets Cheaper 41:53 Service Design Matters 43:19 Everyone Builds Now 46:02 Wrap Up and Links   Resources and hashtags to the end How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  Nick Cawthon: https://www.linkedin.com/in/nickcawthon-ux-digital-agency-product-design-leadership/  Gauge.io: https://gauge.io/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #InfoSec #SecOps #UX #UI #UXvsUI #UXDesign #UserExperience #DesigntoSucceed #UXStrategy #TechInnovation #AI #IndustryInsights #HumanFactor

    48 min

  4. APR 7

    Balancing Innovation and Safety: CTOs Check-In About AI Evolution

    In this "What's on your mind?" episode of the "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how non-engineers using AI tools are increasing risk, with Brad concerned about security amid recent supply-chain attacks. Brad shares how an AI agent setting up a React Native scaffold generated and transmitted database passwords and API keys in clear text, raising fears that LLM logs could expose secrets if vendors are hacked. Scott describes a false alarm involving Lovable and Snowflake access, and wrestles with conflicting company values—moving fast vs. protecting customer data. They reference Robert Siciliano's ideas on fatalism and trust and debate whether SOC 2 can become simply a checkbox. Brad also shares productivity loss without automated CI/CD and ephemeral environments, and the hosts question why containers still feel hard after years of innovation. Scott worries about AI's impact on young adults and entry-level jobs, mentions a voice tool called Whisper Flow, and the episode ends with a reflection on niche trade skills, such as guitar repair.   00:59 Supply Chain LLM Exploit 03:23 Secrets Leaking via Agents 06:17 Lovable Data Scare 07:08 Move Fast vs Secure 07:57 One Way Door Security 12:59 Compliance vs Real Security 14:19 SOC 2 Box Checking 16:00 Frameworks Save the Day 16:32 Next Topic CICD Automation 18:27 Why CICD Is Hard 19:30 Startups Skip the Setup 21:05 Kids Facing AI Uncertainty 24:18 Career Pipeline Problem 25:07 Jobs Move Down Stack 27:00 Fewer Harder Tech Jobs 29:21 Punk Rock Amp Repair Storytime 31:17 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 #AIAssisstedProgramming #AIAssisstedCoding #AIProgramming #AIRisks #Cybersecurity #DataSecurity #CyberThreats #TechSecurity #DigitalSafety #SecureTech #CyberResilience #MachineLearning

    32 min

  5. MAR 31

    Engaging Employees in Security Appreciation with Robert Siciliano

    In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub welcomes Boston-raised security speaker Robert Siciliano, who traces his path into security from early experiences with crime, teaching physical self-defense, and being hacked in the mid-1990s. Robert argues that most corporate security training is compliance-driven "security theater" focused on phishing, creating security fatigue while leaving human behavior unchanged. He advocates "security appreciation," making security personal and using interactive dialogue rather than monologue. He explains the "human blind spot," a biological impulse to trust, plus denial and cultural myths that equate security with paranoia. He urges leaders to live security as a lifestyle, empathizes with the C-suite through relatable family stories, addresses digital literacy gaps, and leverages compelling AI/deepfake risks—illustrated by Brad's deepfake-like fraud example—to drive lasting behavior change. 00:23 Meet Robert Siciliano 01:53 Streets to Security 02:50 First Hack Wakeup 05:32 Why Training Fails 07:24 Compliance Fatigue 07:59 Make It Personal 09:11 Interactive Reality Check 12:34 Fatalism and the Human Blind Spot 15:59 Home Security Parallels 20:17 Security vs Paranoia 25:23 Denial and Avoidance 26:42 Attackers Use Heuristics 28:02 Good People vs Sociopaths 30:22 Strategic Human Firewall 31:48 Awareness Versus Appreciation 33:58 Tone At The Top 36:27 Make It Personal For Leaders 38:40 AI Deepfakes Raise Stakes 44:10 Digital Literacy Crisis 49:59 Empathy And Dialogue Training 54:53 Wrap Up Resources: How Many CTOs Pod: https://howmanyctospod.com Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/  Robert Siciliano: https://www.linkedin.com/in/robertsiciliano/ Protect Now: https://protectnowllc.com/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #CyberSecurity #SecurityAwareness #SecurityInnovation #DigitalStrategy #CyberAwareness #CyberRisk #DataProtection #RiskManagement #SecurityCultur #SafetyFirst #SecurityMatters #PrivacyProtection #TheStrategicHumanFirewall #AI #TheHumanBlindspot #Deepfakes #SecurityAppreciation #KitchenTableEffect #DigitalLiteracy

    58 min

  6. MAR 24

    Building Trust with AI: David Espindola on the Path Forward

    In this episode of "How Many CTOs Does It Take?" podcast, Scott Porad hosts solo and interviews technologist David Espindola about AI. Espindola explains his path from engineer at fast-growing Silicon Valley companies to 10 years at Oracle implementing ERP/CRM for Fortune 500 clients, then a decade as a CIO, and now founder of Brainyus, focused on helping people thrive amid rapid AI-driven change. Espindola outlines what aspiring CIOs must learn: leadership, business and industry knowledge, strategy, communication, and enough technical breadth to hold intelligent conversations, including building infrastructure and security experience through teams and vendors. Scott shares his "battlefield promotion" into infrastructure. Espindola describes Brainyus's media/education, advisory, and technology lab pillars, including Zena, his AI podcast co-host, emphasizing trust through strong context and instructions while using existing LLMs. They discuss privacy risks, small vs large models, Zena's podcast origins, and three-way conversation limits. They also cover themes from Espindola's book about disruption, job displacement, and entry-level pipelines, potential environmental and healthcare benefits, and interface limitations. The episode ends with a reflection on how AI has been the most rapid transformation in the industry seen yet.   00:00 Cold Open 00:21 Meet David Espindola 01:20 From Engineer to CIO 03:23 Skills of a CIO 05:27 Scott's Battlefield Promotion 07:48 Introducing Brainyus 09:59 Zena the AI Co Host 11:05 Building Trust in AI 12:26 Models Privacy and SLMs 15:31 How the AI Podcast Works 19:02 Voice AI Gets Real 20:57 AI Change Chasm 22:14 Jobs and Reinvention 25:19 Entry Level Pipeline 29:07 AI for Climate Solutions 31:39 Zena Podcast Lessons 34:52 Fastest Disruption Yet 37:41 Emotion Sensing Future 39:01 Where to Find David 39:36 Show Credits and Outro   Resources: How Many CTOs Pod: https://howmanyctospod.com Scott Porad: https://www.linkedin.com/in/scottporad/  David Espindola: https://www.linkedin.com/in/davidespindola/ David's Website: https://davidespindola.com/ Conversations with Zena podcast: https://zena.brainyus.com/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #Brainyus #AIAssistant #AITrends #FutureOfWork #LLMs #AIInnovation #MachineLearning #ArtificialIntelligence #AIAndHumans

    40 min

  7. MAR 17

    Beyond Transcripts: Language Nuances and Audio Signals with Carter Huffman of Modulate

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub talk with Carter Huffman, CTO and co-founder of Modulate AI, about his path from machine learning work at NASA's Jet Propulsion Lab to building voice AI that understands conversations. Carter explains why moderation in gaming is hard because you don't want to ban players unfairly, and contrasts big foundation models with orchestrated ensembles of many tiny models that require high-quality, globally vetted data labeling. They discuss the nuance of classifying hate speech, expansion into detecting fraud and manipulation in delivery and call-center contexts, and monitoring misbehaving AI voice agents. The conversation covers why conversation is more than transcripts, possible therapeutic/telehealth uses of Modulate, analyzing data at a massive scale, and ambitions for audio generation using hierarchical edge-and-cloud approaches. The episode ends with a humorous anecdote about two factor authenticaiton failure.    00:00 Podcast Cold Open 00:48 Meet Carter Huffman 02:06 JPL Spacecraft Autonomy 04:18 From JPL to Audio AI 06:18 Why Audio Is Hard 07:44 Voice AI Use Cases 12:49 Tiny Models Orchestration 15:56 Data Labeling at Scale 17:17 Defining Toxic Behavior 18:58 Nuanced Language Moderation 20:04 Scaling Ensemble Models 21:39 GPU Crunch During Launch 22:29 Beyond Gaming Use Cases 26:03 AI Agents Gone Wrong 28:45 Telehealth and Diagnostics 30:26 Ambient Audio and Privacy 32:26 Edge Ensembles Everywhere 33:25 Audio Synthesis Ambitions 35:24 Latency Hierarchies Explained 38:10 Two Factor Key Fob Fiasco 39:14 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/  Carter Huffman: https://www.linkedin.com/in/carter-huffman-a9aba05b/  Modulate: https://www.modulate.ai/  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #VoiceTech #MachineLearning #MachineLearningModels #GamingIndustry #AIinnovation #Entrepreneurship #AIConversation #VoiceAssistant #LanguageModeration #GPU #LLMs #LargeLanguageModels

    41 min

  8. MAR 10

    Introducing the ADLC: The Agent Development Life Cycle

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub" open with Super Bowl reactions and a meme about non-fans describing plays, then pivot to the ai.com halftime ad, where heavy spending reportedly led to a site crash for a Claude wrapper. They discuss MCP servers and "Rent A Human," noting gig marketplace challenges like trust, KYC, and fake profiles, and compare MCP hype to Facebook integration in 2010. Brad highlights AI agents using MCP servers for observability as a major debugging unlock, prompting nostalgic ancedotes from Scott about Microsoft Log Parser and Ajax. In their discussion about the importance of branding tools, Scott and Brad coin "ADLC" (Agent Development Lifecycle) for integrating agents into existing SDLC/CICD with human merges. After a brief tangent about O'Reilly cover animals, Brad argues this approach beats skeptics and vibe coders while changing roles, pressuring product ideation, and reducing the need for separate QA via automated and browser-driven testing. 00:34 Podcast Kickoff Banter 02:03 Football Memes And Pet Peeves 05:17 Broadcast Tech And AI Ad Fail 07:55 Rent A Human MCP Debate 10:21 Marketplace Trust And Moats 14:15 Why Build An MCP Server 17:02 Branding Tech Like Ajax 20:42 Signal MCP For Agent Pings 22:03 MCP Naming Origins 23:41 Agents in the SDLC 25:25 Branding ADLC and SDD 26:50 O'Reilly Animal Brainstorm 28:06 Marketing a New Method 29:43 Three AI Developer Camps 31:15 Why Structure Beats Vibes 37:32 QA Testing with MCP 39:27 Operational Guardrails 41:01 ADLC Summary and Wrap 43:44 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 #AIRevolution #AIAssistedProgramming #AINews #SDLC #ADLC #MCP #Ajax #QA #QATesting #MCPservers

    44 min
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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
    67
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    How Many CTOs