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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

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  • 24 episodes
  • weekly
  • Avg 47 min
  • English

Episodes 24

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  • S2 · E15
    April 21 · 48 min

    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

  • S2 · E14
    April 14 · 48 min

    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

  • S2 · E13
    April 7 · 32 min

    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

  • S2 · E12
    March 31 · 57 min

    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

Showing 21–24 of 24 episodes