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. 6D AGO

    Adapt or Fade: Interviewing for Developers in the Age of AI Assisted Coding

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub explore the evolving landscape of interviewing for programmer positions in the age of AI-assisted coding. They discuss the relevance of traditional leetcode questions, best practices for evaluating skills when interviewees may use AI, and the importance of higher-level thinking in interviews. The conversation covers interview techniques such as pair programming and code reviews, possible IP concerns, and whether interview questions are designed to catch engineers or just coders. They also share insights on designing effective interview loops, the kinds of interview questions Microsoft asks, and the implications of using AI models for specific tasks like spell checking. 00:00 Introduction and Welcome 00:53 Interviewing in the Age of AI 01:27 Best Practices for AI-Assisted Interviews 03:59 Evaluating Technical Skills and Projects 08:13 The Role of AI in Coding Projects 12:53 Pair Programming and Code Review 16:34 Challenges and Considerations 29:54 Concluding Thoughts 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 #AIinterviewing #HiringTrends #ArtificialIntelligence #AIAssistedCoding #AIAssistedInterviews #CodingInterviews #AIRevolution #FutureOfWork #AIinTech #AIAssistance #PairProgramming #CodeReviews #HiringPractices

    31 min

  2. FEB 10

    From Rave Promoter to SaaS Innovator: Revolutionizing Event Management with Ritesh Patel

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub sit down with Ritesh Patel, co-founder of Ticket Fairy. Ritesh shares his journey from coding and organizing raves to creating a powerful vertical SaaS platform tailored for the live events industry. Ticket Fairy aims to provide small event teams with the technological capabilities of much larger organizations. Ritesh discusses the platform's unique features, the challenges of scaling, and how AI and machine learning are revolutionizing their approach. The conversation also delves into the role of entrepreneurs in the tech industry and the future of SaaS products. 00:00 Introduction and Welcome 01:05 Understanding the Live Events Industry 02:21 The Challenges of Small Event Teams 05:28 Ritesh's Journey: From Coding to Event Production 11:32 Balancing Technical and Business Challenges 15:01 Handling Spikes and Scaling Issues 19:58 Incorporating AI into Event Management 23:29 AI Coding Agents Revolutionizing Front-End Development 25:14 Convincing Engineers to Embrace AI 31:31 Ensuring AI is a Force Multiplier, Not a Risk 33:28 Building a Global, Multi-Time Zone Engineering Team 35:09 AI Code Review Bots Enhancing Security 40:20 AI Empowering Solo Entrepreneurs 45:09 The Future of SaaS and Deep Industry Insights 47:29 Conclusion and Final 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/ Ritesh Patel: https://www.linkedin.com/in/riteshdpatel/  Ticket Fairy: https://www.ticketfairy.com/event-ticketing  #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #LiveEvents #Entrepreneurship #AI #AIIntegration #BusinessGrowth #TechInnovations #Startups #EventTech #SaaS #TicketFairy

    49 min

  3. FEB 3

    From the Dress Code to the Bottom Line: A CTO Business Primer

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the interplay between tech and business. Starting with comments about their own scruffiness and stories of wearing hats to interviews and fancy restaurants, they delve into how CTOs can effectively bridge the gap between technical teams and business stakeholders. They run through a crash course on economics, explaining concepts like unit economics, customer acquisition cost (CAC), and lifetime value (LTV), explaining the importance of speaking the language that non-technical counterparts can grasp, and touch on the role of AI in reducing operational costs. The episode offers practical advice for aspiring CTOs and an invitation for listeners to request a class on finance specifically tailored for technology leaders. 00:00 Introduction and Welcome 00:37 Fashion in the Tech Industry 02:11 Remote Work Culture 03:58 Interview Attire and Professionalism 07:10 The Importance of Code Switching for CTOs 11:12 Understanding Business Metrics for CTOs 12:08 Unit Economics Explained 19:44 The Role of AI in Business Efficiency 30:45 Conclusion and Class Opening   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 #TechFashion #StartupLife #AIRevolution #BusinessGrowth #BusinessPrimer

    32 min

  4. JAN 27

    The K-Shape of AI Development: Managing Digital Interns

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub yet again delve into the transformative impact of AI on software engineering. Brad shares his 2025 Cursor Year in Review, revealing his record 2.9 billion tokens used, prompting a discussion about the efficiency and cost of using AI tools. They discuss the emergence of a K-shaped economy in AI coding and what attributes lead to successful AI-assisted coding. They emphasize the importance of breaking down tasks, evaluating progress, and adopting a tech leader mindset. The hosts debate whether code quality still matters in a world dominated by AI-generated code and conclude with reflections on the rapid evolution of the software development landscape brought about by AI. 00:00 Introduction and Welcome 01:02 Spotify Wrapped and Token Usage 02:21 The Cost and Value of Tokens 06:01 Breaking Down Tasks for AI 08:54 Documentation and Context for AI 10:59 Managing AI Agents Like Interns 15:39 Challenges with AI Agents 20:11 Key Skills for Engineering Managers 20:43 Environmental Attributes in Engineering 21:34 The Importance of Code Quality 22:26 Swashbuckler Vibe in Engineering 24:51 AI's Impact on Software Engineering 27:17 Evaluating Code Quality with AI 35:31 The Role of Small PRs 37:29 The Future of AI in Software Development 38:18 Conclusion 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 #Cursor #AIAssistedCoding #AIAgents #AIProgramming #AIFuture #AIRevolution

    39 min

  5. JAN 20

    Setting the Tone: Building Trust Through Security

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the role of CTOs in setting a security-minded culture and provide real-life anecdotes of security breaches and incidents. The conversation covers critical frameworks like CIS, SOC 2, and tools like Vanta, Wiz, Drata, and AWS Security Hub. They emphasize the importance of incident response, continuous vulnerability management, and making security practices an effortless part of development workflows. The episode concludes by highlighting the urgency of adapting to new security challenges posed by AI and other technological advances. 00:00 Introduction and Episode Kickoff 01:05 The Role of the CTO in Security 04:40 Real-World Security Incidents 08:08 Incident Response and Security Culture 12:42 Frameworks and Best Practices 21:44 Human Factors in Security 25:34 Supply Chain Attacks 26:26 Best Practices for Software Inventory 27:23 Setting Priorities for Vulnerabilities 34:30 Automating Security Checks 36:08 Tools for Compliance and Security 40:48 The Importance of Trust in Security 49:15 Final Thoughts and Conclusion 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 #Security #SecurityIncidents #IncidentResponse #SecurityCulture #SoftwareSecurity #SupplyChainAttacks #SecurityChecks #ComplianceAndSecurity #AI #Vanta #Wiz #Drata #AWSSecurityHub #CIS #SOC2

    54 min

  6. JAN 13

    Rediscovering the Joy of Coding through AI with Paul Brown

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by Paul Brown to delve into the misplaced fears of AI supplanting engineers, highlighting instead its potential to enhance productivity. Paul shares his journey from skepticism about AI's capabilities to recognizing its strengths, drawing parallels to the historic shift from mainframes to personal computers. They discuss the importance of writing and critiquing implementation plans, effectively utilizing AI tools, and managing resistance to AI integration in engineering teams. The dialogue is rich with insights on evolving AI models and the future of AI in coding. 00:00 Introduction and Guest Welcome 00:50 Paul Brown's Journey at Salesforce 02:28 Exploring AI and Vibe Coding 04:44 AI as a New Computing Paradigm 06:55 Challenges and Learnings with AI 11:15 The Role of Engineering Managers with AI 16:10 Choosing the Right AI Tools 24:41 Embracing AI as a Tool for Amplification 25:54 Addressing Resistance to AI Adoption 26:07 Mandating AI in Teams: A Balanced Approach 27:54 AI's Role in Solving Complex Problems 31:50 Understanding Agentic-Friendly Models 36:34 Fun with AI: The Hacker News Game 41:10 Final Thoughts and Farewell   Resources: How Many CTOs Pod: https://howmanyctospod.com Paul Brown: https://www.linkedin.com/in/paulrbrown/  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 #ArtificialIntelligence #AICoding #AIProgramming #AIAssistedProgramming #EngineeringManagers #AITools #AIDebate

    43 min

  7. 12/23/2025

    Year In Review: How Many CTOs Does It Take To Finish A Season?

    In this special public service announcement episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub announce that they will be taking a two-week break for the holidays and will return with Season 2 on January 13th. They reflect on their first year, discussing the major themes like the challenges of tech debt, the evolving role of AI in software engineering, and the value of weekly conversations with other tech leaders. The episode also acknowledges the contributions of their producer, Saffron, and offers a heartfelt thank you to all listeners. 00:00 Introduction and Welcome 00:30 Public Service Announcement 01:32 Reflecting on the Year 01:56 Holiday Plans 04:51 Themes and Highlights of the Podcast 11:32 Acknowledgements and Conclusion   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 #EndOfSeason #TechReflections #SeasonFinale #AIRevolution #2025 #EndofYearInsights

    13 min

  8. 12/16/2025

    Turtles All The Way Down: AI Insights with Scott W. Bradley

    In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome guest Scott W. Bradley, Managing Partner at Facet Digital, to delve into the complexities and potential pitfalls of AI technology. With insights drawn from Bradley's provocative LinkedIn post abstraction and language, the discussion explores AI's rapid growth, the quality vs. speed debate in tech development, and the lessons we might learn from the growth of social media. The conversation probes whether AI is heading towards a Jurassic Park-like disaster, and what methods can be used to build AI that cares for humanity.   00:00 Introduction and Guest Welcome 01:17 Scott Bradley's Background and Role 02:45 LinkedIn Post Discussion 05:03 AI and Abstraction Layers 14:34 Capitalism and Quality in Tech 28:15 Social Media Impact Debate 31:42 Evaluating the Internet's Net Good 34:32 AI and the Future: Concerns and Predictions 36:02 AI Alignment and Human-Like Caring 40:22 Human Learning vs. AI Learning 43:12 System Thinking and AI 52:10 AI's Role in Coding and Product Management 58:25 Concluding Thoughts on AI   Resources: Scott W. Bradley: https://www.linkedin.com/in/scottwb69/  Facet Digital: https://facetdigital.com/  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 #ArtificialIntelligence #AICoding #AIDebate #AIAssistedProgramming #AIProgramming #Abstraction #TechLayers

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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
    57
  • Rating
    Clean
  • Copyright
    © 2025
  • Show Website
    How Many CTOs