How Many CTOs

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

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

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

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

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

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub compare Anthropic and OpenAI's distinct business strategies. While OpenAI takes a high-risk, expansive approach aiming for rapid growth, Anthropic focuses on a more disciplined, business-centric path, particularly targeting corporate customers and avoiding more expensive AI ventures like image and video generation. The conversation extends to thoughts on major tech players like Meta, Microsoft, and Google's positioning in the AI market. They delve into a variety of related topics including the announcement of Google's Flows, Apple's deal with Google Gemini for Siri, and Elon Grokipedia. They conclude with reflections on market movements, investment considerations, and a dose of nostalgia with a nod to Yahoo Pipes.

00:00 Introduction and Welcome 00:34 AI Business Check-In: Anthropic vs. OpenAI 02:10 Anthropic's Cautious Strategy 03:17 OpenAI's Aggressive Approach 05:29 Cursor's Bold Move 08:02 Startup Discipline and Investment Insights 13:04 Apple and Google's AI Strategies 16:38 Google Flows and AI Innovations 17:45 Elon Musk's Wikipedia and AI News 20:10 Conclusion and Wrap-Up

Links

• WSJ: Why Anthropic is On Track to Beat OpenAI to a Profit: https://www.wsj.com/podcasts/whats-news/why-anthropic-is-on-track-to-beat-openai-to-a-profit/9838a414-9082-4a04-9138-9fb390abea2b

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 #AIBusinessStrategies #Anthropic #OpenAI #AIRevolution #AIInsights #TechNews #AINews #AIUpdates

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub delve into Scott's recent meeting with AWS. They discuss the concept of vendors supporting their clients, weighing potential benefits against risks like vendor lock-in and misaligned solutions. The conversation also touches on Scott's old blog 'The Luddite CTO.' They offer practical advice for engineering leaders on framing needs as problems to leverage vendor support effectively, rather than over-functioning or over-committing resources.

00:00 Introduction and Episode Kickoff 00:45 Introducing the Topic: Vendor Support 02:29 AWS's Customer Success Philosophy 03:28 Meeting Breakdown: Challenges and Discussions 05:54 Concerns and Reflections on Vendor Solutions 16:42 Advice for CTOs: Engaging with Vendors 22:53 The Luddite CTO: A Blast from the Past 24:32 The Risks of Cutting-Edge Technology 28:28 Vendor Lock-In: A Real Concern? 33:05 Navigating Vendor Relationships 40:30 Final Thoughts and Farewells

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 #VendorManagement #VendorPartnership #TechInsights #TechSolutions

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the pervasive influence of AI, starting with a critical look at Apple's Siri and its struggles to keep up with competitors like ChatGPT. They explore the current state of AI and its varied impacts, from productivity boosts in small resource-strapped organizations to the political and societal implications of AI adoption. The discussion also touches on the potential for AI to do good for the world, highlighted by Scott's viral LinkedIn post seeking practical examples. They wrap up with thoughts on responsible AI use, efficiency versus innovation, and the potential benefits for smaller players in the tech landscape.

00:00 Introduction and Welcome 01:27 Apple Siri's Shortcomings 04:42 Public Perception of AI 07:01 Energy Concerns and Data Centers 14:50 Viral LinkedIn Post On AI Innovations 21:41 AI for Dummies: Simplifying Technology 23:58 AI Hackathon: Fostering Innovation 24:58 The AI Boom and Its Societal Impact 26:40 Productivity Gains: A Double-Edged Sword 32:49 The Need for Experts in the Age of AI 38:50 Final Thoughts and Future Plans

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 #AIUpdate #AIDebate #AIProgramming #Innovation #LinkedIn

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the critical importance of clear requirements in both hardware and software projects. Using the analogy of a home renovation project, they explore how detailed planning and frequent communication between builders and requesters can prevent costly mistakes and ensure customer satisfaction. They relate this to the software development world, emphasizing the need for ongoing dialogue between product managers and engineers to clarify assumptions and avoid misunderstandings. The hosts debate the pros and cons of Agile versus waterfall methodologies and stress the importance of engaging engineers early in the ideation process to harness their technical insights and achieve more efficient, high-quality outcomes. They conclude with reflections on fostering a collaborative culture that values clear communication and thorough planning.

00:00 Introduction and Welcome 00:55 The Kitchen Renovation Analogy 04:59 Drawing Parallels to Software Development 06:21 The Importance of Clear Requirements 19:04 Cultural Challenges in Engineering 31:05 Conclusion and Call to Action

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 #ProductManagement #Agile #ProductRequirements #ProjectRequirements

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the 2025 DORA Metrics Report on the state of AI-assisted software development. They discuss key findings such as the near-universal adoption of AI, its impact on productivity, and its role in software delivery instability. Brad and Scott also explore the attributes of high-performance teams and the importance of organizational maturity in leveraging AI effectively. They conclude with reflections on AI's probabilistic nature and its implications for real-world applications.

00:00 Introduction and Welcome 01:08 Dora Metrics and AI: An Overview 03:28 Key Findings from the Dora Report 05:24 AI's Impact on Software Delivery 07:08 Organizational Clusters and Performance 11:00 Foundational Practices for AI Success 13:50 Challenges and Anecdotes 19:32 Challenges in Version Control for Machine Learning Models 23:15 The Importance of Small Batches in Development 25:01 User-Centric Focus in AI Adoption 26:36 Organizational Maturity and AI Success 31:15 AI Usage Statistics and Insights 35:30 Cautionary AI Tales and Lessons 37:22 Conclusion and Podcast 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/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCTOs #Podcast #CTOs #CTOPodcast #ChiefTechnologyOfficer #Technology #Engineering #SoftwareDevelopment #SoftwareEngineering #TechLeadership #EngineeringLeadership #EngineeringCulture #TechDebates #AI #AIFuture #DORAMetrics #DORAStateofAIAssistedSoftwareDevelopment #AIAssistance #AISoftwareDevelopment #AISuccess #HowManyCTOsDoesItTake