In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome tech entrepreneurs and avid scuba divers Justin Wolf and Joe Malek to share the story behind their generative AI–powered scuba guidebook and community app. What started as a side project became a test case for building fast with LLMs and pushing the boundaries of what small, technical founding teams can accomplish.

The conversation dives deep into the reality of building with GenAI: the tools, the tradeoffs, and the surprising limitations. Along the way, they explore philosophical questions about human creativity, AI collaboration, and how founders might rethink MVPs, product-market fit, and even team size in this new era. From fighter jets and PACT tests to the Wall Street Journal’s AI film experiment, this wide-ranging conversation connects code, culture, and curiosity in a way only How Many CTOs can.

• 00:00 Introduction and Welcome
• 00:36 Meet the Guests: Justin Wolf and Joe Malick
• 02:10 The Birth of a Scuba Diving App
• 03:22 Challenges and Solutions in App Development
• 06:27 Generative AI: A Double-Edged Sword
• 14:15 Technical Insights and AI Tools
• 21:29 Future Plans and Testing
• 26:43 The Importance of Control in Development
• 27:10 Automated Testing and PACT Tests
• 28:23 Wall Street Journal's AI Film Experiment
• 30:15 AI's Limitations and Human Creativity
• 32:06 AI in Fighter Jets: Human vs. Machine
• 33:55 The Future of AI and Human Intelligence
• 42:35 Generative AI and the Future of Work
• 47:12 The Role of Marketers in the Age of AI
• 50:18 Final Thoughts and Inspirations

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/
• Justin Wolf: https://www.linkedin.com/in/justinjwolf/
• Joe Malek: https://www.linkedin.com/in/jomalek/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #StartupTech #GenAI #Founders #SoloFounder #TwoGuysInAGarage #GenerativeAI #AIProductivity #StartupJourney #AIForStartups #LLM #FoundingWithAI #MVPStrategy #EarlyStageStartups #StartupLife #AIRevolution #FutureOfFounding #AIEngineer #BuildWithAI #FounderTools #TechInnovation #FromGarageToGPT

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub unpack one of the most debated questions in engineering leadership: Should engineering managers also serve as tech leads? They explore the organizational signals that indicate whether a team is ready to thrive with true cross-functional autonomy, and what can go wrong when roles and responsibilities blur. And of course, it wouldn’t be a How Many CTOs episode without a dive into AI-assisted coding—Scott and Brad share some recent wins (and fails) using tools like ChatGPT Codex.

• 00:00 Introduction and Host Greetings
• 00:53 Generative AI Tools Discussion
• 01:41 Challenges with AI and Coding
• 05:07 Onboarding New Engineers
• 10:03 Engineering Management Structures
• 25:02 Identifying Team Anti-Patterns
• 25:45 The Role of Psychological Safety
• 26:30 Product Manager's Influence
• 27:07 Balancing Centers of Gravity
• 27:59 Importance of a Tech Lead
• 28:37 Risks of Siloed Teams
• 32:14 Tech Lead vs. Engineering Manager
• 39:09 Prerequisites for Cross-Functional Teams
• 47:34 Core Beliefs and Team Structure
• 48:54 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/
• Mindsets That Shape Software Delivery Team Structures - https://medium.com/@rethinkyourunderstanding/mindsets-that-shape-software-delivery-team-structures-51d25f20638c

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #EngineeringManager #TechLead #ProductEngineering #OrgDesign #TeamStructure #TechLeadership #PeopleManagement #EngineeringCulture #StartupLeadership #EMvsTL #TeamDynamics #LeadershipTradeoffs #ScalingEngineering #OrgRoles #CollaborationMatters #ManagementVsLeadership

In this bonus episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub engage in a deep and insightful conversation with their guest Justin Kaufman about the transformative role of AI in software development. The discussion explores the potential of AI to revolutionize the industry by automating aspects of coding and problem-solving, potentially reducing the need for traditional software engineers in certain sectors. Justin shares his optimistic yet realistic views on how AI can significantly boost developer productivity and highlights real-world examples of AI-driven improvements in test coverage and coding efficiency. The episode also delves into the significance of organizing codebases for better AI integration and the advantages of using GraphQL to facilitate AI operations within applications. The conversation underscores the evolving nature of software engineering roles and the importance of embracing AI to stay relevant and succeed in the tech industry.

• 00:00 Introduction and Setting the Stage
• 01:07 The Future of Software Programming Jobs
• 02:48 AI's Limitations and Human Creativity
• 07:23 Real-World AI Success Stories
• 09:33 Embracing AI for Career Growth
• 12:22 Technical Insights and Best Practices
• 16:09 Conclusion and Episode 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/
• Justin Kaufman: https://www.linkedin.com/in/justinkaufman/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #AIEatsCode #SoftwareIsDead #WillAIBuildItBetter #EndOfProgramming #TechHotTakes #MonolithVsMicroservices #FastAndRecklessDev #AIShippedIt #GenerativeAI #BuildOrBeReplaced #StartupStack #FutureOfEngineering #HowManyCTOs #DumbSystemsSmartResults #GraphQL #TechProvocation #AISoftwareDevelopment #EngineeringDisruption #BuildFastDieYoung

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview special guest Justin Kaufman. Justin discusses his unique journey from working in health tech to founding the Mount Joy restaurant, where he’s implemented innovative tech solutions to enhance customer engagement. The conversation covers topics such as AI-assisted coding, the benefits and challenges of monolithic architecture, and the future of customer relationship management through modern LLMs. Justin also shares anecdotes about his time working with both hosts, revealing different aspects of their management styles.

• 00:00 Introduction
• 00:48 Guest Introduction: Justin Kaufman
• 01:29 Justin's Prepared List of Topics
• 03:49 Justin's Journey: From Health Tech to Chicken Shack
• 06:14 Innovating the Restaurant Experience
• 08:56 Building a Custom POS System
• 14:20 Leveraging AI for Personalization
• 17:41 The Power of Small Teams and AI Tools
• 28:05 Engaging Customers with Interactive Games
• 33:15 Evolution of Chatbots and CRM
• 34:09 Expanding Beyond Restaurants
• 35:17 Technical Challenges and Solutions
• 36:24 Monolith vs. Microservices
• 45:38 Serverless Architecture and Tech Debt
• 49:55 The Future of Small Teams and AI
• 57:05 Reflections on Management Styles
• 01:01:27 Conclusion and Farewell

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/
• Justin Kaufman: https://www.linkedin.com/in/justinkaufman/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #AI #LLM #OpenAI #ChatGPT #CRMSolutions #SmallBusinessTech #LangChain #RAG #AIEngineering #RealWorldAI #AIAgents #CustomGPTs #VectorDB #LLMStack #PromptEngineering #FullStackAI #AIInfra #AIUX #StartupEngineering #TechInnovation #AIForSMB #ChickenTech #GPTInTheWild #AppliedLLM #SemanticSearch #LocalBusinessTools 

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss with Dave Hardwick, the disruptive yet beneficial impact of AI on recruitment processes. They explore how AI tools are revolutionizing candidate searches for recruiters, but also touch upon the challenge of encountering fake profiles. The conversation further delves into whether hiring managers are considering AI proficiency in candidates and how engineers can leverage AI to advance their careers. The episode emphasizes the importance of curiosity, critical thinking, and adaptability in navigating the evolving landscape of AI in technology roles.

• 00:00 Introduction: The Evolving Landscape of AI
• 00:34 AI's Impact on Recruitment Tools
• 01:53 Challenges with Fake Profiles
• 04:37 AI in Candidate Assessment
• 08:40 Future of AI in Recruitment
• 10:17 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/
• Dave Hardwick: https://www.linkedin.com/in/dave-hardwick-4596a0/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Agile #TechDebt #OperationalExcellence #EngineeringCultureMatters #EmpoweredTeams #DevProcess #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #HyperGrowth #TechnicalRecruiting #HiringEngineers #RecruiterInsights #AIRecruiting #FakeProfiles #TechHiring #TalentSearch #AIinHiring #AIethics #CareerDevelopment #FutureOfWork #SoftwareCareers #EngineeringCareers #AIDisruption #RecruiterTips #InterviewingWithAI #AIReadiness

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome Dave Hardwick, a seasoned technical recruiter. Together, they explore the intricacies of recruiting engineering talent, the gaps between what CTOs think they want and what they actually hire, and the importance of clear job descriptions and scorecards in the hiring process. Dave shares insights on what makes a strong resume, the challenges of hiring for senior technical roles, and the significance of soft skills like resourcefulness and leverage in startup environments. This episode is a deep dive into effective recruiting strategies for engineering teams.

• 00:00 Introduction to the Podcast
• 01:04 Meet Dave Hardwick: Technical Recruiter
• 01:34 The Art of Recruiting: Insights and Challenges
• 05:54 Effective Interviewing and Scorecards
• 13:08 Crafting the Perfect Resume
• 20:45 The Unassuming Engineer's Journey
• 24:16 Common Resume Mistakes
• 25:13 Hiring for Startups: Values and Flexibility
• 25:34 The Realities of Startup Life
• 30:21 Resourcefulness and Leverage in Startups
• 31:29 Intentionality in Startups
• 32:53 Evaluating Engineering Managers and Directors
• 38:08 The Executive Mindset
• 40:08 Conclusion and Contact Information

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/
• Dave Hardwick: https://www.linkedin.com/in/dave-hardwick-4596a0/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Agile #TechDebt #OperationalExcellence #EngineeringCultureMatters #EmpoweredTeams #DevProcess #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #HyperGrowth #TechnicalRecruiting #HiringEngineers #EngineeringHiring #CTOHiring #RecruiterTips #ResumeAdvice #TechCareers #Scorecards #InterviewTips #StartupCulture #SoftSkillsMatter #TeamFit #HiringMistakes #StartupRecruiting #ExecutiveHiring

In this bonus episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into a conversation with Greg Conklin, exploring his experiences at two hypergrowth companies, Groupon and Dropbox. Greg shares insights on the unique cultural and technical strategies employed at both organizations during their rapid expansion phases. He discusses the challenges of technical debt, team building approaches, and the differing priorities at Groupon's distributed startup-like model versus Dropbox's cohesive, security-focused architecture. The episode also touches upon the role of senior engineering leadership in managing technical debt and optimizing engineering velocity across diverse teams.

• 00:00 Introduction: The Journey of Tech Debt
• 00:22 Exploring Hypergrowth at Dropbox and Groupon
• 01:25 Building Teams and Strategies
• 03:24 Cultural Differences and Technical Challenges
• 04:36 Platform and Ops Teams at Groupon vs Dropbox
• 07:41 Managing Technical Debt and Engineering Leadership
• 10:23 Conclusion and Farewell

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/
• Greg Conklin: https://www.linkedin.com/in/gregoryconklin/
• Greg's Blog: https://gregconklin.com/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Agile #TechDebt #OperationalExcellence #EngineeringCultureMatters #EmpoweredTeams #DevProcess #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #HyperGrowth #HyperGrowthEngineering #ScalingTech #PlatformEngineering #TechnicalStrategy #TechScalability #DistributedTeams #RapidGrowth #TechOrgDesign #GlobalEngineering #TechOps #AcquisitionStrategy #MultiTenantArchitecture #VelocityVsQuality #TechTradeoffs #EngineeringVelocity #SystemDesign #APILayer #InfrastructureStrategy #SaaSScaling

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by special guest Greg Conklin for a candid and insightful conversation on what it takes to build high-performing engineering teams.

Drawing from their shared time at the telemedicine startup 98point6, the trio unpacks hard-earned lessons around tech debt, operational excellence, and culture-first leadership. Topics include:

• Why setting guardrails for quality, performance, and reliability early pays dividends later.
• The real value of postmortems and RCA meetings (and how to make them stick).
• How overly strong culture filters can unintentionally suppress bravery and dissent.
• What startups should prioritize in their first few quarters to avoid painful rework.

Whether you’re scaling an early-stage team or trying to fix systemic issues in a mature org, this episode delivers practical frameworks and honest reflection from leaders who’ve been there.

• 00:00 Introduction and Welcome
• 00:46 Guest Introduction: Greg Conklin
• 02:05 Revisiting 98.6: Lessons Learned
• 03:27 Empowerment and Quality at 98.6
• 05:32 Challenges in Engineering Management
• 10:46 Operational Excellence and Technical Debt
• 24:25 Dropbox Postmortem Insights
• 27:14 Blameless vs. Egoless Retrospectives
• 30:51 Setting Early Standards in Startups
• 35:11 Challenges in Test Automation
• 38:49 Local Development and Ephemeral Environments
• 44:33 Concluding Thoughts on Engineering Leadership
• 47:15 Podcast 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/
• Greg Conklin: https://www.linkedin.com/in/gregoryconklin/
• Greg's Blog: https://gregconklin.com/

#TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Retrospectives #BlamelessRetrospectives #EgolessRetrospective #Agile #ContinuousImprovement #RootCauseAnalysis #FiveWhys #IncidentResponse #GrowthMindset #TeamTrust #BuildingTrust #SDLC #TechDebt #OperationalExcellence #Postmortems #SiteReliability #SLA #SystemReliability #IncidentManagement #EngineeringCultureMatters #EmpoweredTeams #EngineeringGuardrails #PsychologicalSafety #DevProcess #EngineeringStandards #ShiftLeft #StartupLeadership #EngineeringMaturity #ScalingEngineering #EngineeringOrgDesign #ProductEngineeringAlignment #CI_CD #DevEx #TestAutomation #Observability #BuildPipeline #LocalDevEnvironment

 

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub explore the art and impact of retrospectives in engineering teams. Drawing on their experiences in both software and high-stakes environments like mountain rescue, they discuss the value of retrospectives for continuous improvement, building trust, and uncovering root causes of both successes and failures. The conversation covers practical frameworks for running retros, the importance of psychological safety, and the challenges of accountability and follow-through. They also debate the strengths and limitations of the "five whys" technique and share real-world anecdotes about incident response, team culture, and the unique dynamics of remote work.

• 00:00 Introduction and Banter
• 00:28 Cocktails, Bathtub Drinks, and Whiskey
• 01:40 Welcome to the Episode: Retrospectives
• 02:05 Retrospectives in Agile and Mountain Rescue
• 04:11 The Overlap Between Debriefs in Rescue and Software
• 04:30 Core Values: "Get Better Every Day"
• 04:50 Growth Mindset and Team Improvement
• 05:00 Retros for Every Error?
• 06:40 The Value of Interrogating Successes
• 08:40 Types of Retrospectives: Sprint, Project, Incident
• 09:30 Practical Framework for Sprint Retros
• 14:25 Accountability and Tracking Retro Action Items
• 18:05 Handling Big, Complex Retro Outcomes
• 18:40 Real-World Example: Staging Environments and Edge Cases
• 21:40 Tech Debt, Investment, and Team Process
• 23:40 Building Trust for Effective Retros
• 25:43 Incident Retros: Blameless vs. Egoless
• 27:15 Tone, Timeline, Five Whys, and Root Cause Analysis
• 32:00 The Role of Incident Commander
• 33:15 The Five Whys
• 34:10 The Challenge of Branching Root Causes
• 37:44 Working Agreements, Action Items, and Continuous Improvement
• 39:14 Retros and a Culture of Trust
• 40:04 Building Trust on Remote Teams
• 41:14 Call to Action 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 #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #EngineeringProductivity #TeamVelocity #DevCulture #TeamCulture #EngineeringCulture #Retrospectives #BlamelessRetrospectives #EgolessRetrospective #Agile #ContinuousImprovement #RootCauseAnalysis #FiveWhys #IncidentResponse #GrowthMindset #TeamTrust #BuildingTrust #SDLC

In this bonus episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub sit down once again with technologist and philosopher John Helm, this time for a wide-ranging conversation about artificial intelligence, epistemology, and what it means to be human in an age of machines. John draws on his background in statistics and philosophy to frame AI through the lens of knowledge, reasoning, and moral agency.

The episode touches on the hype and promise of modern AI systems, explores the difference between correlation and understanding, and raises deep questions about consciousness, ethics, and whether general intelligence can exist without emotion. John even challenges the language we use to describe AI by grounding the conversation in ancient philosophical questions, the structure of scientific truth, and how humans conceptualize value and meaning.

• 00:00 Introduction: What Makes Us, Us
• 00:19 Diving into AI: Hype and Reality
• 01:03 Philosophical Insights: Knowledge and Understanding
• 03:00 AI and Human Understanding: Patterns and Predictions
• 05:19 Ethical Concerns and Human Morality
• 08:14 Concluding Thoughts: Ethics, Knowledge, and Governance
• 10:28 Outro: Follow 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/
• John Helm: https://www.linkedin.com/in/johnlhelm/

#TechPodcast #EngineeringPodcast #PodcastForDevs #HowManyCtos #Podcast #Ctos #Technology #Leadership #EngineeringLeadership #CtoPodcast #ArtificialIntelligence #AGI #MachineLearning #AIHypeCycle #AIPhilosophy #EthicsInAI #MoralMachines #ReasoningModels #Epistemology #KnowledgeAndTruth #HumanConsciousness #AIAndHumanity #GeneralIntelligence #CorrelationVsCausation #AIAlignment #PredictiveModels #PhilosophyOfAI