How Many CTOs
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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Design in the Age of AI: Craft, Tools, and the Future of Creativity
08/05/2025
Design in the Age of AI: Craft, Tools, and the Future of Creativity
In this episode of podcast, hosts and welcome design veteran for a deep dive into the shifting world of product design in the AI era. With over two decades of experience across corporate and freelance roles, Vince unpacks how design tools, workflows, and creative expectations have evolved—from Photoshop to Figma, from static mocks to design systems. They explore the unique challenges of designing for connected TV platforms, the rise (and friction) of standardization in design systems, and how AI is both a productivity multiplier and a creative constraint. Vince brings a designer’s perspective to questions many engineering leaders are now asking: How much of design can AI automate? Where does human craft still shine? And what does all this mean for the next generation of junior designers? This episode is a must-listen for CTOs, product leaders, and anyone navigating the intersection of design, technology, and artificial intelligence. 00:00 Introduction and Welcome 01:00 Guest Introduction: Vince's Journey in Design 02:33 The Evolution of Connected TV 05:15 Challenges in Design Standardization 10:07 The Role of AI in Design 20:29 Exploring Figma and Design Tools 28:17 Retrofitting Design Systems 28:55 Open Source Design Systems 30:12 AI and Design Systems 31:42 The Role of AI in Prototyping 36:16 AI's Creative Limitations 39:24 Ethical Implications of AI in Design 43:54 Challenges with AI in Visual Design 53:08 Future of AI in Design 54:15 Conclusion and Podcast Outro Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: Vince Dean: #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #DesignPodcast #ProductDesign #DesignLeadership #AIinDesign #DesignSystems #Figma #ConnectedTVDesign #UXDesign #UIDesign #EngineeringPodcast #HumanCenteredDesign #GenerativeAI #DesignCraft #DesignEthics #VisualDesign #DesignTools #CreativeTech #PromptCrafting #FutureOfDesign #AIProductivity #DesignOps #DesignThinking #AIvsHumanCreativity #DesignStrategy #ProductDevelopment
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Storytelling, Not Spin: Founder-Led Marketing with Dan Woods
07/29/2025
Storytelling, Not Spin: Founder-Led Marketing with Dan Woods
In this episode of podcast, hosts and are joined by , an expert in founder-led marketing. Dan shares his extensive experience in helping software engineers and product management professionals tell their stories better. The discussion spans Dan's career journey from working on early internet projects like Starwave and thestreet.com, to founding Evolved Media. Dan emphasizes the importance of authentic, founder-driven communication in building an audience and discusses the nuances of applying founder-led marketing in tech companies. The episode also covers the risks and adjustments needed in the traditional playbook for effective founder-led marketing. 00:00 Introduction and Welcome 00:37 Guest Introduction: Dan Woods 00:54 Dan's Early Career and Pre-Internet Era 02:27 The Street.com and Early Internet Journalism 08:58 Transition to Evolved Media 09:49 Founder-Led Marketing Explained 12:36 Challenges and Strategies in Founder-Led Marketing 18:10 The Role of Authenticity in Marketing 20:53 Expanding Founder-Led Marketing Beyond LinkedIn 25:48 Leveraging Founder-Led Marketing for Various Business Needs 29:00 Understanding Client Interests and Passions 30:10 Creating Detailed Personas 32:19 Challenges in Founder-Led Marketing 33:05 The Role of AI in Marketing 34:11 The Future of Marketing: Drama and Storytelling 41:09 Risks and Downsides of Founder-Led Marketing 47:10 Getting Started with Founder-Led Marketing 49:37 Conclusion and Final Thoughts Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: Dan Woods: Evolved Media: #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #StartupMarketing #FounderLedMarketing #StoryDrivenGrowth #AuthenticMarketing #MarketingForEngineers #EngineeringLeadership #ProductLeadership #FounderBrand #EarlyStageStartups #TechStorytelling #LinkedInStrategy #MarketingPlaybook #BuildInPublic #SaaSMarketing #ContentStrategy #StartupGrowth #MarketingWithAI #EvolvedMedia #ThoughtLeadership
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The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams
07/22/2025
The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams
In this episode of podcast, hosts and dig deep into the real-world lessons of managing outsourced and distributed engineering teams. Drawing on decades of experience with partners in Romania, India, Syria, and Ukraine, they unpack what makes these relationships thrive, or fail. From timezone pains and cultural mismatches to the power of long-term trust and shared context, Scott and Brad cover the spectrum of challenges leaders face when their teams span the globe. They share tips for CTOs navigating fractional teams, staff augmentation models, and agency partnerships, and reflect on how the rise of generative AI is starting to echo some of the same tensions and tradeoffs seen in outsourcing. If you're building a product with engineers you don't see in the same room, or considering whether AI is the next evolution of outsourcing, this conversation is a must-listen. 00:00 Introduction: The Need for Communication in Distributed Teams 01:04 Challenges of Outsourcing: Pros and Cons 01:24 Personal Experiences with Outsourcing 02:00 Successful Outsourcing Strategies 02:35 Long-term Commitments and Time Zone Issues 03:33 Staff Augmentation and Agency Experiences 06:32 Fractional CTO Insights and Common Issues 19:06 The Importance of Shared Understanding 21:21 The Role of Product Management and Technical Leadership 22:24 Future of Outsourcing and AI Integration 23:39 Conclusion and Call to Action Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #GenAI #AIRevolution #AIEngineer #BuildWithAI #GenerativeAI #StartupTech #RemoteTeams #OutsourcingStrategy #DistributedEngineering #EngineeringManagement #StartupTech #FractionalCTO #TeamVelocity #EngineeringCulture #BuildWithAI #GenerativeAI #AIAndOutsourcing #GlobalTeams #TimeZoneChallenges #ScalingEngineering #TechLeadership #OffshoreEngineering #AgencyWork #Nearshoring
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From Code to Careers: AI’s Disruption of Software and Work Itself
07/15/2025
From Code to Careers: AI’s Disruption of Software and Work Itself
In this episode of podcast, hosts and dive into the fast-evolving world of generative AI—and what it means for the future of software development, careers, and the economy at large. They unpack how tools like GPT-4o and Claude are shifting the very nature of programming work, boosting productivity while raising deeper questions about the future of white-collar jobs. From the rise of AI-assisted coding to ethical concerns around climate impact and military use, Scott and Brad cover the technical, social, and philosophical stakes of this moment. They also explore whether a future with fewer human coders could spark bigger societal changes—like universal basic income—and make the case for why adaptability, critical thinking, and a willingness to learn new tools are the keys to surviving (and thriving) in this new AI-powered landscape. 00:00 Introduction and Greetings 00:27 Discussing AI and Augmented Programming 03:20 AI's Impact on Productivity and Society 04:23 Climate Impact and Future Concerns 05:01 AI in Healthcare and Other Applications 08:08 The Future of Software Development 15:40 Generative AI and Personal Projects 24:59 Advice for the Next Generation 27:46 The Challenge of Staying Current 28:33 Specialization vs. Generalization 28:47 The Role of AI in Specialized Jobs 30:20 Navigating the Rapid Tech Changes 31:31 Optimizing AI Collaboration 33:19 Understanding the Cynefin Framework 35:01 Complex vs. Complicated Systems 39:46 AI's Impact on Software Engineering 41:55 The Future of QA and Testing 44:33 Preparing for an AI-Driven Future 49:27 The Debate on Universal Basic Income 51:29 Concluding Thoughts and Ethical Questions 52:26 Outro and Credits Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: Why using ChatGPT is not bad for the environment - a cheat sheet: Cynefin Framework: #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Ctos #CtoPodcast #Technology #Engineering #SoftwareDevelopment #Entrepreneurship #Leadership #Management #EngineeringLeadership #TechnologyLeadership #EngineeringManagement #GenAI #AIRevolution #AIEngineer #BuildWithAI #GenerativeAI #StartupTech #ClaudeAI #GPT4o #OpenAI #AIProductivity #LLMTools #AIEngineering #FutureOfWork #AgenticAI #AIAgents #AIInStartups #CTOInsights #SoftwareDevelopment #AIUpdate #TechStrategy #FastMovingTech
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How GenAI Is Changing the Two Guys in a Garage Founder Story
07/08/2025
How GenAI Is Changing the Two Guys in a Garage Founder Story
In this episode of podcast, hosts and welcome tech entrepreneurs and avid scuba divers and 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: Scott Porad: Brad Hefta-Gaub: Justin Wolf: Joe Malek: #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
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Autonomous Engineering Teams: What Works, What Breaks
07/01/2025
Autonomous Engineering Teams: What Works, What Breaks
In this episode of podcast, hosts and 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: Scott Porad: Brad Hefta-Gaub: Mindsets That Shape Software Delivery Team Structures - #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
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The End of Programming As We Know It? Justin Kaufman's tips on building fast with AI
06/26/2025
The End of Programming As We Know It? Justin Kaufman's tips on building fast with AI
In this bonus episode of podcast, hosts and engage in a deep and insightful conversation with their guest 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: Scott Porad: Brad Hefta-Gaub: Justin Kaufman: #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
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From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman
06/24/2025
From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman
In this episode of podcast, hosts and interview special guest . 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: Scott Porad: Brad Hefta-Gaub: Justin Kaufman: #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
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Fake Profiles, Real Disruption: What AI Is (and Isn’t) Doing to Tech Recruiting with Dave Hardwick
06/19/2025
Fake Profiles, Real Disruption: What AI Is (and Isn’t) Doing to Tech Recruiting with Dave Hardwick
In this episode of podcast, hosts and discuss with , 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: Scott Porad: Brad Hefta-Gaub: Dave Hardwick: #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
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Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick
06/17/2025
Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick
In this episode of podcast, hosts and welcome , 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: Scott Porad: Brad Hefta-Gaub: Dave Hardwick: #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
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Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox
06/12/2025
Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox
In this bonus episode of podcast, hosts and dive into a conversation with , 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: Scott Porad: Brad Hefta-Gaub: Greg Conklin: Greg's Blog: #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
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Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin
06/10/2025
Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin
In this episode of podcast, hosts and are joined by special guest 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: Scott Porad: Brad Hefta-Gaub: Greg Conklin: Greg's Blog: #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
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Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams
06/03/2025
Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams
In this episode of podcast, hosts and 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: Scott Porad: Brad Hefta-Gaub: #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
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Exploring AI, Knowledge, and Ethics with John Helm (Bonus Episode)
05/29/2025
Exploring AI, Knowledge, and Ethics with John Helm (Bonus Episode)
In this bonus episode of podcast, hosts and sit down once again with technologist and philosopher , 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: Scott Porad: Brad Hefta-Gaub: John Helm: #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
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Understanding and Managing Technical Debt: Insights from John Helm
05/27/2025
Understanding and Managing Technical Debt: Insights from John Helm
In this episode of podcast, hosts and welcome guest to discuss the complexities and ramifications of technical debt within software projects. The conversation explores various analogies, including financial bonds and naked calls, to explain the impact of technical debt on project timelines and functionality. John offers insights on measuring technical debt, its human aspects, and strategies for managing complexity in software systems. The episode highlights the importance of defining technical debt, communicating its impact to business stakeholders, and finding a balance in software development to avoid costly delays and incomplete features. 00:00 Introduction and Guest Welcome 02:06 Defining Tech Debt 04:50 The Human Element in Tech Debt 07:28 Financial Analogies and Tech Debt 21:42 Complexity and Dependencies 29:54 The Challenge of Refactoring Complexity 31:12 Defining and Addressing Technical Debt 33:44 The Risks of Over-Decoupling 37:55 Considering Technical Bankruptcy 43:16 Balancing Technical Debt and Developer Satisfaction 51:11 Exploring Technical Debt Metrics 53:19 Conclusion and Final Thoughts Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: John Helm: SPACE Developer Productivity: OMG Automated Technical Debt Measure: #TechPodcast #EngineeringPodcast #PodcastForDevs #HowManyCtos #Podcast #Ctos #TechnicalDebt #TechDebt #MeasuringTechDebt #SoftwareArchitecture #EngineeringLeadership #CtoPodcast #PlatformEngineering #SoftwareMaintenance #Refactoring #LegacyCode #HumanFactors #BehavioralEconomics #DecisionMaking #StakeholderCommunication #RiskManagement #OriginalMistakes #SecondSystemEffect #BondModel #NakedCalls #TechnicalBankruptcy #EngineeringProductivity #TeamHealth #SpaceMetrics #DoraMetrics #ContinuousImprovement #DeferredMaintenance
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The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges
05/20/2025
The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges
In this episode of podcast, hosts and discuss the intricate challenges of engineering leadership, focusing on the decomposition of monolithic software systems and the monumental task of managing tech debt. They delve into the practical strategies for breaking down monoliths, the complexity of interdependencies and 'God objects,' and debate the merits of incremental rewrites versus complete overhauls. The conversation highlights the need for continuous investment in system maintenance and the struggle to measure the tangible benefits of these efforts. They explore metrics like DORA and the difficulty in aligning business stakeholders with long-term, patient refactoring initiatives. This episode provides valuable insights into effectively handling legacy codebases and advocating for engineering investments. 00:00 Introduction and Podcast Setup 00:47 Key Challenges in Engineering 01:40 Decomposing the Monolith 04:10 Strategies for Incremental Improvement 06:12 Real-World Examples and Challenges 18:31 Measuring Engineering Productivity 21:54 The Challenge of Consistent Processes 23:25 Estimation Accuracy as a Key Metric 25:58 The Complexity of Measuring Value 30:44 The Financial Argument for Maintenance 36:41 Declaring Technical Debt Bankruptcy 42:41 Concluding Thoughts and Outro Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: #TechPodcast #EngineeringPodcast #DevTalks #PodcastForDevs #HowManyCtos #Podcast #Technology #Leadership #Ctos #TechnicalDebt #Management #ProblemSolvingTechniques #ProblemSolvingStrategies #Engineering #Entrepreneurship #EngineeringManagement #Monoliths #Microservices #Dora #SoftwareArchitecture #MonolithToMicroservices #DecomposeTheMonolith #BallOfMud #GodObjects #LegacyCode #Refactoring #EngineeringProductivity #PlatformEngineering #CtoPodcast #EngineeringLeadership #ScalingEngineering #TeamVelocity #CycleTime #DoraMetrics #TechnicalStrategy #BuildVsRewrite #DevCulture #CleanCode #SoftwareMaintenance #ContinuousImprovement #DeferredMaintenance #YakShaving #OctopusObjects #InboxBankruptcy #ReplaceTheBoat #PrometheusShip #ShipOfTheseus
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Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith
05/13/2025
Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith
In this episode of podcast, hosts and are joined by , a seasoned tech leader with a background in both music and technology. Kevin shares insights from his early career in the music industry, his journey through various tech roles, and his book 'It Depends'. The discussion covers important topics like learning from failure, managing tech debt, and the impact of AI-assisted coding. Kevin also talks about the value of retrospectives, even after successful projects, and shares experiences from his tenure at Spotify. As a fun bonus Brad and Kevin both discuss their histories as record label owners and conclude by recommending some of their new favorite music. 00:00 Introduction and Guest Welcome 00:55 Record Label Stories 02:42 Kevin's Career Journey 07:34 Writing 'It Depends' 13:19 Lessons from Failure 18:04 Spotify Retrospectives 25:02 Feature Requests and Fun Stories 27:42 Exploring Music Algorithms 28:36 Technical Challenges and Business Implications 29:23 The Social Aspect of Music Sharing 31:29 Managing Multiple Spotify Accounts 33:00 Tackling Tech Debt in Monolithic Systems 42:23 AI Assisted Coding: A Tool for the Future 48:40 Music Recommendations and Closing Remarks Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: Kevin Goldsmith: It Depends Book: Tacocat: The Telescreens: #podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #retrospectivs #ai #aiassistedcoding #punkrock
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Navigating Technical Debt and Code Quality in Agile Teams
05/06/2025
Navigating Technical Debt and Code Quality in Agile Teams
In this episode of podcast, hosts and discuss a recent incident in a small engineering team that highlights challenges of managing technical debt even with skilled developers and robust code review processes. They explore the importance of refactoring in agile methodologies, the pitfalls of large pull requests, and the complexities of quantifying and prioritizing technical debt. The conversation touches on the limitations of traditional code review processes and the potential of automated CI tools to enforce code quality. The episode underscores how even well-intentioned teams can fall prey to subtle coding anti-patterns and offers insights for improving tech debt management at different organizational scales. 00:00 Introduction and Welcome 00:30 Discussing a Recent Incident 00:58 Importance of Code Reviews 03:00 Challenges in Code Refactoring 05:25 Code Review Process and Human Error 07:22 Tools and Strategies for Code Quality 08:11 Evaluating and Managing Tech Debt 15:47 Conclusion and Call to Action 16:06 Outro and Credits Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: Defining, Measuring, and Managing Technical Debt - Google Research #podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #codereviews #cicd
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The Reality of AI in Software Engineering and the Future of Work
04/29/2025
The Reality of AI in Software Engineering and the Future of Work
In this episode of podcast, hosts and discuss a recent OpenAI study on AI's effectiveness in completing real-world freelance software engineering tasks. They delve into the results showing that AI models completed only 26% of tasks successfully, highlighting current limitations. The conversation transitions to broader topics including the increasing use of AI in various industries, the potential displacement of jobs, and the essential skill of learning to work with AI. They also explore the energy consumption concerns related to AI queries and the possible environmental impact. The discussion reflects on the evolving nature of work and technological revolutions, and speculates on the future role of AI in everyday tasks. 00:00 Introduction: The Next Revolution 00:20 AI Coding Experiment on Upwork 02:35 Results and Analysis of AI Performance 03:30 Challenges and Limitations of AI 06:09 AI in the Workplace: A New Mandate 08:12 The Rise of Vibe Coding 11:00 AI Natives vs. AI Immigrants 12:41 The Hype Machine and Future of AI 15:22 Energy Consumption and Environmental Impact 19:50 Conclusion: The AI Revolution Continues Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: OpenAI Research Paper: #podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #ai #aicoding #vibecoding #aiassistedcoding
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Tackling Tech Culture and Interviewing: Insights from Ted Neward
04/22/2025
Tackling Tech Culture and Interviewing: Insights from Ted Neward
In this episode of podcast, hosts and welcome special guest , a senior distinguished engineer at Capital One, joins the hosts to discuss the challenges and intricacies of engineering leadership and technology culture. Ted shares his diverse experiences, from his previous roles at Rocket Mortgage and Smartsheet to his current position. The discussion delves into the often overlooked aspects of job descriptions, interview processes, and the importance of measurable and actionable performance expectations. Ted also reflects on the use of coding projects in interviews, the role of AI tools in programming, and the necessity of training interviewers to avoid unconscious bias. This episode provides valuable insights into creating effective and inclusive engineering cultures. 00:00 Introduction and Guest Welcome 00:34 Ted's Professional Journey 01:27 Exploring Esoteric Programming Languages 03:11 Tech Culture at Rocket Mortgage 04:16 Challenges in Job Descriptions and Interviewing 08:02 The Importance of Leveling Guidelines 11:36 Defining Good Code 19:02 Interview Process and Structural Guidance 25:53 Interview Training and Culture Challenges 27:09 Unintended Consequences of Filtering 27:59 Systems Thinking in Hiring 30:21 Bias and the Interview Process 31:28 Sample Coding Projects in Interviews 35:44 AI in the Hiring Process 43:29 The Philosophy of Interviewing 47:50 Concluding Thoughts and Reflections 49:50 Outro and Credits Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub: Ted Neward: #podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #hiring #engineeringtalent
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The Power of Drafting Implementation Plans: Insights and Strategies
04/15/2025
The Power of Drafting Implementation Plans: Insights and Strategies
In this episode of podcast, hosts and discuss the importance of having an implementation plan in software development. They emphasize the role that written plans play in fostering collaboration and scaling projects. Through a candid conversation originally recorded in the summer of 2024, they dive into the nuances of translating business requirements into code, the core competencies required for engineering leaders, and best practices for creating effective implementation plans. The episode also addresses common challenges engineers face, such as decision paralysis and the reluctance to share early ideas, while offering strategies for overcoming these hurdles. The hosts also share a comprehensive checklist for determining when a written implementation plan is necessary, touching on topics like schema changes, new technologies, and coordination across teams. The importance of a supportive, feedback-rich culture in engineering teams is highlighted as a key factor in successful project execution. 00:00 Introduction to the Podcast 00:48 The Core Skill in Software Development 02:29 Coaching Engineers on Implementation Plans 04:06 The Importance of Written Implementation Plans 06:02 Challenges and Solutions in Implementation Planning 09:57 Creating a Collaborative Culture 18:11 Guidelines for Formal Implementation Plans 23:09 Conclusion and Call to Action 23:34 Outro and Credits Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub:
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Learning Styles and Team Dynamics: A Journey from Personal Trips to Strategic Decisions
04/08/2025
Learning Styles and Team Dynamics: A Journey from Personal Trips to Strategic Decisions
In this episode of podcast, hosts and dive into the fascinating world of learning styles and their impact on teamwork in both remote and in-person environments. The conversation begins with Scott's personal trip, transitioning into an insightful discussion about the importance of understanding and leveraging different cognitive styles within engineering teams. The episode highlights how visual, kinesthetic, and auditory learning play crucial roles in effective communication and decision-making, supported by examples from strategic planning and mentoring junior engineers. The hosts stress the significance of intentional approaches to creating shared understandings, particularly in remote settings. 00:00 Introduction and Podcast Origins 00:50 Family Trip to Philadelphia 03:38 Work Trip to San Francisco 04:27 The Importance of In-Person Meetings 07:52 Learning Styles and Cognitive Styles 17:08 Mentoring in a Remote World 23:35 Conclusion and Final Thoughts 27:55 Outro and Credits Resources: How Many CTOs Pod: Scott Porad: Brad Hefta-Gaub:
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Bonus Episode: Challenges and Insights From Using Cursor to Add a Feature to Our Website
04/03/2025
Bonus Episode: Challenges and Insights From Using Cursor to Add a Feature to Our Website
In this bonus episode of podcast, hosts and discuss their hands-on experience with an AI agent for updating their podcast website. They share the AI's initial success, followed by its struggle with a more complex task, leading to valuable insights. Key takeaways include the importance of knowing when to reset the AI, providing clear instructions, and the need for strong QA practices. They also touch on personal approaches to problem-solving and the balance between AI assistance and human oversight. Watch the on our . 00:00 Introduction and Welcome 00:27 AI Coding Experiment 00:58 Challenges with AI Assistance 04:21 Human vs AI Problem Solving 05:40 Trust and Familiarity with Code 10:20 QA and Error Handling 12:04 Conclusion and Sign-off
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Embracing AI in Software Development: An Interview with Michael Natkin of Glowforge
04/01/2025
Embracing AI in Software Development: An Interview with Michael Natkin of Glowforge
In this episode of podcast, hosts and welcome special guest , a distinguished CTO with an Oscar and a James Beard Award. The discussion centers on the transformative impact of AI in coding and engineering, from the use of tools like Cursor and Code Rabbit to the potential of AI agents in automating complex tasks. The conversation delves into how AI is reshaping both junior and senior engineering roles, the nuances of prompting AI, and the promising yet cautious foray of non-technical users into the coding world. The trio also explores the future of software development and the importance of evolving with AI to safeguard career prospects in the tech industry. 00:00 Introduction and Welcome 00:36 Meet Michael Natkin: A Unique CTO 01:21 Michael's Journey: From Louisville to Glowforge 02:28 Achievements: James Beard Award and Oscar 03:31 Diving into AI and Coding 05:02 Real-World AI Experiences 05:19 AI Tools for Engineers 07:49 Challenges and Opportunities with AI 16:08 The Future of Junior Engineers 21:23 Exploring AI Tools and Systems 22:50 The Rapid Evolution of AI Tools 23:02 Non-Technical Engineers Making an Impact 23:37 Internal Tools and Their Effectiveness 24:41 Challenges with LLM-Generated Code 26:24 The Role of CTOs in Bridging Technical Gaps 27:11 Non-Technical Teams Using AI for Coding 30:02 The Future of AI in Software Development 30:14 Real-World Examples of AI Coding Success 31:33 Skepticism and Open-Mindedness in AI Adoption 33:19 The Evolution of Software Engineering 40:13 Encouraging Teams to Embrace AI 42:26 Final Thoughts and Reflections
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Org Structures and Measuring Platform Team Success
03/25/2025
Org Structures and Measuring Platform Team Success
In this episode of podcast, hosts and discuss the critical role of a Chief Technology Officer (CTO) as a bridge between technology and business success. They delve into important topics such as organizing engineering teams, managing tech debt, and the trade-offs between enhancing engineering velocity and reducing operational costs. They emphasize the importance of clear metrics and accountability to measure team performance and align engineering efforts with business goals. Citing real-world examples and experiences, they provide insights into maintaining a balance between profitability and technical excellence. This episode also explores cultural shifts needed within organizations to prioritize collective objectives and improve overall efficiency. 00:00 Introduction to the Role of a CTO 00:34 Meet the Hosts: Scott and Brad 00:47 Challenges Faced by Engineering Leaders 02:26 Organizing Engineering Teams 05:35 The Importance of Platform Teams 16:14 Balancing Profitability and Maintenance 20:50 Cultural and Process Considerations 25:33 Real-World Examples and Strategies 27:18 Contemplating a Shift in Platform Strategy 27:31 Defining Platform KPIs and Value 28:40 Customer Satisfaction and Platform Velocity 30:14 Balancing Cost and Velocity in Platform Teams 34:58 Organizational Structure and Conway's Law 39:19 Engineering Metrics and Success 42:36 Connecting Technology to Business Success 45:48 Implementing and Socializing New Ideas 52:37 Podcast Conclusion and Call to Action
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Effective Staff Meetings: Balancing Structure and Flexibility
03/18/2025
Effective Staff Meetings: Balancing Structure and Flexibility
In this episode of , hosts and discuss best practices for running effective staff meetings. They explore different meeting structures, including ad hoc agendas, the 'ball of mud' pattern, and structured rhythms for sprint reviews and operations reviews. The duo emphasizes the importance of having a clear agenda to avoid unproductive meetings and suggest using categorized agenda items to align discussions with organizational goals. They also address the challenge of keeping attendees engaged and focused on key objectives. Practical tips for promoting fiscal responsibility, system uptime, and team engagement are shared to help leaders run more efficient and meaningful staff meetings. 00:00 The Importance of Meeting Agendas 00:21 Introduction to the Podcast 00:32 Different Approaches to Staff Meetings 01:14 Effective Meeting Structures 02:43 Tailoring Meetings to Company Needs 04:20 Balancing Structure and Flexibility 06:37 Addressing Common Meeting Issues 09:46 Implementing Structured Agendas 12:06 Engaging Attendees in Meetings 14:02 Conclusion and Podcast Outro
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Building Trust and Authentic Connections in Remote Teams
03/12/2025
Building Trust and Authentic Connections in Remote Teams
In this episode of , hosts and discuss the importance of building trust within a team, especially when working remotely. They delve into personal anecdotes, effective management strategies like office hours, 5-minute summary videos, and regular one-on-ones. Brad and Scott emphasize the role of authenticity, vulnerability, and positivity in fostering trust and share their experiences tackling legacy culture in new roles. They conclude by reiterating that every interaction either builds or destroys trust, advocating for a genuine and transparent approach to leadership. 00:00 Introduction and Connection 00:32 Meet the Hosts 00:39 Patreon Perks and Swag 01:09 Boat Talk and Personal Stories 03:44 Building Trust in Teams 10:35 Empowerment and Ownership 11:57 Navigating Legacy Culture 16:04 Engaging with Team Members 17:22 Navigating Group and One-on-One Settings 18:03 Building Trust in Group Settings 19:55 Effective One-on-One Strategies 22:00 Open Office Hours and Authenticity 24:05 Remote Trust Building Techniques 28:26 The Power of Micro Interactions 29:54 Authenticity in Remote Leadership 36:38 Conclusion and Podcast Outro
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Embracing Innovation: Introducing the PR FAQ Framework with Marcelo Calbucci
03/04/2025
Embracing Innovation: Introducing the PR FAQ Framework with Marcelo Calbucci
In this episode of , hosts and sit down with , a seasoned CTO, startup founder, and author of . Marcello shares insights on the PR FAQ framework—an innovation decision-making tool used extensively at Amazon—and its applicability to startups, product managers, and even internal projects within larger organizations. The conversation covers the steps to creating a PR FAQ, common pitfalls, and tips on how to integrate this framework into established corporate cultures. Marcello also discusses his transition from startups to Amazon, the importance of internal alignment, and the value of answering tough, strategic questions early in the project lifecycle. 00:00 Introduction and Guest Welcome 00:58 Marcello's Background and New Book 02:08 Experience at Amazon 03:46 Understanding PR FAQ 05:25 Importance of Customer Value 07:07 Team Alignment and Decision Making 08:54 PR FAQ in Practice 15:14 Using PR FAQ for Internal Projects 19:18 Adopting PR FAQ in Established Organizations 20:56 Overcoming OKR Failures 21:45 Implementing PR FAQ Format 22:55 Common Pitfalls of PR FAQ 26:03 Confidentiality and Sharing PR FAQ 28:53 Using PR FAQ for Personal and Team Clarity 31:21 Controversial Aspects of PR FAQ 34:45 Adopting PR FAQ in Startups 37:42 Writing a PR FAQ Book 39:33 Conclusion and Where to Find the Book
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Measuring Technical Debt and Technical Investments
02/19/2025
Measuring Technical Debt and Technical Investments
How Many CTOs Does It Take? Exploring Startups, Process, and Engineering Efficiency In this episode, two CTOs tackle a wide range of topics, starting with the humorous notion of the number of CTOs needed to accomplish common tasks like naming a podcast or establishing coding standards. They share insights into their professional lives, discussing the intricate dynamics of hiring family, the nuances of early startup life, and the importance of implementing processes from the get-go. The conversation delves deep into engineering management strategies, from effective retrospectives and debt registers to the pivotal role of estimation accuracy as a proxy for team performance. They also explore cutting-edge tools like GitHub Codespaces and methods to measure leverage within teams. The discussion is rich with actionable insights for tech leaders and startup enthusiasts, emphasizing the balance between productive processes and agile development. 00:00 Introduction and Podcast Title Discussion 01:14 Hiring Family for Work 03:37 Stealth Startup Insights 04:31 Process and Team Dynamics 10:02 Breaking the Iron Triangle 15:54 Exploring GitHub Codespaces 21:05 The Challenge of Tech Debt 22:17 Creating a Debt Register 23:16 Project Retros and Estimating Costs 27:08 The Importance of Leverage 31:42 Measuring Engineering Efficiency 36:23 Closing Thoughts and Announcements
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Introducing Our Hosts: Scott and Brad
02/19/2025
Introducing Our Hosts: Scott and Brad
Tech Journeys: From Early Internet Days to AI and Beyond In this episode, hosts Scott Porad and Brad Hefta-Gaub share their extensive career journeys in the tech industry, revealing their paths from early consumer-facing internet roles to leading engineering teams at high-growth startups. Scott discusses his rise from building websites at the University of Washington to heading engineering at TaskRabbit, highlighting his ventures in online media, e-commerce, social media, and gig economy businesses. He also touches on his evolving perspectives on AI and the distinctive culture at TaskRabbit's parent company, IKEA. Brad recounts his tenure at RealNetworks, his experience with VR ventures, his adventures in the mountains, and his current role focusing on remote work technology. Both hosts share insights on the challenges of transitioning from engineering roles to CTO positions and the importance of balancing business acumen with technical expertise. 00:00 Introduction and Podcast Announcement 00:41 Meet Scott: Career Journey 01:32 Early Career and Internet Boom 02:52 Successes and Failures in Startups 04:24 Working with Brad and Healthcare Challenges 08:12 Current Role at TaskRabbit 10:03 Insights on IKEA and Company Culture 14:17 Brad's Career Path and Early Successes 20:56 Lessons from Startups and Fractional CTO Work 31:06 The Role of a CTO in Startups 37:38 Conclusion and Future Episodes
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