Shows
How Many CTOsStorytelling, Not Spin: Founder-Led Marketing with Dan WoodsIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by Dan Woods, 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 tradi...2025-07-2951 minHow Many CTOsThe Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global TeamsIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 r...2025-07-2224 minHow Many CTOsFrom Code to Careers: AI’s Disruption of Software and Work ItselfIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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.2025-07-1553 minHow Many CTOsHow GenAI Is Changing the Two Guys in a Garage Founder StoryIn 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 c...2025-07-0852 minHow Many CTOsAutonomous Engineering Teams: What Works, What BreaksIn 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...2025-07-0150 minHow Many CTOsThe End of Programming As We Know It? Justin Kaufman's tips on building fast with AIIn 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 delve...2025-06-2616 minHow Many CTOsFrom Chicken to Chatbots: Generative AI in Hospitality with Justin KaufmanIn 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 Prepare...2025-06-241h 02How Many CTOsFake Profiles, Real Disruption: What AI Is (and Isn’t) Doing to Tech Recruiting with Dave HardwickIn 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 E...2025-06-1910 minHow Many CTOsBeyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick 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 engin...2025-06-1741 minHow Many CTOsBonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and DropboxIn 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...2025-06-1211 minHow Many CTOsCulture, Quality, and Tech Debt: Lessons from the Front Lines with Greg ConklinIn 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 uninten...2025-06-1047 minHow Many CTOsLessons from the Mountains: Retrospectives and the Secret Sauce of High Performance TeamsIn 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...2025-06-0342 minHow Many CTOsExploring AI, Knowledge, and Ethics with John Helm (Bonus Episode) 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 w...2025-05-2911 minHow Many CTOsUnderstanding and Managing Technical Debt: Insights from John HelmIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome guest John Helm 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 delay...2025-05-2754 minHow Many CTOsThe Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 busin...2025-05-2043 minHow Many CTOsEmbracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by Kevin Goldsmith, 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...2025-05-1352 minHow Many CTOsNavigating Technical Debt and Code Quality in Agile TeamsIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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 codin...2025-05-0616 minHow Many CTOsThe Reality of AI in Software Engineering and the Future of Work In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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...2025-04-2921 minHow Many CTOsTackling Tech Culture and Interviewing: Insights from Ted NewardIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome special guest Ted Neward, 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...2025-04-2250 minHow Many CTOsThe Power of Drafting Implementation Plans: Insights and StrategiesIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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...2025-04-1524 minHow Many CTOsLearning Styles and Team Dynamics: A Journey from Personal Trips to Strategic DecisionsIn this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub 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...2025-04-0828 min