Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith
Release Date: 05/13/2025
Design in the Age of AI: Craft, Tools, and the Future of Creativity
How Many CTOs
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...
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Storytelling, Not Spin: Founder-Led Marketing with Dan Woods
How Many CTOs
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...
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The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams
How Many CTOs
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...
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From Code to Careers: AI’s Disruption of Software and Work Itself
How Many CTOs
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...
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How GenAI Is Changing the Two Guys in a Garage Founder Story
How Many CTOs
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...
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Autonomous Engineering Teams: What Works, What Breaks
How Many CTOs
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...
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The End of Programming As We Know It? Justin Kaufman's tips on building fast with AI
How Many CTOs
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...
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From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman
How Many CTOs
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...
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Fake Profiles, Real Disruption: What AI Is (and Isn’t) Doing to Tech Recruiting with Dave Hardwick
How Many CTOs
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...
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Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick
How Many CTOs
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...
info_outline- 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: https://howmanyctospod.com
- Scott Porad: https://www.linkedin.com/in/scottporad/
- Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/
- Kevin Goldsmith: https://www.linkedin.com/in/goldsmith/
- It Depends Book: https://itdependsbook.net/
- Tacocat: http://tacocatdotcom.com/
- The Telescreens: https://linktr.ee/Telescreens