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 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: 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

#podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #retrospectivs #ai #aiassistedcoding #punkrock