How Many CTOs13 Maj 2025

Embracing 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 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

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