How Many CTOs13 Touko 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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Jaksot(85)

The Hardware/Software Blend: Visionary Innovations in Health Tech with Eyebot's Jack Moldave

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Jack Moldave of Eyebot, a company he co-founded nearly six years ago to make getting glasses a...

1 Syys 52min

Fast, On Time, or Fully Utilized? Choosing What to Optimize in Engineering Delivery

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a leadership conversation where three senior stakeholders wanted different outcomes from enginee...

25 Elo 16min

The Pace of Innovation: Systems Thinking for Faster Engineering

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub open with travel and sports talk, including World Cup rules, then pivot to Scott's change-management tra...

18 Elo 56min

Method to the Madness: A CTO Framework for Systemic AI Adoption

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how CTOs must frame narratives that help teams organize around ideas, inspired by how Scott expl...

11 Elo 45min

There's A Pattern To Follow: An Interview with Robert "Uncle Bob" Martin

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are honored to interview Robert "Uncle Bob" Martin, who recounts his 60+ year programming journey from a...

4 Elo 1h 1min

Is Uncle Bob Right? Reading Code vs. Architecting the Future

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how Robert "Uncle Bob" Martin—author of Clean Code and Agile Manifesto signer—sparked online con...

28 Heinä 43min

Token Maxxing and Local Inference: Navigating the Shift in AI Usage for Developers

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss token spending and the "token maxing" backlash, sparked by a GitHub Copilot budget issue and bro...

21 Heinä 1h

This Has Always Been A Problem: Slot Machine Devs and Growing Junior Engineers in the Age of AI

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how managing armies of coding agents can be physically draining, likening it to context switchin...

14 Heinä 56min