
Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox
In 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...
12 Jun 202511min

Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin
In 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 bu...
10 Jun 202547min

Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams
In 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 ...
3 Jun 202542min

Exploring 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 conv...
29 Mai 202511min

Understanding and Managing Technical Debt: Insights from John Helm
In 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 ...
27 Mai 202554min

The 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 ...
20 Mai 202543min

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. Ke...
13 Mai 202552min

Navigating Technical Debt and Code Quality in Agile Teams
In 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 d...
6 Mai 202516min



















