Introducing Our Hosts: Scott and Brad
How Many CTOs19 Feb 2025

Introducing Our Hosts: Scott and Brad

Tech Journeys: From Early Internet Days to AI and Beyond

In this episode, hosts Scott Porad and Brad Hefta-Gaub share their extensive career journeys in the tech industry, revealing their paths from early consumer-facing internet roles to leading engineering teams at high-growth startups.

Scott discusses his rise from building websites at the University of Washington to heading engineering at TaskRabbit, highlighting his ventures in online media, e-commerce, social media, and gig economy businesses. He also touches on his evolving perspectives on AI and the distinctive culture at TaskRabbit's parent company, IKEA.

Brad recounts his tenure at RealNetworks, his experience with VR ventures, his adventures in the mountains, and his current role focusing on remote work technology.

Both hosts share insights on the challenges of transitioning from engineering roles to CTO positions and the importance of balancing business acumen with technical expertise.

  • 00:00 Introduction and Podcast Announcement

  • 00:41 Meet Scott: Career Journey

  • 01:32 Early Career and Internet Boom

  • 02:52 Successes and Failures in Startups

  • 04:24 Working with Brad and Healthcare Challenges

  • 08:12 Current Role at TaskRabbit

  • 10:03 Insights on IKEA and Company Culture

  • 14:17 Brad's Career Path and Early Successes

  • 20:56 Lessons from Startups and Fractional CTO Work

  • 31:06 The Role of a CTO in Startups

  • 37:38 Conclusion and Future Episodes

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Episoder(94)

What Broke in Tech: Code Quality, AI Guardrails, and the Evolving Software Engineer

What Broke in Tech: Code Quality, AI Guardrails, and the Evolving Software Engineer

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub continue to recap Gergely Orosz's "State of the Tech Industry" talk and focus on what "broke" and "what'...

3 Nov 36min

The State of Tech in 2026: What Changed And What Didn't

The State of Tech in 2026: What Changed And What Didn't

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a Pragmatic Engineer talk on the state of the tech industry in 2026, focusing on what changed an...

27 Okt 32min

The Human Needs in Augmented Coding: A Conversation with Kent Beck

The Human Needs in Augmented Coding: A Conversation with Kent Beck

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview software pioneer Kent Beck about his background (JUnit, test-driven development, extreme progr...

20 Okt 1h 9min

Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between

Preparing for the Worst: Tabletop Exercises, Unit Tests, and Everything In Between

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss TaskRabbit's overnight AWS region migration from us-west-1 to us-west-2, describing the months o...

13 Okt 44min

Understanding The Fear: Adaptive Leadership in the AI Age

Understanding The Fear: Adaptive Leadership in the AI Age

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring...

6 Okt 34min

Simplifying Tech Through Empathy and Understanding with Frank Bravo

Simplifying Tech Through Empathy and Understanding with Frank Bravo

In this episode of "How Many CTOs Does It Take?" podcast, host Brad Hefta-Gaub is joined by guest Frank Bravo, a Bay Area technologist who spent 30 years as CTO in local media, helping put a newspaper...

29 Sep 50min

Managing Skepticism: Balancing Tradition and Technology with AI

Managing Skepticism: Balancing Tradition and Technology with AI

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss how AI is changing software engineering referencing Kent Beck's idea that AI makes much existing...

22 Sep 49min

From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing

From Academia to Industry: Scott Hanson on the Future of AI and Edge Computing

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub interview Scott Hanson, founder and CTO of Ambiq, a company focused on ultra-low-power chips for "intell...

15 Sep 45min

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