Introducing Our Hosts: Scott and Brad
How Many CTOs19 Helmi 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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Year In Review: How Many CTOs Does It Take To Finish A Season?

Year In Review: How Many CTOs Does It Take To Finish A Season?

In this special public service announcement episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub announce that they will be taking a two-week break for the holidays ...

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Turtles All The Way Down: AI Insights with Scott W. Bradley

Turtles All The Way Down: AI Insights with Scott W. Bradley

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome guest Scott W. Bradley, Managing Partner at Facet Digital, to delve into the complexities and po...

16 Joulu 202559min

The AI Race: Who's Ahead, Anthropic or OpenAI?

The AI Race: Who's Ahead, Anthropic or OpenAI?

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub compare Anthropic and OpenAI's distinct business strategies. While OpenAI takes a high-risk, expansive a...

9 Joulu 202525min

CTO Therapy: The Risks and Rewards of Vendor Partnerships

CTO Therapy: The Risks and Rewards of Vendor Partnerships

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub delve into Scott's recent meeting with AWS. They discuss the concept of vendors supporting their clients...

2 Joulu 202541min

Let Them Eat Tokens: AI Efficiency vs. Global Good

Let Them Eat Tokens: AI Efficiency vs. Global Good

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the pervasive influence of AI, starting with a critical look at Apple's Siri and its struggles...

25 Marras 202540min

Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements

Cabinet Doors Should Open: Avoiding Assumptions in Product Requirements

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the critical importance of clear requirements in both hardware and software projects. Using the ...

18 Marras 202533min

The State of AI in 2025: What the DORA Report Reveals

The State of AI in 2025: What the DORA Report Reveals

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the 2025 DORA Metrics Report on the state of AI-assisted software development. They discuss ke...

11 Marras 202538min

The AI Hype Cycle: Navigating Growth and Skepticism

The AI Hype Cycle: Navigating Growth and Skepticism

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub reflect on the recent shifts in Big Tech's approach to AI, discussing the changing perceptions and econo...

4 Marras 202530min

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