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In this episode, Eric Bowman (CTO @ King.com) breaks down how AI is changing programming, creativity, and technical leadership. We talk about what “living on the edge” looks like with modern AI tools, why “AI is just technology” is still the right mental model, and how CTOs can build organizations that stay fast, adaptable, and focused on time-to-value.

We dive into:

Chapters:

[00:53] Meet Eric Bowman: CTO of King.com

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Outline

With experience spanning French defense contractors (Orange, Thales), navigating DocuSign's complex French acquisition, and now steering Superhuman through its Grammarly acquisition/rebrand, Loïc brings a unique European-to-SF perspective on technical leadership.

Key insights for engineering leaders:

Execution & Velocity

Technical Architecture Decisions

Team Organization

Framework Skepticism

Product & Design Philosophy

Acquisition Integration

Cultural Observations

Chapters:

[00:51] Superhuman, Grammarly, and the rebrand to Superhuman Mail

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In this episode, Matthias Keller (CPO @ Kayak) shares strategic lessons about making AI product decisions under uncertainty. With 12 years at Kayak and experience spanning multiple AI waves—from Alexa to LLMs—Matthias offers a masterclass in knowing when to invest early and when to wait.

We dive into:

This conversation offers actionable frameworks for product and engineering leaders navigating AI strategy decisions.

Chapter 1: From Sensors to Travel Tech (00:00 - 09:00)

Chapter 2: Competitive Landscape & Google Flights (09:00 - 13:00)

Chapter 3: Platform Evolution - From Alexa to LLMs (13:00 - 28:00)

Chapter 4: AI Mode & Conversational Search (28:00 - 41:00)

Chapter 5: Distribution in the AI Era (41:00 - 46:00)

Chapter 6: AI Democratizing Development (46:00 - 50:00)

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In this episode, we dive deep into the world of analytical databases with Mark Raasveldt, the co-founder and CTO of DuckDB Labs. Mark takes us through his fascinating journey from academic research to building one of the most talked-about databases in the industry.

We explore:

This conversation offers unique insights into database architecture, performance optimization, and the intersection of academic research and commercial success.

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What does it take to build a company worth Google's $32 billion acquisition? Solal shares the hard-won lessons from scaling technical teams during one of the fastest-growing security companies in history.

Key leadership insights from the episode:

• CTO Office Evolution: How Wiz split technical leadership into 3-4 specialized tracks focused on domain expertise rather than geography

Technical Context (18% of episode):

Chapters:

Here's the thing about agile transformations: they almost never work the way they're supposed to. Teams end up more siloed than before, chasing tickets instead of solving actual problems. Klaus Breyer has seen this pattern everywhere, and he's figured out some ways to break it.

Klaus runs product and technology at Edding—yeah, the pen company—but his background is anything but traditional. He learned team coordination by managing 40-person World of Warcraft raids, ran a few startups, and now applies those lessons to building software at a 150-year-old German manufacturer. It's an unusual path that gives him a different perspective on how teams actually work together.

We talked about Shape Up methodology, but honestly, the more interesting stuff was about changing how teams think about their work. Klaus has some pretty specific ideas about when teams are ready to ditch ticket systems entirely, how to spot the early warning signs of assembly-line thinking, and why most agile implementations fail at the mindset level.

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Also, Edding is doing some wild stuff with technology—like building a driver license verification system using invisible conductive ink that smartphones can read. Who knew pen companies were this technical?

What we covered:

[00:51] Klaus's background and how Edding ended up doing serious tech

Quotes worth remembering:

"Almost all teams out there have silos. You can have silos in the smallest teams. You can have silos with three or four people if they are thinking about the work in the wrong way." [11:15]

"One of the biggest signs is when you need to do tradeoffs because the time is running out. And then if you do tradeoffs because the time is running out, most of the times the tradeoffs are then done or led by the engineers because we don't have time to complete this feature." [13:22]

What does 25 years in tech teach you? Kelsey Hightower, a self-taught engineer who rose to become a Distinguished Engineer at Google and a key figure in the Kubernetes community, sits down with Tobi to share unfiltered insights from his extensive career and his recent decision to retire at 42.

This conversation goes beyond the hype, focusing on the timeless principles of technical leadership, system maintenance, and career strategy. Kelsey breaks down the reality of infrastructure management, the hidden costs of complexity, and why the most important engineering skill is understanding the business.

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Technical insights for CTOs and engineering leaders:

TIMESTAMPS:

QUOTES:

The AI transformation challenge isn't just technical—it's organizational. Peter Gostev, Head of AI at Moonpig, discusses building practical AI capabilities in a 600-person company while navigating the gap between AI hype and implementation reality.

From managing adoption across 150 software engineers to partnering with non-technical teams, Peter shares insights on driving meaningful AI transformation that goes beyond superficial tool usage. This conversation explores the contrast between industry claims of widespread AI adoption and the nuanced reality of implementing AI at scale.

TIMESTAMPS:

QUOTES:

• ""I think there's never really been more exciting time in my career versus now and every time we can we can just do more and more and more, which is just such a cool position to be in."" - Peter Gostev [00:06:39]

• ""I think people really underestimating where we are and or how much more there is to go… we are really just at the beginning of these investments starting to come through."" - Peter Gostev [00:07:01]

• ""On any given project, most of the work is actually non-AI work… most of it is integrations, scaffolding, deployment, UI, all of the things like that. And then the AI part of it is normally maybe 10, 20% of the actual work."" - Peter Gostev [00:28:01]

Two veteran CTOs tear down today's tech hype with brutal honesty and hard-won experience. Raz Schweiger-Shuty shares his controversial approach to technical leadership at auxmoney, where he stopped a microservices rewrite and focused on business outcomes over engineering trends.

From his early days as a QA engineer to running 80-person engineering organizations, Raz demonstrates why sometimes the best technical decision is the boring one that actually works. This conversation offers a masterclass in pragmatic technical leadership for an age obsessed with the latest frameworks and architectures.

Key insights for technical leaders:

TIMESTAMPS:

Technical Deep Dives:

"Our model factory runs thousands of experiments before a single production model is trained. It’s an empirical science—every component, from data ingestion to evals, is versioned and traceable." – Eiso Kant

Chapters: