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Bezos is back in startup mode, Amazon gets weird again, and the great old-car tech retrofit debate Nov 22, 2025

Show notes

This week: Jeff Bezos is back in startup mode (sort of) with Project Prometheus — a $6.2 billion AI-for-the-physical-world venture that instantly became one of the most talked-about new companies in tech. We dig into what his return to the CEO title really means, why the company’s location is still a mystery, and how this echoes the era when Bezos was regularly launching big bets from Seattle.

Then we look at Amazon’s latest real-world experiment: package-return kiosks popping up inside Goodwill stores around the Seattle region. It’s a small pilot, but it brings back memories of the early days when Amazon’s oddball experiments seemed to appear out of nowhere.

And finally…Todd makes the case for upgrading his 2007 Toyota Camry with CarPlay, Android Auto, and a backup camera — while John questions the logic of sinking thousands into a beloved older car.

All that, plus a mystery Microsoft shirt, a little Seattle nostalgia, and a look ahead to next week’s podcast collaboration with Me, Myself and AI from MIT Sloan Management Review.

With GeekWire co-founders John Cook and Todd Bishop

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An inside view of the AI boom, with Read AI's David Shim Nov 15, 2025

Show notes

This week: A glimpse of the AI frontier in workplace productivity through the eyes of David Shim — serial entrepreneur, Read AI co-founder and CEO, former Foursquare leader, and this year’s GeekWire Awards CEO of the Year. Shim spoke with GeekWire co-founder John Cook at a recent dinner event hosted in partnership with Accenture, in conjunction with our new Agents of Transformation editorial series, exploring AI, productivity, and the future of work.

They discuss the rapid rise of workplace AI, why Shim believes today’s boom is fueled by real revenue rather than dot-com-style subsidies, and where he sees both hype and genuine value emerging. Shim offers insights on AI assistants, cross-team “multiplayer AI,” global adoption, and the controversial idea of “digital twins” built from employees’ work data.

Recorded by Jessica Reeves; edited by Curt Milton.

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Seattle’s history of hardware heartbreak: Big raises, high hopes, hard landings Nov 13, 2025

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Seattle’s consumer-hardware ambitions are once again colliding with economic reality. The struggles of Glowforge and Rad Power Bikes echo a long regional history of big raises, high hopes, and hard landings — shaped by the pandemic, VC, and the unforgiving nature of building real products.

GeekWire co-founders Todd Bishop and John Cook recorded this conversation for the purpose of providing the audio to an AI tool that turned the conversation into a written column that was edited and reviewed before publication. Check it out here.

Related Stories:

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Ring founder Jamie Siminoff on failure, reinvention, and his second act at Amazon Nov 08, 2025

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What’s it like to pitch your dream on Shark Tank, get rejected on national TV in front of eight million people — and then turn that failure into a company Amazon later buys for more than a billion dollars. Ring founder Jamie Siminoff did just that. A serial inventor and entrepreneur, Siminoff joins us to talk about his new book, Ding Dong: How Ring Went from Shark Tank Reject to Everyone’s Front Door (out Nov. 10), sharing the messy, high-stakes, and ultimately inspiring story behind the company.

Now back at Amazon as a vice president leading Ring and the company’s home-security businesses, Siminoff reflects on failure, reinvention, and what comes next in the age of AI.

Related links and stories

Pre-order the book on Amazon.
GeekWire: Ring founder Jamie Siminoff rejoins Amazon in new VP role
Business Insider: Amazon VP says his division is hiring and promoting based on employees’ AI usage
Inc.: The tech founder who wants to fix small-town America

With GeekWire co-founder Todd Bishop

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Seattle’s tech paradox: Amazon's layoffs and the AI boom — or is it a bubble? Nov 01, 2025

Show notes

Why is Amazon laying off 14,000 people during a massive AI boom? Todd and John analyze the Seattle tech paradox, digging into Andy Jassy's 'startup' reasoning and debating whether the AI frenzy is a bubble. Then, they take on the Cascadia high-speed rail: a necessary connector or a misguided project?

Related headlines from the week

Amazon layoffs

Amazon earnings

Microsoft Azure, earnings and OpenAI

Seattle-Portland-Vancouver

With GeekWire co-founders John Cook and Todd Bishop

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The Great Rewiring: How the pandemic set the stage for AI — and what's next Oct 25, 2025

Show notes

From empty offices in 2020 to AI colleagues in 2025, the way we work has been completely rewired over the past five years. Our guest this week studies these shifts closely along with her colleagues at Microsoft. Colette Stallbaumer is the co-founder of Microsoft WorkLab, general manager of Microsoft 365 Copilot, and the author of the new book, WorkLab: Five years that shook the business world, and sparked an AI-first future, from Microsoft’s 8080 Books.

With GeekWire co-founder Todd Bishop; edited by Curt Milton.

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The next PC platform shift? Ed Bott on Microsoft's big Windows AI bet Oct 18, 2025

Show notes

Veteran technology journalist Ed Bott has "seen things," after more than 30 years of covering Microsoft and the PC industry, and he recognizes a pattern in the company's latest AI features for Windows. It's part of a high-stakes effort to avoid missing the next big platform shift — attempting to avoid what happened to the company in the mobile revolution.

Ed joins the GeekWire Podcast to analyze this big bet, digging into the new "Hey Copilot" voice commands, the promise and security risks of "Copilot Actions" that can work on your local files, and Microsoft's strategic shift to bring AI features to all Windows 11 PCs, not just the premium Copilot+ PC models. Plus, we discuss whether users will ever really want to talk to their computers and the timing of it all, right as Windows 10 support comes to an end.

Ed Bott on ZDNet:

Microsoft announcement: Making every Windows 11 PC an AI PC

GeekWire coverage:

Thanks to Buzz Bruggeman of ActiveWords for suggesting this episode.

With GeekWire co-founder Todd Bishop

See omnystudio.com/listener for privacy information.

Vibe-coding a new reality: Chris Pirillo on the rise of AI-powered apps, features, and founders Oct 11, 2025

Show notes

Chris Pirillo, the longtime tech enthusiast and entrepreneur, joins the show this week to discuss how AI software development tools are opening up new possibilities for everyday users, as illustrated by his own experience going from commentator to creator, building nearly 100 apps and games.

He’s launching a free, in-person event series called CTRL+ALT+CREATE Live, where anyone can build something real using AI and no-code tools. The first event takes place from 4 p.m. to 7 p.m on Thursday, Oct. 16 at the Amazon AWS Skills Center in Seattle.

With GeekWire co-founder Todd Bishop.

See omnystudio.com/listener for privacy information.

The Agentic Entrepreneur: How the next wave of AI is changing the startup playbook Oct 04, 2025

Show notes

This week on the GeekWire Podcast: How artificial intelligence is changing the way companies are created, built, and operated. We're on location at Pioneer Square Labs in Seattle with investor and entrepreneur T.A. McCann, a managing director at the startup studio and venture capital firm.

He explains how AI agents are automating complex functions, letting small teams do the work that once required large groups of people. As AI makes product development easier, he says, the key strategic moat for many startups is now shifting to distribution and data.

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