GeekWire

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. See omnystudio.com/listener for privacy information.

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. See omnystudio.com/listener for privacy information.

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 AmazonGeekWire:Ring founder Jamie Siminoff rejoins Amazon in new VP roleBusiness InsiderAmazon VP says his division is hiring and promoting based on employees’ AI usageInc.:The tech founder who wants to fix small-town America With GeekWire co-founder Todd Bishop See omnystudio.com/listener for privacy information.

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 confirms 14,000 job cuts, says push for ‘efficiency gains’ will continue into 2026A tale of two Seattles in the age of AI: Harsh realities and new hope for the tech communityFiling: Amazon cuts more than 2,300 jobs in Washington state as part of broader layoffsAmazon layoffs hit software engineers hardest in WashingtonAmazon layoffs reaction: ‘Thought I was a top performer but guess I’m expendable’Amazon CEO says massive corporate layoffs were about agility — not AI or cost-cutting Amazon earnings Amazon stock soars 11% after topping Q3 estimates with $180B in revenue, $21B in profitsAmazon’s Anthropic investment boosts its quarterly profits by $9.5B‘Big Beautiful’ tax benefit: Amazon and other tech giants reap the rewards of new law, for now Microsoft Azure, earnings and OpenAI Microsoft’s Azure reports cloud outage, disrupting global customers including Alaska AirlinesMicrosoft beats expectations, reports nearly $35B in Q1 capital spending amid Azure outageMicrosoft gets 27% stake in OpenAI, and a $250B Azure commitment Seattle-Portland-Vancouver Slowly but surely, high-speed rail backers believe Cascadia mega-project will become a realityCascadia’s AI paradox: A world-leading opportunity threatened by rising costs and a talent crunchThe ‘enormous barrier’ that threatens economic growth in the Pacific NorthwestBeta’s unique electric airplane flies into Seattle to wow state officials and aviation experts With GeekWire co-founders John Cook and Todd Bishop See omnystudio.com/listener for privacy information.

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. See omnystudio.com/listener for privacy information.

Veteran technology journalist Ed Bott has "seen things," after more than 30 years of covering Microsoft, 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+ 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 debuts its next big high-stakes feature in Windows — can you trust it?Windows 10 PC can't be upgraded? You have 5 options - and must act now Microsoft announcement: Making every Windows 11 PC an AI PC GeekWire coverage: Microsoft’s new AI features aim to give Windows a voice and mind of its ownA new era for Windows: Can Microsoft’s longtime engine power another tech revolution? Thanks to Buzz Bruggeman of ActiveWords for suggesting this episode. With GeekWire co-founder Todd Bishop See omnystudio.com/listener for privacy information.

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.

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 business functions, allowing very small teams to manage tasks that once required significant human work. As AI makes product development easier, he says, the key strategic moat for many startups is now shifting to distribution and data. Other topics include: The wearable AI recorder that captures everything he says throughout the day. The rise of the "one-person billion-dollar company" powered by a suite of specialized AI agents. How AI-generated personas are replacing human focus groups for market research. The future of "agent-to-agent" conversations, where different AI systems negotiate with each other on behalf of their companies. With GeekWire co-founder Todd Bishop; Edited by Curt Milton. See omnystudio.com/listener for privacy information.

The U.S. tech and startup community was stunned by an executive order last week imposing a $100,000 fee for employers seeking new H-1B visas for skilled foreign workers, a program heavily used by the technology industry. This move brings a longstanding debate back to the forefront: are skilled immigrants taking American jobs, or are they a vital engine for innovation and economic growth? Our guest this week has a strong point of view on this topic. Shirish Nadkarni is a serial entrepreneur and Microsoft veteran who founded companies acquired by BlackBerry and Rosetta Stone. An immigrant himself, he just released a timely new book, The Indian American Tech Success Story, which makes the case that immigrant founders, particularly from India, are one of America's greatest economic assets — creating far more jobs than they could ever be accused of taking. Related Links and Stories Startup leaders warn new $100K H-1B visa fee will hurt U.S. entrepreneurship and innovationNew TiE Seattle president on how the $100K H-1B fee could snuff out entrepreneurial flameWill new U.S. visa fee boost Canada’s tech sector? B.C. sees an opening against Seattle and Silicon Valley With GeekWire co-founder Todd Bishop; Edited by Curt Milton. See omnystudio.com/listener for privacy information.

This week on the GeekWire Podcast: How artificial intelligence is reshaping media and advertising, and what it says about the future of the creative process. Our guest is Jay Richman, an Amazon vice president of product and technology who leads the technology team developing AI tools used by sellers and brands to create and deploy ads across Amazon's platforms. His career has tracked the evolution of digital media, from early apps for the Palm Pilot to the first wave of streaming at NBC Universal, and the reinvention of podcast ads and monetization at Spotify. Richman, who's based in New York, was in town this week for Amazon's Accelerate seller conference, where he announced new agentic AI capabilities within Amazon's Creative Studio. Related Post: Amazon unveils new agentic AI tools for sellers amid heightened scrutiny With GeekWire co-founder Todd Bishop. Audio editing by Curt Milton. See omnystudio.com/listener for privacy information.

This week: Executive coach and AI strategist Mark Briggs explains why your "personal operating system" needs an upgrade, and how to use AI to get more time back in your day. He shares practical tips for turning scattered notes into a powerful knowledge base and discusses how AI can act as a collaborator to fight procrastination and provide instant feedback. Plus, we play a game of "Bot or Not" to see if you can tell the difference between a human and an AI assistant, and learn how better productivity can lead to achieving personal goals. With GeekWire co-founder Todd Bishop; Edited by Curt Milton. See omnystudio.com/listener for privacy information.

This week on the GeekWire Podcast: Former Microsoft CEO Steve Ballmer and his NBA team, the Clippers, face scrutiny over an alleged salary-cap dodge tied to star Kawhi Leonard. We unpack the report and Ballmer’s emphatic denial, while reflecting on his history in tech and sports. Also: OpenAI's surprise $1.1 billion acquisition of Seattle startup Statsig, and what it says about the AI talent wars. Plus, the ironic role of Microsoft’s own antitrust past in the landmark ruling against Google’s search monopoly this week. Seattle journalist, radio host and bar owner Mike Lewis joins GeekWire's Todd Bishop for this episode, which also features a highlight from a segment with KUOW's Kim Malcolm. Related Stories OpenAI acquires Statsig for $1.1B, names CEO to key role in surprise exit for Seattle-area unicorn‘Absurd’: Steve Ballmer responds to report that Clippers funneled money to star player via endorsement dealon "Pablo Torre Finds Out."interviews Steve Ballmer.Google antitrust ruling gives Microsoft a shaky bridge over search giant’s competitive moatIs the Google antitrust ruling a ‘big whiff,’ or an advantage for rivals like Microsoft? See omnystudio.com/listener for privacy information.

In light of his estate's launch of the new $3.1 billion Fund for Science and Technology, we revisit a classic 2011 interview with the late Microsoft co-founder Paul Allen to explore the "Idea Man" mindset that continues to shape his legacy. The conversation reveals the personal motivations behind his "big bet" philanthropy, his candid thoughts on his partnership with Bill Gates, and his passion for everything from brain science to jamming with rock stars. Related stories and links: Microsoft co-founder Paul Allen’s final act: New $3.1B foundation bets big on science and techIn an age of billionaire backlash, Paul Allen’s lasting legacy stands out in Seattle With GeekWire's Todd Bishop and Kurt Schlosser. See omnystudio.com/listener for privacy information.

What does Seattle gain — and lose — in times of dramatic change? University of Washington Foster School of Business marketing professor Jeff Shulman has spent years studying that question, as host of the Seattle Growth Podcast, director of the Product Management Center, and a civic voice on issues ranging from housing affordability to the campaign to bring back the Sonics. On this episode of the GeekWire Podcast, Shulman joins us to talk about Seattle’s place in the global AI boom, why the city has struggled to produce superstar startups, what AI means for marketing and education, and how civic identity, tech and sports have fueled the region. RELATED STORIES Seattle is a global AI hub — but where are the superstar startups?Despite status as a global tech hub, Seattle passengers still can’t hail a driverless rideKen Griffey Jr. Wants Role in Bringing Seattle Sonics Back Seattle Now Podcast: Casual Friday with Todd Bishop and Jeff Shulman Also check out the Seattle Growth Podcast and "On the Brink" documentary. With GeekWire co-founder Todd Bishop; Edited by Curt Milton See omnystudio.com/listener for privacy information.

Our guests this week: Adam Brotman and Andy Sack, co-authors of the book AI First: The Playbook for a Future-Proof Business and Brand. Brotman was Starbucks’ chief digital officer and later co-CEO of J.Crew. Sack is a founder, investor, and longtime advisor to tech leaders. Together, they run Forum3, a company that helps brands rethink loyalty and customer engagement. Their book argues the winners in this era will be truly AI first — human plus machine, copilots and agents baked into the work. We’ll talk about their ‘holy-shit’ moment with Sam Altman, the banker who did a week’s work in less than two days, and what leaders should actually be doing. With GeekWire co-founder Todd Bishop. See omnystudio.com/listener for privacy information.

Longtime University of Washington computer science professor Ed Lazowska — newly retired at 75 after nearly a half-century on the faculty — joins us to discuss the evolution of computer science, how AI is changing what and how students learn, why specialization is rising, the role of universities in Seattle’s tech economy, and what he plans to tackle next across teaching, advising, and policy. Read more on GeekWire. With GeekWire co-founders Todd Bishop and John Cook. Edited by Curt Milton. See omnystudio.com/listener for privacy information.

This week on the GeekWire Podcast: Microsoft soars past Wall Street expectations, briefly hitting a $4 trillion valuation, while Amazon faces sharper scrutiny over its AI strategy. Todd Bishop and John Cook break down the contrasting earnings results, analyst reactions, and what it all means for the future of AI — and Seattle's place in it. Plus: insights from Microsoft's Mustafa Suleyman on the future of Copilot, a throwback lesson from the Zune era, and a guestbook entry that shows just how mainstream ChatGPT has become. Related stories and links Microsoft plans record $30B in quarterly capital spendingMicrosoft cut product R&D jobs, added operations roles over the past yearMicrosoft beats expectations, says Azure revenue tops $75B annuallyInternal memo: Nadella urges long-term thinking as Azure marks 15 yearsMicrosoft reaches $4 trillion valuation after big earnings reportAmazon Web Services profits squeezed amid AI spending surgeAmazon tops Q2 estimates with $167.7B in revenue, $18.2B in profitsCan Seattle own the AI era? 20 investors and founders weigh the potential From Startup to Exit: Microsoft@50: Birth of Xbox, with Chief Xbox Officer, Robbie Bach Colin & Samir Podcast with Microsoft AI CEO Mustafa Suleyman Tim Ferriss Podcast with Expedia and Zillow co-founder Rich Barton See omnystudio.com/listener for privacy information.

Our guest this week is Brad Anderson — a tech engineering and product leader who spent more than 17 years at Microsoft and is now approaching 5 years at Qualtrics, the experience management technology company, where he’s president of products, user experience, engineering, and security. I’ve known Brad for a while, in fact I’ve been on two of his shows back when he was an enterprise mobility and cloud technology leader at Microsoft, and it was all the rage for executives to have their own video shows. Lunch Break with Brad AndersonThe Ship Room For this week’s show, I went to the Qualtrics Tower in downtown Seattle to talk with Brad about how he thinks about building tech today — how AI is starting to change the way products come together, and how expectations are shifting for both the people using the tools and the people building them. I also turn the tables on Brad in the final segment with a game about cloud and AI terms called "Real or Ridiculous" — stick around to play along. But first, he reminded me about the random case of mistaken identity that brought us together in the first place, back in the day. Listen to the show to hear the story, and see the related post on GeekWire to read highlights. — GeekWire co-founder Todd Bishop Edited by Curt Milton. See omnystudio.com/listener for privacy information.

How are companies really using AI? And is it truly working? AWS Vice President Francessca Vasquez joins the GeekWire Podcast to talk about what companies are actually doing with AI today, and what's holding them back. We discuss real-world deployments, lessons from AWS customers across industries, and the challenges and opportunities in scaling generative and agentic AI. Related Stories and Links: Amazon gives $100M boost to AWS Generative AI Innovation Center, betting on agentic AIOver 40% of Agentic AI Projects Will Be Canceled by End of 2027Top announcements of the AWS Summit in New York, 2025Amazon cuts hundreds of AWS cloud jobs after strategic review, says AI wasn’t the main factorMeta snags Seattle startup co-founder for Zuckerberg’s elite superintelligence team With GeekWire co-founder Todd Bishop. Edited by Curt Milton. See omnystudio.com/listener for privacy information.

On this episode of the GeekWire Podcast, we’re joined by Colin Sebastian, senior research analyst at Baird and one of the most respected voices in tech and internet investing. We dive into how Amazon, Google, and Meta are positioning themselves in the AI era — from Amazon’s Alexa+ and infrastructure strategy, to Google’s balancing act between search and generative chatbots, to Meta’s AI talent push. Colin also shares his take on the broader investment climate, how he separates hype from lasting value, and how AI is reshaping his own research process. Plus, we get his outlook on the next wave in gaming, the signals he’s watching in the data, and how today’s AI boom compares to the dot-com era that marked the start of his career. With GeekWire co-founder Todd Bishop. Edited by Curt Milton. See omnystudio.com/listener for privacy information.