GeekWire

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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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 2026
• A tale of two Seattles in the age of AI: Harsh realities and new hope for the tech community
• Filing: Amazon cuts more than 2,300 jobs in Washington state as part of broader layoffs
• Amazon layoffs hit software engineers hardest in Washington
• Amazon 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 profits
• Amazon’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 Airlines
• Microsoft beats expectations, reports nearly $35B in Q1 capital spending amid Azure outage
• Microsoft 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 reality
• Cascadia’s AI paradox: A world-leading opportunity threatened by rising costs and a talent crunch
• The ‘enormous barrier’ that threatens economic growth in the Pacific Northwest
• Beta’s unique electric airplane flies into Seattle to wow state officials and aviation experts

With GeekWire co-founders John Cook and Todd Bishop

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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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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 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 own
• A 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

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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.

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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.

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.

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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 innovation
• New TiE Seattle president on how the $100K H-1B fee could snuff out entrepreneurial flame
• Will 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.

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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.

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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.

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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 deal
• Pablo Torre details his investigation on "Pablo Torre Finds Out."
• ESPN's Ramona Shelburne interviews Steve Ballmer.
• Google antitrust ruling gives Microsoft a shaky bridge over search giant’s competitive moat
• KUOW: Is the Google antitrust ruling a ‘big whiff,’ or an advantage for rivals like Microsoft?

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