Microsoft is putting Amazon into a difficult position by advocating a tax increase on both companies in their home state. Meanwhile, Apple is placing an even bigger bet on privacy as a feature. We explain a surprising startup investment by two Seattle tech veterans. Plus, the return of the Random Channel.

Microsoft is putting Amazon into a difficult position by advocating a tax increase on both companies in their home state. Meanwhile, Apple is placing an even bigger bet on privacy as a feature. We explain a surprising startup investment by two Seattle tech veterans. Plus, the return of the Random Channel.

GeekWire brings you the week's latest technology news, trends and insights, covering the world of technology from our home base in Seattle. Our regular news podcast features commentary and analysis from our editors and reporters, plus interviews with special guests.

GeekWire reporters John Cook, Todd Bishop and guests talk about the latest tech news and trends.

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Microsoft boxes Amazon into a corner

This week on the show: Conversations with finalists and special guests at the annual GeekWire Awards about AI, innovation, startups, and the forces reshaping their industries, plus a special trivia challenge marking GeekWire's 15th year hosting the event. Guests include:
Luis Poggi, CEO of HouseWhisper AI, winner of CEO of the Year
Tracy Drinkwater, founder of the Seattle Universal Math Museum, STEM Educator of the Year honoree
Ryan James, CEO of Dopl Technologies, finalist for Startup of the Year
Laura Ruderman, CEO of the Technology Alliance
Ross Finman, CEO of Augmodo, finalist for Hardware/Robotics/Physical AI of the Year
Mohammad Rastegari, CEO of ElastixAI, finalist for Startup of the Year

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2026 GeekWire Awards revealed: Big winners — and big love for Seattle — at annual tech celebration
Photos: Inside the 2026 GeekWire Awards

With GeekWire co-founders John Cook and Todd Bishop

This week on the show: Conversations with finalists and special guests at the annual&nbsp;<a href="https://www.geekwire.com/2026/2026-geekwire-awards-revealed-big-winners-and-big-love-for-seattle-at-annual-tech-celebration/">GeekWire Awards</a> about AI, innovation, startups, and the forces reshaping their industries, plus a special trivia challenge marking GeekWire's 15th year hosting the event. Guests include:
<ul>
<li>Luis Poggi, CEO of <a href="https://www.housewhisper.ai/">HouseWhisper AI</a>, winner of CEO of the Year</li>
<li>Tracy Drinkwater, founder of the <a href="https://seattlemathmuseum.org/">Seattle Universal Math Museum</a>, STEM Educator of the Year honoree</li>
<li>Ryan James, CEO of <a href="https://www.dopltechnologies.com/">Dopl Technologies</a>, finalist for Startup of the Year</li>
<li>Laura Ruderman, CEO of the <a href="https://www.technology-alliance.com/">Technology Alliance</a></li>
<li>Ross Finman, CEO of <a href="https://www.augmodo.com/">Augmodo</a>, finalist for Hardware/Robotics/Physical AI of the Year</li>
<li>Mohammad Rastegari, CEO of <a href="https://www.elastix.ai/">ElastixAI</a>, finalist for Startup of the Year</li>
</ul>
Related stories
<ul>
<li><a href="https://www.geekwire.com/2026/2026-geekwire-awards-revealed-big-winners-and-big-love-for-seattle-at-annual-tech-celebration/">2026 GeekWire Awards revealed: Big winners &mdash; and big love for Seattle &mdash; at annual tech celebration</a></li>
<li><a href="https://www.geekwire.com/2026/photos-inside-the-2026-geekwire-awards/">Photos: Inside the 2026 GeekWire Awards</a></li>
</ul>
With GeekWire co-founders John Cook and Todd Bishop

Inside the 2026 GeekWire Awards: Innovators reshaping how we work, build, and learn

This week on the show: Todd reports from inside the Oakland federal courthouse where Elon Musk is suing OpenAI, Sam Altman, and Microsoft, with jury selection revealing just how hard it is to find anyone neutral about Musk these days.

Meanwhile, Microsoft and OpenAI restructured their partnership the same morning the trial began — and less than 24 hours later, OpenAI's models landed on Amazon's cloud.

Then, Microsoft and Amazon both dropped blockbuster earnings, with Azure up 40%, AWS posting its fastest growth in 15 quarters, and the two companies combining for nearly $400 billion in capital spending this year alone.

We also discuss a wild Semafor story about a serial entrepreneur who handed his entire life over to an AI agent that now emails people as him, sets up meetings without his knowledge, and even ordered him a computer.

Plus, John tells the story of how Seattle's Flying Fish Partners — a VC firm with less than $250 million under management — hustled its way into a $1.1 billion seed round alongside Sequoia, Google, and Nvidia.

And we tackle the quickly debunked rumor that Mark Zuckerberg and Tim Cook might buy the Seahawks. And finally, the return of the GeekWire Trivia Challenge.

This week on the show: Todd&nbsp;<a href="https://www.geekwire.com/2026/musk-v-altman-inside-the-courthouse-as-microsofts-13-billion-openai-bet-goes-on-trial/">reports from inside the Oakland federal courthouse</a> where Elon Musk is suing OpenAI, Sam Altman, and Microsoft, with jury selection revealing just how hard it is to find anyone neutral about Musk these days.
Meanwhile,&nbsp;<a href="https://www.geekwire.com/2026/microsoft-and-openai-revamp-partnership-with-trial-in-elon-musk-suit-set-to-begin/">Microsoft and OpenAI restructured their partnership</a> the same morning the trial began &mdash; and less than 24 hours later, <a href="https://www.geekwire.com/2026/openais-models-land-on-amazon-bedrock-one-day-after-microsoft-exclusivity-ends/">OpenAI's models landed on Amazon's cloud</a>.
Then,&nbsp;<a href="https://www.geekwire.com/2026/microsoft-tops-wall-street-expectations-reports-accelerating-azure-growth-and-37b-ai-run-rate/">Microsoft </a>and <a href="https://www.geekwire.com/2026/aws-growth-climbs-to-28-as-amazons-big-ai-bets-start-to-pay-off/">Amazon </a>both dropped blockbuster earnings, with Azure up 40%, AWS posting its fastest growth in 15 quarters, and the two companies combining for nearly $400 billion in capital spending this year alone.
We also discuss&nbsp;<a href="https://www.semafor.com/article/04/24/2026/the-man-who-is-paying-to-see-the-future">a wild Semafor story</a> about a serial entrepreneur who handed his entire life over to an AI agent that now emails people as him, sets up meetings without his knowledge, and even ordered him a computer.
Plus, John tells <a href="https://www.geekwire.com/2026/how-a-seattle-vc-firm-broke-into-the-1-1b-seed-round-for-a-deepmind-legends-superintelligence-startup/">the story of how Seattle's Flying Fish Partners</a> &mdash; a VC firm with less than $250 million under management &mdash; hustled its way into a $1.1 billion seed round alongside Sequoia, Google, and Nvidia.
And we tackle the&nbsp;<a href="https://www.geekwire.com/2026/seahawks-sale-rumor-names-mark-zuckerberg-and-tim-cook-as-potential-bidders-for-nfl-team/">quickly debunked rumor</a> that Mark Zuckerberg and Tim Cook might buy the Seahawks. And finally, the return of the GeekWire Trivia Challenge.

Elon takes the stand, Big Tech drops big numbers, and a small VC gets in on a billion-dollar deal

Bill Hilf has spent decades enterprise tech, open-source technologies, and AI, from IBM and Microsoft to running Paul Allen's portfolio as the CEO of Vulcan. He now chairs the Allen Institute for AI and American Prairie. His debut sci-fi novel, "The Disruption," imagines AI gone very wrong, and implicitly challenges the industry to think differently about how it's building our real future today.

With GeekWire co-founder Todd Bishop. Edited by Curt Milton.

<a href="https://www.linkedin.com/in/bill-h-b554/">Bill Hilf </a>has spent decades enterprise tech, open-source technologies, and AI, from IBM and Microsoft to running Paul Allen's portfolio as the CEO of Vulcan. He now chairs the <a href="https://allenai.org/">Allen Institute for AI</a> and <a href="https://americanprairie.org/">American Prairie</a>. His debut sci-fi novel,&nbsp;<a href="https://www.amazon.com/Disruption-Cycle-W-H-Hilf/dp/B0GD2NCLYW">"The Disruption,"</a> imagines AI gone very wrong, and implicitly challenges the industry to think differently about how it's building our real future today.
With GeekWire co-founder Todd Bishop. Edited by Curt Milton.

Microsoft boxes Amazon into a corner

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