The 2021 virtual GeekWire Awards were held this week, recognizing the top companies, innovators, entrepreneurs and technologies in the Pacific Northwest, as nominated and chosen by the GeekWire community — along with  celebrity cameos.

On this special episode of the GeekWire Podcast, we’re featuring highlights from a behind-the-scenes conversation with former Docker and Concur CEO Steve Singh, managing director of Madrona Venture Group, which was hosted for finalists in advance of the awards by GeekWire co-founder John Cook.

The 2021 virtual GeekWire Awards were held this week, <a href="https://www.geekwire.com/2021/2021-geekwire-awards-revealed-big-winners-surprise-guests-best-pacific-nw-tech/">recognizing the top companies, innovators, entrepreneurs and technologies in the Pacific Northwest,</a> as nominated and chosen by the GeekWire community &mdash;&nbsp;<a href="https://www.geekwire.com/2021/videos-sue-bird-rainn-wilson-bobby-wagner-drunken-tenor-make-surprise-appearances-2021-geekwire-awards/">along with&nbsp; celebrity cameos.</a>
On this special episode of the GeekWire Podcast, we&rsquo;re featuring highlights from a behind-the-scenes conversation with former Docker and Concur CEO Steve Singh, <a href="https://www.madrona.com/team-profiles/steve-singh/">managing director of Madrona Venture Group</a>, which was hosted for finalists in advance of the awards by GeekWire co-founder John Cook.

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.

GeekWire

Madrona's Steve Singh on 6 tech trends to watch post-COVID

This week: As the Musk v. OpenAI trial heads to the jury, we dig into what Microsoft's internal board memos and executive testimony revealed about the origins of the company's massive bet on AI, and why this case matters beyond the billionaire drama. Plus, Howard Schultz, a former Washington governor, and the tech community weigh in on whether Seattle is squandering its edge as an innovation capital. And Todd owes John and the United Kingdom an apology.

RELATED STORIES AND LINKS
Microsoft's CTO testifies about email at the heart of Elon Musk's allegations against the tech giant
OpenAI CEO Sam Altman's stake in Helion Energy draws scrutiny in Musk trial and on Capitol Hill
'Strong, strong no': New filing reveals who Microsoft favored — and opposed — for OpenAI's board
Musk v. Altman: Satya Nadella was worried about Microsoft being 'the next IBM' in OpenAI deal
Are we on a Road to Nowhere? Seattle's growth masks deeper anxieties about its future
Microsoft's multi-agent AI system tops Anthropic's Mythos on cybersecurity benchmark
Seattle Turns Hostile to the Great Businesses It Made (Wall Street Journal, by Howard Schultz)
Association of Washington Business 2026 Spring Summit (TVW, featuring former Gov. Chris Gregoire and former AG Rob McKenna)

With GeekWire co-founders Todd Bishop and John Cook

This week: As the Musk v. OpenAI trial heads to the jury, we dig into what Microsoft's internal board memos and executive testimony revealed about the origins of the company's massive bet on AI, and why this case matters beyond the billionaire drama. Plus, Howard Schultz, a former Washington governor, and the tech community weigh in on whether Seattle is squandering its edge as an innovation capital. And Todd owes John and the United Kingdom an apology.
RELATED STORIES AND LINKS
<ul>
<li><a href="https://www.geekwire.com/2026/microsofts-cto-testifies-about-email-at-the-heart-of-elon-musks-allegations-against-tech-giant/">Microsoft's CTO testifies about email at the heart of Elon Musk's allegations against the tech giant</a></li>
<li><a href="https://www.geekwire.com/2026/openai-ceo-sam-altmans-stake-in-helion-energy-draws-scrutiny-in-musk-trial-and-on-capitol-hill/">OpenAI CEO Sam Altman's stake in Helion Energy draws scrutiny in Musk trial and on Capitol Hill</a></li>
<li><a href="https://www.geekwire.com/2026/strong-strong-no-new-filings-reveal-who-microsoft-favored-and-opposed-for-openais-board/">'Strong, strong no': New filing reveals who Microsoft favored &mdash; and opposed &mdash; for OpenAI's board</a></li>
<li><a href="https://www.geekwire.com/2026/musk-v-altman-satya-nadella-was-worried-about-microsoft-being-the-next-ibm-in-openai-deal/">Musk v. Altman: Satya Nadella was worried about Microsoft being 'the next IBM' in OpenAI deal</a></li>
<li><a href="https://www.geekwire.com/2026/are-we-on-a-road-to-nowhere-seattles-growth-masks-deeper-anxieties-about-its-future/">Are we on a Road to Nowhere? Seattle's growth masks deeper anxieties about its future</a></li>
<li><a href="https://www.geekwire.com/2026/microsofts-multi-agent-ai-system-tops-anthropics-mythos-on-cybersecurity-benchmark/">Microsoft's multi-agent AI system tops Anthropic's Mythos on cybersecurity benchmark</a></li>
<li><a href="https://www.wsj.com/opinion/seattle-turns-hostile-to-the-great-businesses-it-made-ea82b65c">Seattle Turns Hostile to the Great Businesses It Made</a> (Wall Street Journal, by Howard Schultz)</li>
<li><a href="https://tvw.org/video/association-of-washington-business-2026-spring-summit-2026051024/?eventID=2026051024">Association of Washington Business 2026 Spring Summit</a> (TVW, featuring former Gov. Chris Gregoire and former AG Rob McKenna)</li>
</ul>
With GeekWire co-founders Todd Bishop and John Cook

What we learned about Microsoft in the OpenAI trial, and is Seattle squandering its edge?


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

Related stories
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.

Madrona's Steve Singh on 6 tech trends to watch post-COVID

In 1 playlist(s)

GeekWire

Social links

Follow podcast

Recent clips