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: Amazon is blocking Meta's new Muse AI assistant from shopping on Amazon.com, saying the agent doesn't identify itself and violates the site's conditions of use. We explain why the standoff is an early sign of a much bigger fight over whether AI agents can use websites and apps on people's behalf, and why Amazon has so much riding on the answer.

For the definitive word on the issue, we ask Muse what it has to say for itself, and get an impressively sophisticated and evenhanded answer. 

We recorded this week's show live at Daniel's Broiler in downtown Seattle, in front of a room of startup founders and CEOs, at a dinner hosted and sponsored by Northern Trust.

Mike Fridgen, a longtime Seattle entrepreneur and Madrona venture partner now working on a stealth startup, joins us to talk about whether Seattle is still a good place to build a company. The conversation covers the region's talent, its history and the debate over taxes including Seattle's JumpStart payroll tax, which Mayor Katie Wilson's new budget holds flat.

Then we take questions from the room. Ridge AI CEO Ellie Fields asks how business leaders can engage productively in building the region, Latch CEO Stefan Kalb asks why Seattle has less venture capital than the Bay Area and ACME Brains founder Mary Jesse asks how to get past polarization.

We close with a satellite-themed GeekWire Trivia Challenge and an unexpected announcement from Starfish Space co-founder Austin Link.

Related links
Amazon blocks Meta's Muse AI assistant in new standoff over agentic shopping
Facing 'seismic shifts' in tech sector, Seattle mayor freezes JumpStart tax rates in new budget
'The warning signs are flashing': New regional partnership calls for cohesive Seattle-area tech strategy
Data visualization all-stars unveil Ridge AI with $2.6M to fix the analytics problem for SaaS apps
With NASA's backing, Starfish Space is getting ready for the orbital debut of its flagship Otter spacecraft

With GeekWire co-founders John Cook and Todd Bishop. Music by Daniel L.K. Caldwell. 

This week: Amazon is&nbsp;<a href="https://www.geekwire.com/2026/amazon-blocks-metas-muse-ai-assistant-in-new-standoff-over-agentic-shopping/">blocking Meta's new Muse AI assistant</a> from shopping on Amazon.com, saying the agent doesn't identify itself and violates the site's conditions of use. We explain why the standoff is an early sign of a much bigger fight over whether AI agents can use websites and apps on people's behalf, and why Amazon has so much riding on the answer.
For the definitive word on the issue, we ask Muse what it has to say for itself, and get an impressively sophisticated and evenhanded answer.&nbsp;
We recorded this week's show live at <a href="https://danielsbroiler.com/pages/locations-daniels-downtown">Daniel's Broiler</a> in downtown Seattle, in front of a room of startup founders and CEOs, at a dinner hosted and sponsored by <a href="https://www.northerntrust.com/">Northern Trust</a>.
<a href="https://www.linkedin.com/in/mikefridgen/">Mike Fridgen</a>, a longtime Seattle entrepreneur and Madrona venture partner now working on a stealth startup, joins us to talk about whether Seattle is still a good place to build a company. The conversation covers the region's talent, its history and the debate over taxes including Seattle's JumpStart payroll tax, which Mayor Katie Wilson's new budget holds flat.
Then we take questions from the room. Ridge AI CEO <a href="https://www.linkedin.com/in/elliefields/">Ellie Fields</a> asks how business leaders can engage productively in building the region, Latch CEO <a href="https://www.linkedin.com/in/stefankalb/">Stefan Kalb</a> asks why Seattle has less venture capital than the Bay Area and ACME Brains founder <a href="https://www.linkedin.com/in/maryjesse/">Mary Jesse</a> asks how to get past polarization.
We close with a satellite-themed GeekWire Trivia Challenge and an unexpected announcement from Starfish Space co-founder <a href="https://www.linkedin.com/in/austin-link-space/">Austin Link</a>.
Related links
<ul>
<li dir="ltr"><a href="https://www.geekwire.com/2026/amazon-blocks-metas-muse-ai-assistant-in-new-standoff-over-agentic-shopping/">Amazon blocks Meta's Muse AI assistant in new standoff over agentic shopping</a></li>
<li dir="ltr"><a href="https://www.geekwire.com/2026/facing-seismic-shifts-in-tech-sector-seattle-mayor-freezes-jumpstart-tax-rates-in-new-budget/">Facing 'seismic shifts' in tech sector, Seattle mayor freezes JumpStart tax rates in new budget</a></li>
<li dir="ltr"><a href="https://www.geekwire.com/2026/the-warning-signs-are-flashing-new-regional-partnership-calls-for-cohesive-seattle-area-tech-strategy/">'The warning signs are flashing': New regional partnership calls for cohesive Seattle-area tech strategy</a></li>
<li dir="ltr"><a href="https://www.geekwire.com/2026/data-visualization-all-stars-unveil-ridge-ai-with-2-6m-to-fix-the-analytics-problem-for-saas-apps/">Data visualization all-stars unveil Ridge AI with $2.6M to fix the analytics problem for SaaS apps</a></li>
<li dir="ltr"><a href="https://www.geekwire.com/2026/nasa-sspicy-starfish-space-otter-debut/">With NASA's backing, Starfish Space is getting ready for the orbital debut of its flagship Otter spacecraft</a></li>
</ul>
With GeekWire co-founders John Cook and Todd Bishop. Music by Daniel L.K. Caldwell.&nbsp;

Live show: Amazon, Meta and the fight over the future of AI; Plus, is Seattle still the place to build?

On this week's show, recorded live at Atmosphere Seattle on the shores of Lake Union, Zillow Senior Vice President of Engineering Toby Roberts joins us to talk about what AI is doing to the business of buying and selling homes.

The show was recorded in partnership with Real Estate At Work, the networking group hosted by Leka Devatha, a broker with Real Residential and founder of the redevelopment firm Rehabit Homes, in front of a room of brokers, investors and technologists.

Roberts runs Zillow's core technology with a team of about 650 engineers. He says AI agents will work as a copilot for real estate agents rather than replace them — freeing up their time for the more human aspects of the job, helping people navigate the biggest transaction of their lives. We also talk about the line between AI and reality in home listings, and the tech industry's sudden push to slow AI down.

Then it's the GeekWire Trivia Challenge: four extraordinary Zillow listings for unusual buildings converted into homes. Three are real. One is an AI deepfake. Check out the handout here with the four listings, and see if you can tell the difference. 

With GeekWire co-founders Todd Bishop and John Cook. Edited and produced by Curt Milton.

 

 

On this week's show, recorded live at&nbsp;<a href="https://atmosphereseattle.com/">Atmosphere Seattle</a> on the shores of Lake Union, <a href="https://www.zillow.com/">Zillow</a> Senior Vice President of Engineering <a href="https://www.linkedin.com/in/tobiasroberts/">Toby Roberts</a> joins us to talk about what AI is doing to the business of buying and selling homes.
The show was recorded in partnership with <a href="https://www.meetup.com/realestateatwork/">Real Estate At Work</a>, the networking group hosted by <a href="https://realresidential.com/agents/leka-devatha">Leka Devatha</a>, a broker with <a href="https://realresidential.com/">Real Residential</a> and founder of the redevelopment firm <a href="https://www.rehabithomes.com/">Rehabit Homes</a>, in front of a room of brokers, investors and technologists.
Roberts runs Zillow's core technology with a team of about 650 engineers. He says AI agents will work as a copilot for real estate agents rather than replace them &mdash; freeing up their time for the more human aspects of the job, helping people navigate the biggest transaction of their lives. We also talk about the line between AI and reality in home listings, and the tech industry's sudden push to slow AI down.
Then it's the GeekWire Trivia Challenge: four extraordinary Zillow listings for unusual buildings converted into homes. Three are real. One is an AI deepfake. <a href="https://cdn.geekwire.com/wp-content/uploads/2026/09/trivia_handout_2up.pdf">Check out the handout here</a> with the four listings, and see if you can tell the difference.&nbsp;
With GeekWire co-founders Todd Bishop and John Cook. Edited and produced by Curt Milton.
&nbsp;
&nbsp;

AI meets real estate, with Zillow's engineering SVP Toby Roberts

This week: A study commissioned by the City of Seattle warns that the city is not in decline but is in danger, finding that 10 companies, nine of them in tech, pay three-quarters of the payroll tax on large employers, and that the tax structure uniquely penalizes the hiring of senior, high-compensation workers.

The report says Seattle should be most concerned about AI but most active in cleantech, the one industry the city can actually shape, since it owns the electric utility and controls permitting, building codes and land use.

Meanwhile, the Seattle Times and Newsday sue Microsoft and OpenAI, accusing them of copying hundreds of thousands of articles to train their AI models, putting Microsoft's hometown paper against a company that helps fund some of its journalism.

And Apple's first foldable arrives as the iPhone Duo, reviving the name of the dual-screen phone Microsoft gave up on in 2023, with Surface fans arguing Apple took more than the name.

Which leads us to a new GeekWire Trivia Challenge on the Microsoft products that Apple later turned into categories.

Upcoming Event: GeekWire, in partnership with Real Estate at Work, is recording the GeekWire Podcast live at 4 p.m. Wednesday, Sept. 16, with Toby Roberts, SVP of Engineering at Zillow. Grab a ticket. 

With John Cook and Todd Bishop. Edited by Curt Milton. Music by Daniel L.K. Caldwell. 

 

This week:&nbsp;<a href="https://www.geekwire.com/2026/seattle-economic-study-finds-strong-tech-assets-a-risky-concentration-and-a-tax-that-penalizes-hiring/">A study commissioned by the City of Seattle</a> warns that the city is not in decline but is in danger, finding that 10 companies, nine of them in tech, pay three-quarters of the payroll tax on large employers, and that the tax structure uniquely penalizes the hiring of senior, high-compensation workers.
<a href="https://www.seattle.gov/documents/Departments/economicDevelopment/SeawallBuildingaResilientSeattleEconomy2026.pdf">The report</a> says Seattle should be most concerned about AI but most active in cleantech, the one industry the city can actually shape, since it owns the electric utility and controls permitting, building codes and land use.
Meanwhile, the Seattle Times and Newsday <a href="https://www.geekwire.com/2026/seattle-times-sues-microsoft-and-openai-alleging-they-trained-their-ai-on-its-journalism/">sue Microsoft and OpenAI</a>, accusing them of copying hundreds of thousands of articles to train their AI models, putting Microsoft's hometown paper against a company that helps fund some of its journalism.
And Apple's first foldable <a href="https://techcrunch.com/2026/09/09/apple-unveils-its-first-foldable-the-iphone-duo/">arrives as the iPhone Duo</a>, reviving the name of the dual-screen phone Microsoft gave up on in 2023, with Surface fans arguing Apple <a href="https://www.windowscentral.com/hardware/surface/its-more-than-just-the-name-turns-out-iphone-duo-stole-surface-duos-biggest-selling-point-and-apple-is-right-to-copy-it">took more than the name</a>.
Which leads us to a new GeekWire Trivia Challenge on the Microsoft products that Apple later turned into categories.
Upcoming Event: GeekWire, in partnership with Real Estate at Work, is recording the GeekWire Podcast live at 4 p.m. Wednesday, Sept. 16, with Toby Roberts, SVP of Engineering at Zillow. <a href="https://luma.com/45xf4ukv">Grab a ticket</a>.&nbsp;
With John Cook and Todd Bishop. Edited by Curt Milton. Music by Daniel L.K. Caldwell.&nbsp;
&nbsp;

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

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