Chris Pirillo is an entrepreneur, creator, event organizer, and online community leader who has been a guide to the world of tech for everyday users since the early days of the web.

On this episode of the GeekWire Podcast, we catch up with Chris about his latest project, CreatorTech.net, an email newsletter and monthly meetup focused on the intersection of creativity and artificial intelligence. The next CreatorTech meetup is scheduled for Monday, Sept. 25, at the Microsoft Reactor in Redmond.

We also discuss some of the latest AI and tech tools that Chris has been finding useful, and hear his take on corporate return-to-office mandates — spoiler alert, he's not a fan!
Chris Pirillo on the new iPhone 15, and the edited take discussed on the show.
The latest CreatorTech email with a list of 25 AI tools to check out.
Our last GeekWire Podcast/Radio conversation with Chris in June 2013.

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

<a href="https://chrispirillo.bio.link/">Chris Pirillo</a> is an entrepreneur, creator, event organizer, and online community leader who has been a guide to the world of tech for everyday users since the early days of the web.
On this episode of the GeekWire Podcast, we catch up with Chris about his latest project, <a href="http://creatortech.net/">CreatorTech.net</a>, an email newsletter and monthly meetup focused on the intersection of creativity and artificial intelligence. The next CreatorTech meetup is <a href="https://www.eventbrite.com/e/creatortechnet-at-the-crossroads-of-creativity-emerging-tech-like-ai-tickets-705692915507?aff=oddtdtcreator">scheduled for Monday, Sept. 25</a>, at the Microsoft Reactor in Redmond.
We also discuss some of the latest AI and tech tools that Chris has been finding useful, and hear his take on corporate return-to-office mandates — spoiler alert, he's not a fan!
<ul>
<li>Chris Pirillo <a href="https://www.youtube.com/watch?v=nBd8xMqPytY">on the new iPhone 15</a>, and the <a href="https://youtu.be/nBd8xMqPytY?si=pF87tlPv2O-KRJH0">edited take</a> discussed on the show.</li>
<li>The <a href="https://creatortechnet.substack.com/p/creatortechnet-remember-september">latest CreatorTech email</a> with a list of 25 AI tools to check out.</li>
<li><a href="https://www.geekwire.com/2013/geekwire-radio-world-vlogging-chris-pirillo/">Our last GeekWire Podcast/Radio conversation</a> with Chris in June 2013.</li>
</ul>
With GeekWire co-founder Todd Bishop. Edited by Curt Milton.

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

Human creativity and AI: Catching up with Chris Pirillo

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;

Study warns Seattle over-relies on Big Tech; Seattle Times v. Microsoft; Apple's iPhone Duo echoes the past

This week: The NBA suspends former Microsoft CEO Steve Ballmer for a year and hits the Clippers with $30 million in fines and five lost draft picks over allegedly sham endorsement deals for Kawhi Leonard, drawing comparisons to the Microsoft antitrust era.

A new Redfin report says San Francisco's housing market is booming on AI wealth while Seattle slumps, with the Bay Area-to-Seattle migration pipeline nearly dried up.

And the Seahawks sale to the Khosla family officially closes, ending the Paul Allen era, with two familiar Seattle tech names surfacing in the new ownership group.

Plus, the return of the GeekWire Trivia Challenge.

Related Stories and Links

Ballmer / Clippers
NBA suspends Steve Ballmer for 1 year, fines L.A. Clippers $30M over salary-cap scheme
NBA announces penalties and findings arising from investigation of LA Clippers and Kawhi Leonard — NBA
Read the NBA's Report on Clippers, Kawhi Leonard, and Aspiration — Front Office Sports
NBA announces punishments for Clippers after Kawhi inquiry — ESPN
The Briefcase, Ballmer's Social Network and Aspiration's House of Cards: Kawhi-Gate Part VII — Pablo Torre Finds Out

Redfin / SF vs. Seattle housing
AI wealth fuels San Francisco's housing boom while tech layoffs weigh down Seattle
Uber laying off 93 Washington state workers, hitting engineer and management roles at Seattle office
Qualtrics cut 117 jobs tied to Seattle headquarters, new filing shows

Seahawks sale
Two familiar Seattle tech figures turn up on Seahawks co-owner list as sale is finalized
'I'm the 12th man ... I want to represent that': New Seahawks co-owner with deep Seattle tech roots
What to know about Vinod Khosla, the Silicon Valley legend whose family is buying the Seahawks
Apptio co-founders reunite to launch enterprise AI startup Thira with $21M in funding led by Madrona

This week: The NBA suspends former Microsoft CEO Steve Ballmer for a year and hits the Clippers with $30 million in fines and five lost draft picks over allegedly sham endorsement deals for Kawhi Leonard, drawing comparisons to the Microsoft antitrust era.
A new Redfin report says San Francisco's housing market is booming on AI wealth while Seattle slumps, with the Bay Area-to-Seattle migration pipeline nearly dried up.
And the Seahawks sale to the Khosla family officially closes, ending the Paul Allen era, with two familiar Seattle tech names surfacing in the new ownership group.
Plus, the return of the GeekWire Trivia Challenge.
Related Stories and Links<a href="https://www.geekwire.com/2026/seahawks-buyer-vinod-khosla-punts-back-to-team-management-when-it-comes-to-lumen-field-turf-talk/"></a>
Ballmer / Clippers
<ul dir="ltr">
<li><a href="https://www.geekwire.com/2026/nba-suspends-steve-ballmer-for-1-year-fines-l-a-clippers-30m-over-salary-cap-scheme/">NBA suspends Steve Ballmer for 1 year, fines L.A. Clippers $30M over salary-cap scheme</a></li>
<li><a href="https://www.nba.com/news/nba-investigation-findings-la-clippers">NBA announces penalties and findings arising from investigation of LA Clippers and Kawhi Leonard</a> &mdash; NBA</li>
<li><a href="https://frontofficesports.com/article/nba-leonard-ballmer-clippers-full-report/">Read the NBA's Report on Clippers, Kawhi Leonard, and Aspiration</a> &mdash; Front Office Sports</li>
<li><a href="https://www.espn.com/nba/story/_/id/49806356/nba-announces-punishments-clippers-kawhi-probe">NBA announces punishments for Clippers after Kawhi inquiry</a> &mdash; ESPN</li>
<li><a href="https://open.spotify.com/episode/4X4qHA9afNqMArDmGVoxm6">The Briefcase, Ballmer's Social Network and Aspiration's House of Cards: Kawhi-Gate Part VII</a> &mdash; Pablo Torre Finds Out</li>
</ul>
Redfin / SF vs. Seattle housing
<ul dir="ltr">
<li><a href="https://www.geekwire.com/2026/ai-wealth-fuels-san-franciscos-housing-boom-while-tech-layoffs-weigh-down-seattle/">AI wealth fuels San Francisco's housing boom while tech layoffs weigh down Seattle</a></li>
<li><a href="https://www.geekwire.com/2026/uber-laying-off-93-washington-state-workers-hitting-engineer-and-management-roles-at-seattle-office/">Uber laying off 93 Washington state workers, hitting engineer and management roles at Seattle office</a></li>
<li><a href="https://www.geekwire.com/2026/qualtrics-cut-117-jobs-tied-to-seattle-headquarters-new-filing-shows/">Qualtrics cut 117 jobs tied to Seattle headquarters, new filing shows</a></li>
</ul>
Seahawks sale
<ul dir="ltr">
<li><a href="https://www.geekwire.com/2026/two-familiar-seattle-tech-figures-turn-up-on-seahawks-co-owner-list-as-sale-is-finalized/">Two familiar Seattle tech figures turn up on Seahawks co-owner list as sale is finalized</a></li>
<li><a href="https://www.geekwire.com/2026/new-seahawks-co-owner-with-deep-seattle-tech-roots-says-im-the-12th-man-i-want-to-represent-that/">'I'm the 12th man ... I want to represent that': New Seahawks co-owner with deep Seattle tech roots</a></li>
<li><a href="https://www.geekwire.com/2026/what-to-know-about-vinod-khosla-the-silicon-valley-legend-whose-family-is-buying-the-seahawks/">What to know about Vinod Khosla, the Silicon Valley legend whose family is buying the Seahawks</a></li>
<li><a href="https://www.geekwire.com/2026/apptio-co-founders-reunite-to-launch-enterprise-ai-startup-thira-with-21m-in-funding-led-by-madrona/">Apptio co-founders reunite to launch enterprise AI startup Thira with $21M in funding led by Madrona</a></li>
</ul>

NBA's Ballmer crackdown echoes Microsoft antitrust, SF vs. Seattle housing, and a Seahawks tech twist

This week: Bill Gates published a new essay warning that the AI industry is crossing the safety lines it set for itself, and that nobody is preparing for what's coming. At 70 years old, he also uses AI more than most people half his age, and he finds it enthralling, as you'll hear in highlights from our interview with Gates about the memo. Along the way this week, we dig into his three proposals: new institutions for managing the transition, a category of jobs reserved for humans, and a tax on the use and purchase of AI and robots.

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

Related headlines and links
The turbulent AI era is here. The choices we make now are critical. — Bill Gates, Gates Notes
'I am very concerned': Bill Gates says the world needs a plan to deal with AI, and he has three ideas to start
Bill Gates says there's 'no upper limit' on AI, citing opportunity and risk
Etzioni on AI: Bill Gates has the right diagnosis but the wrong prescription
Dwarkesh Podcast: Ryan Greenblatt — What happens once AI can automate AI research?
New York Times: Bill Gates is warning that A.I. is more dangerous than Big Tech will admit
Wall Street Journal: Three takeaways from Bill Gates's 5,784-word warning on AI: 'There is no plan'
MIT Technology Review: Bill Gates says we've passed AI's danger thresholds. Now what?
Axios: Gates confronts the Epstein questions hanging over his AI push
Transcript: Here's what Bill Gates told lawmakers in his recent Epstein testimony

This week: Bill Gates published a new essay warning that the AI industry is crossing the safety lines it set for itself, and that nobody is preparing for what's coming. At 70 years old, he also uses AI more than most people half his age, and he finds it enthralling, as you'll hear in highlights from our interview with Gates about the memo. Along the way this week, we dig into his three proposals: new institutions for managing the transition, a category of jobs reserved for humans, and a tax on the use and purchase of AI and robots.
With Todd Bishop and John Cook. Edited by Curt Milton. Music by Daniel L.K. Caldwell.
Related headlines and links
<ul>
<li><a href="https://www.gatesnotes.com/work/make-ai-work-for-everyone/reader/a-turbulent-ai-era-and-critical-choices-to-make">The turbulent AI era is here. The choices we make now are critical.</a> &mdash; Bill Gates, Gates Notes</li>
<li dir="ltr"><a href="https://www.geekwire.com/2026/i-am-very-concerned-bill-gates-says-the-world-needs-a-plan-to-deal-with-ai-and-he-has-three-ideas-to-start/">'I am very concerned': Bill Gates says the world needs a plan to deal with AI, and he has three ideas to start</a></li>
<li dir="ltr"><a href="https://www.geekwire.com/2026/bill-gates-says-theres-no-upper-limit-on-ai-citing-opportunity-and-risk/">Bill Gates says there's 'no upper limit' on AI, citing opportunity and risk</a></li>
<li><a href="https://www.geekwire.com/2026/etzioni-on-ai-bill-gates-has-the-right-diagnosis-but-the-wrong-prescription/">Etzioni on AI: Bill Gates has the right diagnosis but the wrong prescription</a></li>
<li>Dwarkesh Podcast: <a href="https://www.dwarkesh.com/p/ryan-greenblatt">Ryan Greenblatt &mdash; What happens once AI can automate AI research?</a></li>
<li dir="ltr">New York Times: <a href="https://www.nytimes.com/2026/08/26/technology/bill-gates-ai-risks.html">Bill Gates is warning that A.I. is more dangerous than Big Tech will admit</a></li>
<li dir="ltr">Wall Street Journal: <a href="https://www.wsj.com/tech/ai/three-takeaways-from-bill-gatess-5-784-word-warning-on-ai-there-is-no-plan-aa0c3441">Three takeaways from Bill Gates's 5,784-word warning on AI: 'There is no plan'</a></li>
<li dir="ltr">MIT Technology Review: <a href="https://www.technologyreview.com/2026/08/26/1142946/bill-gates-ai-danger-threshold/">Bill Gates says we've passed AI's danger thresholds. Now what?</a></li>
<li dir="ltr">Axios: <a href="https://www.axios.com/2026/08/26/gates-confronts-the-epstein-questions-hanging-over-his-ai-push">Gates confronts the Epstein questions hanging over his AI push</a></li>
<li dir="ltr"><a href="https://www.geekwire.com/2026/transcript-heres-what-bill-gates-told-lawmakers-in-his-recent-epstein-testimony/">Transcript: Here's what Bill Gates told lawmakers in his recent Epstein testimony</a></li>
</ul>

Human creativity and AI: Catching up with Chris Pirillo

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