Box CEO and co-founder Aaron Levie joins the GeekWire Podcast to talk about the company’s latest AI initiatives, including a new integration with Microsoft 365 Copilot and a suite of Box AI agents designed to help businesses analyze content, extract data, and generate insights. 

Levie shares how AI is changing the way he and his team work, explains why he believes 2025 is still “day one” for enterprise AI agents, and offers a realistic take on what AI can — and can’t — do today. He also reflects on Box’s evolution, the shifting role of content in the enterprise, and why he thinks AI is creating more work, not less.

RELATED LINKS
GeekWire: Box tightens Microsoft ties with new Copilot integration, builds out its own suite of AI agents
Aaron Levie: How AI is changing my work as CEO at Box

With GeekWire co-founder Todd Bishop

Box CEO and co-founder Aaron Levie joins the GeekWire Podcast to talk about the company&rsquo;s latest AI initiatives, including a new integration with Microsoft 365 Copilot and a suite of Box AI agents designed to help businesses analyze content, extract data, and generate insights.&nbsp;
Levie shares how AI is changing the way he and his team work, explains why he believes 2025 is still &ldquo;day one&rdquo; for enterprise AI agents, and offers a realistic take on what AI can &mdash; and can&rsquo;t &mdash; do today. He also reflects on Box&rsquo;s evolution, the shifting role of content in the enterprise, and why he thinks AI is creating more work, not less.
RELATED LINKS
<ul>
<li>GeekWire: <a href="https://www.geekwire.com/2025/box-tightens-microsoft-ties-with-new-copilot-integration-builds-out-its-own-suite-of-ai-agents/">Box tightens Microsoft ties with new Copilot integration, builds out its own suite of AI agents</a></li>
<li>Aaron Levie: <a href="https://www.linkedin.com/posts/boxaaron_at-box-were-100-focused-on-being-an-ai-first-activity-7320471553207402497-Ih44/">How AI is changing my work as CEO at Box</a></li>
</ul>
With GeekWire co-founder Todd Bishop

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

Box CEO Aaron Levie on AI agents, enterprise data, and the future of work

Someone listening to last week’s GeekWire Podcast caught something we missed: a misleading comment by Alexa during our voice ordering demo — illustrating the challenges of ordering by voice vs. screen. We followed up with Amazon, which says it has fixed the underlying bug.

On this week’s show, we play the audio of the order again. Can you catch it? 

Plus, Microsoft announces a "community first" approach to AI data centers after backlash over power and water usage — and President Trump scooped us on the story. We discuss the larger issues and play a highlight from our interview with Microsoft President Brad Smith.

Also: the technology capturing images of every fan at Lumen Field, UK police blame Copilot for a hallucinated soccer match, and Redfin Glenn Kelman departs six months after the company's acquisition by Rocket.

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

Someone listening to <a href="https://www.geekwire.com/2026/geekwire-podcast-alexas-next-act-microsofts-retail-play-googles-ai-inbox-and-a-smart-bird-feeder-fail/">last week&rsquo;s GeekWire Podcast</a> caught something we missed: a misleading comment by Alexa during our voice ordering demo &mdash; illustrating the challenges of ordering by voice vs. screen. We followed up with Amazon, which says it has fixed the underlying bug.
On this week&rsquo;s show, we play the audio of the order again. Can you catch it?&nbsp;
Plus, Microsoft <a href="https://www.geekwire.com/2026/microsoft-responds-to-ai-data-center-revolt-vowing-to-cover-full-power-costs-and-reject-local-tax-breaks/">announces a "community first" approach to AI data centers</a> after backlash over power and water usage &mdash; and President Trump scooped us on the story. We discuss the larger issues and play a highlight from our interview with Microsoft President Brad Smith.
Also: the technology <a href="https://www.geekwire.com/2026/will-seahawks-fans-have-reason-to-cheer-against-49ers-stadium-cameras-will-capture-the-reaction/">capturing images of every fan</a> at Lumen Field, UK police <a href="https://www.theverge.com/news/861668/uk-police-microsoft-copilot-error-mistake">blame Copilot for a hallucinated soccer match</a>, and Redfin Glenn Kelman&nbsp;<a href="https://www.geekwire.com/2026/redfin-ceo-glenn-kelman-departs-after-leading-seattle-real-estate-giant-for-20-years/">departs</a> six months after the company's acquisition by Rocket.
With GeekWire co-founders John Cook and Todd Bishop; Edited by Curt Milton.

Amazon fixes Alexa voice ordering bug; Microsoft rethinks AI data centers; Stadium cameras capture every Seahawks fan


This week on the GeekWire Podcast: Amazon and Microsoft are racing to define the next era of consumer AI, on multiple fronts. We discuss Amazon's attempt to upgrade Alexa into a true generative AI home chatbot — complete with a new web portal and updated Alexa app — while Microsoft leverages its enterprise strength to win over retailers with a new Copilot Checkout feature.

Plus, we explore Google's upcoming "AI Inbox" for Gmail, which promises to act like an executive assistant for your email. We talk about a DIY bird feeder experiment that resulted in "fuzzy birds," and share our initial experience with AI automation on the PC desktop from Seattle startup Vercept.

We offer a Netflix recommendation, Cover-Up, the new documentary about investigative journalist Seymour Hersh. And on that theme, we lament the loss of a major American newspaper, the Pittsburgh Post-Gazette, and reminisce about the time we made an appearance on its editorial page.

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

This week on the GeekWire Podcast: Amazon and Microsoft are racing to define the next era of consumer AI, on multiple fronts. We discuss Amazon's attempt to upgrade Alexa into a true generative AI home chatbot &mdash; complete with <a href="https://www.geekwire.com/2026/amazons-ai-on-the-web-wrist-and-phone-tech-giant-chases-consumer-rivals-with-latest-moves/">a new web portal and updated Alexa app</a> &mdash; while Microsoft leverages its enterprise strength to win over retailers with<a href="https://www.geekwire.com/2026/microsoft-launches-copilot-checkout-joining-the-ai-shopping-race-against-amazon-google-and-openai/"> a new Copilot Checkout feature</a>.
Plus, we explore Google's upcoming <a href="https://blog.google/products-and-platforms/products/gmail/gmail-is-entering-the-gemini-era/">"AI Inbox" for Gmail</a>, which promises to act like an executive assistant for your email. We talk about a DIY bird feeder experiment that resulted in "fuzzy birds," and share our initial experience with AI automation on the PC desktop from Seattle startup <a href="https://vercept.com/">Vercept</a>.
We offer a Netflix recommendation, <a href="https://www.netflix.com/tudum/articles/cover-up-documentary-release-date-news">Cover-Up</a>, the new documentary about investigative journalist Seymour Hersh. And on that theme, we lament <a href="https://www.nytimes.com/2026/01/07/business/media/pittsburgh-post-gazette-closing.html?unlocked_article_code=1.DVA.rrTv.fA0OBVAIpL36&amp;smid=url-share">the loss of a major American newspaper</a>, the Pittsburgh Post-Gazette, and reminisce about the time we made an appearance <a href="https://www.linkedin.com/posts/bishoptodd_very-sorry-to-see-the-news-about-the-decision-activity-7414823628833357824-L41n/">on its editorial page</a>.
With GeekWire co-founders Todd Bishop and John Cook. Edited by Curt Milton.

Alexa’s next act, Microsoft’s retail play, Google’s AI inbox, and a smart bird feeder fail


The FCC delivered a massive shakeup to the drone industry right before the holidays, adding foreign-made drones (most notably from industry giant DJI) to its "Covered List" of national security threats. While the move effectively bans the sale of future DJI models in the U.S., GeekWire’s Todd Bishop and John Cook explore why this might be a golden economic opportunity for the Pacific Northwest.

Featuring highlights from a recent interview with Blake Resnick of Brinc, the Seattle-based maker of public safety drones, who lobbied for the U.S. policy change and supports the move.

Related story:Drone capital of the world? Seattle could be a big winner in the U.S. crackdown on DJI and others

Plus, the results are in. After ignoring John’s advice and deciding to retrofit his 2007 Toyota Camry with a modern infotainment system, Todd shares the verdict. 

The FCC delivered a massive shakeup to the drone industry right before the holidays, adding foreign-made drones (most notably from industry giant DJI) to its "Covered List" of national security threats. While the move effectively bans the sale of future DJI models in the U.S., GeekWire&rsquo;s Todd Bishop and John Cook explore why this might be a golden economic opportunity for the Pacific Northwest.
Featuring highlights from a recent interview with <a href="https://www.linkedin.com/in/blake-resnick-164871bb/">Blake Resnick</a> of <a href="https://brincdrones.com/">Brinc</a>, the Seattle-based <a href="https://www.geekwire.com/2025/public-safety-drone-maker-brinc-raises-75m-forms-strategic-alliance-with-motorola/">maker of public safety drones</a>, who lobbied for the U.S. policy change and supports the move.
Related story: <a href="https://www.geekwire.com/2025/drone-capital-of-the-world-seattle-could-be-a-big-winner-in-the-u-s-crackdown-on-dji-and-others/">Drone capital of the world? Seattle could be a big winner in the U.S. crackdown on DJI and others</a>
Plus, the results are in. After <a href="https://www.geekwire.com/2025/bezos-is-back-in-startup-mode-amazon-gets-weird-again-and-the-great-old-car-tech-retrofit-debate/">ignoring John&rsquo;s advice</a> and deciding to retrofit his 2007 Toyota Camry with a modern infotainment system, Todd shares the verdict.&nbsp;

Box CEO Aaron Levie on AI agents, enterprise data, and the future of work

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