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

This week on the GeekWire Podcast, we discuss how AI is transforming our local tech giants, changing the fundamental nature of work, and blurring the lines between human and machine.

We dive into the memo that has Amazon employees either signing up for AI training or updating their resumes; unpack why you're answering emails at 10 p.m.; and explain how one of us ended up quizzing his dentist's office assistant (or was it an AI chatbot?) about whether he or she (or it?) was human. Then we ask the new Alexa+ what it (she?) thinks about the exchange. 

Related stories
Andy Jassy’s long game: Amazon’s reinvention enters its 5th phase as AI upends the workforce
Amazon CEO: AI will shrink corporate workforce in coming years
The ‘infinite workday’ is here — and Microsoft says AI will make it worse if we’re not careful

With GeekWire co-founders Todd Bishop and John Cook.

 

This week on the GeekWire Podcast, we discuss how AI is transforming our local tech giants, changing the fundamental nature of work, and blurring the lines between human and machine.
We dive into the memo that has Amazon employees either signing up for AI training or updating their resumes; unpack why you're answering emails at 10 p.m.; and explain how one of us ended up quizzing his dentist's office assistant (or was it an AI chatbot?) about whether he or she (or it?) was human.&nbsp;Then we ask the new Alexa+ what it (she?) thinks about the exchange.&nbsp;
Related stories
<ul>
<li><a href="https://www.geekwire.com/2025/andy-jassys-long-game-amazons-reinvention-enters-its-5th-phase-as-ai-upends-the-workforce/?utm_source=chatgpt.com">Andy Jassy&rsquo;s long game: Amazon&rsquo;s reinvention enters its 5th phase as AI upends the workforce</a></li>
<li><a href="https://www.geekwire.com/2025/amazon-ceo-says-ai-push-will-shrink-corporate-in-next-few-years">Amazon CEO: AI will shrink corporate workforce in coming years</a></li>
<li><a href="https://www.geekwire.com/2025/the-infinite-workday-is-here-and-microsoft-says-ai-will-make-it-worse-if-were-not-careful/">The &lsquo;infinite workday&rsquo; is here &mdash; and Microsoft says AI will make it worse if we&rsquo;re not careful</a></li>
</ul>
With GeekWire co-founders Todd Bishop and John Cook.
&nbsp;

Amazon, Microsoft, and the new realities of AI at work

A message from GeekWire co-founder Todd Bishop: This episode of the GeekWire Podcast is unlike any we’ve done before. It touches on some of the most contentious and disputed issues in the tech industry, and in the world more broadly. 

It started with my curiosity and desire to understand something that happened in March, at GeekWire’s independent Microsoft @ 50 event. I was on stage interviewing Microsoft Vice Chair and President Brad Smith when the conversation was interrupted by a protester. 

The group behind the protest, called No Azure for Apartheid, represents current and former Microsoft employees who want the company to end its cloud computing and AI contracts with the Israeli military. They cite concerns over how they believe their work is being used by Israel.

Addressing the larger issues raised by the group, Microsoft said in a May 15 post that it conducted internal and external reviews and “found no evidence to date that Microsoft’s Azure and AI technologies have been used to target or harm people in the conflict in Gaza.” 

After covering Microsoft’s statements and the group’s response — and seeing the continued protests unfold at Microsoft events — I decided to dig deeper and learn more. 

As part of that, I invited one of the organizers of No Azure for Apartheid to join me on this podcast, for a conversation about the motivations behind the group, their views on Microsoft’s responsibilities, and how the tech industry intersects with international conflicts. 

Our guest is software engineer Hossam Nasr, who was fired by Microsoft last year related to protests on the Microsoft campus. In fact, he was the first to protest inside the GeekWire event.

What followed was a complex conversation — one that at times went beyond Microsoft’s role into broader political and ethical criticisms of Israel’s actions in Gaza. 

These are deeply polarizing issues, and we know there are strong, divergent opinions about them. I’ve added context conveying Microsoft’s responses, and noting areas where statements and characterizations about Israel, Palestine, and Gaza are the subject of dispute. 

The conversation includes detailed descriptions of the ongoing conflict in Gaza and some historical comparisons that some listeners may find disturbing or offensive. And lastly, we recorded this conversation in late May, before the latest developments in the Middle East.

Related Links: 
Microsoft:Statement on the Issues Relating to Technology Services in Israel and Gaza
Associated Press: As Israel uses US-made AI models in war, concerns arise about tech’s role in who lives and who dies
AP:Microsoft fires employees who organized vigil for Palestinians killed in Gaza
+972:Leaked documents expose deep ties between Israeli army and Microsoft
The Verge: Microsoft blocks emails that contain ‘Palestine’ after employee protests
Guardian:Microsoft deepened ties with Israeli military to provide tech support during Gaza war

Editing by Curt Milton. Read more at GeekWire.com.

A message from GeekWire co-founder Todd Bishop: This episode of the GeekWire Podcast is unlike any we&rsquo;ve done before. It touches on some of the most contentious and disputed issues in the tech industry, and in the world more broadly.&nbsp;
It started with my curiosity and desire to understand something that happened in March, at GeekWire&rsquo;s independent&nbsp;<a href="https://www.geekwire.com/2025/microsoft50-recap-company-faithful-mark-first-50-years-and-look-to-future-at-geekwire-event/">Microsoft @ 50 event</a>. I was on stage interviewing Microsoft Vice Chair and President Brad Smith when the conversation was interrupted by a protester.&nbsp;
The group behind the protest, called <a href="https://noazureforapartheid.com/">No Azure for Apartheid</a>, represents current and former Microsoft employees who want the company to end its cloud computing and AI contracts with the Israeli military. They cite concerns over how they believe their work is being used by Israel.
Addressing the larger issues raised by the group, Microsoft said in <a href="https://blogs.microsoft.com/on-the-issues/2025/05/15/statement-technology-israel-gaza/">a May 15 post</a> that it conducted internal and external reviews and &ldquo;found no evidence to date that Microsoft&rsquo;s Azure and AI technologies have been used to target or harm people in the conflict in Gaza.&rdquo;&nbsp;
After <a href="https://www.geekwire.com/2025/microsoft-no-evidence-israeli-military-used-its-technology-to-harm-civilians-reviews-find/">covering</a> Microsoft&rsquo;s statements and the group&rsquo;s response &mdash; and seeing the continued protests unfold at Microsoft events &mdash; I decided to dig deeper and learn more.&nbsp;
As part of that, I invited one of the organizers of No Azure for Apartheid to join me on this podcast, for a conversation about the motivations behind the group, their views on Microsoft&rsquo;s responsibilities, and how the tech industry intersects with international conflicts.&nbsp;
Our guest is software engineer Hossam Nasr, who was fired by Microsoft last year related to protests on the Microsoft campus. In fact, he was the first to protest inside the GeekWire event.
What followed was a complex conversation &mdash; one that at times went beyond Microsoft&rsquo;s role into broader political and ethical criticisms of Israel&rsquo;s actions in Gaza.&nbsp;
These are deeply polarizing issues, and we know there are strong, divergent opinions about them. I&rsquo;ve added context conveying Microsoft&rsquo;s responses, and noting areas where statements and characterizations about Israel, Palestine, and Gaza are the subject of dispute.&nbsp;
The conversation includes detailed descriptions of the ongoing conflict in Gaza and some historical comparisons that some listeners may find disturbing or offensive. And lastly, we recorded this conversation in late May, before the latest developments in the Middle East.
Related Links:&nbsp;
<ul>
<li>Microsoft: <a href="https://blogs.microsoft.com/on-the-issues/2025/05/15/statement-technology-israel-gaza/">Statement on the Issues Relating to Technology Services in Israel and Gaza</a></li>
<li>Associated Press: <a href="https://www.ap.org/news-highlights/best-of-the-week/first-winner/2025/as-israel-uses-u-s-made-ai-models-in-war-concerns-arise-about-techs-role-in-who-lives-and-who-dies/">As Israel uses US-made AI models in war, concerns arise about tech&rsquo;s role in who lives and who dies</a></li>
<li>AP: <a href="https://apnews.com/article/microsoft-fired-workers-israel-palestinians-gaza-72de6fe1f35db9398e3b6785203c6bbf">Microsoft fires employees who organized vigil for Palestinians killed in Gaza</a></li>
<li>+972: <a href="https://www.972mag.com/microsoft-azure-openai-israeli-army-cloud/">Leaked documents expose deep ties between Israeli army and Microsoft</a></li>
<li>The Verge: <a href="https://www.theverge.com/tech/672312/microsoft-block-palestine-gaza-email">Microsoft blocks emails that contain &lsquo;Palestine&rsquo; after employee protests</a></li>
<li>Guardian: <a href="https://www.theguardian.com/world/2025/jan/23/israeli-military-gaza-war-microsoft">Microsoft deepened ties with Israeli military to provide tech support during Gaza war</a></li>
</ul>
Editing by Curt Milton. Read more at&nbsp;<a href="https://www.geekwire.com/">GeekWire.com</a>.

Inside the Microsoft protests: Fired engineer on Palestine, Israel, AI, and big tech

Fifteen years ago, Steve Jobs and Apple had just introduced the first iPad, Steve Ballmer’s Microsoft had been left for dead, and nerdy online bookseller Jeff Bezos was still getting Amazon settled into its South Lake Union HQ. That’s when we started this podcast.

This week, we’re going back to 2010, revisiting clips from the earliest days of the show. We remember what was happening with Amazon, Microsoft, and Seattle’s startup scene, and try to wrap our heads around all the things that have changed since then.

With GeekWire co-founders Todd Bishop and John Cook.

Audio editing by Curt Milton.

 

Fifteen years ago, Steve Jobs and Apple had just introduced the first iPad, Steve Ballmer&rsquo;s Microsoft had been left for dead, and nerdy online bookseller Jeff Bezos was still getting Amazon settled into its South Lake Union HQ.&nbsp;That&rsquo;s when we started this podcast.
This week, we&rsquo;re going back to 2010, revisiting clips from the earliest days of the show. We remember what was happening with Amazon, Microsoft, and Seattle&rsquo;s startup scene, and try to wrap our heads around all the things that have changed since then.
With GeekWire co-founders Todd Bishop and John Cook.
Audio editing by Curt Milton.
&nbsp;

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

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