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Box Founder Aaron Levie Warns Tech CEOs of 'AI Psychosis' – Why Hands-On Experience Is Critical



By admin | May 31, 2026 | 5 min read


Box Founder Aaron Levie Warns Tech CEOs of 'AI Psychosis' – Why Hands-On Experience Is Critical

This week, Box founder Aaron Levie sparked a conversation with a social media post suggesting that tech CEOs are “uniquely prone to AI psychosis.” On one hand, he’s not rejecting AI tools outright—he’s simply arguing that CEOs need to actually use these tools to truly understand them. That’s a relatively mild critique compared to other signs of a growing backlash. Consider graduating college students booing any mention of AI, the negative sentiment around tech industry layoffs, or the noticeable spike in installs at search engine DuckDuckGo following Google’s announcement that it’s integrating more AI into search. Kirsten noted that Google faces a dilemma: it’s “chasing that thing it feels like it has to do to keep up, but it’s messing with the thing that people attach to the brand the most, and it’s not improving it.” More broadly, she wondered “if this anti-AI moment is an opportunity for startups or other areas of business.”

Here’s a preview of our discussion, edited for length and clarity.

Anthony Ha: AI is incredibly polarizing. That’s part of what makes it so hard to talk about—you can feel a little crazy because everyone’s using it and loving it, yet simultaneously no one’s using it and everyone hates it. There are large groups where both of those things are true. On the user side, one striking thing we’ve already covered is Google’s search announcements and how AI is becoming a bigger part of search—though it’s interesting to see Google trying to walk that back a bit, or at least add nuance, like offering ways to still get the classic 10 blue links experience. It’s not going away entirely. But many people aren’t thrilled with Google’s direction. For instance, DuckDuckGo reported a 30% increase in installs—a huge jump. Of course, DuckDuckGo is much smaller than Google, so Google isn’t in immediate trouble, but it signals a significant audience that dislikes the current AI trajectory.

Sean O’Kane: One thing I keep noticing when I look at leading AI labs or tech companies pushing AI features is a trend toward Anthropic’s approach—really trying to understand what you want to offer and sticking to that. Google, however, seems to be pushing the other direction. They’re trying many things, but they don’t help themselves by being so vague. When Google goes on stage at IO and talks about changing search, so much of what they discuss revolves around shopping or commercial transactions. But many of us, especially those who’ve used Google for decades, think of it as an information retrieval system. Google often struggles with that: they get reactive fears about damaging information retrieval, and their response is, “Yeah, but that’ll still be there. Let’s focus on how it helps you book a flight.” Then they shoot themselves in the foot by releasing systems that haven’t been stress-tested enough, running into the same problems they’ve faced for years.

Kirsten Korosec: We just published a great article about how Google can’t even spell its own name—ask it how many P’s are in “Google,” and it says two. This tension is real: Google is chasing what it feels it must do to keep up, but it’s messing with the core of its brand without improving it. I’m wondering, beyond people voting with their clicks by switching services, if there are opportunities for startups or other areas of business in this anti-AI moment.

Anthony: Absolutely. It’s probably a challenge because opinions vary so widely. If you build something for the AI-skeptical crowd, you might alienate more evangelistic users. But that’s the moment we’re in. Look at how DuckDuckGo promotes itself—it’s very anti-AI, which I find striking. A year ago, when I started moving away from Google and trying other search engines, even alternatives were experimenting with AI features because they felt they had to. Now, they see a lane to say, “No, we’re just not interested in that stuff, or if we do it, it’s in a separate sandbox that won’t affect your core search experience.”

Kirsten: I think we sometimes unfairly categorize all tech CEOs as force-feeding people AI. At least one CEO has said, “I think there’s a bit of psychosis among other tech CEOs around AI.” He noted that CEOs are “uniquely prone to AI psychosis because they’re sufficiently distant from the last mile of work that still has to happen to generate most value with AI.” I found that really interesting. I wonder if other CEOs agree, and if they’re also thinking about how their workforce is changing—our other topic today, which isn’t just about the AI divide but also how AI is changing work. We’ve seen the bad side with layoffs, but also big changes in how people work. In your coverage areas, are you seeing evidence of that? I don’t think it’s limited to the “AI startup sector” or big tech.

Sean: For the companies I cover—many working on physical transportation or adjacent fields—change has been slower than on the software side. But we’re starting to see shifts. We’ve talked about Mind Robotics, the spinout from Rivian CEO RJ Scaringe. More AI is being applied to physical infrastructure, manufacturing, robotics, and self-driving. But the software side is where it’s really changing things, especially for people whose jobs are directly tied to producing code.

Anthony: Part of the question involves both AI adoption in companies and AI-driven layoffs—are they top-down or bottom-up? Many workforce transformations over the last couple of decades have been at least somewhat bottom-up: tools people like to use, which they bring in, and then executives accept. But there’s a sense that the belief in AI productivity gains is embraced by executives—or, at startups, by VCs funding them—who love the dream of having a tiny team as effective as a much larger one. That’s not impossible, but Aaron’s point is that if you’re not touching the end work, how would you know? He’s not saying throw out all AI tools, but that you have to use them and understand what they do—you can’t just look at a slide and say, “Yes, incredible efficiency, let’s go.”

Kirsten: There’s a lot of real evidence that companies are using these tools, and it’s directly affecting workers through layoffs and changes in how they work. Both truths are accurate here.




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