Does your CEO have AI psychosis? Aaron Levie thinks most of them do. episode artwork

EPISODE · May 29, 2026 · 38 MIN

Does your CEO have AI psychosis? Aaron Levie thinks most of them do.

from Equity · host TechCrunch, Rebecca Bellan, Kirsten Korosec, Anthony Ha, Sean O'Kane, Theresa Loconsolo

The people deciding that AI can replace your job are also the ones least likely to understand what your job truly involves, according to Box founder Aaron Levie, who pointed to this as an example of "AI psychosis.” Indeed, ClickUp recently cut 22% of its workforcefor AI agents, tech layoffs in 2026 are already nearly matching all of 2025, and DuckDuckGo installs are climbing from users who want Google to stop forcing AI into search and just give them links.  On this episode of TechCrunch's Equity podcast, Kirsten Korosec, Anthony Ha, and Sean O'Kane dig into what happens when the AI-pilled and the AI-skeptical are both right at the same time, plus three deals worth knowing about and Waymo's new robotaxi hitting the road.  Listen to the full episode to hear:  Kirsten's first look at Waymo's new Ojai robotaxi in Phoenix, and the crew's thoughts on the company's path to profitability  Cloud data storage giant Snowflake’s $6 billion five-year agreement with AWS  Why Stord, the "anti-Amazon" fulfillment startup, just raised $250 million at a $3 billion valuation  What OpenRouter's $113 million raise says about the picks-and-shovels layer, and how long that interest lasts  How the AI agent wave is actually reshaping hiring, not just headcount  Subscribe to Equity on YouTube, Apple Podcasts, Overcast, Spotify and all the casts. You also can follow Equity on X and Threads, at @EquityPod.  Chapters:  00:00 Intro  01:18 Waymo's new Ojai robotaxi  06:41 Stord raises $250M to take on Amazon fulfillment  12:46 Snowflake signs $6B deal with AWS  15:39 OpenRouter raises $113M Series B  20:07 The AI divide & anti-AI backlash  27:31 AI psychosis & how AI is reshaping headcount and hiring  37:04 Outro  Learn more about your ad choices. Visit megaphone.fm/adchoices

The people deciding that AI can replace your job are also the ones least likely to understand what your job truly involves, according to Box founder Aaron Levie, who pointed to this as an example of "AI psychosis.” Indeed, ClickUp recently cut 22% of its workforcefor AI agents, tech layoffs in 2026 are already nearly matching all of 2025, and DuckDuckGo installs are climbing from users who want Google to stop forcing AI into search and just give them links.  On this episode of TechCrunch's Equity podcast, Kirsten Korosec, Anthony Ha, and Sean O'Kane dig into what happens when the AI-pilled and the AI-skeptical are both right at the same time, plus three deals worth knowing about and Waymo's new robotaxi hitting the road.  Listen to the full episode to hear:  Kirsten's first look at Waymo's new Ojai robotaxi in Phoenix, and the crew's thoughts on the company's path to profitability  Cloud data storage giant Snowflake’s $6 billion five-year agreement with AWS  Why Stord, the "anti-Amazon" fulfillment startup, just raised $250 million at a $3 billion valuation  What OpenRouter's $113 million raise says about the picks-and-shovels layer, and how long that interest lasts  How the AI agent wave is actually reshaping hiring, not just headcount  Subscribe to Equity on YouTube, Apple Podcasts, Overcast, Spotify and all the casts. You also can follow Equity on X and Threads, at @EquityPod.  Chapters:  00:00 Intro  01:18 Waymo's new Ojai robotaxi  06:41 Stord raises $250M to take on Amazon fulfillment  12:46 Snowflake signs $6B deal with AWS  15:39 OpenRouter raises $113M Series B  20:07 The AI divide & anti-AI backlash  27:31 AI psychosis & how AI is reshaping headcount and hiring  37:04 Outro  Learn more about your ad choices. Visit megaphone.fm/adchoices

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Does your CEO have AI psychosis? Aaron Levie thinks most of them do.

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The Syndicate Blogcast: Startups | Startup Investing | Tech News | Angel Investors | VC | Venture Capital | Private Equity | Crowdfunding | Fundraising Matt Ward - Serial Entrepreneur | Angel Investor | Startup Advisor | Amazon Ecommerce The Syndicate Blogcast show is an extension of The Syndicate podcast, featuring long form articles on the future technology, ecommerce, business and life. The mini-sodes deconstruct high level startup, business and tech issues to help investors and operators better understand and win the market. Recurring topics include: Facebook, Google, Amazon, Apple, Ecommerce, Blockchains, ICOs, Cryptocurrencies, Marketing, Fundraising, Venture Capital, Startup Challenges, Business Development and more. The Blogcast comes in addition to The Syndicate - the place where investors and startups combine to create crazy businesses and even crazier returns. The Syndicate podcast is a deep dive on the angel investors and VCs behind the big name startups. We interview the best and brightest investors, syndicate leads, GPs, limited partners and startup founders to create an original, off the cuff discussion on startup investing. The Future Of Work Collective Podcast Lucy Mundy Work isn't working anymore.The dissatisfaction people felt with the modern workplace was exacerbated by the pandemic, and nobody wants to be worse off after enjoying new freedoms and flexibilities. But bosses want people back in the office. Workers are striking for fairer conditions. Trust in staff is at an all time low. Economic pressures are in danger of pushing diversity, equity, and inclusion down the employment agenda. Bullying and stress are rife. We can't carry on like this. We need your help. Whether you're a cashier in Blackburn, an HR manager in Thurrock, or a farmer on Shetland - we need to listen to everyone about what the future of work should look like. This is a collective of people from different backgrounds, some of whom are experts in talking about work, and all of whom care about finding positive solutions. On our podcast, we discuss how we take action now to make work better for everyone. Modern Mindset Christopher Smith Modern Mindset with Christopher Smith is a must-listen podcast that delves into finance, private equity, real estate, and investment tips. WIth a professional and dynamic voice, it offers invites on emerging trends, market strategies, and the latest industry innovations. Tune in to stay ahead and transform your investment approach! Workforce Insights with Employ Milwaukee Employ Milwaukee Milwaukee’s workforce development ecosystem constantly adapts to change as it responds to economic disruptions, new technologies, socioeconomic disparities, and now the impact of a global pandemic.  Over the next decade, change will be even more dramatic, opening a whole new spectrum of possibilities around the notion of work and what both workers and employers need to be successful. Join workforce leaders from the public and private sectors, as they discuss insights, trends, challenges, and solutions. If you want to learn more about the opportunities we can embrace to ensure equity, expand job readiness, and catalyze collaboration among stakeholders, this podcast is for you!Hosted by Ausha. See ausha.co/privacy-policy for more information.

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This episode was published on May 29, 2026.

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The people deciding that AI can replace your job are also the ones least likely to understand what your job truly involves, according to Box founder Aaron Levie, who pointed to this as an example of "AI psychosis.” Indeed, ClickUp recently cut 22%...

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