{"id":6254,"date":"2026-08-30T10:11:29","date_gmt":"2026-08-30T10:11:29","guid":{"rendered":"https:\/\/crosscountrymovingteams.com\/?p=6254"},"modified":"2026-08-30T10:11:29","modified_gmt":"2026-08-30T10:11:29","slug":"why-the-ai-economy-is-like-a-bad-dating-app-drowning-in-decks-pilot-purgatory-and-its-playing-out-like-the-dotcom-bubble-except-worse","status":"publish","type":"post","link":"https:\/\/crosscountrymovingteams.com\/?p=6254","title":{"rendered":"Why the AI economy is like a bad dating app \u2014 drowning in decks, pilot purgatory \u2014\u00a0and it\u2019s playing out like the dotcom bubble, except worse"},"content":{"rendered":"
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Webb, 51, runs the Future Today Strategy Group, the foresight and consulting firm she founded in 2006 after a career in data journalism that led to her subsequent interest in machine learning. Webb, who also teaches at NYU\u2019s Stern School of Business, published The Big Nine<\/em>, which named nine American and Chinese tech giants as forces that would dominate in a world marked by artificial intelligence and a full-scale tech cold war, so she\u2019s used to being ahead of her time, and she\u2019s used to being frustrated by the world being behind the schedule she sees in her head.<\/p>\n

Read more Why Gen X should stop planning around an inheritance that may never arrive<\/a><\/p>\n

So when Webb told Fortune<\/em> that she sees something like a bust coming for corporate AI spending, it\u2019s worth pausing on the precise dynamic she\u2019s describing. \u201cAI is making production cheap,\u201d she said, \u201cbut it\u2019s making everything else in companies much more expensive.\u201d The corporate world, she added, is going through something like what millennials and Gen Zers experienced as dating-app fatigue.<\/p>\n

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\u201cThe best thing [for a dating app] is to never get married,\u201d Webb said, adding that she sees the same thing playing out in the endless series of generative AI pilots. She said executives tell her they\u2019re in \u201cpilot purgatory\u201d: dealing with unending pilots and \u201cenormous productivity but [they\u2019re] not sure what to do with that.\u201d<\/p>\n

Venture capitalist Marc Andreessen, meanwhile, said in March that large companies are overstaffed by as much as 75% and were using AI as a \u201csilver bullet excuse\u201d for cuts that reflect pandemic-era overhiring. A separate analysis by Oxford Economics found AI-cited layoffs accounted for a mere 4.5% of total U.S. job losses despite outsized headlines.<\/p>\n

\u2018It feels like you\u2019re buying abundance\u2019<\/h2>\n

Webb, who speaks with between 100 and 150 CEOs a year, said she\u2019s most focused on a bubble that sits apart from what\u2019s happening on Wall Street: the strange way that AI is deforming work without actually changing it much at all.<\/p>\n

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\u201cIt feels like you\u2019re getting a lot when you invest in AI,\u201d Webb said, \u201cit feels like you\u2019re buying abundance. But that abundance ends up costing much more down the road.\u201d It\u2019s not a question of long-term investment versus short-term gains, an old business trade-off. \u201cThis is immediate satisfaction, followed by: can I productize this? Can I put it in a workflow?\u201d AI is making companies feel like they\u2019re winning, a sensation of \u201cI\u2019m getting away with it,\u201d and that\u2019s driving a lot of enthusiasm and adoption. <\/p>\n

At the same time, she said she can count on one hand the number of companies that have figured out a sustainable way to pull off this kind of experimentation. One of her clients had run 14 or 15 generative AI\/agent pilots since the start of the year and used Amazon\u2019s famous two-pizza rule, in which no team was big enough that it would take more than two pizzas to feed them. None of them scaled. \u201cThey\u2019ve gone through a lot of pizza.\u201d Part of the issue is that pilots often run without integration into legal and IT, and so executives don\u2019t embed the pilots into their infrastructure, but restart from zero each time. \u201cThat costs a lot of money,\u201d she said.<\/p>\n

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The pattern shows up in the data: A Bain & Company survey of 951 global companies published in June found that nearly 40% of companies that measured their AI cost savings landed below 10%, despite having targeted returns of 11% to 20%. But to Webb\u2019s point, the shortfall hadn\u2019t slowed spending, as 90% of companies surveyed said they\u2019re increasing their AI budget anyway.<\/p>\n

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Drowning in decks<\/h2>\n

Outside of pilot purgatory, there\u2019s the drowning-in-decks issue. Webb recalled an executive who recently shared that their direct reports were experiencing something like decision paralysis, \u00a0not because they had too little information, but because they were being buried in too much analysis to process. Another described the problem to Webb as \u201cinsta-decks\u201d: presentations that used to take a week to build now take a day, but the same team is receiving five times as many of them. It doesn\u2019t help, she added, that \u201cClaude has a little bit of a verbosity problem,\u201d producing 10 pages when you only need one.<\/p>\n

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\u201cThe more a company uses these tools,\u201d Webb added, \u201cthe more generic ideas are spit out.\u201d This isn\u2019t the same thing as AI slop, she said \u2014\u00a0it\u2019s something different. \u201cIt\u2019s fine with me if something was not written necessarily by a person, if the rest of the information is useful.\u201d <\/p>\n

Read more America\u2019s Mediterranean lunch bowl is booming as NAYA races toward 200 restaurants<\/a><\/p>\n

Webb said she asks nearly every CEO she meets: if AI freed up 10% of your total capacity tomorrow, where would you deploy it? \u201cSo far, I haven\u2019t gotten an answer.\u201d Of all the time being saved, she said, nobody seems to have the job of harvesting all these productivity gains. \u201cI\u2019d bet at most companies, people are prioritizing speed over creating new ways of thinking. And then you\u2019re not learning anything.\u201d<\/p>\n

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Psychologists have begun studying the phenomenon of \u201ccognitive offloading\u201d\u2014delegating mental work to a tool rather than doing it yourself\u2014and recent research finds that when AI takes over core reasoning tasks, people\u2019s sense of ownership over the resulting work declines. It\u2019s \u201cautomating something that people very much feel they have ownership over,\u201d Webb said, adding that you can see this in debates in Hollywood and the media over where true creativity is headed. From a business perspective, she stressed, \u201cAI is cheap to get started with,\u201d but then the costs start to compound in ways that quickly get \u201cshockingly uncomfortable.\u201d<\/p>\n

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When will the reckoning happen?<\/h2>\n

Webb said she expects the reckoning as early as next year. \u201cRight now, very few companies are in a position to show an actual measurable change in the next two quarters,\u201d she said, calling it the \u201csecond chapter\u201d of the story playing out now. \u201cWe might start to see cracks happen with missed targets\u201d as Wall Street starts asking about all of the generative AI pilots in the enterprise, and wanting to see results.<\/p>\n

At the same time, she resisted the tidy bubble framing. \u201cThis is not a normal dotcom bubble and burst,\u201d she said. \u201cAll of this abundance and productivity comes at a new cost that people aren\u2019t factoring in.\u201d <\/p>\n

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Part of what\u2019s colliding here, Webb added, is generational and emotional, not just financial. She was working in journalism when the commercial internet first really switched on and remembers how \u201ca lot of people were demoted to digital\u201d in that earlier transition, without much intentional planning behind that decision. She sees a similar dynamic playing out now\u2014the people steering the AI revolution aren\u2019t the ones equipped to really know what they\u2019re dealing with. <\/p>\n

A big part of the problem, Webb explained, is that the boards and executives under pressure to adopt AI \u2014\u00a0and do it yesterday \u2014\u00a0have spent the past several decades developing expertise in fields that have nothing to do with it. \u201cNo CEO was hired because they\u2019re an expert in artificial intelligence,\u201d she said. \u201cThese people are heads of organizations because they\u2019re excellent executives,\u201d and AI is nearly the worst possible technology for them to grapple with. \u201cAI is not one technology, it\u2019s an umbrella for many technologies,\u201d she said, and \u201cplanning requires data \u2014\u00a0you can\u2019t just go with your gut on this stuff.\u201d<\/p>\n

Every new technology wave feels disorienting in the moment, and the people who don\u2019t feel fluent in it tend to resist it, she added. And the people most likely to feel that way are the older and more expensive workers who are also the most likely to be laid off.<\/p>\n

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If this mismatch between pressure, inexperience and misleadingly expensive technology persists, she added, the outcome could be far worse than just a market crash. \u201cThis isn\u2019t like the economy takes a hit. It\u2019s like the economy makes weird decisions.\u201d When Fortune<\/em> asked if she\u2019s describing an AI hallucination on an economywide scale, she laughed and said, \u201cI\u2019m going to start using that in class.\u201d <\/p>\n

Her own business, by the way, has never been doing better. \u201cWhen there\u2019s horrific uncertainty out there,\u201d she said, \u201cuncertainty is what we do.\u201d<\/p>\n

Read more Former White House teleprompter operator\u00a0must turn over more than $100,000 in profits and pay a $65,000 fine in insider trading settlement<\/a><\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

Amy Webb is a futurist who called the rise of AI \u2014\u00a0and a U.S.\/China tech Cold War \u2014\u00a0years ago. 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