Mila Kunis recalled telling Ashton Kutcher to skip Uber, in an anecdote underscoring the risks of early-stage bets

A Yahoo Finance piece circulating in markets discussions drew attention to a striking celebrity finance anecdote: Mila Kunis, the daughter of a former cab driver, reportedly warned Ashton Kutcher that investing in Uber would be “the worst idea ever.” The story ties a personal perspective on ride-hailing with a broader lesson about how uneven the outcome can be when celebrities treat high-growth startups like a portfolio game.

According to the same Yahoo Finance report, Kutcher has a track record of backing companies through early investment vehicles and personal bets, with several of those positions later described as successful. The implication of the anecdote is less about any single investment thesis and more about the gap between skepticism at the time and what later becomes a mainstream business.

For Uber, the anecdote lands in a familiar setting. Ride-hailing is an industry that quickly moves from a disruptive pitch to a regulated operating model, with persistent public scrutiny around safety, labor classifications, data privacy, and the economics of rides in different markets. Even after becoming a widely known platform, Uber has faced ongoing market questions about profitability durability and the best path to sustainable margins.

The Yahoo Finance article also uses the Kutcher-Kunis contrast to highlight the tension between intuitive concerns and quantitative confidence. In this retelling, a cab-driver family background informs the skepticism, while Kutcher’s venture approach supports the counterpoint. Put simply, the story frames early-stage investing as a process where disagreement is normal, and the eventual winners can look obvious only in hindsight.

From a business perspective, Uber’s public-market footprint also makes the personal anecdote read like a case study in how risk changes with scale. Uber is now expected by investors to demonstrate consistent cash generation, manage regulatory exposure across cities and countries, and keep growing while controlling costs tied to drivers, incentives, marketing, and technology.

The caveat is that the Yahoo Finance excerpt available here is not itself a full disclosure of what was said in the moment beyond the reported characterization of the advice. It also does not provide details such as the timing of the conversation, whether the investment was at Uber’s earliest stages or a later round, or any specific valuation or instrument involved. Without those details, the anecdote should be treated primarily as a reported story about perception and timing rather than a documented investment record.

Still, the broader takeaway is relevant for markets watchers: as Uber’s scale has grown, so has the expectation that ride-hailing platforms can prove operational resilience, not just attract users. Celebrity and investor stories are entertaining, but they often obscure the hard parts of execution that determine whether a startup becomes a durable business.