Mila Kunis, a former cab driver's daughter, called Uber ‘the worst idea ever.’ Ashton Kutcher’s $500K stake in it grew to about $60M

Kit PulliamSun, October 18, 2026 at 11:30 AM UTC

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If you’re still kicking yourself for not buying Bitcoin early, at least you didn’t try to convince your partner not to invest in Uber early on.

In a past episode of “The Late Show With Stephen Colbert,” Mila Kunis told the story of when she tried to convince her now husband Ashton Kutcher not to invest in the rideshare behemoth.

“Early into our dating… he was like, ‘There’s this company, kind of like a cab company but anybody can drive the cab,’” Kunis told Colbert in 2021. “I was like, ‘That’s the worst idea ever.’”

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Kunis’ father was a cab driver, so she was doubtful it could work. She was worried that letting just anyone drive your cab was a bad idea.

Kutcher didn’t listen to her. And, in five years, by 2016, his stake in Uber grew from $500,000 to over $60 million.

How Kutcher and Kunis treat their investments now

Ashton Kutcher has a long, storied history in venture capital. He cofounded A-Grade Investments in 2010; this is the firm that invested in both Uber and Airbnb, another company Kunis once doubted.

“This happens all — there’s companies all the time that he’ll talk about that to me, seem ludicrous,” she told Colbert. “Why would I want to sleep on someone’s couch and pay for it? Like, it’s ludicrous. And yet, here we are.”

After A-Grade Investments, Kutcher went on to cofound venture capital firm Sound Ventures, too, before ultimately leaving the firm this year to start a new venture capital venture, The Wall Street Journal reported.

Kunis is perfectly happy that Kutcher ignored her advice on Uber and Airbnb (as well as Bitcoin, which she said sounded unsafe). But it would grate on any romantic relationship if one person in it was routinely ignored when it came to financial decisions.

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Luckily, Kunis and Kutcher don’t have that kind of relationship. Venture Capital is Kutcher’s job, and Kunis trusts him to make solo decisions there. But when it comes to personal investing as a couple, Kunis also has a rightful say.

“The best part about him is he’s really smart about including me in everything and making sure that I’m aware of everything that’s happening,” Kunis told Colbert. “If it’s coming out of our personal account, I do vet all the companies… but that’s for our personal investing, and then for the VC stuff, I am not the right person to ask.”

Read More: Here’s the average income of Americans by age in 2026. Are you keeping up or falling behind?

Don’t feel bad for missing out — VC busts far outweigh Uber-level successes

If you’re currently feeling more like Kunis than Kutcher when it comes to choosing your own investments, don’t feel bad — there are plenty of people in the same boat.

A working paper from the Stanford Graduate School of Business found that 90% of profits from investing come from only 5% of venture capitalists, and that less than 40% of VCs have ever had a successful investment. Generally, as a venture capitalist you can expect between 80% and 90% of your investments to fail.

In order to slog through investment failures and eventually reach success, you generally need lots of capital. As a successful actor, Kutcher had the funds to go into the VC world. Some of his other notable investments, outside of Airbnb and Uber, include Spotify, Skype and OpenAI.

While it’s less exciting than investing big money in the next big thing, having a diversified investment portfolio is a more surefire way of building wealth over the long term. You won’t multiply your investments by a ridiculous amount over five years like Kutcher did, but you’ll likely put yourself in a good place in time for retirement.

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Source: “AOL Entertainment”