Acting background helps Ashton Kutcher pick investments

By A. James Memmott

May 27, 2011 at 8:13am

People looking to diversify their stock portfolios probably don’t go to Charlie Sheen for advice.

But they could do worse than pick the brain of Ashton Kutcher, Sheen’s replacement on “Two and a Half Men.”

The New York Times and other media reported this week that Kutcher has made several canny investments in tech start-ups, including Foursquare, the location-based social-networking site, and Skype, the Internet phone service recently purchased by Microsoft for $8.5 billion.

Ashton Kutcher
Ashton Kutcher

Kutcher also has put money into Flipboard, an app for the iPad that aggregates content and puts it into a magazine format. And he’s invested in Path, an app for sharing photos and videos.

Some of Kutcher’s investments are now made through A Grade Investments.

Kutcher formed A Grade along with Ronald W. Burkle, the billionaire investor and Democratic political fundraiser, and Guy Oseary, who manages Madonna and baseball star Alex Rodriguez, among others.

Both Kutcher and his wife, the actress Demi Moore, are clients of Untitled Entertainment, an agency in which Oseary is a principal.

Kutcher talked with Charlie Rose about his investments at the TechCrunch Disrupt conference this week in New York City.

He acknowledged that he hasn’t always guessed right in investing.

Kutcher lost money on Ooma, an Internet phone company that failed. Similarly, he backed Blah Girls, a web comedy for young women that failed.

But Kutcher struck gold in 2009 when Marc Andreessen, who had founded Netscape, asked him to put money into Skype. Estimates are that the sale of Skype to Microsoft earned Kutcher three times his investment.

One key to Kutcher’s success may be that he plays to his strengths and compensates for his weaknesses.

He’s knowledgeable about social media with 6,800,000 followers on Twitter and 9,800,000 fans on Facebook.

And his day job does help him in choosing investments.

“As an actor, when we receive a script, we start breaking down every character by their want,” he told Rose. “Every character has an objective and a super objective. I look at technology the same way. I’ll think, ‘I’m a user of this platform. What do I want and how badly do I want it?”

But Kutcher admits that he needs help when it comes to the inner workings of investing.

“That’s why I have a lot of friends who are a lot smarter about those things than I am. … Let them be smart about that,” he told Rose.

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  • #1.   NeoPhyte 05.27.2011

    Hmmm…Ooma Ranked #1 by Consumer Reports May 2011 issue

    …sounds like Ashton is batting 1000 and this “journalist” (really?) needs a ‘fact checker’:


    - The Phyte

  • #2.   Laurie Bennett 05.28.2011

    “Failed” certainly doesn’t mean no longer in existence. (Check out the number of headlines describing GM as failed in 2009.)

    And we’re certainly not the first to describe Ooma as a bad investment at the time Kutcher put money into the company.

    As the NYT notes: “Mr. Kutcher’s first forays into the tech industry were flops: an Internet calling service called Ooma in 2007, and an animated Web comedy show aimed at young women, called the “Blah Girls,.” in 2008.”

    And there’s this from Apple News: “Kutcher admitted to Rose that his first foray into startups with the fated Ooma, an internet-based phone company in which Kutcher both invested and served a managerial role, failed in 2004.”

    While we’re not privy to all the details of Kutcher’s investment, the bottom line according to Kutcher is that it didn’t pay off.

    Ooma has received significant funding in the years since, and continues to operate.

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