VCJ Cover Story: The Rise of the Celeb Investors

Life is imitating art on the TV show “Two and a Half Men,” in which actor Ashton Kutcher plays an Internet billionaire.

In real life, Kutcher is an Internet investor, with plenty of actual startups to his credit, including room rental service Airbnb, social magazine app Flipboard, travel search site Hipmunk and mobile marketplace provider Zaarly, among others.

Kutcher even has a healthy exit under his belt, from being part of the investment group in 2009, which included Andreessen Horowitz, that bought a majority stake in Skype from eBay for $2 billion. Earlier this year, Microsoft acquired Skype for $8.5 billion.

And the dude is not the only celeb with a taste for tech startups. As Tom Stein reports in the December issue of Venture Capital Journal that’s out today, Hollywood celebs are channeling their inner Mike Moritz as they take a stab at the venture capital game. Justin Timberlake is part of a group that recently paid $35 million to acquire MySpace; Lady Gaga and her poker face are betting on several music startups, including Backplane, a social platform that connects musicians and athletes with their fans; and the reality TV star Kim Kardashian is co-founder and creative director at fashion site ShoeDazzle, which earlier this year raised $40 million from several VC firms, including Andreessen Horowitz, Lightspeed Venture Partners and Polaris Venture Partners.

And everyone wants to know when Justin Bieber is gonna put his dollars to work and invest in a startup or two. Our best guess is when he turns 18.

From a VC perspective, it’s not hard to understand the attraction. Jeremy Liew, a managing director at Lightspeed Venture Partners and an investor in Los Angeles-based ShoeDazzle, tells VCJ that Kardashian’s participation in the company naturally made him more interested in the deal. The company, which has raised about $60 million in total funding, provides paying members access to women’s shoes, handbags and jewelry that are selected by Hollywood fashion stylists.

“It’s not just because Kim is a celebrity,” says Liew of his ShoeDazzle investment. “As long as there is a real affinity between the celebrity and the product being sold, it’s a great way to get people to pay attention.”

Not everyone is enamored. VC industry commentator Paul Kedrosky, a senior fellow at the Kauffman Foundation, says most celebrities are wasting their time and money. However, he tells VCJ that he is impressed with Kutcher, whom he says “actually seems to get it a lot more than many of the venture guys I know.”

To read more about celebrity investors, what VCs think about working with them, and to see a detailed list of which star is behind what startup, VCJ subscribers can click here for the full story.

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And if you want to chat more about celebrity gossip or other hot trends, send an email to Alastair Goldfisher at [email protected].

(Photo: A still from the TV show “Two and a Half Men,” starring Ashton Kutcher as Walden Schmidt. The laptop in the scene, which bears stickers of Kutcher’s investments, belongs to the actor, who reportedly angered his CBS producers by promoting his startups in this way.)

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