Ashton Kutcher is back at his day job this week, playing "Internet billionaire with a broken heart" Walden Schmidt on the set of CBS’ Two and a Half Men.

It’s a case of art imitating life, minus the broken heart part, so long as you don’t believe any tabloid reports of occasional rifts between Kutcher and wife Demi Moore. Kutcher has been a Web entrepreneur for the past 11 years. He founded Katalyst Media in 2000, arguably his best venture to date, as it’s the only one still in operation. His Twitter following used to be legendary, until Justin Bieber and Lady Gaga surpassed him. And his 2008 Web Series Blah Girls debuted to much buzz and had two special fans—President Barack Obama and influential social-media guru Guy Kawasaki—but that too fizzled.

Still, that isn’t keeping his new bosses from giving him a chance. “There is great value in hiring Ashton Kutcher,” CBS Entertainment president Nina Tassler told reporters late Tuesday. “He is a talented, funny, gifted actor who comes with a tremendous amount of commitment and enthusiasm. He's given us an opportunity to move forward, to create an exciting new character."

When Men returns for its ninth season on September 19, Kutcher has a chance to tap the talents of an award-winning writing staff to map out his career and perhaps achieve what he hasn’t quite been able to in real life: success in his entrepreneurial ventures.

But it’s not going to be easy. First, Kutcher has the tough task of stepping into the black hole left by Charlie Sheen, who crashed and burned out his best-paid-TV-actor role on the popular show after a months-long alcohol, cocaine, and hooker/goddess binge.

Kutcher, by all accounts, has been a relatively good guy, staying out of Sheenesque troubles. But when it comes to his business dealings, he hasn’t been #winning. Even his recent investments (take his involvement in vacation-rental hotshot Airbnb, for example) have been fraught with tabloid-like troubles. Since he signed on to advise the company and put in an undisclosed amount of money—although press releases said it was Kutcher’s biggest-ever investment—Airbnb has been accused of using Craigslist to inflate its rental numbers and has had to deal with Ransackgate, an embarrassingly and poorly handled situation in which a renter allegedly vandalized an apartment listed on the site.

If he could write a script for his business dealings, Kutcher would likely change a few details.

But even back in May, perhaps before he knew what his character would be doing, Kutcher talked about similarities between running a startup and acting—insights he’s drawing upon as he prepares to play Schmidt (we don’t know yet if he’s reached out to the other Schmidt—Eric—of Google fame, yet), no doubt. In entrepreneurship, like in method acting, you have to get to know your founders: how they think, how they approach problems, and how they interact with others.

Who knows? Maybe Walden Schmidt will start a venture on the show that will translate to real profits, and Ashton Kutcher will see life imitating art.

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