When Maverick’s Guy Oseary, 44, wasn’t busy building music’s pre-eminent management firm, he and partner Ashton Kutcher were parlaying early investments in Spotify, Uber and Airbnb, among others, into a $250 million portfolio.

What was your first investment?
When I was 27, I invested in an incubator called Idealab. It was right before the tech bubble burst, so that’s how that went.

What did that teach you?
To diversify. When I came back into investing about eight or nine years ago, I made two bets: one offline -- Vita Coco coconut water -- and one online, with Groupon.

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Who do you look up to in the investment space?
My partner, Ashton Kutcher, is a great investor. Smart as hell and very intuitive. He has an engineering background, so he understands the deep tech side of things. I don’t have that. I can name any song from the ’80s in the first two seconds, but that’s not going to move the deal.

So what do you bring to the partnership?
I’m just a really good-looking guy next to Ashton. (Laughs.) I bring my A&R instincts. Engineers and founders are the rock stars of today. They have a vision. They have a voice. My job is to identify that and help them reach an audience.

If someone were to bring you an idea for a new streaming service today, would you be interested?
Now? I think it’s a little late in the U.S. and Europe. I’m a passionate believer in India, so we’re backing [streaming service] Saavn in a big way. But it’s very hard to build a streaming service. It’s not easy to get people to pay.

Any investments in virtual reality?
We have a lot of investments in VR technology and platforms. But it’s a very complicated concept at this stage. It’s still early days.

Is there a particular investment that you should have made but didn’t?
A friend of mine started WeWork, and I didn’t invest. I loved the concept, too: It’s about sharing of services, location, support — it’s everything I love. And it’s now worth 20 billion dollars. What was I thinking?

This article originally appeared in the March 18 issue of Billboard.