For the past two decades and change, he has been one of the biggest names in Hollywood. However, it would be a disservice to the person Ashton Kutcher to typecast him as “just” another Hollywood star. He’s an active angel investor in numerous tech start-ups, works on content production for Netflix and founded a non-profit dedicated to combatting child sex trafficking. These divergent areas of activity coupled with his Hollywood bonafides make him an engaging and entertaining guest for the OMR Podcast with Philipp Westermeyer. In this episode, the pair discuss Kutcher’s career on and off the silver screen, while also discussing in-depth Kutcher’s successes and failures as an investor, why even failed investments are a net positive, which social networks he currently sees potential in and why he recently reached out to a German politician on Twitter.

“I auditioned for one show. The producers told me I wasn’t funny. Then my manager to me to go read for that other show you read for. […]I got that job,” Ashton Kutcher tells Philipp Westermeyer in the OMR Podcast. That job he’s talking about is none other than “That 70’s Show” (also his breakthrough role and first job as an actor). Kutcher, as most know, played the lovable and lost Michael Kelso alongside his now wife Mila Kunis. The show propels him into popularity; after stepping off the the small screen and onto the silver screen with roles in “Dude, Where’s My Car?,” “The Butterfly Effect” and “No Strings Attached,” he’s a genuine Hollywood movie star. For four seasons, he stars alongside Charlie Sheen in “Two and a Half Men,” where he reportedly earns a cool 750k per episode.

If you only look at your returns, you lead a boring existence

By this point, Kutcher is already investing the money he earns as an actor in numerous startups. At first as an angel investor, later as a co-founder of venture capital fund A-Grade Investments and currently Sound Ventures. With an excess of three billion invested dollars, he is considered the most active and prolific Hollywood investor. He lands his first successes with early investments in Airbnb, Uber, Spotify and Warby Parker. Despite the success, Kutcher has remained modest, and a bit self-deprecating, saying that he’s probably the worst venture capitalist on the planet.

He’s never really paid attention to returns on his investments, but rather focussed on working with interesting, innovative individuals. “Capital returns are like the contrails of being an investor. When you’re the pilot of a plane, you are trying not to hit the mountain in front of you. You are not looking back at the exhaust,” says Kutcher. “If you only focus on returns, you lead a pretty boring existence.” He says that he on average he invests between two and five million dollars and focuses on companies whose core product or service is market-ready.

No ROI, no problem

Like any other venture capitalist, Kutcher’s career as an investor has not been only home runs. In our home market of Germany alone, investments in opinion platform “Amen” (2011), “Go Butler” (2015) and even Soundcloud (2011) fail to produce the desired returns.

Nevertheless, Kutcher does not see his investments in Germany as failures. In the case of Amen, he says that “just because an idea doesn’t work, does not mean that it wasn’t successful,” he says. “Should we have pivoted earlier? Yes. But we saw signals that it was working. It didn’t, but I met some extraordinary people.” And to be fair, it’s not all been bad. Sound Ventures took part in an early USD 28m financing round in Berlin insurance startup Wefox. In the meantime, the company has acquired an additional USD 235m—with additional capital coming from Sound Ventures. Perhaps he’ll finally have a successful investment in Germany.

To hear Kutcher’s thoughts on the future of hype topics du jour Clubhouse, Bitcoin and NFTs, why Community is the social platform that plays the biggest role in his life and why he contacted German politician Saskia Esken, check out this episode of the OMR Podcast with Philipp Westermeyer.