Ashton Kutcher has played many roles in his lifetime.
You probably know some of them: Michael Kelso from “That ’70s Show,” Walden Schmidt from “Two and a Half Men,” and the star of dozens of movies, including “The Butterfly Effect” and “No Strings Attached.”
Others you might not be as familiar with. Before becoming famous, Kutcher worked jobs ranging from clean-up on construction crews to skinning and cleaning deer at a meat locker to baling hay.
More recently, he’s co-founded a human rights organization (THORN) , and a digital media company ( A Plus ), and, for the last several years, focused on one gig he seems particularly skilled at: startup investor.
In 2011, he co-founded venture capital firm A-Grade Investments, and in 2015, Sound Ventures, and has since poured millions into companies like Airbnb, Uber, and (ahem, full disclosure) Acorns. We talked with Kutcher about investing , financial firsts, and his best advice for living the life you want.
What inspired you to invest in startups?
I spend a lot of time thinking about new and simpler ways to do things, but don’t have enough time to execute on all those ideas. So I found people who were executing on them and invested in their success. What gets you excited about a particular company?
But the real thing that sweeps me away is when I get the feeling that something is obvious, and it just seems like, `Of course this is how we should be doing it!’ Or when an idea is so wonderful that you spend hours thinking about various iterations and applications. What do you consider your best investment?
Looking forward, what area of investing captures your imagination?
So, tell us about your first jobs.
What’s the first thing you saved for?
What was your scariest financial decision?
If you could impart some wisdom to your younger self, what would it be?
Optimism is priceless—but only when coupled with measurement. What would you tell someone who asks what they should invest in?
[Then] pay attention. If you work in a grocery store, pay attention to the items that you can’t keep in stock, and the new things that are hitting the shelf. If you are a contractor, investigate the new materials showing up on jobs. Who makes them? Why are they better? You may have a more educated opinion than you are giving yourself credit for. Too often, people speculate on investments based on what’s making someone else rich and forget to do a deep index on their own behaviors. Invest in that which you would like to see become a reality. Worst-case scenario, you lose money—but at least you will get the life you want.