When the day job isn't the whole job
You know the celebrity for one thing. Acting, singing, sports. But some of them have been running businesses you'd never guess, and not all of them are vanity brands. Some are real operations that started as genuine interests and became something more.
Here are the celebrity side businesses that actually surprised people.
The ones that make you look twice
Ashton Kutcher — tech investor. This one is well-known now, but it was surprising when it started. Kutcher was early to Silicon Valley investing, getting in on Skype, Airbnb, and Uber before they went public. He co-founded A-Grade Investments and Sound Ventures. The man from "That '70s Show" and "Punk'd" is a legitimate venture capitalist. The portfolio reportedly includes over 70 companies. He wasn't just a famous face on a term sheet — he actually understood the deals.
Natalie Portman — production company and activist. Portman has been quietly producing films through her company MountainA, and she's been a serious advocate for animal rights and environmental causes. She produced and narrated "Eating Animals" (2017), a documentary about factory farming. The business and the activism are the same thing, which is the interesting part.
Mark Wahlberg — fitness franchise and car dealerships. Wahlberg has been open about his daily 4 AM workout routine, and he turned it into a business. He's an investor in F45 Training, a fitness franchise with locations worldwide. He also owns or has owned car dealerships in Ohio and a stake in a tequila brand. The man is diversified in a way most actors never bother with.
The musicians who went technical
Will.i.am — tech entrepreneurship. The Black Eyed Peas frontman has been building tech companies for years. He founded i.am+, which developed smartwatches and AI products. He's invested in multiple tech startups and has been involved in AI and wearables. Whether every venture succeeded is beside the point — he's been in the room for real tech conversations, not just celebrity tech endorsements.
Linkin Park's Mike Shinoda — art and design. Shinoda has been doing visual art alongside music for his entire career. He's designed album art, merchandise, and gallery pieces. He's also been involved in music production software and education. It's a genuine creative business, not a side hustle.
The athletes who didn't just invest
LeBron James — production company and retail. James didn't just put money in companies — he built SpringHill Company, a production outfit that produced "Space Jam: A New Legacy" and the "Shop" talk show. He's also an investor in Blaze Pizza, which grew from a small chain to a national franchise. His net worth crossed the billion-dollar mark in 2022, making him the first active NBA player to reach that figure. The basketball is the platform. The businesses are the empire.
Serena Williams — venture capital. Serena Ventures, launched in 2014, has invested in over 60 companies. She's focused on founders who are women and people of color, which is both a real business strategy and a genuine mission. She's not just a famous name on a fund — she's been clear that she studies the companies and makes the decisions.
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The actors who went agricultural
Brad Pitt — wine. Pitt became involved in the Miraval estate in Provence, France, through his partnership with the Perrin family. The wine — a rosé — became a genuine critical success, not just a celebrity label. It's sold in real wine shops and reviewed by real critics. The estate has been producing wine since before his involvement, and the Perrin family brings the expertise. But Pitt's involvement was real, not just promotional.
Kris Kristofferson — helicopter pilot. Before he was a songwriter and actor, Kristofferson was a helicopter pilot. He famously flew helicopters to support himself while trying to break into the music industry in Nashville. That's not a side business in the modern sense, but it's the spirit of the thing — the day job you'd never connect to the career.
The ones that are just honest work
Not every celebrity side business is a genius play. Some are just people who like doing something and found a way to make it real.
Nick Offerman is a woodworker. He runs a real woodshop, Offerman Woodshop, in Los Angeles, producing handcrafted furniture and goods. It's not a celebrity brand — it's a real shop with real craftspeople. He wrote a book about it ("Good Clean Fun") and the shop has a real waitlist.
What People Actually Ask
Which celebrity investor is actually serious about it?
Ashton Kutcher and Serena Williams are the two most credible celebrity investors. Both have track records, real portfolios, and are known in the VC community as people who actually study deals, not just lend their names. LeBron James and Nas have also built serious investment reputations.
Are celebrity side businesses usually successful?
Most aren't. The ones that succeed are the ones where the celebrity has genuine involvement and interest. Ashton Kutcher learned the VC business. Serena Williams studies her portfolio. Nick Offerman actually runs a woodshop. The ones that fail are licensing deals where the celebrity shows up for the launch and nothing else.
What is the most surprising celebrity side business?
Brad Pitt's wine is the one that surprises people most, because it's a genuinely good product that stands on its own in the wine world. The Miraval rosé is served in real restaurants by real sommeliers. That's rare for a celebrity-branded product.
Do celebrities actually run these businesses or just invest?
It runs the spectrum. Some, like Nick Offerman's woodshop, are hands-on. Others, like many celebrity tequila brands, are licensing deals where the celebrity is an investor and a face. The ones that last tend to be the ones with real involvement.
