Celebrities. They’re just like us, except they look nicer, smell better, and can nab a table at Red Lobster during Endless Shrimp without having to wait. They also have the funds to freely test out their crazy business ideas—which more often than not, fail spectacularly.

But sometimes the lightning of fortune strikes twice, gracing already blessed talents with Gary Dahl-level entrepreneurial skills to match. These 16 celebrities could actually afford to quit their day jobs, thanks to some very brilliant decisions they made in their utterly charmed lives.

Jessica Alba

Notable VentureThe Honest Company

Jessica Alba, the actress appearing nightly in your REM Cycle, created a company worth ONE BILLION DOLLARS. Yes, one billion actual dollars. She developed The Honest Company after the birth of her daughter Honor (…yikes), who sometimes broke out in welts due to the prevalence of synthetic chemicals, fragrances, and materials in so many child and infant products. She co-founded the company with the backing of three fellow entrepreneurs, and the business has skyrocketed in value since 2011. A laudable thing all around, especially since the only good movie she has literally ever been in is Sin City.

50 Cent

Notable Ventures: Vitamin WaterTMT (The Money Team) Promotions, SMS Audio, SK Energy, Real Estate, Finance, mining and heavy metal equity, G-Unit Films, G-Unit Clothing

Apparently, Curtis Jackson won’t stop till he collects as many business ventures as bullet wounds. With an ambition only rivaled in hip-hop by Sean Carter, Fiddy has spread his investing net wide—and with surprising accuracy. One of Mr. Cent’s first investments was also his most prudent, sinking a substantial amount of money into Glaceau (Vitamin Water, duh) right before they were bought out by Coca-Cola. Recently, he’s involved himself with mining and heavy metal equity overseas—to think, this is the same guy who wrote “Magic Stick.”

Paul Newman

Notable Venture: Newman’s Own

These days, Newman is just as well known for his cool ranch dressing as he is for Cool Hand Luke, which is kind of a shame, when you think about it. Nevertheless, Newman’s Own is the poster child for successful celebrity ventures, with humble beginnings as a boutique passion project for the legendary actor before going on to earn over $400 million over the past three decades. The best part? Newman (and after his passing, his family) gives 100% of the after-tax profits directly to various charities.

Will Ferrell

Notable Venture: Funny or Die

Ferrell, the clown prince of modern comedy, founded the notoriously no-holds-barred comedy website that has become known for skits like “The Landlady”  and “Between Two Ferns,” hosted by Zach Galifianakis, and featuring cameos from President Obama to Tila Tequila. You may scoff at Will’s frequently exposed hindquarters and sleazy, goofball characters, but no one will be laughing if he decides to sell the immensely popular site, which could be worth upwards of $300 million. They’ve done studies you know. 60% of the time, his business ventures work every time.

Hank Aaron

Notable Ventures: Hank Aaron Automotive Group, 755 Restaurant Corp

Hammerin’ Hank Aaron, the rightful Home Run King (not sorry Barry Bonds) parlayed his genial fame into a successful group of car dealerships and restaurants franchises, including Popeyes and Church’s Chicken. Aaron’s automotive group alone cleared upwards of $100 million a year before he sold most of his dealerships several years back.

Robert DeNiro

Notable Ventures: Tribeca Films, The Tribeca Film Festival, Nobu, Various restaurants and restaurant chains, real estate

DeNiro, the guy who repeatedly asked if you were talking to him (and possibly the greatest actor in the world), is the most prolific restauranteur on this list. Nobu, his upscale sushi chain, has locations spread all over the globe, from Hong Kong to South Africa, and is estimated to be worth upwards of $250 million. Factor in his involvement with Tribeca Films, the annual Tribeca Film Festival, and multiple other high-end restaurant entries, and his affluent teat has enough milk for a million Fockers, if you get what I’m saying.

Sammy Hagar

Notable Venture: Cabo Wabo Enterprises

Back when Van Halen was better than it is now, but still not half as good as it once was, Sammy Hagar donned the lycra pants that being an 80s rock frontman required….and did alright, I guess. But his real success has nothing to do with his music, and everything to do with Tequila. Hagar launched a super successful chain of Mexicana-fueled restaurants and nightclubs, with a distinctive homemade house tequila Hagar himself commissioned from a small, family-owned distillery. Hagar has sold off portions of his ownership in the Tequila brand over the past five years, netting a total of $91 million from the total sales.

Jessica Simpson

Notable Venture: The Jessica Simpson Collection

You may snicker, but Jessica Simpson—yes, that Jessica Simpson—has built her fashion brand into a veritable style conglomerate, with profits exceeding one BILLION dollars. Both her and Alba have companies in the billion club…makes you wonder what Jessica Biel is up to.

The Grateful Dead

Notable Venture: Music Licensing and Merchandising

You can argue that any number of “classic rock” bands could appear on this list for their merchandising prowess (The Rolling Stones, Kiss, and Bob Marley come to mind), but Jerry and co. were among the first to grasp the concept of bands as brands. They took complete control of their public image by allowing—and encouraging—fans to bootleg their concerts (tapes they would later release as best-selling live albums) and by taking charge of their music and imaging rights, something many bands lacked the foresight and means to do. Their legacy as music and cultural icons of the 60s and beyond has only been solidified with time, thanks in large part to their well-informed, ahead-of-the-curve business decisions.



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