Side Hustles, CBD, and Soulja Boy: the Best Celebrity Business Ventures of 2018

December 11, 2018
Updated 2mo ago

By Max Godnick

There's nothing new about the celebrity side hustle. Just ask Jane Fonda circa 1986.

Even the rich and famous still need to make an extra buck. But 2018 will be remembered as the year Hollywood got rid of the "side" and simply hustled. Entertainers and athletes stepped out of their comfort zones, venturing into less familiar territory, and in some cases, made billions. From Kylie Jenner being questionably crowned a "self-made billionaire" to Rihanna forcing Victoria's Secret into an existential crisis ー the year that was saw a wave of celebrities expand their businesses in creative and unexpected ways.

Here are our favorites.

Lights, Camera, Basketball

"Space Jam" debuted in 1996, but 2018 was the year the NBA truly went Hollywood. Basketball's three biggest stars ー LeBron James, Kevin Durant, and Stephen Curry ー each dramatically expanded their entertainment empires, with a seemingly never-ending slew of new production and development deals.

The NBA intelligentsia had long speculated that James would sign with the Los Angeles Lakers in free agency, at least in part due to his ambitions in Hollywood. They were quickly proven right. James has projects on the air or in the works at Netflix ($NFLX), HBO, Bleacher Report, and NBC (to name a few) ー and of course the upcoming "Space Jam 2" ー with his SpringHill Entertainment production studio.

His two main on-court rivals, Curry and Durant, both of the Golden State Warriors, quickly followed suit. In July, Curry teamed up with Sony to produce faith-based family projects. And just last week, Apple ($APPL) added "Swagger," a show about Durant's experiences playing youth basketball, to its burgeoning original content slate. Game on.

Teigen Does Target

Chrissy Teigen is Hollywood's social-media darling, but 2018 saw the star parlay her massive digital following into real world ventures. The model and actress spent the year building a portfolio of down-to-earth lifestyle projects that inspired Slate to deem her the "anti-Gwyneth Paltrow". She launched a kitchenware collection with Target ($TRGT), partnered with Pampers, and even added six of her original recipes to Blue Apron's meal-kit menu. Along the way, she's authored two cookbooks, collaborated on a makeup line with Becca cosmetics, and even found time to give birth to her second child with husband John Legend this summer.

Soulja Boy Play 'Em

It's been 11 years since Atlanta-based rapper Soulja Boy (formerly Soulja Boy Tell 'Em) hit number one on the Billboard charts with "Crank That (Soulja Boy)" and its accompanying proto-viral dance. Now, he's self-branding more than songs and dances with the launch of his very own game console. The SouljaGame Console and SouljaGame Handheld went on sale this month ー raising more than a few eyebrows in claiming to run PlayStation, PC, SEGA, and Nintendo games in addition to up to 3,000 built-in titles. Despite some healthy skepticism from industry insiders, Boy claims to have made $250,000 in the consoles' first day on sale. Consider his swag turned on.

'Self-Made' Billionaire Kylie Jenner

Kylie Jenner is neither self-made nor a billionaire, but that didn't stop Forbes from declaring her to be a self-made billionaire on the cover of its "America's Women Billionaires" issue in July. The headline drew criticism both for its financial assessment (its subtitle lists her net worth as $900 million) and its "self-made" descriptor. (Jenner grew up as the youngest daughter of reality TV's royal family, much of her childhood playing out on-camera in her mother's Calabasas mansion.) But, controversy aside, there's no denying the 21-year-old's cosmetic company, social-media influencing, and endorsements have made her one of the faces of the new digital economy. Her portfolio has already eclipsed those of her older sisters (even Kim) and with over $630 million in sales, it may be hard for the rest of the Kardashians to keep up.

Kathy Ireland: CBD Mogul

Kathy Ireland was the face of health and relaxation on the covers and catwalks she graced throughout the 1980s and 90s. And that was before she started using CBD. This year, the model added the non-psychoactive cannabis byproduct to her Kathy Ireland Health & Wellness Line. In August, Ireland, now the Chief Brand Strategist of Level Brands, told Cheddar she was "very excited" about the space, comparing CBD usage to giving a child "a grape but not a glass of wine."

Rihanna Finds Gold in a Hopeless Place

Rihanna was one of the best-selling artists in music history long before she added an additional revenue stream in the form of a massive beauty empire. Fenty Beauty (named after the singer's surname) hit stores in September of last year and has not slowed down since. This year, Fast Company named it one of the World's Most Innovative Companies after its sales helped boost Sephora's cosmetics and perfume revenue by 17 percent in its third quarter. She also is behind a size-inclusive lingerie collaboration with Savage ー spearheading the intimates industry's push into diversity and inclusion and plunging Victoria's Secret into controversy as its halo looks more tarnished by the day.

Read all the 2018 Cheddar Awards here.