Twenty years ago, E-40 named his album, Charlie Hustle: The Blueprint Of A Self-Made Millionaire. While the moniker and subtitle may have been accurate at the time, the founder of Sick Wid It Records has seemingly lived up to that statement ever since.

As 40 Water’s career has been going strong for nearly 30 years, the Vallejo, California native has become a beacon for investing as a key figure within Rap landscape. Like Too Short, JT The Bigga Figga, and others early on, 40 showed artists far beyond the Bay the values in independent music hustling. The Click member later held several franchises of Fat Burger, which he mentioned in interviews and on wax. His expansive portfolio now includes a Wing Stop, being a spokesperson for Landy Cognac, and starting his own brand of energy drink called “40 Water.”

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E-40 thrives in wine and spirits now, most notably in the form of his Earl Stevens wine label. However, one of Rap’s vino devotees for decades also makes sure that his product is quality. 40 heads should know the rapper’s been passionate about wine since his earliest days of rapping, name dropping Carlo Rossi with his crew, The Click, on the song “Let’s Get Drunk,” and then later dedicating an entire Federal track to the drink alongside B-Legit.

In a recent interview with Adelle Platon for Tidal’s Side Hustle, E-40 explains his interest in wine, and how he chose to pursue a business venture within the industry. “When I was a young mustache, you know, I’d sneak in my mama’s Carlo Rossi,” he says. “I started liking wine like that. That’s all I talk about – getting drunk off of wine in my lyrics. I always paid attention to how to do things; I was always an observer. I felt like, if there’s a Robert Mondavi, a Kendall-Jackson, a Rodney Strong, why couldn’t there be an Earl Stevens wine?” Instead of running from his name, which Rap fans knew, E-40 proudly stamped it right on his product labels.

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“I treated this adult beverage business like I did my Rap career – I came in independent; I did everything myself. I started off selling wine online, and then demand became so big, it came to the point where I needed a distributor,” he recalls on site at his warehouse. “So the distributor that I met when I was with Landy Cognac – I stayed cool with them. They ordered like 10 cases. Next thing you know, one store posted it up on their social media and the word got out. Everybody – I’m talking about everybody, all the stores started asking for it.”

Earl Stevens’ wine became a huge hit with retailers across the nation, and as E-40 points out, “[there] wasn’t no rappers doin’ wine.” 40 was truly one of the firsts, if not, the first. Furthermore, he points out an important factor some contemporaries and potential entrepreneurs might be slacking on: securing licenses. 40 ensured he had a license to distribute and sell his wine before embarking on developing other alcoholic beverages, such as his tequila, E. Cuarenta, and his mixed cocktail drink, Sluricane, which also draws from vintage Vallejo lyrics.

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Platon also asked 40 how he enters business meetings for potential investments, to which he explains that code-switching is not the way. “The best thing to always do for that: don’t be phony,” he offers. “I’m not gonna switch my voice up because I’m on a professional platform or something, I’ma be me.” In the conversation, E-40 also reveals that he and Chamillionaire are in a syndicate together for start-up companies. “[Chamillionaire] is a seasoned vet in it. He’s hit a few times. We were [involved] with The Ring deal, but we got in like three months before Ring sold to Amazon; they sold for $1 billion. But you know, we made some cool paper off of it real quick. [It was] three months. But if we was there from the beginning, it would’ve been beautiful.” Nas was an early investor, which helped land him on a recent Forbes list, for the first time in his career. One 2018 report estimated that Nas could have made as much as $40 million from the acquisition.

40 also discusses his venture in California’s legal cannabis business. The veteran may offer some more hustle advice in the form of two albums, The Rule of Thumb and Practice Makes Paper, later this year. Last year, he dropped The Gift Of Gab as well as B-Legit collaborative LP, Connected and Respected. This week, Earl and Chamillionaire both appeared in Trae Tha Truth’s “I’m On 3” video.

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#BonusBeat: Learn about Young Jeezy’s steakhouse business in Side Hustle: