Gary Vaynerchuk Is a Rapper’s Best Friend

ATLANTA — On a recent weekday afternoon, the fast-talking entrepreneur and advertising executive Gary Vaynerchuk, better known as Gary Vee, jumped out of an Escalade and marched into a recording studio an hour later than he was supposed to, trailed by a videographer as if he was the talent.

Inside, the up-and-coming local rapper Lil Keed, a protégé of Young Thug with a movie-star smile and winning demeanor, was patiently standing by, having decided to record a song while he waited for a sit-down with a man twice his age, who had nothing to offer at the moment but advice and conversation.

Why one of the hottest young artists in the city had found himself at the scheduling whims of a former New Jersey wine salesman-turned-social-media guru might be hard to fathom from the outside. And yet it spoke clearly to Vaynerchuk’s rising stock in the universe of hip-hop, where he has become an influential cheerleader, mentor and middleman, placing early bets on rising acts — as he did as an investor in Facebook, Uber and Venmo — and helping introduce them to his Fortune 500 client roster.

“Bro, you need to get very serious about TikTok,” Vaynerchuk, 44, told Keed, 21, after a few minutes of small-talk, as silence fell over the crowded control room. “You can get five times bigger,” he promised, explaining if one line goes viral, “your career is completely in a different place — you get one of those, you’re selling out Madison Square Garden.”

Keed, knee to knee with the businessman, listened intently, nodding along and promising to try out the social video platform as he approached the release of his new album, “Trapped on Cleveland 3.” “Forget trying,” Vaynerchuk insisted with harsher language. “Figure it the [expletive] out.” Keed’s managers exchanged giddy glances that confirmed they were taking mental notes while Vaynerchuk gathered TED Talk-level momentum and doubled down.

“I’d rather you have a minor hit in TikTok virality than be on Jimmy Fallon,” he said.

The rapper, appropriately galvanized, seemed poised for battle. “I’mma do this,” he said. “And I’ll be like, he told me, he told me.”

Moments of connection like this have become increasingly common for Vaynerchuk, who has built his penchant for micro-networking and a childhood love of hip-hop into a win-win scenario for himself and a ballooning number of rappers, who have come to view him like an earlier generation did Warren Buffett or even Donald J. Trump.

His rapper sit-downs, like most of Vaynerchuk’s day, are filmed and turned into content for his various millions-strong social channels (YouTube, Instagram, TikTok, Twitter, a podcast and more), lending him the youthful and diverse credibility that comes with a proximity to rap. At the same time, artists, from the unsigned to burgeoning superstars, get not only exposure, but branding and business tips, plus a potential entree to corporate boardrooms, where lucrative brand deals may await.

“Culture vultures are the worst,” Vaynerchuk said in an interview earlier this year, insisting that he had come to the rap world honestly. “I’m petrified of that perception because it couldn’t be further from the truth. I’m not some guy that sees hip-hop as culturally relevant, with business to be done.” He’s just a fan and a true believer, he said.

“When I’m playing at my level, I could be spending time with 100 icons that are in the illuminati that run” things, Vaynerchuk continued. “I don’t need Tee Grizzley,” he said, referring to the hard-edged Detroit rapper. “I’ll go hang out with Obama — I’m being serious! But that’s not fun for me. I’m not a fan of politicians. Straight up.”

As an internet personality, the Gary Vee character can be as patently absurd as he is engaging and convincing. His posts, which are often overlayed with aphoristic text like digital bumper stickers — “THE ULTIMATE ADVICE FOR EVERY 20 YEAR OLD,” “RECOGNIZE WHAT YOU’RE AFRAID OF,” “how to make money FROM YOUR BED” — can feel like hokey, get-rich-quick sloganeering. He is constantly plugging instructions like “How to Make 64 Pieces of Content in a Day.” And his manic energy befits a squirrelly sidewalk magician who seems like he might actually lift your watch.

Yet Vaynerchuk is a master of fostering intimacy — he really listens and retains personal details — and his track record in tech lends him authority. His A.D.H.D. aesthetic is perfectly suited for the sound-bite culture of the endless scroll. And he has a compelling personal pitch as an immigrant from Belarus, then part of the Soviet Union, who turned his father’s New Jersey liquor store into an early e-commerce success story and broke through online with snappy wine-review vlogs. In 2009, he founded the ad agency VaynerMedia, whose clients include GE, Anheuser-Busch InBev, Kraft Heinz and PepsiCo.

But it was Vaynerchuk’s relationship with Mike Boyd, 33, a college friend of his younger brother and business partner, A.J., that brought him seriously into the hip-hop fold. Boyd, who runs artist relations and music strategy for Vayner (and also manages Richie Souf, a go-to Atlanta producer for Future), represents the unassuming ears behind the boisterous executive. Boyd sets up meetings with his plentiful industry contacts and helms a weekly, increasingly influential Spotify playlist, “Monday to Monday,” that focuses on emerging artists.

“Mike lives and breathes new music,” Vaynerchuk said. “His ear is ingrained in the pavement — forget being close to it.”

Together, the pair have dabbled in playing matchmaker between their clients and rapper friends, helping to broker an early partnership between Jeezy and Avión tequila. (This year Jeezy sampled a Vaynerchuk rant on “the enTRAPreneur,” the intro to his new album.) In 2013, Vayner paid Migos to put a bottle of the liquor in the video for “Versace,” while the cult-favorite Atlanta strip club bards Travis Porter briefly flaunted Brisk iced tea. In an even less unlikely union this year, Yung Baby Tate, an underground singer and rapper, tried her hand at a song about Miracle Whip.

This is only the beginning, according to Vaynerchuk, who hosted a Budweiser-sponsored Super Bowl party this year featuring entertainment from Grizzley, Keed and YG. (Lil Keed, Vaynerchuk said, almost made an appearance in a Mr. Peanut Super Bowl commercial that featured Alex Rodriguez, but it wasn’t to be.)

“This is all about 2020,” Vaynerchuk said. “Next year, I want to put $10 million into their pockets.”

Yet for all the self-promotion and synergy, he claims that business is not necessarily the point — at least for him: “When I have the next Facebook or Uber, I pick up the phone and call these guys and girls, telling them to write a $50,000 check and they go make $4 million,” he fantasized. “Then three years later, there’s some line: ‘Gary Vee DMed me/turned it into $7 million,’ I just get to smile while my daughter runs into my room and says, ‘oh my god, DaBaby said this!’”

“I want my grandchildren to come to my funeral and 81-year-old DaBaby shows up!” he added.

The admiration, it turns out, is mutual. “Every rapper knows who Gary is,” said Lil Keed, who has referenced the entrepreneur in song. “He’s just genuine and has a great vibe. And he gives you the game — for free.”

ASAP Ferg added in a message that he and Vaynerchuk “are cut from the same elegant fabric. He’s a real underdog who wins and preaches the believe-in-yourself, do-it-yourself mentality that drives me,” adding, “He released a shoe! Who else in his space is being that creative?”

None of which is to say that there aren’t cringey moments of culture clash. At the studio in Atlanta, a Vaynerchuk bit on Joe Rogan and paywalled podcasting fell flat, while his pronouncements of “That was fresh!” after listening to a new Lil Keed song may have dated him.

And yet the rapport he’s developed across the industry is not merely a pose. At his office in Manhattan’s Hudson Yards, Vaynerchuk scrolled through his Instagram DMs, displaying extremely personal messages of angst and pleas for advice from A-list rappers, many of whom he’s never even met.

“I don’t want to be anybody’s Tony Robbins,” he said (though he added, “Tony is a friend”). “I’m so much more. I don’t charge any money from anyone — that’s not my business.”

“But what I love about gangsters, the Soviet Union and the streets of hip-hop,” he said, “is that it’s almost like the most merit-based game. If you’re doing the right thing, it will take care of you.”

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