His message is what so many desperate people want to hear right now. It’s also dangerous.

Sarah Kessler

There are few business maneuvers that Gary Vaynerchuk appears to love more than the flip. The Belarus-born, New Jersey-raised, straight-talking entrepreneur — “GaryVee” to his fans — regularly recommends flipping everything from sports cards to sports cars. He once created a special five-part video series devoted to his love of yard sales, and in January, suggested his fans flip 250 sweatshirts printed with the slogan “Hustle like my name is GaryVee,” congratulating via tweet those who succeeded in driving the price up on Ebay. So when the coronavirus essential supply schemers emerged in mid-March, like a teenage boy in the U.K. who sold squirts of hand sanitizer to his classmates, it wasn’t so much of a leap to conclude that, as one tweet put it, “this kid is 100% a GaryVee fan.”

Though there is no way to count exactly how many people publicly assumed that Vaynerchuk would support flipping essential supplies during a pandemic, there were enough that Vaynerchuk decided he needed to address them through his social channels. “There have been so many articles written about people hoarding hand sanitizer and wipes and things of that nature and flipping it, and I see a lot of people tagging me,” he said in a video posted on March 14, emphasizing his disapproval. “When there is a global pandemic and people need things and you hoard them to flip them on eBay and Amazon… That’s garbage, that’s not fucking entrepreneurship I look up to. That’s fucking disgusting horseshit.”

Distributed to his 4.5 million Facebook followers, 8.3 million Instagram followers, and 2.1 million Twitter followers, the video resembles the thousands of others Vaynerchuk has posted over the past 14 years: a raw, barely edited aesthetic, with Vaynerchuk addressing the camera head-on in the tone of a football coach having a heart-to-heart pep talk with a struggling player. He’s 44 years old, with a raspy voice, and gray stubble — dad-age to many of his young fans (he’s said he has particular influence with young men ages 15 to 25, and has 4.6 million followers on the Gen Z-dominated platform TikTok) — but there’s something about his prolific F-bombs that make him seem like the cool grown-up. The one who is actually going to tell you how the world works instead of insisting that you do your homework.

For more than a decade, Vaynerchuk has been an evangelist for a branch of entrepreneurism known as “hustle culture,” a philosophy that looks a lot like meritocracy, but with punchier slogans. Stemming from the lore around Silicon Valley figures like Steve Jobs, Mark Zuckerberg, and Bill Gates, it’s the idea that anyone who applies enough talent, grit, and passion can start a multibillion-dollar business — or achieve whatever their dream is— if they hunker down in their proverbial garage and put in the work. Over time, as startup culture has bled into culture at large, this belief has metastasized into a way of life.

In recent years, a small economy has emerged around this lifestyle, complete with a Hustle & Grind swag shop, The Hustle media company, and a slew of startup hustle boot camps. It’s the philosophy baked into freelance website Fiverr’s exhaustion-glorifying ads (“You eat coffee for lunch. You follow through on your follow through. Sleep deprivation is your drug of choice.”) and WeWork’s infamous “Thank god it’s Monday” slogan — also the name of a mandatory weekly staff gathering that went on for hours after the actual Monday work day.

In a 2019 article about hustle culture, the New York Times called Vaynerchuk its “patron saint.” Vice, a year earlier, crowned him hustle culture’s “king.” And it’s easy to see how Vaynerchuk earned these titles: One of his most popular YouTube videos, which has been watched more than 1.2 million times since it was posted in 2014, is an explanation of why “hustle” is “the most important word ever.” People should “hustle their face off 15 hours a day,” he says, in order to get others to care about whatever it is they are trying to sell. “I just think people are loaded with excuses,” Vaynerchuk explains.

Vaynerchuk is his own most powerful example of this. He chronicles his original hustle in his 2009 book, Crush It!, explaining how he grew his family’s New Jersey wine store business from $4 million to $50 million in revenue per year, partly by developing a personal brand of “the wine guy that tells it like it is in plain English.” After his vlog, Wine Library TV, took off in 2006, Vaynerchuk writes that he woke up one morning thinking it was time to use his growing personal platform to talk about business, too.

He’s been hustling ever since: In 2009, he founded the ad agency VaynerMedia, and shortly after he started building a portfolio of communications businesses under a holding company called VaynerX, which he often refers to as “Vayner Empire.” It includes the women’s lifestyle blog PureWow, a speaking agency for which he is the star client, a marketing consultancy for small businesses, and an e-commerce consultancy that he launched in late April, in the middle of the pandemic.

While running his businesses, he has continuously doled out advice to other entrepreneurs in five bestselling books, frequent keynote speeches, and constant streams of social media content that explain how to replicate his success by summoning a combination of grit, self-awareness, and personal accountability. “You want to have business success?” he asked the crowd during a keynote speech in New Jersey last fall. “Watch what I do for the rest of my life publicly, copy it verbatim, but then put your shit in it, and I promise you, you’ll be successful. Because I’m fucking really good at my shit.” Or, as he put it even more directly in another clip, “Fuck your fucking excuses. I’m winning on this algorithm. You can, too.”

All of this has translated into a highly engaged fan base. Earlier this year Vaynerchuk sold tickets to a solo keynote he gave at a Texas stadium with a 12,000-person capacity for up to $500 a piece. He also sells $12,000 tickets to small day-long workshops at which he is guaranteed to appear for only one hour. After the pandemic hit, he quickly launched a new YouTube Q&A show, “Tea with GaryVee.” By the first episode, he already had tens of thousands of viewers. By episode eight he declared: “We are punching corona in the fucking throat.”

As the most outspoken voice of hustle culture, Vaynerchuk is also the most frequent target of its critics. Entrepreneur Alexis Ohanian famously called “hustle porn” the most dangerous thing in tech right now. “As entrepreneurs, we are all so busy ‘crushing it’ that physical health, let alone mental health, is an afterthought,” he wrote in a blog post in 2018. (Crushing It is the title of one of Vaynerchuk’s books, a sequel of sorts to Crush It!) This February, the Reddit co-founder publicly criticized Vaynerchuk for posting the message “eat shit for 48 months, eat caviar for the rest of your life,” tweeting “I can’t blame you for wanting to make a buck, but you know this isn’t true. And it’s unhealthy, literally and figuratively.” Basecamp co-founders Jason Fried and David Heinemeier Hansson wrote an entire book as a manifesto against what they see as a narrative in entrepreneurship that needs to be retired. “Long hours, excessive busyness, and lack of sleep have become a badge of honor for many people these days,” they write. “Sustained exhaustion is not a badge of honor, it’s a mark of stupidity.”

Now, as the unemployment rate hits historic highs, small business owners are fighting for survival, and Americans are settling into an uncertain, pandemic-driven recession, the call to hustle and grind our way through it seems even more seductive. Is that the mantra people should be following right now — or a toxic, illusory promise?

For someone who does not, as Vaynerchuk recently told the New York Times “want to be anyone’s Tony Robbins,” he does an awful lot of speaking with Tony Robbins. They’ve been billed together in Chicago, Nashville, Washington, D.C., Portland, and Salt Lake City. Still, the very suggestion that Vaynerchuk is a motivational speaker, he once told an interviewer, literally makes him throw up a little in his own mouth. Vaynerchuk has gone as far as to frame the founding of his advertising firm, VaynerMedia, as an attempt to avoid this very fate. “I think I even needed it for myself… to just scratch that itch that I wasn’t a charlatan or personality,” he told TechCrunch in 2017, “that I had chops, but just happened to be a little narcissistic or over the top.” (Vaynerchuk declined to talk to Marker for this story.)

Unlike many motivational speakers who proffer real estate investment schemes or advice about “thinking like a rich person,” Vaynerchuk has plenty of real-world entrepreneurial experience to draw from. VaynerMedia, his largest business, employs around 900 people and is most famous for its social media campaigns. (Remember earlier this year when Mr. Peanut was killed off at the Super Bowl, then resurrected as Baby Nut? That was VaynerMedia.) The agency has briefly included an events division called VaynerLive and a “product sampling division” called VaynerSampling.

Beyond the empire of VaynerX businesses, Vaynerchuk also has a diverse roster of ventures, from the ambitious to the oddball. He is a partner in a sports star talent agency and a cannabis-focused marketing firm, and was (briefly) the co-founder of an influencer agency specifically serving stars on the now-defunct app Vine. He owns a piece of Minnesota’s Call of Duty esports team, calls himself an early backer of Uber, Birchbox, Facebook, and Twitter, and co-founded an early-stage venture fund backed by the Miami Dolphins owner Stephen Ross (one of the fund’s early investments was in Medium). According to the New York Times, Vaynerchuk is also an advisor and middleman to hip-hop artists, including Lil Keed and Jeezy. He has trademarked his own signature, as well as the food brand “GaryVee’s Podcast Puffs,” which he prototyped and featured in a video about pairing wine with breakfast cereals. The latest version of GaryVee-branded shoes, marketed through a partnership with K-Swiss, remind wearers via a patch sewn on the insole that “you’re gonna die.” His ultimate goal, he says, is to acquire a legacy brand like Tootsie Rolls or Reebok, turn it into a $3 to $5 billion company, flip it, and use the windfall to achieve his life-long fantasy — buying the New York Jets. He may be getting a little closer; on July 1, his wine brand Empathy Wines announced it had been acquired by the beverage giant Constellation Brands for an undisclosed sum.

But no matter how much Vaynerchuk may remain involved in the day-to-day running of his businesses, or how many new business ideas he has, his accomplishments have been eclipsed by his own personal brand. Along with his always-on social media blitz, he regularly makes television appearances on CNN and Good Morning America. Social media content marketing, Vaynerchuk’s area of expertise, is a niche topic, but his most popular videos have much more universal appeal like “One Life, No Regrets” and “The Ultimate Advice for Every 20-Year-Old.” You can seek out his wisdom using the Gary Vaynerchuk search engine, which surfaces relevant snippets from his massive archive of keynote speeches, rants, and podcasts. Or attend an event with taglines such as “New Year, New You” or “Unlock Your Potential With Entrepreneur Royalty” on his nonstop speaking tour.

In November, back when people intentionally packed into large ballrooms, I shuffled into a powder pink resort in Orlando with nearly 3,000 aspiring entrepreneurs to attend one of these events. The “National Achievers Congress” promised, as Vaynerchuk put it in a marketing video posted on the event’s website, to provide the “tips, the tricks, and the execution to win today’s day.”