The evangelism of Gary Vee

When I arrived in downtown Tampa Tuesday evening, the line for the keynote event of Tampa Bay Start-up Week ran the length of two blocks, wrapping serpentine around the historic Tampa Theater. And – might I add – I was more than an hour early. Such is the mythology that surrounds Gary Vaynerchuk. As I stood in line, young entrepreneurs, wannabe entrepreneurs, and even established businesspeople chattered with excitement of “Gary.” His fans refer to him on a first-name basis, like an old friend they’ve come to lean on. 

I entered an already full Tampa Theater a few minutes later, where the buzz of the crowd was electrifying. A live DJ entertained a packed house with a mix of alt R&B and electronic house music, and I marveled at the diversity of the crowd. Sure, it was tilted toward millenials, but it was black, white, Hispanic, and Asian – dressed in a range of attire from business casual to crop tops and MC Hammer pants. “Gary Vee” – as he’s often referred to – casts a wide net; so I shouldn’t have been surprised that his walk-up song was Crossroads by Bone Thugs N Harmony.

Speaking of crossroads, so sits the state of entrepreneurship today. The electricity of the crowd was quickly grounded by a Gary Vee-style reality check. His choice descriptors for the state of entrepreneurship included: “amazing and awkward, fearful, Americana, and incredibly important.” My personal favorite – “weirdly dangerous.” In an age where corporate jobs have become the enemy of happiness and “entrepreneur” is a status symbol, Vaynerchuk was unafraid to lay out some harsh realities.

True to his brand, Gary Vee let wisdom and expletives fly, arguing that the current state of entrepreneurship is “so bright, it’s blinding people to their truths.” In other words, people are trying so hard to do what’s cool, they’re losing sight of themselves, their strengths and their motivations. The truth is, 90% of the people in that room believe they’ll make it as an entrepreneur, but only 1% will actually do it. And so, Gary instilled three main pieces of wisdom to the optimistic crowd: Self-awareness, patience, and scale.

Deploy self-awareness: AKA – is this really what you want to do? For most people, the answer is no. Much of Vaynerchuk’s talk focused on this singular subject, an indication of its importance to his ideology. According to Vaynerchuk, “When you own your own business, you’re in the business of eating sh*t.” He continued, “Do you like getting punched in the face? Do you have the stomach for it? It’s not cool. It just feels cool right now.” 

Practice patience: According to Vaynerchuk, the current state of entrepreneurship disrespects patience and underestimates the grind necessary for success. To build a real, successful business, patience is a must. To build his dad’s business, Vaynerchuk spent 16 hours a day, every day, answering questions about wine on Twitter. Just because it’s not working today doesn’t mean its not working. 

Scale isn’t failure: Every entrepreneur dreams of a business grossing hundreds of millions of dollars. But this is unrealistic, and might actually be detrimental to building a successful business. Vaynerchuk argues that we need to scale our thinking when it comes to dollars and cents. Success can mean a business that grosses 500k, so long as it’s making money and making you happy at the same time. 

With hard-hitting wisdom flying in every direction, Gary Vaynerchuk has established a brand following akin to religious fanaticism. I may even go as far as to call him an evangelist, as he’s fostered what Eric Adams of Entrepreneur Magazine characterizes as an “ever-growing group of fans who treat him as an all-knowing sensei, enamored with his ability to cut right to the heart of their problems.” Seeing Vaynerchuk speak with such authenticity made his brand fanaticism more relatable. He’s like a walking, talking, no BS self-help book. One that you really want to read. Eric Adams says it best when he says Gary Vaynerchuk is “half man, half brand, half digital experiment. And somehow, that all adds up.”