The GaryVee Interview Everyone Needs To Hear
“What did I learn in the first couple years? That I was that guy,” Vaynerchuk told me.
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Hey friends,
I recently traveled to New York City for a conversation with Gary Vaynerchuk, also known as “GaryVee,” about ownership, obsession, AI, NIL, and what it takes to build ventures that last.
From transforming his dad’s company from $3 to $60 million and walking away with nothing, to firing his best friend to save his company, Vaynerchuk opened up about the moments that defined his business career.
He shared why he believes most coaches are losing locker rooms, how NIL money is exposing — not changing — young athletes, and why his advice to 17-year-olds getting paid is simple: tune your parents out.
This episode touched upon a multitude of topics, including Vaynerchuk’s mindset on momentum, the reality of working 100-hour weeks in his 20s, and why balance is relative.
Whether you’re building a $100M media company, trying to make it as a young athlete, or figuring out how to balance life and ambition, this episode delivers a masterclass in mindset, sacrifice, and execution.
Without further ado, let’s dive into my favorite takeaways:
1️⃣ Be Unstoppable
Vaynerchuk and his brother, AJ, began VaynerMedia in 2009 after he first transformed his family’s New Jersey liquor store into Wine Library — a first-of-its-kind e-commerce platform for alcohol.
By leveraging online marketing through the roots of social media, Vaynerchuk began Wine Library TV, a daily YouTube show featured on cable programs such as Ellen and Conan.
Given his first-hand experience, Vaynerchuk strove to help other companies maximize market share potential through social media, by reaching target consumers via Twitter, Facebook, Instagram, Snapchat, and TikTok.
Now, VaynerMedia operates underneath Vaynerchuk’s VaynerX umbrella, which was on track to surpass $300 million in annual revenue last year.
So, what did Vaynerchuk learn over the last 16 years while transforming the digital marketing space?
“That I was unstoppable,” he said. “I’m being dead serious. The first two years, I was barely involved in the business, and we did $1.7 million in revenue. And, the first year I ran it, we did $11 [million] and next year we did $27 [million]. Like, honestly, I know that’s a weird answer, and I kind of keep it humble, but I feel comfortable giving you the truth.”
A decade ago, VaynerMedia was first named as one of Ad Age’s A-List agencies, spearheaded by record-setting campaigns with Budweiser and Kraft-Heinz. By constantly staying ahead of the curve, Vaynerchuk has become a constant trend setter rather than a data point.
“What did I learn in the first couple years? That I was that guy,” Vaynerchuk told me. “… It was always going to work. I knew nothing about the advertising industry, [but] I knew everything about advertising…”
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2️⃣ Balance Is Relative
When people talk about “GaryVee,” he’s widely become portrayed as the poster child for “Hustle Culture,” or the constant, day-to-day grind to realize maximum potential — both in business and life.
I asked Vaynerchuk what he’s learned about balance and how it’s impacted him throughout his business journey.
His answer might surprise you.
“I’ve been balanced,” Vaynerchuk said. “I don’t know, I’ve slept seven, eight hours a night my whole career… I take seven weeks of vacation. I just go super hard when I’m awake.”
“And, by the way, who gets to decide balance?” he continued.
Vaynerchuk explained to me that balance is a relative term. If your occupation is the defining aspect of who you are, 80 to 100-hour work weeks could be viewed as “balanced.”
Contrarily, Vaynerchuk said he’s a big believer that people who work four to five days per week from 9 a.m. to 4 p.m. can still live a “balanced” life, depending on their grand aspirations and goals.
For him, however, he’s committed his life’s work to a multitude of brands that sit under his scope. The term “work-life balance” has almost become a misleading one to Vaynerchuk.
Instead, it’s just “life,” and the success earned from his enjoyable daily work provides him with balance.
“I know what the leisure life feels like, it’s good,” Vaynerchuk said. “I just like what I do too much.”
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3️⃣ Don’t Weaponize Earnings
During our conversation, I asked Vaynerchuk about college football’s current state and how he’d advise top-ranked high school prospects to best manage lofty NIL deals.
His answer? Pretend like your first paycheck could be your last.
“My big thing with these kids is, like, ‘Are you OK if this is your last bag?’” Vaynerchuk said. “Because, as you know, for a lot of them, it will be their last bag… So, you know, I would say to tune the noise out, including your parents, do the right things by the people who deserve it around you.”
Vaynerchuk would advise recruits to be thoughtful. While most younger players tend to give portions of their earnings to family and friends, it’s best to realize that money will never be a viable band-aid to heal relationships.
Instead, the nest egg should be treated as such, and it should be utilized as an initial tool toward achieving long-term financial literacy.
“This is a tough one for a 17, 18 year old kid,” Vaynerchuk said. “Don’t use money to fix fractured relationships… You can’t buy the friendships… Get into your therapy mindset. Get into your positive thinking.”
To watch the entirety of my conversation with “GaryVee,” click here.
If you have any questions, comments, or feedback, please don’t hesitate to reach out to me by email at adam@brenemanmedia.com.
You can also find me on Twitter, Instagram, TikTok, LinkedIn or Facebook.
Shoutout to Connor Krause for helping to write this newsletter and putting it together!
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