I got 30 minutes with Gary Vaynerchuck. Here’s what I learned.

I don’t do celebrity. My only role models growing up were my parents, because they were the ones fighting to put food on our table. To this day, ask me about any actor/model/scandal, and I’ll have nothing but a blank stare for you. I just don’t care.

That being said, I’ve always seen Gary Vaynerchuk as a no-nonsense marketer, and decision maker — someone I study from a tactical perspective. When I consume his content, I’m not looking for motivation or inspiration, I’m looking for tactics and approach. I never realized his celebrity factor until after I met him and saw the reaction from my network/the internet on a photo I posted.

When I say I’m not looking for motivation, I don’t say that to be cocky. I say that from the perspective of someone who toured the world as a hip-hop artist by the age of 22, was diagnosed with kidney failure at the age of 24, and beat all the odds to be make it out alive. At 27, I started a digital agency and hit six figures in billing in our first year. All that to say, I’m plenty motivated.

My opportunity to meet Gary came through my close friend and phenomenal artist, Anik Khan. I’ve known and worked with Anik for years now, and when Gary’s team reached out to him for a meeting, he knew it was something I would love to be a part of.

We pulled up to the VaynerMedia office on a rainy Monday in NYC, and waited a few minutes in their lobby before being walked over to Gary’s office. The office was humming with activity, and in typical form, Gary was wrapping up a meeting as we were walking in. His corner office was as humble as they come, and I took a seat next to the infamous wall of memorabilia and curios that I was used to seeing on episodes of the “#AskGaryVeeShow”.

The first thing I noticed was Gary’s presence. There wasn’t a whiff of entitlement or celebrity about him. He was genuine, curious and accommodating straight off the bat. It’s no question that his humility has contributed to his success and allowed him to build the platform that he has — no question is too small, and no individual is unqualified to ask what they need to. Having spent a lot of years in the music/entertainment industry, I can assure you that is not the norm: people who’ve accomplished a lot less than him routinely walk around with the craziest egos.

But enough with all this, let’s get to what I learned, right?

Legacy vs. Currency

We began the discussion talking about making decisions in the long versus short term. On the road to building an agency, I am faced with this type of decision making at every juncture. Should we take a well paying project to cover short term costs even though we know we might not enjoy the work? Or hold off for a dream client and forgo potential profits? Though it’s easy to take the high ground on this, the realities of running a business make it much harder in practice.

Gary was unequivocal about his stance here: Always prioritize your legacy over currency. “Every decision I make is predicated on my legacy. Money has never been a factor, even when I didn’t have it.” He stressed the importance of not giving up how you feel at your core about something for financial gains in the short term. It never ends up being worth it, and in Gary’s words, “Every time you do something for the money, you end up taking a few pebbles out of your ‘Legacy’ jar.” We discussed how sometimes this result is unavoidable, and Gary stressed that it’s ok, as long as you are self-aware about your actions and the outcome. Make business decisions that contribute to the way you want to be remembered, because the success you find through that work will always trump the satisfaction realized through the quick money grabs.

This is an issue that I will be unpacking for weeks to come, but as someone who has the tendency to prioritize short term financial wins, I needed to hear this. Message received.

Determine Your Production Capability + Create Strategy Around It

This is a powerful message for creators in every space. Artists, bloggers, producers, amongst others are notoriously poor at releasing content consistently, and will come up with every excuse under the sun for why they can’t do so. A lot of it comes from the insecurity of not trusting their own work, being judged by peers, or from trying to build “exclusivity” (which only works for a select few). But, for anyone looking to break through in today’s market, it’s essential to get over this hump.

Gary’s advice on this matter is to “create a song a day,” essentially challenging creators to produce the maximum amount of content possible, and letting the public choose which ones which are worthy of more attention. Not all creators can produce a piece of content a day, but figure out what your production capability is, and then engineer strategy around it to maximize attention and engagement. For example: If you’re a painter and you know you can produce 3 pieces of art per month, then build a social strategy which focuses on maximizing the impact of each piece instead of running around posting random unrelated things. Whether that’s recording a podcast around each one, doing a live Q&A, running a giveaway for your fans, or whatever — let your production define your strategy.

Centering your strategy around your production allows you to be intentional, targeted and thorough, while keeping your core audience engaged and new eyes coming your way.

You’re Either Giving or Taking

“When you’re taking, you’re giving up leverage, but when you’re giving, you’re gaining leverage. It’s your job to figure out the balance.”- Gary Vaynerchuk

In business, we live in the constant tug of war between giving and asking. Artists share a similar struggle. Will your fans be receptive when you ask them to buy tickets for your show? Will they share the branded content you did widely enough to convince the sponsors to invest you again? Will they buy the deluxe album package you’re offering even after you’ve given them two years of free music?

Gary explained that this struggle will always exist (and how he’s currently going through it while promoting Wine Library), and because of this, it’s your responsibility to consistently give way more than you ask for. Whatever medium it is through which people are consuming you, keep them fed at all times, and always keep your give-to-ask ratio absurdly high.

This is in line with his “Jab, jab, jab, right hook” philosophy, but my main takeaway here was — if Gary has the ability to produce a piece of content every day, I have no excuse not to be able to do my version of the same thing. And neither do you. Simple, but crucial.

So, there it is. My 30 minutes of face time with Gary Vaynerchuck, broken down to the key moments. Ultimately, his sincerity and willingness to help out young entrepreneurs speaks volumes about how he views his own legacy and purpose. I am grateful for his time and the opportunity, and am wholly convinced that our paths will cross again soon. I left the meeting inspired and laser focused on what I needed to take things to the next level for myself and the people around me.

So, I leave you all with the same piece of advice he left us: Go execute.

Like what you just read? Clap it up so this article can reach more people and impact them!

Have questions about entrepreneurship, investing, tech, music, or anything in between? Get in touch with me at @anihustles and tune into my weekly live Q&A session!



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store