Gary Vaynerchuk Drops Entrepreneurial Pearls On His 4Ds Mastermind

If you’re an entrepreneur or a professional in the digital marketing space, you need to watch this video. Seriously, this is a legit session. Gary Vaynerchuk so damn good.

I go on jags where I’m totally on the Gary Vee train. Everything he says is gold. Hustle. Hustle. Hustle.

But, then there are times, where I feel like he’s that judgmental father figure scolding me for not working my face off 19 hours a day building my brand.

Sometimes that grind Grind GRIND mentality is too much for me. I’m not THAT driven. Give me a business that pays the bills, puts money away, and lets me eat whatever I want from the menu and I’m happy.

Anyway, I haven’t been in a Gary Vee frame of mind recently, but then I stumbled upon this video, posted on November 6, 2018, and now I’m fired up.

So. Damn. Good.

Title is a little misleading, but we can forgive a little click baiting. He does talk about selling Facebook and Instagram, so it’s not egregious.

My Favorite Takeaways

I’m still not buying into “eat shit for 6 years to build a legit business.” Or the “be a personal, on-call sommelier for all subscribers to the new wine business.” Or “only sleep 4 hours a day, and get some kind of productive shit done in your sleep.”

Here are my favorite nuggets from this session …

Advertising on Social Channels is Tremendous Deal Right Now

Back in the day, radio advertising was a good deal. Then TV. The good deal right now is the seven platforms–Instagram, Twitter, Facebook, Snapchat, Youtube … not sure what else–that live on your smartphone). 

But, you have to become a media company and not just the advertiser. This is the main theme throughout.

Make as much content as possible.

“People take pride in organic reach because there’s something special about getting good organic reach in social, when the ads are underpriced.”

Instagram Account Is Public Relations

Get a good base of content on your Instagram account. Why? Because people search Google for your Instagram to figure out what you’re all about.

On Instagram spend 20% of your budget on branding and PR content. And 80% on ads.

Sotheby’s and Christie’s sell million dollar items on Instagram.

Volume Content Method

Easier to close a $60,000 client if you run 497 pieces of content and run micro media. To hit a $60K do a one minute rant specifically to 15 people that are likely to buy it, and overpay for 5,000 people to see it that don’t have any interest.

Example of highly specific target: upper Eastside, African American man that works in tech.

Talk very specifically to these people.

Don’t layer in high end brands with your targeting though, because many of those followers are aspirational and aren’t ready to buy. They are “not in consideration set.”

To hit people that actually purchase high dollar items, buy first party data of purchase intent. Or use  lookalike audiences on data you already own.

>> NOTE: I can vouch that lookalike audiences on Facebook work very well. It’s blows my mind too. So, I have a list of leads for a very specific type of training my day job sells. They’re in multiple markets. Facebook has access to so many data points that they can find more leads. They know who to put my offer in front of. It’s so weird. Think about it … 

Hey Facebook, here’s the email address of someone that filled out a form for a free eBook. Put my ad in front of more people just like this one that will have a propensity to fill out a form for this type of information. I’m overthinking this. But, damn, I can’t think about it too hard or everything in my immediate vision turns to fractals and I start drooling and humming a nervous tune. <<

Pump Out a Lot of Good  Content (Has This Been Mentioned Yet?)

Get nerdy about what you do. Very important. Demonstrate your expertise with content.

“A lot of people that try to replicate my model aren’t able to get away from the business goal. If you’re doing content you need to act as if you’re Architectural Digest, not Pablo Picasso, and people struggle with that. It’s the intent behind the content.”

Are you trying to be a B2B magazine or are you still subtly pitching the sale wrapped up in content?

>> NOTE: God it takes a lot of faith in that model. Spending the money/time to produce content with no embedded pitches. Takes a special boss/owner to agree to that. And a special operator to have the cajones to work it … daily … for years.<<

Gary mentions that they’re starting a wine project, and that he would rather act like Wine Spectator than QVC.

“It’s why Wine Library TV worked.”

He was the store owner, and thought he was going to do QVC with wine, but as soon as the camera turned on for his first shoot, he knew he couldn’t do it.

By episode 50, the process got so clean he “never had a wine on the show that I had more than 5 cases of.” Pure content.

He was so committed to impartial analysis on the show that he easily could have “panned” a wine even though his store just bought 200 cases.

On the flip side he didn’t want to expose himself to criticism for being a shill.

What if some kid on the wine team quits and tells everybody Vaynerchuk is using the show  just to sell wine. You lose all credibility as a media company.

>> NOTE: Don’t know if that’s totally true. There are precious few “pure” media companies out there. They’re all beholden to corporate sponsorship or agendas. But, good for GV for being a purist. <<

He goes on … As you get into content, the part that people struggle with is the intent.

“When I make content I am literally in Wikipedia/non-profit mode.”

Not afraid to sell when it’s time to sell, but content mode should be clean.

He suggests to an art and furniture dealer in the room:

“You reviewing another artists gallery and giving them love because you genuinely like their work is probably the most significant thing you can do for your business. That’s a brain fuck. But what you’re doing is becoming the artist whisperer to a community. Not selling your shit. Build trust.”

“That’s a brain fuck.”

Doing It All for the Insta

Same dealer suggests that nobody is going to want to go to a retail store in the future.

Vaynerchuk disagrees:

“Nobody is going to want to come there if there isn’t added value to go there versus what they think they can do online.

I think people want to do more shit than ever. Because they want to show people they’re doing shit.

People go to wineries and hike and yoga retreats. Why do you think all these weird museums are popping up? People want to take photos with the blue fuckin’ balls or sprinkles.

We are in full PR mode for ourselves and living our lives for the Instagram photo. People are literally planning their Saturdays predicated on the picture.

If I had a gallery I’d have one humongous thing that everybody wanted to take a picture of.”

“Pour All the Profits Back Into the Business, Kid”

A young entrepreneur asks Gary how to go to the next level (his company is currently pulling in $75K/month).  

Shocker. Gary tells him to move beyond the sales business of funnels and product launches (those are great and all) and move into content and building brand.

“Needs to be less about math and more about art.”

Gary says he sees it all the time. Kids pouring their big time profits into their lifestyle instead of back into business.

They’re having moments instead of building businesses.

Go All In With Stuff That Is Working Now

You never know when it’s going to dry up. Facebook Messenger is insanely good, so do it.

“Always squeeze the fuck out of an orange that’s full and then when it’s empty you go find a pear, which is harder to squeeze, then you hope a grapefruit comes along.”

“Email used to be 90% open rates for me. It’s not any more. Adwords was five cents a click. It’s not any more. People get so emotional about it going away that they don’t take advantage of it when it’s there.”

Crush MySpace when it’s MySpace then make sure you’re good on Twitter and Facebook when that’s happening.

Invest in your business on stuff that doesn’t bring you short term ROI (i.e. content and brand). That’s how you go from $2 million to $10 million.

Facebook can be better today than three years ago if you’re better at content and copy and matching it against your targeting.

Scale the Unscalable

“The whole game is scaling the unscalable. Everybody is looking, in this tech world, to find the scalable thing. The magic is in the unscalable part.”


  • Vaynerchuk gets a New York Jets beanie from adoring fan/paying mastermind customer.
  • He pulls off his own brand of K-Swiss sneaker a couple of times to prove points.
  • He’s eating something out of a plastic cup. I can figure out what it is. With brief glimpses it sort of looks like orange slices gummy candy. But, I think there was a crunch. What’s he eating? He makes it seem delicious.
  • There’s a boy in there (probably kid of attendee) cleaning his iPad incessantly for what seems like 30 minutes. It’s impressive.
  • Gary tells the purveyor of Mexican food, who’s considering franchising, to give franchises to his best employees. He tells him to hit up rich guys to invest in these loyal people that KNOW HOW TO MAKE THE TACOS.It’s kind of a brilliant idea right off the top of his head.

Gary vaynerchuk headshot5 gold stars

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