On the latest episode of her podcast, Danielle Snyder talks with investor, entrepreneur, author, podcast host and television personality Gary Vaynerchuk. In a wide-ranging discussion, she gets his take on social media, building community and the biggest vulnerability in young people today. Here, we share eight of the most interesting takeaways.


Gary Vaynerchuk and Danielle Snyder at the Pencils of Promise gala in December 2017


He was a "terrible" student. 


"My dad bought a liquor store in Springfield, New Jersey, I got dragged into that business. Fell in love with wine, collected as a 16-year-old… I got Ds and Fs in all my courses, but knew everything about everything you needed to know about wine and baseball cards.


"[I] was clearly somebody who was willing to play outside the vortex and the framework and lean into his passions. It served me well my whole life. I launched one of the first e-commerce wine businesses in America in 1996 called WineLibrary.com. [I turned my dad's] liquor store into an internet national player. Changed the course of my family's life and mine. We made it, grew the business from a $3 million to $60 million business."


He thinks working with family is the best.


“It's fucking hard but it's the best. And I think that if you over-communicate, it's the greatest thing of all time. And if you're willing to choose the love of the person over money, you will always win. And that's why I've been super-successful.”


He believes young people today are too impatient.


"The biggest vulnerability to all the youth — which I'm obsessed with, I hate that people shit on young people, I'm obsessed — is the lack of patience. This thought that you printed 50 t-shirts and a week later you're gonna be Supreme with your business? Or that you've taken two cute photos and you're gonna be a supermodel? The complete entitlement and lack of patience that parents have created for the 18-to-25-year-olds in our society is an enormous vulnerability.


"I [meet] kids [who] literally shit on their parents... and I come to find out that their parents bought their apartment and pay for their Uber, and I'm like, 'What are you talking about?' You're mad at your parents for not writing a million-dollar check for your ridiculously shit business idea, yet they pay for your Equinox membership? You're a fucking piece of shit."


Gary and Danielle recording the #NoFilter podcast at his studio in New York. 


He believes good parenting is like good management.


"When my daughter said that her idol is herself the other day it was the best day of my life. This is a self-esteem game. This is a lack of entitlement, self-esteem. Parents use children as collateral for their own self esteem or lack thereof. Good parenting is like good management. You need to put your players in a position to succeed, not based on what you want, but based on who they are.


“People ask me all the time, they think I want my kids to be entrepreneurs. I couldn't give a fuck. I want my kids to be as passionate about whatever the fuck they do in the way that I am. And if that is to make paintings out of tomatoes, then I'm like let's go. The end. I mean it. I'm super duper all in in putting them in a position to succeed. The end. And I just wish parents did more of that."


He passed on the chance to invest in Uber and Netflix.


"When people ask me about my mistakes, I've got some classics. Passing on Uber twice... I [almost] bought a million dollars worth of Netflix, three holidays ago. I was like, 'This is about to really get crazy,' but the phone call with my broker got disconnected because I was in Mexico, on my vacation... I was like, "I'm on vacation, I'll do it when I get back,' and I never did it. It was a really bad idea. It's exploded since then. I've got a lot of these good black-and-white you made a business mistake, but no question, the biggest mistakes I've made are the ones I didn't do."


He thinks brands are too dependent on Instagram.


"Watching everybody put their entire life into Instagram is the most interesting thing I'm watching. People are becoming so disproportionately reliant on Instagram socially and business-wise that when, not if, Instagram starts losing its attention graph, that's gonna be a big fucking problem for a lot of people... Fashion brands that used to rely on Vogue and Bergdorf [Goodman], who are now gonna be 100 percent fucking Instagram, are gonna be really sad in seven years, and that's what I'm watching.


"Diversity matters, and everyone's getting pot-committed, they're not posting anywhere else, they're not doing anything else, all they care is about is how many 'likes' they got on an Instagram post, how their Instagram — here's my favorite — people care about how their Instagram layout looks when you land on it so that it's aesthetically aligned.


"As a brand, somebody who produces content, across the board, [I'm] massively diversified: website, email, text messaging platform, podcasts, YouTube, Facebook, Instagram… I mean we're 25 [percent] here, 10 here, 15 here, seven here… diversity is, like… I'm not going to be vulnerable to anybody."


He turned down Shark Tank.


"I strategically didn't do Shark Tank a couple years ago. I didn’t want to be a one-off… Doing Shark Tank three seasons ago when they really wanted me would've happened before this last 18-20 months where a lot has happened with my brand. I was still on the come-up, it would have been an absolute big spike, I just didn't… It's interesting how things are playing out, I was like, I wanted to be the premiere thing, not a one-off. I just didn't want to.


"In the back of my mind I was like, I would do one episode, I would steal the fucking show, everybody would realize I'm a disproportionate talent — I mean that — I was literally, like, I'll win and become the thing... I love destroying faces when bullshit comes to me. I would be a great Shark."


He believes we need to be more aware of our digital legacy.


"In 400 years there'll be so much more content [about] you than even your parents or grandparents. I generally believe the majority of people right now that are living are setting the framework for their family's name. All the people that are spewing hate — I can't wait for the 23-year-old that today spews hate on social to have that conversation with his granddaughter in 41 years."


 This interview has been edited and condensed for clarity.

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Continue the party with late-night drinks at Parker & Lenox, a speakeasy that regularly flies musicians in from New York or Buenos Aires to perform at weekends, and for salsa dancing, Club San Luis in Roma Sur is an experience in itself. It has a 20-piece live band, and the dancing is phenomenal.

~ Danielle