Gary Vee Interview artwork

Gary Vee Interview

The Carton Show with Craig Carton & Chris McMonigle

July 17, 2026

Entrepreneur Gary Vee joins Craig and Cmac live from Fanatics Fest to talk sports, his career path, and much more.
Speakers: Craig Carton, Gary Vaynerchuk, Chris McMonigle
**Craig Carton** (0:00)
20 years ago, I met this young, impressive entrepreneur who at the time was just selling bottles of wine out of the trunk of his car, pretty much, going store to store, door to door, right?
And he's like, I got big plans, Craigie. And I go, let's see how those plans work out. 20 years later, you're doing pretty good for yourself. Gary Vee, everybody.

**Gary Vaynerchuk** (0:19)
Thank you, thank you.

**Craig Carton** (0:19)
For a long time, pal, how are you?

**Gary Vaynerchuk** (0:21)
It's great to see you, my friend.

**Craig Carton** (0:22)
Good to see you too. Good to see you, thank you. That's Chris McMonigle right over there.
Does a day go by, because I know people come up to me, they're like, yo, I know your friends are Gary Vee, tell him to buy the Jets. I go, he ain't got that kind of money.

**Gary Vaynerchuk** (0:36)
Not yet. And all this private equity money coming in is making it even harder. So, I should probably leave this interview and get back to work if I'm going to pull that dream off.

**Craig Carton** (0:44)
Even now you're working.

**Chris McMonigle** (0:45)
There's a garage sale somewhere.

**Craig Carton** (0:46)
There's always a garage sale. That's the other thing. Can you tell Gary, I went to a garage sale, I'm not rich.

**Chris McMonigle** (0:54)
I tried to turn that couch into a Cadillac, but I couldn't do it.

**Craig Carton** (0:57)
Lack of effort.

**Gary Vaynerchuk** (0:58)
Lack of effort.

**Chris McMonigle** (1:00)
You're not wrong.

**Craig Carton** (1:02)
Things are going good for you. What's the latest? What do you got going on?

**Gary Vaynerchuk** (1:05)
The Knicks won a championship. Of course everything is going good for me.

**Craig Carton** (1:08)
Stop there. Like you, die hard Jet fan, die hard Knick fan. The Knicks are my favorite team of all my teams. I think the Jets are yours.

**Gary Vaynerchuk** (1:15)
Yes, I'm Jets, Knicks. My son is Knicks, Jets, which I have a problem with, but I'll deal with that later.

**Craig Carton** (1:20)
See, but your son didn't live 50 years of his life without a championship. He has no concept of my life.

**Gary Vaynerchuk** (1:25)
Correct.

**Craig Carton** (1:26)
All right, now the Jet Party does. Yes. And he's going to get there.
Yeah, everyone knows I'm the Knicks fan, right? And the interesting thing about that is when part of your identity is rooting for a team that has never won in most people's lifetime, now that you've won, now what?

**Gary Vaynerchuk** (1:44)
Well, we're of the age where we would live this. Back in the day, you could really respect a Red Sox and a Cubs fan.

**Craig Carton** (1:51)
Yes.

**Gary Vaynerchuk** (1:51)
Like, the Red Sox especially, even though we hated them being here, you kind of respected that 100 year thing. Now, all Boston fans are straight nephos, we don't respect them at all, right? And now, us Nick fans, with the Rangers, that 1940 chant, that had a lot of weight, 1940
I personally never felt the weight of how long we hadn't won. It's just, I just wanted to win.

**Craig Carton** (2:21)
Right.

**Gary Vaynerchuk** (2:21)
So I don't know if a Nick fan identity was wrapped up in 50 plus years, it was just that we needed that.

**Craig Carton** (2:26)
Not the same way because there were no chants. Correct. No one ever said 1973, it's hard to have a chant anyway.

**Gary Vaynerchuk** (2:32)
Correct.

**Craig Carton** (2:32)
And we've been to a couple of finals, obviously, 94, 99
So there's like a little taste here, a little taste there. Yeah, but I think you're a little bit younger than me, but people don't understand the Rory Sparrow, Trent Tucker, Truck Robinson days, because it's a history book.

**Gary Vaynerchuk** (2:49)
Yeah, and Sky Walker, and everybody, listen, and we actually, at least, back to our ages, we had a little bit when Mark Jackson came along, we were making a little noise, young Ewing, then we had the really good years. You know, my brother, for example, he's 11 years younger than me, it's pretty much always been bad for him, right? Sure. The last 25, 30 years for the Knicks have been brutal. Even though my son's a little guy, he'll talk about that 2017 team and watching every game of a team that won 17 games. So, you know, fandom comes in different shapes and forms. There's a lot of people running around here at Fanatics Fest with Knicks gear on that are straight bandwagon.
Straight bandwagon. It's like Cowboy fans. They jumped on like five minutes ago. We've seen the videos on social. What college did Jalen, how big of a Knicks fan are you?

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