Gary pulled out his phone mid-conversation and showed me a number he'd never put on camera before. Not the agency revenue. Not the VeeFriends projection. The number he showed me was the one that still separates him from the thing he's wanted since 1986 — since a kid from Edison, New Jersey, in a knitted green jersey with "Gary" hand-stitched on the back by his mother, at 10:30 at night after she'd finished the cooking and the cleaning and the waiting for his dad to come home from the store.
He wants to buy the Jets. He has wanted to buy the Jets for forty years. He is one of the most recognizable brand builders alive, with a marketing agency that counts every Fortune 500 company as a potential client, and a collectibles universe he's pitching as the next Pokemon. And he's still not there. "I am not in the liquid position where I feel like, hey, let's call a meeting. I'm not interested in embarrassing myself."
That sentence is the episode.
Not the collectibles thesis, not the college debate, not the VaynerSports story — although all of that matters and we'll get to it. The episode is about the difference between having a dream and being in position to execute it. Those are two completely separate things, and most people treat them like the same thing.
The gap between the dream and the liquidity
Gary's been publicly saying he wants to own the Jets for fifteen years. He's said it at Jets games. He's said it in interviews. Jets fans know him as the guy who will one day buy the team, or die trying. That level of public commitment is rare — and also, he told me, a real cost. "One day, the Jets will transact in my lifetime, God willing. Unless I buy it, the world will collectively say that I failed."
He's put himself in a corner on purpose. I understand that move — I've made similar ones. When I was coming out of Nebraska, I told people publicly what I expected to be paid, what I expected to contribute, what I expected my career to look like. That kind of public declaration does something to you internally. It raises the cost of backing down. It makes the dream more real by making it more expensive to abandon.
But the thing Gary said that I keep turning over is what comes right after that admission: "I'm focused 100% on what I need to do about it." Not what the Jets need to do. Not when Woody Johnson decides to sell. What he needs to do. The dream is fixed. The preparation is the variable. And the preparation, at his level, is a specific kind of work — building the asset stack that creates the liquidity to make the call, so when the stars align on timing, he doesn't have to say he's not ready.
That framing applies to every ambitious person in the audience of this show. The Portland Trail Blazers situation came up because I'm in a similar spot — the stars aligned on an opportunity and the question was whether the liquidity was there to match the timing. Gary's answer was direct: "Putting yourself in a position to borrow money." Not wait. Not save. Understand the financial architecture of how big acquisitions actually get done, then build the relationship capital with the institutions that make them possible. Ryan Smith and Matt Ishbia didn't write a check for the Jazz and the Suns out of a bank account. They built the position to leverage.
Most people with a big dream spend all their energy on the dream. Gary's been spending his energy on the position.
Why he sat on sports cards for a year — and what that actually cost him
The collectibles conversation started because Gary called it first. In 2017, before the pandemic boom turned sports cards into a fever economy, he saw what was coming and then deliberately didn't talk about it.
"I knew sports cards were happening in '17, and I sat for a year." He was scared he was forcing the belief because he loved the category — that nostalgia was clouding the pattern recognition. So he watched. He let a year pass before he started telling people.
I know that cost. I sat in cash from 2010 to 2012 for similar reasons — I didn't understand the market well enough to trust my own read on it, and I didn't have the right team around me yet to translate what I was seeing. The opportunity cost on that was probably eight figures. Gary's version of sitting on his hands cost him something different: positioning. The people who started talking about trading cards in 2017 built audiences around that call. They own the intellectual territory. He waited a year and came in behind his own instinct.
The lesson he's drawing from it isn't regret. It's methodology. He's now building an entire business — VeeFriends — around the insight that collectibles are becoming a lifestyle asset class the way sneakers and fashion became one. His thesis is that the mechanism driving it is human and ancient: people have always collected, but social media changed what collection communicates. It made the flex visible at scale.
PULL QUOTE: "I would rather buy a 1957 Bill Russell rookie card for $25,000 and have it be $49,000 in six years liquid — than buy $25,000 worth of Tesla stock and have that be $49,000 worth of liquid." — Gary Vaynerchuk
The financial return is the same. The lived experience is incomparable. You can photograph the card. Your friends know what it means. The community around the card is something you belong to, not just something you've purchased exposure to. Gary's argument is that for a meaningful percentage of people — he put it at six or seven out of ten — that experience premium is worth the same return as a pure financial instrument. And once you accept that, the category isn't a hobby. It's an asset class with an emotional yield that no stock can replicate.
The agency deal we almost did — and what it actually revealed
VaynerSports came up because we almost worked together. Gary bought into a small sports agency after a random Twitter moment involving a practice squad punt returner's jersey, AJ needed a project after a health scare, and the thing became real faster than either of them expected. By the time we were talking, I was a name that made sense for what they were building.
We couldn't get to the economics.
Gary remembered it clearly and he remembered it right: "You rightfully were like, 'If I come, this is very valuable. I want to own a piece of the agency, not just have a good commission from you.'" And VaynerSports, at the time, couldn't give me what I thought the value of the association was worth to them. They thought my valuation of my own contribution exceeded what they believed they could deliver over time with or without me.
Both of us were correct. That's the part nobody talks about when deals fall apart — sometimes it's not that someone made a mistake. It's that two honest assessments of value didn't match, and neither one was wrong. I knew what a player at my level brought to a young agency's credibility. They knew what their growth trajectory looked like. The gap wasn't negotiating incompetence. It was a genuine difference in projections.
The reason I'm telling this story now is what came after: "Hell yeah," when I asked if there was an opportunity to circle back. VaynerSports has the Sauce Gardner deal done. Aidan Hutchinson's contract is coming. Kirk Cousins became the poster child of a VaynerSports-represented player maximizing his moment. The agency I passed on — because the math didn't work at the time — is now in striking distance of where I'd want it to be.
That's the real story. Timing is a variable you can't fully control. Position is one you can. We were both building position, and now the position has changed.
What I'd actually do, taking this back to the dream you can't let go of
Three things Gary said that I want to apply, one of which I'm already doing and two of which I need to do better:
- Build the relationship capital before you need it, with the specific people who'll matter when you do. Gary mentioned Brian Rolapp moving from the NFL to commissioner of the PGA — and made the point that he'd been having dinners with him for years, not because he needed something right then, but because he was playing chess moves. That's not networking in the hollow sense. That's understanding which relationships will be structurally important when the timing aligns and investing in them while they're still low-stakes. I've done some of this well. I've also let relationships sit dormant because the urgency wasn't there yet. Gary's framing changed how I think about that: the urgency you feel at the moment of the deal is too late to start the work.
- Know exactly what kind of asset you're building and what multiple it trades at — before you need that answer. Gary was clear about VaynerMedia: it's a services business, and services businesses trade at lower multiples than software or IP. He built it anyway, because it's the engine for everything else. But he knows the number honestly. Most people building businesses don't want to ask the multiple question because the answer might be uncomfortable. Gary asked it on himself, out loud, in front of me. The agency that generates enormous revenue is not the path to buying the Jets. VeeFriends might be. The Gary Vee brand creates options that money alone doesn't. The point is he holds all three with different expectations, and none of them with illusions.
- If you've put in eight years toward something that isn't going to become what you need it to be, the nine-year version doesn't get better. This is the one that hit me hardest, because it's the most counterintuitive. Gary told the story of a restaurant worker eight years in, scared to have the conversation with the owners about succession because they might say no — and he pointed out that the fear of wasting eight years is exactly the logic that wastes the next eight. The sunk cost isn't a reason to stay. It's the tuition you already paid for the knowledge you now have. "You're about to waste the next eight years." I've been in situations — on and off the field — where I knew the trajectory wasn't right and I let the investment of time become the reason to stay in it. It never worked out the way I hoped. The people who moved earlier always landed better.
The jersey Gary's mom knitted is in a safety deposit box. He's described exactly where it goes when he buys the team — front entrance, big structure, a plaque that says "You can do it too. From not being able to buy a jersey to buying the entire team."
The distance between that box and that entrance is a position problem. He's building the position.
So should we all.