Gary Vaynerchuk on collectibles eating contemporary art, pickleball's Anna Leigh Waters, and the generational run at 50

Gary Vaynerchuk on collectibles, alternative sports, and the generational run at 50

Gary Vaynerchuk's central argument is simple: collectibles are eating contemporary art, and most of the market hasn't priced that in yet.

Vaynerchuk says he has spent the last seven to ten weeks in what he calls a "cocoon" around a thesis he has been building for eight years — that collectibles are becoming the next major lifestyle genre. His tell is behavioral: the money that a generation ago flowed into blue-chip contemporary art for the home is now going into six- and seven-figure trading cards and physical collectibles. He points to Michael Rubin and the Tops empire as the cultural catalyst, and to trading cards' hundred-year history as evidence this isn't a fad.

The practical bet is already made. VaynerMedia has launched a dedicated collectibles marketing division, modeled on how Coca-Cola built a sports marketing division when the Olympics became commercially important. His prediction: within ten years, every Fortune 500 CPG and apparel brand will have a collectibles marketing strategy, driven by the need to create differentiation in a world where AI-powered agentic commerce makes commodity reordering the default.

---

“I am building the next Disney Pokemon marble all in everyone's face. It's called VeeFriends. I believe collectibles have eaten up the pop culture energy of what young 20 year olds would do with public stocks. Instead of buying 50 shares of Nike, they're going to go buy a collectible.”

Pickleball as proof of concept

Vaynerchuk bought a Major League Pickleball team for $500,000 pre-COVID. It is now trading at $16 million. His investment logic wasn't television viewership — it was that pickleball highlights over-indexed on social media even seven years ago, and alternative leagues no longer need ESPN or Fox Sports to say yes.

To make the collectibles case live, he asks for an eBay search on Anna Leigh Waters — the star player Vayner Sports represents — filtered to completed and sold listings. The result: rookie autograph cards selling for $5,000 to $8,000. His point is that 99% of the audience has never heard of her, which means collectible markets are running well ahead of mainstream awareness. Waters is the only athlete in a major sport who is the best player regardless of gender, which Vaynerchuk treats as a unique marketing asset.

---

The alternative sports investment framework

The screening criterion is social media over-indexing, not broadcast deals. Vaynerchuk is invested in sailing, slam ball, pickleball, and a nascent wiffle ball league, and his rationale across all of them is the same: the internet removes the gatekeeper that once made ESPN's approval necessary. He draws the analogy to football and television — football wasn't a great radio sport and only exploded once the medium matched the format. Streaming and short-form social are the new television, and the sports that generate shareable highlights will find their audiences without traditional distribution.

He is also explicit that the participation-to-viewership conversion is historically misread. The knock on pickleball — that everyone plays it but nobody watches — mirrors what critics said about tennis and golf decades ago.

---

VeeFriends and the longer build

Vaynerchuk describes VeeFriends, his collectibles IP, as the project he is building to become "the next Disney, Pokémon, Marvel" — a claim he wants clipped and revisited in a decade. Because he runs thirteen other businesses simultaneously, he says the project gets underestimated. His view is that building an IP-driven collectibles business during the current AI era will turn out to be one of his shrewdest moves, though he offers no revenue figures or timeline.

---

On being 50

At 50, Vaynerchuk argues that entrepreneurs are structurally different from athletes. Athletes peak and then face a hard stop; entrepreneurs — he uses Buffett as the reference point — can be running their best decades well into their seventies and eighties. He says he genuinely wonders whether he is entering his prime, not as performance anxiety but as conviction. That framing is the spine of everything else he says: the collectibles thesis, the sports investments, the VeeFriends build. He isn't winding down. He thinks the run is just starting.