The Grey Market Middlemen Quietly Running The Watch World

• Grey market watch dealers turn Instagram and TikTok into theatres of trade, flipping watches for audiences in the millions
• New collectors view watches as assets rather than heirlooms, chasing margins, speed and liquidity instead of movements, milestones or sentimentality.
• Rolex dominates the resale spectacle, with Daytonas, Submariners and GMTs providing the liquidity that fuels fast flips and fuels the entertainment economy of watch culture.

Watch collecting has always been a deeply personal expression; a way to mark milestones like a graduation, a wedding or a promotion.

A watch could hold more value than the metal and mechanics it was built from, carrying stories for the collector and, in some cases, the seller. That idea is starting to change.

A new generation has discovered watches not through heritage or horological detail, but through Instagram reels and TikTok streams.

Dealers film fast-paced trades on sidewalks, rooftops and penthouses, turning a Daytona flip into content for hundreds of thousands to watch. Vookum, one of the most recognisable figures in this space, has more than 430,000 followers watching him parade through New York with the equivalent of a year’s tuition stuffed into both hands. The deal is the performance, and the performance is the deal.

These middlemen have transformed the grey market into a spectacle to be viewed by the social media masses. Each reel feels like a scene from Uncut Gems: stacks of cash, briefcases of watches, and New York characters each getting their 15 minutes.

The timepiece itself matters less than the margin on the flip, the buzz it generates online and the speed with which it changes hands. This emerging phenomenon is driving the grey market, and making celebrities out of the middlemen secretly running the watch world.

Instagram Watch Dealers Become Entertainment

The new grey market thrives on visibility. What used to be private transactions between dealers and collectors now plays out live on social media with the likes of Vookum, Wristcheckers, and other high-profile flippers turning their Instagram feeds into marketplaces with built-in reality TV drama.

Celebrities like Pete Davidson and Alex Eubank have also made appearances across these fast-flipping channels, bringing their audiences (which exceed millions) with them.

Videos show Submariners still in plastic on the boutique floor, Audemars Piguet Royal Oaks shuffled across hotel lobbies, and Patek Philippe Nautiluses changing hands faster than a bar tab. Every trade is filmed, presented, packaged and posted for mass consumption.

Celebrities like Pete Davidson and Alex Eubank have also made appearances across these fast-flipping channels, bringing their audiences (which exceed millions) with them. And the audiences are lapping it all up.

Why Collectors Are Hooked On The Grey Market

The grey market has always been there, but social media transformed it into something else entirely. The spectacle of seeing flippers like Vookum picking up luxury timepieces that we can only dream of purchasing at an AD, walking through the streets of Manhattan (fist clasped, I should add) and profiting $1,000 in a single flip.

The flips in turn become storylines, the margins become plot twists, and the personalities behind the trades become the stars. It’s a rush to see a Daytona flip for profit in under an hour. It’s the thrill of watching stacks of cash changing hands on camera, often out in the open, as another deal is sealed.

It speaks directly to a new kind of watch collector, ones that are less inclined to chase sentimental pieces they intend to hold for a lifetime or hand down. They’re looking for leverage, for the trade, for the quick upside. For them, a Daytona can appreciate more in a week than it can while sitting on their wrist for a decade.

The grey market reels tap into a broader cultural trend: luxury goods as performance assets. Sneakers, handbags and jewellery are thriving during this economic downturn because of limited supply and high resale value. Watches are the same, except the gains are instant, and designed for public consumption.

Rolex, Daytona And The Rise Of The Flip

Of course, the products still matter, and where there’s profit to be made, Rolex remains the crown jewel of the watch world. Diamond-set Daytonas, sleek Submariners and GMTs are the backbone of the internet’s middle market, providing the liquidity that makes this content possible.

Daytonas, in particular, are perfect content. They’re scarce at retail, valuable on the secondary market and have the cultural clout that makes a fast flip instantly understandable to anyone watching. When a dealer flashes a Daytona, viewers already know what it means: money, status and a trade about to happen.

Other brands like Audemars Piguet, Richard Mille and Patek Philippe feature heavily, but Rolex dominates because it represents both aspiration and liquidity. You don’t need to be a seasoned collector to understand the appeal of a stainless-steel sports watch moving hands on Instagram.

The New Grey Market Personalities

The middlemen driving this trend are as important as the watches themselves. Vookum has become the poster boy, publishing his lived-experience street hustle alongside the watch world’s luxury cachet. His reels are part sales pitch, part performance art and turning his day-to-day trades into bingeable content.

Transparency is key to building trust with audiences, flashing prices and tough negotiations in real time. Followers feel like they’re part of the action, even if they never buy a watch, offering a peek through the looking glass of a world we’re not supposed to be involved in.

This is retail as theatre, and the personalities who can create the most engaging shows are the ones winning market share.

Risks Behind The Hype

The grey market middlemen thrive on speed, but speed is also where mistakes and disputes happen. It is a world where trust is built on reputation, not formal paperwork, and one where buyers need to know exactly who they’re dealing with.

For many viewers, that risk is irrelevant because hey’re there to be entertained. But for the buyers wiring money off the back of these reels, the risk is significant. Once the deal is done, there is little recourse if something goes wrong and they’re left holding onto deadwood.

Why The Grey Market Matters To The Future Of Watch Collecting

The grey market shapes perception in ways the traditional industry no longer controls, training a new generation of collectors to view timepieces as assets rather than heirlooms, shifting the focus from milestones to margins.

Auction houses will always continue to hold influence, and boutiques remain the official entry point for new releases. Yet for many first-time buyers, social media now provides the primary impression of watch culture. Instagram reels and TikTok streams post rapid trades, stacks of cash and dealers who treat watches like financial instruments on a trading floor.

This evolution signals a broader change in the industry’s balance of power, where speed and liquidity have seemingly replaced tradition. Grey market dealers, using their platforms and reach, are actively reshaping the culture of watch collecting in real time.

For the new generation of collectors, a Rolex Daytona is more valuable in motion than it is sitting in a box. The watch is a vehicle, the flip is the story, and the dealer is the star, Whether it involves a seasoned collector or someone chasing a single piece, contemporary watch culture has never looked more chaotic… and we can’t take our eyes off it.