Everywhere you go in New York City, you encounter the hustle. The streets are full of people striving to make their dreams come true.

In this episode, we delve into the fascinating world of watch flipping with a local expert, exploring how this unique hustle operates in the heart of the city.

Diving into the Diamond District

New York City’s Diamond District is a bustling hub rich with opportunity. Watches and diamonds exchange hands daily, creating a dynamic environment for those looking to profit. Here, time is money in the most literal sense.

Setting up shop in this district isn’t easy. The local watch flipper started with a modest $5,000 and hustled his way up by moving around booths, selling watches he bought online.

Despite the challenges, the allure of the hustle and the potential for profit keep people coming back. The key is perseverance and a bit of street smarts.

The Emotional Side of the Business

While watch flipping might seem purely transactional, there’s an emotional side too. Buyers often seek watches for significant life events, adding a layer of sentiment that can complicate deals.

However, successful flippers remain detached. They see each transaction as a business move, focusing solely on the profit margins.

Some of the most sought-after pieces include custom watches adorned with diamonds, which require buyers to pay a premium.

Investment Insights

Not all watches are created equal. The flipper advises that sticking to classic models like steel and two-tone Datejusts can be a reliable way to make steady profits.

Vintage pieces from the 70s, 80s, and 90s are particularly valuable. They offer a dependable market with moderate margins.

Even in a bustling market, it’s possible to start small and gradually build your business with the right strategy.

Real Estate and Mobility

In this line of work, having a physical storefront isn’t always necessary. Many flippers find success by moving from booth to booth, making deals on the go.

Mobility allows them to adapt quickly to market changes and seize opportunities as they arise.

However, this nomadic approach comes with risks, including the potential for theft. Discretion is key.


Daily Transactions

Transactions occur multiple times a day. Each deal has the potential to make or break a flipper’s daily earnings.

Quick decisions and keen eyes for value are crucial skills in this fast-paced environment.

Each sale is an opportunity to refine strategies and improve margins, making every transaction a learning experience.

Negotiating Deals

Negotiation is an art in the watch flipping business. Prices are never set in stone, and every deal is a test of skill and knowledge.

Being able to read the market and understand the value of each watch is essential to making profitable deals.

Even when faced with losing propositions, skilled flippers know how to pivot and find a way to turn things around.

Passing the Baton

Learning the ropes of watch flipping is not just about knowledge. It’s also about the practical experience of negotiating and closing deals.

Veterans in the field often mentor newcomers, teaching them the intricacies of the market and the art of the deal.

Every watch sold and every dollar earned is a testament to the hustle and the grind of this unique business.


Watch flipping in New York City’s Diamond District is a high-stakes, high-reward hustle.

It requires a keen eye for value, strong negotiation skills, and the ability to stay calm under pressure.

For those willing to put in the work, the potential for profit is significant, making it a compelling venture in the city that never sleeps.

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