'I got on my knees and begged': Kevin O'Leary wept over an ultra-rare Rolex, claims luxury watches can beat this 1 big asset. Do you own any?

Speaking with Money News Network, the Shark Tank investor recounted his years-long pursuit of one of the Swiss watchmaker’s rarest timepieces, the off-catalog Rolex Daytona, which he called the “Mystical Beast.”

O’Leary’s love of timepieces is well-known, and he once claimed “the watch market beat the S&P now for the eighth year in a row” at a Benzinga event in 2023. Since then, his appreciation and his collection have only grown.

“Grown men weep just looking at pictures of this Mystical Beast,” O’Leary said. “I got on my knees and begged for it. Begged.”

According to O’Leary, Rolex eventually summoned him to a private viewing in Los Angeles before the Academy Awards, where employees and local dealers gathered around the watch.

“The entire Rolex staff had never seen it,” he said.

When asked whether he cried after finally receiving the watch, O’Leary didn’t hesitate.

“I did,” he said. “I was weeping. It was mine. I own it. I have that piece. Do you know how many people have that piece? Maybe nobody.”

Are collectible watches really that great?

Ultra-rare luxury watches have become a legitimate collectible asset class, with some coveted Rolex models appreciating dramatically over time.

The luxury watches industry, preowned or not, is a $75 billion market as of 2023. The secondary market then stagnated for about 3-years, according to Fortune. However, in the last year, this market is up about 9.2% as of early August, based on data from WatchChart’s overall market index.

That said, luxury watches are among the least accessible markets available, often requiring deep industry relationships, months to years on waiting lists and a substantial fortune just to have the opportunity to buy in. You’d be sinking, at minimum, $3,800 (with papers) into something preowned that you might not even get to hold in your hand for half a year.

Fortunately, investors looking to diversify beyond traditional stocks and bonds don’t need to chase elusive luxury collectibles, let alone Rolexes.

Alternative assets like gold and real estate can offer portfolio diversification and are far more accessible, not to mention practical, for everyday investors.

Protect your purchasing power with physical gold

Unlike ultra-rare luxury watches, a straight investment into gold can’t be stolen. It’s also one of the world’s oldest stores of value, prized for its ability to preserve purchasing power during periods of inflation, economic uncertainty and market volatility.

That’s one reason central banks have been stockpiling the precious metal in recent years. According to the World Gold Council, they purchased just over 1,000 tonnes of gold in 2024 and 863 tonnes in 2025.

If you’re interested in adding precious metals to your retirement strategy, a gold IRA from Goldco allows you to hold physical gold and other IRS-approved precious metals while still enjoying the tax advantages of an IRA.

With a minimum investment of $10,000, Goldco also provides free shipping and access to a library of retirement resources. Plus, you can get up to 10% of qualified purchases in free silver.

If you’re curious whether precious metals could help diversify your retirement portfolio, you can download Goldco’s free gold and silver information guide to learn more. Just remember, gold is typically best used as only one part of an otherwise well-balanced portfolio.

Invest in real estate without becoming a landlord

Another potential option is real estate. Unlike a Rolex, real estate is a cornerstone of wealth-building because it can generate both rental income and long-term appreciation. The catch? Buying an investment property outright is expensive, to say nothing of the responsibility that comes with being a landlord.

But you don’t need to buy a property outright to participate in real estate anymore, or take on the headaches of property maintenance.

Arrived makes it possible to tap into the real estate market without buying an entire property yourself.

Backed by world-class investors, including Jeff Bezos, Arrived lets you invest in shares of SEC-qualified rental homes with as little as $100, giving accredited and non-accredited investors alike the opportunity to earn passive income and benefit from potential property appreciation.

Getting started is simple: Browse Arrived’s portfolio of professionally vetted properties, each selected for its income-generating and appreciation potential, then choose how much you’d like to invest.

And for a limited time, investors who open an account and fund it with at least $1,000 can also receive a 1% account match.

Private real estate for accredited investors

If you’re an accredited investor seeking exposure beyond publicly traded REITs and fractional ownership, Bonaventure offers access to institutional-grade multifamily real estate investments in high-growth markets with a minimum investment of $25,000.

The firm specializes in income-producing apartment communities and offers potential tax advantages through investment structures such as 1031 exchanges and UPREITs. Bonaventure also manages the underlying properties on investors’ behalf, allowing you to pursue passive income without the day-to-day responsibilities of property management.

Plus, Bonaventure has a fully-loaded resource center that teaches you everything you need to evaluate multifamily investments. Sign up today, explore your options and construct your real estate portfolio.

Invest in the finer things

Kevin O’Leary’s Rolex story highlights one of the biggest forces behind collectible investing: scarcity. The rarer an asset is, the more valuable it can become. That exclusivity also puts many collectibles out of reach for everyday investors.

Fortunately, there’s another collectible asset class that’s attracted billionaires for decades and has historically behaved very differently from the stock market. It’s also globally recognized by a wide network of collectors.

The asset in question? Fine art.