Shark Tank’s Kevin O’Leary wore a $30M, white gold NBA amulet to the Oscars, but his money advice is more modest. How to invest like 'Mr. Wonderful'

The price tag for his jewelry ensemble? An estimated ceiling of $30 million.

O’Leary had one end in sight: “When I walk that red carpet at the Oscars, grown men are going to weep (2).”

It’s the kind of flex that grabs attention — sparking the usual mix of awe and skepticism. But while the diamonds stole the spotlight, there’s a deeper financial story hiding beneath the shine, and a lesson for investors, too.

O’Leary’s impressive collection

O’Leary’s necklace isn’t just jewelry — it’s a collectible asset disguised as fashion.

O’Leary’s Triple Logoman card is a one-of-one piece from Upper Deck’s 2004 Exquisite All-NBA Pass Collection. According to reports, the card has never been sold at auction, making its value largely driven by scarcity and demand (3).

And the way it’s presented matters just as much as the asset itself. The mint condition PSA 10-graded card is housed inside a bespoke Tiffany & Co. case — designed with roughly 2.2 pounds of white gold, set with diamonds and rubies, then attached to a chain (4).

This isn’t the first time O’Leary’s outfit has stolen the spotlight.

Earlier this year, he wore another high-value piece to the Screen Actors Guild Awards — a dual Logoman card featuring patches from Michael Jordan and Kobe Bryant, both signed and similarly encased by Tiffany.

These purchases weren’t made on a whim. They’re part of a pattern of investment.

In 2025, O’Leary teamed up with collectors Matthew Allen and Paul Warshaw to acquire that dual Logoman card for $12.9 million — breaking the previous record held by a 1952 Mickey Mantle card that sold for $12.6 million (5).

Ultra-wealthy investors are betting big on collectibles

Among ultra-high-net-worth investors, collectibles — from sports cards to paintings — are increasingly used to diversify away from traditional markets like stocks and real estate.

In fact, high-end sports cards have seen explosive growth in recent years, with rare, one-of-one pieces selling for millions and even appreciating significantly after purchase.

For investors like O’Leary, collectibles aren’t the foundation of wealth — they’re a strategic layer on top of an already diversified portfolio. Like alternative assets, collectibles as an investment are intended to store their value away from markets, providing some insulation if stocks and bonds tumble together.

But this investing philosophy goes far beyond collectible NBA cards.

In fact, ultra-high-net-worth individuals are adding another niche collectible to their growing portfolio of alternative assets

They’re putting more money behind it, too. Allocations to this specific asset rose to 20% in 2025 from 15% the year before, with those worth over $50 million boosting that share to 28%, according to research by UBS (6).

And despite typically being the domain of the wealthy, retail investors now have the chance to invest in this historic asset class.

The collectible asset in question? Post-war and contemporary art.

A finer alternative

Until recently, this world was off limits to most retail investors. After all, finding a way to purchase a historically significant painting once relied on access to a complex network of curators, appraisers and galleries.

Now Masterworks has opened the door to investing in art for retail investors — with more than 70,000 users taking charge with art since 2019. Depending on availability, it’s possible to own fractional shares of works by artists such as Banksy, Basquiat and Picasso.

Masterworks has sold 27 artworks so far, yielding net annualized returns like 14.6%, 17.6%, and 17.8% among assets held for longer than a year.

Masterworks’ most recent sale highlights another trend — faster exits beyond the more typical medium-hold period. Just 17 days after buying an Elizabeth Peyton painting for $1.16 million, it sold for $1.5 million — netting a 22.9% return for investors quick enough to buy in.

If diversifying with art as an investment sounds intriguing, Moneywise readers can get priority access to invest with art and skip the waitlist to see what’s on offer.

Note that Past performance is not indicative of future returns. Investing involves risk. You can see important Regulation A disclosures at Masterworks.com/cd.

Can you handle the risk?

Collectibles are exciting, but can be highly volatile. Rare cards have sold for millions, driven by hype, nostalgia and superstar athletes. But it’s still a speculative asset class.

Even O’Leary’s $30 million piece is technically an estimate — because the card has never been sold publicly, making its true market value uncertain.

Their value comes down to one thing: what someone else is willing to pay. That’s why seasoned investors often balance these types of assets with more stable holdings — especially in uncertain economic or political environments.

According to O’Leary, one of those stabilizers a certain precious yellow metal, which he has described as a long-term wealth anchor he continues to buy.

Hedge your portfolio with gold

For all the hype around sports cards and diamond-studded necklaces, Kevin O’Leary’s core strategy is a lot more grounded.

He’s been holding gold for decades — and hasn’t changed his stance.

“I’ve owned gold for over 30 years, about 5% of my portfolio,” he recently shared on LinkedIn, claiming that when systems fail, gold still does its job (7). He’s not alone in this belief, with financial gurus like Robert Kiyosaki of Rich Dad, Poor Dad fame and ex-CEO of Bridgewater Associates Ray Dalio extoling golden virtues.

Their argument is simple: Assets like gold tend to hold their value when markets get shaky, acting as a potential hedge during trying times.

And lately, those uncertain times have been front and center.

As geopolitical tensions and economic uncertainty picked up, gold surged to record highs earlier this year, briefly crossing $5,000 in January. Over the past year, gold has gained around 60%, making it one of the best-performing assets of the year (8).

But O’Leary’s gold strategy might be difficult to follow.

"I like to touch my gold, so I actually own the bullion," he said during an interview with WIRED, "but when you own the bars, you have to pay for storage. You're not gonna walk around and put it under your mattress, you gotta put 'em in a safety deposit vault and you pay for that (9)."

Invest in gold without worrying about storing it

For those without a direct line to gold bars or coins, one option is to work with a broker or dealer.

You can open a gold IRA with the help of Priority Gold — combining the hedging properties of gold with the tax advantages of an IRA.

If you opt for their platinum package, you can get free account setup, storage, and insured shipping for up to five years. And if you ever want to sell your gold, they offer hassle-free and guaranteed buyback assurance without any added fees.

You can even request a free wealth preservation guide to learn more about how a gold IRA can help preserve your wealth.

The best part? you can get $10,000 in complimentary silver when you make a qualifying purchase. Just keep in mind that gold is often best used as one part of a well diversified portfolio.

O’Leary’s real estate take

If high-end NBA cards represent the flashier, high-upside side of O’Leary’s portfolio, assets like real estate sit at the opposite end of the spectrum.

One of O’Leary’s core investing rules is simple: own assets that pay you to hold them.