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There’s a long list of celebrities who made a fortune and lost it all. Kim Basinger, Mike Tyson and Curtis “50 Cent” Jackson have all filed for bankruptcy in the past, while Francis Ford Coppola has filed for bankruptcy three times (1).
Many may have believed Robert Van Winkle, better known as Vanilla Ice, would make that list after his music career withered away.
However, the rap star managed to build and maintain a business empire after he left the spotlight. Divorce records obtained by the Daily Mail showed that he was worth $9 million in 2018 (2). According to Celebrity Net Worth, his net worth is $25 million in March 2026 (3).
“I made millions for doing nothing!” Van Winkle told comedian Steve-O on an episode of Steve-O’s Wild Ride! in March 2024 (4).
Here’s how the one-hit-wonder built a lucrative real estate and media empire.
Van Winkle’s biggest career break was his hit song “Ice Ice Baby,” released in August 1990. The song was an instant hit and went on to become the party anthem of the 90s.
“We were selling a million records a day, easy,” he told Steve-O during the podcast.
Unfortunately, Van Winkle’s rap career nosedived after “Ice Ice Baby” — but the track was successful enough to help him accumulate a large portfolio of real estate.
“When I did ‘Ice Ice Baby,’ I made a lot of money,” he shared in a YouTube video from March 2026 (5). “And then, instead of blowing it like a rock star, I took that money and I started buying homes. I wasn’t buying them to invest — I bought them to actually live in.”
But when he ultimately decided to offload his properties, Van Winkle said he was surprised by how lucrative the investments had been. He told Steve-O, “They sold really quick and I made millions for doing nothing! I didn’t even change the carpet … and I go holy s— let’s go buy a bunch more of them (4).”
While you may not have an era-defining hit like “Ice Ice Baby” to your name, you can still get into the real estate market with your current bankroll.
If that interests you, consider tapping into this market through real estate platforms like Arrived.
Backed by world-class investors, including Jeff Bezos, Arrived allows you to invest in shares of vacation rentals, earning a passive income stream without the extra work that comes with being a landlord of your own rental property.
To get started, simply browse through their selection of vetted properties, each picked for their potential appreciation and income generation. Once you choose a property, you can start investing with as little as $100, potentially earning monthly dividends.
Plus, for a limited time, when you open an account and add $1,000 or more, Arrived will credit your account with a 1% match.
Read More: I’m almost 50 years old and don’t have retirement savings. Is it too late?
After more than 30 years of investing in real estate, Van Winkle says he has developed a game plan. He told Steve-O that he prefers to buy properties that are off-market and not listed on the multiple listing service.
However, off-market deals are rare. In fact, according to 2025 data from the National Association of Realtors, only 5% of home sales between July 2024 and June 2025 were “For Sale By Owner” transactions, an all-time low (6).
An alternative investment option? Multifamily and industrial rentals. Both have a strong outlook for 2026, making now an ideal time to get in the game (7).
If diversifying into multifamily and industrial rentals appeals to you, you could consider investing with Lightstone DIRECT, a new investing platform from the Lightstone Group, one of the largest private real estate companies in the country with over 25,000 multifamily units in its portfolio.
Since they eliminate intermediaries — brokers and crowdfunding middlemen — accredited investors with a minimum investment of $100,000 can gain direct access to institutional-quality multifamily opportunities. This streamlined model can help reduce fees while enhancing transparency and control.
And with Lightstone DIRECT, you invest in single-asset multifamily deals alongside Lightstone — a true partner — as Lightstone puts at least 20% of its own capital into every offering. All of Lightstone’s investment opportunities undergo a rigorous, multistage review before being approved by Lightstone’s Principals, including Founder David Lichtenstein.
How it works is simple: Just sign up with your email, and you can schedule a call with a capital formation expert to assess your investment opportunities. From here, all you have to do is verify your details to begin investing.
Founded in 1986, Lightstone has a proven track record of delivering strong risk-adjusted returns across market cycles with a 27.6% historical net IRR and 2.54x historical net equity multiple on realized investments since 2004. All told, Lightstone has $12 billion in assets under management — including in industrial and commercial real estate.
As such, even if multifamily rentals don’t appeal to you, Lightstone could still serve you well as an investment vehicle for other real estate verticals.
Get started today with Lightstone DIRECT and invest alongside experienced professionals with skin in the game.
While investing in alternative assets like real estate can be an excellent strategy for developing wealth — as proven by Van Winkle — there are other asset classes worth considering.
One such asset has posted positive returns over 20 years, highlighting strong long-term investment potential. And with its moderate relationship with traditional financial markets, this alternative investment could help protect against inflation, especially amid recent economic uncertainty surrounding the war.
It’s no wonder why this asset has long been favored by the ultrawealthy as a resilient and lucrative addition to their portfolios: With an estimated value of over $2.5 trillion — projected to reach nearly $3.5 trillion by 2030 — it represents a massive asset class, according to the 2025 edition of the Deloitte Private and ArtTactic Art & Finance Report (8).
Are you surprised to discover the asset is fine art?
Until recently, this world was off-limits. Now, with Masterworks, you can buy fractional shares in multimillion-dollar works by icons like Banksy, Picasso and Basquiat. While art can be illiquid and typically requires a long-term hold, it offers unique portfolio diversification.
Masterworks has sold 27 artworks so far, yielding net annualized returns like 14.6%, 17.6% and 17.8%.*
For example, they recently acquired a work by Barbara Peyton and offered investment at $1.16 million. Just 17 days later, Masterworks accepted a buyer’s offer of $1.5 million — netting 22.9% back to investors.
Moneywise readers can get priority access to diversify with art: Skip the waitlist here.
*Past performance is not indicative of future returns. Investing involves risk. See important Regulation A disclosures at Masterworks.com/cd.
Van Winkle’s success is not only about luck, but also his resilience.
For example, when one of his homes was destroyed by Hurricane Andrew in 1992, he decided to renovate it himself and sell it. This experience sparked a lifelong fascination with real estate.
Van Winkle also said on the podcast with Steve-O that he went to design school and worked as a general contractor for several years (4).
As of 2018, he was making $800,000 a year, according to the Daily Mail (2). All this experience buying and renovating homes gave him the tools he needed to craft a long-term business strategy.
In other words, his expertise allowed him to strategize effectively in order to maximize his investments.
If you need help from an expert with strategizing for your own investments, a financial advisor can crunch the numbers and help you build a financial plan that works.
But hiring an advisor can be a lifelong commitment, which might make or break your retirement. Finding reliable advisors is crucial — and that’s where Advisor.com can come in. The platform connects you with an expert near you for free.
Advisor.com does the heavy lifting for you, vetting advisors based on track record, client ratios and regulatory background. Plus, their network comprises fiduciaries, who are legally required to act in your best interests.
Just enter a few details about your finances and goals, and Advisor.com’s AI-powered matching tool will connect you with a qualified expert best suited for your needs based on your unique financial goals and preferences.
Finding the right advisor isn’t always easy — there’s no one-size-fits-all solution. That’s why Advisor.com lets you set up a free initial consultation with no obligation to hire to see if they’re the right fit for you.
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We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
The Independent (1); Daily Mail (2); Celebrity Net Worth (3); @SteveOsWildRideClips (4); @officialvanillaice (5); National Association of Realtors (6); JPMorgan Chase (7); Deloitte (8)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
