'I made millions for doing nothing!' How Vanilla Ice amassed a $25M real estate empire — and how to follow his strategy

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.

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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.

You can tap into this market by investing in shares of vacation homes or rental properties through Arrived .

Backed by world-class investors, including Jeff Bezos, Arrived allows you to invest in shares of vacation and rental properties , 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 .