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Fascinated with real estate

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.

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.

He said he bought homes "all over the country" that he "never used." When he decided to offload his properties, Van Winkle says he was surprised by how lucrative the investments had been. “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.”

When one of his homes was destroyed by Hurricane Andrew in 1992, he decided to renovate it himself and sold it. This experience sparked a lifelong fascination with real estate. Van Winkle says he went to design school and worked as a general contractor for several years.

As of 2018, he was making $800,000 a year, according to court documents released during his divorce at the time.

All this experience buying and renovating homes gave him the tools he needed to craft a long-term business strategy.

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Strategic moves

After 30 years of investing in real estate, Van Winkle says he has developed a game plan. He says he prefers to buy properties that are off-market and not listed on the multiple listing service (MLS).

Off-market deals are rare. Only 3% of homebuyers surveyed by the National Association of Realtors in 2023 said they purchased their property directly from the seller or knew the seller instead of going through agents or online listing services.

He also buys distressed houses and property tax liens. He says he "puts out tax dockets on properties" which gives him a chance to buy the assets "for pennies on the dollar."

Renovating these properties adds value, but Van Winkle also uses the renovation process for content. His reality TV series "The Vanilla Ice Project" on the DIY Network has 180 episodes across 13 seasons, adding another source of income for the savvy entrepreneur.

This diversified real estate and media empire has helped the former rap star expand and preserve his wealth.

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Vishesh Raisinghani Freelance Writer

Vishesh Raisinghani is a freelance contributor at MoneyWise. He has been writing about financial markets and economics since 2014 - having covered family offices, private equity, real estate, cryptocurrencies, and tech stocks over that period. His work has appeared in Seeking Alpha, Motley Fool Canada, Motley Fool UK, Mergers & Acquisitions, National Post, Financial Post, and Yahoo Canada.

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