Ice Ice Baby to Real Estate Tycoon

Many celebrities, like Burt Reynolds and Mike Tyson, have experienced a rise and fall in wealth. Vanilla Ice, despite a declining music career, has built a successful business empire, increasing his net worth from $9 million in 2018 to $20 million now. He credits his wealth to savvy investments, stating, “I made millions for doing nothing!”

A Newfound Passion: Real Estate

After the success of “Ice Ice Baby,” Vanilla Ice invested in numerous homes across the country, despite his declining music career. He never used these properties, but when he sold them, he was surprised by the substantial profit he made. This led him to realize the potential in real estate and inspired him to invest further.

A turning point came in 1992 when one of his homes was destroyed by Hurricane Andrew. He took it upon himself to renovate and sell it, igniting a lifelong passion for real estate. This led him to design school and a stint as a general contractor.

By 2018, he was earning $800,000 a year, as revealed by court documents during his divorce proceedings.

Strategic Investments: The Game Plan

With 30 years of real estate investment under his belt, Van Winkle has honed a strategic approach. He prefers off-market properties, not listed on the multiple listing service (MLS). Such deals are rare, with only 3% of homebuyers in a 2023 survey by the National Association of Realtors reporting direct purchases from sellers or acquaintances.

He also invests in distressed houses and property tax liens, “putting out tax dockets on properties” to buy assets “for pennies on the dollar.”

Renovations not only add value to these properties but also provide content for his reality TV series “The Vanilla Ice Project” on the DIY Network. With 180 episodes across 13 seasons, the show serves as an additional income stream.

This diversified portfolio of real estate and media ventures has enabled the former rap star to not only expand but also preserve his wealth.