Jun 17, 2024
There’s a long list of celebrities who made a fortune and lost it all. Burt Reynolds, Mike Tyson and Curtis “50 Cent” Jackson have all filed for bankruptcy in the past. Francis Ford Coppola has filed for bankruptcy three times.
Many believed Robert Van Winkle, better known as Vanilla Ice, would find himself on that list after his music career withered away.
Advertisement
However, the rap star has managed to build a business empire after he left the spotlight. Divorce records obtained by the Daily Mail showed that he was worth $9 million in 2018. According to Celebrity Net Worth, his net worth is now at $20 million.
“I made millions for doing nothing!” Van Winkle told comedian Steve-O on a recent episode of his podcast "Steve-O's Wild Ride!"
Here’s how the one-hit-wonder built a lucrative real estate and media empire.
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.
Advertisement
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.
Must Read
- Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake — here’s what it is and the simple steps to fix it ASAP
- Robert Kiyosaki begs investors not to miss this ‘explosion’ — says this 1 asset will surge 400% in a year
- Vanguard reveals what could be coming for U.S. stocks, and it’s raising alarm bells for retirees. Here’s why and how to protect yourself
Join 250,000+ readers and get Moneywise’s best stories and exclusive interviews first — clear insights curated and delivered weekly. Subscribe now.
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.
You May Also Like
- Turning 50 with $0 saved for retirement? Most people don’t realize they’re actually just entering their prime earning decade. Here are 6 ways to catch up fast
- This 20-year-old lotto winner refused $1M in cash and chose $1,000/week for life. Now she’s getting slammed for it. Which option would you pick?
- Warren Buffett used these 8 repeatable money rules to turn $9,800 into a $150B fortune. Start using them today to get rich (and stay rich)
- Here are 5 easy ways to own multiple properties like Bezos and Beyoncé. You can start with $10 (and no, you don’t have to manage a single thing)
Vishesh Raisinghani is a financial journalist covering personal finance, investing and the global economy. He's also the founder of Sharpe Ascension Inc., a content marketing agency focused on investment firms. His work has appeared in Moneywise, Yahoo Finance!, Motley Fool, Seeking Alpha, Mergers & Acquisitions Magazine and Piggybank.
