Tiffany Haddish Explains the Unexpected Advice Behind Her Expansive 17-Property Real Estate Portfolio

Years ago, comedian Tiffany Haddish received financial advice from an unexpected stranger, and now, she credits the life-changing words of wisdom as the reason she currently owns 17 properties.

During an appearance on a live recording of the podcast “Family Trips With the Meyers Brothers,” late night personality Seth Meyers and his brother, Josh Meyers, asked Haddish about the kinds of vacations she likes to take.

“My favorite kind of trips is groups. That’s why I was so heavy into Groupon for a long time, and I’m still heavy into it. I still do Groupon vacations,” the “Girls Trip” star said. She added that she enjoys traveling with a group of strangers because she usually learns something new.

During one group trip—to China and Japan on a discounted deal—she met an accountant who left a lasting impression.

The accountant encouraged her to read a book called “The Weekend Millionaire’s Secrets to Investing in Real Estate: How to Become Wealthy in Your Spare Time,” by Mike Summey and Roger Dawson. The book provides strategies for building consistent wealth over time.

“The accountant said, ‘If you’re doing movies and you think you’re going to make it, when you start making money, buy a piece of property every year for 15 years. No matter what happens with your career, you’ll be successful. They can never cancel you or stop you,’” she shared.

“If you have land, you’ll be a multimillionaire, even with 10 properties,” Haddish added. She now has “like 17” in her portfolio, because she invests in a property each time she stars in a movie.

Haddish’s expansive collection of property is a significant development from where she started at the beginning of her career. She has previously opened up about experiencing homelessness in her early days as a comic, as well as the time she spent in foster care as a child.

During a 2024 appearance on “This Life of Mine With James Cordon,” Haddish recalled the helping hand she received from comedian Kevin Hart when she worked with him to perform sketch comedy shows at the Laugh Factory in Los Angeles.

Hart began to suspect Haddish was experiencing homelessness when he noticed that her car was filled with personal belongings.

“I would show up late. I didn’t want nobody to see my car. I would park a little farther away, or I would pull up and let the valet take the car, but I would pull up late so nobody would see,” she explained in 2024.

Although she tried to “avoid” talking to Hart about her living situation, the “Ride Along” star refused to drop it. Hart gave Haddish $300 that night, which she used to cover a hotel room. Soon after, he put Haddish in touch with a real estate agent who could help her find housing.

“It needed so much work,” she said of the apartment she eventually found. “It was disgusting, and I looked around and I was like, ‘Wow.’ I saw roaches. It was bad.”

But the rent was $500 a month, so Haddish took the spot.

“I still have that place,” she confirmed in 2024. “I still have it. I had to fix it up myself and I still got it.”

In a 2022 Cosmopolitan cover interview, Haddish detailed the frugal budgeting she relied on to buy her very first house after appearing on “The Carmichael Show” in 2015.

“Before we even got into Season 2 of ‘The Carmichael Show,’ I bought a house,” she said. “Everybody told me I should wait, but I didn’t care. I just knew I was going to have to always make enough money to take care of me and the house, and that’s what I did.”

“Between that show’s next season, the ‘Keanu’ movie, and making sure I can live comfortably off of $500 a month, I was able to pay off half the house,” she added. “The ‘Girls Trip’ check was the final check. People told me to spend it other ways, but I used it to pay off the house because I was always afraid of being homeless again.”

Noting that despite the “surplus of money” she has as a result of her success, she remains mindful of her finances. She also told the magazine she wishes to retire “and buy a ranch in Wyoming.”