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At 27, she owns 26 properties and is holding a contest to renovate rooms in five Philly homes | We The People

After inheriting her grandmom's South Philly house when she was 20, Jamisa McIvor-Bennett became a real estate investor.

A We the People profile: Jamisa McIvor-Bennett is in one of the 26 properties she owns June 24, 2021. She inherited her grandmother's South Philly home and sold it, using the money to invest in real estate.
A We the People profile: Jamisa McIvor-Bennett is in one of the 26 properties she owns June 24, 2021. She inherited her grandmother's South Philly home and sold it, using the money to invest in real estate.Read moreTOM GRALISH / Staff Photographer

Meet Jamisa McIvor-Bennett, a self-taught real estate investor and founder of Rosebud’s Investments.

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Jamisa McIvor-Bennett will never forget how her Grandmom Rose cried on the day they went to a notary together to add her name to the deed of her grandmother’s South Philly home.

Her tears flowed so much the notary asked McIvor-Bennett’s grandmother if she was sure she wanted to go through with it.

She didn’t hesitate.

“‘Yes,’” McIvor-Bennett recalled her Grandmom Rose saying. “‘I’m just very proud.’”

When her grandma unexpectedly died a few months later of natural causes, McIvor-Bennett suddenly found herself a first-time homeowner at the age of 20.

The gift came with a wealth of questions, and a bit of family drama, too, from relatives who thought they had greater claim to the property than she did.

“They pretty much wanted to see me fail,” she said. “I showed them what failing forward looks like.”

McIvor-Bennett, who was then working as a cashier at ShopRite, sold the property for $152,000 a few months later and used the money to invest in nine more properties. Then more, and more.

Now the 27-year-old married mother of four owns 26 properties in the Philly area — 25 of them outright, without a mortgage — and she’s teaching others from her community how to do it, too.

“I was like, people need to know this!” she said. “And I think it has to be from a person that says, ‘I come from where you come from, I’ve done what you need to do. This is the outcome. It’s not a myth.’”

McIvor-Bennett, whose parents were young, grew up in South Philly with her great-grandma Hazel, who often worked long hours.

“For the most part I raised myself, and that plays a big part of who I am today,” she said.

After graduating from Philadelphia Electrical and Technology Charter High School in 2012, McIvor-Bennett attended Lock Haven University but dropped out her sophomore year when the college’s partying culture became too much.

“By the time they started passing the Everclear around, I was like, ‘I have to go home, it’s crazy here,’” she said.

When she came back to Philly, McIvor-Bennett had jobs as a home health-care companion and as a personal assistant for a businessman who lived in Chestnut Hill.

“That’s when I discovered Philadelphia has a place like Chestnut Hill,” she said. “It was like, ‘Wait? You guys live like this? And it’s only one SEPTA bus ride away?’”

She also worked as a cashier at ShopRite and helped her Grandmom Rose, the daughter of the great-grandmother who raised her, with grocery shopping, bills, and chores.

When her Grandmom Rose died and McIvor-Bennett was willed her South Philly home, she wanted to renovate it and live there, but the contractors she consulted with gave her estimates she couldn’t afford. Some even offered to buy her house, for about $40,000.

“I was in the middle of gentrification. I didn’t know what was happening,” she said.

A neighbor familiar with McIvor-Bennett’s situation gave her his Realtor’s number, in case she wanted to sell the house.

She met with the Realtor, who listed the house at $115,000. A bidding war began and it sold for $152,000.

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When she went to the closing, McIvor-Bennett brought her newborn son and the Realtor came with a financial adviser, who suggested she put her money in a Roth IRA. But McIvor-Bennett didn’t like the idea of having to pay fees on her own money if she wanted to take it out early.

“He said, ‘That’s a lot of money. What are you going to do with it?’ I said, ‘I’m going to buy more houses. If one house got me this much, I could get some more.’” she said. “They said, ‘It’s not easy.’”

When the Realtor called her after the closing, McIvor-Bennett let him know she was upset.

“I told him I felt disregarded because I’m young, I have a baby, and I’m Black. I felt like you guys made it seem like I am incapable of making good decisions,” she said.

The Realtor tried to make it right by introducing her to an investor, who told McIvor-Bennett she could have taken equity out on her home to fix it up and then flipped it for top dollar.

“At that table at a corner bakery at City Line, he told me that I left some money on the table, and I immediately made a point to go and find it,” she said.

McIvor-Bennett began by buying nine properties, but not all of them were winners. A house in West Philly she bought sight unseen for $6,500 had a tree growing through it. But each time she made a deal, she learned more.

She attended real estate school for a while but realized she prefers investing. Most of the properties she owns are residential in the Philly area, and she rents them, preferring to have a steady income from tenants rather than just flipping houses.

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Along the way, she began telling others how to do what she did, and in 2017 she founded Rosebud’s Investments, which offers services for new investors. The company is named after her grandmother.

Today, McIvor-Bennett works with everyone from first-time buyers to NBA players to help them navigate the real estate investment industry.

“I’m doing it with the people of the community, and I’m also doing it with millionaires,” she said. “I understand because I’ve been in both places.”

McIvor-Bennett’s latest endeavor is a restoration contest she’s holding in July with her friend, Terrill Haigler (better known in Philly as Ya Fav Trashman), where she’s offering five families the chance to have one room in their home renovated for free.

Those interested in entering can follow McIvor-Bennett (@rosebudsinvestments) and Haigler (@_yafavtrashman) on Instagram for more details, or email the reason why they’d like a room renovated to

McIvor-Bennett said she’d like to focus on rooms that bring families together, like dining rooms, living rooms, and playrooms.

“Many people don’t have a place to gather in their homes, and when kids go outside right now, they have nothing to look forward to but trouble,” she said. “I felt like if I could lift the burden of a family, I could create a peaceful atmosphere. That’s my idea of changing the environment.”

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