Jamisa McIvor-Bennett


Homeownership is a secure way to build wealth. For many Americans, homeownership is an instrumental way of creating generational wealth for their families. For Jamisa McIvor-Bennett, founder and CEO of Rosebud’s Investments, her introduction to ownership began with a conversation with her grandmother, which ultimately led her to become a real estate investor at the age of 19.

After a conversation with her guardian about being next in kin to own and manage the family home, Mclvor-Bennett was added to the deed. Months later, her grandmother passed away unexpectedly.

“I took what she said to heart…to be responsible and to help my family because this [family home] is all we had. That kept replaying in my mind over and over again,” says Mclvor-Bennett.

At that time, she worked as a cashier and could not afford home renovations on her own, so she had to make an executive decision.

“In the back of my mind, I kept hearing my grandmother say, ‘this is all we have’, and one day I asked my myself, ‘why is this all we have?’” and that question led to her selling the house for $152,000. After doing research of her own and speaking with financial advisers, Mclvor-Bennett decided that investing her earnings into real estate would be the best way to never have to work for someone else again.


Mclvor-Bennett’s humble beginnings taught her how to be conservative with money and wise in her dealings.

“During that journey, I ran into a guy who was a real estate investor. That was my first time making the differentiation between an investor and a little estate agent,” says Mclvor-Bennett.

Under the tutelage of her mentor’s guidance, she went on to purchase her first home for $6,500 in cash. And she didn’t stop there.

Now 26, McIvor-Bennett is the owner of 18 properties throughout Pennsylvania—and she only has one mortgage. In addition to owning and investing in properties, she also teaches others looking to generate more income and learn the ins and outs about real estate and real estate investing.

Her company, Rosebud’s Investments, caters to people interested in real estate investment but unsure of where and how to get started. The company offers individualized services in investor processes, for both new and seasoned investors who are looking to enhance their knowledge and expertise. Beginning with their individualized investment call, new clients work with a member of the Rosebud’s Investments team to create a blueprint for purchasing property without using credit.


Like many business owners and investors, Mclvor-Bennett has been met with challenges. After purchasing nine properties, she began to hit a wall.

“I was down to $15,000 and some of my properties needed to be rehabbed. I wasn’t educated on the loan process. And keep in mind, I didn’t even have credit cards. These are all things that I had to pretty much learn as I went along. But I do remember playing monopoly as a child—so, I decided I was going to sell a house.”

After selling a few of her properties, she learned more about the business through that process. As a first-generation real estate investor and entrepreneur, Mclvor-Bennett knew that she had to seek the formal training to educate herself so that she could grow her business after buying her properties in cash.

“It was helpful to me to learn the terminology and more about contracts.”