We recently connected with Dr. Jamisa McIvor-Bennett and have shared our conversation below.

Dr. Jamisa, looking forward to hearing all of your stories today. Let’s start with the story of your mission. What should we know?

At the heart of our mission is transformation—both personal and generational.
Rosebud’s Investments was founded on a simple but powerful belief: wealth shouldn’t be reserved for the privileged few. As someone who came from humble beginnings and became a first-generation millionaire through real estate, I experienced firsthand the power of ownership, education, and strategic action. But more importantly, I saw the gaps—so many people, especially in underserved communities, lacked access to the knowledge and tools needed to build sustainable wealth.

Our mission is to democratize real estate investing and financial literacy, making it possible for everyday individuals—even those with limited means—to own assets, build legacies, and change the trajectory of their families. What makes this mission deeply personal is that I didn’t read about this in a book—I lived it. I’ve walked the path of uncertainty, faced systemic barriers, and still found a way to thrive. That journey fuels my commitment to creating systems and programs that simplify the process, remove intimidation, and make wealth-building a reality for the people who need it most.

This work isn’t just business for me—it’s legacy work. It’s about rewriting narratives and proving that with the right access and guidance, financial freedom is not just possible, it’s repeatable.

Dr. Jamisa, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

My name is Dr. Jamisa McIvor-Bennett, and I am the Founder and CEO of Rosebud’s Investments, a wealth-building firm rooted in real estate, financial education, and generational legacy. I’m a mother, a wife, a community advocate, and a first-generation millionaire who built a multi-million-dollar real estate portfolio—including 33 debt-free properties and a hotel—by the age of 30. But more than titles or accolades, I’m someone who has lived the transformation I now help others create.

I got into this industry through a deeply personal journey. I was handed a deed to a property almost by accident—something most people might overlook. But I saw opportunity. I didn’t have a background in finance. I wasn’t born into wealth. What I did have was vision, a willingness to learn, and the courage to take action. I taught myself how to navigate the real estate system, auction space, and legal processes, and I learned how to multiply one property into a life-changing portfolio.

That experience changed everything—and it birthed my mission. I realized if I could do it, others could too. They just needed access, strategy, and support. That’s where Rosebud’s Investments was born.

We provide a range of services that meet people where they are:

Real Estate Investment Education: We teach everyday people how to acquire properties for 90% below market value, even with limited resources.

Mentorship Programs: We walk clients through building their portfolios step-by-step, from first-time investors to experienced developers.
Financial Literacy Workshops: We work with schools, universities, organizations, and even the NBA to teach wealth principles in practical, relatable ways.

Transitional Housing: Our hotel and properties serve a higher purpose—we use them to house foster care alumni, offering stability, job placement, and life coaching.
Legacy Planning: We show families how to move from surviving to thriving, using trust-building, estate planning, and deed education.

What sets us apart is that we’re not just transactional—we’re transformational. I don’t just teach theory. I teach from lived experience. Every blueprint I share has been personally tested and refined. Our clients aren’t just numbers—they’re part of a movement. We’re flipping the script on what wealth looks like, who has access to it, and how fast it can be built when done strategically.

I’m most proud of the impact. I’ve seen grandmothers buy their first investment property. I’ve watched young adults go from living paycheck to paycheck to owning multiple homes. I’ve helped families break cycles of poverty and rewrite their financial legacies—and that’s the real reward.

If there’s one thing I want readers to take away, it’s this: wealth is not out of reach. It’s often just out of rhythm. And my job, my passion, is helping you find that rhythm, own your power, and build something that lasts for generations.

How’d you build such a strong reputation within your market?

My reputation was built on three core pillars: authenticity, results, and impact. In an industry often clouded by gimmicks and gatekeeping, I chose a different route—transparency and transformation.

What helped me stand out was that I didn’t position myself as a guru. I showed up as a woman who had done the work, made the mistakes, learned the systems, and figured out how to succeed in a space I wasn’t initially invited into. I shared my journey openly—both the wins and the lessons—and people resonated with that realness. They didn’t just see the polished result; they saw the process, and that built trust.

Consistency played a major role too. I’ve always been committed to showing up for my clients, communities, and students—not just during the exciting launch moments, but through the challenges, the slow seasons, and the behind-the-scenes work that nobody claps for. Over time, that kind of integrity builds a solid foundation that people can count on.

Also, I wasn’t afraid to give value away. Whether it was teaching people how to acquire properties for pennies on the dollar, helping single moms understand generational wealth, or creating programs for youth aging out of foster care—everything I’ve built has been mission-forward and impact-centered. And people remember how you make them feel, especially when you empower them to win.

In short, my reputation came from walking the walk, lifting others as I climb, and staying deeply rooted in purpose. When you lead with intention and serve with excellence, the reputation takes care of itself.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One major lesson I had to unlearn was that success had to look a certain way—or come from certain people.

Early in my journey, I believed that in order to be respected or taken seriously in business, I had to follow a traditional path: degrees from certain schools, partnerships with “established” institutions, speaking a certain way, dressing a certain way, moving a certain way. I thought credibility came from fitting into an existing mold. But the truth is, that mold wasn’t made for someone like me—young, Black, woman, mother, first-generation everything. And trying to fit into it almost made me shrink my brilliance just to be accepted.

The backstory? I once sat in a meeting with seasoned investors who were clearly doubting my knowledge—questioning my numbers, double-checking my documents, not realizing I owned more properties than everyone at the table combined. That moment taught me something deep: validation isn’t something I need to seek when I am the value.

So I unlearned the need for external permission. I let go of the pressure to present myself as “palatable” or “professional” in a way that diluted my truth. I leaned into what made me different—and that’s what made me powerful. Today, I lead with authenticity, I wear what I want, I speak in my voice, and I let my results speak louder than anything else.

Unlearning that old mindset set me free—and it also gave others permission to show up fully as themselves too.

“You don’t have to look like the standard to set the new one.”

Contact Info:

• Website: https://rosebudsinvestments.com/
• Instagram: https://www.instagram.com/rosebudsinvestments/?hl=en
• Facebook: https://m.facebook.com/rosebudsinvestmentsllc/
• Linkedin: https://www.linkedin.com/in/dr-jamisa-bennett-mba-phd-738275173
• Youtube: https://www.youtube.com/channel/UCXBHSVt3hU-L8xFvqZjlpqg