What happens when you die without a will? What happens to your assets if there isn’t any money to maintain them? Essentially, what happens if you die without a succession plan?

That’s what my friend Caitlin is here to talk about today. The Stories of Success podcast was originally designed for investors to show you what they’re doing in 2026 and how they got started. But not all investors got started because they decided to. Some got started because of an inheritance. No prior knowledge, no funds, no plan.

That’s what happened to Caitlin. She fought through that and continues to push her story forward. Today,. You’ll learn the importance of both building wealth for future generations and protecting it. This episode is titled Everyone Thinks They Have More Time with Caitlin Walls. I hope you enjoy.

As you know, Caleb is not involved in this company at all. I mean, barely shows up to work, barely contributes at all. So it’s probably news to you, but he’s also a real estate investor! He’s had his own rental properties. Unfortunately none of those soft skills transferred to this job — but hey, we can dream.

All jokes aside, I asked Caleb to do this interview because I wanted to show you a perspective of what actively investing while you’re still working could look like. And I would have to check, but I think this is also one of the first few investors that is talking about investing as a couple, and not just as an individual who may or may not be married.

And I guess I also wanted you to see how skills you can pick up five, ten, twenty years in the past can come back to benefit you in the future.

This is an interview with one of my dear friends and a huge part of the Simple Real Estate team, Caleb Taylor. I hope you enjoy!

Now a lot of y'all know, I started investing because I didn't have any money. So I asked Rick for this interview to give you a completely different perspective.

This is my friend, BIG MONEY RICK, a lawyer from D.C. who on the outside looking in has got everything (the money, the job, the security, etc.). But even Rick was able to look around and realize nothing is as secure as one might think.

This is Rick's story of how he transitioned a well paying job into a long term journey to set up investments and additional income that can his support his family regardless of his employment.

This episode is titled "Under the Umbrella of Your Own Control" with Rick Oleka. I hope you enjoy!

Investing doesn’t always go to plan, especially when family is involved. So how do you balance the financial responsibility of being a property owner with the emotional and perhaps even traditional aspects of helping your family members? I admit, this is somewhere I struggle so I’m grateful for people like Mamoudou who are honest and forthright about their journey to do something I think so many of us want to do.

This is a story about buying property for your family. How to balance the benefits of ownership with the desire to support your people. This is the Duty of Family with Mamoudou Keita. I hope you enjoy!

Another member, another deep dive into investing success! Amanda Vyfuis is a member of the Simple Real Estate Membership, like Rory and

Minnae and Elesyia and I invited her one, because like them, she is OUT HERE DOING THE WORK.

Amanda originally came to the membership because she wanted to transition more into multifamily properties in order to pay for her babies college tuition! Are you listening? She recognized at birth, she couldn’t save enough to pay for their tuition in 20 years and took matters into her own hands. Initially, I was fully onboard with the multifamily plan! Remember, that’s my whole schtick. BUT it’s based on the research I’ve found in MY MARKETS. This interview is how we used that same process and found a different answer with Amanda as we planned for the long term.

This is “Don’t Be In A Rush” with Amanda Vyfhuis.

How much do you believe in yourself to just figure it out? I mean you can see the opportunity, you can identify the benefits. But you are fully aware you don’t have the skillset on day one to achieve that goal. How much can you sit with that discomfort of both being responsible for the outcome and unsure of how to get the task done?

I would argue that’s what makes Rory so successful. When he sees opportunities, he doesn’t think, “what’s everything I need to finish the plan?” His focus is, what do I need to get started. No reason to let step 10 keep me out of the game. That will come in due time. Step one is what gets me in the ring. I want you to hear from another black investor, in another big expensive city finding the same purpose and profit I’ve found in rural America. It can be done.

This is Rory Boone, a member of the Simple Real Estate Membership based in Seattle Washington. I can’t wait to hear what you think.

The last two podcast interviews we posted were about New York City investors. Showcasing how black investors are thriving even in large cities. But I feel like on my page the east coast gets a lot of love and attention (which makes sense, it’s where I’m from), but are black investors doing big things on the west coast in big cities? Absolutely they are.

The next two interviews are about west coast investors going above and beyond in Seattle, one of the biggest markets on that side of the country. Today’s interview is with one of my dear friends Ashley, a familiar face to a number of y’all. She’s been a speaker at my conferences, she’s a part of my traveling mastermind. And Ashley is here to talk to you all about DEVELOPMENT. How do you go from dirt, literal soil, to a multifamily complex? Not just having the dream but a full overview of concept to reality (along with some exit strategies and boutique business ideas).

This Ashley Gallagher going from dirt to development. Enjoy our continued black history month series!

How many of you are willing to follow your dreams? And by dreams, I truly mean the dreams you have when you’re asleep and your mind wanders and you hatch a plan unlike any other you’ve had. That’s what happened with Ms Wanda.

She dedicated more than a decade of her life to a dream she had. A dream where she owned a piece of Harlem, and then used that home to invest across the country.

This episode is titled “A Dream Come True” with Wanda Richardson. I can’t wait to hear what you think!

Long time listeners of the podcast have heard Ms Regina before and she was such a hit I asked her back to share once again.

Now I’ve heard these stories over and over but I leave with something new every time. Truly. And this time it was how we’re each affected by someone else’s vision.

Someone other than you has put a lot of thought into what you should be doing and how you should be investing and where you should be living and how you should be spending. Maybe it’s your parents. Maybe it’s your government.

And Ms Regina’s take, is that you get to decide who you want to align with. You get to choose which options work best for you and what you decide, the vision you choose to follow is what your future success will be based off of.

This episode is titled “The Benefits of Another’s Vision” with Regina Watson. I hope you enjoy.