Deandra McDonald
Stories of Success
The success stories of real estate investors with Deandra McDonald.
Author
Deandra McDonald
Category
Podcast website
Latest episode
May 8, 2026
Where to listen?
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Episodes
Be Where Your People Are (with Nasif Ahmed) 08.05.2026 37:46
Now my husband and I almost moved to be closer to Nasif. Back in 2024, when my husband was looking for new jobs, Baltimore was a strong contender because of Nasif and his unwavering emphasis on building his community. It’s not necessarily a surprise with his strong Bangladeshi background that he was raised with a high value on loving his people. I expected to see it in his actions, but was surpris...
I Just Wanted a Dog (with Sarah Sher) 01.05.2026 29:12
Why should you buy a house? Why should you prioritize shifting from a renter to a homeowner? For financial security? Long term stability? Space? Amenities? Custom? Today’s interview is with Sarah Sher — a long time friend of mine and another native New Yorker who was raised to see homeownership and investing a little differently than we currently do. This is “I Just Wanted a Dog” with Sarah Sher o...
Your Dreams Deserve Your Reflection 30.04.2026 20:14
This is a bit of a transition week. We are preparing to celebrate AAPI Heritage month and I didn't have an additional guest lined up for this episode. So instead I personally took some time for reflection. Can't wait to see you guys back next week!
Everyone Thinks They Have More Time (w/ Caitlin Walls) 10.04.2026 46:47
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 star...
Falling Into Househacking: From 3 Houses to $400k (w/ Caleb Taylor) 03.04.2026 36:05
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 persp...
Under the Umbrella of Your Own Control (w/ Rick Oleka) 27.03.2026 33:02
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. Thi...
The Duty of Family (w/ Mamoudou Keita) 25.02.2026 24:04
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 o...
Don't Be In A Rush (w/ Amanda Vfyhuis) 23.02.2026 30:13
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 listenin...
Just Take the First Step (w/ Rory Boone) 19.02.2026 40:43
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...
Going From Dirt to Development (w/ Ashley Gallacher) 17.02.2026 39:13
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...
A Dream Come True (w/ Wanda Richardson) 16.02.2026 26:14
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...
The Benefits of Another's Vision (w/ Regina Watson) 14.02.2026 39:18
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 an...
From Habitat to Homeownership (w/ Elesyia Outlaw-Evans) 12.02.2026 30:10
Children of homeowners are more than twice as likely to own a home themselves. That’s less than a 10% chance for you to be an investor if your parents rented all of their lives. So when Elesyia saw her mother FIGHTING to be a homeowner, she knew had to pay attention. Now things are a little different. Mom’s a homeowner. Elesyia is an investor and now her daughter talks about rentals. Three generat...
I'm Not An Investor (w/ Jameel Dennis) 09.02.2026 34:38
I’ve known Jameel since before I was a teacher. He was a chemist who transitioned into teaching, so he was the perfect match to mentor me - a chemist transitioning into teaching. That’s why I was so proud to help HIM transition into an investor. I mean he’s been listening to me ramble about the benefits of investing before I had even purchased my first house. Now with this interview you get to see...
Surrounded By Depreciating Assets (w/ Tamara Dias) 09.02.2026 36:48
If you don’t want to hear about yourself, don’t call Tamara. If you’re not ready to run the race with greats, let me tell you don’t call Tamara. Because Tamara knows what she wants, and puts in the work. For her it’s that simple. Investment isn’t about generating SOMETHING, it’s about generating the ONE thing she’s looking for. Today’s interview is a different spin on the whole concept of investin...
The Luxury of Fear (w/ Jazmyne Butler-Boothe) 05.02.2026 23:35
When I think class, when I think consumer experience, when I think intention hosting, I think Jazmyne. This story is a unique one for the series as we’re shifting out of long term rentals into a more short term, customer facing real estate investment. Long term multifamily is fantastic (y’all know that’s my bread and butter), but it is far from the ONLY way to generate income in this field. This i...
Receiving Generational Wealth (w/ Minnae Chabwera) 03.02.2026 25:46
When househacking is all the rage, how do you invest if you love your home, love your neighborhood, and have no desire to move year after year? That’s how Minnae came to the Simple Real Estate Membership. She owned her home and enjoyed her lifestyle, but was unsure of how to align her day to day with the long term investing goals she had. Today you’ll hear one of the strategies we came up with and...
The Luxury of Information (w/ Kendra Barnes) 03.02.2026 27:10
Today we speak with Kendra Barnes, a dear friend of mine who was the first to show me that early retirement was an option. I didn’t realize there were women like me who had truly opted out of the traditional workforce. No kids. No disability. No second career option. Just desire. And I latched on to that HARD. In this episode Kendra will share her experiences, including the challenges and mistakes...
Love of Labor, 5: I Don’t Know What To Do About Trump 25.08.2025 22:09
I remember being so angry right after the election, and it would be easy to say it was because of the overall result. It would be easy to say it was only because of the policies and rhetoric. That was a part of it for sure, but a larger part, a more gut wrenching part, was learning that the community around me, people I thought I knew personally and intimately, happily and eagerly voted for Trump....
Love of Labor, 1: When Identities Collide 04.08.2025 20:34
"I am not trying to curate something for you to see. I am trying to make something I feel called to create." I am trying to develop a better process to help me work through moments where I feel like my values are being challenged. And challenged might be too tame a word. Maybe colliding? Does that make sense? Sometimes I feel like my identities are colliding and I don't know how best to sort throu...
Love of Labor, 4: I Don't Know What I Sound Like 04.08.2025 17:10
This episode is about identity. How much of who I am is an active choice? Am I making intentional decisions or just regurgitating what I've been taught over the last 30 years? I don't want to look up and regret the way I've lived my life (or even worse be apathetic). I want to fully live through every experience, but that means confronting some of the long held beliefs I have about the best way to...
Love of Labor, 3: How Did I Keep The Faith To Accomplish My Goals 04.08.2025 24:49
Is there a difference between keeping your faith and just outright refusing to accept any other reality? This was a question submitted by one of our neighbors in the community. I know it's not perfectly in line with what I said we'd talk about last week. But the question was so good I felt I had to pivot!
Love of Labor, 2: Why I Created the CLIP Method 04.08.2025 21:46
I am trying to develop a better process to help me work through moments where I feel like my values are being challenged. And honestly, challenged might be too tame a word. Maybe colliding? I can feel my identities colliding and I want to develop a more consistent process to work through that. Hypocrisy is a big trigger for me. I don't want inconsistencies with how I live my life and how I interac...
Love of Labor, Intro: To Dream About Labor 04.08.2025 4:55
"I don't have a dream job because I don't dream of labor." I am at this junction of my life where I am clearly seeing how my values and training are clashing in real time. I was trained to invest my way out of the proverbial rat race. I was taught to invest and run businesses and generate profit. Then rinse and repeat and rinse and repeat and rinse and repeat. What I wasn't taught is how I could (...
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