Cindy West’s journey from Army veteran to corporate attorney to full-time real estate investor is nothing short of inspiring. After realizing the corporate world wasn’t for her, she pivoted to real estate, starting with wholesaling and quickly shifting to fix-and-flips and rental properties. In less than two years, she built a portfolio of 28 doors and left her W-2 job behind. In this conversation, Cindy shares the highs and lows of her journey, the lessons she learned managing renovations, and the strategic moves that allowed her to scale quickly. If you’re looking for practical insights on real estate investing, self-managing properties, and maximizing cash flow, Cindy’s story is packed with valuable takeaways.
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Hello, everyone! Today I have with me an amazing guest. I’m very excited for her to share her story—how she’s gone from being an Army veteran to a full-time attorney and now a full-time real estate investor. I have with me my friend and amazing investor, Cindy West. Cindy, thank you so much for being with me today.
Adrian, thank you so much for having me. I’m really excited to be here and to share my story.
And you have such a great story. I know there’s going to be so much wisdom for our listeners in hearing and learning from where you have been. I teased your background a little bit there, but why don’t you walk us through your journey? Tell us about how you were brought up, what you were doing initially, and how you got into real estate investing.
Absolutely. A little bit about me—I am from South Florida. I grew up in a very poor household. My mom was a single mom. She was undocumented and cleaned houses our entire life. The good thing about that experience was that she actually cleaned homes for very wealthy people. Although I didn’t have much at home, I always saw a lot and really grew up very ambitious and wanting a lot out of life.
By the time I was 18 years old, I read Rich Dad, Poor Dad like a lot of people do, and I was inspired. I thought, “Real estate is the way that I can get out of the circumstances I’m in.” So I took the real estate exam, but I actually failed it. That kind of went out the door for me, and I figured being an agent wasn’t the right route. Ultimately, I went to the military, then to college. At 25 years old, during the pandemic, like a lot of people, I started watching YouTube and came across wholesaling.
I became a wholesaler for about a year. Not a very good one, to be honest, because ultimately, I couldn’t sell those deals. So I bought them myself and began flipping. I became a fix-and-flipper while in law school. I did that for about a year and ultimately decided, “You know what, I’m going to put real estate on hold while I pursue law and see if this is the right thing for me.”
I started my job, worked there for about four weeks, and realized, “I hate this place. I need to get out.” So I went back to real estate at the beginning of 2023. By August of 2024, I had 28 doors. I put in my two weeks’ notice and became a full-time real estate investor. Now, I fix and flip, and I own my rentals as well.
Okay, you just dropped so many insights in that little history—so many things that are going to have people’s heads spinning. Let’s go back to when you were in law school, and wholesaling didn’t work out, so you switched to flipping. How did you balance that? Were you doing the work yourself, or were you overseeing contractors?
It was pretty challenging. I was in law school, and my flips were two hours away from Miami. Most of the time, I was in the car on a Zoom call. The one thing that really helped me was that it was the pandemic, so I was remote for school. That allowed me to be more mobile. I balanced law school in the evenings, and in the mornings, I would cold call, meet with contractors, and keep my flips moving. Once we returned to in-person classes, I had to make a decision—I couldn’t be in two places at once. I had to choose where to focus my attention.
That makes a lot of sense. I know that I also left the W-2 world. What made you realize that law wasn’t for you?
The legal field I was in—corporate law—is very dry and business-oriented. You don’t feel like you’re actually creating an impact. You’re not interacting with people outside of your field. I realized that my personality is to engage with others, interact regularly, and feel like I’m doing something positive in the community.
I rarely got that feeling from being a lawyer, but I do from real estate. As a landlord, I take pride in turning neighborhoods around. I am a good landlord—I’m responsive, and I love seeing people feel proud of where they live. I just didn’t get that type of pride as a corporate attorney, doing mergers and acquisitions for big private equity firms.
That’s why we connect so well! So tell us a little bit about what you’re doing now and how you ended up in your current market.
I moved from Florida to Washington, D.C., where I worked as a lawyer for about nine months. My law firm let me go remote my last year. During that time, I accumulated rentals in North Carolina and decided that once I hit 10 units, I would move there and be on the ground. That’s exactly what I did.
Now, I live in Charlotte and focus on fixing and flipping. When I left my legal job, I had rental income coming in, but I wanted more active income. I have about eight projects going on right now. My rental portfolio is sitting, generating equity and cash flow, but I focus on flipping to keep money coming in so I can continue buying rentals. That’s always my ultimate goal, but as you know, you need money to buy rentals. That’s the strategy I’ve been using.
That’s such a great insight. It’s something people don’t talk about enough—the balance between long-term rental wealth and needing active income to keep growing. Rentals are great, but they can be unpredictable. One unexpected repair can wipe out half your profit for the year.
Exactly. Some of my income comes from rentals, but they aren’t always consistent. We just went through a winter storm, and I had pipes freeze and water heaters break. That’s thousands of dollars in unexpected expenses. That’s why I needed to find a way to generate regular cash flow, and flipping was the answer.
That’s such a key lesson for investors. I love how strategic and logical you are. You’ve built something really impressive. Thank you so much for sharing your insights today. Where can people connect with you?
I’m most active on Instagram—@CindyWest_. I respond to all my messages, and I love connecting with new investors. I’m also looking to connect with developers since I want to step into that next phase of my journey.
That’s exciting! I can’t wait to see what you do next. Thanks again for joining me today!