If you’ve ever wondered whether long-distance real estate investing is possible, this episode is for you. I sat down with Wes Thompson, a past client turned friend and successful real estate investor, to discuss how he built a thriving rental portfolio in Chattanooga, Tennessee—all while living overseas in Africa. From leveraging trust and relationships to navigating the BRRRR strategy and creative financing, Wes shares his journey, mindset, and strategies that allowed him to invest with confidence despite the challenges of distance. If you’ve been hesitant about out-of-state investing, this conversation will give you the insights and motivation to take the next step.
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Hello, listeners! Thank you for joining us for another episode. Today, I’m excited to welcome Wes Thompson, a past client who has become a great friend and an amazing real estate investor with a story worth sharing. Thank you so much for being here, Wes.
I’m really happy to be here. Thank you for the invitation, Adrienne. It’s always great to catch up with you.
I appreciate that. I know you have your own journey of traveling the world, and I’d love to start at the beginning. You’re a retired military officer investing in the Chattanooga, Tennessee, area. How did you get started in real estate investing?
It really started during COVID. I was serving overseas in Africa, and with extra time on my hands, I realized I wasn’t as financially prepared for retirement as I should be. While taking long walks in Zambia, I finally listened to Rich Dad Poor Dad on audiobook, and by the time I finished, I knew I needed to learn more about investing. I started exploring different investment avenues and quickly fell in love with real estate.
So real estate investing is more than just a hobby for you?
Yes, it’s a passion. It’s much more than a side gig. Investing in real estate has introduced me to so many people, expanded my network, and provided opportunities outside of the military, which was my entire world before.
That makes total sense. Real estate connects people across distances. Speaking of distance, I think you may hold the record for the longest-distance investor—buying in Chattanooga while stationed in Africa! How did you choose Chattanooga as your market, and how did you make that work?
My wife and I always planned to relocate to Chattanooga. She grew up in East Tennessee, and all her family is between Chattanooga and Knoxville. She went to UT Chattanooga, and over the years, we’ve both fallen in love with the city. It just made sense to invest where we wanted to live long-term. My wife actually found a post in a Facebook group about investing while living outside the U.S., which led me to the REI Concierge with Tim and Lisa. That’s how I first got introduced to you and Chattanooga as our market.
I love that strategy—investing where you plan to live. Since you were in Africa, how did you get comfortable with investing sight unseen? That’s a big mental hurdle for many long-distance investors.
It was definitely a challenge at first. We had rented houses sight unseen in the military, and it didn’t always turn out well. But this was different. The key was building a trusted team. We had no choice but to find people we trusted. I knew I had control over the property, unlike a rental, so I just needed the right people. When Tim and Lisa introduced me to you, I already knew they were successful investors in Chattanooga, so if they trusted you, I did too. That trust was key, and you and your team never let me down.
That’s such an important takeaway for long-distance investors—leaning on experienced people who’ve done it before. You’ve continued to invest in Chattanooga even after moving back to the States. What has kept you in that market?
It all comes down to trust. The network of professionals I built through you is something I wouldn’t want to replicate elsewhere. I could probably get better deals in other markets, but without the right team, those deals wouldn’t be worth it. My team in Chattanooga has never let me down, and that means more than just getting a slightly better deal elsewhere.
That’s a great point. One bad experience with a contractor or property manager can erase theoretical gains. Speaking of teams, what advice do you have for investors looking to build a strong team? Have you had to replace anyone or handle conflicts?
Trusting the recommendations of successful investors is huge. When I needed a property manager, you pointed me in the right direction. The same happened with my contractor and loan officer. You wouldn’t put your name on the line for someone who hadn’t performed for you, so I knew they would take care of me the same way they took care of you. That’s how I built my team, and I still work with all of them today.
That’s incredible. Now, let’s talk about strategy. You started with BRRRR and have since shifted towards creative financing. Why the switch?
BRRRR worked well for me, but I’ve shifted towards creative finance strategies like subject-to and seller financing. The market conditions and interest rates have changed, making BRRRR less effective in some cases. But at its core, if you’re buying below market value and adding value, the strategy still works. Many people claim BRRRR is dead, but I think they’re missing the bigger picture. Real estate isn’t a short-term game. If you don’t need to refinance immediately, you can still hold and wait for better conditions.
I completely agree—real estate is about long-term thinking. Now that you’ve been investing for a while, what does your portfolio look like today?
I have five properties—one near Augusta, Georgia, and four in Chattanooga. I’ve averaged about one or two acquisitions per year. My first deal, a duplex, is still one of my best-performing properties. I’ve also done subject-to and seller-financed deals, which have been great additions. One of my favorite deals was a single-family home listed at $110K. I knew it was undervalued, so I offered $115K to secure it. After inspection, I renegotiated to $90K due to necessary repairs. That property appraised at $108K at closing and is now worth nearly $200K.
That’s such a great case study. Many investors hesitate to offer above asking or negotiate post-inspection, but you handled that deal so well. What mindset helped you make those decisions?
I try to stay logical rather than emotional. I see a listing as just the starting point and trust the due diligence process. I also knew I could walk away if needed, so there was no fear in making an offer or negotiating the price down. The key is having contingencies and taking a step back before making emotional decisions.
That’s a great lesson for investors at all levels. Finally, what advice would you give to military personnel looking to invest in real estate?
Use your VA loan—it’s an incredible opportunity. I’ve seen young service members buy multi-unit properties, live in one unit, and rent the others, setting themselves up for long-term wealth. The worst thing you can do is nothing. Just get started.
That’s fantastic advice. Wes, thank you so much for sharing your journey and insights. Where can people connect with you?
The best place is on Instagram: @itswestthompson. I don’t post a ton of content, but I’m happy to connect and chat.
Perfect! Thank you, Wes, and thank you to our listeners. If you’re considering investing in Chattanooga, reach out—I’d love to connect you with an amazing team.