What if the chaos in your real estate investing business isn’t a sign of failure but a signal you’re on the brink of something big? In this blog post, I share how I turned my own portfolio’s operational mess into a streamlined, scalable system. I’ll walk you through the challenges I faced, the practical steps I took to overcome them, and my top tips for building systems that allow you to scale without multiplying the work. If you’ve ever felt stuck or overwhelmed in your investing journey, this is the guide you need to turn things around and achieve the freedom you’re working toward.
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What if the chaos in your real estate investing business isn’t a sign of failure, but a sign that you’re on the verge of something big?
Today, I’m going to walk you through a real-life case study—my own—on how I turned some chaos in terms of my real estate investing portfolio and how it was organized and tracked into clarity, and that helped me scale my portfolio successfully from there on. And I want you to stick around until the end for my number one tip to ensure scaling doesn’t add more work to your plate but instead helps you achieve the freedom that’s the reason you got into real estate investing in the first place.
When my real estate investing portfolio started growing and I wanted to manage it well so that I was really knowing what was going on and I had the data to make smart decisions, it felt like chaos. It felt like I didn’t have the data and the numbers I needed to have, and like my husband and I were constantly juggling every task with our short-term rentals. We were putting out fires. We had a virtual assistant helping, but they really weren’t the right fit, and we didn’t have everything organized and systemized to empower them to do their job well. Everything was scattered, chaotic, and stressful. Nothing was documented, and I felt stuck.
We didn’t want to grow this investment portfolio when it felt like a lot of work and like we were constantly stuck in the weeds. Does this sound familiar to you? I think a lot of investors struggle with this challenge, right? We just take advantage of opportunities when they come, we buy properties, and then we’re like, “My gosh, we didn’t make the systems, and it’s a mess.” I get it.
What I’m going to share today isn’t just theory; it’s the step-by-step process I used to transform my real estate investing business into a streamlined, scalable operation where I can easily have a virtual assistant do a lot of the work and know that it’s being done well. And if I can do this from the mess that I had, I know you can too. So let’s dive into what I did and what lessons learned there are for you and your portfolio.
When I first started fixing the chaos and the mess, one of the first challenges I had was all these operational details. I had long-term rentals, and short-term rentals, and they were in a couple of different cities. Everything just seemed like when an issue popped up, it was a fire. We didn’t have smooth systems and operations to handle repeat tasks again and again, where a virtual assistant could handle those repeat tasks. Instead, things kept dragging me into emergencies, and I thought, “This does not need to happen, right?” These things happen again and again. There is a way we can systemize, organize, and proceduralize this so that I’m only dealing with the rare, first-time occurrences.
The thing is, when you don’t have these systems in place, scaling just multiplies the chaos. You’re bringing in new cities, and new properties, and you don’t have systems to handle what you already have or easily adapt to new things. It just makes more chaos and work. That’s why I’m a huge advocate for getting organized and systematized so you can use a virtual assistant, leverage technology, and focus on your top tasks while the operational stuff is handled.
Think about your own real estate investing business. Where do you feel like things are slipping through the cracks? Where do you have operational chaos you’d love to fix? I’d love to hear your thoughts in the comments.
Like many investors, I scaled without clear workflows or preparation because when opportunities arise, you want to jump on them, right? I thought I could just hustle harder—work more and get everything handled. But that approach isn’t sustainable. It doesn’t lead to the life we want as real estate investors. It keeps you busy with work that doesn’t help you grow your portfolio smartly. I’ve been there, and I’ve learned there’s a better way, which I’m excited to share with you.
Here’s what I did to turn it around. I started small, focusing on organizing a few simple tasks to get easy wins. I didn’t stress about organizing my entire portfolio at once. Instead, I asked, “What’s one thing I can systemize and make easier?” For me, that was accounting and bookkeeping. We already had some systems in place, so it was easy to clean them up and make them perfect.
I scheduled meetings with my virtual assistant, who’s also our bookkeeper. We walked through the procedure, made notes, and improved the process so he could run it on his own. I love using Monday as a task management system. Every repeat or one-off task is created on Monday and linked to a Google Doc procedure. We already had some of these procedures, but they weren’t linked or consistent, so it was messy.
I took what we had, guided my virtual assistant, and let him do the work. That’s the beauty of having a virtual assistant—I do 20% of the work, and they’re empowered to do the other 80%.
After that, I tackled guest messages because they were a headache. During that process, I realized our technology wasn’t helping us. For our short-term rentals, I switched to Hospitable, which solved a lot of issues. My virtual assistant researched options and brought the top two to me, and I made the final decision. We systematically moved from one system to another until everything had procedures and repeatable tasks that a virtual assistant could handle.
The final piece of organizing my portfolio was ensuring the right people were in the right roles. Whether hiring a virtual assistant or someone local, you need the right person in the right role. It’s tough to figure out what you need and hire for it, but it’s essential for scaling.
My top tip? Start small and grow from there. Treat scaling like building a foundation. Don’t get overwhelmed by the idea of being at level 10 from day one. Focus on organizing one piece of your portfolio, and let those small wins build momentum. That confidence will help you scale smarter and faster.
I get it—if your portfolio feels messy, it can seem impossible to scale without doubling your workload. But with systems, procedures, and leveraging virtual assistants and technology, scaling becomes manageable and even exciting. Let’s make it happen!