Why Most Investors Stay Stuck at 4 Properties

In this conversation, I sit down with business consultant and investor Megan Hubner to unpack what it really takes to run your real estate portfolio like a business. Megan shares how investors can scale sustainably — from managing bottlenecks and delegating effectively to building systems that create freedom instead of chaos. Whether you own one property or a hundred, this discussion will help you think like a true business owner and set up the operational structure your portfolio deserves.


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Hello everyone, I’m Adrienne Green, and today I’m joined by Megan Hubner. Megan, thanks for joining me.

Yes, no problem. I’d love to be here.

So Megan, as we get started, can you give our listeners an idea of what your real estate investing looks like?

Absolutely. We live in British Columbia, Canada. We invest in British Columbia, Alberta, Saskatchewan, and even Ohio. Actually, we invest in Mexico too. So we’re definitely investing out of province without a doubt. If you know the Canadian marketplace, you’ll know that British Columbia is quite expensive and it’s not necessarily a very good place to invest anymore, unfortunately.

And so you’ve evolved along the way, even expanding into Mexico and the U.S. as well, correct?

That’s right. In Canada, we have a mix of infill development, short-term rentals, long-term rentals, and a multi-family portfolio. In Ohio and Mexico, we’ve done some flips.

And in addition to your own investing, you also work with investors and help them as well.

That’s right. I work as a business consultant, helping real estate investors understand how to run their portfolios as businesses.

Which I love. So let’s dive into some of that wisdom and get that right into our listeners’ ears as soon as we can. You’ve worked with a wide range of businesses before coming into the investing space. What is one key system or mindset shift that you think real estate investors really must adopt in order to scale successfully?

I think it’s going to come up a lot in our conversation today, and that is really understanding: if you have one property, you have a business. You do not need a dozen properties or multifamily developments to be running a business. The moment you buy your first property, you’re running an active business. Shifting your mindset to realize, “I’m a business operator now,” is huge. You’re not just doing this on the side of your desk or as a weekend warrior. You really do have a business. And this is one of the areas I feel very passionate about because I see investors fall down here so often.

That’s such a good point, because we see it all the time. People say, “I’m not there yet.” And that can tie into feeling not good enough or not experienced enough. It’s crazy.

Yeah, absolutely. And I think that when you make that dive into real estate, unlike other businesses — I’ve worked in multiple industries, my background is in medical and pharmaceutical sales — businesses usually grow steadily and predictably. But real estate grows incredibly fast, and we don’t see that anywhere else.

I have clients buying a hundred doors in a year. Their business just explodes. And when you don’t have those business fundamentals in place, that’s where people really get stung.

That’s a really good point. Real estate can grow so fast, so we need to take it seriously and run it like a business from property door number one. Love that. So continuing with the idea that real estate investing can grow so much, what are some of the common operational bottlenecks that you see when these real estate investor businesses try to grow? How is that showing up?

It shows up in bottlenecks — and the biggest one is bookkeeping. The finances are usually a bottleneck for everyone. And in return, that ends up being the operator — you — because you don’t have every skill set. You might be really good at analyzing numbers, or you might be really good at choosing finishes, but maybe you’re not strong in bookkeeping.

The way I usually explain it is: if you walk into any large corporation, you’ll see a table of accounting and finance, a table of HR professionals, a table of sales, and another of marketing. Each has different people because they have completely different strengths. But as a small business operator, you wear every hat. You have to determine where your strengths are, where your weaknesses are, and then understand where to hire out — so you don’t become the bottleneck in every area.

There is so much wisdom in that. First, I’d say yes — 99% of investors, if they don’t have a bookkeeper or a VA doing their books, I could bet money they’re behind on bookkeeping. Then they don’t have up-to-date finances to make informed decisions.

And second, I love that you hit on personality. When I help people hire virtual assistants, I always stress the importance of matching the right personality fit for both the job and the investor. Can you speak more to what investors need to know about roles and personality?

Yeah, I think it’s important to understand where your strengths and weaknesses are first. Then look at what buckets those fall into — what’s not you, and what you should hire out. I also think there’s great value in using personality profiling — whether that’s DISC, Human Design, or something similar — so you really understand your own personality type, how you lead, and how you interact with your team.

When you have an employee who keeps falling short in a specific area, is it because of their actual personality profile and maybe it’s not the right fit? Or have you not trained them in the way they learn best? Understanding that difference is key.

Such a great point, and I love how you share that it doesn’t really matter which tool you use — what matters is consistency and understanding. For me, I know the DISC well, so that’s what I lean on. But it’s not about the test — it’s about using it to lead better.

Yeah, absolutely.

Now, while we’re talking about frameworks, as you help investors navigate their growth, what is your go-to framework for helping them scale without burning out or losing control?

It’s a great question. The number one thing I want everyone to do is segment their business into four buckets: operations, HR, sales and marketing, and accounting and finance.

When we start viewing our business that way, we can see where our time and energy go. For example, maybe Friday afternoons aren’t great for bookkeeping — maybe that’s your creative time, so you focus on marketing then.

You want to build a weekly rhythm — bucketing tasks into those categories. Start by understanding your finances: how much money you’re making, how much your properties cost, and how much you can invest back into sales or marketing. Then look at who’s helping you — that’s HR, even if it’s just you and a VA. And finally, look at your operations: what can you automate or delegate to take weight off your plate?

I love that I’m hearing structure, systems, and time blocking — all my favorite things.

Definitely some time blocking. Yeah, it has to be.

Alright, so we’ve got this vision of these buckets. The next question I think is related. For the investors who feel like they’re doing it all, what would you recommend as the first system or process they should build to start freeing up time and improving their efficiency?

The first thing is bookkeeping — getting your accounting and bookkeeping organized. If you don’t have help and you’re drowning, figure that out first.

The second thing you’ll likely do is hire a virtual assistant to help with all the other things you may not excel at. Now, a lot of people come in and say, “I’m going to hire a VA and my life will be easy.” But when the VA arrives and asks, “What should I do?” the investor says, “All the VA things.” And that’s where the disconnect happens.

You have to prepare before bringing on a staff member — even a fractional one. Know what you’re doing, so you can stay focused on high-value tasks and delegate the lower-value ones. Those lower-value tasks become the job description for the VA.

The next step is building your standard operating procedures (SOPs). If you’re the one doing the work, start documenting how it’s done — even simple steps like, “Log into this bank account, pay this bill with this card.” If you’re not doing the work and your VA is, have them write it. Or use ChatGPT to draft one. Most people don’t build SOPs because they don’t know how to start — but you can generate a framework in 20 minutes and edit from there.

Yes, and I love that because so many people have this block with SOPs. ChatGPT can help you get started — and it’s okay if your first one isn’t perfect. It gets you moving.

Exactly. They’re all working documents.

Let’s talk about when you work with investors. Is there a system that you find is often overlooked — something they don’t value enough but that’s actually really impactful for either their profitability or their time freedom?

I think the number one overlooked system is property management software. Not enough people are using tools like Buildium or TurboTenant. Some investors outsource management, which is great, but for those who self-manage, these platforms are critical. Once you have your accounting and VA in place, the next priority should be how you manage your properties efficiently. That’s my top recommendation for anyone scaling.

Love it — the tech piece can be such a big help. Very good point. Now, we’ve talked a lot about operations, which I love. Let’s shift gears a little bit and talk about client service. How can real estate investors think about optimizing their customer or client journey — whether that’s guests in their short-term rentals or tenants in their long-term rentals?

I would say: standardize wherever possible. Standardize the locks, the way you name them when you change them every year, the amount of product you put into each Airbnb. Decide once whether you’ll provide olive oil, shampoo, and body wash — or just one of those. The more you standardize, the fewer decisions you’ll need to make later.

I know operators who use the exact same coffee maker in every Airbnb they own because it simplifies everything. If it breaks, they already know where to get the replacement part. They know exactly how it works. Every repeated decision you can eliminate saves you time and mental energy.

I love that example because we actually just changed out one of our rentals. We’d had an old drip coffee maker that had lasted years, but all our other houses had a drip-and-Keurig combo. When that last one died, we finally replaced it with the same model — now every property matches. It feels so much simpler.

Exactly. And guests really do ask those questions — what kind of coffee maker, what kind of sheets. Standardization just makes those answers automatic.

Same thing with sheets and beds, right? The top question guests ask.

Yes, absolutely. Standardize sheets, standardize how you pay bills, standardize your processes. If you want to take it a step further, integrate it all into project management software — something like Monday.com or Asana. You can plug in reminders for every recurring task: descaling the coffee maker, cleaning the dryer vent, deep cleaning the property. Then you’re not relying on memory — the system tells you what to do and when.

You are absolutely speaking my language. I love how even when we talk about client experience, you always bring it back to systems.

Absolutely. It just takes away so much bandwidth. We’re all overloaded with decisions already, and every small thing we can automate or standardize helps.

Yes — I always think about the Steve Jobs principle. He wore the same black turtleneck every day to eliminate decision fatigue.

Exactly. That’s such a good example. The fewer small decisions we have to make, the more energy we have for the big ones — the ones that actually move the business forward.

So, we’ve talked a lot about systems and structure in theory. But sometimes it helps to have a real-world example. Can you share a story — maybe from one of your clients — of a business transformation that came from implementing these systems and workflows?

Definitely. I’ve seen companies experience huge improvements in income, investor relationships, and brand recognition once we put proper systems in place. But honestly, I like to work with investors early — when they have two or three properties — because it’s easier to build the foundation right from the start. When someone already has thirty-five properties, it’s much harder to repair what’s broken.

One of the biggest questions I ask every new client is, “What’s your break-even?” And it’s shocking how many don’t know. They’re not clear on the difference between their fixed costs for running their business and their fixed and variable costs for their properties. Once we calculate that, everything changes — their confidence, their profitability, and their clarity about where to focus next.

That’s such a good point. And I love metrics. You mentioned break-even — let’s talk about that. If an investor comes to you unsure where to focus, what are the top metrics or KPIs they should track?

Number one: break it down per property. Is each one performing? If not, why not? Sometimes in a large portfolio you can afford to carry an underperformer, but you should always know which ones those are.

Second: analyze your fixed versus variable costs for the business as a whole. How much does it cost to run your operations? Are you paying yourself? Do you have funds to hire?

Everything comes back to financial analysis. That’s always where we start.

Yes — and if you’re listening and feeling a little uncomfortable right now, that’s okay. Most investors struggle with this, but that’s why you hire experts like Megan to help.

Exactly. It’s completely normal to need support with this.

So, we’re in Q4 of 2025. If an investor could only focus on one thing this quarter — one system to move toward a scalable, sustainable business — what would you recommend and why?

I would say: focus on understanding your finances. Know your break-even and your fixed versus variable costs. That’s what allows you to make smart, strategic decisions for 2026.

Yes, that foundation gives you clarity for growth. Don’t go into 2026 hiring randomly if your business is in negative cash flow. Analyze every property, decide whether to hold or sell, and build from a position of strength.

Exactly. For example, if your business is losing $1,500 a month, don’t hire until you fix that. Maybe you add two more properties or restructure expenses first. Once you cover that $1,500 gap, then you’re ready to hire confidently.

So good. All right, you’ve shared so much wisdom today. Let’s wrap up with a few quick personal questions so listeners can get to know you better.

What is your go-to tool or system for managing operations?

I really like Monday.com as a project management software. I find ClickUp has slightly better task features, but both are excellent. My top two recommendations would be ClickUp or Monday.com — but only after you’ve set up a property management system like Buildium or TurboTenant.

Perfect, I love it. I’m basically Monday.com’s biggest fan — I joke that the way people root for sports teams, I root for Monday.

If you could go back, what’s one piece of advice you’d give your younger self when you were just starting your investing journey?

My gosh, I agonized over my first property. I asked everyone for advice. I remember a friend telling me, “Men buy based on finances; women buy based on emotion. If you want to buy now, follow your gut.” It was right around the 2010 Olympic Games in Vancouver, and no one knew if the market would skyrocket or crash.

I finally took the leap and bought. I held that property for five years, even when it was in negative cash flow, because I believed it would pay off — and it did. That sale gave me the leverage to buy a townhouse, which kickstarted my investing journey. I bought my first two properties within twelve months of each other and reached that point where many investors say, “Okay, I’m tapped out — what’s next?”

It wasn’t until later, when I started my consulting business, that I realized real estate investing is its own entire industry — and from there, I just kept scaling.

I love that story. And it reminded me — we haven’t even talked about the lifestyle side yet. You’ve built a location-independent life for your family. Tell us a little about that.

It’s a path I never thought I’d take. I always assumed I’d stay in corporate and climb the executive ladder. But living in British Columbia, there are limited opportunities for growth. When I reached my goal of regional sales manager, managing a multimillion-dollar territory, I realized I hadn’t set any new goals.

Then, life threw me a curveball. I had been trying to grow my family and wasn’t having success at that time. Around then, I was offered a new position — it seemed like a dream job. But during the onboarding health assessment, they found a heart murmur. Sixteen days later, I was in surgery for open-heart repair.

That experience changed everything. I let go of fear. I let go of the corporate dream and created a new vision — one centered on time freedom and family.

Now, years later, I’m living that vision. On hard days, when entrepreneurship feels clunky, I remind myself: I get to be with my kids. I’m not dropping them at daycare every day. That was worth everything.

That’s such a powerful story. And now, you don’t even live in Canada full-time anymore, right?

That’s right. We’ve been location independent for about three years. We still love Canada — we go back to ski and snowboard — but we spend part of each year abroad. Because of our real estate investments, we don’t worry about retirement or saving for our kids’ education. We’ve built that security and flexibility through real estate.

That’s incredible. And such an inspiring example of what’s possible when you build systems and play the long game.

Exactly. It’s possible for anyone. Real estate isn’t a get-rich-quick scheme — it’s a “slow and steady wins the race” strategy. And it’s beautiful to watch that compound over time.

Absolutely. Final question — what’s a book or resource that’s been pivotal in your investing journey?

The first one that really impacted me was The Big Leap by Gay Hendricks. There’s a question in there: “What would you do if you weren’t afraid?” I remember reading that and thinking, I’d learn how to make money so I could travel the world with my family. I said it out loud, even in front of my boss, and she said, “That sounds amazing.”

That book changed the way I thought about risk and possibility. Then, of course, Rich Dad Poor Dad — the classic that planted the seed years earlier. Later, books by Brandon Turner and Bob Proctor deepened both my mindset and my systems thinking.

I love that. And I love what you said about planting seeds — sometimes you read something years before it takes root.

Exactly. You may not act on it immediately, but it’s still working in your mind, preparing you for the next step.

So, Megan, you’ve shared so much value today. For those who want to connect with you, how can they do that?

I work one-on-one with clients because diving into finances can be personal. We typically work together for six months, meeting weekly to move the business forward with a strategic plan. I’m most active on Instagram — you can find me at @meganhubner — or on my website, meganhubner.com, where you can book a call.

Perfect. And for anyone listening while driving, those links are in the show notes below.

Thank you so much for joining me, Megan, and for sharing all your insights today.

Thank you so much, Adrienne.

And for those reading this — if you found value here, make sure to subscribe, leave a review, and come back next week for another powerful conversation.

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