Real estate gets a bad rep sometimes, and I think a lot of that comes from the guys with the flashy ads that sound like get-rich-quick schemes.
Some of that stuff is real, even if it isn’t common. Some people do quit their 9-to-5s and build an empire in a few short years, and more power to them. But maybe that’s not what you’re looking to do. Maybe you’re just taking the first few steps, looking to add some income and build a little wealth and flexibility on the side. Or maybe you’re skeptical of real estate (which is valid) and you just want more relatable, real life, grounded information before you decide anything.
This is the first post in a new series where I’m tapping into the wisdom of real people from this community. People with jobs, kids, commitments, who treat real estate like a side quest. I’ve been asking them how they got started, what made it doable, how they’re scaling or deciding to exit, and what they wish they’d known earlier.
I’m not trying to convince you to invest in real estate. There are risks, a learning curve, capital involved, and truly it isn’t for everybody. But hopefully across the series you get to hear a variety of perspectives from folks like you and me, and those pros and cons become more tangible.
Today we start at the very beginning (a very good place to start): how do people actually get started, and what can we learn from what they did?
Disclaimer: this is just my thought process based on what I’ve learned and what these investors shared with me. I’m not a lawyer or a financial advisor. I cannot give tax, legal, or financial advice, so please treat this as a starting point for your own research and consult an actual expert about your situation.
Who Are These People Anyway?
First, let’s meet a few of the investors I had the chance to talk with. I want to thank them for taking the time and for sharing their stories so openly.
You can find Jimmy on Instagram, and Andrew on Instagram as well. Brugh didn’t ask for any specific shoutouts, so if you’d like to get in touch with him, leave a comment and I’ll pass along the request.
Beyond these three, I also have friends and family who are nurse practitioners, tech entrepreneurs, corporate people whose jobs I can never quite remember.. and then me, a pharmacist in the hospital. All sorts of regular people you’d run into in real life, who have done some sort of real estate venture on the side.
The First Deal
What I really wanted to know was how they got into real estate at all, and what they actually did for that first investment.
It was fascinating that all three took a completely different path.
- Jimmy more or less stumbled into house hacking while trying to solve a commute problem. What started as a practical fix turned into a long-term rental: a primary front house plus a detached back structure he converted himself (registered as a den rather than a formal ADU). It functions as a duplex, so that’s how I’ll refer to it going forward.
- Brugh was the opposite, very intentional about it. He knew he wanted real estate, identified Ohio as his market, and bought a triplex. He was that aware and open-minded while he was still a student. I was definitely not there at that age.
- Andrew also went in with focused intent, but leaned on knowledge he already had about a specific area, plus his own travel experience. He bought a cabin, basically because vacation is awesome.
We’ll get into the financing and how these properties are doing, but I want to point out something I noticed about the way all three took that first step.
Regardless of their reasons, whether they picked long-term or short-term rentals, whichever door they came in through, they were all open to the possibility. They accepted the challenge of doing something they had never done before, and they all shared this outlook of knowing they could figure it out. They did their due diligence, they ran their numbers (if you want somewhere to start on that, my short-term rental calculator is free), they used every resource they could find to learn as much as possible. But all of them acknowledged, in one way or another, that there was some level of uncertainty at the start, and that it isn’t possible to know everything 100%.
They took action anyway, one step at a time.
Where the Money Came From
Jimmy financed with a low interest rate mortgage. Brugh used a DSCR loan.
Beyond financing the purchase itself, there are all the other startup costs. Appraisal, inspection, the fees that come with closing on a property, any rehab or renovation, and in the case of short-term rentals, furnishing. Then licensing and any business or legal filings on top of that.
These are things you can plan for, and ideally they’re something you factor in during your analysis stage. They really add up though.
That’s also why I’d get your business banking and bookkeeping sorted early, before things get messy. Keeping personal and rental finances separate from the very first property makes everything easier later, especially at tax time. Here’s the setup I use for that.
How It’s Going
Andrew is doing really well with his Airbnb listing. After that first success he’s planning to move into a new home and turn his current primary residence into a short-term rental, and he had some great advice about designing a property around the type of guest you’re expecting to host.
I appreciated how grounded he was about whether or not to scale. I share some of those same thoughts. Obviously it depends on your goals, but there are real trade-offs to scaling, especially with something as hands-on as this.
Jimmy has found the long-term rental of his first property to be a great investment in an area with high rental demand. Since then he’s done a live-in flip with a giant rehab project, and he’s onto a third thing: rental arbitrage on a beachside condo his girlfriend vacated when she moved in with him. He considered running it as a short-term rental, but the approval process looked a bit tricky. He’s thinking about adding more in the future, mostly for the equity build.
Honestly, that sounds great to me too.
Brugh had just closed on his first property when we talked, so we’ll have to check back in on him. So far he’s approaching everything with such a positive attitude, he’s already learned a lot, and he has some big long-term goals.
How Did They Know They Could?
The last thing I wanted to know was how they knew they could do this at all. What kept them moving forward, and what they’d tell someone at the very beginning.
- Jimmy pointed to house hacking, and the natural progression from there.
- Andrew leaned on background knowledge, then backed it up with numbers.
- Brugh asked a lot of questions and stayed resourceful.
Five Takeaways
If you’re just starting out, or just weighing up whether real estate is the right move for you, here’s what I took from their stories, both from what they said and from what I noticed.
- There is not one path
You could start with a nearby-ish short-term rental. You could house hack. You could go straight to an out-of-state triplex, or in my case, test the waters with a backyard ADU. There’s no one speed for scaling, and no single end goal where everyone upgrades the four little green houses into a big red hotel.
I find that comforting. If you choose to make real estate part of your personal finance journey, you can really customize it to your own goals and risk tolerance and preferences. There will always be people scaling incredibly fast, and those stories get more attention because it’s more fun to click a thumbnail with a dramatic result. Don’t let that distract you, or diminish what you’ve accomplished.
- They leaned toward action
Yes, they all ran their numbers and did their analysis. Then they did something about it.
When I asked how they actually pulled the trigger, where the confidence came from, they all kind of paused, thought about it, and gave some logical answer. I knew I’d be a good host. House hacking is generally considered easier. I had a good team. All of those things help.
But ultimately, for them and for me, there wasn’t some magical checkbox that once completed clears you to take action. You kind of just have to decide to do something.
I think that’s particularly hard if you have perfectionistic tendencies. What if I didn’t consider every possibility before acting? If that’s you, see if you can lower your threshold for getting started to “good enough,” knowing your perfectionism doesn’t end there. You’re going to keep improving and course correcting the whole time, and you’re going to be fine. That, or find a partner who leans toward action.
I may or may not be speaking from personal experience.
- They didn’t know all the answers, and they knew it
Nobody came off as confidently incorrect. They were aware of the gaps.
They were also resourceful about it. They reached out for help, they asked questions, they weren’t afraid to look silly. There was this optimistic belief that they could figure it out, paired with the pragmatic follow-through of actually figuring it out.
- Nobody said zero money down
This is something they didn’t say, which stood out to me. Different loans, different structures, but not one of them did this with no money at all. Every single one of them had to spend something, whether that was inspection fees or a renovation project.
I know there are examples of people using creative strategies. Realistically though, I’d think of real estate as involving some level of upfront capital. Personally, and this is not financial advice, if I truly had $0 to start with, I might look at other investments first.
- You’re not crazy for thinking real estate wasn’t for you
This is the big one. If you’ve been finding real estate daunting, or somehow “not for you” based on who you’ve seen in the space, two things.
First, you’re not imagining it. Most of the people I work with at the hospital are well versed in other pieces of personal finance, in basic ETFs and retirement planning, but the majority are not into real estate and haven’t really considered it. That’s fine if it’s intentional. I also feel like the information just isn’t out there, or it is out there but it’s hiding behind an ad with some bro on a yacht.
Second, there are plenty of great examples of people like the ones you met today. Not from a real estate or finance background, just as busy as you are, who found a way to make it work and have had a positive experience doing it as a side quest. We exist. We’re just less vocal about it, which is exactly why I wanted to make this series.
About This Series
Thank you again to the guests for sharing their stories and their tips. If something from one of them was particularly helpful, give them a shout out in the comments. There’s more that they shared that didn’t make the final cut, so let me know if you’d want the full interviews posted somewhere.
This is a completely new format I’m testing. The idea was to borrow wisdom from this community and from other investors, but keep enough structure to make it easy to follow and keep it topic based. This time we talked about getting started. Next time it might be nightmare guest stories, or the systems people use, or how other investors think about scaling versus not, exiting versus not. I’m totally open to suggestions. I really just want this to be helpful to you.
Last thing: if you’d be open to sharing your own story, fill out this form or send me an email. I’d love to chat, and I know the audience would love to hear what you have to say. You don’t need to be some real estate guru. If anything, the more relatable you are, the more you’re wondering “who am I to have an opinion on this,” the more you’re exactly who I want to talk to.
Real estate isn’t a magic bullet, and it’s not the only way to build wealth or freedom. But it can be a powerful piece of your puzzle if you approach it thoughtfully, stay curious, and adapt as your life and the world change.
I’ll keep sharing stories and tools to help you figure out if and how real estate fits into your journey.
What’s the one thing holding you back from your first deal?
Leave a comment below! 🙂
