When I sat down with Alex Steeg, I knew we were in for an inspiring and value-packed conversation. From barely affording rent in grad school to managing over 40 short-term rental properties, Alex’s journey is a masterclass in starting with grit, scaling with strategy, and embracing disciplined growth. If you’ve ever considered getting into real estate, transitioning from long-term to short-term rentals, or you’re simply curious how to make your listing stand out in a saturated market, you won’t want to miss this conversation. He doesn’t just share what worked—he breaks down the numbers, the mindset, and the hard lessons. It’s the kind of advice I wish I had when I was starting out.
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Hello everyone and welcome back. I’m Adrienne Green and today we are here with Alex Steeg. Alex, thank you so much for joining me.
Thanks for having me, excited to be here with you.
I can’t wait for Alex to share all of his wisdom. So get ready—he’s going to have insights that are going to help you scale, systemize, and create more freedom. His life has been transformed through his investing over the last few years and he’s going to share it all with us. To give you a little bit of a background or big picture, Alex is a short-term rental investor himself. He helps co-host for other short-term rental owners. He has a lot of experience dealing with all of that fun of short-term rentals. And then he also uses that experience to help coach people who may want to self-manage their properties and pass along his wisdom in that way. So you do a lot right now, Alex, but let’s start at the beginning. How did you get involved in real estate investing in the first place?
Yeah, that’s a great question. It’s an interesting story. It goes back to 2019. My wife and I had been married for about two years. I was 25 at the time and I was in grad school. My wife was working in nonprofit. I was in grad school. We just didn’t have a lot of money.
It was right around the time of the month where it was time for us to pay rent. Looking back, it was an awesome apartment. It was super cheap, but at the time I just had no money and I could not stand the idea of paying rent when I didn’t have a lot of money. So it just kind of dawned on me, what if I tried to buy my own two-family, rent out part of it, live there, maybe that would make things a little bit easier and cover the mortgage.
It also coincided with the fact that I had about a year left in my master’s program and I was trying to figure out what I was doing. I was in seminary, so I was looking at potentially working at a church and I just didn’t really want to do that towards the end of my time. I started reaching out, thinking about some ideas of what I could do for work. I ended up working back at the college that my wife and I had met at, where I became a resident director. So we had free housing. Right before that, I kind of had this idea that in this last year of my master’s program, this was the direction that I was going to head.
I really put things into high gear—like, we need to find something before we move onto campus so that we can live there for a couple of months, get some tenants in there, and then when we move out, we can replace ourselves with a new set of tenants. It was really tough to find a two-family. I’m in a little bit of a higher price market north of Boston. We had low income, so it was hard to find something. We scraped together every penny that we had. I took advantage of a first-time homebuyer $10,000 0% loan in Gloucester, Massachusetts. We bootstrapped everything. I don’t advise this, but we lived off of 0% credit cards for the first three or four months after we purchased because we spent every penny we had to get into this property.
We found tenants and moved in literally three days after we closed. I knew them from the area. They stayed with me for a couple of years. The plan worked out perfectly. I got the job, we moved onto campus, I rented the house out. That’s when we started getting the cash flow from that property. That’s when I really started to see that this could work for us. We had no living expenses, and it just kind of ballooned into buying another property in 2020, another two-family in 2021. That’s kind of where things shifted for my wife and me—where we started to pivot into the short-term rental space.
We had been totally bought into the long-term rental traditional mentality up until then. It wasn’t until my wife found out she was expecting our first son that she needed a job transition. She was wrapping up her time with a nonprofit and had about eight months until our son was born. She got connected to someone who had her managing his real estate portfolio, some long-term and some short-term rentals. In the process of learning to manage his short-terms and as they parted ways, it was obvious—we love real estate, it’s been good to us, and she had this niche expertise now in short-term rentals. We live in a traditional vacation rental market. So it was a no-brainer to start the Airbnb management company we launched in March or April of 2022.
Since then, it’s exploded. We manage about 40 properties. That pivoted us into buying a 10-unit that we operate as an inn. My thesis is that you can apply the same systems and operations from short-term rentals into the commercial real estate hospitality side of things. Because of the way those get valued, it made sense to try and make that pivot.
Wow. I love that whole history. We started from that anger—and I think realizing the value of a dollar when you don’t have a ton of them is a major motivation. And the funny thing is, starting at the beginning, you’re like, “Okay, I had this idea,” but then you got free housing. A lot of people would take that as the easy button and not keep pursuing the house purchase. But you didn’t. You chose the hard path, even when that meant living on credit cards. I’m curious—what was your mindset, your mentality of choosing that hard path? How did you and your wife make that tough decision and stick with it?
That’s a great question. I have to give my wife a lot of credit. I know what my finances looked like before I got married and what they looked like immediately after. I credit a lot of what we have to her and the discipline she had with finances from day one—she graduated, paid off a lot of student loans quickly while working at a nonprofit. We applied the same lessons and disciplines she had learned to real estate. For example, we weren’t going to touch the cash flow. We were going to reinvest that. Even if our standard of living increased a little bit, we were not going to allow lifestyle creep to get us. We were going to play the long game and enjoy the fruits of our labor later.
Also, being in our mid-20s with no kids, we were able to grind it out. If I were to start this now with two kids and one on the way, that would’ve made things much more difficult. I do attribute a lot of it to getting into real estate at a time that felt like a barrier, but in hindsight, was a great time to start. So part of it’s skill, part discipline, part good timing.
Well, I think you give too much credit to the timing. From an outside perspective, a lot of people would say being broke and in school is a reason not to get started. So give yourself some credit. You also give a lot of credit to your wife, which is awesome. Now, I also transitioned from long-term to short-term rentals, and I think that’s not uncommon. What wisdom would you pass along to someone considering that move?
The biggest thing: invite someone into the process who can pull real data. I see a lot of people who acquire properties and later realize they’re not competitive. In a post-COVID world, you can’t just put up an air mattress and call it a day anymore. People used to get away with launching with a “Coming Soon” photo. I did. I booked a summer with no real listing. But now, you have to underwrite carefully and conservatively.
I tell people not to make financial decisions based on best-case revenue. I undercut 10–20% so they’re protected if the market shifts, regulations change, or something unexpected happens.
Also, make the property the destination. Ask, “How do I make this listing Instagrammable?” People should want to go there and take photos. But I see people spend all their money on acquisition and then skimp on furniture. That doesn’t work. You need to budget $4K per bedroom and $5K per common area. I’d rather someone buy a smaller property and stage it well than get a big one and have to furnish with leftovers from Facebook Marketplace.
That’s a great point. What are the design trends in your market right now?
My market covers Marblehead, Salem, Beverly, Manchester-by-the-Sea, Gloucester, Rockport, Ipswich, Essex—all coastal towns north of Boston. It’s a traditional vacation market but not wildly competitive. The listings that stand out either have water proximity or water features like hot tubs or pools.
One of our Rockport properties has a pool. In a market of 350 active listings, there are only two with pools. That house has nearly 100% occupancy from May through September. That’s powerful.
Also, look at trends—like pickleball. That amenity alone has boosted bookings for people who’ve added courts. Watch what’s culturally trending and consider what rare amenities exist in your market.
Do you recommend social media accounts for listings?
Eventually, yes. But not at first. I see too many people try to do everything and then do nothing well. Prioritize Airbnb first—get systems, pricing, and automations locked in. Once you’re solid, then expand into Instagram and direct bookings.
Now about seasonality—how do you recommend handling off-season dips?
It’s about pricing strategy and risk tolerance. Two years ago, I would say keep listings open year-round. But now, it varies. Tools like PriceLabs help a ton. Most owners here don’t adjust prices properly, so we’re able to undercut a little and stay booked.
Also, Airbnb’s Insights tab shows conversion data. People may leave at checkout because of fees or poor photos. It’s not always pricing. If your listing photos are bad or the design doesn’t resonate, people won’t book—no matter the price.
If you don’t have the stomach for seasonal swings, that’s okay. We place midterm or winter rentals for some clients—like travel nurses. It just depends on what works for you.
That’s such great insight. Now let’s wrap with some closing questions.
What’s your go-to tool for managing operations?
Hospitable. It’s user-friendly, and the team is awesome. They’re always innovating. We couldn’t manage at our level without it.
What advice would you give your younger self?
Build your team sooner. We managed 25 listings ourselves before hiring a virtual assistant. That changed everything. The ROI is huge. Don’t wait.
What’s a book that’s been transformational?
Brandon Turner’s The Book on Real Estate Investing. It simplifies everything. His napkin math and checklists helped me stop overanalyzing and just get started.
And if people want to connect with you, what’s the best way?
Instagram @alexstieg or search Alex Stieg on LinkedIn.
Thanks again for joining me, Alex!