Return to site

How a Family Getaway Turned into an Airbnb Grossing $100,000+

Host Coach Airbnb Podcast Episode 53

March 10, 2025

Do you wish you could own a getaway place for your family that covered its mortgage and even cash flowed? Are you curious how it’s possible to run an Airbnb in a different state while you have a full-time job?

If this sounds familiar, tune into Episode 53 of the Host Coach Airbnb Podcast where Jenny and Bill Kirwan share how the news of an out-of-state grandchild sparked their Airbnb investment journey and led to grossing over $100,000 their first year as hosts!

After listening to this episode you will know how important it is to learn local short-term rental regulations before you invest in a property, and why the “feel” of your Airbnb is so important to guest satisfaction.

Read on to learn about the rarely discussed, hidden reward of hosting, and how the Kirwans keep their rental calendar full year-round!

Topics discussed in this episode:

  • How to overcome your fears of Airbnb investing
  • How county regulations can impact your Airbnb investment search
  • How to manage a successful Airbnb from another state
  • The importance of designing with guests experience in mind
  • The hidden reward of hosting
  • The value of a short-term rental “sherpa”

Host Coach Airbnb Podcast Episode 53 Show Notes:

 Can you tell us about the Airbnb property that you have listed? Where it is, how you found it, and what the backstory on that is?

Sure, the property we found is up the north shore of Lake Superior in Minnesota in a fairly remote area, but close to a very popular vacation spot for the people in the Twin Cities.

You're here in the Washington D.C. area. How did you find a property in Minnesota? What drew you to that?

Airbnb Investing to be Near Grandchildren

So the initial goal was to have a family getaway place near your kids, near your grandchildren. How did that goal evolve? Did you always know that it was going to be a short term rental?

No. We have very good friends who we have watched slowly grow a very substantial portfolio of vacation rentals, and we've gotten to experience their joy and see both going through the hosting process with their guests, but also whattheir properties offer their family and friends for getaways. We've always really admired them and kind of thought in the back of our minds, that would be a wonderful thing to have for our family.

Well, that's an exciting vision. How is the property performing for you specifically financially on a monthly or annualized basis?


A lot better than we had hoped initially. We're easily hitting somewhere around $10,000 a month, in these first 5 months. So, we're looking to gross over $100,000 in our first year.

mazing. Did you hear that? It's their first year. They had legitimate concerns about getting into Airbnb investing, were motivated to be near a grandchild and are on track to gross over $100, 000 their first year of investing in an Airbnb. Bravo! If you needed motivation or inspiration, folks, there you have it.

Airbnb Investing Goals

You both have architectural firms, so you're goal driven people. What were the goals for this particular property?

Well, my goal was really simple: to break even. I just wanted this to work out for our family. And, I was hoping that the vacation rental aspect of it would , subsidize our ability to have this place for our family to enjoy.

I had higher goals than that. I really wanted it to be something that would be supplemental income, and for it to be a place that we can pass down to our family. Also I started with this vision of and very much how we approach architectural projects. What can this place be and how do we make it stand out from our neighbors?

I love that.

As we've moved forward with this venture, I've been a complete convert. I mean, she's really taught me that those things really work. I mean, we've seen the responses from our guests about all these little details that Jenny really led and, it's been terrific.

Recognizing What Makes Your Airbnb Unique

Which is brilliant, and something that I do as well. Probably not as well as actual architects, though,

Did you have any fears as you began your investing journey?

I was just afraid of the Airbnb not working for our family. I didn't want to see it fail. Making this huge investment, I eventually got to the point where I realized, like most developers do, you just sell it if it doesn't work out. And I didn't want that to happen. I wanted this to work because this was something very personal to us with our family. It was going to be a place where we could really connect with our new grandchild. So I wanted it to work.

Airbnb Advice From a Fish

It's great advice. Advice from a fish. I like it!

What was the hardest part of your process as you started this whole adventure in short term real estate investing.

I think it was the remoteness from the location for us. We had to very quickly get to know the community, find a handyman who we could rely on, find a cleaning company we could rely on. I think those were the hardest things

How to Find Remote Airbnb Help

How did you go about solving that?

Very early on, I was at the house and we were getting the Internet set up and I asked the installer, what's a good way to find cleaners, to find handyman? And he recommended a Facebook group for our area. So, I joined it, and then I started asking questions about, where can I find a good handyman or a cleaners? And I got a ton of responses. So that's, how we ended up finding our handyman who has been amazing and who's also ultimately connected us to our cleaners.

We see the cleaning aspect as one of the most important, right up there with us as Airbnb hosts. Our cleaners, they have to perform.

So the best thind to do was have boots on the ground, get into the property, get into the neighborhood, share your questions with the community, and start putting that question out there?

Yes. And also just being sensitive to the community too. I think our area, there's a shortage of housing and we might run into some resistance. We have not found that, but we were prepared. So we were being sensitive And it's also been fun to reach out to some of the local businesses in the town that we're near: the coffee shop, the brewery, one of our favorite restaurants. I'm really promoting them to our guests,

The Unexpected Rewards of Airbnb Investing

What other surprise benefits other than the financial benefits have come to you through this hosting journey?

I think both of us have been very shocked that one of the things that we have found the most rewarding almost more so than the money we're bringing in, is this connection that we're making with our guests, We're just being a little part of their lives for a short period of time. But in that short period of time, we have the opportunity to create this amazing backdrop for their memories.

We had guests a couple of weeks ago - they were on their honeymoon. They had just gotten married on a Thursday. They were at our house on a Saturday. We had known about this for a while and had gone and bought flower petals and card and champagne. for them to enjoy during their stay.

I love the soft side of Airbnb hosting and investing. There's the hard side, which is the hard money and we're all trying to cover our mortgage or we're trying to cashflow X amount to make sure we can have this financial freedom. But there is the soft side. And I love that part of connecting with guests, being a part of their life story, their honeymoon, their engagement. It's just, it's joyful. And I don't know that everyone knows that.

So listeners, there's the joyful part of being an Airbnb host that isn't always in social media and isn't always at the stories that you read, but it's a really great part of it.

Airbnb Regulation - Do Your Due Diligence

Did you make any mistakes in your Airbnb investing journey?

Oh, sure. You've talked about this on some of your podcasts, but really understanding the vacation rental licensing processes in these communities. We initially started looking at a property that was much closer to our kids. As we started to dig into the details and started talking to real estate agents, they immediately notified us that the city of Duluth has already issued all their licenses for vacation rentals. There's none available. So you're going to have to wait until somebody releases their vacation rental to have a chance at that license.

So as we started to look at communities, we ended up where we are today in the community we're in, which is a much better community because it really is a vacation spot. Other properties we were looking for were more about proximity to our kids and less about were they popular hotspots for vacation rentals. And fortunately, we landed in a community where the licensing process was much more open to vacation rentals.

So do your homework on the regulatory environment?

Find a Real Estate Agent Who is an Expert in Short Term Rentals

Absolutely. And you've talked, on your podcast about reaching out to real estate agents who really understand the vacation rental. I think that our impression is where we are that's a relatively new thing for real estate agents to be experts on. But, our hope is over time as we look for future properties to possibly grow our portfolio, to really connect with real estates who specialize in Airbnb investments.

Ooh, future properties?!

Yes,

I love people that were afraid to start for very real reasons. moved through the fear, just kept swimming like Dory, have had financial success, have had emotional connections and personal enrichment from the journey as a host, and are now looking at expanding their portfolio. That's a beautiful circle of the journey.

We are under contract for our 11th place. So it just keeps going, no matter how many properties are in your Airbnb portfolio.

How An Airbnb Coach Can Help You as a New Investor

Outside of understanding the regulations for short term rentals in your desired investment area, what advice would you give our listeners who are thinking about getting started?

So, you guys did not pay us to say this, but really connecting with somebody like you guys for Airbnb coaching. Our close friends who we mentioned earlier, who have the portfolio on the beach, highly suggested we talk to you. And, we set up an initial consultation. You helped us look at our property and it's potential. And you were very positive, very encouraging about that and helped really launched us into successful set up and listing.

Host Coach podcast, and reading your book. I mean, there's so much valuable information that isn't anywhere else. And that connection with you was as incredibly helpful and listening to your podcast also helped me with some of my initial fears and anxieties about being a property owner for a vacation rental... and that was really important.

different Airbnb tools that we're now using RankBreeze and Hospitable. We use those and they're fantastic. They make our jobs so much easier. It's amazing how those third party apps the way they dovetail so smoothly into Airbnb, It really makes our jobs so much easier, and manageable since we both have our own businesses.

2 Great Tips For New Investors

There's two great tips that we learn from you all.

The first one is a really sort of simple one is: we initially set out to not allow pets in our vacation rental. I had a bad experience at a vacation rental years ago. Where property that allowed pets and when we got to the property, it was full of fleas -so we had to leave the house while they fumigated and come back at a later time. So that was kind of our initial concern

But, Culin in one of our meetings with you, you sort of walked us through the data on what the potential for a pet-friendly property was, how many people actually have pets, and want to travel with pets - just like we take our dogs everywhere., Once we came around to let's listen to Culin and let's open this up to families with pets, probably every other guest we have brings their pet. So it's really helping us to fill up our calendar.  

PriceLabs, I really follow the advice of looking 14 days ahead.  And, we had some of those gaps, then reduce the prices by 5% and watched those dates fill up! I look at the ones further out, reduce them another 5%. and booked! So, being interactive with Price Labs to adjust that pricing when you do have holes in your calendar has proven to, really fill it up and not be a lot of work.

You've made my day saying all these wonderful things about us as coaches and the podcast and book!! We're sort of like short term rental Sherpas. We're supposed to take the weight off of you because there's so much to do and think about when you're new at something. Having a Sherpa to guide you and carry you and give you the right tools, that's what we do. So it's delightful to hear that that works and has created something that's making your life better. That's awesome.

 So there you have it. You now know how important it is to learn local short term rental regulations before you invest in a property, why the feel of your Airbnb is so important to guest satisfaction, the hidden reward of hosting, and how the Kerwins keep their calendar full.

free 30 minute Airbnb coaching session to see how we can help lighten your load and get you to your goal faster!!