Getting Your Foot In The STR Door Using House Hacking

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In this podcast, Liam and special guest Drew Hittner from discuss house hacking, a popular strategy in the UK and the US, and obtaining lending for Airbnb rentals. Drew, an Airbnb super host since 2016, shares his journey and the concept of house hacking, where you generate income from the property you live in. Drew manages seven units across three states with minimal time investment, attributing his success to surrounding himself with motivated individuals.Β 

He also introduces HostLoan, a lending solution tailored for Airbnb hosts, emphasizing the importance of specialized lending for hosts with multiple mortgages.

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Timestamps (audio)



[00:00:00] Liam: Hey, everybody. Today we are talking about house hacking, which is a very popular strategy, both in the UK and in the US, and also how you get lending to do house hacking and just generally Airbnb and lending in general. And this is one of the things that many people talk about. They go, I want to get into a short-term rental.

[00:00:19] I just don't have the money to do so necessarily now. So. What we're going to be doing is diving behind the host with a very special guest. Who's going to be talking us through this subject today? And, uh, if you haven't heard of the Roosley podcast before, or this is your first time listening, what we do is we give hosts the tools, the tactics, the training, and most importantly, the confidence to go out there and get more bookings.

[00:00:41] We do a mini-series where we dive into a host's journey, which is exactly what we're doing today to help us answer that question. My name's Liam Carolan. Today we're going behind the host with Drew Hittner and he is from Hostloan. co. So you can go and check out Hostloan. co. But, um, before you check that out, let's get Drew's story and find out much more about how he does his house hacking and some of the, um, truly amazing tips.

A bit about Drew

[00:01:08] Let's dive in. Uh, Drew, do you mind giving yourself an introduction, uh, where your business is in the world and anything else you'd like to share?

[00:01:15] Drew: Absolutely. Well, first and foremost, Liam, thank you so much for you and Boosley for having me as part of the podcast today I'm 37 years old, live in Arizona, and I've been, I don't know if this is a bad word or not, but I've been an Airbnb super host since 2016 and, uh, also doing some direct bookings throughout that time as well.

[00:01:36] And you know, a quick elevator pitch of how I introduce myself, and my company to others is don't roll the dice with your lender. If they're not an Airbnb super host, I have had a major focus on the type of lending to help serial real estate investors, because after you get a couple of mortgages in America, um, and other places too, it becomes more difficult.

[00:01:56] So I've tried to just be a professional problem solver in that field. So how to make it just as easy as the first one for the fifth? 10th and 20th. So, um, we got a great team here. Everybody on my team owns a rental or short-term rental as well too. So we all clock the same, um, the same window.

How Drew gets started?

[00:02:15] Liam: How did you get started?

[00:02:16] So, um, I'll definitely want to dive into the house hacking side of things, but take us back to how you got started and, um, how you became a super host and, and how many units you've got now.

[00:02:26] Drew: Yeah. So it's a great question. So I got started, you know, I, everything in life I think happens and revolves around a compelling event.

[00:02:35] So I've had a couple of these in my journey in 2016, or maybe it was 20, it was 2015. 2015, I had a merger or an exposition with my W2 or day job, my 9 to 5. And at that point, it didn't take long to figure out that I just took a pay cut, but they still wanted to keep me. And so I had to do one of two things.

[00:02:56] I had to, in my head, I had to either put my truck on Uber, which they wouldn't accept or Airbnb. Was a platform that looked like a side gig source of income for me. So that was it. Moved out of my apartment whenever it was rented. I stayed with my girlfriend and I was blown away after just two weekends. It paid me to live there now.

[00:03:21] So I just had to sacrifice a little bit to put myself ahead. And then at that point, I just got, you know, I play golf. So you get bit with the golf bug. You play a lot of golf, but I got bit by the real estate bug at that moment. And then that was just the snowball that kept building that evolved later into a lending career and business as well.

[00:03:40] Liam: Why is that a good, um, a good strategy for people to consider when starting?

[00:03:46] Drew: Yeah. So the one thing that I heard from somebody that I look up to is David Green. He's the host of BiggerPockets. I know he always says it is real estate investing with training bills. So, there a multiple different facets, right?

[00:04:02] You can buy a house that has a business underneath you. You run out of the business that helps cover the mortgage or your housing expenses. You can buy a five-bedroom home. And rent every single one of those bedrooms out, that's going to help with your housing expense. I just didn't know it was house hacking at the time.

[00:04:20] I just knew I needed to save money. And so I thought just by lending my apartment to somebody else for the weekend, that that would make life easier for me. And I didn't find out until about two or three years ago, that's called rental arbitrage. So I just thought I was subleasing my apartment at the time, but that's house hacking, right?

[00:04:43] You can, I mean, technically I was apartment hacking, but it's any way that you can generate income off of a property that you live at, either pays you money to live there or just kind of offset, your housing expense.

The current look of the business

[00:04:56] Liam: What does the business look like now? How many units do you look after? And, um, Then we'll segue into the, um, the lending side of things.

[00:05:06] Drew: Yeah. So right now I have seven units across three States that I probably like to say I self-managed between three and four hours a week right now. Um, one of those units just had a major flood, um, three weeks ago. So I'm fighting that, but my team is, has been amazing that I want to be able to do it without them.

[00:05:26] Um, I've been up to 14 units. I sold some in 2021. Beginning part of 2022. Um, I've done the bursters, the burrs, the long-term holds, but then I eventually got up to about, you know, um, I was up to 15, but some, one of those was a long term. So I had 14 listings at one point that I was on. pace to do right around 690, 000, 700, 000.

[00:05:57] But I got rid of some of them because I didn't have the right team in place. And so then I just kept the ones that I liked, got rid of some of the others. And then with some of those proceeds, what I did was snowball that into my next big venture, which is the, you know, short-term vacation friendly You know, I guess mortgage company is what you could call it.

What’s the secret sauce?

[00:06:21] Liam: What would you say to somebody who's looking to be able to spend the same sort of time on their business per week, um, as you're spending there while managing successful properties across, you know, several different states? What's the, what's the secret sauce?

[00:06:39] Drew: Find the right friends. Change your circle of friends, unfortunately, you know, and that never feels comfortable to say, but, you know, the most successful people I know have multiple businesses, you know, Rob, you mentioned his name earlier, he comes to mind because if you have the vision, you're, you know, I know Rob's a pioneer, then other people are just going to, that's an exciting journey for a lot.

[00:07:01] And if you are good at forecasting a vision, then everybody wants to be part of that growth. So I think, you know, that's, that's the first thing that comes to mind. I think that's the most important. Host

[00:07:11] Liam: loan. Talk us through, what is host loan, how you came up with the idea for it, and uh, what does it do?

[00:07:20] Drew: So host loan is, well, I would say, when somebody asks me, Drew, what, what do you do, or how, how can you help me? When I talk to a client, it's, I say, don't roll the dice with your, your lender, super host. And, you know, there's all types of mortgages out there, right? And there are all types of mortgage companies out there.

[00:07:41] Okay. I just chose this focus, hyper-focus on one niche. There's reverse mortgages, there's government loans, there's non-QM, there's hard money, there's private money. I just chose to focus on the product that would best fit me. And so I'm a host and I did loans. So they're, they're coming with right. And, you know, it's other people.

[00:08:06] They're just as smart, if not smarter than me, say the same thing. If you can find a problem and then create in any fashion a way to solve some of that or all of that problem, you're going to have business. Being in the government loan section for so many years before I started HostLoan, I knew that if somebody had two or three mortgages on their credit report, then getting that fourth one was going to be more work than the first three that they did all combined.

[00:08:35] So like, how do I find a solution to that? And I was able to, and that's why we've been able to, to grow And then, you know, just, you know, working with Rob, helping the host campers, things like that. Just sharing the information that I have with others is, has been, a way that we've been able to grow.

[00:08:53] Liam: Having a blast. Gonna get it on the Boostly podcast. Bruce Lee. Let Bruce Lee 'cause it's so hard on the teas. Loosely making up those rhymes. Don't write it, just do it loosely.