Considering a Vacation Rental? Let's Hear From a Vacation Rental Veteran

Dream investment or real estate nightmare? On this episode, we have Bryan Bailey on to talk about his experience with the vacation rental investment strategy. We cover motives, returns, reserves, startup costs and everything else you need to consider to be successful with a vacation rental.   --- Transcript   Tom: Greetings, and welcome to The Remote Real Estate Investor. On this episode we're talking about Vacation Rentals with Bryan Bailey. Bryan is a vacation rental veteran. And he's going to talk about how he started his portfolio, some of the costs all that good stuff. Alright, let's get into it.   Tom: Bryan Bailey, welcome to the remote real estate investor. Before we get into the topic today, why don't you give listeners a little bit about your background?   Bryan Yeah Tom thanks, I'm really happy to be here. Well, well, let's just stick to the real estate portion. I've had a very eclectic background. But you know, I got into real estate, like most people listening to podcasts reading, you know, the, all the books about how to get rich quick, you know, and it got enamored with that. But essentially, you know, out of college, I started in commercial real estate on the west coast. I loved it. I was doing structure finance, working on some big deals, and San Francisco and LA and Portland up and down the West Coast and absolutely loved it.   And, you know, I wasn't looking to get into SFR. But through a series of circumstances, yeah, I took a job at a small company that was buying single family homes at that time that that company was Waypoint homes. And in 2011, when I started there, we maybe had 300. In total, you were the first employee there, I believe, Tom and I was right after you. And you know, we grew that company to over 15,000 homes from 300. You know, it took the company public and eventually sold the firm. And as some of the listeners may know, the former waypoint is now part of invitation homes. So you know, that was a great run. And now I've been at roof stock for three years as a co head of investment services. And, you know, we're doing great things over here.   You know, I would just say, I feel like I've been a pioneer in the institutional, single family rental space, the past 10 years has been unbelievable, but when you see what's happening right now, with all the attention that the industry is getting all the institutions, even a lot of individual investors are getting more excited about the space, I think the next 10 years will be even better than the last.   Tom: And something that just kind of sticks out is you know, working at those companies are growing really quickly, you end up wearing a ton of different hats. And I thought one of the roles you had was so neat is whenever this company that was buying a bunch of houses would open a new market, Bryan would be the tip of the spear and basically, you know, work with some of the local pros and get the growth in these as we would open up Dallas as we would open up Atlanta, Bryan was the the road dog in opening up those new markets.   Bryan: So I was a road dog and the high school and college too. Just so you know.   Michael: I'm sure you've been called the worst things.   Bryan: And yeah, when we were running on empty is like, Yeah, I was a road dog. But yeah, to your point, Tom, I've worn many different hats and SFR like you have and it's just been awesome experience, you know, of a lifetime.   Really, you know, like you said, when we open up new markets, there really wasn't a playbook. There was no industry. So it wasn't a commodity business. Like it's starting to get now on these platforms. And so you just kind of have to figure it out. And I remember many times, as you were saying, whether it be you know, a Dallas or a phoenix or in Atlanta, you would go there and sit in a Starbucks with your first employee and just start mapping things out. So yeah, from there to heres is a lot of fun memories. We drink the entrepreneurial, gritty Kool