From Side Gig to 8-Figure Airbnb Business… and Private Equity Is Calling

Matt Floyd (0:00)

We didn't pay ourselves for two years after we quit our W-2 jobs. And we need to remember that we're in a discretionary spend business. This is vacation spend that does fluctuate based on the economy, based on wars. Regulation is a big risk for us. The OTA platforms owned our customer, a lot of it. So there are risks in this business that we don't wanna be just assuming that everything is gonna be sunshine and rainbows forever going into the future. It's foolish to assume that the opportunity will be around forever. Cycles come and go, right? And we saw the Vecasa cycle where the acquisitions were coming in. There's also a point where you may want to exit and there's no buyer that's even interested.

Michael Sjogren (0:39)

When you're building your business, always build it with the intent to sell, even if you're never planning on selling because 80 of all businesses exit disadvantageously.

Craig Gerulski (0:48)

You have all the different private equity groups. They all have different ways of running their organization and different timelines. So it's like if you decide to go that route, what's the best fit, right? It's not just the initial payday or maybe different bites of the apple, right? Different recaps, but it's like, all right, what does my day to day look like, right? Or am I expected to do a bunch of tuck-ins? Am I expected to just kind of grow at a 10 or 20% rate? And then what's the incentives, right?

Michael Sjogren (1:13)

You've essentially rebuilt the business a few times as you've continued to scale. So for somebody that maybe they're at that 10 unit mark to 25 and then 25 to 50 and then 50 plus, 50 to that 100, how has that business evolved for you guys over the year? All right. Good morning, San Diego. What's up, Stay Classy guys? How are we doing?

Matt Floyd (1:32)

How's it going, Mike? Good to see you always.

Craig Gerulski (1:35)

Yeah, good to see you. I think this is round three or four with you.

Michael Sjogren (1:38)

I know.

We had to do it again. Obviously, enjoyed hanging out with you guys this past week at VRMA.

What were your thoughts? This was my very first VRMA and I was talking to some folks about this. For me, it felt nice to see these two worlds merging because I feel like for a long time, you had the OG property management companies and then you had the newer co-host PMs and those worlds didn't really merge. I feel like there's been some changes at VRMA where they're a lot more welcoming now. I was seeing those two worlds come together, but I don't know if you guys noticed that. It was so apparent to me when I went in there. I was like, this feels like a breath of fresh air.

Matt Floyd (2:18)

Yeah, our first VRMA as well.

We don't have much to relate it to from past years, but it was great to see a lot of the newer groups that have come up in the last five years, five, six years, where what we expected was a lot more of the 10, 20, 30 year operators, which there were some there, but there's definitely some intermingling between them. Saw a lot of AI softwares that were there. That's a lot of new excitement when it comes around the vendors.

We just spent the whole time chatting with a variety of different people, older, new operators. So the networking was amazing from my perspective. I think the venue setup was great. Being able to go to the sessions, come back in. I thought the quality of the sessions was great. So yeah, I look forward to doing it again next year.

Michael Sjogren (3:07)

Craig, what were your one or two favorite sessions that you got out of there?

Craig Gerulski (3:12)

Yeah, there were so many good sessions. When me and Matt were looking at the agenda, we're like, there's probably 20 talks we want to go to. And like Matt said, we had all these plans and we ended up seeing a lot of people we knew in the industry. So we ended up networking a lot of times and talking to the vendors we use. So it was a lot of fun. But I think the one that I took away is Steve Schwab's, The Breakpoint to Stanley. And that's so relevant to every part of the business you're in. Going from your first property to 10 to 15 properties where you might want to hire your first VA.

And then 10 to 50 where you might want to hire a team of VAs and have a team leader.