The Definitive Oral History of Short-Term Rentals, Part 2

Skift Take

Airbnb broke things as a startup, but a second generation of executives starting in 2013 knew the maturing business had to start playing by some of the rules. Part II of this oral history details many of these changes, as well as the clash between individual owners and property managers.

At the beginning of this second part of the story, Chip Conley has joined Airbnb in 2013 as head of global hospitality and strategy, and delivers a message that isn’t always warmly received internally: The company needs to start paying occupancy taxes. He opens up a dialogue with big hotel chains. Laurence Tosi becomes Airbnb chief financial officer in 2015, and property managers begin to take share on the platform. Elsewhere, property managers such as Vacasa in the U.S. and @Leisure Group in Europe begin to get noticed.

The Experts

We interviewed 30 executives and entrepreneurs in the U.S., Canada, Argentina, Germany, the Netherlands, Switzerland, and the UK for this Skift Definitive Oral History of Short-Term Rentals. They included founders, co-founders, CEOs, and other top brass — past and present — of short-term rental brands, major online travel agencies, as well as property managers and hosts.

Patrick Andrae
John Banczak
Rich Barton
Dave Bollinger
Eric Breon
Sandra Brown
T.J. Clark
David Clouse
Chip Conley
Jeanne Dailey
Brian Egan
Glenn Fogel
Jon Gray
Jennifer Hsieh
Jeff Hurst

Merilee Karr
Dara Khosrowshahi
Simon Lehmann
Aurelie Lepercq
Doug Macnaught
TJ Mahony
Ivan Marenco
Hunter Melville
Kim Rubey
Brian Sharples
Carl Shepherd
Rhonda Sideris
Laurence Tosi
Tobias Wann
Pamala Parris Wideen

HomeAway Contemplates Bookings for the First Time

Carl Shepherd, HomeAway

We’re looking at our business model around 2014. We realize, OK, it’s now time. One critical thing: In our initial business plan for Austin Ventures in 2004, we included a page that we would kill the subscription business and move to revenue share within 18 months. We believed it. We didn’t make it. And, 12 years later, in 2016, we are still subscription. And why? Because they owners won’t do it. They simply won’t do it. Well, we get to 2014 and we realize, we’re going to have to do it because now Airbnb has changed the way people look at this industry. And while Airbnb’s take rate was really 15 to 18 percent on average, it wasn’t perceived to be that because they were only taking 3 percent from the host. They’re taking the rest of it from the traveler. The traveler’s paying it anyway, even if the owner collects it and pays it. It is a reduction of the revenue to the owner, right? Therefore, it’s an owner expense regardless of who pays it. 

So we thought, OK, we have to move this business to online booking. So we looked at this and said, we’re going to have to take our public investors through a journey, and that journey’s going to be our move from subscription to online booking. And there’s going to be risk associated with that. Our revenue might not be predictable as it was during the previous months. So before we make announcements that we’re doing all of this, I’m going to go around to all the usual suspects and make sure that no one’s going to come out when our stock is depressed and run at us. I just needed to see what was going to happen. 

So we had hired Qatalyst. Qatalyst is an investment boutique run by Frank Quattrone, George Boutros and our guy was a guy named and Jonathan Turner. The reason we hired them was that Frank was prohibited from issuing securities in his settlement when he got arrested during the dot.com bust. But the great thing about Qatalyst was they couldn’t take you public or they couldn’t do things like that so they were the perfect M&A partner. Because they could only represent M&A transactions. We had hired them because if we were approached we knew that it would come from one of our major bankers, Goldman, Morgan Stanley, JP Morgan etc. And then, if we were approached by someone and we needed help on an M&A, then the other guys who knew us so well suddenly became untethered.

Let’s say you hired Goldman Sachs to represent you on M&A. That means everybody else is out there trying to bring you a better deal. But you’re being shopped in ways that you’re not controlling. So if we were hit with an M&A, we thought it was logical that we’d be represented by somebody who couldn’t take us public. Who had no future interest in the buyer because they couldn’t work for a public company to raise a convert or to raise equity. They couldn’t do that. They wouldn’t see the buyer as their future client. They’d see us as their client. So Jonathan Turner (co-founder Qatalyst Partners) and I started a road show and I visited everybody. I came back and said, “I really think that there’s so much going on right now that the likelihood that someone wants to buy us in the next several months, while we’re making this transition, I’m placing pretty low. Booking’s got all it can say grace over right now. Dara (Khosrowshahi, Expedia) has all, he can say grace over right now. And none of them like the subscription business. We need to get through this transition (to pay per booking versus the existing subscription model), and then when we come out the other side of this, we may have to worry about this (M&A) again. But during the transition, I think we’re fine. I wouldn’t call it a roadshow. I’d call it a visitation among friends. I visited Glenn Fogel at Booking. We talked with Dara (Khosrowshahi) and Mark Okerstrom (then CFO of Expedia). We visited all of them. We come back, Turner comes in, we make a presentation, we say we’ve got six to eight months to make this transition. And I thought, OK, now if we’re going to be making this transition, I’m 63. I think I’m going to go on. I think I’ll retire because during this transition, there’s no more M&A, we’re totally adequately staffed. I’m going to stay on the board, Brian (Sharples, then-HomeAway CEO), and I’ll come back if we do something. But right now, I think, it’s time for me to retire. So on September 11, 2015 I retired. We had a party.

And then on about September 18th or 19th, the next week, Jonathan Turner calls me and says, “Carl, I have a term sheet from Expedia.” I said, “What? He said, “Yeah, we have a term sheet.” I said, “OK, let me get in the car. I’ll go down to the office.” So I drove down to the office and said, “Brian, we have a term sheet from Expedia. It’s going to be coming in pretty soon.”

It came in, we looked at it and I said, “OK, this is something that’s credible. It’s certainly within range of shareholder value.” We made that determination. So we went out and we had said, we have to test it. So we went out to test and, if you remember, Booking had a significant cultural problem. We didn’t know it at the time, but it resulted in the resignation of Darren Houston (Booking CEO). Glenn (then-head of Booking’s worldwide strategy and planning) just said it’s not the right time for us.

We certainly weren’t willing to pay (what Expedia paid for HomeAway, $3.9 billion). That’s for damn sure … Obviously, Expedia, they have grown, it’s very nice. So it worked very, very well. Who anticipated a pandemic? Really? But the truth is it’s good work by them. Congratulations to them. Nice. At the time it did not seem to fit what we needed to do for the price, the work it would take.

Glenn Fogel, Booking Holdings

It was a very good offer from Expedia. I had already retired and I said, our calculus was this. We have a lot to do. We have a lot of work to do. We’re going to be changing the way this company works. But this is really good for every constituent. Our investors were going to make a lot of money. For our staff people, we had been very generous with stock options and RSUs (restricted stock units). This is life changing for a thousand people in our company. How can we not seriously consider this? So we negotiated it and we got a really good deal. They told me they were going to close it on December 15th. By the time we finished, it was almost the end of October before we said we’ll take the signed term sheet. How are you going to close this in basically two months? October and November. And they did, they closed it on 15th. 

Dara Khosrowshahi, Expedia CEO from 2005 to 2017, saw his company acquire HomeAway in 2015 for $3.9 billion.

Expedia CEO Dara Khosrowshahi speaking at Skift Global Forum 2016 in New York, N.Y. The executive became Uber CEO in 2017. Source: Skift

Dara Khosrowshahi, Expedia:

I think for Expedia, we were watching the space pretty carefully and it was really a buy versus build kind of a decision. We were building our own. So our partner supply group was going out and negotiating inventory and building deals really through smaller management companies, starting with urban destinations, which is kind of the natural strength of Expedia and Hotels.com. So we were wiring up inventory, just like Booking.com has been wiring up inventory, over a long period of time. 

I think definitely that Booking.com and us were going to build it organically anyway. The HomeAway acquisition allowed Expedia to leapfrog some of those efforts. And it definitely came into the consideration set, although I would say that I was thinking more about Airbnb than I was about Booking.com in that particular space, in that particular circumstance. It was clear to me that the lodging aggregator business would consolidate into three big players. It was Expedia, it was obviously Booking.com, and it was Airbnb. So we’re always thinking within that strategic context.

Airbnb was a unicorn when it meant something to be a unicorn. So I think it was just completely out of the consideration set.

I had known Brian Sharples and we’d been watching HomeAway and I think HomeAway started to hit some difficulty and started seeing some choppiness in the waters as it related to their model, and the subscription model and the changes that they had to go (through). So we saw an opportunity. 

One was we knew that market had enormous potential and that HomeAway needed to make a fundamental transition into the transactional side of the house. And they hadn’t built those muscles internally, obviously Expedia had. And that was really kind of the transition that company had gone through, the desire for Expedia to get deeper in lodging and vacation rentals kind of made it all happen, but it wasn’t one of these deals that happened instantly. That was obvious. There was a lot of difficulty in finally getting it done.

I’ve been talking to Brian (Chesky) about Expedia and the Airbnb working together in one way or the other. We brought a demand profile that was very different from their demand profile. Could you have the best of both worlds, one or the other? And we could never get there. Everyone knows everyone in that industry. 

We (Expedia) had always looked at HomeAway. HomeAway had always traded at these incredible premium valuations because of the growth rate, the size of the market etc. And when it hit a rough patch, that was when we said, “Hey, let’s, let’s take a look.” I think they ran a sales process. I think there were bankers involved. And I think they were at a particular time where their stock had come down, so the reason why the deal had a hard time getting there was because the price that we were wanting to pay didn’t match the price that they wanted, as is typical sometimes in these transactions. So we had decided to move on.

We had kind of made what we thought was a rich offer and HomeAway indicated that it wouldn’t work. And I’ll give Brian credit, which is Brian reached out to me. And there was a management kind of a presentation, but the clincher for me was a call that Brian and I had about his company, the challenges and the opportunity that he saw on us coming together. And that’s what kind of, something clicked in my head. And I went back to my team and I went back to Barry (Diller), said “Hey, there’s a place where we can make this happen. There’s a solution space here. And I think it can be a great acquisition for HomeAway and getting that brand to be even bigger.” Obviously we’ve gone with Vrbo now, or Expedia’s gone with Vrbo, but getting that entity to become truly competitive and to flip over in an aggressive way into kind of a technology-driven and transaction-driven kind of a business model is where it is now.

And now looking back on it in a post-Covid world, that transaction has turned out to be better than we could have all dreamed, somewhat by accident. That was an accident that I wouldn’t wish on anyone. But it’s really satisfying to see how well it’s worked out now.

Carl Shepherd: 

You couldn’t pick better people than Dara at the time. Of course, he left and went to Uber. But Dara is just such a good person. And Mark (Okerstrom, who succeeded Khosrowhahi as Expedia Group CEO) is a good person. It wasn’t like you were leaving your team with people who were the devil incarnate. These are all good people who we’d known for years. So it was pretty easy to say, we know that they’re not going to steamroll our people. And besides our best people will all be millionaires.

What I found out at the closing dinner with Expedia. I’m sitting next to Mark Okerstrom at the closing dinner. And Mark said he didn’t know if you knew it, but he thought he had a deal to buy VRBO. I said, really, when? And it was in that November 2006 period when I was dealing with VRBO when Dave Clouse called me. Mark said, I flew a whole team out, we spent two days. We went through everything with Dave and we put together a term sheet and I sent him a term sheet, and I really thought we had it. Then the next thing I know, he calls me and says, you bought it. And I said, really? What had happened was, Mark, I never knew why Dave picked up the phone and called me. All I know is one day Dave Clouse called me and said, would you pay $x for my company? And I said, yes.

Brian Sharples, HomeAway founder:

We had inbound interest from those guys at Expedia. We’d been talking to Dara Khosrowshahi for a while. I think we started all the way back in 2012 with a partnership with them to start seeing if we could put listings on their sites. And so we were familiar with the team. We were doing a lot of testing with them. And so these discussions would resurface constantly. I got to know Glenn Fogel of Booking Holdings pretty well because we’d sit down and have chit-chats with him quite a bit, and as well as with Steve Kaufer from Tripadvisor.

I think up until roughly 2015, as a public company, we had not gotten a firm bonafide offer for the business. I think we had always been pretty clear with people about what value and what price we’d take. So we would say, “If it’s not a 50 percent premium, let’s not even talk about it.” And Glenn Fogel of Booking Holdings thought it was too expensive. And it probably was too expensive for Tripadvisor. And Expedia was kind of always hanging around the hoop.

The genesis of that deal was partly the fact that around that time we were having a number of discussions. There was a number of companies with inbound interest. But we also at that time were getting prepared to make a major move in the business, to move it to a commission-based model from a subscription model. And one of the things that a lot of people don’t realize, as a listing business, we had created this system of tiers that you buy into. So originally at VRBO the search order was based on when you got there. It was first come, first serve. So if you were the first property in the platform, which was Dave Clouse (and his vacation rental in Colorado), you were number one. Right? And then we ultimately came up with this system of tiers, where you would buy in at different levels. We had a platinum tier, and gold tier, and silver tier, and bronze tier. And those tiers are really what helped the business grow revenue massively year by year because people keep moving up in tiers. So essentially it allowed our ASPs (average selling prices) to naturally rise with the demand for people who wanted to be higher up in sort order. And so those tiers accounted for hundreds of millions in revenue. And we were about to go through a process where we were going to wipe that out and move to an online booking system, which in theory was going to be a bigger and more profitable business. But it certainly wasn’t proven. And there was going to be a lot of churn along the way. And so I came to the conclusion, in talking to our bankers, that we would be better off doing that migration under a bigger umbrella. 

I would say number one was that, as a public company, it was going to get ugly. We knew we had to do it. And it was going to be an ugly transition. So we had thought about taking the company private. We thought about a sale. So we were looking into those as options. When we then went out and did some market checks, back to Glenn, back to Steve, back to Expedia, and Expedia expressed a significant amount of interest.

And then I would say reason number two came up, which is in speaking with Dara and his team, we also realized that one of the things we were concerned about, which is that we had never operated a commission-based model before, that a company like Expedia had been doing that for 15 years. And they understood all the tricks to maximize conversion, and all the accounting behind it, and everything else that we were going to have to go and build and learn.

And so whether it had been Booking or Expedia, it didn’t matter. Either one of those had a lot more experience in that business than we did. So we felt: A) We had to do it out of the public eye. B) Somebody like Expedia was going to allow the company to be more successful in actually doing it. And ultimately they came up with a price that hit our objectives in terms of a premium to the price. And we did what all public companies have to do, which is went out to everybody else and said, “Are you willing to top it?” But I think the only one we really were interested in was Booking because we thought they also had the technology and the team to be able to do this well. And they weren’t able to top the Expedia price. And so that’s where we wound up.

We’d spoken to Google over the years. Google’s position was always … And we were a good partner of Google. One of the reasons we had to keep very close, and I don’t know if you know, but Google Ventures was a substantial investor in the company. They had put about $50 million into the business. And at one time actually Susan Wojcicki was on my board, too, for a couple years. Our relationship with Google ended up keeping Google out of the business, which was probably the most important thing. And the reason we convinced Google to stay out of the business, and the reason Google didn’t want to be in the business, is because at that time they didn’t want to get into any business that was customer service centric. They wanted to be in pure digital businesses. And one of the things that we would show to Google is a third of our P&L is service and support. And Google just didn’t want to touch that. That was antithetical to what they were trying to do.

Tobias Wann was HomeAway’s general manager, Europe, from 2011-2015, and became CEO of @leisure group, which was predominantly a property manager, starting in 2015. Oyo acquired @Leisure Group in 2019, and rebranded it as Oyo Homes.

Tobias Wann, then-CEO of @Leisure Group, shaking hands with supervisory board chairman Andreas Wiele. In 2019, Oyo announced its acquisition of the company.  In the background (R) is Oyo CEO Ritesh Agarwal. Source: Tobias Wann

Tobias Wann @Leisure Group: 

In 2015, @leisure came around as a unique opportunity for me to actually become a CEO and run a sizeable company in the vacation rental industry. So, that was an opportunity that I definitely wanted to take on. So, moved the family to Amsterdam from Frankfurt.

So @leisure Group was a different setup and a different size when I arrived, compared to what we ultimately sold to OYO. The @leisure Group was similar to an Interhome or Vacasa. it was a vacation rental management company. When the @leisure opportunity came, I felt, it’s a great moment in time to actually double down on the supply focus strategy and do something that the big platforms are not willing to do, which is literally getting your feet and getting your hands dirty on the operational side. When I came to the @leisure Group, they probably didn’t realize the same potential that I saw, and over the years I’ve been probably doing 10-ish acquisitions of all sizes to grow the supply base, to grow the operational base. Probably one of the biggest, when you look at just the M&A process was DanCenter in 2016 out of Scandinavia, which was an independent company that was listed in Copenhagen. It was the second biggest VRMC brand in Scandinavia. 

We also had some other brands which were more traveler-focused. There was a brand called Casamundo, for example, and we sold it to HomeToGo in 2018. Because it was my very clear conviction that you had, there was this opportunity to actually double down on supply and the one who owns the supply is the one who will be able to kind of survive even if the large OTAs are increasingly fighting for the traveler. I don’t think it is as profitable. Clearly all these platforms — Airbnb, Uber, or whatever, those transactional platforms — they are money machines. I totally get it. HomeAway was a similar kind of platform. On the managed side, that may be a little bit less profitable, but it is still very profitable.

We invested in dynamic pricing and these type of things. So ultimately, we created a business that was much more modern, much faster, growing, much more scalable, and then came Oyo.


I had met Ritesh (Agarwal, Oyo CEO) over the course of the years when Oyo was much, much smaller, at various industry conferences and we always got along well. He was growing like gangbusters in these years, and ultimately we sat down and he said, “I want to create not only hotels, but I also want to have homes on the platform. I have a few homes in India and in Southeast Asia, but not at scale,” and so we started to talk, and that was and of the 2018 and the beginning of 2019. He put an interesting, compelling offer on the table. It was around $400-plus million. 


So the sale was in May 2019. So let’s say we had six months, Covid-free. We rebranded to Oyo Vacation Homes, which I clearly supported. I was never a big fan of the @leisure brand so Oyo made sense to rebrand. So in this first six month, Ritesh and team, very much supported us in our growth plans to double down and basically take market share. We also had started to build up Oyo Vacation Homes in the U.S. We put the focus on Western Europe. We said, Europe and the U.S. There was already some existing business in India. and it was good how it was. We made really good progress, but as you can imagine this investment in growth usually takes time and then we were hit with Covid.

And Ritesh clearly saw he had bought a very strong platform with the @leisure Group. That he could kind of put more resources to and let them just run and that’s what we did. So what happened in the U.S. (Oyo restructured there even before the pandemic) and elsewhere on the hotel side, wasn’t something that affected us nor were we actively involved in. I’m not an Oyo hotel expert but I obviously watched it from the sidelines and our growth was a little bit less aggressive, and more based on the experience we already had in previous years.

In April 2019, a month before Oyo acquired @Leisure Group, Airbnb invested $150 to $250 Million in Oyo

TechCrunch

Tobias Wann:

I think that was always just a financial investment. We used Airbnb as a distribution platform. So we put all the homes on Airbnb and on Booking and Expedia and we didn’t really have conversations (with Airbnb) just because of the investment in Oyo.

I left in August 2020. But if you now look at Europe, Oyo is basically, more or less, entirely only active in vacation homes in Europe. It may have still some hotels, but it’s not the focus.

In 2016, Sandra Brown and her husband decided to take one of two cottages they owned in Muskoka, a popular vacation region about three hours north of Toronto and try to turn it into short-term rentals.

Sandra Brown in Muskoka, Canada in 2021. Source: Sandra Brown 


Sandra Brown, vacation rental owner:

We definitely advertised on Airbnb and we also were on Vrbo and we tried it up for the summer and it was a huge success — wonderful people and a great experience. It was a two-bedroom cottage and we were like, “Yeah, this works. Let’s do it.” And then for a couple of years there, we just rented that two-bedroom cottage. It’s fully winterized, did sleep six people, we had wonderful families, and positive experiences, all was good. And then it got to the point where we had lots of repeat business and we’re full up. We’re having wait lists and it’s booked a year in advance for the summer. And we thought, you know what? There’s a demand here and at this time, well, my husband still has his own full-time job. And I at that time, I think I had a full-time job in the beginning. 

I have a very cool corporate background. I used to manage recruitment for a major bank in Canada and I was in a national role. So I had staff and team all across Canada. So I had a lot of project management experience. and people manage experience and-

But at the end of the day, this is a hospitality business. A lot of people don’t really understand how to do this right. They think they can just throw their property on the platform and off they go, and they don’t really have to think about it, and that’s bullshit. And I have to say, we seem to know what we’re doing. We’re very successful at it. I take it very seriously. This is my full-time job now. And I make good money at it.

Now, first of all, I should say, we don’t get the problems to the extent the Americans do. It’s totally different. The shit I hear on Facebook about Airbnb in the U.S., oh my God. It’s like everyone’s out to take advantage of each other and scam each other. It’s like the Wild West down there. It’s not like that here. 

So after a couple of years of doing this, and doing it well with the two-bedroom, we recognized the demand and we thought, you know what? Our cottage, our family cottage, maybe we should open that up to the public. Maybe we rent that out and that’s a much bigger cottage. That’s a six-bedroom and sleeps 20. So three years in, we rented it to two families. Both of them were fantastic. One of them is still with us.

But anyway, let me just tell you about one of the families. I was cleaning the cottage and I didn’t know this, but my diamond fell out of my engagement ring. And I only found out when I’m driving back to Toronto. So three hours up and three hours back. And then I’m driving home, and I look at my hand on the steering wheel, my diamond is missing out of my engagement ring. Now, do I tell them my diamond is in the cottage or do I not say anything? I didn’t know how to play it. Anyway, I figured, you know what? I have nothing to lose. I’m just going to be honest. I told them the same day. And then by day two, they found my diamond and returned it to me. So I gave them a 100% refund on their stay as a thank you.

At this point I was using Airbnb and Vrbo. And I probably was also using Cottages in Canada by then. That’s a very, very good website. I don’t want the world to know about that website, but it’s a very excellent source. So yeah, I was using Airbnb and Vrbo and Cottages in Canada, and I was booked up so solid that I still could not meet the demand.

So after a couple of years of two cottages, one very large, one very small. I figured, you know what? There’s still demand out there. So that’s when we went to the third, that’s when we found the vacant property on our cottage road. All three of these cottages are stone’s throw apart. And so we bought a piece of land, and we knew the region is what draws these people. I finished that third place the construction rate at time for COVID. It was perfect timing. 

And at this point we had dropped Vrbo, we just didn’t need it. And we were just using Airbnb and Cottages in Canada. It was too complicated, too many calendars and I don’t trust where you sync the calendars. I manage the calendars myself because I’ve had bad experiences with this. 

In 2019, Expedia Group announced that it would begin the process of rebranding VRBO to Vrbo, and that the HomeAway brand would be phased out in favor of Vrbo.

Dave Clouse, founder, VRBO:

They couldn’t buy me. I wasn’t ready to sell (in 2004.) If I had, I am convinced that they would’ve named the combined company VRBO at that point. So they had to come up with a name and that’s when they came up with this name, HomeAway. And for 10 years after I sold, they were doing everything they could to kill the VRBO name and keep the HomeAway name. They wanted to pump the HomeAway name. That’s what their primary branding was.

And to the end, once they sold to Expedia and then Expedia finally said, “Oh, we’re changing the name to Vrbo.” I felt a little bit vindicated at that point. Because we kept telling him (Sharples), “Why are you keeping this HomeAway name alive? No one’s ever heard of it.”

Brian Sharples: 

I think when I first heard that Expedia was going to switch the name to Vrbo, on an emotional level, I felt, yeah, a little bit sad. Listen, this is the company that Carl and I built together, and we built it as HomeAway. And 10 years down the line, nobody’s going to know what that name is. And maybe that’s a little disappointing on one level. On the other hand, I’ve always been kind of a data driven and logical thinker. And the other side of me said, “You know, I think they’re making the right move here. Because VRBO was always a platform that, without marketing support, kept chugging along and chugging along. And back in those days when everybody knew it stood for Vacation Rentals By Owner, today people don’t know. It’s just another acronym.” And there are plenty of companies that are successful with just another acronym, and people don’t really know what it stands for, and they don’t care. And the fact is half the properties are proper management properties on that platform today, and it just doesn’t matter anymore.

flip key founders

Flipkey co-founders (L-R) TJ Mahony, Carl Query and Jeremy Gall at a party in 2011 to celebrate their first $1 million in revenue.

TJ Mahony, founder and CEO of FlipKey, 2007 to 2013

So I was traveling a lot for Compete and I just bought my first condo in the north end of Boston. And I got my first mortgage bill and I did the math and I was paying like $250 a night to stay in my own place, because I was there so infrequently. And so I thought it would be interesting to start renting it out. And so I looked into it and people were posting things on Craigslist, which was super untrustworthy. And then I came across VRBO, and so I posted on VRBO, and I started bringing people in for a few days at a time when I was gone. And I’d get back and there would be a check for a thousand dollars, a bottle of wine, and a thank you card saying how much they appreciated me letting them stay there.

And I was thinking this could be a business. The VRBO experience was pretty horrible. This site hasn’t been updated in a decade. There’s no trust in it and it has no UGC (user-generated content) components to it whatsoever. So you’re just kind of blindly trusting people. If we can build a trust layer on top of this, this would be very, very interesting, especially in urban and primary home markets. So I talked to this kid, my original co-founder Carl Query, who was the lead engineer at Compete, and gave him the idea. So we started working on it and we pretty quickly realized what we were trying to do had a lot of legal implications. And there was a lot of operational complexity. My roommate at the time was Jeremy Gall,and he was a good buddy of mine and he had a legal background. So he loved the idea. So he joined as the third founder.

The first iteration of it was more Airbnb than VRBO. We intended to allow people to rent out their primary homes. And I think what happened is if you go back and you look at the history of Airbnb, at one point, I believe, they took in $100,000 to keep the company afloat. They sold 10 percent of the business for that because the idea was outrageous. Right? We were met with the same skepticism. A lot of VCs (venture capitalists) were very interested, but all very skeptical. 

And it was Josh Kopelman at First Round Capital who said no to me in the meeting. I remember him distinctly saying the problem with your idea is that it fundamentally would lie on changing human behavior. We as humans are used to transacting with each other, but we do not like sharing with each other, he said, and what you are proposing is that we have to start sharing things. I said how much evidence do I have to show you that this is already happening unmanaged in unregulated markets like Craigslist. So people are doing this out of sheer will. Imagine what would happen if you actually created a framework, a trusted environment for people to do this and economics are significant. My other counter was if the economics are significant enough, it will change. People will change their behavior. 

So fast forward. We ended up pivoting a little bit and just saying, no one’s buying into this primary home thing. No one can argue that the second home marketing doesn’t exist, especially these venture capital guys. They all owned second homes. They’ve all rented them before. So there’s no real objections. You could look at VRBO, and you could quickly estimate what their revenue probably looked like. And it was easy to measure the market at the time. This was a potential $20 billion-plus market with no sophisticated software involved.

We started looking at the vacation rental market, primarily second homes and vacation destinations. And we had raised half a million dollars through mostly family and friends, some venture capitalists put in personal money, but they didn’t put in firm money. We went out and started basically building what was VRBO, but we wanted to do it with a trust layer on top. And We zeroed in on building an authentic review collection system and that was our wedge. We decided we are going to make it very easy to collect reviews, authenticate that they’re actually real, that real people who stayed there actually left this review. And then also layer it with reputation management tools to allow homeowners to be able to at least respond to critical reviews and things like that. I know this all sounds super benign and novice now, but what we started at in 2005 when we incorporated, I think, it didn’t exist. So all you would find was on VRBO they had a testimonials page and it was wholly controlled by the homeowner. So the homeowner could actually write their own testimonials if they wanted. We actually started telling people that we are the Tripadvisor of the vacation rental industry, and that helped everyone quickly understand what we were trying to do.

We loved VRBO’s model. But to find a homeowner to individually list on your site is very difficult. You need to find the contact information of a homeowner that has a second home that wants to actively rent it. So that is very difficult to do without breaking laws. So short of that, we started creating a long-term SEO (search engine optimization)n strategy. But in the interim, we needed to sell this product to people who we know how to contact, which was property managers. And so we started scraping the web and basically creating a database of all the active professionally managed properties in the U.S. and built the software for their software systems. And so by building into their software systems, we could actually pull in historical reservation data and collect reviews from people who stayed this year, last year, five years ago.

We were very successful because we started publishing. I think we published the first ever vacation rental research report. And we did it in conjunction with Compete. Compete had a massive click stream database and a large survey panel. So in the click stream, we were able to identify people who have actively rented and also stayed at home, but also owned and rented a home. And we were able to collect a pretty critical sample size to get their thoughts and reactions to what the industry needed. And so we published it. That created a lot of inbound and we just became a well-known sought-after fancy new solution for professional managers. 

We negotiated our deal with Instant Software around 2007. Property managers were the majority of the industry. They all run on software. They need software to help them with payments and taxes. FlipKey was the first one that started building the review collection on top of all those property management software systems. The largest byproduct at the time was a company called Instant Software. It was run by two British guys. Doug Macnaught and Dave Hopcroft. Instant Software controlled a lot of the property management because you have to interface with their software. And those guys had super aggressive tactics. The way that that company made decisions and what it did was bizarre. As a vendor, you felt you never knew what you had agreed on or not agreed on because terms would always change. They would give you access to software and suddenly they’d say, you don’t have access to it anymore This hampered the industry because the pipes were so broken, they weren’t updating the software, and the software wasn’t great. 

Doug Macnaught, co-founder, Instant Software:

The year 2007 was a pivotal year in the Vacation Rental Manager’s Association (VRMA). Prior to that, it had been run by Michael and Rosemary Sarka. They basically ran the organization and they hated vendors. They really did.

TJ Mahoney:

Instant Software basically funded a takeover of the board of the Vacation Rental Management Association (VRMA), which was the largest association. VRMA at the time also had all these weird rules and this big political fight came up. We were asked to attend some of these meetings and to sign things and to wear badges that said no more VRMA. So there was all this infighting, and the software players were very important in it. One of the biggest themes in all of this was anti-VRBO. VRMA was more encouraging people not to use VRBO. The industry was concerned VRBO was disintermediating the property managers. Clients were starting to ask for lower fees because they were booking their own guests and beginning to rely on property managers more for turnover and cleaning, and less for bookings. 

Politically everyone hated VRBO. And you had these independent companies that owned all the software. The other thing was HomeAway would go to Instant Software and say, “You have clients that want to list with us. You have all their listing information. You have the calendars, you have the pricing. Can you just send it to us?” Instant Software would sit there in the middle and say, “It’s going to cost you. And by the way, HomeAway, we don’t even like you that much. So we might not even work with you at all.” So the software companies had the ability to make decisions on their clients’ behalf. It was a very tricky time. 

Rhonda Sideris, founder, Park City Lodging, Property Manager, 1988-Present, VRMA Board Member 1997-2003

Michael and Rosemary Sarka ran VRMA for many years. They were nice people but they didn’t like change. But it was a great experience being a board member. I learned a lot. It was an honor, to be honest. I don’t think I would have the bandwidth now to do it because I’m too busy. But I loved it. And I’ve learned a lot from VRMA and my networking days of VRMA. How to take care of staff and treat them like real people.

Doug Macnaught: 

(The Sarkas) specifically hated Instant Software because we weren’t prepared to put up with a whole load of their crap. So there were rules. You can’t run an event without our permission. You can’t host an event without us organizing it for you. Well, in 2006, we hired a river boat in New Orleans. The VRMA was in New Orleans and we hired the Natchez Riverboat and had 300 people on it for an evening, sailing up and down the Mississippi River, free food, free booze, free everything. It started 10 minutes after the last session of the VRMA and everybody that went had an absolutely great time. The next year they came and said, “Right, we’re throwing you out. We are expelling Instant Software from the organization. You broke our rules.” So we sued them and we were back in.

So the following year in Phoenix in 2007, there was Alex Risser, who ran a company called Outer Beaches Realty. And Steve Trover. They engineered, along with a select vendors, a save VRMA campaign. And the save VRMA campaign’s purpose was basically to oust Rosemary and Michael Sarka from the organization, put in new professional managers, and run it like a professional organization. We bankrolled that. We and a number of other vendors basically gave them a commitment that said that if you create a sponsorship, we’ll pay you $50,000 a year upfront for each one of the different categories. And it’s now their gold sponsors. That’s the original formation of that. Well, what that meant in 2007 was that the organization changed quite significantly.

TJ Mahony: 

So Tripadvisor had called us in 2007 and said they found our research report, and said, “We’d like to talk.” So we were contacted by a number of folks, corp dev people at Expedia and Hotwire, which was all under the Expedia umbrella, people at Booking. The research report got out. But it was the Tripadvisor inbound that I felt was the most interesting because they were down the road. And remember, at that point in time, Tripadvisor was one of the hottest things going. It was the largest travel site in the world. Revenues were growing, the employee count was doubling, it was the darling of the travel industry at the time.


And so we took that meeting in the Tripadvisor board room. Steve Kaufer and I are friends, and we’re definitely respectful colleagues. And I just remember, he called us in and he said he read some of our stuff and wanted to hear what we were doing. Steve said Tripadvisor was going to get into vacation rentals, and it was interesting that we call ourselves the Tripadvisor of vacation rentals. 


I remember Steve saying, “What’s to stop me from just doing this?” I took him through the logic of why it would take them a decade to get enough reviews. So we started there and then he asked for a demo and I said, “This is intimidating. You guys just said you’re going to build this. Your name is Tripadvisor.” I remember Steve pushes back in his chair and he says, “I have a checkbook. Do you like checks?” And so I said, “Yes, I do like checks, but tell you what, give us 30 days. We’re still building this thing. Give us 30 days. I will come back in. I will take you through it. I’ll just trust the situation. And if there’s a way for us to work together, we can discuss that. And at a minimum, we can learn from each other hopefully.”


I think at that time it was Tripadvisor’s intent to invest in us, not an outright acquisition. And so in parallel, what was going on was HomeAway had raised money and other listing sites were getting aggregated by HomeAway. And so we were paying attention. And then all of a sudden, HomeAway raises funds and acquires VRBO. It was at that moment where I felt like we were beginning to look down the barrel of a shotgun where you had this well-funded entity being run by professionals that just acquired all the assets.


We were integrating with all these software providers that had very legacy code. It was very messy. There was a lot of politics. There was nothing to be done quickly. And then Tripadvisor had this massive asset of traffic, and if they decided to turn on a vacation realm switch, it would really challenge our market position. So we were interested in keeping that conversation with Tripadvisor alive. Airbnb was not even a thing at this point. 

We came back 30 days later. And we walked through it. I explained strategically why we were starting with property managers. We had already acquired 60,000 properties. We had solved the supply problem. We had solved certain data problems. We had not solved the demand problem. We needed traffic. Steve said we have no supply. We have no infrastructure for this. We have a ton of traffic. So do you want to work together? 

Remember at that point, TripAdvisor was owned by Expedia. So we went through a negotiation. So we started going back and forth, corp dev and Expedia was in contact with us. And there was one last meeting, and it was at Steve’s house on a Sunday. I remember sitting down with him at his table and we talked about the industry and I think he just wanted to know me a little bit better. We went into his garage because we had to go pick up his son for something. I’m six feet, but he’s about a head shorter than I am. So his garage is really low, and I ran into the garage door, like carousel thing. And split open my head.


I bled for this deal. And so in the end we negotiated with Expedia corp dev, we negotiated a strategic partnership and I don’t even know if I’m still allowed to disclose those details, but more or less, they took a majority ownership in May 2008. We were able to take in about $5 million of capital to build the business. In exchange, we were given a certain level of exclusive rights to power vacation rentals on Tripadvisor and to recognize all the revenue that we were able to take from that. So we continued running Flipkey, but we would also provide a content API, basically an API to power a Tripadvisor vacation rental experience and to work with their team. The idea was to do that for four years and then we had mechanisms in place where under a strict framework, fair market value would be determined and they would consume the business.


For me it wasn’t the ideal deal that an entrepreneur is looking for because you want to be as independent as possible. But this HomeAway situation was very real. I will start out by saying Carl Shepherd and I ended up being somewhat lifelong friends. We did not speak for several years. That man plays tough. We had been contacted by them. We had legal threats made against us for very benign things that had occurred. They were just playing tough in the market. And it was our getting hooked up with Tripadvisor that helped neutralize the market a little bit and back them off of us a little bit, which was great. 


There was a company called Zonder out of Utah that had some VC backing. It’s dead now. They did something we had considered, but we thought this is going to cause problems. I published an article about it. They were sending fake inquiries on VRBO and getting the owners to respond back so you had their email address. They were then scraping all their content off of VRBO creating a listing on Pick, Pack, Go and then would send you an email saying congratulations, you have a listing on Pick, Pack, Go. Here’s your email and your username. It was so blatant that you could still see the VRBO watermark on all of the pictures. So they had done that to my listing on VRBO.


HomeAway went right after them. Zonder took it all down. They apologized, but it was too late. The business never got funded again and shut down. A lot of people were starting to come in because they saw how weak, how ugly VRBO was. I think they all underestimated how valuable the Google ranking assets were. There was a lot of roadkill in the industry.


Tripadvisor was very important part of our history. I have lifelong relationships there, but I would say that there is a case study. Strategic deals always look so good on paper. They make so much sense. And the economics and everyone assumes that these outcomes are going to be fantastic. I hypothetically could have competed much, much more aggressively. But in the end, the real assets ended up being HomeAway and Airbnb in the end.

Going back and looking at it, there was Steve Kaufer, who was one of the smartest guys I’ve ever met. I don’t want to come any of this to come off as criticism, because again, everything made sense at the time. But I sit as a venture capitalist now, and I fund brand new companies and entrepreneurs that have very little resources and I see some of them turn into multi-billion-dollar companies. The reason that tends to happen is that they break things and they ignore principles and they ignore the way that things have been done. They always figure it out. And they have the independence to make very aggressive, independent decisions. When you start doing these strategic deals and stitch together these assets, and it is not the main reason that they try to put it under the TripAdvisor umbrella brand. But that’s one thing where internally there, there’s the perception that this brand is worth so much money and so much trust. But it wasn’t even worth making arguments to build a mobile device that allows managers to manage from the Flipkey app because it just couldn’t get done. You start making decisions within the construct that your given. 

Kim Rubey, Airbnb head of communications, 2011-2016: 

In the 2012 timeframe, too, was when Wimdu was on the rise. It does feel like ancient history now, but that kind of playbook had really impacted Groupon and other companies that wave right before us. It was two brothers based in Germany. I think they created eBay Germany, that eBay then acquired, and then gained some notoriety because they did a Groupon clone that, if I’m remembering correctly, Groupon wasn’t able to overcome. “Oh, gosh. Are we (Airbnb) going to have to work with people who are trying to clone us?” Ultimately, Airbnb and community-based travels is such a different enterprise, and Wimdu wasn’t successful at all. But I think moments like this really bring the team together in a super meaningful way. So there was that sense of urgency, like we really need to over-deliver and show that our approach and our methods our can be successful. Again, in hindsight, the company has gone through so many different evolutions. The Wimdu challenge, it doesn’t feel as existential as it did in that moment.

Eric Breon Vacasa CEO at Skift Tech Forum 2019 speaking with Dennis Schaal

Eric Breon (left), co-founder and director of Vacasa, appeared at the Skift Tech Forum in Santa Clara, California in 2019

Eric Breon, founder and CEO Vacasa, 2009, and currently director

I loved vacation rentals as a consumer. I really enjoyed staying in them, having that living room to gather with friends and family. Having a kitchen to cook meals together. I really valued that, but it was painful finding a vacation rental at the time. Online booking was relatively uncommon, especially on the rent-by-owner segment. It was just painful to try finding something. I’m an analyst at heart, so I’d make my spreadsheet. Here’s the comparison of all these properties, this is the perfect one, here’s how much it would cost based on the great description. Then I would call to book it, and they would say, “Oh, that’s booked.” And I would say, “But the calendar says it open.” “Oh, we never update that calendar.” And then I just put it on the list, and it turns out that all five of the ones I attempted to settle on, none of them were actually available. The one that was available, “Those rates aren’t correct, it’s actually twice as much.”


It was just a painful experience, and so a lot of my initial goal was to make vacation rentals as easy as booking a hotel. I wanted to bring that ease and simplicity. So Vacasa initially started as a booking service. But, early on we had a lot of trouble with operations, for things that we weren’t officially responsible for, but since it was our customers showing up at the house, we were responsible. Even though it was the owner’s responsibility to make sure that the home got cleaned, when our guests showed up and that home was dirty, that was our problem. We were really a channel manager, early on, for independent owners. 


So, pretty quickly, we transitioned to full-service management, initially largely just so we could really take care of those operational challenges. If we’re managing the housekeeper, we’re confirming that the housekeeping’s done, clean houses is no longer a problem. If we’re the only one taking bookings for the house, bookings aren’t a problem. Pretty quickly we made the transition to that full-service mode. Cliff Johnson, Nick Tostenrude, and myself were the early employees there. I did a super random Craigslist ad, with all sorts of randomness. I was working on different projects and was basically just looking for interested people to collaborate with. Nick Tostenrude was involved just in the first year of Vacasa. He ended up going on to get an MBA from Oxford and had a big job at Amazon. He went his separate way, but he was definitely key in those early months.


At the time, Nick and Cliff worked from my dining room while I consulted for a credit card company to get money in the door to pay the bills. I think the first $120,000 all came from a consulting contract with my prior employer. I think it was that winter or that spring when I quit that consulting job so I could start showing up with them in the dining room every day. 

We were all based in Portland.

We started building a shadow system. It also didn’t have a lot of the functionality we were looking for. After a year we realized, we’re not actually using Escapia to do that much anymore. Most of this stuff is just in our shadow system. Really at that point, in 2010 or 2011 it was only powering our front end so we built a new front end and we transitioned completely off of Escapia.

Another big point in the early history was initially we were just focused on places within driving distance from Portland, Oregon. I think one asset starting out is that from our start we were in a market where vacation rentals weren’t a thing. Portland considered them to be a commercial use, banned in residential areas, and so we weren’t allowed to do them in our location here. For that reason, we were focused on the Oregon coast. We were focused on central Oregon, these vacation rental communities one, two, three hours from Portland. In hindsight, I believe it was a huge advantage for us that from our start we were figuring out: What can we do remotely, and what do we need locally? 

I think we were one of the earliest companies to use direct mail, and so we really appealed to people that bought their vacation home in 2005, feeling so smart because it was just going to go up 20 percent here every year. The equity would pay for their retirement, but then prices were down in a lot of these communities 30-40 percent They haven’t used it in six months, and yet they’re paying the tax bill. They’re paying for the new roof. And so the timing of starting right at the end of 2009 when housing prices were depressed, it really set us up to bring new inventory into the market.

A big part of our early value proposition was we did guarantee to homeowners that if they were currently with a different manager, we’d increase their net income by at least $5,000 per year, and if they were currently owner-managed we guaranteed they’d make at least as much, even after our fee. Combined with that, we did have good operations. We’d be in every little beach town going up and down the coast, we’d have a lot of spare capacity that could move up and down the coast. So, if somebody was out sick, or if somebody was on vacation, we could cross-cover. That really gave us an advantage over smaller competitors that maybe only had one maintenance person, so if that maintenance person was out, they just wouldn’t be in a position to respond.

One of the first big points in the history of our company around 2011 was we had an owner on the Oregon Coast who also owned homes in other locations, like Tahoe, so I think we were managing two properties for him on the Oregon coast. He was impressed with the service we delivered, both on the service side and the revenue side, and he said, “Hey, you guys are so much better than everyone in Tahoe, I’ve tried them all. You guys should start up in Tahoe.” So we hired someone to do that off of Craigslist. We didn’t meet her in person, we just did a Google Meet, I think. Then Cliff trained her over Google Meet and over the phone, and within a few months, we were adding 10 homes per month in Tahoe, and had a great Tahoe operation. That was a game changer for us because it made us realize that hey, if we can compete in a market like Tahoe that’s a thousand miles from our home office, we can do this everywhere. And so, from that point on, we started a pretty aggressive approach to new markets.

I forget the exact year of our first portfolio acquisition, but it was well after we started launching new markets organically. Our first acquisition was opportunistic. It was an inbound from someone in a market that we were already in. Their spouse had significant health issues, didn’t have long to live, and they just wanted to be able to walk away from their business. They wanted to spend the six months they had with their spouse, and so they were really just looking to get out as quick as they could. We agreed on a price, and we bought the company from them, took over the operation, and we realized, hey, that went pretty well. Everything fit really well into our system, and so that’s what really opened our eyes to the potential of portfolio acquisitions.

We eventually moved to our default new market entry strategy being acquisitive, buying someone who’d seeded the market for us. 

Chip Conley at Airbnb Open in Paris, 2015. 

Chip Conley, Airbnb head of global hospitality and strategy, 2013-2017

There’s a very interesting quote from Robert de Niro in the movie The Intern. He says, “Musicians don’t retire. They quit when there’s no more music left inside of them.” I was in my early fifties. I knew I had music inside of me, in the form of wisdom or whatever.

I had learned some things along the way. Entrepreneurship, leadership etc. But I wasn’t sure who I wanted to share it with or who wanted to actually learn from me. 

And then, one day in early 2013, about two-and-a-half years after I sold Joie de Vivre, I got an email from one of the people on Brian Chesky’s team. And then it was Brian. They wanted me to come in and give a speech on hospitality innovation at Airbnb headquarters. Airbnb had about 125 to 150 people. Their headquarters literally was a 12-block walk from my home. I didn’t twice about it. I didn’t really know anything about Airbnb. I thought they were related to couch surfing. I truly, at that time, thought they were. Isn’t your parent company couch surfing?

I went to their headquarters and I was surprised that, with 120 or 150 people in the company, about 100 of them showed up for the talk. The talk went well. There was such a curiosity about hospitality because there was not one person, not one of those 120 to 150 people who came from a hospitality background or the travel industry. No one. Zero. I was this weird, exotic animal that was coming in and talking about an industry that they were in the very early stages of disrupting. And then, Brian pulled me aside afterwards. He said, “Wow, Chip. That went really well.”

And I said, “Well, that’s great. Thanks. If I can be helpful in the future, just tell me.” He said, “Well, you can be helpful now.” That’s when the wining and dining of Chip started.


The intent of the speech invitation was two-fold. One, was to whet my appetite. Two, was to see if my persona, my personality, what I could offer, felt right to the people in the company. The average age in the company was 26. I was 52. Can this 52-year-old, this Boomer, come into the land of Millennials? This hotel guy. The arch enemy. So I think it was both testing me out, but also helping me to see what they were all about. That’s when I started talking to some of my friends. Who are some of my friends? Well, there’s a guy named John Donahoe. He’s now the CEO of Nike. He was the CEO of eBay at that time. I reached out to John and I said, “Listen, I know you’ve been mentoring Brian. Brian really wants me to come in-house and be his in-house mentor. But also be in charge of strategy for the company, and business development and all the hosts globally. I said, “I’m a little cautious.” He said, “Chip, trust me. Airbnb will be worth more than eBay.” I was like, “I don’t know about that. You’re not a hotelier. You don’t understand. How can they convince people to stay in each other’s homes?”

The use case when I joined Airbnb in 2013 was Millennials on a budget, traveling to one of 20 major urban markets in the world. And so I wondered, “Can it expand and go mainstream?” That was really my job. To help to figure out how to do that. 

Then it was Brian coming over to my house, my cottage in my backyard. Having me come over to the office and meet some of the key people. I was going to start on April 222013. And so, it was about a month and a half after I gave my speech. The night before I was starting, we hadn’t clarified what I’d get paid or how much I was working. Or how many hours a week I’d work. Literally, this Sunday night, he came over to my house. I cooked him dinner. We had dinner and had a four-hour conversation. I told him I’d give him eight hours a week. We virtually arm wrestled. We didn’t officially arm wrestle, but he got me to 15 hours a week. I said, “You don’t have to pay me anything. Don’t pay me any salary. Just give me some stock options that actually vest in six months. Not four years.” And so, that’s what we did. It was not a lot of stock. I think it might have been 10,000 shares of stock that would vest in six months.


And so, on Monday, when I showed up at the office, it was 15 hours a week. No salary. 10,000 shares of stock that would vest six months later in October. My role was not defined. First and foremost, it was to be his mentor. Secondly, I was to help set up a hospitality function in the company. It was not strategy at that point yet. It was not business development. It was not business travel. It was not any of those things. But it was just that.

And so, long story short is within three weeks, we had a meeting and I said, “Hey, Brian. That 15 hour a week thing ain’t happening. I’m working 15 hours a day.” He looked at me and he laughed. He said, “Well, are you surprised?” And I said, “No, I’m not surprised. But I think we need to talk about compensation again.” And so, at that point, I started earning a very modest salary. I was just given a lot of stock. A lot of stock. I never negotiated any of it. It’s just like, “Here.” I never asked, “How does this compare with anybody else?” But it was a lot. It was a lot. Long story short is, within a month, I was in that role.


We did not announce publicly that I was operating the company full-time until September.

It was partly because we wanted to make sure that Brian and I had a good rapport. Because think about it for a moment. Brian was 21 years younger than me. He was the CEO of the company. I’d spent the last 24 years being CEO of my own company. There was a real risk that we would actually have some friction and Brian could feel intimidated by me being around or felt like I was trying to get his job. But actually, we didn’t feel that. And so, in September of 2013, that’s when we started talking publicly about the fact that I was in the company. But we did not talk about it for five months.

VRBO started in 1995. Now, all it really was, was an online site; it was like a bulletin board. They were way ahead of Airbnb. In the sense that, they could see the need and market for a clearing house. A marketplace. But they really were just an advertising vehicle. And then, what came along is Airbnb, which said, “OK. Well, why don’t we have payments go through our platform? Why don’t we actually create in-house guest and host reviews, so you can build a reputation over time? Why don’t we actually go out and pay for photography of listings?” In the early days, when I joined I said, “Why are we spending this much money on photography?” And I realized, for some people, it felt good to have a professional photographer come in and shoot their home. And so, the Airbnb design experience, the UX/UI was so much better. 

I was probably traveling more than any other Airbnb exec. I went and did a tour. It was the world tour. 22 different locations. Everywhere from Dublin to Florence and to Seoul, Tokyo, and Sydney. I came back with my top 10 list and said, “This is the thing that our hosts need and want.” I got to tell you. I’ll never forget that meeting. There’s a room at Airbnb called the Dr. Strangelove Room. And it’s just a circular conference room that’s sort of just crazy. I was presenting and all three founders … I think they were like, “Wow.” They at that point had been running the business for about four or five years. They were very close to the host community. They really were. And yet, because they were founders, there were a lot of things maybe the host community wasn’t going to tell them. And so, I came back with a lot of great information. Brian would tell you this. He would remember this. Joe Gebbia would remember it. Nate would remember it. When Chip came back from his world tour with all this stuff.


I don’t feel like I can divulge what were the top 10 things that were, but it had an enormous influence. And it was during that time that Brian said to me, “You’re in charge of strategy for the company.” Just like that, and I said, “OK, fine.” Given that I’m not a tech guy, being the head of strategy for a tech company is like, “Well, that’s interesting.” 

I said the following things. “If you want to be a hospitality company, we have to pay occupancy tax.” We have to do that. It’s a requirement. It’s unfair for us not to. It took a little while to get there, but we got there pretty quickly. And then, also we need to be regulated. This didn’t go over all that well, but over time, people got it. We needed to be regulated to legitimize short-term rentals in urban markets. The legitimacy of vacation rentals was already there, but nobody had created urban short-term rentals. And it turned out to be the dominant part of the business. 


Then, we needed to go out and say, “OK, who are some partnerships we can make?” Whether it’s American Express because that’s a well-respected brand in the travel space. How do we build a business development relationship with them? How do we actually create some relationships with hotels? And so, Arne Sorenson of Marriott. God rest his soul. What a lovely man. I invited … This was fun. It’s fun to talk about these things.


Actually, let me say, we did an offsite in September. In New York, in 2013. We took our top 12 people. We had 30 strategic initiatives as a company. No one, including Brian, could recite all of them. And so, I said, “We’re going to have four for 2014. We are going to have only four strategic initiatives.” Every single person in this company needs to be able to recite them, and we all need to know how we’re actually having an influence on them. And so, we went to New York for a three-day offsite with the leadership team. We came up with our top four. But going into 2014, we also needed to have that credibility. And so that’s when I started reaching out to the hotel industry in a more significant way. 

By 2014, the ridiculing was starting to happen. Sometimes from hoteliers. Definitely, hotel associations. The association thing hasn’t stopped. For sure. But the hotelier thing has generally stopped for the most part. Destination management organizations. They don’t like us if we’re not paying hotel tax. People are choosing, in Austin, to stay in a home when South by Southwest is happening, and the hotels are not filling. That’s not good. And so, that’s why we need to pay occupancy tax. We also have to build a relationship with them. 

Brian Sharples:

Back in the early days I remember that Marriott in particular had strongly reached out to both Booking and Expedia, and in no uncertain terms had said if you get into this (vacation rental) business, we may not be on your platform anymore. And I knew that because I think that started with a call even the first time I’d met Rich Barton. He said another problematic issue here was that the hotels did not want to see us get into that business. And so they very much did view it as competitive. In fact, when we were doing the tests with Expedia, Aman Bhutani who was running it at the time, his biggest issue was in fact cannibalization of the hotel business.

So there was a fairly sizable hotel lobby, and a lot of money getting funneled into politicians. Eventually, it was interesting, when Airbnb came along, all our issues were in vacation markets, and we usually would prevail pretty quickly because their economies were so dependent on vacation rentals that no matter what the lobby was, they weren’t going to ban it or outlaw it. When Airbnb came along, in cities across America, they created a bit of a legal firestorm. We had properties and cities as well, that we had to jump into.

Eventually, Carl and Brian Chesky spent a lot of time together because we did go from competitors to partners on the legal front to help fight that together because the lobby was so strong from the hotel groups in New York City, and San Francisco, and LA, and places like that. So they were pretty active in trying to squash the industry. No question about it.

Conley meets separately with the leadership of Marriott, Hilton, Hyatt, Starwood, InterContinental, Best Western, and Accor starting in 2014.

Chip Conley:

And so, part of my role, as Brian would call me, was the Secretary of State of the company. When it came to the hoteliers, it was like, “OK. I’m going to do something totally weird.” I am going to invite Marriott, Hilton, Hyatt, Starwood and InterContinental to Airbnb headquarters for us to do a two-day intensive with them. To teach them about short-term rentals, about data science, and about Millennial travel habits.


Well, we did them separately, mostly in 2014. Here’s the story of those five. Hilton showed up and Marriott showed up. Hilton’s Chris Nassetta showed up separately. Three of his senior leaders showed up. His top three people showed up and did a two-day with us. And then, Chris came separately on his own. We did the same thing for him. Marriott came. Arne came and his senior leadership team came. Four or five people. Arne came multiple times. And I’ll come back to Arne in a minute. Hyatt did not come. Individual Hyatt leaders came, and I went to Chicago and met with Mark Hoplamazian in Chicago. InterContinental did not come, but I went to London and met with the CEO at that time. Starwood came and that was crazy. The CEO was Adam Aron. He’s just a big clever thinker. But he wanted to do a deal with us. He wanted to do something that was going to put Starwood on the map as the Airbnb partner. The other people we met with was Accor. For Accor, I went to Paris and met with Sebastian Bazin. We talked about how we could work together. Six different companies. It’s not like I didn’t talk to other people. I talked to David Kong at Best Western. I had lots of conversations.


But in terms of in-depth conversations about, “Could we do some kind of partnership?” We had those conversations. The reality was, in most cases, it was just me putting out the red carpet to say, “We want you to understand who we are.” As Brian would say, “It’s hard to hate someone up close.” And so, that was an important thing we did, and I actually think probably one of the more important things I did during my time at Airbnb. All of this was quiet. We were not talking about any of this. 


Starwood was very interested. They really wanted to do something. But Starwood was in a somewhat precarious place as an organization. And so, I can’t really talk about it. Because I probably signed something along the way. But it was Marriott that we went into very deep conversations with and came that close. Let’s just call it distribution for right now. It was a big partnership. It was a very in-depth partnership. The lawyers were papering it. We’d gotten up to all the business points. Three weeks before it was going to be announced, Marriott decided they had cold feet. That was probably 2015, at that point.


But I say that to say, ultimately, Marriott moved in the direction of creating their own Homes & Villas product, which is higher end. It’s understandable. I’m sympathetic to the hoteliers.

But I think what I want to just say is Arne Sorenson from Marriott really got Airbnb. Yes. He got the threat, but he also saw the opportunity. I actually think none of those folks, at the end of the day, none of those companies, or the CEOs of those companies, publicly were bashing us in 2015 or beyond. They were generally relatively neutral. Or in some cases, like Chris Nassetta would say, “Their customer’s not our customer.” Now, Arne believed, “Their customer is our customer.” And that’s the risk. Arne saw more risk than Chris did.


Yes. behind-the-scenes, they may have been funneling dollars to the AHLA (the American Hotel & Lodging Association) to fight Airbnb. But we also had face-to-face meetings with AHLA in their headquarters as well as our offices, to try to broker some kind of rapport. That never really went very well. The meetings were civil. But quite frankly, why does a union exist? A union exists sometimes because the way they can portray the employer is such that you need someone to facilitate that relationship between the employee and employer. Similarly, AHLA exists partly because Airbnb and short-term rentals are the bad guys. “We’re here to fight them. Not to facilitate, but to fight them.” And so, in some ways, it created even more of a reason for being for AHLA.


I worked my ass off 80 hours a week and I was on the road all the time. And it was hard. Because the company was growing so fast. Airbnb’s perspective on what we could do and what we couldn’t do was evolving over time because of regulatory issues. But I would say 2013 was strategy and building a leadership team and rapport. 2014 was really making that leadership team strong. That was part of my role too. I ran the offsite retreats for the leadership team, generally.

It was also to build relationships with hotel companies and building the standards. Saying, “Hey. This is what we’re going to give you as host, and here’s what we need from you.”


2015 was building quality. Actually, frankly, quantity and quality of host listings. I would say 2015, to me, was one of the high-water marks of the company. The company won an award through Glassdoor of the Best Employer in the U.S. And there was a really strong culture.

At that point, frankly Airbnb might have been the hardest job to get in the tech industry. Everybody could see the promise of it. The numbers were looking good. But 2015 is when, frankly, we went from ignored to ridiculed to fight. And so, 2015 is when it became more clear on a mainstream basis. Airbnb is not going away. For some people, this is a cancer. We need to actually figure out how to … That’s the year Chris Lehane was brought in. And it’s the year that LT, Laurence Tosi, was brought in as the CFO.

About Chris Lehane, I would say that what we could see is that we needed someone who could organize campaigns. Organize political campaigns in the cities in which we needed. What a complicated business. It’s not like there’s an international or a national organization that you go to try to get your legislation through. In some countries you can, but in most, it’s very localized.

So being able to create a global political campaign, as well as be a tough guy. Chris could be a tough guy. He’s charming at times, but he was oppo research. That’s what we know about Chris.

But Chris is a good guy. I would say Chris had a good impact in helping to marshal the resources. Now, all of a sudden, Airbnb starts spending an enormous amount of money on policy and lobbyists during that time, as well. I can say back then the amount that was being spent was huge. 2016 was an interesting year. It was a year where I could see that for me, on a personal level, it was the year that I just knew, “I’ve been here to help guide the early rocket ship. Help it become mainstream and be the Secretary of State.” But now, a number of other more senior executives are here that we’ve brought in. I knew that by January 2017, almost four years into my time, that I would move from a full-time leader to being a strategic advisor, which I was for three and a half years till June 2020.

Long story short is 2016 was a year where I think it was really a matter of making some really tough decisions. How much do we want to get into traditional vacation rentals? We know that the Airbnb narrative has been, “It’s a way for people to make money for extra space they have.”

Typically, it’s their primary home. Or it’s their cottage in the backyard. Vacation rentals in the secondary home market was a market that in some ways, for some people in the company, was sort of like, “Ew.” There was a physical rejection to that kind of business. 2016 was a complicated year because it actually was, “OK. How is Airbnb going to grow? Are we willing to grow in a lot of different directions? Including, potentially, in the luxury market?” 2016 was the year that we spent quite a bit of time building a relationship with this Montreal-based company, Luxury Retreats. And then, LT pulled the trigger on that purchase (which closed in 2017).

Laurance Tosi (left) speaking at Skift Short-Term Rental Summit in New York in December 2019.

Laurence “L.T.” Tosi became Airbnb chief financial officer in 2015 

Luxury Retreats would curate the homes and all the homes had management within them. It was a very high-end excellent experience. And so we bought that because one, Joe Poulin, the founder, was an incredible entrepreneur and we thought he would add a lot to the management team. Two, we thought they had a really great business model and a great offering. And it clearly had loyalty. It helped us upscale Airbnb into a more serviced home-type environment. And actually, HomeAway bid on them as well. We didn’t know that at the time. But we were both interested in buying them. We both made offers. I knew there was another bid, I didn’t know who it was. And we both made offers and ultimately Joe sold to us and now that’s still a big part of Airbnb.

Chip Conley:

Luxury Retreats was acquired. And then, that’s when Brian started thinking, “OK, well, we have this Luxury Retreat product, which is really expensive. We’ve got our Airbnb product, which is generally more moderate. We need something in between.” The in-between product would be Airbnb Plus. Now, why was there a need for Airbnb Plus? There was a need for it, partly in the business travel market, which is something I introduced to the company … How do we go out and have Airbnb for Work? Business travel? As of three or four years ago, we had, not a million people, but over 1 million companies that had signed with a corporate account. There was an element of, “OK, those folks want something that has got the appeal of an Airbnb,” because a lot of these people are doing longer stays, but they also want something that’s got some assurances about quality standards and minimums of what you can expect there. What’s the minimum internet wi-fi standard in that Airbnb Plus? That was the theory. You have your core business, which is the Airbnb marketplace. You have Airbnb Plus, which is very vetted. And then, you have Luxury Retreats, which is the highest end.

We started to build a relationship with hotels. Ultimately, it led to the HotelTonight acquisition in 2019. I was the strategic advisor, but I was definitely not full-time. It was an interesting acquisition. It was really pushed hard by Greg Greeley, who was in charge of homes. He pushed hard for it. I was a little more cautious on it, personally. But I think one of the key challenges for Airbnb is: Do you want play on the Booking.com playing field? And if you do, they will beat you. Or do you want to create a new playing field? When I say a new playing field, it’s what can we do better than Booking.com? There are lots of things. 

Glenn Fogel, Booking.com and Booking Holdings CEO: 

I guess that’s a compliment. Thank you. Chip’s a good guy. A Look, I think we all, if you look in the industry, and you’ll see everybody recognizes that it’s important to continue to offer more services to the traveler, to convince them that whoever it is provides the best experience for that customer. We all know how frustrating it is to travel, and just staying in one area is clearly something that most companies have recognized it is something you want to expand out. Look, Expedia has been doing a lot of things for a long time, Trip.com has been doing a lot of things for a long time. We are now doing things differently than we did in the past. Everybody recognized that. And believe me, I just absolutely as a traveler am frustrated when I don’t have a single point of contact when there’s a problem.

Chip Conley: 

What’s our playing field and how can we shift the traveler mindset to our playing field? Experiences came out of that along the way. Experiences was never going to make a lot of money, even though Brian thought … What it did was it created a more holistic relationship, customer journey. It also gave us a lot of data on our most active customers. Such that over time, how we could beat Booking, which is to actually say, “Hey. We know you’re going to Paris for a week. You’ve booked on Airbnb. We also know you love jazz. You’re a vegetarian. You are fascinated with history. Here’s a sample itinerary for you for the week.” Including some Airbnb experiences. But also, based upon our data, we know who’s playing in jazz clubs and stuff. And so, Booking will never do that. They’re not a lifestyle brand. That’s for sure. Airbnb could become a lifestyle curator. The moment you become a lifestyle curator, you are in the lofty elevations of Netflix and Amazon and Spotify. Because those three companies are so good at knowing you that they can be a curator of films for Netflix, what you buy for Amazon, and what you listen to with Spotify. For us, it could be where you travel and what you do. We could be the fourth in that list. 

Glenn Fogel’s Booking Holdings has been working for several years on the connected trip, a strategy to tie together various parts of the journey so inconveniences and customer service issues are kept to a minimum.

Glenn Fogel:

Then I have to put my same information into many different vendors to book something. There’s nothing more frustrating to me sometimes than I do one thing, one transaction, and I then do the next one, but I had to start from the beginning. Or even worse, there’s a thing you can’t even, it’s hard to put stuff on hold just to see, because many things, a lot of different things happen at once. Got to do the car, got to do the flight, got to do the accommodations. Is there availability of the ones I want for each of those things? And can I put that on hold for a while until I make sure I get the other one or not?

Chip Conley: 

On the three Airbnb co-founders, all three were very involved. Brian and Nate are exact opposites. Literally, exact opposites on Myers-Briggs. The exact opposite. Brian’s an extrovert. Nate’s an introvert. Brian’s intuitive. Nate is a thinker and analytical. And so, I’m very proud that in 2014, when we were going through our process of building that leadership team and I was running the offsites, I found a way to create a bridge between Brian and Nate. Because they talked different languages. But then, they started to realize, “Wow. There’s something we can do together.” Sometimes they hit heads because they have a different perspective. I think they’ve seen the value of each other. Joe is amazing. Joeis the soul of the company, But Joe and Brian have more in common with each other. Where I think Joe is really helpful was when Brian was getting too much focused on the business and not enough focused on the culture. The intangibles. The employee culture. The host love. The website magic. What Joe did often was take on initiatives that were longer term. 

Airbnb’s challenge, for the last five years or so, has been a supply not a demand challenge. Therefore, meaning there are not enough listings and there’s more demand than there are listings on average. That means hosts are really important. Basically, two years ago Airbnb sided with guests over hosts in the pandemic around getting people’s deposits back. But then, Airbnb shifted and took a big financial hit for paying out to hosts things that the guest was getting. The guests got their refund, and then the host got their money too. Guess who paid the price? It was Airbnb corporate. 

Sandra Brown:

God, Covid was a complete disaster. So first of all, every time the government will shut us down or put restrictions on or reopen us. It would cause the immediate flurry of activity changes, changing my calendar. Because my philosophy was I’ll just take a booking. If they shut me down, then I’ll cancel the bookings. But I’m going to book in the event that they don’t shut me down. And so I had to send out, God, at times I thought I was going to go bankrupt because of the amount of cancellations and refunds. I have a business account, and I always keep $30,000 in my bank account. And I’m in one year, one calendar year, I’ve lost like a $100,000 in revenue due to Covid over various calendar years.

Airbnb’s refund policy was a disaster. Well, they changed their policy so much. It’s hard for us to keep track of their changes and they make these unilateral changes without even asking us. Who does that? 

No, hosts have never been the backbone (of Airbnb). Listen, here’s the thing. I travel with Airbnb, I stay in Airbnbs, both as a traveler and a host. At the end of the day, they charge more money to the traveler than they do the host, like double. So look at the business model. If you’re charging the guests twice as much as you’re charging the host, who is your customer, really. It’s obvious, by the way, they structure the Airbnb fees. There’s no doubt who their real customer is. It’s the guests because they charge them twice as much. You can’t serve both sides equally, … so one of them has to get priority over the other. And there’s no doubt in everything Airbnb does. 

Pamala Parris Wideen, Host, Tavares, Florida, Since 2019 

I belonged to numerous groups on Facebook, and Airbnb is geared towards the guests. They’re geared towards making sure those guests are happy. I hear stories about hosts getting their listing de-listed and there’s no explanation. They say that the health and safety team will be with them. And these people, that’s their livelihood, and they’re getting de-listed with no recourse and no explanation. And that, I think, is very bad for Airbnb’s business model. Because it’s not all about the guests. Without the host, there are no guests.

Chip Conley: 

I haven’t mentioned at all, which is actually pretty fundamental and so different than Booking, is that we created something called the Airbnb Open. Now the Airbnb Open, it was in November 2014, November 2015, November 2016 in San Francisco, Paris, and Los Angeles. This was an enormous undertaking and was dedicated to the idea of bringing in our host community. Was it 20,000 people in LA? Hosts and then our most active guests. Our top maybe 1,000 guests in the world. But it was hosts and it was from 110 countries. It was a love-a-thon. The idea was to actually bring them together, help them share best practices, have them influence. Over half of our employees were there too. It was phenomenal.

The first Airbnb Open was in San Francisco and it opened Brian’s eyes like, “Geez. We need to do this every year.” And I was in charge of these things. And then, the second year it was in Paris. That was when we had the terrorist attacks. We were in the midst of it, 6,500 people in our group. On the second night, was when the major terrorist attacks happened in Paris. And so, that was hard. But then, we came back the third year and did it in LA and had 20,000 people.

I left the company in a full-time role two months later. Everybody already knew I was leaving. But quite frankly, the combination of me leaving and the fact that this Airbnb Open, which was dedicated to our host community, had grown so large and expensive to produce … Brian realized, “No. I don’t know how we can do this again.”

But I think Catherine Powell, who really runs the host program now, has done an amazing job. All the hosts. Both Experiences hosts as well as Home hosts. I think she gets it. She gets it. But I think there were people in between me and her that didn’t quite get it.

When I joined the company in 2013, there were 200 superhosts globally. And it was a program that was dormant. They had not added a superhost in over a year. The product team was recommending that they kill the superhost program. You don’t want in your ecosystem something that’s dying. Quite frankly, I have no idea how they set it up originally, but it was arbitrary who got to be a superhost. There were no standards for superhost. It was like, “We love you. You let one of the founders stay in your home. You’re a superhost now.” Before I joined, they said for the next year we are not adding any more superhosts. I joined and they’re ready to kill it.

I said, “No. This is exactly what we need to be able to create the carrot. Not just the stick.” If you just have the stick and you’re a company that’s all about the stick? The hosts won’t like you. Let’s create the carrot. Let’s actually, in the process of creating the carrot, help us have better metrics to understand who’s a great host and who’s not. And then, give our guests the ability to choose their listing based upon that. Totally owned it. Loved it. I probably made mistakes. But I got to say, the superhost program was probably the best ROI thing that we did at Airbnb. In the sense of how it built host pride. How it created some confidence in our guests. And frankly, how it helped us move toward quality.

Laurence Tosi: 

I was one of this senior partners at Blackstone (2008-2015). So I was on the management committee and I ran several parts of the business, including finance, business development, corporate strategy, stuff like that. And so, Blackstone at the time was private equity in real estate. I had started using Airbnb personally as far back as 2013. I traveled to see my parents in Florida. And so I knew about it, but we had an unusual meeting. Brian just reached out to me. Came to see me in New York and appeared in my office. That’s how we met. He just marched right into Blackstone and that’s how we met. Then we invested and then WestCap invested at that point. So we invested early with him. Started working with him on the future of the business.

At a board meeting at Airbnb in about 2015 or 2016, we started discussing the quality of the listings. And we were ramping up customer service and other areas of the company to give the best support we could to all our guests. So at this time I’m CFO. I was running both customer service and payments at the time, corporate development, vacation rentals and business travel are all reporting to me. So we started to see these professional listings — that’s what we called them — were beginning to take market share. They were doing very well with respect to ratings, and they filled the need for some travelers who wanted, if you will, more professional experience, a more professionally managed experience. And they were largely urban in what I would call gateway cities. And so that’s when we first spotted the trend. 

And Brian Chesky and I have spent a lot of time thinking strategically about how to position the company and how to think about it. And we made a presentation to the board of Airbnb saying, “The rise of professional listings is real.” And we’re trying to balance them in our ecosystem because the company’s origin, really its soul, was the individual homeowner, the individual host. That was really our soul. And we were seeing that other participants were starting to come into our ecosystem.

So we spent about a year going and meeting all the different players in the space, including by the way, meeting HomeAway, which at that point was owned by Expedia, just to gain knowledge of the dynamics of that space. So at the time, we came up with a paper and we broke up the listings into two things. At the time, we call it digital short-term rentals (DSTR), and then we had DLTR for digital long-term rentals.

So the long-term rentals space was Zeus, was Blueground, and then there were some other international players. And the short-term rental space at the time, it was Sonder and Stay Alfred, and they had a couple other competitors. And then there was the vacation rental space. And so, that’s how we broke it up. Ultimately, we bought Luxury Retreats to get into the higher end, luxury short-term rentals. And then we looked at, at one point, buying Sonder in the early days and ultimately decided that it was a different business model. And we didn’t want the conflict of our individual hosts seeing us buy a professional host because there’s a little bit of tension there, a little bit cultural tension to a certain extent. So we ended up not doing it.

So we invested in Sonder because I thought that Francis Davidson was an inspiring leader. He was well ahead of his competitors. And I thought he would win. I thought he was the strongest of them. And turns out all of his competitors had basically gone away. So away went Stay Alfred. And there were a bunch of other names in there that all disappeared and Sonder survived. 

There were also some asset-heavy businesses. Remember Nito down in Miami? They were buying buildings and they were converting them into short term rentals. They (Airbnb) invested in them after I left. And then they ended up in a lawsuit.

I think that the professionals complement Airbnb. And I don’t think Brian, Nate and Joe will ever let go of the individual host. They are in firm control of the culture and they are stewards of that culture. And they’re not going to bend to anybody. I just think it was a surprising option. We didn’t realize that it would get to the scale it did.

We had met with HotelTonight and frankly we recommended the deal before I left and then they got it done after I left. I always thought HotelTonight was a really unique product. And one of the tricky things about Airbnb is, sometimes people use it last minute when hotels are booked. So I always thought it was a great product. There was almost a 100 percent overlap between our users. And we thought it would be a really great fit. We had our eye on that for some time, for years.

(Why I left Airbnb in 2018) was another one of those urban legends. I just wanted to go run my own business. I made it clear that I wasn’t going to be at Airbnb for that long. And that if we were going to put off the IPO till later in — ultimately 2021 — the team was in place, ready to go. We just hired somebody (Greg Greeley, Airbnb’s president of Homes) from Amazon to come in and run the homes business in 2018. And I felt like it was a good time that I could go back to WestCap full-time. So, that was it.

The Information reported, and there were a variety of other accounts in 2018, that Tosi and Chesky clashed over the particulars of an IPO, and Chesky’s wish to broaden Airbnb’s services, including developing an airline product.

Laurence Tosi:

And one thing to dispute: I don’t know what we call it, travel industry lore, I was never aware of an airline. That one is one of those rumored things that’s taken on its own life. There was no point we were trying to start an airline or Brian never thought of starting an airline. Later they did. That was after I left. They had kind of a skunkworks in the company to create a flight OTA. I don’t know that to be true because I didn’t happen while I was there.

One article in one obscure journal speculated that those issues (timing of an IPO and evolving into a broader online travel agency) created friction between Brian and I. Brian and I both publicly have said that that is not true. And I’m very proud of the business they built. I think Brian has done an amazing job with that business, with its culture, with its brand. And I think the three founders have really stuck together and made really great decisions for them. I still in contact with them today and I think they’re great people. And I’m very fortunate to have built a world class, private equity firm over the last several years with over $10 billion in assets under management. One of the best returning growth equity firms out there. And I feel I’m working again with all my friends. A bunch is from Airbnb, a bunch is from Blackstone, a bunch from Ipreo. And it’s been a great place. I’m very happy about that.

Eric Breon: 

Wyndham Vacation Rentals (Vacasa acquired Wyndham Vacation Rentals in 2019) went through a sales process. Wyndham was a pretty sub-optimal business but with great inventory. They bought up a lot of great companies over the years, but they weren’t really adding any value. They were adding overhead, but a lot of the people that had made those companies great, a lot of the founders, had moved on. Performance was pretty middling. The asset wasn’t growing, they had a fair amount of attrition on a lot of their portfolios, but at the same time, tons of great homes, tons of great people. We really felt that that asset would be best served with us because we could add our own management and our own operational efficiencies across that portfolio, and really create a lot of upsides. That’s very much what we did on that one. 

On TurnKey (Vacasa acquired TurnKey in 2021), that’s a conversation we’d had for many, many years. I forget when the first time I talked to T.J. Clark. We’ve always been interested in the concept. We’ve always saw the synergies, but it was always really hard to figure out what was the right price for bringing the two companies together. It was some time before we came to an agreement on that. I think for a long time, we both agreed the combination made sense, but we were really waiting for a time where we both felt the match made sense at the same time. Took some time.


One difference between the two companies was TurnKey was historically better at managing contractors, whereas Vacasa’s historically more of an employee model. Vacasa is much better at employing housekeepers, instead of depending on the market. Is it predominantly an employee market, or a contractor market? TurnKey brings the advantage on one, Vacasa brings the advantage on the other. I think Vacasa is definitely better at driving revenue, IPO management, and marketing. I think TurnKey was better at their brand with regard to owners. If people looked at the TurnKey collateral versus Vacasa, they’d say this technology at TurnKey seems really advanced. Personally, my opinion differs, but I think that their marketing is a step above ours on all fronts. We were much better at targeting the right homeowners, they were better at the imagery and the pitch to those homeowners at times. There’s definitely a lot of merit to collaborating, and we were just chasing those same homeowners, so not having two reps chasing that same person, having just one salesperson obviously has some efficiencies there.

Vacasa was stronger in most markets. There were a few markets, like Austin, Texas, close to TurnKey’s roots where they’d been stronger, where TurnKey was more dominant. But in general, Vacasa had more scale across most markets.

T.J. Clark, co-founder Turnkey Vacation Rentals:

I think that Eric Breon (Vacasa founder) and John Banczak and I had pretty, had some real differences on how we thought about the space. Eric was a very, very aggressive entrepreneur. He really leaned into their initiatives and I think took more risks than we were willing to take. In the end, I really admire them for it. He made some very gutsy moves into real estate sales. His expansion was at a mind-blowing pace. Vacasa is in 400 U.S. markets, while TurnKey ended up in 85 U.S. markets. He did global expansion. I would say it’s a little more like a personal business style or business approach that was different. He was leaning into it so aggressively, which we admired. But in the end, when you sort of peel back the way we do business, there are just way more similarities in how we were doing things from our technology process. I think we’ve lent some technology ideas to them that they’re now rolling out more broadly but on a combined basis, there’s just no question, we were going to be better off together.Eric Breon: 

We’ve had a close relationship with Vrbo and HomeAway for some time. We gave them what they wanted, which was high quality, bookable inventory, and they gave us what we wanted, which was customers paying good prices. So, we had a very symbiotic relationship with HomeAway. On Airbnb, they were less sure of our space for a long time. They weren’t sure what they thought of the professional manager. Eventually they came around and realized, oh hey, maybe they like that six-bedroom oceanfront home, managed by a professional. Eventually they ended up welcoming our inventory, but for the bulk of our history, it was really that symbiotic relationship with HomeAway.


Booking.com’s relevance depends a lot on the type of inventory. Booking does an incredible job on the undifferentiated demand: people who don’t know if they want a hotel room or a vacation rental. If you type in, hey, there’s four of us and we’re going to Panama City Beach, they’re really good about presenting a vacation rental alongside hotel options. They’re far worse at presenting a luxury beachfront home. I own a home in central Oregon. I was mocking to someone at Booking about my listing on Booking.com, where it says something like, “This seven-bedroom home is 22 miles from Redmond International Airport and has a toaster and a balcony.” That is their automated description. On commodity inventory, that can work really well. A condo with a balcony just like every other two-bedroom condo with a balcony. But when it’s the more differentiated inventory — the large single-family homes — their system’s just not set up for that. Those customers are much better served by Airbnb or Vrbo.

Brian Sharples:

The first Super Bowl ad in 2010 was super fun. We hired Bev D’Angelo and Chevy Chase. And we did a redo of National Lampoon’s Vacation, filmed a whole movie about it. Our first entrance, it was USA Today top five in the Super Bowl. So that was a huge success. And the second year, 2011, we did the ad, which you’ve probably seen. Or if you haven’t, go back and see it. It’s funny. I was watching with my kids the other day. They couldn’t believe it.

Brian Sharples:

And our second Super Bowl commercial in 2011 was when we did this baby ad. We filmed it in Prague. It was this really expensive thing to shoot. It turned out to be quite controversial. I mean, we kind of knew it would be. But it’s one of the reasons that we used something that was obviously a doll, not a real child. And it’s one of the reasons we said, “Test baby,” on the screen to let people know, “Hey, this is totally fake. It’s not a real kid.”

But I was at that Super Bowl in Dallas. And there were so many people at the Super Bowl, I couldn’t get a phone call in and out. I couldn’t get internet. So there was this controversy going on. And it’s spinning around the company, and I knew nothing about it. I got home late that night, went to work early in the morning, and there’s literally a protest outside the office. There’s an RV, and a guy with a megaphone, and a bunch of people. And this guy is CEO of something called the Sarah Jane Baby Brain Foundation, which is an organization that tries to literally protect young children from getting thrown into walls. Because I guess it happens, from babysitters or things like that.

And so Carl comes into the office, and we’re looking down and seeing these people. And Carl says, “What do you want to do?” When you do a Super Bowl ad, and you spend all that money to shoot it. The entire campaign was maybe $15 to 20 million, where we spent $3 million to create it, the Super Bowl probably cost $5 million, and then there’s another 13 we’re about to run over a period of weeks. And so I said to Carl, “Well, let’s invite this guy up. Please, let’s go down, ask him if he wants to come up and talk. I would love to hear him out.” And he came in our office. It was me, Carl, and this guy. And I asked him who he was, and what was his organization, and how it got started. And he told me about the fact that his child got a brain injury from a nanny way back when, and that child had died. And then he had done a lot of research and found that little babies get abused all the time, and he had created this foundation to do it.

I looked at Carl. We had, again, something like $13 million committed to this thing in the next few weeks. I looked at this guy and I just said, “I’ll kill the ad. We’ll kill it. It’s the right thing to do. I appreciate you making us aware of this. I wasn’t aware of this.” And of course my board and everybody else was saying, “What?” But then, as it turned out, that same year, Groupon had run three Super Bowl ads. All three of which were offensive for a bunch of reasons. And it was a big deal. But when the press had called Groupon, all they did was defended their actions and said, “I can’t believe they think this is a big deal. This was all done in fun.” And when people called us, I said, “Yeah, well, we met with these folks. We understand that this is a sensitive issue. We didn’t quite understand it. We’re going to pull the ad. We’re creative people. We’ll come up with something else.”

For the next four weeks, we got more press for anything else we’ve ever done in our history, all positive saying, “This is an example. Here are two examples. Groupon is the wrong way to do it. HomeAway, the right.” And everybody wrote about it. Every major paper, and magazines, and all this kind of stuff. And I don’t remember the numbers in the end of impressions that that created, but it dwarfed the successful Super Bowl ad from the year before and ended up in the end really helping our business. So a lot of people hear that story about the baby and think it was just a really dark negative period for the company. It actually wasn’t. It was a dark negative period for about 24 hours. But then after that all our employees, I think, were very proud of what we did. It turned out to be one of those things if you do the right thing, you get rewarded for it.

One of the things I will say is that it was an amazing, and dare I say, magical period at least in my life. And I think Carl would say the same thing. There wasn’t a time in our history, we didn’t ever have a quarter, where we didn’t beat our numbers. We didn’t have a quarter where we weren’t having fun. And I like to say to people I miss it quite a bit because — and this is true of anything in the vacation space — I don’t know how I can ever replicate the fact that HomeAway, at its core, was in the happiness business. Our owners loved us. We were making so much money for them. We’d get letters every day about how they were able to send their kids to college, or they were able to pay off this debt, or whatever it might be. And for travelers, listen, some people had horrible experiences, but it’s such a small percentage of cases, and 99 percent of the people absolutely loved the fact that we could make this option available for them all over the world. So everything about the business always felt like, “We’re making all of our constituents happy. We’re making our shareholders happy.” And that aspect of it is something I really miss.

Glenn Fogel: 

If you recall, in the bible, Mary and Joseph, they’re like, “We’re in Jerusalem, it’s tax season, we got to have a place to stay.” It’s filled up. They end up staying in an alternative accommodation. It’s like somebody has turned their barn, basically, into an accommodation, if I recall. So this thing’s been forever. Even before there was an internet, people were renting out their homes and private residences all the time. I mean, my in-laws had a place, they bought a place in Long Island, in the Hamptons, a really tiny little nothing, which they couldn’t afford on their own, but they were renting it out to be able to have it. And that was in the early 1980s, and stuff. 

I remember my friends, a bunch of guys, we rented a place. It wasn’t the Hamptons, further to the west, and the way you did it then is, you had to go through a property manager.

And it was in the 70’s, I skied in Vail, and it was a condo, and that was the Vail Mountain Association that rented those out. This is not new. This is old. So when did Booking get into it? Long before I got interested in buying Booking, they had different things. They had what we call alternative accommodations. They were professionally managed. 

But the big thing that was really different, I think, really different was — I have to give them credit — I mean, there were other people doing it too, but Airbnb really having something that people really had not done before. Airbnb started out not renting out a full property, it was renting out a room, which also has been around for a long time too. Ma Barker Rents Rooms, or whatever. But this was different because online, it was a way for people to do that. And then they all started doing the full property thing, and it was getting rid of that middleman property manager-type thing that had been the normal way to do it in the past.

If you recall, we were 100 percent agency. We didn’t take the money. That’s really hard to do if you have a private property owner who’s renting out their vacation home. They’re not planning to be there to take a credit card, and what are they going to do with it at that point? Unlike the property that has a lobby with a person with a way to swipe the credit card, we saw that. So right away, that was a different way to do it. We could do it with professional manager but it was difficult with this.

Second big thing is — and this is definitely something we had think about (regarding Airbnb in 2009, 2010 and 2011) — it was illegal in a lot of places. Blatantly. I mean totally, absolutely, you were not allowed to do short-term rentals in New York City. Very, very illegal. Very illegal.

We started reading, OK. Let’s look at this. And there are other people doing that and starting, there were a lot of other competitors who were doing it. And by the way, we had talked with Brian Sharples quite a number of times. Actually, the first time we talked to them (HomeAway) was maybe, I don’t know, 2011 or 2012.

But again, the issue for us, was we were a public company so we’re concerned and making sure to do the business the right way and it’s legal. The second thing was, we are growing at a hundred million miles an hour and doing hotels only. You only have so many resources to spend so much time on so many things. So yes, if it fit the model the way you did with professional property manager, you could bring it in … The idea of coming up with a whole different way to do things, with all these other issues was like, well, you want to spend your time on what you do best, and while we’re still growing like this, not slow down or divert or fork the code. 


And the other thing which also was important was … you had a lot more partner contacts, too. So that’s going to make it less profitable. And another thing is it’s harder to scale. You get a hotel onto the site, it’s got 100 rooms. Great. You just increase availability to 100 rooms. You start going out, onesies, twosies, trying to scale private properties, that’s not as easy to scale. 

And on top of that, you had people losing a lot of money doing it, not just Airbnb, a lot of people were losing a lot of money. And the question was, well, do you want to go into a business that is so hyper-competitive … to lose lots and lots of money. If you’re private and you’ve got VC (venture capital) people who really believe in the long-term future of the thing, and are willing to suffer huge losses, that’s one thing. But when you’re a public company with public shareholders who expect you have a certain amount of a return, and are you willing to go into another thing? 

Futurestay CEO Philip Kennard and Evolve CEO Brian Egan with Skift Senior Research Analyst Wouter Geerts

(L-R) S. Philip Kennard of Futurestay, Evolve co-founder and CEO Brian Egan, and Wouter Geerts, Skift Director of Research, Data Product at the Skift Future of Lodging forum in 2022. 

Brian Egan co-founded property manager Evolve in 2010 and has served as CEO from then to the present:

We are a very different model than Vacasa, but ultimately we are competitive. Most owners make an easy choice between whether their value proposition or our value proposition makes more sense for them. But at the end of the day, we’re a vacation rental management platform. And one of the ways to think about the difference between the two companies is simply that we have 20,000 properties, exclusive properties active on the platform, and they have about 35,000. We have 900 employees, something like 10 percent of Vacasa’s headcount.


In 2010, my co-founder Adam Sherry and I are both at Exclusive Resorts. We’re looking at the vacation rental market and we’re coming to a few conclusions. The first is that the market’s going to mainstream, and we believed it has only just begun that process, becoming a mainstream travel category, along with air hotels and car. The second thing was that with that mainstreaming, the consumers expectation of the category would rise. Our third conclusion was that professionalization would matter more, not less. And that got us to the place of saying, “Lett’s go build a scalable tech-enabled format for professionalization in the category and that’s what we’ve done.


This is fall of 2010, it fit in his basement. We unpacked the whole industry, put it on whiteboards, put it in docs, built the basic plan for the company, raised funds in spring of 2011. We raised some seed capital. I think our first seed round was a little less than $500,000, $400,000 or so. This was not a business that was shot out of a cannon. And the first thing that we did was basically cobble together a way to run the business. And we actually did it on a third-party property management software platform. We put the value proposition together and were going to charge a 10 percent management fee at that time.


Owners were going to handle their own onsite servicing, housekeeping and maintenance and we’re going to get distribution set up through, at the time, mostly HomeAway/Vrbo and Tripadvisor/FlipKey. I think we got 25 owners to say yes and we started. We launched the site on August 25th of 2011 and got our first booking. 


We knew that we wanted to be on the supply side of the equation. And part of our hypothesis was that the OTAs were going to come into the space. At that time Booking wasn’t in the category. Booking’s was a Phocuswright saying we don’t want anything to do with that. We’ve got this pristine booking funnel. Don’t bring that noisy mess near it. And Expedia wasn’t in the space yet. But our belief was that HomeAway would continue to develop, that the bigger OTAs would come in, and Airbnb at that time was, I think, a Series A company. They were still mostly focused on apartment sharing, metro areas etc. but we could see that they were going to expand their scope and become a major player.


Therefore, we concluded that rather than trying to compete with all of those companies, the better move was to focus on refining the supply and professionalizing the supply of the industry and partnering with those companies, which is what we did. 


We figured, I think correctly, that we could leverage distribution to drive quite a bit of performance. And then ultimately we had to get to more scale in order to matter enough to drive a meaningful amount of our business direct, as we do today. On the housekeeping and onsite services side, we’ve viewed those services as local services that are best performed locally. And from our perspective, half the market at this time had gone the route of being for rent by owner. And they were all coordinating these services for themselves anyway. And we figured that this allowed us to create a really interesting value proposition in which we would charge a much lower management fee. We would drive essentially the value proposition of higher performing and lower cost, more flexibility and control for that owner. Since then, what we’ve done is built out a partner network. 

This was in 2013, we started that. And by the way, it’s a key part of the value proposition in the sense that for a lot of owners, one of the reasons they didn’t want to go with the traditional legacy property management model was they didn’t want to turn the care of their home over to that company in full, they wanted to select their own vendors. They knew the people that they trusted and were already happy with. But for other owners, they didn’t have those services set up. And so we went out and built a partner network of thousands of these (vendors). And I think this is a key part of our story is that we’re the largest property management or vacation rental management platform that’s been built organically. 


If you fast forward now to today what’s really interesting about that is that over 70 percent of new properties being activated on our platform every month are actually new to the market. These are not people who have ever rented this property before. We’re not just borrowing from rent by owners, we’re not just borrowing share from property managers, we’re actually helping to make the market bigger.


Back to the very beginning around August 2011 when we launched the company, we had this homepage set up and there was maybe an explainer video and some content. And then below that, it said proud partners with — and it had logos from HomeAway, Vrbo, FlipKey and Tripadvisor indicating that those were our distribution partners. And we ran some PR, we were in TechCrunch. And we turned the site on the next day, we get a cease desist order from HomeAway saying they’re not aware of any partnership between our companies. You do not have permission to use our logo. And I chuckled because of course at the moment we had worked hard to even get them to do a commercial deal with us and allow us to distribute on the platform. That was suddenly threatened. And it was a scary moment. We worked through with them. And it’s funny now because they became a really important partner to us.

Jeff Hurst, former HomeAway chief strategy officer and chief operating officer Expedia Group brands:

I tell the history as there’s pre-IPO HomeAway, there’s public HomeAway, and then there’s the transition from subscription HomeAway to an e-commerce, commission-based HomeAway. And that coincides with the Expedia acquisition. They’re a little linked, but we were going to do that regardless of ownership structure. I think it made it easier, but we were going to do that either way.


I think Airbnb raised their first real round in ’11. And as they were building their business, Carl was relatively close with Brian Chesky. I think they still have a decent relationship. And I remember a conversation where they were asking Jeff,the new strategy guy — I’d probably been there right around a year — how do we think about this? So I did the McKinsey style, and I said we’ve got a superior economics because they’re only in shared spaces. It’s going to be really low ADRs (average daily rates) and really short lengths of stay.. And they’re going to have all these regulatory challenges. This was not something we needed to pay attention to. And eventually, being the chief strategy officer, I’ve laughed at myself plenty of times over what was clearly an adjacency threat and great way to build a business, and I was saying that’s not who we are. We spent several years, I think, stuck in a trap of are we going to try and out-Airbnb Airbnb or are we going to be something unique? And I think really in the last, maybe three or four years, we re-found that unique thing we are in a way that’s given us a lot of momentum.


I got the chief strategy officer job in March of 2015 and I remember Brian had done a pretty big management shakeup. I got this new role and half an hour after I got the job, Brian said here’s why you have the job. We’re going to run a strategic process and work to understand are we going to stay public, go private or be acquired. You’re going to run this with our CFO. And what I need you to focus on is what is the business plan for us getting out of subscriptions and into a commission model. And so we just sprinted at that for a very long time.


And it was interesting while we were in the process. So we’re talking to everyone you would expect to be involved in that process. My dad actually passed away. And I was running the process and I’ll never forget that it became a good reminder of travel in general of what I had experienced at Rezfest. People stayed close and knew each other. Real competitors of ours, two of the CEOs who were in the process, found my mobile number, reached out, and expressed condolences. I was not their peer at the time. And I remember thinking that was particularly cool that they were taking time out for someone they only met in a pitch show. And it was like a reinforcing the dynamic, you pick up at a Phocuswright to this day, or a Skift conference. People enjoy the category and want to be with each other. And see the category succeed as much, sometimes, slightly less than market share.


I gave an all-hands speech in December of 2019 rallying the Vrbo team. I had just become president and saying congratulations, everyone, the worst year we’ll ever have is behind us.

We had just kind of gotten invigorated around this smaller target. We were going to go after complex family travel, really nailing our large-format premium houses, taking a very, a different tac. And we were so fired up. And then the pandemic hits, was just breaks, full stop. The first thing I did, I called the head of VRMA and I called each of our top customers property managers, and a handful of Vrbos. I remember walking around my backyard, on the phone asking everybody what do you need help with? What are you going to do? What happens next? And it was pretty fast that Airbnb announced their policy of basically discretion-less refunds.


It was equally pretty fast that I came out on the opposite side of this. The industry’s going to do the right thing. If we let them work it out, the managers and the individual homeowners, it’ll be better for the system than if we draw a hard line in the sand and go that route. And I think it scared the hell out of Peter (Kern, the Expedia Group CEO) at the time in terms of we were going to swim in the opposite direction. But it was immediately just met with an incredible amount of enthusiasm from owners and managers, to let them do their thing and skepticism from travelers. But overwhelmingly, I think the travelers ended up in a similar spot.


But that was a really dark month. My wife and I in the third or fourth week of March, I remember we both get text messages in the middle of the night, death threats, about somebody who was a traveler in Florida and this ruined their life. And they were going to come attack our family. And I called Peter and said, “This job is … I’m not sure this is worth it.” And it was very jarring. And at the same time, such a litmus test for the state of society. Everybody was so on edge and so terrified of what was around the corner. People going crazy, in that case over $700. And I remember thinking now I’ve got this death threat email, and you didn’t even leave me your account number. I can’t even fix it.


When I describe the category now, I think we do the most artful job at being good for individuals and managers. We’re more balanced, and I’d say the tie goes to the guests, but it’s not everything. I think one of our competitors is super individual-centric (Airbnb) and one super manager-centric (Booking.com). And then we do the most artful job of balancing what our partners need and what travelers need.


The Vrbo Fast Start program starting in 2021 was born out of us starting to get the same email, almost like a form email. I think it was from the northeast. Imagine getting a chain letter, but it’s coming from a bunch of different email addresses and it is always going to me, Peter and Barry (Diller, Expedia Group chairman). And it was interesting in that the chain email basically said, if you can help me get off of Airbnb, how do we figure this out? And it was about what they had done with cancellations and how it had basically, in a lot of cases, almost bankrupted people. People had to take out home equity lines and people had to borrow money in order to get through it. And we figured there was enough smoke that there was something worth going into, which was basically we can help partners diversify. It’s hard to give up the other thing without having something new, especially the way ranking works, building reviews, and building tenure. So we tried to find a way to where we could give people credit for their business they run, on our site without us having observed it with firsthand data yet. And it’s been a big hit. We’ve really found a lot of people with it. It still has some of the same challenges of yesteryear: The people are still hard to find. And so you count on word of mouth, and that’s why we started running some of the above- -the-line campaigns last year, too. We are much more aggressive on marketing the partner side of our marketplace than we were three years ago or 10 years ago.

Ivan Marenco, Despegar, starting in 2017 and is currently vacation rentals vice president

In 2013, we did the first, let’s say, commercial approach to start selling vacation rentals in our platform. What we did back then is we made a first partnership with another OTA, Zukbox, that was specific for vacation rentals. It was a local startup from Argentina — the footprint was also Latin America. Despegar in those days had a complete footprint in Latin America, from Mexico to Argentina, as we do today. I was not personally involved. I was not at Despegar those days. I entered the company in the beginning of 2017.

In 2013, what we did was we integrated in a basic way, both platforms. And when the Despegar client entered our site, he was able to go to the sector on the site where you can find the vacation rentals and complete the purchase of a vacation rental there as clean and safely as possible. After that in 2014, we acquired Zukbox. So 2014 Zukbox platform was merged with Despegar platform.


Despegar always, even now, looked forward to completing the portfolio of travel products that we can find in the market. In those days, Airbnb was already there on the market. They already were a known company. They were making big noise. So Despegar, as a leading company in Latin America, we were not willing to lose this train that Airbnb was creating or pushing in this new category. And we tried to put all the efforts there also to improve our portfolio of products in the region.


What we understood about this segment, at least in Latin America, and from our experience, and what we figured out in those days, was that the vacation rental business was already happening, but most of it was offline. Now, like the typical family that will go on vacation and will search for a house on the beach, in the mountains, on the lakes to find out where to stay with the whole family. They are probably not too focused on urban apartments, but most on vacation houses. 

In those days, when your family was going to the beach to find an apartment or a house, probably someone from the family would travel a couple of months earlier. For example, here the peak season is January. I remember when I was young, my father traveling in October, or September to the beach to find a house and coming back to say, “OK, I got one.” Probably my mother would have some complaints because I think my father would try to balance more the economics than the comfort.


In Brazil, there are lots of smaller cities where you can go and stay. You know in Brazil you have this mix. It’s called a pousada that is something between a hotel and a house where you don’t have all the amenities of a hotel. And that was the kind of product that you usually go to similar to a vacation rental. Many times the owner of the pousada was the same guy who is attending you there or receiving you. In Argentina, where Despegar was born, for example, in Mar del Plata, a very big city beside the beach, or in Uruguay, Punta del Este, they are not beach cities as in the Caribbean. The motive to go there is not to go to an all-inclusive, but just to go with your family and stay in a house. It’s like also a beach vacation, but very different to the one you can find in the Caribbean or in Mexico. It’s between a hotel and house. That’s more in Brazil, but in the rest, I would say they are more like a house.

We have a big footprint in Latin America and in each country we may have a different name for vacation rentals. In Mexico it’s alquileres vacacionales, it looks like very similar to the English. But for example, in Argentina, we call them alquileres temporales which means temporary rentals.


We had two or three businesses together doing vacation rentals. One was the complete booking, but the advertising business was also there. Then they could do the booking offline or do it outside our platform.

After a couple of years doing that, trying to develop the products in parallel, you find that they compete a lot, that there is some kind of cannibalization in the business. But we never said let’s unplug the vacation rental business. It was like the youngest brother of the lodging family, the small player that was growing. But we always were trying to balance this business with selling hotels, figuring out how to make the pie grow and not to cannibalize. That was our main issue to solve every day.

We have two different teams (for hotels and vacation rentals), and they were some days fighting, some days working together. It was probably when we talked with companies in the sector, like Expedia, that we know that they suffer similar things. And it’s interesting how the company, when we start growing and maturing and when Despegar made the IPO, the company was growing a lot. So both businesses were booming.

In the final and third installment of The Definitive Oral History of Short-Term Rentals, you’ll learn that:

“Another data point that was brought to us, was 27 percent of our guests in 2017 had stayed in a home, and that meant they were leaving our portfolio. And that data point for Arne (Sorenson) and for Stephanie (Linnartz) was an aha moment. Why would we want 27 percent of our guests to leave our portfolio versus staying within Marriott, Bonvoy?”

Jennifer Hsieh, Homes & Villas by Marriott International

“I had a gentleman seated to my left and I asked him ‘Who are you? What do you do for a living?’ And he says, ‘Oh, my name is Jeff Boyd, I’m the CEO of Priceline.’ I said, ‘I’m Simon, I’m running a property management company in Europe. We have 24,000 units of vacation rentals. I have bookable inventory, 24/7, all exclusive.’   He said, ‘Really? Let me make a quick phone call.'”

Simon Lehmann, Interhome

“Brian (Chesky) and I talk. Sometimes we’re at conferences and we’ll say hello and stuff. We’ve spoken. Yeah. Give this man credit. He created a giant business. If I had a time machine, there’d be a whole bunch of things I’d do differently. I’d be willing to tell our investors, and tell everybody, that we believe the future requires us to sacrifice some of our near-term profitability to more fully invest in the future in this area.”

Glenn Fogel, Booking Holdings CEO

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