Skift Take

Here's our deep dive into all the opportunities and challenges that lie ahead as Airbnb transforms itself into a super brand of travel.

We already know why Airbnb is doing what it’s doing with its newest product, Trips, and more — at least from Airbnb’s point of view.

But the bigger question is: Can Airbnb ultimately succeed in doing all of this, or does it risk a devaluation, a massive distraction, or something greater?

That’s exactly what we set to find out by speaking to a number of industry veterans to gather their thoughts on whether or not they think Airbnb can maintain its current $30 billion valuation and, perhaps, even grow beyond it to become that “super-brand” of travel that it aspires to be.

Can Airbnb continue to grow? If yes, into what? Or has it already reached the peak of its success as a company? Will it disrupt the online travel business in the same way as it disrupted the traditional hotel industry? What challenges lie ahead? Can it overcome them?

Here’s what those industry experts had to say on the matter.

Does This Make Sense in the First Place?

“To start with, it makes complete sense for them to branch out into related areas of travel,” said Rod Cuthbert, CEO of Rome2rio and founder and former CEO of Viator. “For their customers to get to the property they’ve rented, they need to travel. And Airbnb has all their details and knows where they are going. It makes complete sense they’d offer some of those services to them, and offer services in destination, like the Trips. I don’t think there’s any question they ought to be doing it.”

But does it make sense for Airbnb to start offering flights, car rentals, and other services? The jury’s still out on that, more so because it’s hard to make money by selling flights and other forms of transportation.

“In transportation,” Cuthbert noted, “they’re entering a mature marketplace with many savvy, experienced competitors. Building something new and innovative enough to lure their customers away from established players will not be easy, but they are starting with a vast and loyal customer base, and that will count for a lot.”

“What I think they are doing is experimenting with new revenue streams and figuring out other ways to capitalize on this great business that they have built and to capture a larger share of wallet from the traveler when they are traveling,” said Travis Katz, co-founder and CEO of (formerly Gogobot).

He added, “Is this as big as what they are doing in houses? It’s hard to say; I think there are reasons to be skeptical. It’s an obvious extension from what they are doing, and I think it makes sense to leverage their platform that way.”

T.J. Clark, CEO and co-founder of Turnkey Vacation Rentals, sees Airbnb’s venture into tours, activities, and more as simply “adding more traditional travel around that unique offering” they’ve created with home sharing. “It’ll be hard to be new, these days, in selling an airline ticket though,” he added. “It’s a logical add-on, if you will, to their core hospitality offering, for the same reasons why Expedia sells air, for example. It helps the hotel product.”

According to Chip Conley, Airbnb’s global head of hospitality and strategy, Airbnb wants to be a travel company first and foremost. He told Skift, when he first joined the company three years ago, “… there were people who were saying, ‘Well, why don’t you get into the conference space business? Or the office space business? You’re in the space business. You just, through technology, help marry demand and supply.’ From an objective, almost technician way, you could have said, ‘Okay, yes, we should be in the space business.’ I said, ‘Oh no, we’re in the travel business.’ Ultimately, internally, there’s this internal mantra [where we ask ourselves], Do we want to be the most loved brand in travel, or the super brand of travel?”

In addition to aspiring to become a super brand of travel, many suspect Airbnb’s decision to add Trips and more was also motivated by pressure from its investors, no doubt influenced by its latest funding round, which valued the eight-year-old company at $30 billion.

“When you raise as much money as they do,” said Andrew McConnell, CEO of, “their investors have some expectations.”

As are the expectations that some in the industry have for Airbnb, too, McConnell included. “Look, I’m not sure it’s a bad thing to do something a lot of people have already done,” he said. “Look at smartphones, like Blackberry. Apple comes along with superior design and takes over. If you want to look at travel, it’s been staid, corporate, and doesn’t have beautiful design. [Airbnb Trips] might not be a terribly different product, but I think Airbnb is saying, ‘We’re just going to deliver it so much better and the user experience will be so good.'”

Is This as Far as Airbnb Can Grow?

The answer from industry vets here is a resounding no. This is probably just the beginning for Airbnb, and it still has plenty of room to grow, even with its core business alone.

“I’m not sure if any limits have been reached,” Cuthbert said. “I very much doubt that. But it does make complete sense for them to branch out into other sectors within the travel space. Their customers are loyal, their core product is differentiated, and they have the capital required to grow their business into these related sectors. The potential is enormous.”

“I don’t think they’ve even come close to reaching the limits of alternative accommodations,” said Robert Birge, chief marketing officer of Lola Travel.

So, What Exactly Is Airbnb Becoming?

Is Airbnb transforming itself into an online travel agency (OTA) like Expedia or Or is it becoming something more, perhaps a new breed of OTA?

The truth is, it’s hard to say. Yes, in some ways, Airbnb might resemble some of the other OTAs in their newest endeavors but, it’s important to remember that it’s not exactly like them. Just as Airbnb disrupted the traditional hotel industry, we can expect it to do the same in online travel.

“Airbnb has taken a different product and very successfully built a brand that sells a different form of travel,” said Birge. “The rest of the [OTA] category can sell offers, prices, and features, and specials. But Airbnb can offer all of the wonderful emotion that comes in the world of travel. It’s a different kind of travel, where you can ‘belong anywhere’ and ‘live like a local.’ That, in and of itself is a huge threat to the incumbent industry.”

But can Airbnb stand apart from their new competitive set? Should they?

Clark does see Airbnb becoming more like an OTA and, in doing so, he thinks it will have to become a bit more “traditional” in some ways.

“I think Airbnb is moving to a more traditional OTA model, especially with the way they will likely add air product and car product,” Clark said. “To me, they are getting more traditional and more mainstream. Everything they are doing is coming from the OTA playbook that’s been baked in for 20 years. Private home accommodations are also becoming more mainstream. The exposure of private accommodations to the mainstream just makes it more of a transitional OTA product. That’s where they are headed and they are going to be a big player.”

Airbnb’s Chip Conley, however, has said, that unlike traditional OTAs, Airbnb doesn’t “want to be a transactional business. Most OTAs are transactional businesses. We want to be a transformational business because margins are better, but not just because margins are better. Because we want to actually transform people’s lives.”

If Airbnb isn’t necessarily traditional or transactional, however, then what kind of a business is it becoming? Travis Katz thinks that the holistic direction Airbnb is headed in is similar to the one he too is pursuing with, and for good reason.

“Our focus has always been on thinking holistically about the traveler,” he said. “All of those travel companies, because they were so focused on harvesting people from Google searches, they were just transactional sites. They didn’t think about the experience side. We saw that big opportunity of connecting with travelers, as has Airbnb. We’re going after that same opportunity, albeit in a different way. The world is changing. If all you’re focusing on is transactions, it’s going to be a lot harder to build loyalty among your users and how they are thinking about having great experiences.”

When Airbnb first announced the debut of Trips and Places, immediate comparisons between TripAdvisor and Airbnb also followed. Those comparisons, however, seem to be misplaced, said Cuthbert.

“TripAdvisor’s business is all about people coming on their site and finding information about hotels and making accommodations decisions based on other people’s reviews,” Cuthbert said. “What Airbnb has done is create this unique global marketplace for booking. TripAdvisor is trying, with some difficulty, to transition into being a place of bookings, but it’s not yet certain customers will follow them on their journey. Even if they don’t, TripAdvisor still has an amazing business as an information portal.”

“TripAdvisor started off as a discovery tool, and it’s not built as a booking engine,” McConnell said.

Cuthbert, for one, thinks that because the lines are becoming so blurred these days, between what’s a metasearch and what’s an OTA, it’s really hard to put a single label on a company like TripAdvisor or Airbnb. “Given all that, however,” he said, “becoming an OTA is where Airbnb is heading but, no doubt, they will look very different from Expedia or the other OTAs and other players in that space.”

If there is a business-type that Airbnb seems to be modeling itself after, Katz suggested, it would be those “super apps of travel where you have a single app that you can use for your entire experience as a traveler, from researching and booking to navigating tips and finding things to do.”

He added, “In the travel space, companies that are thinking holistically about the travelers are going to have an advantage over time, just because people don’t want to have to bounce from app to app to app. It’s really fragmented now, but look at what’s happening in Asia, in places like China, Korea, and Japan where see the rise of these super apps.”

McConnell thinks that, if Airbnb is “successful in displacing OTAs or redefining what an OTA is,” it “would change how we think about travel and if we can own the end-to-end experience.” A fitting comparison here, he said, would be Amazon, for example.

“I don’t even comparative shop anymore,” he said. “I go to Amazon and buy whatever I want to get. When I travel, I have my city guide in the [Airbnb] app. I have my way to contact the host, book my flights, etc. If they just own travel, it’s not just an OTA anymore. It changes how we travel and what we do when we travel. Accommodations, for Airbnb, could be what books were for Amazon; it could just be the start.”

Amazon-like ambitions aside, Airbnb does face a number of challenges in growing itself into a super brand of travel. Here are just a few:

Trips: Not Mainstream Enough to Scale?

As Skift has noted before, getting into the tours and activities space is not always an easy feat. And once you’re in, the prize isn’t so huge.

“I’ve always heard that, trying to solve in-destination experiences and tours and activities is where startups go to die,” said David Jacoby, a San Francisco-based Airbnb host and CEO and co-founder of Hostfully, a startup that helps hosts create personalized guidebooks for their guests. “It’s tough. It’s really tough.”

And while most industry watchers think Airbnb has incredible brand recognition and a loyal user base — two things most tours and activities startups often lack — there are still challenges Airbnb will have to overcome to make Trips a successful part of its business.

“The path they have taken is terrific, but it will be a challenge to scale it, as the experience providers are inherently small and hard to find,” Cuthbert said. “Here’s an example: ‘Sophie’ hosts the ‘Drawing dumplings and drinks’ experience in London. She offers it only two days each week, with 10 spots, at $62 per person, on each day. Assuming she fills every slot on every day, and assuming Airbnb gets a 20 percent commission, that’s a total of $12,000 they can make from this tour over a full year, and that’s if they fill every slot, which won’t happen. They need to find lots and lots of Sophies for Experiences to make a meaningful contribution to the bottom line.”

Cuthbert noted that one company whom Airbnb may look to for inspiration as they look to scale Trips would be Urban Adventures, who “have already built this exact model out on a bigger scale, and with the same goal of an offering that is easily differentiated from the ‘mainstream’ offerings of Viator et al.”

He also believes Airbnb may eventually have to “backfill” their Trips with “more mainstream tours” to “get volume and turn this into a business that’s financially meaningful.” While dumplings with Sophie are nice, more people want to see the London Eye, Louvre, or Empire State Building.

Cuthbert recalled that, while at Viator, “for every one of those cool, not mainstream tours we sold, we sold 20 or more mainstream tours. Those tours outsold all of the other tours by 20 to 30 even more to one.” He added, “You cannot build a big business, a business the size of Viator, just on the type of product they’ve launched so far. People, of course, are ‘cool,’ but they are mainstream as well.”

The tricky part here, however, is whether or not Airbnb risks losing its cool factor by becoming more mainstream in terms of its Trips offerings. Similarly, if Airbnb does eventually decide to work with more established tour partners, will that detract from its peer-led twist on tours?

Quality will also be something Airbnb will have to pay close attention to, especially with Trips. “If I’m on vacation and I’m going to give one of my days over to a complete stranger to guide me, I really want to know that it’s going to be good,” Katz said.

Places: Too Editorial and Not Functional Enough?’s Katz wondered whether Airbnb’s “visually beautiful, highly curated, and editorialized” approach to both its Trips and Places functions, while eye-catching, may not be viable for scaling up or very user-friendly.

“It’s really hard to scale stuff that curated and editorial,” he said. “I’m sure they are working on this, but they have to ask themselves: how do you move from this hand-curated content and having staff members going out to contact influencers and shooting videos, but having it all scale as a marketplace would? The scalable business model around this is not there yet.”

Katz also said that, the way in which Trips and Places are both organized right now is very “magazine-like” but not necessarily the most user-friendly. “It requires a lot of effort from the user to browse through each one of these activities and figure out if this is something I’m interested in,” Katz said. “It’s very niche, and figuring out the right Trip or Place that’s right for me is not super simple.”

Transportation: Not the Most Lucrative, or Easiest Business to Sell

If Airbnb does decide to eventually add flights and other transportation services to its repertoire, they’ll do so with the knowledge that it’s a part of the travel business that is both difficult to get into and to differentiate.

“The key challenge they face is that because they were first in peer to peer accommodation, their offering was inherently differentiated, and everyone who came after them was somehow derivative,” Cuthbert noted. “In transportation, they’re entering a mature marketplace with many savvy, experienced competitors. Building something new and innovative enough to lure their customers away from established players will not be easy, but they are starting with a vast and loyal customer base, and that will count for a lot.”

He added that ground transportation, in particular, can be challenging: “To sell a train from Tokyo Narita airport to Kyoto you need a set of partnerships and technology that’s different to what’s required for a train from Rome to Naples, or a coach from Heathrow to Cambridge, or a ferry from Athens to Mykonos. Ground transportation offers Airbnb enormous opportunities, but it’s certainly not going to be easy.”

Cuthbert also noted that there’s not much money in selling flights, as most OTAs have also realized over time. “The OTAs started with flights and then switched to hotels where the money is, because the airlines figured out how to build direct distribution channels and they don’t offer much in the form of commission,” he said.

Cuthbert thinks Airbnb can work with a global distribution system or other partners like Google and its subsidiaries to build up its airline business. “But,” he said, “It will be a service to customers, rather than a key revenue driver for their business. There just isn’t enough money in commissions on flights.”

Airbnb’s Resources and Talent Challenge

Having the right partnerships and expertise will also be crucial for Airbnb to succeed in Trips, Places, and more.

Airbnb, historically, hasn’t been very acquisitive. Its last purchase was made in September for Spanish tour startup Trip4Real, and some suspect that acquisition was driven by a desire to add more European inventory to Airbnb’s Trips product.

But a few of the sources we spoke to for this story wondered if the company had the right talent — or technology — to power its broader goals. And if not, will the company try to build that technology on its own? Or will it buy other companies and/or talent to do so?

“Do I think Airbnb should try to build all of this themselves, in house?,” Katz wondered. “I think that’s a tougher question to answer. They have built a really good confidence in building a marketplace around places to stay. But that is a very different business. They need to figure out where they have more competence to use: where their core competencies are and where they need to invest. Something like flights, for example, I think it would make more sense to partner with someone else than try to build that in house.”

Cuthbert added, “The mountain that the Airbnb team has scaled to get to their current position is very different to what’s ahead of them. Moving into these mature sectors of the travel market is less about peer to peer and more about dealing with a vast network of operators, often state-run, usually slow moving, and sometimes reluctant to change their ways. The people who have built Airbnb’s business to date may be surprised and frustrated by some of the industry practices they encounter, and wanting to change things may not easily translate into being able to change things.”

McConnell suspects that Airbnb’s history may suggest the company will continue building product on its own, however. “They do have experience in building something, and their culture means a lot to them. They really want it to be Airbnb owned, operated, and branded. I think they’ll do acquihires to get the right talent they need.”

The Regulatory Landscape

Airbnb is not immune to regulatory battles near and far, and Skift’s coverage of its particular challenges in New York City, the company’s biggest market in the U.S. second only to Paris, is proof of that.

“I think that the regulatory issues are a surmountable challenge, but not a nontrivial one,” said Katz. “They are spending a lot of money and effort with regulators to find ways to work with those cities. Having Airbnb in those cities under the right structure can be good for the cities and for Airbnb’s business. Something that will be ongoing for them for a number of years is to try to figure out the right regulatory approach that’s going to work.”

Others, like Bradley Tusk, founder and CEO of Tusk Ventures and Tusk Strategies, think that tighter regulations in a market like New York could, potentially, downgrade Airbnb’s overall valuation. Tusk is the ex-aide to New York City Mayor Michael Bloomberg who helped Uber navigate New York City’s regulatory hurdles and the Taxi and Limousine Commission. “It may just mean that instead of being a $30 billion company, they’re a $20 billion company,” he said. “It’s just a question of pricing.”

Airbnb, for one, seems to be making this a serious part of its agenda, pledging to work with cities to craft better, common sense regulations on short-term rentals. Just last week, it debuted a comprehensive report, a framework, for how it wants to approach working with cities, called The Airbnb Policy Tool Chest.

While the report was a clear signal that Airbnb is more willing than ever to work with lawmakers, the report also showed, however, that the company would prefer to craft new short-term rental legislation than accept existing laws that could compromise its business.

Is the Airbnb Community Ready for This?

To say that Airbnb has a passionate global community is not an overstatement, and it was on full display at the most recent Airbnb Open conference, which welcomed more than 7,000 attendees from around the world, and sold more than 14,000 tickets.

Clark, who attended the Airbnb Open in Los Angeles where Chesky announced the debut of Trips, said, “It feels like there’s a real movement happening around the users—they are really fanatical. Airbnb, in some ways, has become a way of life, a new way of life for people who are owners or renters of these places. What really hit home for me, is that this genie is not going to get put in the bottle by places like New York City.”

Yet as passionate as the Airbnb community is, will they get onboard with all these new businesses that the company is adding?

“While many of their users may restrict their accommodation search to just the Airbnb site, they’re unlikely to be quite so loyal when it comes to flights, because they know that shopping around a number of sites and apps can be a valuable exercise when booking flights,” explained Cuthbert. “Doing something with flights that convinces users to abandon Kayak, Expedia, Skyscanner, et al, is a technology and brand extension challenge of considerable size.”

Whether or not Airbnb succeeds in convincing its already loyal base of users to use the company to book tours and activities will largely depend on the strength of its brand and marketing.

“I think their brand has captured this sort of cultural ethos that is looking for authenticity and looking for experiences over consuming goods and they have really captured that,” said Birge. “That’s where a lot of the brand magic comes in. The Trips product seems to be a huge reinforcement of this and will push for growth their way. I would argue that they are the brand leader in travel right now. They are not the market leader, but they are leading the market in terms of how people are using brands to perceive the market.”

Final Thoughts

As Airbnb embarks on this growth phase, perhaps the biggest challenge for the eight-year-old company will hinge on how much they’re able to stay true to their origins, to what makes Airbnb, well, Airbnb. If they can manage to be different enough, can Airbnb ultimately become that super brand of travel?

“It’s the innovator’s dilemma,” said Clark. “They say breakthrough challenges come out seeming really weird or challenging at first, and this one has all that stuff. Although I do think it has a chance. I went to Phocuswright before going to the Airbnb Open, and I didn’t hear or see anything as innovative as this at Phocuswright. No traditional OTA is taking such bold chances. I really like that. This idea is just crazy enough it might work.”

Likewise, Birge said he thinks Airbnb gamble will ultimately pay off. When asked if he thinks Airbnb will succeed with Trips and more, he said, “They’ve been able to do so across millions of non-standard, unregulated accommodations managed by people who likely didn’t go school for hospitality services. No one thought they could do that, and I still recall people calling it a niche. I’m going to bet with the table on this one.”

Katz was a bit more reserved in his assessment. “I think that the underlying concept they have is the right one, but the jury is still out on the execution. It’s still early and we just have to see how they evolve it.”

As a true disruptor, Airbnb’s foray into tours and activities isn’t just good for Airbnb, Cuthbert said.

“I think this is just terrific for the rest of the travel industry and the established players,” he said. “It puts pressure on them to up their game, just from a user experience perspective. What they’ve done with the Trips product is so beautiful. All boats will rise on the same tide here. New ideas and new approaches will cause others to reexamine their own offerings and do better themselves. It’s good for everyone.”

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Tags: airbnb

Photo credit: A promotional image of one of Airbnb's new Trip experiences. This social impact experience lets travelers give back to the local community in San Francisco. Airbnb

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