Airbnb’s Trips Platform: Turning Trips Into Journeys

Last Updated:Wednesday, January 31, 2024

You don’t need to be a Greek Mythology nerd to know what the hero’s journey is.

That’s because the hero’s journey is an archetype—a pattern of storytelling that has acted as the foundation for everything from crusty old ancient hymns scrawled on giant pieces of parchment paper all the way to modern (-ish) Hollywood blockbusters like the Star Wars franchise.   

The basic premise is that a hero, or heroine, starting from humble beginnings, embarks upon a journey that shakes the foundations of their normal lives, presents them with challenges to overcome, and eventually, they return home with new wisdom and a new perspective of the world.

These types of literary tropes are important because they play a critical role in defining a human understanding of the world. Oftentimes, whether we are aware of it or not, we are playing out, or at least trying to play out, archetypes and patterns that have existed for centuries.  

Everyone wants to be Hercules, Luke Skywalker, Agent Scully, or Buffy the Vampire Slayer. We watch these shows and movies because they let us live the hero or heroine’s journey vicariously, without actually having to get off our butts and widdle some vampire killing wood stakes of our own.

Well, here’s the thing. Brian Chesky, Joe Gebbia, and Nathan Blecharczyk, the three co-founders of Airbnb, want you to have the best of both worlds. They want you to be able to experience the thrills and challenges and self-improvement that comes with the heroine’s journey for yourselves, without any of the danger that comes along with crash landing your X-Wing into the jungles of Dagobah. Airbnb wants to become the Obi-Wan Kenobi/Yoda to your Luke Skywalker—minus the whole getting cut in half by a lightsaber thing.

As Chesky states in an insightful interview with Reid Hoffman, co-founder of LinkedIn, on the podcast Masters of Scale:

“If you do not leave your comfort zone, you do not remember the trip. If you can belong out of your comfort zone and something new happens to you, then there’s going to be a moment of transformation where the person you were in a small way dies and a new, better version of yourself is reborn.”

Airbnb follows this philosophy with its new functionality, simply defined as Trips.

The company has slowly been rolling out Trips across various major cities since it was launched in 2016. Chesky, Gebbia, and Blecharczyk started working on the project when they made a fairly simple realization about their insanely successful peer-to-peer room booking service.

If you think about the common Airbnb experience, it usually doesn’t include just chilling in your room in Mexico City for 7 days straight. Obviously, you want your room to be comfortable and private after you spend a long day walking around, eating fancy churros until you’re about to pass out face first in a park. But the bulk of your trip isn’t usually in your room! If you’re spending the money to go on a trip, you’re probably doing so because you want to experience the culture of a new and unfamiliar place.

More so than ever travelers are looking for an authentic cultural experience. According to travel industry analyst, Henry Harteveldt, the one-size fits all experience has faded:

“It’s formulaic and only focuses on the can be convenient and helpful, but what Airbnb can do is allow travelers to go further into the detail of interests that they are already passionate about.”

So what exactly is Trips? Think of it as an extension of the classic Airbnb experience. Trips is a peer-to-peer cultural experience platform. Airbnb wants to become an end-to-end experience, taking care of every facet of your trip.

Want to take a guided tour through Chinatown? Trips has your back. Is your body feeling all wonky because you’ve been missing your daily spin class during your business trip in Miami? Trips has you covered. The service works essentially the same as traditional Airbnb—it connects hosts with potential customers.

Trips is striving to be a very individual, human experience. It doesn’t make sense to create these general-purpose tour guides for cities, because people are looking to do more than just see the Eiffel Tower or the Statue of Liberty. Instead, the target market for Trips is travelers who want to pursue activities that fall in line with their personal interests, hobbies, and experiences.

Chesky et al., want to handcraft the perfect experience for every single traveler, but that’s not exactly the easiest thing in the world to do when you’re a platform as massive as Airbnb.  

No pain(staking) no gain(staking?)

It might seem challenging, or perhaps even impossible, to incorporate such a personal experience into a service that is purposed to accommodate millions of people. On the other hand, many, including Chesky, would argue that in order to create a service that can scale upwards to millions of people, you first need to create something that doesn’t scale.

The best way to achieve this is to create a personal, tailored experience. Moving one step further, the ultimate experience is figuring out how to best dilute that exemplary experience so that it’s accessible, without sacrificing any of the qualities that make it so perfect.

When the company was first developing the booking aspect of their service, the Airbnb co-founders imagined the absolute most amazing experiences and worked backwards. As Chesky explains:

“What would a ten star check in be? A ten-star check in would be The Beatles in 1964...I’d get off the plane and there’d be 5,000 high school kids cheering my name with cars welcoming me to the country. I’d get to the front yard of your house and there'd be a press conference for me, and it would be just a mindfuck experience. So what would 11-star experience be? I would show up at the airport and you’d be there with Elon Musk and you’re saying, ‘You’re going to space.’ The point of the process is that maybe 9, 10, 11 are not feasible...That’s the sweet spot. You have to almost design the extreme to come backwards.”

These might seem like lofty pipe dreams—and they are. That’s not even mentioning that everyone’s 10-Star experience is probably going to be drastically different. I mean, if you’re afraid of aliens, the idea of blasting off to Mars with Elon Musk might actually be a MINUS 5-star experience. And it could be even worse if you’re also afraid of Elon Musk.

But it’s not like this is a totally new set of challenges for the guys behind Airbnb. After all, for the first phase of the service’s existence, it was only being used by a few hundred people in New York City. The founders knew they had a solid idea for a product, but were still working out how to scale up their services to become a worldwide phenomenon.

That is until they started working with the minds at Y Combinator, one of the biggest and most prolific startup incubators in the world. Their advice? In order to create a product that scales, you first need to master a product that can’t scale.

In other words, you need to carefully craft a product that fills all the needs of your existing customers, without thinking too much about the big picture. That advice seems like a tough pill to swallow when you’re thinking in terms of millions, or billions, but it’s exactly what Chesky and his small team set out to accomplish.

Imagine signing up for this new, interesting sounding vacation rental platform. You’ve got this nice, pretty little apartment right in the hippest area of Brooklyn, and all of a sudden you have the opportunity to make a bit of extra cash by renting it out to vacationers while you’re out of town. So you sign up, make a profile, everything is all good. Then, a couple of days later, the actual founders of that company show up at your front door—they want to meet you, to get to know their users, to see if they can help maximize your, and your guests, experiences. They even want to help boost your profile’s visibility by taking professional pictures of your place.

This is the type of experience that sounds like it might be out of an episode of Black Mirror, and yet, it’s exactly how Brian Chesky and the other co-founders of Airbnb approached the early days of their business.

The co-founders of Airbnb are taking notes from their successful reconnaissance bookings venture and are applying them directly to the Trips platform as well. Take, for example, one of Trips first case studies and success stories, Ricardo.

Airbnb created an advertisement in which, very simply, they wanted to follow someone around on their trip to San Francisco. In exchange, they would have the whole trip professionally photographed. Ricardo applied, Airbnb followed, and the company quickly discovered that Ricardo’s trip really stank. He dawdled around the city, checking out a few landmarks by himself, and spent the rest of his time in seedy bars with locals but not actually talking or meeting anyone. I mean, it kinda sounds like a cool trip if you ask me, but Ricardo and Airbnb were disappointed.  

So, Chesky called him back after the trip was over, and asked if they could curate the perfect trip for him, filled with amazing scenes, experiences, and adventures.  

Reading about the aftermath of Ricardo’s curated trip gives some insight into just how impactful a perfect vacation can be, and on the other hand, just how soul-crushing a bad trip can be.  

Think about it—you’ve hyped up this amazing, relaxing, intellectually-stimulating trip that will allow you to get away from your daily grind, if only for a short time. The last thing you want is for that trip to suck. Because if it sucks, it feels as though you’ve just wasted an opportunity to truly enjoy life.

In the Masters of Scale podcast, Chesky recounts the aftermath of his follow-up meeting with Ricardo:

“I say, ‘How was your trip?’ He says, ‘It was amazing.’ And then I walk away. He yells at me. ‘Brian, one more thing.’ He starts crying. He breaks down, he says, ‘Thank you. This is the best trip Ive ever had.’ I was like, ‘Oh my God. I guess it worked. It really moved him.’ I don’t think anyone ever tried to design an end-to-end experience for somebody like theyre in a movie before and we did it. That became a blueprint. We said we are confident on an unscalable basis that we know how to create a trip that deeply moved somebody that’s better than anything theyve ever experienced. The question is: ‘Can we develop a technology that scales and do it 100 million times?’”

The heroine’s return home

The idea of giving everyone their dream trip is certainly admirable but is it actually feasible? Is this like your dad promising you a pony for Christmas and then you wake up on the 25th expecting to ride off into the sunset and instead he bought you a pair of socks?

So far, anyways, the numbers are promising. According to Airbnb’s reports last year, Experiences is growing much faster than even Airbnb Homes did and receives 1.5 million bookings on an annualized basis, plus about 1,200 host applications per week.

Now, you can experience over 15,000 unique “Experiences” in cities ranging from Boston, Porto, and Medellín to Seville, Prague, Buffalo, and more. It’s like Airbnb is rewriting a more globally, and culturally inclusive script of “This Land is Your Land.”

Trips is interesting because it tries to circumvent one of the major issues with the barebones booking aspect of Airbnb—people taking advantage of the platform with the sole purpose of making a quick buck, undercutting local hotels and without providing any of the comfort, warmth or amenities that are supposed to go hand-in-hand with that 5 Star Airbnb visit.  

Trips strives to truly connect like-minded people to help enrich the interactions between tourists and local. The potential hosts are still vetted by Airbnb, so you’re not going to show up for a painting class and find yourself suddenly embroiled in a trans-Atlantic drug smuggling conspiracy.

The venture also gives hosts the opportunity to expose their services to clientele that might not normally get a chance to see it—for example, Skift investigates Trips deeper by asking hosts how they feel about the new feature. Christopher Pellegrini, a certified shōchÅ« sommelier based in Tokyo, says because of the Trips platforms, he gets to share his vast wealth of knowledge for something that he loves, to a diverse range of people who might never have even considered that shōchÅ« tasting is a thing.

Whether it’s shōchÅ«, pottery, or hot springs—at the end of the day Trips is like the bespoke suit of vacations, offering an opportunity for individualized experiences with an end game of producing happier and more fulfilled travelers.

And hell, the more shared human experiences, the better!