A few years ago, I wrote in the Wall Street Journal Speakeasy blog about the “billion-dollar app that we’re all born with” and even made a short video about it. The app in question—no surprise to readers of this site—is our natural-born aptitude for asking questions. An aptitude that life often conspires to tamp down. My mission is to shine a light on the great power of questioning and help people build up this muscle.
In that article I mentioned Airbnb as a model “questioning company.” When researching A More Beautiful Question back in 2013, I originally became intrigued by the start-up couch-surfing company when I read about how they started by exploring a great question: Why should you be stuck without a bed if I’ve got an extra air mattress? The founders of the company noticed that whenever the design convention came to San Francisco, it became almost impossible for visitors to find a place to sleep because all the hotels were booked. But at the same time, lots of people had space and an empty couch or unused air mattress that could potentially solve the problem if there was a way to rent that space out. In my interviews with co-founder Joe Gebbia I learned that the company’s early days and exponential growth were actually fueled by a series of questions, making them a real-time poster child for my “beautiful questions” process, which takes place almost organically within the most innovative companies.
In order to capture this organic process so that we all can profit from how innovative companies use questioning, in my book I profile at length Joe Gebbia and Brian Chesky’s trajectory from jobless young San Franciscans with a decent apartment to leaders of the sharing economy. If you’re curious how Airbnb’s story looks via the lens of “questioning,” below is an excerpt from A More Beautiful Question that tells that story.
EXCERPT from A More Beautiful Question
Why should you be stuck without a bed if I’ve got an extra air mattress?
In the fall of 2007, Joe Gebbia and Brian Chesky had one question uppermost in their minds, and it wasn’t a beautiful one. “How were we going to pay the rent? That was the main issue at the time,” Gebbia recalls. He and his roommate Chesky had no jobs, and not much money. But they did have a decent San Francisco apartment with a place to sleep and a roof over their heads. Which was more than could be said for many of the people coming to town for a local business conference—the city’s hotels were all booked, and conference-goers were desperate for a place to stay.
This situation (which Gebbia and Chesky previously had experienced firsthand themselves, as visitors to prior conferences) didn’t make sense to them: Why can’t we find a place for these people to crash for a night or two? Which then led to: Why not our place?
Gebbia and Chesky got hold of three inflatable air mattresses. They could have simply run a cheap classified ad, rented out their airbeds for a modest fee during the conference, and picked up enough money to cover a small portion of that month’s rent. But almost immediately, they were starting to think bigger about this idea and asking all kinds of What if questions, such as: What if we provide more than just a mattress to sleep on? They didn’t have much to offer but they threw in a modest breakfast (how modest? Pop tarts!) and sightseeing tips. And rather than just put a listing on Craigslist, Gebbia and Chesky (who both had a design background) thought: What if we create our own website?
They did all of this, rented out the three mattresses to three inpiduals who didn’t know each other and everyone enjoyed the experience. At this point, Gebbia says, they were starting to think, Why not make a business out of this? What if we could create this same experience in every major city?
Here is where the two dreamers ran head-first into conventional wisdom. Initially, no one, outside of Chesky, Gebbia, and a third partner they brought on, thought this was an idea that made business sense or was worth supporting. Paul Graham, a renowned angel investor in Silicon Valley who runs the startup incubator firm Y Combinator, believed, quite simply, “No one would want to stay in someone else’s bed.”
The idea that would eventually become Airbnb was challenging a basic assumption: That you needed established, reputable hotels to provide accommodation for out-of-town visitors. Of course, those paying close attention might have noticed that just a few years prior to this, lots of people held similar assumptions about cars—you could buy them, you could rent them, but there was no practical way to share them. Then an entrepreneur named Robin Chase asked Why not?, and subsequently introduced ZipCar.
Gebbia told me that part of the reason he and Chesky believed this was a problem worth solving—the reason, he suspects, that they saw what others missed—was that they had been on both sides of the problem. “We knew what it was like to come to town needing a place to stay, and we knew what it was like to have extra space that we needed to rent,” he said. “So we connected those two dots. In retrospect it makes complete sense—but at the time, no one else had connected those dots.”
Gebbia and Chesky had a kind of “rebel” attitude that goes with successful questioning. It’s one thing to see a problem and to question why the problem exists, and maybe even wonder whether there might be a better alternative. It’s another to keep asking those questions, even after experts have told you, in effect, “You can’t change this situation; there are good reasons why things are the way they are.”
Gebbia and Chesky had to overcome that initial resistance by continuing to push forward on their original question (about whether they could expand that first hosting experience into a business), and they were propelled by new questions at each step of the way. They wondered: What if we take this idea on the road, and test it in another city? With the 2008 Democratic presidential convention in Denver, they found the perfect place to launch—lots of people coming into town, not enough hotels. But how would those visitors, and the people with space to rent, learn about Airbnb? Gebbia and Chesky couldn’t afford ads; so they had to make news. The founders knew that the news channels would be doing stories about how crowded and overbooked Denver was. They pitched Airbnb as a “solution story” to news producers and ended up on CNN. The bookings came in and the Denver launch was a success.
But Gebbia says they kept questioning, kept iterating and refining the model for another year before the founders felt they had it right. They used the site themselves, stayed in rentals, and asked, What’s working here and what’s not? When they noticed, for example, that exchanging money with apartment hosts was awkward—“It just felt like the whole experience was relaxed and fun, until it came time to pay,” Gebbia recalls—this spurred them to ask, What if you could pay online? When they noticed that many of the visitors to their site were asking about foreign cities, this led to a big question: Why are we limiting this to the US? What if go global? Within less than two years, they were in more than 100 countries, doing a million bookings, and flush with more than $100 million in investment dollars. They had even won over early skeptics like Y Combinator’s Graham, who became one of their seed investors.
These days, Gebbia and Chesky are asking a whole new set of questions about whether it’s feasible to create a “sharing economy.” At the core of this idea is the fundamental question: Why should we, as a society, continue to buy things that we really don’t need to own? (Consider, for example, that the average power drill in the US is used a total of 13 minutes in its lifetime.) As Gebbia notes, we’ve spent decades accumulating “stuff” in the modern consumer age. “What if we spent the next hundred years sharing more of that stuff? What if access trumped ownership?”
Whether or not Airbnb, joined by others, will be able to successfully lead that ambitious “sharing economy” movement is an open question, and one that—even more than the earlier questions about whether people would be willing to share homes and beds—aggressively challenges assumptions about how our economy works, the extent to which people are willing to change ingrained behavior, and whether sharing even makes sense as a viable business model.
What’s clear, though, is that the success Gebbia and Chesky have already achieved is rooted in their willingness to challenge assumptions and to believe that everything is subject to change—regardless of what conventional wisdom holds. I think of this brand of questioning as a sub-category of Why questions that could be considered “challenger questions.” They have a certain attitude about them: restless, rebellious, skeptical of convention and authority. As in:
- Why should we settle for what currently exists?
- And why should I believe you when you tell me something can’t be done?
