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An Interview with Airbnb CEO Brian Chesky

An Interview with Airbnb CEO Brian Chesky
By Jason Aten • Issue #48 • View online
Earlier this week, I had a chance to talk to Airbnb CEO Brian Chesky about a range of topics, including new features the company is introducing. First, however, we talked about the company’s move to let its employees live and work anywhere, and how he came up with a plan that made sense for Airbnb. 

Image courtesy Airbnb/Jessica Chou
Image courtesy Airbnb/Jessica Chou
Airbnb is in an interesting position since not only is the company putting in place a policy that allows its team to be fully remote, but it has also seen the way people are using its product to do just that. Every company is trying to figure this out, and a lot of them have defaulted to what has become known as “hybrid work.”
In many cases, that means employees are required to be in the office three days a week while working from home the rest of the time. According to Chesky, that form of hybrid work isn’t going to work.
What a lot of people did is they create a thing called hybrid. And hybrid was two days a week or three days a week in the office–which kind of doesn’t give you a lot more flexibility than the old world. I thought maybe there was a different form of hybrid. Maybe instead of asking you to come in three days a week, which I don’t think will work because three days a week will become two days a week, and two days a week will become one day a week, and then everyone comes in the office a different one day a week. And so I thought maybe there was a different form of hybrid, where we combined the efficiency of zoom with the infrequency, but the meaningfulness of interpersonal interaction by getting together one week a quarter. And frankly, if that’s not enough, we can adjust it.
For a lot of companies, it seems like the default assumption is that employees need to be back in the office for at least some structured amount of time. Largely that’s because the people who make decisions about how employees work are usually people who have spent their entire career working in an office.
“Most of the people saying that they want everyone back to the office are over 50,” Chesky says. “There’s just a demographic thing, like the older you are, the more inclined you are to be uncomfortable with the idea of flexibility and digitization. I understand that. It’s a generational thing.”
That doesn’t, however, mean it has to be that way. A better version of hybrid work, according to Chesky, is that the default assumption about where you work is that you’ll be wherever you work best. For most people that’s probably home, or an Airbnb in some far-off, inspiring location. Chesky himself has been working from different Airbnbs for the past few months. 
Then, companies can bring people together for extended periods, a week or two, to do the things you can’t do virtually, like build meaningful relationships with your team. That doesn’t have to be at an office–in fact, it’s probably better if it isn’t. If your goal is to create relationships and connections with your team, take them somewhere that is likely to happen. 
One of the most interesting things about our conversation is the reason Chesky is so bullish on giving employees the flexibility to live anywhere. For Airbnb, it means the company can recruit the very best people without worrying about whether they’re willing to relocate.
The best people don’t live in New York, they don’t live in San Francisco, the best people live everywhere. And some of them are in New York and San Francisco, but they’re really everywhere. And so as a CEO, I have to make a calculation. If I limit my talent pool to a radius near my office, does the increase in productivity of them being near my office overcome the lack of talent I can hire? In other words, if I can hire someone in Ohio, and they are twice as good, that means the person near me has to be twice as productive. Otherwise, I’m at a net loss.
At the end of the day, I think talent wins, I think ultimately, people are going to make a calculation, that the efficiency of being in close proximity is less than the efficiency of having more capable people if they’re dispersed, because ultimately, every company is in the market for talent.
It’s worth mentioning that Chesky has the data to back it up. He says that despite the pandemic, the company had its most productive two years ever. That came while his team was working remotely, which gave him the confidence to make it the default.
A lot of that productivity came in terms of improving the product. Chesky told me Airbnb made 150 changes to the product just last year alone. Today, however, Airbnb announced what Chesky describes as its biggest upgrade yet, letting you search not just by destination, but by type of property. 
Want to stay in the coolest treehouse? Now, you can search for treehouses. You can do the same for National Parks, or great pools, or cabins, or any one of a number of categories. In fact, Airbnb has categorized all of its listings to give users a far better search experience. And, for travelers who want to stay longer, Airbnb is allowing you to split your stay at multiple locations within one search. 
The bottom line is that Airbnb is making the product better at the same time it’s focused on making its company better for the people who work there. I don’t think that’s a coincidence at all.
“The last thing I’ll just say is the word technology basically means the word change,” Chesky said. “And if you’re unwilling to change, then you’re basically saying you won’t be around the future and we intend to be around for a long time to come.”
The End of the iPod
On Tuesday, Apple announced that it was discontinuing the iPod touch. In some ways, the announcement wasn’t particularly surprising aside from the fact that I’m pretty sure most people didn’t even know Apple was still selling the iPod touch (I didn’t). In that sense, killing off a product no one even remembered you were making is a bit anticlimactic. Now that we all use iPhones, there hasn’t been a compelling reason to buy an iPod touch for years.
At the same time, the announcement is bittersweet because it represents the end of a product that–more than almost any other–completely transformed the way we use technology. No, not the iPod touch. The iPod. 
Since it was introduced in October of 2001, Apple sold more than 400 million iPods. That makes it the company’s second-most successful product ever, after the iPhone, which–having sold more than 1.5 billion devices–isn’t just Apple’s most successful product, it’s the most successful product, ever.
You can draw a straight line between the success of the iPod, and that of the iPhone. In fact, according to Tony Fadell, the man often referred to as “the father of the iPod,” there would have been no iPhone without the iPod. 
Joanna Stern
“If we didn’t do the iPod, the iPhone wouldn’t have come out. The iPod brought us confidence. It brought Steve confidence that we could do something outside of the map and that we could actually continue to innovate in new areas.” - @tfadell https://t.co/yBUoe3yrmj
Look, at the risk of making a dramatic understatement, Apple was a very different company 21 years ago than it is today. The month Apple released the iPod, it announced it lost $25 million the previous year, on a little less than $6 billion in sales. In its most recent quarter alone, the company made $25 billion in profit. The big difference is obviously the iPhone.
That wouldn’t come for another six years, however. Steve Jobs, the company’s iconic founder, had returned less than four years earlier and was in the middle of a dramatic effort to make Apple relevant. 
He had a hit with the iMac, the colorful all-in-one desktop computer that made computers fun and playful. By 2001, Apple had sold 5 million iMacs, but sales had started to slow. The iMac might have been the product that saved Apple, but it desperately needed a follow-up act. 
Then, came the iPod.
To be fair, the original iPod wasn’t an immediate hit. First, it was expensive. Second, it required FireWire, which meant you could only use it on a Mac. In fact, a Windows-compatible version of iTunes, the software you needed to sync your music to an iPod, wouldn’t come out until a year later
Steve Jobs, famously, was against Apple making iTunes available on Windows, but once it did, sales took off. Millions of people who previously thought of Apple as a maker of quirky computers for nerds and enthusiasts suddenly saw the company as cool. There were colorful ads with silhouettes wearing white earbuds everywhere. Compared to the competition, the iPod was better in basically every way.
In six years, by 2007, the company had sold 100 million iPods. That year, of course, Jobs stood on a stage and introduced the iPhone. The iPhone, of course, is the reason the iPod died, even if it took a while. Apple made maybe the most important decision of any company when it was willing to cannibalize its most successful product for the sake of its future. That future worked out pretty well. Today, the iPhone has made Apple the world’s most valuable company
This brings us to maybe the most important aspect of Apple’s announcement. As critical as the iPod was to Apple 21 years ago, it’s mostly irrelevant today. No one buys iPods unless they collect vintage electronics at this point. Partly that’s because no one is downloading individual music tracks to sync to their devices. Everyone just uses streaming services.
For that matter, everything you could do with an iPod is better on an iPhone. It’s the one device to rule them all. 
Despite the fact that for millions of people, the iPod was the thing that introduced them to Apple, keeping it around purely for the sake of nostalgia doesn’t make much sense. Apple is the iPhone company now. You have to give the company credit for being willing to let go of what, for 21 long years, has been one of its most endearing products. 
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