Airbnb CEO Brian Chesky explains how he helped Sam Altman during OpenAI’s 2023 board fiasco

After 17 years, Airbnb’s Brian Chesky is hitting reset—reinventing the business from the ground up and expanding the brand in unexpected ways. Chesky joins Rapid Response to explain why now is the right time for Airbnb’s “great reinvention” and takes us inside his relationship with Sam Altman, revealing previously unheard details about Altman’s brief yet tumultuous dismissal from OpenAI.

This is an abridged transcript of an interview from Rapid Response, hosted by the former editor-in-chief of Fast Company Bob Safian. From the team behind the Masters of Scale podcast, Rapid Response features candid conversations with today’s top business leaders navigating real-time challenges. Subscribe to Rapid Response wherever you get your podcasts to ensure you never miss an episode.

You said recently that Airbnb would undergo the greatest reinvention in the company’s history in the months ahead. Why is that necessary? Can you share any details about it?

For the last four years, what we’ve been doing is really trying to perfect our core business.

We basically asked everyone who didn’t like Airbnb, why don’t you like Airbnb? What are your issues with the service? We were really methodical. We blueprinted the end-to-end experience for guests and hosts. And over the last four years, we’ve made 535 features and upgrades.

I think our core service is better than ever. It’s not ever going to be finished. It’s kind of like if you want to build a skyscraper and you’re a four-story building, you can’t just keep building new floors. At some point, you need to rebuild the foundation so you can hold more floors.

This is the moment where we want to expand the Airbnb model beyond a place to stay.

Most people think ideas are too late. Often Silicon Valley ideas are too early, and we probably weren’t ready to expand beyond our core business until this moment. I think we can take the Airbnb model and bring it to all these different categories of traveling and living.

We’ve had to basically rebuild the app from the ground up to do this. We’ve had to build out entire new functions we didn’t really have before. We had to reorganize the company. We had to become much more collaborative. It’s very rare to get out of your groove at this age. It’s kind of like learning a new language later in life.

It’s a real challenge, but it’s the best kind of challenge. It keeps us young and keeps us from becoming a big old company by having to fundamentally change and reinvent who we are.

But you must have to make tough choices in this, like a one-stop shop. It could sound like sort of a less focused, more catch-all business where you’re in all kinds of things, right? Because you have this community and customer base that you can leverage and introduce to different kinds of experiences and tools. You can’t go into everything.

Yeah, so the governor is three things. Number one, you can’t do everything well at once. You have to focus. You have to pick. Number two, you can only do things you can do well. We can’t do everything well. We should only do things where there’s a reason we do it. We track the number of devices that access Airbnb. That number is 1.6 billion a year. So 1.6 billion devices a year, which could easily, if the average person uses two devices, mean 800 million, close to a billion, people are using Airbnb every year. Think about that. That’s a very big number. Now, we have enough traffic. We could just slap our logo on something that’s not any better than anyone else’s product, and it would sell some, but we don’t want to do that.

If we put our logo on something, it’s because there’s something different, something better, something more authentic, higher quality, easier to book. So, the first thing is we can’t do everything at once well. Number two, we should only do things we can do well and do differently. And the third is, I think Airbnb is known for user interface, great design, and creating a really simple experience. So everything has to be coherent and cohesive.

People use Airbnb to travel, and eventually, they’ll probably use Airbnb in their own city, but they’ll probably use it to explore their community. So if we were to think about that as a workflow, like going on a trip, moving somewhere for a month, that is a coherent way to keep the interface really simple and really cross-selling different things in a way that would make sense to a customer.

So those are, I guess, our big principles.

I’m going to change gears just a little bit. Sam Altman recently said that you helped him during that brief period in 2023 when he was ousted from OpenAI. You saved him from making some mistakes. Can you share anything about that and the sort of advice you gave him?

Yeah, sure. Maybe just to back up, I’ve known Sam for like 16 years because he was with Y Combinator. He was the first big Y Combinator founder, I think, in 2006, and then he became president of Y Combinator. We kept in touch.

He launched ChatGPT November 30, 2022, and the world literally changed in about three to four days. On November 1, 2022, no one was talking about AI other than people interested in AI. By December 5, the whole world was talking about AI.

So it completely ushered in the AI era. At that moment, I told Sam, “You’re basically going to go through everything I’ve gone through in the last 10 years, but you’re going to go through it in like a year.” I said, “You’re going to have a crazy rocket ship, and I’m here if you need help.” At that point, we started meeting every, I don’t know, every couple of weeks or something. I was just giving him advice.

Then it’s the next November, I think it was, and I got a text on my phone. I’m in a WhatsApp group, and everyone said, “Oh, did you hear the news? Sam was fired from OpenAI.” And I’m like, “Fired?” I texted Sam, “What the hell is going on?”

And I was one of the first people who responded to it. And he said, “So brutal. I was fired. I don’t really know why I was fired.” And I was like, “You don’t know why you were fired, but you were fired, and it was made public immediately.” Then the circumstances got even fishier.

I was told that Microsoft was only given a 15- or 30-minute heads up. There was no actual investigation, and Greg Brockman, the other cofounder, was removed from the board immediately. I said, “Okay, I don’t know what happened, but you deserve a fair process.”

I kind of just helped him with what to do over the next three to four days. I gave him quite a bit of advice on PR. I basically told him, “You have to do two things. Tell them what you know and don’t know. Don’t point fingers at anyone; don’t blame anyone. Just tell them what you know and don’t know. Then say, the most important thing is to turn your attention to the employees and make sure they’re taken care of, the company’s taken care of.”

And, ultimately, I think he was going to do all this anyway, but the way he handled it, I think the employees really rallied to his side. The board eventually realized an AI company without AI talent isn’t really a company. 

Essentially, what we did was help bring everyone to the table and realize this is an internet treasure. This is one of the most important companies in the world ever in Silicon Valley, ushering in this AI gold rush. But also, we have to set a good example of Silicon Valley.

We want to show that founders are protected to some extent to ensure fair processes. We don’t want to invite more board activism. We really want to make sure that this really important company is held together because the world really needs this innovation and advancement. People way beyond me were able to find a resolution. I was just trying to be a helpful person. I have no official role in OpenAI. I just tried to keep a company together. At the end of the whole thing, Sam asked me, “How can I repay you?” I told him what Ron Conway and some other people told me when I wanted to repay them for helping me. They said, “Pass it forward,” and that’s what I told him. I said, “I’m not asking for anything other than to pass it on to the next generation.”

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