We attended two Brian Chesky talks in two days. Here’s what we learned.

Photo credit: Erica Price

We promise we’re not following Brian Chesky around everywhere. 

But when the Co-Founder and CEO of Airbnb (a Tech:NYC member!) told us he was spending a few days in New York recently, we decided to go all in.

Our first Chesky event was a power-packed stage when he spoke with AlleyCorp Founder and CEO Kevin Ryan at an event hosted by Tech:NYC with our members, AlleyCorp and Company Ventures, in a room filled with ~150 founders, venture capitalists, and other tech leaders. 

The next day, we attended another all-star session with Chesky, held at Ramp (*another* Tech:NYC member), to discuss the “Art of Hiring.” 

At both events, Chesky clarified what he meant by his viral “founder mode” talk at a Y Combinator event last month. 

“No one is born a good CEO,” Chesky said. That is, leadership isn’t intuitive. It’s one thing to found a company, it’s quite another to run one. But what does that mean in practice? 

Let’s take a deeper look: 

Four things we learned from Brian Chesky’s New York tour:

1. Being a good CEO is not the same as being a good founder.
“I am not aware of one CEO in the last 100 years that was good the day they started,” Chesky said. Being a good CEO is not the same as being a good founder.

As a founder, “You want to get in a car and you want to be able to turn left, and the car turns left, and you want to turn right, the car turns right. And that's what it's like to be a founder,” Chesky said. “And then a CEO, it's like you're in the back of a bus and you're like, turn left, and nothing happens. And they explain to you why the car can't turn left, but we'll be able to turn left in like, a mile or two, and it just makes you freaking crazy.”

So, how do you become a good CEO? “Hire great people and be in the details with them,” Chesky said, repeating the line for emphasis. “Don't abdicate responsibility, because leadership is presence, not absence.”

But isn’t that… micromanaging? No, Chesky said. Being in the details with employees does not mean telling them what to do. It means partnering with them to ensure work gets done efficiently and meets the standards of the CEO.

2. How a company responds to a crisis can shape its identity.
In 2019, right before Airbnb went public, Chesky wanted to reorganize the company. But since this was just before its IPO, he hesitated. Then COVID hit and Airbnb lost 80% of its business. He quickly realized that this was an opportunity to rethink the way he runs the company. 

Chesky quoted the late Intel founder ​​Andy Grove: “Bad companies are destroyed by a crisis. Good companies survive a crisis. But great companies are defined by a crisis.” 

Chesky switched from running a “divisional organization” to running what he calls a “functional organization.” 

“We said we’re the Navy SEALS, not the Navy. We want a small, lean, elite, highly-skilled team,” Chesky said.

That mentality has enabled him to run a large company, with thousands of employees, like a smaller, more efficient one.

“I don't think of myself as running a 7,000-person company. I think of myself as running a 100-person company,” Chesky said. “When I pull those 100 people in, we try to create a shared consciousness where we can finish each other's sentences. And if we can do that, we feel like a startup.”

3. CEOs should be involved in hiring decisions.
Chesky said he interviewed the first 400 people at Airbnb, and he wishes he did more. 

Somewhat half-jokingly, he said, “I think [CEOs] should interview every candidate until the recruiting team stages an intervention. Once they stage an intervention, [the CEO] should interview for two more years after that, until everyone threatens to resign.”

The reason goes back to lesson No. 1 – good CEOs are in the details.

4. When hiring, vet the references.
Every potential hire is “guilty until proven innocent,” according to Chesky. That is, hiring managers should presume a candidate is not the right fit for their company, and the candidate should have to prove that they are. “You need evidence to hire them, not evidence to eliminate them as a candidate,” he said.

Of course, references are a big part of this “detective work,” and Chesky even prioritizes references over interviews. What are some techniques when it comes to talking to references?

First, you should vet the reference. “B players say other B players are awesome. So you have to qualify the references,” Chesky said. 

References will also generally not want to say the person they’re referring is a bad worker or bad employee. 

To get around that, first mention that everything is off the record. Then, ask the reference who the best person is that they worked with. “If they don't say [the candidate’s] name, they're not one of the best,” Chesky said — and you probably shouldn’t hire them. 

***

Chesky’s two talks were filled with simply too many insights to fit into this blog post. 

There were tips on how to close a candidate (“try to talk them out of the job”), how much money to raise (“raise as little money as possible”), and how to motivate employees (“a great job of a leader is to see potential that they don’t see in themselves”).

Chesky often referenced CEOs who inspired him, especially Steve Jobs. It was clear by the end of both talks that to lead a company as successful as Airbnb is today, you should always be learning from the successes – and the mistakes – of other leaders. Chesky is no exception.

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Photos credit: Erica Price