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Brian Chesky

👤 Person
1017 total appearances

Appearances Over Time

Podcast Appearances

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And I basically had my day job during the day. And then I had my night school with the former president where I would get these assignments. But it changed my life. By the way, he's the one who told me to reach back out to my old friends. He said, I have a circle of 10 to 15 really close friends

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And I thought to myself, I guess I technically have 15 friends, but if I texted any of them or called them, I have to get them up to speed in my life. So therefore, I'm not maintaining those relationships. But I think the thing that President Obama taught me was to be more intentional. He literally said like so many leaders are like self-driving cars. Use that analogy. They're not intentional.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And I thought to myself, I guess I technically have 15 friends, but if I texted any of them or called them, I have to get them up to speed in my life. So therefore, I'm not maintaining those relationships. But I think the thing that President Obama taught me was to be more intentional. He literally said like so many leaders are like self-driving cars. Use that analogy. They're not intentional.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And I thought to myself, I guess I technically have 15 friends, but if I texted any of them or called them, I have to get them up to speed in my life. So therefore, I'm not maintaining those relationships. But I think the thing that President Obama taught me was to be more intentional. He literally said like so many leaders are like self-driving cars. Use that analogy. They're not intentional.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

They're like a car, but they never put the destination in. So they're just driving somewhere. And he made me really be intentional about like, what do I want out of my life, out of the company? I ended up writing down a whole bunch of principles. I tried to institutionalize them for the company. I think it made a really, really big difference.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

They're like a car, but they never put the destination in. So they're just driving somewhere. And he made me really be intentional about like, what do I want out of my life, out of the company? I ended up writing down a whole bunch of principles. I tried to institutionalize them for the company. I think it made a really, really big difference.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

They're like a car, but they never put the destination in. So they're just driving somewhere. And he made me really be intentional about like, what do I want out of my life, out of the company? I ended up writing down a whole bunch of principles. I tried to institutionalize them for the company. I think it made a really, really big difference.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And he kind of taught me a little bit how to think more deeply. Because I think As an entrepreneur, there's an element of impulsiveness, spontaneity that's important.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And he kind of taught me a little bit how to think more deeply. Because I think As an entrepreneur, there's an element of impulsiveness, spontaneity that's important.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And he kind of taught me a little bit how to think more deeply. Because I think As an entrepreneur, there's an element of impulsiveness, spontaneity that's important.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

Yeah. You need to like have an idea and you need to do things. It's actually important when you first have an idea not to overthink things. And so you just go and you go and you don't overthink. Because if you overthink and you're like get stuck in business plans, nothing ever happens. An entrepreneur has to do a thousand things a thousand times. The problem is when you never make the shift.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

Yeah. You need to like have an idea and you need to do things. It's actually important when you first have an idea not to overthink things. And so you just go and you go and you don't overthink. Because if you overthink and you're like get stuck in business plans, nothing ever happens. An entrepreneur has to do a thousand things a thousand times. The problem is when you never make the shift.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

Yeah. You need to like have an idea and you need to do things. It's actually important when you first have an idea not to overthink things. And so you just go and you go and you don't overthink. Because if you overthink and you're like get stuck in business plans, nothing ever happens. An entrepreneur has to do a thousand things a thousand times. The problem is when you never make the shift.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And at some point you have to go from an entrepreneur to a CEO.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And at some point you have to go from an entrepreneur to a CEO.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And at some point you have to go from an entrepreneur to a CEO.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And a CEO can't operate that way. A CEO has to realize, like, I'm responsible. I'm a steward for a community of hundreds of millions of people. Thousands of people's jobs depend on me. I got to actually think, like, if I do this, what are the second or third order consequences? We as entrepreneurs and tech folk, we're not trained to do that. Yeah. And so I think it's hard to make that shift.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And a CEO can't operate that way. A CEO has to realize, like, I'm responsible. I'm a steward for a community of hundreds of millions of people. Thousands of people's jobs depend on me. I got to actually think, like, if I do this, what are the second or third order consequences? We as entrepreneurs and tech folk, we're not trained to do that. Yeah. And so I think it's hard to make that shift.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

And a CEO can't operate that way. A CEO has to realize, like, I'm responsible. I'm a steward for a community of hundreds of millions of people. Thousands of people's jobs depend on me. I got to actually think, like, if I do this, what are the second or third order consequences? We as entrepreneurs and tech folk, we're not trained to do that. Yeah. And so I think it's hard to make that shift.

IMO with Michelle Obama and Craig Robinson
Be a Different Kind of Leader with Brian Chesky

That's actually profoundly student insight. And I would... Excuse me. Did you hear what he said?