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Michelle Obama: The Light Podcast

Be a Different Kind of Leader with Brian Chesky

Michelle Obama: The Light Podcast

Higher Ground

Self-improvement, Education, Society & Culture, Relationships

4.49.1K Ratings

🗓️ 21 May 2025

⏱️ 55 minutes

🧾️ Download transcript

Summary

This week Airbnb’s co-founder and CEO, Brian Chesky, joins Michelle and Craig at the table to discuss everything from boosting a business out of the startup phase to dating in search of deep connection. Brian shares stories about Airbnb’s early keys to success (hint: it has to do with breakfast cereal), the evolving responsibility of tech companies in the modern age and how young entrepreneurs can navigate the current tech landscape. Plus, Michelle presses Brian on the dating advice he received from a surprising source during the pandemic. 

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Transcript

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0:00.0

You know, I have to say, Brian, if I'm a single girl out there, and I find out that Brian Chesky is single and I can, like, stay in his house.

0:09.2

Have you ever?

0:11.0

Right to the relationship, Brian, you don't have to be filled pressure.

0:14.3

No, but we've never talked about this.

0:16.2

He just got here.

0:17.4

Have you ever?

0:18.6

Her husband has been trying to set me up before, so...

0:21.3

Yeah.

0:21.8

I'm very, I'm very invested in Brian's love life.

0:26.6

I appreciate it.

0:26.6

I'm doing.

0:27.6

Good. Craig Robinson. Hi. How you doing, dude? Good, niche. How you doing? I am good. You're looking, you... I was going to say you look refreshed.

0:47.3

Thank you. I am pretty refreshed. You look refreshed. You shouldn't be because you still have a little bitty kids.

0:54.5

I know. I know. I should look worn out.

0:57.1

I should stop calling them little bitty.

0:58.8

Yeah. They're not little bitty anymore. And they're almost as tall as me.

1:02.2

Yeah. But yeah, you're coaching doing, still doing all the stuff deep into the.

1:07.8

I'm still coaching. I'm still coaching and still parenting and all that kind of stuff. So I should look haggard,

1:12.9

but I am always so excited to do this with you. You sent, or Kelly sent a picture,

1:20.6

Austin's starting to drive? Yes. Oh, this is a good story. So you remember the green car?

1:31.3

The green car that's like a hundred years old?

1:40.1

It's a 1999 GMC. You talk about an old man keeping a car forever. Well, you know, I just, I'm my dad's kid. There's no need to get a new car when your old car is running perfectly.

...

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