From Ambition to “I’m Enough” | Brian Chesky

**Brian Chesky** (0:00)
My whole life was chasing success, because chasing success made me special, and special made me feel love. And a light bulb went off. I was lonely. I have an addiction, and that was to work. My happiest times in my life were when I was connected, and my most unhappy parts of my life were when I was lonely. But there's one thing I'm great at, it's learning, and learning how to become many different things. Loneliness is a subjective feeling. You have less connection than you need. That's all it is.

**SPEAKER_2** (0:25)
Welcome to the Midlife Chrysalis podcast with Chip Conley, where we explore how midlife isn't a crisis but a chrysalis, a time of profound transformation that can lead to the most meaningful chapter of your life.

**Chip Conley** (0:41)
Howdy, it's Chip Conley, and this is The Midlife Chrysalis. And this is one of the episodes I've most been looking forward to. For those who don't know my story, I joined Airbnb, the little tech company that most people had never heard of, over 13 years ago, to be the in-house mentor to the founders and Brian Chesky, but also to very quickly learn that I was being mutually mentored by Brian. Brian was teaching me things while I was teaching him things. And I've got to say, at 52, with Brian being 31 and the average age in the company being 26, this is actually how I earned the phrase, the modern elder, someone who's as curious as they are wise. But I felt like there was a new definition of success for me. And that definition was defined by, how can I help Brian and his co-founders be as successful as leaders as possible? And how can I help them build a company that can live far into the future? And at the time I joined the company, it was actually very small. And I spent seven and a half years there, four years full time, three and a half years part time.
Somebody who was listening to this episode, and I'm giving you the intro, having already just shot, you know, we just recorded it, said, Chip, you sounded like a proud papa. And I do, I do feel like a proud papa. I'm proud that Brian is still almost five and a half years after the IPO, still the CEO of this company, that's a Fortune 500 company and a $100 billion company in valuation. But I have to say that, you know, you're going to find in this episode that while we will talk about leadership and we will talk about tech a little bit. This is an exploration into Brian Chesky as a human and as a philosopher and as somebody who has evolved into his midlife. And I think it's one of the most transparent and authentic podcast episodes Brian has ever offered and I guess that is a testament to the relationship we have. So I hope you enjoy it and I will be with you at the end to express my three lessons I learned from this episode. Brian.

**Brian Chesky** (2:59)
Hey, Chip.

**Chip Conley** (3:00)
Look at that hair. You got a lot of hair.

**Brian Chesky** (3:02)
I know. I decided to finally grow it out.

**Chip Conley** (3:04)
Yeah. I like it. I like it.

**Brian Chesky** (3:06)
Thank you.

**Chip Conley** (3:07)
Well, what can I say other than it was, gosh, almost exactly 13 years ago that we started spending some time together. And you came over to my back, to my house, and wanted to convince me that I should be joining Airbnb, this little tech company that I was confusing with couch surfing. I didn't know what the hell you guys were doing. And I was, I gave, I said, I'll give you eight hours a week. You convinced me to on 15 hours a week. And within three weeks, I was 15 hours a day. And I realized, shit, I'm fully committed to this.
What was it like approaching me and people like George Tenet and John Donahoe, the CEO of eBay, who I did a call with today? You were, you're really, you've got an amazing appetite for learning from people who have an expertise in a particular area. And you have complete chutzpah to ask them to help you. So tell us, go back to the time when you came to me and why did you come to me?

**Brian Chesky** (4:09)
Well, first of all, Chip, it's, I want to start by saying it's so nice to see you. And every time, when I look in your eyes, I have so many memories, including in this building that I'm in now. And I even in this room we're in, I had meetings with you in this room. And I'm just, it's incredible. Let me start, let me, let me, let me take that as two parts. The first is, I had a lot of chutzpah. There's a lot of things I've struggled with in my life and I had to work on. And we'll probably talk about it. And that's not one of them. For whatever reason, I always had a nerve. I always was like shameless. I had this chutzpah to like seek out the very best. And you know, when I was ninth grade, that meant I sought out the seniors in high school. Because those were like, you know, and when I was in college, I sought out the professors and got their time. And when I came to Silicon Valley, when I was not really very obscure, I sought out kids two years older than me, a little ahead of me. And you work your way up and pretty soon I'm talking to you and these people. So it's just a lifelong pattern I had. I realized, like somebody once told me, asked me, how do you, like one of the things, somebody asked, what is the main thing you've learned how to do since starting up Airbnb? And I said, the main thing I learned how to do was learn. I've learned a lot of things. I'm not sure what I'm an expert in. I'm not the best. I'm a pretty good writer. I'm not the best writer in the world. I'm a pretty good speaker. I'm not a professional orator. I'm a pretty good business leader. I'm not the, I'm a good designer. I'm not Johnny Ive. But there's one thing I'm great at. It's learning and learning how to become many different things. One of the ways I learned was I learned to go to the source. If you were to ask somebody, how do you learn something in 40 hours? They'd say they'd study it for 40 hours. Well, how do you learn 40 things in 40 hours? You can't spend 40 hours on everything. You have to basically be very efficient when you're learning. The most efficient way to learn, I always found was to go to a source or authority. For me, that was seeking out. I find that so many people, the biggest obstacle their success is this voice in them saying, I'm not deserving of this. I always thought, it doesn't cost anything to get rejected. It doesn't cost anything for them to say no. Honestly, I'm not going to take no as an answer. I hope that doesn't offend the person. I never took no from you. I heard about you, because when I started Airbnb, somebody gave me your book. I think you wrote multiple books, actually.