Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire) — searchlore

Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Lenny's Podcast

Published Aug 3, 2025

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0:00

Let's paint a picture of just what it was like to join Airbnb in your 50s.

0:00

I was mentoring Brian, but he was also my boss. I was 52. The average age was 26.

0:05

I had to be both wise and curious and often the dumbest person in the room.

0:12

So, it's great to be in founder mode.

0:12

It's not as great to be working for someone in founder mode.

0:16

Brian assumed everybody else was going to work at the same pace and duration.

0:21

His point of view is like, hey, we're having a meeting in the office tonight at 10:00. You know, be there.

0:26

Everyone's talking about we got to make the product better.

0:26

We got to optimize this button and improve conversion.

0:30

Isn't the product the homes and the apartments?

0:34

Jobat said no product in the tech industry is something different.

0:34

I just said, listen, let's get some older people who are hosts in here.

0:38

This whole story is a really good example of the value of having folks that are older.

0:43

When you have older brains connecting the dots, younger team members being really fast and focused, it's brilliant.

0:48

And people won't notice your wrinkles as much as they'll notice your energy.

0:53

The Airbnb experience led you to starting something called the modern elder academy.

0:57

So if you think about the caterpillar to butterfly journey, midlife is the crystallis. Midlife is not crisis.

1:02

I'm happier today at 64 than I was at 47 when I was going through my flatline experience.

1:07

Well, let's back up a little bit.

1:07

This near-death experience today, my guest is Chip Connelly.

1:13

Chip is one of the most extraordinary and interesting people that you'll ever meet.

1:18

He was a founding member of the board of Burning Man.

1:18

He was on the board of the Eselin Institute in Big Su.

1:22

At 26, he started a hotel chain called Jadviv, which went on to become the second largest boutique hotel chain in the US.

1:28

After selling it, Brian Chesy personally recruited Chip to join Airbnb to help Brian and the company transform from a fast growing startup to the world's most valuable hospitality brand.

1:39

After leaving Airbnb, where he was known as the modern elder, Chip started the Modern Elder Academy, now known as MEA, the world's first midlife wisdom school with large, sprawling, beautiful campuses in Baja and Santa Fe.

1:50

He's also written seven books, given a TED talk, and is just a genuinely interesting and amazing human and friend.

1:56

In our conversation, we explore how to be successful in tech as you age.

2:02

What he's learned working with and for Brian Chesy, including a lot of real talk, how to build a great culture at your company, his near-death experience, and how it changed the trajectory of his life, and so much more.

2:12

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2:21

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2:37

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2:37

With that, I bring you Chip Connelly.

2:43

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4:34

Chip, thank you so much for being here and welcome to the podcast. Oh my god, Lenny.

4:34

I I sort of feel like I'm your father who's so proud of his son has done.

4:39

My son has done so well and I I like to talk about tell all my friends about you. Wow. Uh I am honored.

4:47

Uh I'm happy that I'm making you proud, Chip, and I feel I feel the same in reverse.

4:52

Uh we got to work together for many years at Airbnb.

4:52

I got to learn a ton from you.

4:58

Uh I'm really excited that more people are going to get to learn from you from this conversation.

5:02

you from this conversation. I'm thinking that the way that we break up this conversation is kind of break it up into three parts which are kind of the three arcs of your career and the three parts are your uh early career building your time at Airbnb where we got to work together and then talking

5:19

through what you're working on now the modern elder academy I actually want to start with the middle chapter I want to talk about Airbnb where we got to work together let's paint a picture of just what it was like for you to join Airbnb in your 50s uh surround ed by a bunch of 20some 30somes reporting to Brian Jesy who is I don't know in his 30s. What was that like? So yeah, What was that like?

5:35

So yeah, I I wasn't planning on doing this.

5:42

I I got a call uh from a woman named Natalie Tucci who worked at Airbnb and said I we Brian Chesy and I have been talking about having you come in and give a talk. Are you open to that?

5:55

And I was like well what is Airbnb?

5:55

This was uh 13 years ago.

5:55

This was I think it was the end of 2012 and then Brian called me and said, "Listen, we really want you to come in."

6:08

And so I came in and gave a talk about innovation and hospitality.

6:08

And and I think I I didn't realize it was sort of a a a dress rehearsal for Brian to sort of see whether the younger crowd there um I was 52, the average age was 26 would, you know, feel good about, you know, an old geyser like me with a bricks and mortar boutique hotel background uh talking about the industry that Airbnb was disrupting.

6:37

Um, and as it turns out, people liked me.

6:37

And, um, so, uh, Brian said, "I want you to come in for and work 15 hours a week as a consultant.

6:44

I want you to be my in-house mentor for both me and Joe and and Nate."

6:49

And and I said, "Okay, you know, 15 hours a week is great."

6:55

And then, uh, within three weeks, it was 15 hours a day.

7:00

And and Brian and I was saying to Brian, you know, you're actually not paying me anything.

7:04

Um they he gave me uh a little bit of stock that would would vest in six months and I said like I don't know that this deal is working for me.

7:12

Um this is you you it seems like the company needs me a little more than you said and and he said yeah I got you.

7:17

I just wanted you to get in here and see like what you could do.

7:23

And long story short is I ended up going full-time and um it was hard at first, Lenny, because I didn't understand the tech lingo.

7:32

I I didn't have any background. I was 52.

7:39

I'd never worked in a tech company before.

7:39

I was mentoring Brian on leadership, but he was also my boss.

7:44

I was the um head of global hospitality and strategy.

7:44

but he was also my boss. I was the um head of global hospitality and strategy. uh so which mess meant initially I was in charge of all the hosts in the world over time that like you know that meant a lot more things too I I was involved in mo many parts of the business definitely not

8:02

the technical parts but I think the hardest thing for me is was just that initially when people were talking about product and Joe said you know I'm the chief product officer and I'm like well isn't the product isn't the product the homes and the apartments and Jobot said no product in the tech industry is something different. And so I had to be both wise and curious and often the dumbest

8:20

And so I had to be both wise and curious and often the dumbest person in the room.

8:27

And that was uh it required me to have a certain amount of humility as well as to be reporting to a guy 21 years younger than me, Brian.

8:32

That actually the point you're making there about what is the product?

8:37

I I asked uh Laura Hughes, formerly Laura Modi, what to talk to you about, who we got to work together.

8:42

She's the CEO of Bobby now.

8:42

uh you work closely with her at Airbnb and she said this was the thing that stuck with her most about working with you is coming in and and everyone's talking about we got to make the product better.

8:51

We got to optimize this button and improve conversion and product product and you're just like what is like what is the product?

9:00

I thought the product of Airbnb was the hosts and the experiences and the trips and I think that shows the value of someone like you coming in with different experience and also older and helping us communicate differently to hosts who also don't understand.

9:10

Well, there's an interesting thing also, Lenny, and you you know this, the difference in age between our hosts and our guests was probably about 10 years maybe.

9:21

And over time, it actually got higher um because we started actually reaching out more uh aggressively to you know, boomers and and Gen Xers to be hosts.

9:33

And so you had I remember one point um and again, let's get into product talk here.

9:33

I remember one point that there was a conversation that was going on about taking Airbnb so it was mobile only.

9:40

Um, I mean, partly because back in the day, the two sharing economy darlings were Uber and Airbnb.

9:47

And of course, Uber was pretty much a mobile only app.

9:54

And Airbnb started as non-mobile and then went mobile.

10:01

And then I was like, "Oh, wouldn't it be interesting if everything was mobile?"

10:01

And at some point, I just said, "Listen, let's get some older people who are hosts in here to see how well they will be versed in in in managing their listing purely on mobile."

10:12

And so there were times where I was a voice for older uh users in this case hosts um that was helpful to you know guys and women in their 20s who are the engineers and designers and product managers and um I always liked working with you.

10:35

I want to just compliment Lenny um for a minute. How sweet is that?

10:35

because and we did a lot, you know, we were we did a lot of different things together.

10:40

And what I appreciated was you you had a humility to you that was different than a lot of the other product managers.

10:45

There's other product managers, I'm not going to mention their names, and there some of these some of these product managers were very good.

10:55

There were other product managers though who I found it sometimes hard to work with because they expected me to know as much as they did.

11:00

And you know, I guess it would be the if the opposite side of that would be um an older manager expecting a younger manager to have as much emotional intelligence because emotional intelligence on average is something we get better at as we get older.

11:18

So I think the key for me to work in that environment and make it work was to not pretend to know things I didn't know.

11:25

It was to have a sense of humor and humility in how I operated.

11:32

And it was to show respect and hope that I got in return.

11:32

And I don't know if that you felt that way, Lenny.

11:38

I, you know, that's that's the try the kind of environment I tried to to embody there. Absolutely.

11:42

There's a couple of threads there I want to follow.

11:42

One is just working for Brian.

11:48

A lot of people talk about founder mode and the power of founder mode. It's so great.

11:54

And guess who like you know populated that recently? That was Brian. Exactly.

11:54

Uh so it's great to be in founder mode.

12:01

It's not not as great to be working for someone in founder mode.

12:01

Often a very challenging place to be. Yes. You reported to Brian.

12:06

Uh also you were just your own boss basically your entire career.

12:12

You never really had to report to someone before.

12:12

Also he was in his 30s, you're in your 50s.

12:17

What was it like working for Brian?

12:17

Uh you know like the more real you can be the better because a lot of people always talk about here is like I was wonderful. I learned so much.

12:27

Just like what was that experience like?

12:27

What did you learn from working for someone like Brian?

12:30

Well, let's start with the fact that it I would never have gone to work for Airbnb if I didn't believe in Brian because quite frankly when Brian approached me and we started talking about I was like I wasn't sure I liked the the business model all that well as a hotel year.

12:40

So I had to believe in something beyond the business model because I wasn't sure that this the business model would work.

12:50

Although soon after joining I saw the numbers I was like wow this is working pretty well.

12:54

But I believed in Brian because the thing that Brian showed up with initially was just a curiosity and an appetite for learning.

13:00

You know, I remember back in 2011 when the, you know, the big debacle happened with um the the apartment getting uh trashed by a guest and and so Brian decided he was going to go to find, you know, George Tennant, the the former head of the CIA.

13:20

And so like Jo Brian would go to experts and and say to the expert, I don't know what the hell I'm doing.

13:27

And um he did that with me when it came to hospitality.

13:27

So I appreciated that a guy who had a lot of hubris, and Brian definitely has a lot of hubris, could also have the humility to to say, I want to learn more about this.

13:40

So it's sort of a growth mindset.

13:40

What was hard with Brian is I'd say three things.

13:47

Um, number one is Brian assumed everybody else was going to work at the same pace and duration, you know, and he still has this issue.

13:56

I mean, the beautiful thing about Brian is he's been very honest in the last couple years on podcasts about his workcoholism and about the fact that the way he lives his life is not like other people.

14:09

But back when I joined, you know, his point of view was like, hey, we're having a meeting in the in the office tonight at 10:00, you know, be there. It's like, really?

14:19

No, I don't I don't think so.

14:19

But so so I think the the the fact that Brian assumed everybody else was was as one-dimensional in their focus as him was at times a problem, especially for a guy like me who was I was in a stage in my career where like I have a lot of interests. Um, so that was one.

14:39

Number two is Brian admires and admired in back then Steve Jobs so much that there was a sense that as a guy who came from the product world uh from the Rhode Island School of Design, he knew better than anybody else.

14:58

And so there was this you know one of the challenges for a CEO sometimes and I this was my experience in my 24 years of running Viv, my boutique hotel company is it feels good when you feel needed.

15:12

Um, and to come into a room and sort of see something and then point out the things that are wrong makes you feel good.

15:20

And if you don't have emotional intelligence, you can that process can really piss people off or or demotiv demotivate people.

15:34

And in Brian's case, I didn't have to deal with that too much because he didn't understand when I was starting.

15:40

It was really I was in charge of the hosts around the world.

15:44

And so quite frankly, the idea of what's the psychology of the host?

15:44

What's a host entrepreneur like?

15:50

I went on a world tour to 20 different cities and went and talked to hosts.

15:50

And I think I came back from that with a little bit of credibility with Brian to say like, hey, you know, yes, our data science team and the quality folks were who are doing qualitative interviews, they're getting something out of this, but I actually went into the homes of these hosts in all around the world.

16:12

And and I think I I was lucky because Brian did less of that than he did with other people.

16:18

But he for the for the product team, my god, I mean, a product meeting with Brian would keep people up the night before.

16:23

uh not just because they were actually working all night long to get prepared, but also that they knew they would work all night long because they probably wouldn't sleep in anticipation for this.

16:32

So that's that was another issue for I'd say um I think the other thing that you know that and and in each of these cases I think Brian's getting better.

16:39

So just like Steve Jobs got better over time when he left and then he came back, he was much better when he came back from all the people I've talked with who worked with him.

16:49

I'd say the third thing for Brian was the sense that adding a zero to something in terms of expectations or thinking that you're going to set a deadline that is unreasonable is necessary because if you don't do that there's an almost an underlying message that people won't kick ass on their own.

17:14

So there was a sense that Brian had that he had to maybe create ridiculous goals because even if we hit half of that goal, it was very encouraging.

17:31

What he missed in that was the fact that when you miss a goal and when you have someone who has power over you setting the goal or encouraging a particular goal, you're setting people up for, you know, a lot of stress.

17:45

And so at the end of the day, I think Brian is an, you know, a generational leader for as a millennial.

17:54

Um, and I think he deserves a lot of credit and Airbnb is as successful as it is partly because of Brian's leadership and I would not have been there without him.

18:07

Having said that, I had to hold my tongue in meetings sometimes uh when I saw how he was operating because I wouldn't have done it that way.

18:15

And I think over time, I hope I had a little bit of influence on him in terms of how to apply some emotional intelligence uh to leading people.

18:26

For people in this position, a lot of people work for founders, especially now that founder mode is a thing.

18:33

Every founder is just like, I'm the founder.

18:33

You got to do what I tell you. It's founder mode.

18:37

We're getting this is how we win. We're in founder mode.

18:37

You shared really good insight of building credibility as a really good lever to work better with someone like that.

18:46

Is there anything else you just think as uh tactics to be effective with founders in founder mode?

18:52

So, if I knowing what I know now, I would say Lenny, let's let's do a little pep talk you and me before the meeting.

18:57

I want you to start the meeting with the following uh as as you present and Brian's in the room.

19:03

So, Brian, let's talk about what we're trying to accomplish here.

19:08

Let's get really clear, and you probably did this, but let's get really clear on what um both what's the intention of this iteration we're doing on the product, like what defines success and what do I want to get accomplished in this meeting?

19:22

And you start with that because that actually helps to make sure there's alignment.

19:28

And frankly, if there's not alignment, you might as well not have the meeting.

19:34

Let's spend the rest of this meeting talking about alignment.

19:34

That's what I would do because that's something you can come back to over and over again during the rest of the meeting.

19:44

When Brian or the founder, whomever it is, is beating you up on something, saying like, "Well, let me tell you why it looks like that or why we're doing that."

19:49

It goes back to that, you know, the three principles or the three key goals we're we're trying to do with this product update.

19:59

And um yeah, so so try to set alignment on the front end.

19:59

That's a that's an important tip for anyone working with anyone even.

20:07

So I love I love just that that works especially well here.

20:12

And then just going back to the credibility piece, I what you shared there is you went on this world tour.

20:16

Not something everyone can do, but just like getting really close to your customers and using that as a hey, I actually know what I'm talking about.

20:22

You actually should listen to me even though you're the founder. Yeah.

20:25

And don't and I think the other thing is um PowerPoint or whatever whatever tool you're using.

20:32

I mean like just be careful about being overly reliant upon it.

20:32

It just it's especially when you have a combustible founder who may take you off path such that your deck in its current order makes no sense at all.

20:48

So that I always wanted to really limit the deck as much as possible because I didn't know where the meeting was going to go and I wanted the deck's helpful at the start at the very start to just sort of set principles, set goals.

21:07

Um but yeah, so this whole story of you joining Airbnb in your 50s is a really good example of of uh c intergenerational collaboration, something that you're big on just the value of having folks that are older working at tech companies.

21:20

Maybe just talk about that broadly and then we segue into other elements of your career.

21:26

I wrote a book called Wisdom at Work: The Making of a Modern Elder after my Airbnb experience and um I did a lot of research.

21:30

I was like, "Wow, so why do we have less intergenerational collaboration in the workplace, especially in Silicon Valley, than we could we could use?"

21:42

And I started interviewing people.

21:42

Then I started talking to brain scientists, neuroscientists, and realized that a younger brain has fluid intelligence, tends to be fast and focused, really good at problem solving, uh, very good at linearity in terms of looking at things.

21:57

As you get older, the brain shrinks a little bit and you have crystallized intelligence.

22:03

And in crystallized intelligence, what's going on is your brain, you're going from left brain to right brain more adeptly.

22:08

You're there's a little bit less focus, a little more holistic thinking, systemic thinking, connecting the dots.

22:12

So you can imagine that on a team in a you know when you have older brains connecting the dots thinking broadly peripherally younger team members being really fast and focused and being able to think linearly how to get things done.

22:32

That combination can either be successful or not.

22:32

When it's successful it's brilliant.

22:32

And I think Laura, you know, Laura Modi, um, Laura Hughes Modi, who was my director of hospitality, but also we worked in so many different capacities with her in the company.

22:45

I loved working with her because her brain worked different than my brain.

22:50

And um that's the opportunity is when you realize that diversity on a team whether you know there's lots of kinds of diversity but when it comes to uh brain diversity not just with neurodeiverse people but age diverse people you get a benefit an effective benefit that is not as uh noticeable quite frankly in some other diversities.

23:08

Uh so I found that over and over was really helpful.

23:16

Part of my job sometimes was to find the blind spot.

23:22

You know, again, if you are very focused, you know, one of the things I said to Brian early on um was, you know, I I've seen the business plan now.

23:28

I know the goals of how big we want to be in three years.

23:34

This was very early in my tenure.

23:34

I said, but what we really have done, everything we're trying to do is to like have no regulations and pay no occupancy tax.

23:39

Now, hotels pay a bed tax, occupancy tax.

23:46

we're not paying it and we're trying to do everything we can not to pay it knowing that you know so for our listeners and viewers to know this this is something that a guest pays.

23:55

It's not the host who pays it the guest pays it. It's part of the bill.

23:55

If you go and stay in a hotel there's a big big tax part of the bill.

24:00

But it made us more affordable by not having to pay tax have our guests pay taxes.

24:06

Long story short is I said to Brian if we're as big as we're going to be three years from now I promise you we're going to be regulated.

24:12

I promise you, we're gonna pay be paying occupancy taxes.

24:15

So, let's take some proactive steps toward building a strategy for how we're going to be regulated.

24:24

And that's that has consistently been Airbnb's biggest challenge is regulation in municipal markets all around the world.

24:30

If we'd started a little earlier, maybe in New York, maybe in New York, it wouldn't have gotten to the point where it has been toxic in New York the whole for the last dozen years um ever since I was there.

24:40

And there's a few other markets in the in the world where it was like that.

24:47

So, I would just say, you know, um the value in in having some age diversity, even when you have an older person reporting to a younger person, is it can be collaborative.

24:59

There was a guy named John Q.

24:59

Smith, uh, you know, an engineer who you I think you probably remember him, uh, uh, at at Airbnb.

25:04

So, this is a guy who looked younger than he was and was he was a little bit nervous about PE like telling people his age.

25:15

But the thing that was great about John is over time he was not necessarily going to be the best coder uh, at Airbnb.

25:20

There was a whole new collection of coders coming in every, you know, month.

25:27

But he became a great manager.

25:27

And the beautiful thing about moving from the, you know, individual contributor to the the manager, the person who can actually bring out the best in a bunch of younger people who may be better technically than he or she is, but they know how to elevate talent.

25:47

I call this invisible productivity.

25:47

It's it's productivity in which you make everybody else around you better.

25:53

And that's something I tried to do with my teams at Airbnb.

25:59

And ultimately I had six different teams, five hospitality and five other teams reporting to me.

26:03

And I did my best to just be the kind of person who wasn't solving all the problems, but I was trying to elevate.

26:09

There was a woman named Lisa Deost who is at at Airbnb and she one day I the HRE department was reporting to me at one point and she was running HR.

26:15

She was 25 and had no background in HR at all.

26:21

And one day she came into me and she just said, "Chip, you are my confidant."

26:25

confidant." and Lisa Lisa has a French accent and you know fluent in French and she said so she said confidant in just the right way and and I said oh well thank you Lisa but I said to her you haven't given me any juicy details yet like a confidant is someone who has the secrets and and she said

26:42

to me no in my in my part of France a confidant is somebody who gives you confidence and it was like oh well maybe that's what a mentor can be is a confidant someone who gives gives you confidence and helps by asking questions helps you as the younger mentee find your road map to success. So you're sharing a lot of really good examples of the value of older folks being within tech

27:04

So you're sharing a lot of really good examples of the value of older folks being within tech companies.

27:09

So let me just ask you this.

27:09

How how real is agism in tech?

27:09

And I ask because a lot of people that are hiring are probably thinking, "No, no, I'm not biased.

27:16

I'm going to hire the best person.

27:19

If there's someone in their 50s, I'll hire them. No problem."

27:19

Doesn't feel like it actually works out that way often.

27:23

just how real of a problem is this? What do you see?

27:23

Yeah, it, you know, it's clearly a problem.

27:28

Um, I'd say it's maybe a little bit less of a problem than it was a dozen years ago because I think a dozen years ago it was almost a blind spot.

27:35

You know, in Airbnb, we had a group called Wisdom at Airbnb.

27:41

It was an employee resource group for people 40 and older.

27:47

And so there are lots of these kinds of groups that didn't exist a dozen years ago in all kinds of tech companies, which is good because it means that there's a there's a voice and a way to congregate with a bunch of people who are older.

27:56

Ultimately, we had these senior we had these senior nomads come in and be like the voice of the customer for 10 weeks at Airbnb.

28:01

And it was the wisdom at Airbnb older employee group that really actually pushed for this with Brian.

28:14

But the the challenge is in a world in which the smartest new people especially when it comes to technical skills and engineering are coming in with a whole new you know uh set of skills that an older person doesn't have.

28:29

The the older person is both expensive uh and may be perceived as slow.

28:36

So in the era of AI, it's a whole new ballgame and the question I think will be if what AI cannot do is the human wisdom piece, artificial intelligence and and human wisdom might be the balance beams here.

28:54

Is it possible that older managers who have a little more emotional intelligence, a little more more pattern recognition, a little bit more wisdom um can be a value to a company?

29:00

And so it's still the the jury still out.

29:09

There's a New York Times article that just came out about the question of is AI going to wipe out older people's jobs or younger people's jobs?

29:14

And I think the answer is both.

29:20

answer is both. But the the question is how much how bad is it for both of them and um I think that what I would say to an older person and when I say older I mean what 45 or older if you've done well

29:35

financially and you're doing okay the question you might ask yourself is are you open as I ultimately was with Brian in my fourth year at Airbnb I took a substantial pay cut like I think I went to down to 40% or 50% time and my stock uh my you options were dropped to that level. My salaries dropped to

29:47

My salaries dropped to that level because I didn't want to work full-time anymore.

29:55

And there are a lot of people who can be valuable in a company who have some institutional wisdom, some process knowledge of how to get things done in this organization.

30:05

And in tech companies, that's really important.

30:05

Um, Airbnb, one of the biggest challenges at Airbnb has always been how do I get [ __ ] done around here?

30:16

Um, and process knowledge allows you to understand how do you how do you deal with an org chart and get things done partly because you understand the motivations of different groups and that is something you build over time.

30:27

So, long story short is um I just think that uh you know older people might look at their workload and say I'm willing to take a 20% or a 40% pay cut to go to 80% or 60% time and the company is going to get their money's worth in that.

30:42

That's a really interesting point that if you're older and you're maybe less connected to the most cutting edge ways of building and and coding, AI makes that a lot easier in many ways where you start to just talk to it.

31:00

You don't even need to understand what's happening underneath. Yeah.

31:00

So, there's a lot of listeners who are older in tech.

31:05

There's a lot of listeners who are approaching midlife, let's say, worried about what happens to their career.

31:11

When you look at people you've worked with and had at your academy, which we'll talk about, who continue to thrive and continue to have a really healthy career in tech, what do they do differently? What do they do?

31:21

What what do they have in common that other folks you think should work on and focus on?

31:26

I think this this idea of being a mentor, a mentor and an intern, this just the voracious appetite for curiosity.

31:30

When I talk to someone who's in midlife and wants to be in the tech world or already is, the thing I say is show up with curiosity and a passionate engagement for what you do.

31:42

And people won't necessarily notice your wrinkles as much as they'll notice your energy.

31:48

And energy has two parts to it.

31:48

Uh energy is they notice that you are not just sort of resting on your laurels.

31:54

You are you have like physical you know energy in how you do your job.

32:00

And when people are like that, they are sort of timeless.

32:06

They are a they're age fluid, as I say.

32:06

Um, we talk about gender fluidity.

32:06

Well, there could be age fluidity.

32:12

They they don't they're defined by their age.

32:12

But the other part of energies that's important is being positive.

32:17

You know, that's sort of more energetic, like a little bit more California energetic.

32:22

There's a sense of like when someone's got good energy, you're drawn to them.

32:28

So, it's about showing up with the kind of energy of someone 10 or 20 years younger than you and then showing up with positive energy.

32:35

And I think one of the things that I would say I did well at I mean there's lots of things I didn't do well at Airbnb, but in terms of what I did well is I was very approachable.

32:46

And over the course of time, the number of mentees I had, the number of people who just wanted to have coffee with me or tea, the number of people who just said, "Thank you for being in that meeting, you just sort of gave it a positive feeling was really important."

32:57

and and um so my energy both the positive energy part and then also the fact that yeah I I could work 60 and 70 hours a week and I could travel around the world as the as the secretary of state of the company which is what Brian called me a couple times on the stage.

33:16

The fact that I could do that meant that no one was looking at me and saying let's get rid of the old fogy.

33:21

Uh well maybe some people were but I wasn't aware of them.

33:28

So, I just think show up with that passionate engagement, that curiosity, that energy, the ability to be both the learner and the teacher with respect for people that younger than you, and you're going to probably do pretty well.

33:40

That is really great advice.

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35:03

Interestingly, curiosity comes up a lot when I ask AI forward people what are they focusing on helping their kids learn most.

35:08

Curiosity is the most common way to describe.

35:08

So, at every stage of life, curiosity is uh some to cultivate.

35:14

I want to go to the flip side of companies looking to hire.

35:20

Feels like there's this uh untapped supply of awesome people that companies with agism and tech uh aren't finding and hiring.

35:27

So to help hiring managers and companies take advantage of this, what's something you suggest they do?

35:33

How do they shift their mindset or maybe shift the way they they hire that might help them find these people?

35:37

I think we're moving into there's a there's a book that David Epste wrote called range and the whole premise of range is that we are moving out of the era of the specialists and into the era of the generalists and I think AI is just accelerating this um as we are more reliant upon AI and AI can can be exceptional at technical skills and solutions really expeditiously.

36:03

I think generalists, people who can think broadly become all the more important.

36:11

And I think that what I would say to someone in HR or recruiting, uh, is yet beyond what I already said before is is the person passionate? Are they curious? Are they a learner?

36:24

Um, do they have good energy?

36:24

But I would also say, are they a generalist when they're a problem solver?

36:31

because I actually think that's going to be an increasingly important part of how effective companies think broadly.

36:38

So I think that's a key one.

36:38

I think also this idea of how do you create intergenerational collaboration in the form of mutual mentorships.

36:48

Um, one of the things I I I loved at Airbnb with there were a few people I did this with where I had something to teach them and they had something to teach me.

37:00

So, um, good example, my iPhone.

37:00

So, there's 97% of the utility of my iPhone that I probably don't use and don't know how to use.

37:09

This is, you know, back in, let's say, 2013, 2014.

37:14

And so there were people in who knew iPhone or Google suites back then.

37:23

I'd never used a Google doc back then when I joined Airbnb.

37:23

So there were people who could teach me something technical and then they wanted to learn something from me which would be like how do you run a great meeting um or how do you give a great employee review?

37:34

you know, there are a lot of managers who've never been a manager before and and so how do you disperse people like me in the organization so that you don't you know there's usually not enough time for these young managers to come to some training session on how to do a good you know employee review.

37:57

So you sort of have to do it out there in the field.

37:57

It's like apprenticeship.

37:57

You know, back in the trades, you are you're an electrician apprentice.

38:02

Not because you're watching, you know, some video on it.

38:09

You're out there in the field doing it.

38:09

And and that's a huge value in a younger company when you have some older people who have not been vested with the responsibility of managing those younger people because they may have they may actually be reporting to someone younger than them, but they're there to actually be support.

38:25

And um in some ways I think that was part of the unexpected value that I was able to offer to Airbnb and to Brian specifically because there are a ton of people in Airbnb who were not even in my departments who would come to me and say I'm having a problem. How do I solve this?

38:44

Can we spend lunch together?

38:44

And you know I almost always said yes.

38:52

I think the reason people did that in many ways is you just have a very unique aura of wisdom and it's hard to replicate that chip. Yeah. I mean Yes.

38:56

And it all comes back to the curiosity.

39:06

If I was just the older elder dispensing wisdom, people would have gotten bored very quickly.

39:14

And I think the fact Yeah. Yeah.

39:14

I mean, I was on the board of Burning Man. Oh, that's cool.

39:19

And so there was a I I I I show up as someone who feels younger than I am.

39:19

I mean, I'm turning 65 this year.

39:27

So the bottom line is I think people lost track of my age partly because I lost track of my age.

39:36

That's such a good such good advice.

39:36

So on the front end uh to be successful as a person kind of getting older in tech is curiosity, positive energy.

39:42

the way you tal talked about it passionate passionate uh engagement is that the term? Yep.

39:47

And then on the other side is uh hired generalist.

39:54

This actually comes up a lot in in the AI conversation just exactly as you said the power of generalist reminds me I'm I'm going to this gym now and the lady there is just like I love AI so much because I'm just such a big picture person and I can so bad at just getting thinking about the details and AI solves all that for me.

40:10

It's like here here's what I want to do.

40:14

I'll do this, move my house to here, here.

40:14

And it's like, here's what you need to do.

40:14

Step one, two, three, four, five. It is remarkable.

40:17

I mean, you know, since the time I've known you, how fast it has become dominant in our lives.

40:23

Uh, but yeah, I think one of the last thing I'd say is look, I'm privileged.

40:30

So, for those of you who are listening or watching this and you're saying, well, you know, Chip, you were 52 years old and they came to you.

40:36

Like, that doesn't happen to me.

40:41

I'm not in that position.

40:41

The thing I would say is you're right.

40:41

So I but I could have been plucked and brought in and partly as as Brian's boy, people would have like rejected me because if I didn't show up the right way, it wouldn't have worked well.

40:56

Uh and there are lots of people who Brian brought into the company who didn't work well.

41:01

So I think I think the key is how do you get the foot in the door?

41:09

And at the end of the day um you know those second and third order of you know uh degrees of separation um in terms of networking is are still essential.

41:16

But the most important thing is to be able to articulate what you have accomplished in a new way that a recruiter says wow.

41:33

And so I I really tell people like I I would love to see a resume.

41:33

First of all, the question that uh I think it it was who was someone asked it.

41:41

I don't remember if it's Cheryl Stanber or someone else asked her who said like what's the biggest problem you're dealing with here and how can I help you?

41:50

Like that's a great that's a great line.

41:50

Number two is uh what I love to see is not so much what roles you've had, what bullet points do you have of your like things you've learned.

42:03

Give me in a paragraph a a a thorny problem you faced.

42:03

Um what what was the problem and how you got how you what skills you used to actually accomplish it and what was the result of that.

42:20

I would love to see a resume like that.

42:20

And the older you are, the more you can actually have a resume like that.

42:26

And then you can use that as the conversation piece when you're doing interview your interviews. So, I love that.

42:32

I love that we're getting into interview advice and resume advice. Yes.

42:36

Um, speaking of throwing problems and also uh why Brian decided to reach out to you, I want to go back to the beginning of your career. Yes.

42:42

So, you're good at this, by the way. You're good at this. was thinking ahead.

42:48

Okay, so you're in business school.

42:48

You left business school.

42:54

You decid you're like maybe I should start a hotel.

42:54

Uh something that rarely works out usually probably leads to a lot of money lost and a lot of frustration and just like okay what have I done with my life worked out for you?

43:03

Ended up building the second largest boutique hotel chain in the world.

43:08

Uh beloved uh I I I loved every single experience I've had at when you sold it.

43:15

I was like that is so sad.

43:15

Talk about just that that story.

43:15

Uh, I know this could go on for hours, but what's the Yeah, I'll be I'll be brief. Yeah.

43:20

26 years old, couple years out of Stanford Business School, working for commercial real estate developer. I was bored silly.

43:25

I wanted to do something more creative.

43:29

Bill Graham, famous concert promoter, said to me, you know, because I gotten to know him, what San Francisco really needs is a rock and roll hotel.

43:34

So, I decided to start looking to to find a broken down motel hotel that I could turn into a rock and roll hotel.

43:46

and I found something in the Tenderloin uh and uh and turned it into the Phoenix which became a famous rock and roll hotel that I have owned for 39 years now.

43:52

Um so long story short is that was how I started in the company and we grew to 52 hotels around California became the second largest as you said in the in the world uh in terms of the number of hotels boutique hotels that we operated and I loved it till I hated it in my late 40s. I hated it.

44:13

Didn't want to do it anymore.

44:13

I was, you know, the Great Recession came along and it was just kicking my ass.

44:18

And I really went through a bit of a what I now call a midlife cryis, uh, but a midlife crisis, um, where I just wanted to change everything.

44:31

And, um, I got through it.

44:31

Uh, I had an NDE, had a near-death experience where I had an allergic reaction to an antibiotic and I died.

44:37

And from that point forward, I realized every day is a a gift and a bonus.

44:41

and um uh you know I decided to sell my company at the bottom of the great recession.

44:48

So that's so that was really how I created this space in my life to be able to join Airbnb.

44:54

Well, let's back up a little bit.

44:54

This near-death experience uh share more there what happened there.

45:01

Yeah, I was uh so I write books.

45:01

have written seven or eight books and I had written a book called Peak uh how great companies get their mojo from Maslo and it was a book that Brian really liked and part of the reason he he wanted to reach out to me. Um I was on a book tour. I had a broken ankle.

45:16

Uh broke my ankle at a bachelor party uh playing baseball and um I ended up with a cut on my leg and um the cut on my leg had fertilizer in it and went septic and so I was on a very strong antibiotic and I died.

45:33

I went flatline from the allergic reaction to the antibiotic and so I saw you know I it happened nine times over 90 minutes.

45:47

I kept dying, kept flatlining and yeah, ended up in the hospital for a couple three days and they finally said, "Listen, it's an allergic reaction.

45:53

We believe they thought it was I thought they thought it was a heart attack.

45:58

Thought a bunch of stuff, stroke, etc."

45:58

No, it was the allergic reaction.

46:03

So, but you know, I saw birds.

46:03

I mean, I saw all this beautiful stuff.

46:03

I We don't have time to go into it. What? I did. You want to hear this? Yeah.

46:09

No, I saw this beautiful stuff.

46:14

the the best I think there's a hotel in San Francisco called the Vitali that I built um across the street from the ferry building and it's still there but it's no longer called the Vitali.

46:23

Um in that hotel there were these slippers in every guest room.

46:23

One slipper said slow, the other slipper said down.

46:29

Um, and so I was wearing these slippers in my flatline thing, uh, flying in in the air in a 40 foot tall living room in the Alps, surrounded by birds that were twer tweeting and and chirping at me.

46:48

And I understood bird talk.

46:48

I understand I understood exactly what they were saying.

46:55

And they kept telling me, "If you slow down, you will see beauty and you will see awe."

47:02

And there was a bunch of other things, but let me just limit it to that and just say, and then the birds would like say, "It's time to go."

47:07

And the birds would go out the big window, you know, into the mountains, and I would try to follow them.

47:12

And right as I would get to the window, all of a sudden, I'd come back to life.

47:17

Holy [ __ ] Uh, I love that this was uh like there was a message inside of this experience.

47:24

I don't know how many people experienced that.

47:29

Clearly, this led to a big life change.

47:29

And it's interesting that a lot of times you need something like that.

47:34

Like you've been doing this for how many years at that point running?

47:34

Uh, at that point I've been running for 22 years and 22 years.

47:38

And it's interesting that you need something like that a lot of times otherwise it just momentum just keeps carrying you forward. Yep.

47:42

within two years I'd sold it and you know I had had the chance to move on.

47:47

So with building Juvary something you've written about a number of times is just the way you built it as a really unique approach to building a business.

47:58

Specifically there's a huge focus on culture which also came out at Airbnb.

48:03

Talk about just why you see culture as such an important part of how you build a business like tangibly because a lot of people talk about culture warm fuzzy stuff but you think about it very tangibly.

48:14

Culture is what happens around here when the boss is not around.

48:14

Um and and the more distributed a company, the more culture is important because the boss is around in a traditional bricks and mortar workplace where everybody shows up at 8 and leaves at 6 and we all see each other.

48:36

But uh at in my company in Aviv, we had 52 hotels and 25 restaurants and four spas and it was distributed.

48:46

So I couldn't be in all those places all the time.

48:46

And same similarly with Airbnb.

48:52

I mean Airbnb had offices around the world and was it was a global company.

48:58

So the more distributed you are, of course, in the remote work world we live in, the more culture is important and more difficult because the when you're remote, you know, there's these few cues you have about how we do things around here and they're usually in a digital virtual format, which is why, you know, it's all the more important for you to have in-person gatherings of a team more often if you are virtual.

49:23

So at the end of the day, the reason culture is important is because it actually helps it helps guide people in terms of making decisions, but it's also a magnet for the right kind of people.

49:35

So Oracle has a different, you know, culture than Apple, which has a different culture than Facebook.

49:42

And so you can choose the place you're going to work based upon the culture.

49:47

And there are people who can be very good at what they do, but if they're in the wrong culture, they're in the wrong kind of environment and they're not willing to shift to fit that culture.

49:59

And we saw it at Airbnb all over and over again.

49:59

Uh in in fact, Airbnb saw it, I think, when with Amazon people.

50:05

Um Apple people have resonated pretty well at at at Airbnb. Amazon people less so.

50:12

And those are two different cultures, Amazon and and Apple.

50:12

And that therefore understanding a culture before you even actually take the job is one of the more important decisions you need to make is like is this culture a culture that I can live with? Um and maybe influence.

50:32

Um there's language about culture fit.

50:32

I like to say culture ad because culture fit to me means can actually be quite negative toward somebody who is the aberration.

50:39

Um you have to fit in and especially if this is like a demographic thing, a person of color, a gay person, a you know a person in a wheelchair. So you have to fit in.

50:55

But a culture ad suggests that actually having some diversity on the team is helpful because it actually adds to the culture.

51:02

But that's still h you still have to be able to get along in that culture.

51:07

So culture is an intangible.

51:07

That's the problem with it is it's hard to measure but you see its value and you understand whether it's working based upon p you know employee pulse reports and things like that.

51:20

You talk about having to understand a culture is such a key part of having success at a company.

51:25

Do you have any advice for just how to understand that culture for someone interviewing?

51:30

advice for just how to understand that culture for someone interviewing? I don't know like you know you came in you work part-time it's easier to experience it all any tips there for like okay this is for me this not for me when you're interviewing you're you're also interviewing them

51:43

when you're interviewing it's not about you having to prove yourself it's also for them to actually prove themselves as a company and also try to understand if there is um some alignment in the company and so the kind of questions I would ask as someone who's being interviewed would be what are three to five adjectives that define this culture. What's the biggest problem in this

52:00

What's the biggest problem in this culture in terms of something that's just endemic or like baked in across the organization and is it ever going to get fixed and how could I come in and maybe help that?

52:14

Uh which frankly at a very junior level you're not going to be able to help it.

52:22

Uh except for in very minor ways.

52:22

If you're a senior person you might be able to help it.

52:27

Um, so those are those are the kind of questions I'd want to know.

52:32

And frankly, if I'm asking that same question about what are the adjectives to multiple people, am I hearing the same thing over and over again?

52:38

Um, and if I'm not, is that because there's not alignment, is that because different departments have different flavors?

52:43

Um, because you can have a culture within a department that's very different than the overall corporate culture.

52:53

The corporate culture certainly has an enormous oppressive uh influence, but uh you know you can you can you can be in a culture uh a really great culture of a team or a department in an overall company culture that's not good.

53:10

In the long run, that oppressive company culture is either going to have to evolve or your department may be you may lose people.

53:17

When I reflect back on one of the on the impact you had at Airbnb, one of the funny uh things I think about is uh triangles showing up a lot on decks uh and specifically rooted in Maslo's hierarchy.

53:31

Just like everything's this Maslo hierarchy metaphor. True.

53:38

Um, and this one uh I don't know specific piece of this is you have this kind of model you think about for how to help employees be successful at a company.

53:46

It's kind of rooted in your peak book uh philosophy.

53:52

Maybe just talk about that and then if there's anything else you want to expand on with this power of thinking through the Masow hierarchy.

53:56

So you know Maslo's hierarchy basically five levels.

54:01

Later in life he had a seven and an eight level model.

54:01

But you know uh at the base is you know physical uh you know the kind of physical water, food, air and you move up to self-actualization at the top.

54:15

Um so to use this model as a hierarchy of needs for employees, customers and investors is what the peak model is about.

54:24

uh the the you know the peak uh my book um the employee model is really simple.

54:30

It's money or compensation at the base um recognition in the middle and meaning at the top.

54:38

Now there are some industries and some kinds of jobs in which money is 90% of the pyramid.

54:43

So just because it's at the base doesn't mean it's not the dominant part of the pyramid.

54:48

But the differentiation often is in recognition and meaning in nonprofits.

54:48

It's usually the money piece of it's rather thin and the recognition's this and meaning is huge.

54:55

So I so understanding how do you create an organization and and I gave a TED talk in 2010 about this topic as well.

55:07

Um how do you create a how do you measure the intangibles uh of meaning and how do you create an environment where people feel a sense of meaning?

55:14

Um the customer pyramid briefly, I'll just say that one is meeting expectations is the base, meeting desires is in the middle and then meeting unrecognized needs.

55:25

And I think one of the things that we did at Airbnb about a year after I joined and when Jonathan Mildenhal was joining is we really tried to ask ourselves, are we in the home sharing business or are we in some kind of business that is even bigger and broader than that?

55:43

And ultimately we we came up with the idea that we were in the belong anywhere business.

55:48

Airbnb was not in home sharing.

55:48

We were in belonging anywhere.

55:48

So once you have that uh down that was sort of the unrecognized need at the top of the pyramid.

55:55

Then that becomes an organizing principle for how do you teach your hosts to create a sense of belonging?

56:01

organizing principle for how do you teach your hosts to create a sense of belonging? um how do our how does our marketing and advertising play up the belonging piece especially and the everywhere

56:12

piece because hotels are not everywhere but homes are and so I would just say that you know this model the idea of hierarchies is I think very helpful um and uh yeah my book peak is has been out for 18 years but I still am asked to give 20 or 30 speeches a year on it oh man this

56:32

uh this pyramid of comp recognition meaning is really interesting Especially these days because uh like with all this AI uh researcher poaching, there's all this talk of just like it will people

56:42

just go work wherever the you know they get they get the most money or is there a mission and and meaning to the work they're doing that will keep them not taking a hundred million dollar offer and seems to be happening a lot of cases which shows you the power of meaning. Yeah. I mean, Yeah.

56:51

I mean, if you know you're working for a toxic company, at some point your conscience kicks in.

56:57

Whether it's toxic in terms of the purpose of the company, toxic in terms of the leadership or the culture. Um, yeah. Life is too short. Okay.

57:07

So, you've had two major shifts in your career.

57:07

You started the hotel chain, you went to then you went to Airbnb.

57:14

Most recently, the Airbnb experience, I imagine, led you to starting something in the called the Modern Elder Academy.

57:20

talk about what is the modern elder academy. Yeah.

57:25

What is going on with that modern elder academy?

57:25

The modern elder academy.

57:31

So there was a couple times where I was called the modern elder at Airbnb.

57:31

And then I was told that a modern elder is someone who's as curious as they are wise.

57:37

So uh Jonathan Mildenhal who was the chief marketing officer at at Airbnb used to call me the modern elder as well.

57:43

And when he and he said like if you ever create a school you you know modern modern elder would be a good name.

57:55

And so we talked about it and next thing I knew I was like saying okay this is called the modern elder academy.

58:00

We now call it MEA because elder is a fraught word on some level.

58:00

It makes you sound elderly.

58:04

But um what I really wanted to create was a place where people could come and do a workshop.

58:12

you you know they're fiveday workshops um in Baja on the beach or in Santa Fe on a big four square mile uh horse ranch and reimagine and repurpose yourself and navigate transitions.

58:20

We go through so many transitions in the middle of our life.

58:27

Let's say between I I define midlife as 35 to 75 guys.

58:33

So like this is it's a very it's a very long life stage.

58:33

So we go through a lot of transitions.

58:40

We are constantly evolving our purpose.

58:40

We're building our wisdom.

58:40

You know, we have knowledge management tools out there, but where are the wisdom management tools?

58:46

Where are the tools that help us to get wiser over time?

58:49

And then we need to reframe our relationship with getting older because Becca Levy has shown at Yale that when you shift your mindset on aging from a negative to a positive, you get seven and a half years of additional life, which is more life than any other biohack that's being done right now. So that's what we do.

59:05

and we have 7,000 grads from 60 countries and 56 regional chapters around the world.

59:11

So, it's a bit of a movement.

59:11

And um I teach I I teach some of the workshops and we have all kinds of famous people who come and teach.

59:18

And for me, creating the world's first midlife wisdom school just feels like the the natural next thing for me to do.

59:30

I I love hospitality so it's a very upscale kind of experience, but we have scholarships.

59:36

I love um retreat centers.

59:36

I was on the board of the Eselin Institute in Big Surf for 10 years. I love wellness.

59:42

I've owned the Kabuki Springs and Spa for 28 years um which is the largest spa in San Francisco.

59:50

And I love education and my book wisdom at work the making of a modern elder gave me a curriculum in which we've expanded quite a bit with uh Harvard, Yale, Stanford and UC Berkeley professors helping us a great greater curriculum around midlife.

1:00:05

Um and so that's how MEA came about.

1:00:12

Uh to your point I forget who said I think you said Jonathan has said this was the natural next step for you. I completely agree.

1:00:17

It's like looking back this is the obvious thing you should be doing right now. Yeah.

1:00:21

Uh, also I'm learning more things about you.

1:00:21

I didn't know you were involved with the Kabuki Spa.

1:00:25

I think Esel and I knew just keep getting more interested. Thank you.

1:00:31

There's a couple threads here I want to actually follow.

1:00:31

So this point you made about shifting your mindset to aging is a positive thing.

1:00:35

Makes you helps you live longer.

1:00:35

That's such a powerful point.

1:00:40

Can you just speak more to that?

1:00:40

Just what does that look like?

1:00:40

Yeah, there's a couple there's lots of data points.

1:00:44

I'm just I'll talk about two.

1:00:44

One is this Becca Levy study which has been going on for 15 to 20 years.

1:00:48

If you sort of take buy into the agism of American society or Hallmark cards when you get a a a card at age 40, 50 or beyond, there's a belief that life gets worse as you get older.

1:01:04

And um and if you can survive your midlife crisis, all you have to look forward to is disease, decrepitude, and death.

1:01:11

And the bottom line is uh you know, there's a lot of things that get better with age.

1:01:16

I wrote a book called Learning to Love Midlife.

1:01:20

The subtitle says it all.

1:01:20

12 reasons why life gets better with age.

1:01:20

And what I really wanted to do with that book, which is really it it summarizes the MEA curriculum.

1:01:25

I wanted to write a book that sort of helped people to see the upside of aging, the unexpected pleasures of aging.

1:01:31

Uh so they had a pro-aging, not just an anti-aging point of view.

1:01:36

Because when you actually have a pro-agging point of view, and you see the upside of aging, you take better care of yourself, both your mind and your body, you actually are willing to learn and try new things.

1:01:47

One of my favorite MEA questions is 10 years from now, what will you regret if you don't learn it or do it now?

1:01:53

It's a powerful question, really important question as we get older.

1:01:58

When you're young, you know, you've got all, you know, all of your life left ahead of you.

1:02:03

But when I moved to Baja part-time in Mexico at age 56, um I had a mindset which was I'm too old to learn Spanish.

1:02:10

I'm too old to learn to surf.

1:02:10

But when I said 10 years from now, what will I regret if I don't learn it or do it now?

1:02:15

And I said, well, 10 years from now, I might still be living in Baja, like I should learn this. I should learn Spanish.

1:02:25

I should learn how to surf because we're right next to a surf break. And so I did.

1:02:25

Um, so what I believe is that anticipated regret is a form of wisdom.

1:02:31

And so and it's a catalyst for taking action.

1:02:38

So that's one data point.

1:02:38

The other data point is something called the U curve of happiness and it's been around for 20 years and it shows the following.

1:02:44

It has changed in the last couple years because young adults are h unhappy like never before.

1:02:49

So a 20 or a 22 year old really unhappy, 24y old really unhappy.

1:02:56

But historically the way it was is you were happy from 18 to 23 or 24 and then around 23 24 you start to see a long slow decline in life satisfaction that actually uh bottoms out between 45 and 50.

1:03:10

I'm sorry to tell you that Lenny since you're 44.

1:03:10

Um but your mileage may vary.

1:03:15

So you're saying I'm the least happy I'll ever be. Like that's only upside. That's great. Yeah.

1:03:20

Well, here's the part that's weird is that when before this re research was done, and it's global research across all demographics, what they found was uh starting around age 50 or 52, you get happier.

1:03:32

So that you're happier in your 50s than your 40s, 60s 50s, 70s happier than 60s, and women in their 80s happier than 70s. So, wow.

1:03:45

And it's partly because we are in around 45 to 50 doing this thing called the um the midlife unraveling.

1:03:51

What Bnee Brown calls the midlife unraveling.

1:03:51

You're unraveling your expectations, your uh what you define as success.

1:03:57

Uh your definition of you what a beautiful body looks like and you get some you're liberated into freedom in your 50s and beyond.

1:04:03

And uh I can say that yeah, I'm happier today at 64 than I was at 47 when I was going through my flatline experience and not wanting to run my company anymore.

1:04:17

You used this term earlier, the midlife cryales. Was that what it was? Or chrysalis. Crystis. Chrysalis. What is that?

1:04:22

Is that kind of along the same lines?

1:04:22

So if you think about the caterpillar to butterfly journey, midlife is the chrysalis.

1:04:27

It's that cocoon in which all of the change is happening.

1:04:32

at the time, you know, when you're going through it, it's like, oh [ __ ] my life my life is liquefying in front of myself, but you know, on the other side of it, there's a metamorphosis that happens.

1:04:43

side of it, there's a metamorphosis that happens. And so uh I I like to use the language and in fact I have a podcast called the midlife crystis um because I want to help you know change the dialogue around midlife so that the number one word attached to midlife is not crisis um but in

1:05:01

fact it's maybe cryis and the idea that um life is meant to be transformative uh during that era that is actually very empowering I am sort of going through that not necessarily in this intense way yet but that might be You said there's a bunch of upsides to being getting older. It might be

1:05:14

It might be helpful just to share a couple of those things for folks that are like, "Oh, wow. I didn't realize that."

1:05:22

Emotional intelligence grows with age.

1:05:22

Um, our wisdom can grow with age, although we know 70 year olds who are not as wise as 30-year-olds.

1:05:28

So, it's a matter of what you do with your life experience.

1:05:31

I define wisdom as metabolized experience mindfully shared for the common good.

1:05:38

Uh, what else gets better with age? You learn how to edit.

1:05:38

you can't you you have no more Fs left to give, no more effects left to give there.

1:05:43

That is absolutely true, especially for women as they age.

1:05:47

You are more spiritually curious.

1:05:47

Uh you're um I mean the list is long and and so there are a lot of things that actually another one that I don't love is you're not compartmentalized.

1:06:01

When you're younger, you're compartmentalized.

1:06:01

As you go grow older, you are growing whole.

1:06:06

And that means you're alchemizing curiosity and wisdom, introvert, extrovert, masculine, feminine, gravitas, depth and levity, lightness.

1:06:13

And the people who I really admire who are 85 years old, they're so present and they are so whole.

1:06:20

They are like they are just who they are.

1:06:20

There's a quote I found from you along these lines.

1:06:26

The societal narrative on aging is just don't do it. Yeah. there.

1:06:32

I mean, we sort of say like we want we don't want to age, but we do want to live.

1:06:32

And quite frankly, aging and living are the same thing as are aging and growing.

1:06:38

Coming back to MEA, just for folks that are like interested, curious about this, who's this for, would you say, who should seriously look into this program?

1:06:49

MEA is really the people who tend to come to MA are in a midst of a transition.

1:06:55

It could be uh selling their company, leaving a job, getting divorced, um having kids, um becoming an empty neester, taking care of parents till they're passing away, having a health diagnosis. That's scary.

1:07:09

So average age is 54 and it's people of all walks of life.

1:07:16

Uh so it's not just the tech industry, but a lot, you know, it's very popular in the tech industry.

1:07:21

Um it's people who are looking to maybe do a reframe of their purpose uh and maybe even a reinvention of their career and so yeah and and the two campuses are just gorgeous.

1:07:27

Uh they it's been called the Four Seasons meets Blue Zones meets the Elon Institute which I like.

1:07:36

Um, and uh, we don't we have online programs, too.

1:07:43

And so you don't have to come to either of our campuses in Mexico or on the beach or in uh, New Mexico.

1:07:48

Uh, you can actually do it online. Those three.

1:07:48

Yeah, that's the tagline.

1:07:55

That's your tagline right there.

1:07:55

Esselin meets Blue Zones meets what was the first one? The Four Seasons. The Four Seasons. Yeah. Nailed it.

1:08:00

Okay, I'm going to zoom out and take us to a recurring segment on this podcast.

1:08:07

I want to see if this goes anywhere. Uh AI corner.

1:08:13

And with AI Corner, ask guests just what's a way that you've found AI useful in your work or in your life.

1:08:19

Any kind of trick you've learned, any workflow, anything you found useful.

1:08:19

Yeah, you know, I I have a daily blog.

1:08:24

It's called Wisdom Well, and it's on the MBA website.

1:08:24

And um when I'm looking for inspiration, you know, AI does it for me.

1:08:30

And ultimately, it gives me a first draft.

1:08:38

And that's good enough for me then to say like, okay, because there's times when I'm like missing the inspiration.

1:08:43

I tend to write really well in the morning.

1:08:43

If it's any other time of the day, I do not like writing creatively.

1:08:48

Um so if I have a deadline for tomorrow and it's five o'clock in the afternoon, it's like, "Okay, chat GBT. I'm on my way to you."

1:08:54

And I I tend to use chat GBT the most because I don't know.

1:08:59

I mean I like Claude as well, but um yeah. Okay, awesome.

1:08:59

I was going to ask which tool you use uh and what's your workflow there?

1:09:04

Is it you use voice mode?

1:09:04

Do you just kind of type out here's what I'm thinking about?

1:09:08

Write me a little drop blog post.

1:09:08

The good news is that at this point, uh it knows me well enough and my and my blogs and I've actually, you know, it it it knows my my sort of weird sense of humor.

1:09:18

Uh so it's able to ape me pretty well.

1:09:18

So, I'll just say I need a 250word post on um like today, you know, today's post was a post that chat GBT helped me with it.

1:09:34

I said, I believe that there's a a a reframe that needs to happen with soul.

1:09:34

We tend to say like I have a soul or I don't have a soul, but what if this my soul has me?

1:09:40

um what if in fact my job is just to be this vehicle for my soul to go to the next lifetime and my so my job is to be this steward of the soul and I said write me something around that and so it's just a weird idea and of course my not all my blog posts are so new age and and uh like that I I I write a lot on leadership but that was one that you know within you know 30 seconds I had a 250word you blog post that I then adapted. And there you go. Amazing.

1:10:16

Chip, we've covered a lot of ground.

1:10:22

We've gone through your entire life.

1:10:22

Maybe actually just the tip of the iceberg.

1:10:22

With that, we've reached our very exciting lightning round.

1:10:27

I've got five questions for you. Are you ready? Yes. Let's do it. First question.

1:10:31

What are two or three books that you find yourself recommending most to other people?

1:10:36

My favorite book of all time, Man's Search for Meaning, Victor Frankle, uh in a concentration camp in World uh World War II.

1:10:41

when someone's going through a hard time in their life, I say, "Read that book.

1:10:46

You'll realize it's not so bad what you're going through." Yeah.

1:10:46

Um, but it also really speaks to this idea of despair equals suffering minus meaning.

1:10:50

I wrote a book uh called Emotional Equations that was a New York Times bestseller that spoke to this idea that what if you could take all of your emotions and turn them into equations.

1:11:01

Very engineering-minded of me. Um, so that's one.

1:11:06

Um I you know I love uh any book by Liz Gilbert. Um sort of the opposite.

1:11:06

So Elizabeth Gilbert wrote E Pray Love.

1:11:17

Her her book she's a she's on faculty at MEA. She teaches here.

1:11:23

Um uh Big Magic is just a beautiful book about sort of like how do you get in the flow to allow the genie to come through you.

1:11:31

um her TED talk in 2009 was about the fact that genius is not about being the genius yourself.

1:11:39

It's about being the receptacle for the genie to come through you.

1:11:39

I want to come back to this uh equation you shared.

1:11:44

I was going to get to it but I didn't.

1:11:44

So this is a good opportunity to So there's a couple that are really interesting to me.

1:11:48

This is you wrote about these in a book.

1:11:53

You have a bunch of these equations about living a happier life.

1:11:53

So the one you shared is despair equals suffering minus meaning. Yes.

1:11:57

And so the implication there is if you want less despair increase the meaning. That's right.

1:12:02

So suffering suffering the sort of Buddhist philosophy number the first noble truth of Buddhism is that suffering is ever present.

1:12:13

And so if suffering is a constant and you have two variables uh using some algebra I guess um you know that uh if you have more meaning you have less suffering. And so that's that one.

1:12:25

The other one that I love is anxiety equals uncertainty times powerlessness.

1:12:25

Maybe talk about that one briefly.

1:12:31

98% of anxiety comes from two sources.

1:12:31

One is what you don't know and number two is what you can't control or influence and based upon social science.

1:12:38

And so um you can create an anxiety balance sheet and you know create four columns.

1:12:44

First column is what is it you do know about this thing that's making you anxious?

1:12:50

The second column is what is it you don't know.

1:12:50

The third column is what is it you can control or influence.

1:12:54

And the fourth column is what is it you can't control or influence.

1:12:58

And when you take free floating anxiety and put it into uh a an equation, it actually makes it more tangible and you often are less anxious as a result. Boom. Okay.

1:13:06

So, if you're feeling anxious right now, this is an exercise you can do and you'll feel less anxious in like five minutes is what I'm Okay. Excellent.

1:13:16

Very, very good nugget of advice. Okay.

1:13:16

Let's keep going with the lightning round.

1:13:22

come back from our tangent.

1:13:22

Do you have a favorite recent movie or TV show you've really enjoyed?

1:13:27

I mean, Ted Lasso is I'm like a sucker for for for that show.

1:13:27

You know, when it comes to movies, I'm a total movie buff.

1:13:34

I I we have an annual MEA film festival uh at our Santa Fe campus.

1:13:42

Um and I would say that the film that I'm most excited about that is coming out um that most people have never heard of is called I'll Push You.

1:13:49

And it's the story of two guys, one of whom is uh in a degenerative health condition and in a wheelchair and his best friend pushes him the 500 miles of the Camino de Santiago and it's the relationship they build along that way. Amazing. Very deep cut.

1:14:07

Do you have a favorite product that you recently discovered that you really love? Yes. Hair growing material. No.

1:14:13

Um, you know, uh, Viori shorts I I, you know, I sound like Scott Galloway because he t he advertises this, but Viori shorts are like I just love them.

1:14:29

You know, they're just breathe and they're comfortable.

1:14:29

I'm wearing the Yori uh joggers right now.

1:14:33

Uh, the one downside of Yori, not to make anyone mad, is they're not like very they're kind of plasticky if you look at the material.

1:14:40

So, I'm trying to like I don't know. Yeah.

1:14:44

But I do love There's nothing better. That's the problem.

1:14:44

I have done anything else like this that isn't all cotton. Yeah. Yes. But I'm a fan. I have many Vori.

1:14:48

I don't know if they're called chuggers.

1:14:53

Just I don't know, weekenders or something. Anyway, love you, Vori. Okay.

1:14:53

Do you have a favorite life motto that you often come back to and find really useful in work or in life?

1:15:04

I imagine you have many, but is there one that comes to mind?

1:15:04

I mean, my favorite one right now is your painful life lessons are the raw material for your future wisdom.

1:15:08

And the the premise of that is that wisdom often comes through the school of hard knocks.

1:15:15

So when you're in the midst of a really, you know, challenging time, you're developing your future wisdom that's going to be valuable to you. Okay. Final question.

1:15:26

You were on the board of Burning Man or you still are. Uh it was for us.

1:15:32

I I helped found the board of Burning Man. Yeah. Okay. No big deal.

1:15:32

So I don't know if you know this.

1:15:37

I got married at Burning Man.

1:15:37

We had a unofficial wedding there on bicycles.

1:15:37

So, it's really meaningful to us.

1:15:41

I've been there four or five times.

1:15:41

Uh, what's something about Biringham that maybe people don't know some insight story or a really unexpected piece of this the journey?

1:15:52

I may imagine there's a lot, but what comes to I would say the best not well-known thing about Burning Man is that Burning Man owns a place called Fly Ranch and Fly Ranch is about 10 miles from Burning Man.

1:16:05

Now, if when you go to the burn, uh the event in, you know, around Labor Day, uh you cannot go over there, it's it's it's locked off. It's 3,400 acres.

1:16:11

But if you do, if you look at Fly Ranch, um fly ranch.

1:16:19

org, I think it might even be or it's on the Burning Man site.

1:16:19

Fly Ranch is like the opposite of Burning Man.

1:16:25

Burning Man is this alkaline desert.

1:16:25

Like there's no no living life there at all. It's very masculine.

1:16:30

Fly Ranch is like porous and and like lots of like desert grasses and hot springs and hot pools and it and birds and wild horses and it's one of my favorite hot springs places in the world.

1:16:47

Um so just check it out and you can go there when it's not during the event and and it's it's quite beautiful.

1:16:54

Feels like it might have inspired uh MEA in many ways. It didn't. Yes.

1:17:00

Chip, two final questions.

1:17:00

Where can folks find you online and how can listeners be useful to you? So online, meowisdom.

1:17:06

com is the website for MEA. My website's chipconley. com, co- ny. And uh I'm on LinkedIn.

1:17:14

That's really from a social media perspective, the thing that I do the most.

1:17:19

I actually take my daily blogs and put them on LinkedIn.

1:17:19

So, and then what the what the your community can do, just Yeah. Come say hi. come uh check me out.

1:17:26

And if wisdom is interesting to you, and I think wisdom should be interesting to everybody here, um on the MEA website at the very bottom footer, you will see a bunch of free resources.

1:17:38

One of them is called Why Successful Leaders Value Wisdom. It is a free resource.

1:17:43

Um and there there's also a free resource down there called the Anatomy of a Transition.

1:17:49

Those two free resources, understanding how to build your TQ, your transitional intelligence and understanding how to develop wisdom are two, to my mind, two of the most important modern skills that we can have.

1:18:04

It's funny when you say you're on LinkedIn.

1:18:04

It feels doesn't resonate with me.

1:18:04

You can chip conly on LinkedIn posting on LinkedIn.

1:18:08

So, I don't know why because I'm a little too Burning Man.

1:18:15

You're just Yeah, exactly.

1:18:15

It feels like that's not your vibe.

1:18:15

But I love that you do it because that's where the people are.

1:18:20

Oh, I I put wild weird stuff up on LinkedIn and you know, thank thank God somebody's doing that.

1:18:26

I got for some reason I don't see it. I need to fix that.

1:18:26

Chip, this was incredible.

1:18:31

Everything I was hoping it'd be, thank you so much for being here and for sharing your wisdom.

1:18:33

I am so proud as I go back like I'm your proud papa who just loves to see you in your element.

1:18:41

And I just want to say make sure everybody knows the following.

1:18:41

Lenny was so good to work with.

1:18:46

I really when whenever you were assigned to a pro uh project as a PM, I appreciated it because I just knew that we were gonna have great conversations and you're you're just an interesting dude.

1:18:59

Well, I appreciate that, Chip.

1:18:59

That's going to be the beginning of this whole episode.

1:19:02

We're just going to put that up front. Just kidding. That was awesome, Chip. Really appreciate it.

1:19:06

Uh and thanks everyone for listening. Bye, everyone.

1:19:06

Thank you so much for listening.

1:19:12

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1:19:16

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1:19:21

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1:19:26

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