The Lies We Tell Ourselves About Aging and Success | Why Your Best Years Are Still in Front of You

0:00You have a lot more time than you think. it is super appropriate for you to start that business that you've always wanted right now. It is actually quite practical. You probably actually have a much deeper understanding of what to do to be successful than the average 25-year-old that's rolling into my office looking for dollars to start their business because they've got an idea. If I could just take the energy in my heart to deploy it into so many people's brains to understand how much time, how much time is still left in your life to do your thing, that would make me very happy. That would make me so happy because I do believe, as I'm spending a lot of time, maybe I'm affected by my last 15, 20 hangouts with such age group individuals, way too many people are starting to plot their exit, their unwind, and I'm like, Jesus, you may have 50.

0:53That's right, with modern medicine, you may have 50 more good years of executing. 40 for sure. I really think, you know, knock on wood, so many of you watching this have 40 full big years. Think back to when you were 10. From that moment till right now, all that life you've got on the back end and people are trying to wind down and figure out how they're going to slow it down or wrap it up. Fuck wrapping it up, man. Start it up. You're just 50. All right. If you just heard that and felt something, then good because that's exactly what we want out of today's episode. Too many people hit a certain age and start believing the lie that they're running out of time.

1:32that their best years are behind them. But the truth is, you probably have more time ahead of you than you realize. And if you still don't believe that, let's talk about someone who proves it. Chip Conley. He is a hugely successful entrepreneur who built a massive hotel brand and could have retired comfortably. Instead, at age 52, he joined Airbnb, a company full of employees half his age. Rather than feeling out of place, he turned his experience into his biggest advantage. Here's his story. Seven years ago, I was asked by the three founders of Airbnb to come help them grow their company into a global hospitality brand.

2:07So I've spent seven years as Brian Chesky's mentor, and I was the head of global hospitality and strategy for the company for four years full time. And then for the last three years, just been like a strategic advisor to them. That's cool. Yeah. So that the thing that and part of the reason I'm here is because while I was there, you know, they called me a curious white boy when I was in high school. They called me the modern elder at Airbnb, and I did not like that. But I was twice the age of the average employee at Airbnb. I started when I was 52. I'm 59 now. For everybody who's listening, my great run in kind of the Silicon Valley investment world definitely was kind of like 05 to like 06 to like 2010.

2:47And what's interesting about hearing this story is that Chip absolutely like was in those circles with me. and it was just like, there was probably like 40 to 150 people that weren't hardcore tech, had come from different backgrounds, but were kind of like in the mix, one way or the other. And so it's really fun to hear that that's where you ended up and it makes so much fucking sense because the value prop on context and reps that you were able to bring that exact company is like the most logical shit I've ever heard. Well, it was so funny because when I joined, First of all, for the first five months, we didn't tell anybody I joined.

3:26So we didn't tell the press. We wanted to see how Brian and I got along. Where did you meet Brian originally? Brian just called me. He just called me out of the blue. He said, you know, one of the things I will say about Brian, Brian, you know, a lot of people think it's the hubris that makes you a great CEO. It's actually the humility. And in Brian's case, he's had the humility to say, I don't know a bunch of stuff. So I'm going to go out and when it comes to hospitality, I'm going to go talk to this guy who's in San Francisco, who's created a boutique hotel company. and he's an entrepreneur.

3:53Who's in the mix with our community, which really mattered at the time. That's true. It always does, but I remember it very vividly. Oh my God, all the people who looked at me like, what the hell are you doing? When it finally was announced five months later, it's like, why would you? My brother in the hotel world had no clue what Airbnb was. And so, long story short, it led me to becoming this modern elder. And I'm like, what the hell is a modern elder? So the traditional elder of the past was all about reverence. You revered your elders. But a modern elder is about relevance. And so you better be as curious as you are wise.

4:28So at age 52, I was joining a tech company for the first time. I didn't understand the lingo, but I had to learn. And so what I had to do was be humble. I had to be open to like saying, I don't know what you fucking mean by saying you're gonna ship a feature. Explain that to me. And so I was the person who could come in and make the bridges and create the bridges to the travel industry. And I was Brian's mentor and helping him to look at leadership from a CEO's perspective. But the problem in our society today, and I think you've talked a little bit about this in the past, is we're going to live longer, power is moving younger, and the world is changing faster.

5:06And there's a collection of people in midlife who feel irrelevant and bewildered. And have a ton to give. They do. But to your point, and I'm sure my team smiled because it's a word I talk a lot about, it's going to take humility on both fronts. For sure. There are a lot of people who are 45 to 60 years old who just are complaining about millennials and they're not actually asking how they are getting back in the mix by becoming a beginner again. And aren't being held accountable for parenting and creating the millennials. It's my favorite dynamic right now. That too. Literally, I go to these dinners or whatever and they're shitting on it and I'm like, you're the parent.

5:45You're the one that created this entitlement because everybody had to have a fucking trophy. Here's the thing I've learned. I had something to teach Brian. Brian had something to teach me. A thousand percent. And I had 100 mentors over my seven years now at Airbnb and each one of those, 100 mentees, I'm sorry, 100, 100, well, interesting I said that. I said I had 100 mentors. Well, I did. I was gonna say 100 mentees but mutual mentorship is the future of learning and development in the companies. I am such a fucking buyer of what you're putting down right now. I think we're about to go through the golden era.

6:17We're going through it at Vayner. I hired a new chief creative officer and I told him one of the things I want to do in 2020 is hire retired copywriters literally from the madman era. There's so much to bring to the table. Nobody looks at them as a viable option. I literally can't wait to hire them. A, a lot of them are so financially sound on the East Coast here anyway that they'll be thrilled to work for minimum wage, let alone something more than that. And it'll be fun. And the kids are gonna learn. After it's the tech industry, I think the advertising industry probably has the highest level of ageism out there.

6:54I think that's right. I'm such a foreigner to it, and now that I'm in it, I'm like, yes. I don't understand how you're not as creative at 52 as you were at 39. It's silly. You're 44? Poor. Okay, a couple thoughts on 44. 44, frankly, you're right there. Your life has been different than the average person, but you know the lowest point of happiness across cultures is about age 47. Interesting. So what happens is this U-curve of happiness. Three years away. Yeah, you're fine, you're fine. I'll be okay. Listen, how long are you gonna live, first of all? I think 111 for me. 111, wow. So if you live to 111, you're probably not even into the second quarter of your adult life yet.

7:34You're preaching. I'm not even sure I left the dugout yet. So when I recently was hanging out with my dad scuba diving in Indonesia and I did it. Yeah, just cash. Cash. And we were, I went on one of those online sites, threw my data in there and they said I was going to live until 98. That's cool. And I did the math and this was two years ago. This was a year and a half ago, two years ago. And I was 57 at the time. And the truth is if I do live until 98, at age 57, I was not even at halftime of my adult life starting at age 18. I understand. So you're probably, if you live to 111, you might be going into the second quarter.

8:07Listen, my relationship with time and the ability to be hyper but have a great patience graph is something that I beat the drum of very heavily because it will help people because so many people are anxious because they think they have to figure it out at 30. Well, they see these people like Branceschi and - But there's like seven of them. Yeah, exactly. I keep reminding them. There's fucking 42 of these people. This is why a lot of people feel entitled. No shit. Or they feel the sense of prior, Like, if he can do it, I can do it. It's still wildly not being talked about. No, no. Ageism, or even just the subject of age diversity, it's been proven that actually age is the number one form of diversity on teams.

8:43So better than race diversity. I mean, we need all kinds of diversity. Let's start with that. But age is a more effective form of diversity than race, gender, sexual orientation, et cetera, for a lot of reasons. Primarily because our brain is different as we're older versus younger. I've like, not exhausted, but I've done a very good job for my own self judging my own self over the last 36 months to really pounding a certain conversation to a certain demo, I'm wildly excited about 55 to 90. Yeah. Like, I really am. This is your modern elder period. No, no, I like it. Forget about me. Yeah. I want fuckers to realize they're 52 and they're gonna live for another 38 years, minimumly, and like, what the fuck are you wrapping it up?

9:22Yeah, exactly. The fuck are we talking about? No, it's crazy. It's crazy. All the rules, Chip, are predicated on when people live to 40. All the rules. Yeah. Well, so at age 47 was the longevity in the year 1900 and it was 77 by the year 2000. So we added 30 years of longevity in one century. But we also introduced a whole new concept, which is the midlife crisis in 1965. And now it is 55 years later and we've done very little to address the midlife crisis, so to speak. And so my premise, and you know, midlife suicide are up 50 % compared to the year 2000. There's a new word in the academic world called middle essence.

10:03So adolescence, we know what an adolescent is, but that word is only 115 years old. So prior to the word adolescence being in the lexicon 115 years ago, people at age 13 when they hit puberty were an adult. And you got married and you had kids and you worked in the mines, etc. And then adolescence became a clear new sort of life stage. I like what you're doing with this. It's the life stage between childhood and adulthood. So we have middle essence. It's the stage between adulthood and elderhood. Elderhood is different than elderly. Elderhood is a relative term. At Airbnb, I learned the hard way.

10:37I was a modern elder because I was twice the age of the average employee there. So I owned the word. Chip's story proves something most people overlook. Your experience isn't a limitation. It's your leverage. But let's get even more practical. What should you actually focus on if you're in your 40s, 50s, and beyond? In this next clip, Gary takes a question from an older entrepreneur who wants to know, what's my biggest asset now? And Gary's answer is not what most people expect. Let's take a listen. You talked a little while ago about the 19-year-old entrepreneur. Yes. The biggest asset is patience.

11:13Yes. What is the older entrepreneur? What should they have as their asset? Because I'm not patient. Three years ago, I started a business with some other guys. We're now 80 people turning over 10 million pounds. Amazing. I'm not patient. You want more? Absolutely. It's fantastic. This is amazing. What's my biggest asset now? Well, I think your asset is experience. All the cliche stuff. It's just cliche. It's, you know, everybody said it. What I think, though, is do I think, instead of saying experience, I'm going to tweak it a little bit. Do I think a 46-year-old man has a better chance of knowing himself than a 19-year-old man?

11:49Yes, I do. I think we've all gone through it, right? Even think about your transition from high school to university. You just get there, right? You get more comfortable with yourself. The second you get more comfortable with yourself, you start being more honest with yourself. Da, da, da, da, da, da. So at this point in your life, in my life, in your life, we should really know ourselves. And so, it's even interesting for me to hear that you started with a couple other gentlemen. To me, my hope for my own kind of like personal picture that I'm trying to paint here is that the three of you had some crossover skills but you're all maintaining your core skill and that's what's helping the business, right?

12:23you're taking care of this, that person might take care of that, and the other person's there. That's a very common thing for older entrepreneurs because at that point, they've shed their wants and their romance about being the best sales guy or the best sales girl. And now they know, I'm really good at CFO finances. I'll never let us go out of business. I've got the numbers. Don't worry, guys. You go be crazy because I'm going to make sure we pay our bills. you go make sure the staff loves us and now we've got this. I was gifted that I do a lot of the principles well. All of them. Finance probably being my weakest it's probably the one that's most commoditized and when you're in business with your dad and your brother if they steal from you it's a good story.

13:04Right? So I think that your biggest advantage is that you got it's probably the narrative to why you were succeeding. Now the question becomes a more interesting one. I'm going to take you in a different place that's probably more grounded in the actual energy. I think the big thing now at this point in your life is to really try to figure out very quickly what you want to happen. And the problem is you have two other people that may want different things. But if you're able to align that you guys want to sell the company soon because that's a real cash out on that kind of revenue, then all of your behaviors have to go in that direction.

13:42You have to figure out who you can sell to. You have to start becoming a media company to them. One of the great misplays of brand is if I wanted to sell VaynerMedia tomorrow, it would happen in 30 minutes. Not on revenue on the fact that I would market to the people that could actually buy me. I don't think Martin Sorrell knows who I am. In 20 minutes, he would want to rip his arm off to buy us. That's what I'm good at. So what I would love to know is how aligned are you guys? And if you're aligned, make all your actions go in that direction. That's interesting to me, right? That's where you can really make something amazing happen.

14:15So I think that's something to really give some serious thought to. But I think it's self-awareness at this point. You've got so much more history in your 20, 30 years of entrepreneurship that allows you to, and you should shed even, whatever pride you have left in principles that you don't bring to the table as well as you know part or two, the more you can shed down to only focusing on what you do. Me and AJ are so efficient because we do not discuss the things that we know the other person's better at. We don't even talk about it. You know? Big. And when one broaches the subject, the other gets pissed.

14:54Right? Because why would we even waste time? You know I'm better at this than you. And we've become efficient. Like fucking efficient. You know? And time is the asset. So why debate? Got it? Yeah, it's great. We're on the path. And the other thing I would tell you, I would highly recommend you forcing your other two partners to over-communicate with the three of you at all times. Force communication right now. You're successful and you're at this age. This is an interesting time. Force communication. Anything that you think is sitting in your heart that needs to be talked about with your other two partners, I would tell you to do that tomorrow.

15:31The quicker you get it out, the better you're going to be. By now, hopefully you're getting it. Your 40s and your 50s aren't the end of something. They're the start of something new. And here's the thing. Most people don't actually feel old at 50. In fact, many say they feel sharper, younger, and more energized. That's exactly what came up when Gary sat down with radio legend Elvis Duran, host of one of the most successful morning shows in the country. They talked about how at 40 or 50, you actually feel like you're just getting started, but for some reason society still tries to convince us otherwise.

16:02Listen to this. First of all, I am sick and effing tired of people calling millennials lazy and not caring and not wanting to contribute. And I'm tired of it because I don't believe it. I think everyone has an equal opportunity to be lazy or dynamic. You're preaching. I mean I get this all the time because I have such a big fan base of 40, 50, 60 year old executives and they're like, how do you deal with these millennials? And I'm like look, there's no... Stop calling them millennials. There's no millennials. There's Rick. There's Susan. There's Sarah. Right? I know unlimited 40 to 50 year olds that are lazy and have no drive and I have tons of 23 year olds that work at VaynerMedia that if I give them$1 more an hour they'll work 72 hours in a 24 hour day.

16:48Talk about it then. I'm 22 years old. I'm paying off my debt from college. We should get into that racket to begin with. So if I'm 22 years old I've got the whole world ahead of me. I've got more opportunity than most people so why am I branded a loser? Because old people want to complain about the next generation. We become bitter. So don't listen to them. Of course not. So 22-year-old, let's say I'm 22. Tell me what I need to be doing right now to make my... Every 22 to 30-year-old that's listening to this right now, you have one major flaw I'm generalizing. You have lack of patience. Elvis, if you really want to talk about it, what people are making is they've got college debts, they've got their ambitions, one of the two.

17:29Let's say it's a positive, let's say it's a negative. And they pop out at 22, 23, and they take jobs that pay them$4 ,000 more for something they don't want to do because they lack patience. Wow. Uh-huh. That's the punchline, my friend. Like, if you... Do what you want to do. Can I, can I, can I? How old are you? 52, almost. Are you blown away as I am as a 40-year-old man how young you feel? Oh, yeah. If I told 25-year-old Elvis at 52 you would feel like this, you would... No, I feel better. No, no, these are the days. Winston Churchill, my favorite quote. These are the days. And that's the punchline.

18:03If I could wish anything right now, I would wish that everybody who's listening that's under 30 could feel what you and I feel right now. I mean, I don't even feel like I've started. You know, and so when you're 22, I remember being 22. It wasn't that that long ago. 40's old. I would have been like, oof. Like, that would have, like, in that 18 years, I better have, if I'm gonna buy the New York Jets like I want to, I better have done it there. Now I realize, my God, life is so long. And the way we're taking care of ourselves, you know, your parents, my parents at our ages, They were not as healthy.

18:37We're gonna live much longer. We're gonna live into our 90s, 100s. We have so much time. I'm gonna go beyond that. Okay, respect. So the punchline, the punchline, in one way or the other, I would ask everybody who's listening right now to take one step back and say, okay, either I'm working too hard and I'm stressing these loans or what I have to achieve to prove to my dad that I'm good, right, and I'm not going to Coachella or this and that or you're doing too much of that stuff and you can work little harder but you've got so much more time. And so I think the one thing, and it was funny, was that awkward pause that we all just took.

19:11Patience is something we do not talk about. Well, and it's something that it doesn't seem to be valued right now because if you notice, like I remember, this is years ago, but back when Oprah was on and had her show every day, she did so many episodes about young kids who are geniuses or young kids who are 10 and already graduated college. And so in our society we're being told that the faster you do something, the better you are. It's why listening to society is a bad idea. If you listen to society, the world's on fire and we're all gonna die. If you listen to society, everybody's gonna build Facebook and Snapchat.

19:45Then who do we listen to? Ourself? Listen to yourself. Now the problem is a lot of us don't like what ourselves are telling to ourselves. The inner voice can be our worst enemy. That's right. So first and foremost, what I think everybody should do and even I'm saying this actually I'm giving myself advice right now I'm just getting meta and stepping away from this interview, you need to do things that make you a little uncomfortable. Way too many people have made decisions without ever trying. Right? So that's one thing that I think. So like it's too scary, I don't want to do it. That's right and you have to taste things.

20:16I love when people are like, oh I hate sushi. I'm like have you had it? They're like no. That's me. That's right. I don't want to taste it. Right. And so to me that's the most fascinating thing of how humans are, right? Like that's what we do. And so the punchline is this. Look, here's what I'll say on this little genre as we're jamming on it. You have one life. One of the great things that happened to me growing up was there was a lot of grandparents that visited. I had a lot of kids in my neighborhood. And for some unknown reason, I don't know if I'm an old soul or what it is, I used to, on the playground, go and sit with old people.

20:49And just talk to them. And let me tell you one thing about old people. 80, 90. The one thing that has stuck with me as a child and sits with me today is they regret. Regret scares the crap out of me, Elvis. Do you have any regret right now? No, but I also am 40, so I feel like I can get a lot of things done. I feel like a lot of things are still in front of me. But when you get to 80 and 90 and you can't do everything and you know that you don't have as much time, the one thing I see in so many of their eyes is I wish I. Think about that. How different life actually feels at 50 compared to what you thought when you were 25.

21:24Let's zoom out. This isn't just about work. It's about how we see aging in general. For years, we've been taught that life has a timeline, that by a certain age, you should have everything figured out. And if you don't, then it's too late. Gary, however, has spent his entire career proving that's bullshit. In this next clip, you'll hear a mashup of his best takes on age, patience, and why we've all been thinking about time the wrong way. Hey guys, it's Gary, and I've got 50 seconds for you. This is 50 seconds for every 50-year-old in the world. I need you to understand something. You have so much time.

22:02I'm in entrepreneur land and I meet with all these kids. Show these kids. Show these kids. All these kids and they're taking advantage of the new world. Right? But they're young and they're raw and they've got a lot of great and some of them are great and they'll be all time great. But what blows me away is how many of you have decided that you're finished. That you're on the back end of your life. That you can't accomplish it. That this wasn't built for you. I'm 41 years old. I didn't grow up with this shit either. But I figured it out. You figured out how to drive, you figured out how to be a parent, you figured it all out.

22:32And with the health trends and the way the world is now, you've got a long life in front of you. So instead of sitting in that job for the next 10 years, go do your thing. You've got plenty and plenty of time. Are you 54 and thinking that you're wrapped up because you have 24 year old children and you've decided that all the dreams you had are over and you couldn't accomplish them? You haven't even fucking started. And I know the comments are gonna come in and be like, what the fuck are you talking about? Here's what I'm talking about. You have 30 remarkable fucking years of execution in front of you.

23:01We live in a world now where 54 year olds can take advantage of this just as much as 13 year olds and instead of dwelling of what you have not accomplished, how you fucked up that marriage, took that wrong job, went to the wrong school. Please, step up, change your perspective right now. What you've done over the last 600 plus months means nothing when it comes to what you're about to do with the rest of your life. Especially when you factor in, you have 54 years of knowing what not to do. Why don't you spend the next 30 doing the other shit? So hopefully now you see it. Time isn't your problem, your mindset is.

23:38At this point, only one question left. Are you actually going to do something about it? This next clip is one of Gary's most powerful rants ever, in my opinion. If you've been sitting on ideas, taking yourself out of making moves or thinking, I'm too old to start, this will shake that belief out of you. The Monday rant video was reverse engineered. Like it just, I just knew that people would like want to watch it. And like, and that's what I also think is going to happen here. Basically, I want this film to give you the audacity to actually go out and do it. You're 52 years old and it's not being talked about enough that, hey man, hey gal, like it's not over.