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

Summary

Podcast Summary: The GaryVee Audio Experience

Episode: The Lies We Tell Ourselves About Aging and Success | Why Your Best Years Are Still in Front of You
Release Date: March 18, 2025
Host: Gary Vaynerchuk
Guest: Chip Conley
Co-Host: Elvis Duran

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1. Introduction: Challenging Age-Related Myths

The episode kicks off with Gary Vaynerchuk addressing a pervasive societal myth: the belief that aging marks the decline of one's potential and the nearing end of their best years. Gary passionately argues against the notion that time is running out for individuals, especially those in their 40s and 50s, to pursue their entrepreneurial dreams.

Notable Quote:

"Fuck wrapping it up, man. Start it up."
— Gary Vaynerchuk [00:10]

2. Chip Conley’s Journey: From Hospitality to Airbnb

Gary introduces Chip Conley, an accomplished entrepreneur who, at 52, chose not to retire after building a successful hotel brand. Instead, Chip joined Airbnb, bringing his extensive experience to a young, dynamic company. Chip's role evolved from mentor to strategic advisor, showcasing how seasoned professionals can add immense value even in tech-driven environments.

Key Highlights:

• Chip Conley was head of global hospitality and strategy at Airbnb for four years before becoming a strategic advisor.
• His entry into Airbnb was initially kept under wraps to assess mutual compatibility with CEO Brian Chesky.
• Despite facing stereotypes as a "modern elder," Chip leveraged his age and experience as strengths rather than obstacles.

Notable Quote:

"A modern elder is about relevance. And so you better be as curious as you are wise."
— Chip Conley [03:57]

3. Embracing Age Diversity and Overcoming Ageism

The conversation delves into the critical issue of ageism, particularly in industries like advertising and tech. Chip emphasizes that age diversity is a powerful asset, often surpassing other forms like race or gender diversity, due to the varying perspectives and experiences different age groups bring.

Key Insights:

• Age Diversity: Age is highlighted as the number one form of diversity on teams, enhancing creativity and problem-solving.
• Midlife Challenges: Chip introduces the concept of "middlescence," a life stage between adulthood and elderhood, paralleling adolescence. He discusses the rise in midlife crises and related mental health challenges.
• Humility and Continuous Learning: Both Gary and Chip stress the importance of humility, especially for older professionals, to stay relevant and effective in rapidly changing industries.

Notable Quote:

"We are going to live longer, power is moving younger, and the world is changing faster."
— Chip Conley [05:10]

4. The Power of Patience and Experience for Older Entrepreneurs

Addressing an older entrepreneur's question, Gary underscores that experience is the most substantial asset for entrepreneurs in their 40s and beyond. He elaborates that self-awareness and the ability to align business goals are crucial for sustained success.

Practical Advice:

• Self-Knowledge: Older entrepreneurs have a deeper understanding of themselves, enabling better decision-making.
• Alignment: Ensuring that all business partners share unified objectives is vital for achieving common goals.
• Forced Communication: Maintaining open and continuous communication within a business team helps in resolving conflicts and aligning strategies.

Notable Quote:

"Your biggest advantage is that you got... what you have is experience."
— Gary Vaynerchuk [11:32]

5. Challenging Generational Stereotypes

Elvis Duran joins the discussion to dismantle negative stereotypes about millennials, advocating for recognizing individual efforts over generational labels. The hosts highlight that qualities like patience and perseverance are not confined to any age group but are essential across all stages of life.

Key Points:

• Individual Over Generational Labels: Instead of categorizing behaviors based on generations, focus on individual traits and circumstances.
• Patience as a Universal Virtue: Both older and younger entrepreneurs benefit from cultivating patience to navigate their respective challenges.
• Redefining Success: Success should not be measured against arbitrary timelines but based on personal growth and fulfillment.

Notable Quote:

"Patience is something we do not talk about."
— Elvis Duran [19:13]

6. Reaffirming the Potential of Midlife and Beyond

The episode reinforces the message that life in one's 40s, 50s, and beyond is not a winding down but a phase filled with potential and opportunities. Gary and Elvis encourage listeners to shift their mindset from seeing age as a barrier to viewing it as an asset.

Encouraging Insights:

• Extended Longevity: With advancements in healthcare, individuals can expect to live healthier and more productive lives well into their later years.
• Opportunity for Reinvention: Midlife offers a chance to pivot, explore new passions, and embark on entrepreneurial ventures without the constraints often felt in younger years.
• Legacy Building: Engaging in meaningful projects during these years can leave a lasting impact and provide a sense of accomplishment.

Notable Quote:

"You are 52 and you're gonna live for another 38 years minimumly. And, like, what the fuck? Are you wrapping it up?"
— Gary Vaynerchuk [09:24]

7. Final Call to Action: Seize the Remaining Years

In a powerful closing segment, Gary delivers a passionate rallying cry for listeners to embrace their remaining years with vigor and purpose. He urges those in their midlife and beyond to leverage their experiences, shed unnecessary limitations, and take decisive actions toward their entrepreneurial goals.

Actionable Steps:

• Embrace Learning: Continuously educate yourself about new technologies and market trends to stay competitive.
• Prioritize Self-Awareness: Understand your strengths and weaknesses to effectively lead and grow your business.
• Overcome Regret: Let go of past mistakes and focus on building the future you desire.
• Utilize Experience as Leverage: Apply your vast experience to navigate challenges and make informed decisions.

Notable Quotes:

"You absolutely do [have time]. There are absolutely a ton of entrepreneurs that started their companies in their 40s, 50s, 60s and 70s."
— Elvis Duran [25:28]

"Entrepreneurship is not predicated on taking away from your family. Entrepreneurship is from taking away from everything else. So stop making excuses."
— Gary Vaynerchuk [25:28]

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Conclusion: Embracing the Future with Confidence

The episode concludes by reiterating that age is not a hindrance but a unique advantage in the entrepreneurial landscape. Gary Vaynerchuk, alongside Chip Conley and Elvis Duran, empowers listeners to redefine their relationship with time and age, encouraging them to harness their accumulated wisdom and experience to achieve unparalleled success in the years ahead.

Final Takeaway: Your best years are not behind you—they are the foundation for a future filled with possibilities. Embrace your age, leverage your experience, and take bold steps toward your entrepreneurial aspirations.

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End of Summary

Transcript

[Gary Vaynerchuk]

You 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.

[Elvis Duran]

If I could just take the energy.

[Gary Vaynerchuk]

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. That'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.

[Elvis Duran]

So many of you watching this have 40 full big years, think back to.

[Gary Vaynerchuk]

When you were 10.

[Elvis Duran]

From that moment till right now, all that life you've gone on the back.

[Gary Vaynerchuk]

End and people are trying to wind down and figure out how they're gonna slow it down or wrap it up. Fuck wrapping it up, man. Start it up.

[Elvis Duran]

You're just 50, alright?

[Narrator]

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, that 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.

[Chip Conley]

Seven years ago, I was asked by the three founders of Airbnb to come help them grow their company into a global hospitality brand. So 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.

[Gary Vaynerchuk]

That's cool.

[Chip Conley]

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.

[Gary Vaynerchuk]

For everybody who's listening, my great run in kind of the Silicon Valley investment world definitely was kind of like 05 to 06 to 2010. And what's interesting about hearing this story is that Chip absolutely, like, was in those circles with me, and it was just like.

[Elvis Duran]

Like there was a bunch.

[Gary Vaynerchuk]

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 makes. It's really fun to hear that that's where you ended up and how 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.

[Chip Conley]

Well, it was so funny because when I joined, first of all, for the first five months, we didn't tell anybody I joined, so we didn't tell the press. We wanted to see how Brian and I got along, because I was.

[Gary Vaynerchuk]

Where do you meet Brian? Originally?

[Chip Conley]

Brian just called me. He just called me out of the blue. He said, makes sense.

[Gary Vaynerchuk]

One of the things I'll say about.

[Chip Conley]

Brian, Brian, a lot of people think it's the hubris that makes you a great CEO. It's actually the humility, 100%. And in Brian's case, he had the humility to say, I don't know, a bunch of stuff. So I'm gonna go out, and when it comes to hospitality, I'm gonna talk to this guy who's in San Francisco, who's created a boutique hotel company.

[Elvis Duran]

He's an entrepreneur who's in the mix with our community.

[Gary Vaynerchuk]

He's in the mix which really mattered at the time.

[Chip Conley]

That's true.

[Gary Vaynerchuk]

He always does. But I remember it very vividly.

[Chip Conley]

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.

[Gary Vaynerchuk]

Well, that was your old.

[Chip Conley]

My brother in the hotel world had no. They had no clue what Airbnb was.

[Gary Vaynerchuk]

Yeah, it was the most.

[Chip Conley]

Anyway, long story short is it's been. It led me to becoming this modern elder, and I'm like, what the hell's 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. So 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 going to 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. And there's a collection of people in midlife who feel irrelevant and bewildered and.

[Gary Vaynerchuk]

Have a ton to give.

[Chip Conley]

They do.

[Gary Vaynerchuk]

But to your point, and I'm sure my team smiled because it's a word I talk a lot about. It's gonna take humility on both fronts, for sure.

[Chip Conley]

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.

[Gary Vaynerchuk]

Beginner again and aren't being held accountable for parenting and creating the millennials. It's my favorite dynamic right now. Literally, I go to these dinners or whatever, and, like, they're shitting on it, and I'm like, you're the parent. You're the one that created this entitlement, you know, because everybody had to have a fucking trophy.

[Chip Conley]

Here's the thing I've learned. You know, I had something to teach Brian. Brian had something to teach me thousand percent. And I had 100 mentors over my seven years now at Airbnb, and each one of those hundred mentees. I'm sorry, I had 100 met. Well, interesting. I said that. I said I had 100 mentors. Well, I did. I was going to say 100 mentees, but mutual mentorship is the future of learning and development in companies.

[Gary Vaynerchuk]

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. We'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 Mad Men era. There so much to bring to the table. Nobody looks at them as a viable option. I literally can't wait to hire them.

[Elvis Duran]

A.

[Gary Vaynerchuk]

A lot of them are so financially sound on the east coast here anyway, that like, they'll be thrilled to work for minimum wage, let alone something more than that. And it'll be fun and the kids.

[Chip Conley]

Are gonna learn after the tech industry, I think the advertising industry probably has the highest level of ageism out there.

[Gary Vaynerchuk]

Because I think that's right. I'm such a foreigner to it. And now that I'm in it, I'm like, there's.

[Elvis Duran]

Yes.

[Gary Vaynerchuk]

I don't understand how you're not as creative at 52 as you were at 39. It's silly.

[Chip Conley]

People's at your 44. Okay, 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 in. In across cultures is about age 47.

[Gary Vaynerchuk]

Interesting.

[Chip Conley]

So what happens is this new curve of happiness three years away. Yeah, you're fine, you're fine.

[Gary Vaynerchuk]

I'll be okay.

[Chip Conley]

Listen, if you. How long are you gonna live for?

[Gary Vaynerchuk]

First of all, I think 111 for me.

[Chip Conley]

One hundred and eleven. Wow. I did some. So if you live to 111, you're probably not even out into the second quarter of your adult life yet.

[Gary Vaynerchuk]

You're preaching, people. I'm not even sure I left the dugout yet.

[Chip Conley]

So when I recently, I was hanging out with my dad, scuba diving in Indonesia. And.

[Gary Vaynerchuk]

Cash.

[Chip Conley]

Yeah, I can't use cash.

[Gary Vaynerchuk]

Cash.

And we were.

[Chip Conley]

I went on one of those online sites, threw my data in there, and they said I was gonna live till 98.

[Elvis Duran]

That's cool.

[Chip Conley]

I did the math. And this was two years ago. This is a year and a half ago. Two years ago.

[Gary Vaynerchuk]

And.

[Chip Conley]

And I was 57 at the time. And the truth is, if I do live till 98 at age 57, I was not even at halftime of my adult life. Starting of your adult life at age 18. So you're probably. If you live to 111, you might be going into the second quarter.

[Gary Vaynerchuk]

Listen, 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. Cause they think they have to figure it out at 30.

[Chip Conley]

Well, they see these people like Brian Chesky and.

[Gary Vaynerchuk]

But there's like seven of them.

[Chip Conley]

Yeah, exactly.

[Gary Vaynerchuk]

So they keep reminding them there's 5, 42 of these people.

[Chip Conley]

This is why a lot of people feel entitled or they feel. Or they feel the sense of priority of like, if he can do it, I can do it.

[Gary Vaynerchuk]

It's still wildly not being talked about.

[Chip Conley]

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. So 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.

[Gary Vaynerchuk]

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. I really am.

[Chip Conley]

This is your modern elder period.

[Gary Vaynerchuk]

No, no, I like it. Forget about me.

[Chip Conley]

Yeah.

[Gary Vaynerchuk]

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?

[Chip Conley]

Yeah, exactly.

[Gary Vaynerchuk]

The fuck are we talking about?

[Chip Conley]

No, it's crazy.

[Elvis Duran]

It's crazy.

[Gary Vaynerchuk]

So the rules, Chip, are predicated on when people live to 40.

[Elvis Duran]

All the rules.

[Chip Conley]

Yeah. 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 preference and, you know, midlife suicide are up 50% compared to the year 2000. There's a new word in the academic world called middlescence. So adolescence, we know what an adolescent is, but that word is only 115 years old. So that 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, et cetera. And then adolescence became a clear news or life stage.

[Gary Vaynerchuk]

I like what you're doing with this.

[Chip Conley]

The life stage between childhood and adulthood. So we have middlese. 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. I was A modern elder because I was twice the age of the average employee there, so I owned the word.

[Narrator]

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.

[Entrepreneur]

You talked a little while ago about the 19 year old entrepreneur.

[Gary Vaynerchuk]

Yes.

[Entrepreneur]

The biggest asset is patience.

[Gary Vaynerchuk]

Yes.

[Entrepreneur]

What does the older entrepreneur, what should they have as their asset? Because I'm not patient. Three years ago I started a business with some, some other guys. We're now 80 people turning over £10 million.

[Gary Vaynerchuk]

Amazing.

[Entrepreneur]

I'm not patient.

[Gary Vaynerchuk]

You want more?

[Entrepreneur]

Absolutely. It's fantastic.

[Gary Vaynerchuk]

This is amazing.

[Entrepreneur]

What's my biggest asset now?

[Gary Vaynerchuk]

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.

[Elvis Duran]

To tweak it a little bit.

[Gary Vaynerchuk]

Do I think a 46 year old man has a better chance of knowing himself than a 19 year old man?

[Elvis Duran]

Yes, I do.

[Gary Vaynerchuk]

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.

[Elvis Duran]

Da da da da da da da.

[Gary Vaynerchuk]

So at this point in your life and my life and 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 from my own kind of 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. You'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 principals. 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, Right. 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. You 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. So 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, partner to 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.

Right?

Because like, why would we even waste time, you know, I'm better at this than you. And we've become efficient, like efficient, you know, and Time is the asset. So why debate? Got it.

[Entrepreneur]

Yeah, it's great. Yeah, we're on the path.

[Gary Vaynerchuk]

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. Like forced communication. Right now you're successful and you're at this age. This is an interesting time, like forced 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. The quicker you get it out, the better you're going to be.

[Narrator]

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. Listen to this.

[Elvis Duran]

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. Cause 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.

[Gary Vaynerchuk]

You deal with these millennials? And I'm like, look, there's no.

[Elvis Duran]

Stop calling them millennials.

[Gary Vaynerchuk]

There's no millennials.

[Elvis Duran]

There's Rick, there's Susan, there's Sarah.

[Gary Vaynerchuk]

Right?

[Elvis Duran]

I know unlimited 40 to 50 year olds that are lazy and have no drive. And I have tons of 20, 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.

Talk 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.

I 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 a 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. Let'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 because they lack patience. Wow. Uh huh. That's the punchline, my friend. Like if you like, do what you.

[Gary Vaynerchuk]

How old are you?

[Elvis Duran]

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.

No, I feel better. No, no, These are the days. Winston Churchill, my favorite quote. These are the days.

And that's the punchline. If, if 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.

[Gary Vaynerchuk]

40'S old.

[Elvis Duran]

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. You know, we're gonna live much longer. We're gonna live into our 90s, hundreds. Like we have so much time.

I'm 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. You're doing too much of that stuff and you can work a 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. Patience is something we do not talk about.

[Narrator]

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. And so in our society, we're being told that the faster you do something, the better you are. The more.

[Elvis Duran]

That'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.

Then who do we listen to?

Yourself. Yourself.

Listen to yourself.

Now, the problem is a lot of us don't like what ourselves are telling people.

Right? The inner voice can be a worse enemy.

That's right.

[Gary Vaynerchuk]

So.

[Elvis Duran]

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.

[Narrator]

It's not like, it's too scary. I don't wanna do it.

[Elvis Duran]

That's right. And you have to taste things. I love when people are like, oh, I hate sushi. I'm like, have you had it?

[Gary Vaynerchuk]

They're like, no, that's me.

[Elvis Duran]

I don't wanna taste it.

[Gary Vaynerchuk]

Right?

And so to me, that's the most.

[Elvis Duran]

Fun, 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 and 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.

[Narrator]

I wish I think about that, how different life actually feels at 50 compared to what you thought when you were 25. Let'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.

[Gary Vaynerchuk]

Hey guys, it's Gary and I've got 50 seconds for you.

[Elvis Duran]

This is 50 seconds for every 50.

[Gary Vaynerchuk]

Year old in the world. I need you to understand something. You have so much time. I'm in entrepreneur land and I meet.

With all these kids, show these kids.

[Elvis Duran]

Show these kids, all these kids.

[Gary Vaynerchuk]

And they're taking advantage of the new world, right?

[Elvis Duran]

But they're young and they're raw and they've got a lot of of great and some of them are great and.

[Gary Vaynerchuk]

They'Ll be all time great.

[Elvis Duran]

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.

[Gary Vaynerchuk]

I didn't grow up with this shit.

[Elvis Duran]

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.

[Gary Vaynerchuk]

And with the health trends and the.

[Elvis Duran]

Way the world is now, you've got.

[Gary Vaynerchuk]

A long life in front of you.

[Elvis Duran]

So instead of sitting in that job for the next 10 years, go do your thing.

[Gary Vaynerchuk]

You've got plenty and plenty of time.

[Elvis Duran]

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.

[Gary Vaynerchuk]

Fuck are you talking about?

[Elvis Duran]

Here's what I'm talking about. You have 30 remarkable fucking years of execution in front of you. We 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.

[Gary Vaynerchuk]

Have not accomplished, how you fucked up.

[Elvis Duran]

That marriage, took that wrong job, went.

[Gary Vaynerchuk]

To the wrong school, please step up.

[Elvis Duran]

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?

[Narrator]

So hopefully now you see it, time isn't your problem. Your mindset is at 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.

[Elvis Duran]

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. If you want it so bad, if it's in you, like, you know, maybe it's not time to take up golf or you know, pack it in. Maybe it's time to actually triple down and really focus on your 7pm to 2 in the morning. There's so many people that truly are good entrepreneurs or have entrepreneurial DNA, but they just weren't lucky enough to be born during an era that, that seemed practical. Like it's just so like it's hard for somebody who's for 30 years gone a certain blueprint to understand that this is that realistic and they feel like it's a young man's sport and it's just not. Like, it's just not. It's, you know, if you got the right DNA and you're a 72 year old female, you have just as good of a bat as a 27 year old dude. But you've been trained and story told to and positioned and lived in a 50 year matter that doesn't feel like this thing in here is a practical way to build that, but it is. Entrepreneurship is not predicated on taking away from your family. Entrepreneurship is from taking away from everything else. So stop making excuses.

[Gary Vaynerchuk]

Oh, these millennial kids are so entitled.

[Elvis Duran]

Oh, these kids didn't have to work as hard as we did. Nobody Cares if you're 40, 70, 90 alien, female, male, minority. The market will accept your victories if you're good enough to have a victory. And I believe more than ever that if you're a 49 year old housewife with two kids because of this phone, you've got more opportunities to create something for yourselves. Please, my friends, do not allow just the 18 and 14 and 22 year olds to grab at this pie that.

[Gary Vaynerchuk]

Is so available to all of us.

[Elvis Duran]

Regardless of our age. We're gonna live longer. The opportunity is real. The 58 year old right now that's watching this, you're gonna live another 40 years. 40 years of being able to do something you love is a big deal. Start putting in the work. Start recognizing this isn't just a young person's game. Start, represent, start representing the people that actually put in the work. The gray hairs, that context, that knowledge. Start deploying that educate yourself on the new world. Yes. You didn't grow up with Instagram, you didn't grow up driving and you learned that. Stop making excuses. Start getting educated in the actual world and start opening up the opportunities. In my true opinion, you are actually more likely to be successful in building a company at 45, 50 today than the 18 year olds that are coming out. Because there's a naivete, a lack of experience. You have experience, you have experience, like that's a real thing, like cool, like youth and excitement is great. You have actual business experience.

[Gary Vaynerchuk]

There's a plenty amount of talent.

[Elvis Duran]

There's plenty amount of talent and there's a ton of fire and bravado and there's a confidence, there's a confidence that youth provides. But the difference between me and so many of you is I've put in the goddamn work to learn where people's attention now is. And I'm deploying myself through there. Many of you have drawn a line in the sand and say, I'm not downloading Snapchat, I'm not downloading Instagram. And that, my friends, is going to allow you to lose. This video is made for one reason.

[Gary Vaynerchuk]

I want it to be the calling.

[Elvis Duran]

Card, the seed of the explosion of the 40 to 80 year old entrepreneur in our society. The fire I see in the eyes of a 19, 20, 25 year old that feels that they're entitled to this. And then on the flip side, the diminishing, just a little bit of ashes with a little smoke left of that same entrepreneur when they were 22, at 46, when practicality and family dynamics and the history and the market tearing down and the lack of that same opportunity has just windled down to a moment where they don't believe that they've got that shot. And I'm here to tell you, you absolutely do. I mean, there are absolutely a ton of entrepreneurs that started their companies in their 40s, 50s, 60s and 70s when it was difficult to do such a thing. Sidi Frank, who created Grey Goose, didn't invent his big thing until the 70s. And so I'm desperate, I'm desperate to give you the springboard to say, you know what, instead of watching House of Card Seasons, instead of trying to, you know, go to ball games or things of that nature. Yeah, I do have 7pm till 2 in the morning, Monday through Friday. Heck, for a lot of you, the kids are out of the house. Let's get into the practicality for the late 40s, 50s, 60 year olds that are watching this right now, the kids are out of the house. Like, yeah, you could pick up golf or you could finally start that candle company because you put pretty pictures of candles on Instagram and it happens. Learn the craft. Figure out the opportunity at hand. Go attack it. You only live once when you're 90 to 100 years old and you're regretting that you never built this business and you let this era pass, this moment where there's so much entrepreneurial upside, you'll regret it. And regret is the worst. I mean, that's what it is, at least the way I see it. Like I got home at midnight last night and every fucking night. Like, it's just real. Like, just man, I don't have to. So I don't know. I think there's a real, there's a real opportunity to, to inspire a generation that so deserves it. Like, I almost feel like that's being 40. I feel like I'm caught right in the middle. Like, I have so much empathy for. I recognize how insane I had to be to like, I mean, you can, I can't even imagine how not practical being an entrepreneur was when I was your guys, like when I was half your age, like in school, like a 15 year old now in school that's getting D's but is like selling shit on the Internet. Everyone's like, oh, there's our next. You're the next Mark Zuckerberg. Mine was like, yo, you're the next piece of shit. You know, like, it's so insanely different. And so I have a lot of empathy for people that I don't know if they recognize how real it is.