March 1, 2026
991. Whether You're Young At Heart or Young In Age-Stop Waiting.
Send a text Episode 991 is a punch-in-the-mouth reminder that sometimes the safest thing you can do… is go for it. In this episode, I share a note Steve Jobs emailed to himself before his Stanford commencement speech — back when he and Steve Wozniak were just two guys with no wives, no kids, no house payments, and nothing to lose. They weren’t investing in better apartments or fatter bank accounts. They were investing in themselves. And that’s the heartbeat of this episode. If you’re young — ...
Episode 991 is a punch-in-the-mouth reminder that sometimes the safest thing you can do… is go for it.
In this episode, I share a note Steve Jobs emailed to himself before his Stanford commencement speech — back when he and Steve Wozniak were just two guys with no wives, no kids, no house payments, and nothing to lose. They weren’t investing in better apartments or fatter bank accounts. They were investing in themselves.
And that’s the heartbeat of this episode.
If you’re young — I’m talking high school, college, early career — this is your season to explore. You can take the hit. You can start over. You can move cities. You can try something and hate it. You can fail and regroup. The walls haven’t closed in yet. So don’t build them yourself.
If you’ve got some miles on you — like me — this message is just as important. Because now you’ve got something young people don’t: wisdom. Experience. Knowledge. Judgment. And that can either become fuel… or it can become fear.
In this episode, I talk about:
- Why “nothing to lose” is often when you have everything to gain
- The difference between reckless and playful risk
- One-way doors vs. two-way doors (most decisions aren’t permanent)
- Why starting with free is powerful
- How writing and starting this podcast at 43 changed my entire trajectory
- And why succeeding at not trying is the quietest failure of all
This isn’t about burning your life down.
It’s about pushing the walls out before they close in.
It’s about remembering that you can always start over. I’ve been bankrupt. I’ve been homeless. I’ve been demoted. And I’m still here. Still building. Still young at heart.
Sometimes when you have nothing to lose… You have everything to gain.
If there’s something pulling at you — something you know you need to explore — this episode is your nudge.
Let’s go.
Always keep it simple.
Keep it moving.
Never settle.
Stay tough.
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Keep it simple. Keep it moving. Never settle. Stay tough.
WEBVTT
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All right.
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3, 2, 1. Let's get it.
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For those of you who are watching on video, I'm a little off center in the, uh, camera angle because the sun is trying to come through the blinds there and makes me look, I'm already pale.
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It makes me look even more pale.
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So if you happen to see this on video and you're like, he's not squared up in the frame, that's the reason being.
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Welcome to another episode, episode 9 91.
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Of what's your problem?
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The podcast.
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And I wanna read to you, this is something, man, I just, I came back to, I read it yesterday.
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I wrote it down like, golly, that's powerful.
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And I read something else this morning, but I kept coming back to this.
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So this comes from the book, make something Wonderful.
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And this is from the Steve Jobs archive and uh, Steve Jobs's wife.
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Created the book.
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And this is like notes to himself and notes that he left behind and she archived it.
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It's a, it's a free book.
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Like you can, you can go to steve jobs archive.com and get the free book.
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Uh, I wish it was in a format where I could highlight it because there's so many good parts to it.
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Um, but hey, it's, it's free.
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So let me read to you something.
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Like I said, I just kept coming back to, and this Steve Jobs was he, he would send emails to himself and I think that's, I think that's really interesting is like when he would have thoughts, instead of writing them down, he would just email himself and, you know, write it like he would write anything else.
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55 PM.
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He sent himself an email and for context, he was kind of sloshing around.
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The idea of what he wanted to share at the Stanford commencement speech and that Stanford commencement speech is, I mean, millions have have heard it now, but this was the time where he didn't, he didn't really like giving public speech, uh, speech speeches or anything like that, but he was just kind of, he, he wanted to, to be impactful.
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And so let me read to you what he, what he sent to himself.
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He said, when my partner, Steve Wise in the act and I started Apple, most of our friends and family told us that we were, nuts wise, had a great job designing handheld computers, uh, handheld calculators at Hewlett Packard, and I had a fun job designing games at Atari.
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See, they were comfortable.
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Life was good.
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Steve Jobs is designing games at Atari.
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Sounds pretty fun, right?
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In his wheelhouse wise, who was, you know, the engineering mindset, he was designing handheld calculators right in his lane.
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They were comfortable.
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Now this is what he continues on, he said, and you know, wise at HP and Steve Jobs at Atari.
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He said they were giving them up to start this company, to make primitive computer, to make a primitive computer on a PC board that only a handful of hobbyists, mostly who are our friends, they may buy it for less than it costs us to make.
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In other words, we're gonna leave a SurePay job.
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We're gonna start this company, we're gonna start a computer company.
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We're gonna make these keyboards and all the labor, all the parts, everything we put into it for what we sell 'em for, and mostly to our friends.
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We're gonna lose money doing it.
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I mean, what happens after you sell all your friends, then what?
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And he said, I remember talking to Wise and said, this is so good.
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We may fail, but we have.
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Right now we have no responsibility.
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We have no wives.
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We have no kids.
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We have no house payments.
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We have nothing.
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If we don't do this now, we never will.
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We have nothing to lose, and the worst we'll get out of this, the absolute worst we'll get out of this is that we'll have memories.
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Of having gone for it to give ourselves the experience of participating in what Bill Hewlett and Dave Packard did when they started hp.
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You can't, you can't put words to that.
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And he said, so rather than invest in better cars, better pay, uh, better, uh, apartments are fattening up our bank accounts.
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We decided to invest in ourselves.
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Oh my God, bro, you could, you could just stop right there.
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They went for it all.
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And the thing that just kept resonating to me, and I've said it before, sometimes when you have nothing to lose, is when you have everything to gain.
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And this is a, this is a, an important message.
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For younger people, and I say young people like my daughter, she's about to graduate high school.
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And when you graduate high school, it's super scary, man, because it's like, okay, do I just follow the herd?
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Do I do what everybody else is doing?
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Right?
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And so.
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You're, you're, you're, you're, you're crossing the chasm, you're crossing the door.
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The, the doors, you're, you're crossing the threshold, I should say, of becoming an adult.
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And the impression I want to give to her and I want to give to other people, young people, is, bro, just go for it.
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Go for it.
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When you have.
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So little responsibility.
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The number, the only responsible thing you have is to yourself, and so you can always start over.
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You can always start again.
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You can always come home and regroup and go back at it again, especially when you're young, man, because I can tell you this, as a 53-year-old man.
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You're never going to, if you don't to, to Steve Jobs's point.
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If you don't go for it now, you never will.
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And I'm not saying do this in a reckless kind of way, but I'm saying the responsibility you have to yourself, you can always go back to school.
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If you don't wanna go to school, don't do what everybody else is necessarily doing.
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If that's not the thing that just pulls at you, then damn it, go try something.
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If it, if you want to travel abroad, go do it.
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Figure it out.
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Stop putting these future timeline.
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Well, I mean this.
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No, because as you get older, the responsibilities and the walls of responsibilities and the walls of caution close in.
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I'm telling you, I started selling cars when I was 25 years old, and I'm telling you, in a blinking of an, uh, of an eye, it's 28 years later, it is.
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So if you're young, if you're younger, like take stock in your response.
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Like if, if you wanna move to a different city, remember though, going to a different city is not going to make everything all right for you.
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Okay?
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Because if you're not changing in here and you're not changing in inside of you, then you're just going to be at a different zip code with the same bullshit that you carried with you.
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You're gonna attract the same things.
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You're gonna think the same way.
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Like you're gonna have to do everything different if you're gonna do that.
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But hell try.
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You gotta figure these things out.
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You gotta, you gotta explore.
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There's, there's, there's a big world out there.
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I told my daughter this like, look, there's a whole lot bigger world out there than right here where you grew up.
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As a matter of fact, I don't even want you to stay here.
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I want you to get out there, go experience.
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You can always come home and regroup if you need be.
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Okay.
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So that's the message for younger people that I want to stress, like go back and read.
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What he said, like right now we have no responsibilities.
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Like we might as well just go for it.
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That's for young people, but also for, for people.
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You may have some age on you.
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You may have some miles on you, but bro, you're young at heart and lemme tell you where you're young at heart, you're frustrated right now because you're at a point in your life, you're like, there's gotta be more to this than just this.
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Then, then hitting the old Capital One bill and making a house payment and driving a car.
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And I get the fact that you have responsibilities, but shouldn't the number one responsibility be to yourself?
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And again, I'm not saying be reckless, but I'm saying you have that internal pull at you.
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There's something you want to do.
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There's something more.
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Well begin to explore those things.
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And because if, if, if you're not checking yourself, if you're not pushing these walls out, these walls are quickly gonna close in on you and then you just, oh, well man, I wish I was younger.
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I wish I was about 10 years younger.
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I mean, everybody says that, like you could still be young at heart.
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And there are things that you can begin to play with.
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Like stop trying to hit the money shot on everything.
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Stop worrying about looking embarrassed because you look a little foolish at times, like, why are you even worried about?
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Don't even worry about that.
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I'm in a unique advantage.
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I've been bankrupt, I've been homeless, I've been demoted.
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So it's an advantage for me because it is.
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I have most people fear those things.
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I've experienced it, and so it's an advantage because I already know what that's like.
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I've had to start over many times.
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I lived in a house with no refrigerator, no stove.
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I. And figured it out.
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Just me and my 5-year-old son way back in the days, and that's when I ventured out and started selling cars.
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I was like, well, lemme just try this again.
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I mean, I was, I was Mr. Screw up.
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I was the only one in the family.
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I was the only, I was the only kid in the family that got a scholarship full ride.
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Yet I'm the only one who didn't finish college.
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So here we are, March again.
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He's gonna go sell cars, screw up.
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Family constantly bailing me out.
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And finally they were like, we can't bail you out anymore.
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You're on your own.
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Best thing that happened for me.
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Okay.
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So I just went out there and started trying it.
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28 years later, I'm still doing it.
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But you don't, you, you won't experience you.
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You won't find these things in life if you don't try it.
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I mean, worst case scenario, I could have went back to the casino.
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Or a casino and started over.
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I was only making two grand a month, $2,300 a month before taxes.
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I mean, I could find a job for two grand a month.
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I could always start over.
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Let me tell you the advantage that you have.
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If you got a little, if you got a few miles on you, if you're older, because, bro, I can't tell you how many people I talk to and be like, man, the things you regret, the things that you're frustrated about is, is, is because you wish you would've done some things?
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Who says you can't?
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Now you, you wish you were to.
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Well, you can't get the time back, but you can do something with the time you have left.
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And again, I'm not saying be reckless, but I am saying, bro, you need to get out there and play a little bit.
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There are some things inside of you that you're still young at heart on, and if you're not, that should scare the shit out of you, but you're still young at heart right now.
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I want you to experience those things.
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Back in 2017 when I started the podcast.
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I, I hadn't.
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I was like, well, fuck it.
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I'm demoted.
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Um, I'm broke.
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I do have a message.
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I do love to read.
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I do love to share.
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I love to communicate.
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I love to teach.
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All right.
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Started with free, started the podcast, bro.
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What it has done, and I'm not ready to speak on it yet, what it has done here in the next six months is going to be mind blowing.
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It has set me up.
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I had no idea where this is going.
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It has set me up in a way that it's, it's everything I've been praying for yet didn't see how it was gonna happen, and I believe it just happened.
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Speak more on it when it actually, it's already, the seeds are, the conversations are already being started.
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Let's see where it goes.
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But see if, if I wasn't trying something, even though I was whatever, I was 43 years old at the time when I busted out, what was that?
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44? Busted out starting over again.
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I could have very easily been like, oh, well, let me just sell cars.
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No.
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I was like, well, fuck it.
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Sometimes when you have nothing to lose, you have everything to gain.
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Look, I would rather remember this.
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I would rather try.
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And fail, then succeed at not trying.
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And I told my wife this, like my wife is younger than me and she's, she's just moved into a bigger gym.
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Big, bigger gym, bigger expenses.
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I'm like, bro, look like, what's the worst that could happen?
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You're young.
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You could start over.
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You got a master's degree?
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Fuck it.
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Let's go.
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She keeps me young.
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I keep her, I keep her older.
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The, the, the, the advantage that you have as a, as an older person is you have wisdom.
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And what is wisdom?
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Wisdom is composed of three things.
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It's experience.
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You got that?
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It's knowledge, which is acquired skills got your hands dirty.
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Okay?
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Not only theoretical.
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Knowledge, but practical knowledge too.
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And then it's good judgment.
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Good judgment is not necessarily saying, oh, I'm older, taking stock of your age saying, oh, I'm older.
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I I shouldn't do this Now.
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I've got a lot to lose.
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I could lose my house.
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Okay, can you keep playing the game?
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You get the, the, the, the task is, can I, you make decisions that stretch you, that push you, yet don't.
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You know, I'm, I'm not saying you make decisions and your kids and you end up out on the streets.
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No, but sometimes the good judgment that we think that we're making, we're taking stock in our age and we're saying, no, no.
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Oh, well it's passed me by.
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Is there something you can do?
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Can you begin playing in the outer bands?
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I mean, you start with free.
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Like I, like I said, I started the pie.
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It was free.
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It didn't cost anything.
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I'm right here in my office, in my house.
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I started with a cell phone and I sat in my closet with a legal pad.
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Same thing I do today, but that's where I started.
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And you just never know.
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But see, that is the thing that has brought me energy.
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That is the thing that writing literally saved my life.
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That is the thing.
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Where I developed the five skills, communication, curiosity, creativity, continuous learning and action and productive confrontation.
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It was putting in the reps and I was like, oh.
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The same skills you, you learn in sales, you could, you could take into life the five Fs, your faith, your family, your fitness, your finances, your fulfillment, both professional and creative.
00:16:48.794 --> 00:16:49.995
I didn't read that anywhere.
00:16:49.995 --> 00:16:55.245
It came up after thousands of hours of writing.
00:16:56.563 --> 00:16:58.154
That's a full bodied life.
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I have those five areas and those five skills.
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See what I'm talking about?
00:17:06.315 --> 00:17:08.085
And bro, I'm just getting started.
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I'm 53, but I'm still young at heart.
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I got a lot left in the tank and I get to experience it every single day.
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And I want you to experience that too.
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That's the thing, man.
00:17:18.630 --> 00:17:20.339
Yeah, that's the thing.
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And so the good judgment, lemme come back to that thought is not being cautious.
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Or my age woman says, who says who?
00:17:28.559 --> 00:17:30.119
This is your only go around.
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Can you, can you do something?
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And even, even if you take a hit, don't let it wipe you out.
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The, the, the game is to keep playing the game.
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You don't go all chips in, but you put a few chips in, okay?
00:17:42.029 --> 00:17:43.259
And you start playing these things.
00:17:44.220 --> 00:17:53.909
And so the good judgment is if I begin to wade into these waters a little bit, is it a one-way door or a two-way door?
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One-way doors.
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Jeff Bezos talks about this one-way doors are you cross that you can't come back.
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But most of the things we have in life, most of the, the decisions that we make in life, they're two-way doors.
00:18:06.599 --> 00:18:06.869
Okay.
00:18:06.869 --> 00:18:07.980
May be a little embarrassing.
00:18:07.980 --> 00:18:09.809
You may have to kind of take a step back.
00:18:09.809 --> 00:18:13.289
In other words, I left the position and then, oh, that didn't work.
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Had to come back.
00:18:14.069 --> 00:18:15.569
Well, I don't get my old position back.
00:18:15.839 --> 00:18:17.160
Maybe I have to start behind that.
00:18:17.160 --> 00:18:18.240
Still have experience.
00:18:19.019 --> 00:18:20.309
Maybe that was the best thing to happen.
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Maybe something else.
00:00:00.689 --> 00:00:01.020
All right.
00:00:01.020 --> 00:00:02.129
3, 2, 1. Let's get it.
00:00:02.279 --> 00:00:15.929
For those of you who are watching on video, I'm a little off center in the, uh, camera angle because the sun is trying to come through the blinds there and makes me look, I'm already pale.
00:00:16.530 --> 00:00:18.300
It makes me look even more pale.
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So if you happen to see this on video and you're like, he's not squared up in the frame, that's the reason being.
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Welcome to another episode, episode 9 91.
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Of what's your problem?
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The podcast.
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And I wanna read to you, this is something, man, I just, I came back to, I read it yesterday.
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I wrote it down like, golly, that's powerful.
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And I read something else this morning, but I kept coming back to this.
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So this comes from the book, make something Wonderful.
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And this is from the Steve Jobs archive and uh, Steve Jobs's wife.
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Created the book.
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And this is like notes to himself and notes that he left behind and she archived it.
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It's a, it's a free book.
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Like you can, you can go to steve jobs archive.com and get the free book.
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Uh, I wish it was in a format where I could highlight it because there's so many good parts to it.
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Um, but hey, it's, it's free.
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So let me read to you something.
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Like I said, I just kept coming back to, and this Steve Jobs was he, he would send emails to himself and I think that's, I think that's really interesting is like when he would have thoughts, instead of writing them down, he would just email himself and, you know, write it like he would write anything else.
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