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Jesse Itzler

Jesse Itzler

American entrepreneur and author

Sep 21, 2026

12:38
What are your thoughts on that?
12:41
I think that it depends on who you are and where you are and how old you are.
12:47
I think the advice I would give to a 20-year-old about grinding is different than the advice I would give to a 50-year-old that's starting out as an entrepreneur.
12:55
It depends on where you are in your journey and who you are.
12:58
So for my dad, my dad was a perfect example of how simple can be exceptional.
13:05
So he didn't grind.
13:06
He didn't go through all that.

5 MINS LATER

18:23
It has
12:55
[laughs]
12:56
"You remember Christina Aguilera's story?" I'm like, "That was me.
12:59
Can I see you on Friday?" Friday comes, we go and we have the meeting, and it lasted about 12 minutes, and the CEO, Rich Santulli, said, literally threw us out.
13:10
This is a direct quote, and it really pissed me off.
13:12
He said, "If you think I'm giving two guys who probably didn't break 1,000 on their SAT," which really pissed me off.
13:17
I got a 980 on my SAT, so that really bothered me.
13:20
[laughs] He's like, "That's never happening." He threw us out.

15 MINS LATER

28:09
You won't, you won't have the ability to pick up all the opportunities.
93:01
Yeah.
93:01
And I heard about this conference called TED in Monterey, California when they were first starting out that was attracting all these tech guys and well-off folks, et cetera.
93:10
So my partner's like, "You gotta go to the TED Conference in Monterey, California." So I ha- I think I connected through Chicago into LA.
93:17
It's a five-hour car ride to Monterey, California.

6 MINS LATER

99:22
Yeah.
99:22
But you touched on something I think is important to the listeners, and m- to me, I have a lot of different definitions.
99:28
Success isn't being good in one bucket.
99:31
It's not about, like, I made all this money.
58:35
Okay.
58:35
So we offered the ability to attract much younger athletes, entertainers that we said, "Look, if these guys are introduced to your fleet, they're gonna be customers for the next 50 years.
58:46
And think about the lifetime value of that customer.
58:50
Give us a shot.
58:51
If it doesn't work, there's not, like, no harm, no foul." And they said, "You know what? We'll give you guys a shot." And we-

11 MINS LATER

69:31
Yeah.
69:31
But you touched on something I think is important to the listeners, and m- to me, I have a lot of different definitions.
69:37
Success isn't being good in one bucket.
12:05
So, so we scheduled things by family-
12:07
family-... our family time, our time in Colorado, that's our, that's our time together out in Colorado.
12:13
We have a, a log home out there we love.
12:15
Um, holidays, birthdays, and then work.
12:18
And so I'm gonna hand this over to my staff and let them fill in the rest of this calendar, but this is the first time that we've ever done this, and when I, when, when I talk about what an impact you've made on our lives, I mean, you, you really have.
12:29
My wife loves this idea.
12:31
I love this idea.

41 MINS LATER

53:33
Like [chuckles] yeah.
5:53
Okay.
5:53
You know? And let me just preface that by saying that, like I'm 57.
5:58
As you get older, and maybe you found this too, it's really hard to create newness.
6:03
Like, where the hell does newness come from? You have to, like, schedule it.
6:06
You know, it doesn't just happen.
6:08
So I've been doing these three things, and they've really helped me.
6:11
So the first one is called...

28 MINS LATER

33:48
... you're, you're balancing your debts or you're, you're canceling out your debts or whatever.
43:07
[laughs]
43:07
He told me all this shit.
43:09
But one thing he said, he was like, "I spend three hours a day cumulatively for myself." And I was like, "Three hours? Who could do that? What are you talking about? What do you mean? What does that look like?" He's like, "Well, you know, like, I wake up and I spend about 30 minutes just reading the paper.
43:23
I take a sauna every day for about 30 minutes.
43:25
I'll go for, like, a walk for an hour, and I usually read.
43:28
So cumulatively, I try to have three hours a day." And I was like, "What is..." He's like...
43:34
I'm like, "Why?" He's like, "I show up better at work.

8 MINS LATER

51:38
Yeah.

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