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Jesse Itzler

Jesse Itzler

American entrepreneur and author

Oct 29, 2026

speaker_1NARRATOR
0:44
Itzer's new book is called Living with a Seal, 31 Days, Training with the Toughest Man on the Planet.
0:50
We all have a reserve tank, and I found out that I had so much more in my reserve tank.
0:54
Like, my baseline was here, and he taught me that it really should be up here.
0:59
He said, if you're crazy enough to ask a guy like me to come live with you, mother, I'm crazy enough to come.
1:07
If I'm under-indexing by 100 pull-ups, if I'm leaving 100 pull-ups on the table, what are the areas of my life am I under-indexing
speaker_2HOST
1:24
When you
1:25
were up there, was there any time where you're like, what am I doing? Like one minute into it.
1:32
It's all about getting comfortable being uncomfortable.
26:51
Yeah, there it
26:51
is.
26:52
And I color coordinate things and it's super duper helpful.
26:57
So I've been doing that for a while.
26:58
People's like, how do you plan? I'm like, this is how I plan.
27:02
And I launched this calendar and it's changed a lot of people's lives.
27:05
The Misogi that you talked about is part of the calendar because having a calendar is one thing, but how you use it and fill it out is another.

13 MINS LATER

40:23
Why do you do that?
10:36
So you and your wife balancing four kids, what does that look like?
10:40
So, you know, as you get older, I think it's really hard to create newness.
10:45
Most of us start to live life in routine, and when you live life in routine, life goes really fast, and you cruise through life.
10:55
So you have to work hard at creating newness.
10:59
You have to plan it.
11:01
And if you don't plan it, usually it doesn't happen.
11:04
So I'm really aggressive with my planning.

26 MINS LATER

36:48
Is that intentional? Is that intuitive? Is that key to your entrepreneurial journey?
86:29
Yeah.
86:29
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.
86:38
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.
86:45
It's a five-hour car ride to Monterey, California.

6 MINS LATER

92:50
Yeah.
92:50
But you touched on something I think is important to the listeners.
92:53
And m- to me, I have a lot of different definitions.
92:57
Success isn't being good in one bucket.
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.
13:59
Will you back up to the advice that Lou Katz gave you when you were offered to sell a 10% interest in your 10% annuity in your jingle business for 10,000 bucks way back when?
14:12
Well, actually, it was 10% of all my future earnings.
14:15
Yeah, I was sleeping on – between the ages of 19 to 23, I was flip-flopping amongst 18 different friends' couches.
14:23
And when I was on couch number 17, someone had offered me – I was in the jingle business.
14:30
My business model was go in a studio on my own nickel.
14:34
write a song for like the New York Yankees.
14:36
I was doing it for sports teams mostly.
15:36
And he erupted.
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.
21:38
for a great year.
21:39
You're planning it.
21:39
Right.
21:40
I can have a good year.
21:42
Maybe a couple of people invite me on a great trip.
21:44
I get someone says, oh, you want to go to the Super Bowl? That's amazing.
21:48
I can sit down and say, what's gonna light me up that I'm so excited about this year that like I wake up and I have no pressure.

7 MINS LATER

28:46
So I guess like, is it hard for you too? And also like, how do you get better at that?
24:56
And I
24:56
think that, you know, people, everybody's wired differently.
24:59
And my wife went a mile deep into Spanx.
25:02
Her company was called Spanx.
25:04
And that's all she did for 20 years.
25:06
I mean, she had blinders on and she was really good at saying no.
25:09
You know, distraction is probably the number one enemy to everybody listening to this podcast.
28:20
or they're more they're
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.
2:06
memory coach.
2:09
Because I wanted to get better at memorizing names.
2:11
I wasn't great when I met people at remembering their names.
2:13
So I brought a coach in to help me with that.
2:16
I've had sales coaches.
2:17
I've had coaches in so many areas of my life.
2:20
Because I'm not great at everything.
speaker_0ADVERTISER
3:49
not.
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.
33:52
So kind of take me down that road of what brought you from there to here.
33:57
Yeah, I had a really unconventional journey as an entrepreneur.
34:01
I started out in the music business.
34:03
I was signed to a record label called Delicious Vinyl back in the early 90s.
34:07
Got dropped from the label.
34:09
I love sports and music, so I moved back to New York.
34:12
And I went to the Knicks with an idea for a theme song called Go New York Go that they could play in the arena during timeouts.

19 MINS LATER

52:49
But I'm surprised you sleep that much.

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