24hrs With The Happiest Billionaire, Jesse Itzler

That is un-friggin-believable. That made me cry.

This is Jesse Itzler, and he's got the craziest resume you've ever seen. He sold a private jet company to Warren Buffett, he helped build Zico coconut water, and he's the only guy who can say that 50 Cent was his intern. But I don't admire Jesse just because he's rich financially. I admire him because he leads such a rich life. He runs these crazy endurance races, he goes on adventures with his friends, and I've always wondered how How does one guy do so much? As Jesse says, we don't lack time, we lack a system. So that's why I'm here at his house today to learn the exact system that he uses to plan his year. All right, we're here to do an annual planning session with the one and only Jesse Itzler. They always tell you to think like a billionaire. Well, I came to a billionaire's house to see how he thinks about planning his year.

There he is. Welcome to the house, man. Jesse, what's going on, man?

Last year you came on the podcast and you were like, here's how you do it. This is what you do. I was so inspired and I left and I did 25% of the process. So this year my forcing function was, I'm coming to his house. I'm going to do it with him.

That's the—

because, you know, I'm a procrastinator.

Yeah.

So I was like, oh, I got the whole year to plan this. Yeah. And then come the whole year, I still didn't do all of the steps. And so this year I'm going into the year with more momentum.

A year is a long time.

Yeah.

You're not going to sit down and be like, oh, here's all 365 days and I'm going to do it in two. It doesn't work like that. To figure out like, what do you want to put your energy into this year? And then once you get that, but I'll give you the whole thing. Anyway, welcome. You want a quick tour? Clean page, pristine blank slate, dream, plot and scheme sharper than a laser beam. 12 months to canvas, I'm the Van Gogh of goals. Paint strokes bold, no half. These are organic avocados. Have you ever seen anything that an avocado is supposed to look like? You can bring that home with you. So like my sneakers, never untied. No time to sideline, let the vision ride. Fresh kicks, new tricks, write the script, don't miss. It's all in the mix. New Year, who dis?

I'm the architect of bliss. Every step This is Taylor.

This is Taylor. Hello, Courtney. Courtney, what's in that smoothie?

Cocoa powder, a chocolate Truvia protein powder, bananas, flaxseed. Courtney, how good is— how good is this avocado gonna be when I try this avocado? This is real. Blow your mind.

So this doesn't look like it's anything special. We're big on family dinners, so like, you know, we have a ton of family dinners, but every night that we have a guest. All the kids at the table have to ask the guest at least one question. What's great about that is it makes the kids inquisitive. It teaches them a little bit about public speaking, you know, and looking eye contact. We coach them through a little bit of that stuff. In today's world, you know, where there's so much of this, getting them to talk and communicate and be curious, like where'd curiosity go?

Right.

You know, like Where's curiosity? Seriously. You know what the best thing my parents did for me when I was a kid? They didn't overschedule me. They let me be bored. I used to go with my mom to— she was on the Board of Education. She'd have 3-hour meetings once a month, and I would go there. She would give me a box of crayons and paper, and I'd be so bored. But then I'd dream about being on the Knicks. I'd dream about being an astronaut. I'd think about, like, a girl in the class or whatever, and like, It just got my creative juices rolling, and it also taught me to be patient, self-soothe, you know, all the things that have been stripped from kids. This is a very meaningful room for us.

We're about to walk on a sky bridge. I don't know what to call this. This is amazing. Can I sponsor— can this be the My First Million Sky Bridge? We get like a sticker on the bottom. Absolutely.

Oh, I'm excited about this. I, I know you're anxious to get started. I think before I think before we start and do anything, like anything in life, we gotta get into the right mind state, and we can't like, you don't wanna come, you just got off a plane, you're tired, I think we gotta get, and this goes for anybody, by the way, you wanna like plan, or you wanna have a meeting with your significant other or partner, or even by yourself, like, you gotta get excited about it and ready to do it and be in the right mind, so what I love to do is just take you through what I do in the morning, which is just quick little workout, I do this quick little workout, maybe jump in the sauna, but then we'll come back here, you'll feel great.

Perfect. Let's do it.

Good. Yeah, let's do it. I don't have a lot of time like you. Like, I used to say like, oh, I need an hour to work out. I saw this thing on Instagram that's like 12, uh, 10 motions that everybody should do, and I put it on my wall. It's like basically 10 exercises. By the way, I don't even know if I'm doing all this shit right, but I just—

you're doing it.

I'm doing it and it feels good and it takes me like 6 minutes and I'm like, every part of my body is getting work.

Yeah, I call this the no excuses. If you don't have 6 minutes, you don't have a life.

The only thing is I got a bad foot. Getting an extra I think I broke my foot. I'm not even kidding. Let's go to the sauna. You good, Sean?

I'm good.

Oh, it's a good sign. See the smoke? That means we're cooking up. That means we're cooking up. Yeah, come on in. So you want to hear something crazy? So this is, this is, you know, water, but this is 50% beer and 50% water, and it creates You get a buzz too? I'm a big believer in learning from the masters, you know? Like, I had Goggins live with me, master of mindset. I live with the monks, masters of spirituality. I live with Wim Hof, the master of cold, the master of, you know, cold and breath. And I went to Finland, the masters of the sauna. I spent— I did a tour of— a 10-day tour of 30 different saunas. And one of the gals that was leading one of the sessions suggested that we use beer. So I was like, "Alright, the master said beer, we use beer." That's why I'm here.

The masters of planning your year. No, planning your year. That's why I wanted to come to you. So the reason I wanted to come out here, because I don't travel much, I got little kids at home, I try not to travel, but the reason this was like a no-brainer for me was because I wrote this blog post a while back called Who is Your Elon? So I live in San Francisco, and in San Francisco, Elon is like the kind of North Star everybody chases. Do something really big, really impactful, really ambitious, really challenging. You know, he'll be the first— world's first trillionaire. And that's amazing. I love Elon. I love that he exists, but I don't want to be Elon. And so it would be foolish for me to choose that as kind of a North Star or a blueprint to follow because I don't want to be divorced 3 times and kids, and you know, like, there's all these other parts of that picture that I don't love. So I was like, I thought about that, and I was like, what is like the blueprint that I like? Where are examples that I can model? So they got success in their career, but they also have success at home, and they're healthy. You know, you're running marathons and whatnot, you're, you're super fit. And then it's, um, and then, you know, adventure, friendships and adventure. And like, I don't have all of that laid out So I kind of wanted to meet somebody who's, you know, further ahead in that game, who lives that version of the good life. For me, winning is winning in all those areas, having my cake and eating it too, with my friends and family, with a big-ass fork. That's kind of what I wanted to do. How do I assemble this life that has all those components, rich in all those areas, not just rich financially?

Yeah, no, I love that. And, you know, you mentioned Clues. First of all, thank you for choosing me.

Sorry to flatter you in the sauna here.

No, I love that. But you mentioned clues, you know, I've been picking up little clues. I'm 57 and I've been picking up little clues throughout my journey by asking a lot of questions to people that I look up to. And they're not necessarily people that have a zillion followers or zillions of dollars. They're just, there's something in their life that I really like. You know, whether it's how they take care of their kids or spend their time or whatever it is.

The calendar's like a blank check. Right? You get to, you get to write whatever amount you want on that for what you want out of this year.

The calendar is your most honest autobiography. It is your highlight reel, at least for me. It's where I want to put my energy towards. And when I have things on my calendar, it helps me. It gives me permission to say no, because if it's on my calendar, that means I have energy for it. And that means that if something doesn't belong there, I don't have to put as much energy. Now, I might have a wedding on my calendar. I might have other responsibilities on my calendar. Those are things I can't control. I'm talking about the things that I'm writing in that I'm excited about. How old are your kids?

Uh, 6, 4, and 1.

So this is the critical time, you know. They're all watching you. They're watching your habits. If you're efficient and you're planning and you're a doer, your kids are— there's a higher chance your kids are going to be doers. My 9-year-old son ran a marathon 2 years ago when he was 9. He's 11 now. He didn't, he didn't do that because he was playing Fortnite. He did that because he watched me go out in the rain, in the snow, have goals, you know. Like, you don't understand the impact. Even coming out here, when if you can explain to your 6-year-old, hey, I want— Daddy wanted to get better. He took a long trip to invest in himself to get better. That's a powerful lesson. Without— you're showing them, not telling them.

Right. Love that.

Yeah. Let's go do this.

Do this. Let's take a quick break. We're covering a lot of information in this episode. So the team at HubSpot did something really cool. They took my notes from talking with Jesse and they turned it into a guide on how to plan a massive 2026 in less than 60 minutes. If you want those notes, you can get them right now in the link in the description. Now back to the episode. Jesse, teach me how to plan my day.

Listen, this is so exciting, man. Thanks for being here. Yeah, I mean, first of all, before we even get started, I think it's just really important to talk about why we're here. You know, I don't take years lightly. You know, we don't get a lot of them, and we're all so busy. And I feel like in general most people plan their life around work, and I think it's really important to plan work around your life. In other words, we tend to play life on defense. Like our calendars fill up with other people's requests for time, Zoom calls and meetings and weddings and appointments and kids' stuff. Like before you know it, like what do we have to show for a whole year?

I've always thought of myself as the CEO of my company, but not the CEO of my life. And it's like that, my life is the only real project. I kind of want to think of myself more as like the CEO of my life, the architect of my life. And like an architect, I want to have my blueprints. That I want to follow. And of course I'll improvise, but I'd like to have a blueprint versus just winging it, just reacting to the latest thing, you know.

Got it. Well, the way this came about, just to give a little bit of background, is my life got very busy. You know, I have multiple businesses, I have 4 children, I'm married, I had elderly parents I was taking care of, I have friends that I want to see, I have races that I want to do. Like, there was just so much that I wanted to do. I didn't have a system for it. I just kept getting older and older, and as more and more stuff came on my plate, I needed a system. So I do 3 things every year as the backbone of my planning, and this is where I start. The first thing that I like to do is I call it getting light. I want to come into 2026 fired up, hitting the ground, not playing catch-up. I want to be ready to go.

No baggage.

No baggage. Light. And I literally— I want to feel light. I even like the term getting light, right? So getting light means closing out the year, you know, the proper way. So the— we have a little jar here, just step 1, getting light. You can see that it's empty because there's gonna be nothing in your jar when you're done. So getting light starts for me at home. So the first thing that— that getting light means getting rid of all the apps on your phone that you don't use, getting rid of— canceling all the subscriptions that you don't use that you're paying, you know, stuff. Going to your closet and donating all the clothing that you don't wear. Now, that might sound insignificant. It's very significant. It's a sign that, like, of newness. It's a sign of like, I'm coming into the year getting rid of stuff that I don't need anymore. It's your desk, coming in and not having clutter everywhere. It's your filing cabinet. It's your car. Is your car messy? Do you have your insurance in your car? Is there, like, getting everything tight? And by the way, that whole process to me could take like an hour, right? It's not like I'm talking about like, oh, I need a week. It's like your emails. I get my emails to zero. Delete, save, respond.

I mean, I have, like right now, forget email. That's how many text messages, unread text messages I have.

I don't even know how many. That's 815.

So I'm coming into the new year with 815 obligations.

Yeah.

815 guilt trips that I, you know, mistakes that I've made basically if I don't clear that out. You told me before this, you said, hey, step one, get light. I can't do that here because I'm at your house. And so I did it. And I— a couple of things that I learned right away. First of all, just doing the simplest action gave me momentum because planning my year felt big and heavy. It's like, oh God, I got to know what I want in life. And it's like, dude, I haven't known that for 37 years. Am I sure today's the day I could do this? Versus what I did was I went to my car and like, you know, the cupholder area, like I got little kids. So that is like, nom. That is like—

Yeah, popcorn, like everything in there.

I don't know, there's a whole history of life in that little cup holder. So I just cleaned out the cup holder. The simplest possible action, and right away I was like, felt a little lighter, right? Like one layer off my back. And then I did it to my desk, I did it to my subscriptions, I canceled $1,300 of monthly subscriptions of just random apps and software that we've been signed up for. So I already started to get light, and feel pretty amazing. I cleaned up my home gym, which was like, I didn't have to, nobody else works out there, but I do. And those are places I go every day, my car, my gym, my desk. Well, it feels new, feels like it's ready for something new versus same old, same old.

I think it's highly significant. You're describing momentum, and momentum is not to be underestimated. And if you start the first week you come back from the holidays, and everything's a mess, and you gotta play catch up, you're going through 815 texts. Is that a good way to start the year? Or would you rather like do all that now in this little cleanup period that we're in now, you know, get it all done and then come in like ready to, I'm in attack mode. You know, I don't wanna feel like I have a knapsack of weight on me. I wanna come in attack mode. So if you're listening to this, I highly encourage you to spend a little bit of time and get organized, get light.

All right, there we go. What's number 2?

Closing out your year. So every good business— and so after you get light, you know, what does every good business do at the end of the year?

Close the books.

They close the books. They have a review session. They think about what worked, what didn't work, etc. So I like to close out my year. So that process for me is pretty simple. The first thing that I do is I take inventory on me. So I do a little review of what worked, what didn't work. If I have a calendar, obviously I have my big-ass calendar. What I like to do is I like to go through my phone and I'll write down all the highlights. My calendar's my highlight reel. I like to write down all the highlights. Maybe it's my kids' football game, or maybe it was a concert I went to, and just make sure that I have a full recap of the year so I can look at it on one piece of paper. It's the best exercise. I can look at it on one piece of paper, see where my gaps were, see what I accomplished, 'cause a lot of people forget. Oh my God, I forgot that we went, I took this weekend trip, or I went to this.

Yeah, I can't tell you what I did in March.

So do a thorough review on one big piece of paper. Go back through your phone. And then, by the way, now you have a great time capsule too of 2025, right? So I do a little personal audit. I go through my entire year. Again, takes like 20 minutes, right? We actually got a quick gift for you. Oh, I love gifts. So we know that we— you do a year-end review, so we actually made a photo album. Hey, come on! And so, uh, this is unbelievable. You got everything. See, I think your kid just started driving this year. I would never have said— if you said to me this year, what was your highlight? I would have said, oh, I did this race. I would have never remembered. And this just happened, right? This just happened that my son got his license.

And you get to feel good again.

I'm looking at this picture, it's, it's lighting me up. I never remember. That's why it's so important to have things like this. And by the way, This is a great strategy. A great year-end strategy is to make a year-end family or year-end review book, which is something that I'm doing now. I'm going through all the old years and I'm making little books so I can remember what I actually did. Thank you so much. What was the first page that you were talking about? Can you show us? I mean, this is insane. Football championship, my son learning how to drive, Running Man, races that we did, 29:29, going to surf camp. I would have never— this is what I'm saying. This is exactly what I'm saying. To do a review, to actually say like, wow, makes me feel good. Thank you. You want to sit here and do this? And then one thing that I love to do is I write handwritten letters. I love to spend a little bit of time and write thank you letters to people that like, you know what, there's 8 billion people in the world. You chose me to be on your podcast. There's 8 billion people. Thank you so much for the opportunity to address your audience. I love sending those out. Selfishly, it's a great networking tool because everybody reads their mail. Not everybody reads their email or their text, but everybody reads their mail. And there's a different energy that goes into a handwritten letter, writing it, getting a stamp, licking it, taking it to the mailbox. Someone receives that differently than da-da-da-da, send. Right, so there's a different energy.

And you're not outsourcing this, you're not giving this to an assistant somewhere?

No. So part of it's selfish. I'm planting seeds as a networking tool, and it's just a thank-you note, like, you know, we built a relationship and this is part of that process. To, like, the recipient feels great about it, like, oh my god, this guy took enough time to handwrite me a letter. Like, it's that— that makes them feel good. I've been doing this since I'm 21 years old. Even this year, I'll write 25 letters. Even 10 is amazing. 10 to 25. You can do them on the plane, you can do them while you're watching a football game. Probably takes about 3 minutes per. So you're talking about—

Oh, that's perfect. I'll do this on my flight back.

Yeah.

I can either watch a shitty airplane movie or I can just like kind of flood myself with, you know, being grateful and spreading some good karma out into the world, you know?

There's no rule to it, but I think getting 25 out— look, You do it for 10 years, you send 250 thank you notes, handwritten letters to people, like, that's an ink stain in your brain, you'll probably never forget it. You know, so—

Ink stain in the brain, I like that.

Yeah, so that's another strategy of closing out the year, part of my process. I think that anybody can have a good year. Like, things are gonna happen, you're gonna get an invitation to something, there's gonna be a highlight. Like, to have an okay year, you could do it. Who the fuck wants to have an okay year? You don't get a lot of years, right? Like, you want to— like, I want to— can I see that for a second? Can you show that 2026? Let's hold this up for a second. This is my year for next year. I'm going to show you how to do this right now. Okay, this is fully baked. This is so epic, it's already done. I just haven't— all I have to do is follow this script. And it's color-coordinated. But this is my highlight reel. This is—

Green is family travel.

Family travel, speeches, holidays, birthdays. I have races in red. Like this is Everest thing that I'm doing. This is— I'll walk you through all this. Running Man, etc. But my point is—

You're not hoping for a great year.

You're planning it. Right. I can have a good year. Maybe a couple of people invite me on a great trip. That's amazing. Or 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? I know that if I execute this— and this isn't saying I'm not working.

This is not—

I'm just planning me before my work. Work's always going to be there. I'm going to work a lot more hours than I'm going to do this. But that's different. I'm talking about the stuff that like at the end of the day, your 6-year-old kid, your kids are going to like— you're going to have a photo book like that. There's no Zoom calls in my book. There's no picture of me on Zoom in that book. That's stuff that I did that like immediately made me smile. That's what this is. I'm going to show you how to do it right now. You talked about resolutions, but I like something that I do better than resolutions. So there's an old Japanese ritual called the misogi. You know the term. And the notion around a misogi is you do one big year-defining thing every year. This is really important. At the end of the year, you want to have something to show for it. Last year for you, it might have been like, man, I launched this insane 3-day basketball camp with Billionaires. I launched that in 2025. Maybe it was, I, you know, wrote— I'm launching a book, whatever it is. You want to have a podcast, whatever. One big, really big, year-defining thing that you have. To the point that if I were to say to you right now, what'd you do in 20— if you ask me, what'd you do in 2015? I wrote Living with a SEAL. 2017, I launched 29029, a business that I had. 2021, I did a race called Ultraman. 2023, I rode my bike across America. 2024, I did rim to rim to rim. 2025, every year you should be able to, you know, and if you can do that— how old are you?

I'm 37.

So if you can do that from— if you started now and you had one big year-defining goal and you lived to be 87, you'd have 50 monumental things that you've accomplished in your life. That's a heck of a ride, heck of a ride. So the first thing I encourage people to do is think about in 2026, at the end of the year in December, by the way, if you didn't even do anything else, but you just did this, you're gonna like, you win. What's the one thing you wanna look back on and be like, you know, I did this this year. And you might not know what that is now, but when it is, put that down on the damn calendar ASAP because it's really important. I don't think it should be something like— it's got to be hard and big, truly year-defining. Not like, "Oh, I took a trip to Italy." That's a trip to Italy. I'm talking about what you did. We launched a brand new program with billionaires for 3-day sleepover party at our friend's house. That's a big task.

Can I show you what I did?

Yes.

Okay, so last year when we talked on the podcast, yeah, you brought up the idea of misogi, and I was like, I'm going to do that. I didn't know what it was initially. You were talking about like races, Ironmans, whatever. Didn't like— I was like, I want to do something that's real to me. Like, what's the thing I would be excited about and I would feel proud of and would be hard for me?

You going to play Beethoven on here?

So I decided after the call, randomly popped into my mind, I go I'm gonna learn to jam out on the piano.

Stop it.

Because the same night that you had brought it up, I was thinking about the misogi, I was on YouTube, there was a video by this guy, he's the most famous piano player in the world, and he was playing one of his songs. I just thought to myself, I'm gonna play that.

That's unreal.

All right, my first performance, my first audience ever. That's unbelievable. That's amazing. It's so funny, cuz at my house I'll play and nobody cares, and it's like the first time that anybody actually liked to listen to it.

So yeah, actually moved us. I don't even know what to say, man.

I was like— And after what was probably one of the best moments of my life, I decided it's time to get out of there. We said our goodbyes and left Jesse's house. All right, that is a wrap. We planned our year with Jesse Itzler. He had us at his house, talk shop. We did a sauna together, we worked out together. Had an incredible day, and I'm feeling energized going into next year. I hope you were feeling energized too and got to get a little piece, a little taste of what I got today. So thank you to Jesse for making this happen, and, uh, I will see you in 2026.