The Daily Stoic - These 3 Rules Will Make or Break Your 2026 | Jesse Itzler

Episode Date: December 20, 2025

Most people will enter 2026 hoping life just gets better. Jesse Itzler knows that’s not how real change happens. In today’s episode, Jesse breaks down the three simple rules he follows every year to guarantee it doesn’t slip by.He explains why change has to start before January, how locking in the right priorities forces everything else off your calendar, and why more hustle isn’t the answer in 2026. If you want a year that actually feels different — and you want a plan you can stick to — this episode shows you how.Jesse Itzler is an entrepreneur, author, endurance athlete, former rapper, and part-owner of the Atlanta Hawks. He is the author of two books, Living With A Seal where he lived and trained with David Goggins for 31 days. His other book is Living with the Monks where he lived with an isolated religious community in the mountains of upstate New York. He co-founded Marquis Jet, helped build ZICO Coconut Water, and created the viral New Year planning tool called the “Big Ass Calendar”. Plan 2026 using the Big Ass Calendar that Jesse created: https://thebigasscalendar.com/Check out Jesse’s books: Living with a SEAL: 31 Days Training With The Toughest Man on the PlanetLiving with the Monks: What Turning Off My Phone Taught Me about Happiness, Gratitude, and FocusFollow Jesse on Instagram, YouTube, and X @JesseItzler Make 2026 the year where you finally bring yourself closer to living your best life. No more waiting. Demand the best for yourself. The Daily Stoic New Year New You challenge begins January 1, 2026. Learn more and sign up today at dailystoic.com/challenge.👉 Get The Daily Stoic New Year New You & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life🎁 This holiday season, give the gift of Daily Stoic Premium |  https://dailystoic.supercast.com/gifts/new🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

You know, you don't have to let big wireless and your overpriced phone bill suck the joy out of the holidays this year. Because right now, all of Mint Mobile's unlimited plans are 50% off. You can get three, six, and 12 months of unlimited premium wireless for $15 a month. It's their best deal the year, and it makes it really easy for you to give your expensive wireless bill the Scrooge treatment. All Mint plans come with high-speed data and unlimited talk and text at the nation's largest 5G network. Plus, you can bring your current phone and number over to Mint. Actually, we just signed up for a Mint Mobile plan to use the social media phone here at the office. And we didn't notice any kind of change in the quality of service or network or any of that.

Just a whole bunch of savings. Turn your expensive wireless present into a huge wireless savings future by switching to Mint. Shop Mint Unlimited plans at MintMobile.com slash six. That's mintmobile.com slash six. Limited time offer. Upfront payment of $45 for three months, $90 for six months or $180 for 12 months. Plans require $12 per month equivalent. taxes and fees extra initial plan term only greater than 35 gigabytes may slow when network is busy capable

device required availability speed and coverage very cement mobile.com. Hey, it's Ryan. I try not to make too many puns on my last name because I've been hearing it my whole life. But if you want to give a holiday gift of me, Ryan Holiday and the Daily Stoic, well, you can. We have a special offer. If you want to give Daily Stoic premium as a gift, you can do that, your friends, your family members, coworkers, Whoever you give it to can get ad-free episodes, early access, and exclusive bonus content. Plus, we'll even throw in premium episodes of The Daily Dad Podcast. You can get both premium plans together for 25% off. It's a limited offer available now through the end of the holidays.

That's through December 31st. You can click below to get it for them today. Happy holidays. Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers.

We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. When I was in Seattle a couple weeks ago,

I said, well, another year is in the books. Another year is gone. And what a totally normal, uneventful, not stressful, not difficult, not scary or weird year it's been, right? Certainly there's been no need for stoicism in the last 12 months. No need for focusing on what you control. No need to be resilient to turn obstacles into opportunities. No need to remain cool while it feels like everything is falling apart and the world is on fire, right? And it probably says something about a year or a moment in time where stoicism is required, but that's the moment that we're in. 2025 required it and 2026 will certainly require it.

We have no idea what the year has in store for us, but we do. you know it's going to be challenging, as all years are. And that's where today's guest comes in. I knew Jesse Itzer was going to be in town. We've known each other a long time. Actually, we met at Lance Armstrong's house, like 10 years ago. It was a very surreal dinner. Gary Vaynerchuk was there. I was sitting next to Bo Jackson. Jesse was there. It was a surreal little experience. My son was a couple days away from being born. So I was nervously checking my phone. My wife said it was fine to go, but she was like, be prepared to be interrupted because I could need to call you at any moment. So that's what I remember from that dinner.

What a weird, surreal moment that was. And so here we are 10 years later. He's on the show. And here we are at the end of a year. And what I wanted to do in this episode is talk about how do we make 2026 an amazing year, right? How do we create newness in our life as we get older? How do we get out of ruts. Jesse told me some of the rules he lives by and what the kind of review process he goes through at the end of one year now passed and how he prepares himself to have an awesome new year ahead. And I think that tees up very well the Daily Stoic New Year New Year New Challenge, which is kicking off in what, 10, 11 days. On January 1st, me and thousands of other Stoics all over the world are going to be getting into the Daily Stoic New Year, New Year, New You Challenge.

It's a new one here for 2026, 21 days of Stoic inspired challenges one per day, some Q&A's with me, discussion platform, progress tracker, a bunch of awesome stuff. It's going to be great. I'd love to see you in there, dailystoic.com slash challenge. Lock in your spot before it's too late. Don't kick the year off with some procrastination or trying to get out of things to dive in. think it'll be awesome. And speaking of progress calendars and trackers, actually Jesse gave me this awesome one. It's called this big-ass calendar. It's like the whole year laid out, like literally one giant sort of laminated piece with every day of the year. And you see it there, you're like, oh, 365 slots. What am I going to put in there? How am I going to fill this calendar? So I have a

real life to show. I have real progress to show. And I thought it's awesome. We actually hung it up in the office. So thanks to Jesse for sending that. Jesse is the author of two books, Living with A Seal, where he lived and trained with David Gagins, well before he blew up and became the David Gagins, everyone knows. His other book is called Living with Monks, where he lived in an isolated religious community upstate in New York. It's also the co-founder of Marquise Jet. He helped build Zico Coconut Water and his new year planning tool called The Big Ass Calendar, as I said, is great.

You can follow him on Instagram and YouTube and Twitter at Jesse Itzler. And I think you're really going to like this interview. I really liked chatting with him. He was great. I thought it was really fun. Then we had a great walkthrough at the bookstore as well. And then I had to run to pick up my kids. But I hope this helps you think about what you're going to do for the new year. And again, I hope you join me in the 2026 Daily Stoic New Year, New Year, New You Challenge. It's new. It's awesome. I'm excited about it. I'm ready to get after it this year. And I hope you will too. Dailystoic.com slash challenge. All right. So I think when people will be listening to this, it'll be basically the new year. And you had this great thing you were saying, like, if you just added these three things in your life, everyone's life would get better. I thought those might be three interesting habits to talk to people about kicking the year off. Do you remember all three of them? What are they? Well, I found that, like, most people don't want to change a lot of what they're doing. We live in routines. We're creatures of habit or whatever. So for years, I've just been doing these three things without changing much. and it's radically changed my life. Okay. You know? And let me just preface that by saying that, like, I'm 57.

As you get older, and maybe you found this too, it's really hard to create newness. Like, where the hell does newness come from? You have to, like, schedule it. You know, it doesn't just happen. So I've been doing these three things, and they've really helped me. So the first one is called, it's an old, there's an old Japanese ritual. It took the liberty to tweak it a little bit, but it's called the Misogi. And the notion around the Misogi is you do one,

big year-defining thing every year. Got it. So, like, at the end of 365 days in 2026, we're here, you know, last year, 20-25. Like, what do you have to show for the year? You worked hard. You had all these Zoom calls, but, like, what did you really do that you're proud of? And it doesn't really matter. Like, if you got it, if you did it in January, you'd still be proud of it in December.

You know what, like, it's something big enough that it's year-defining. Year-defining. You have, like, you have one big, I always put one big year-old. finding thing on my calendar. And you're not only just proud of it at the end of the year, you're proud of it when you're 80. Yes. And you should be able to look back, I believe, and be like, if I said, Ryan, what did you do in 2015? Well, I know I wrote Living with the seal. In 2017, I launched a new company. That's the year I did X. Right. That's the year I did X. And that, so that's something that I do. And every year, I think about what that big thing

is going to be. And it should really be something hard, challenging. And if it's truly, year defining, then you're going to learn a lot about you and grow a lot from it. So this is like run a marathon, climb a mountain. Launch a podcast. Yeah. You know, it could be physical. It could be mental. But, and by the way, who doesn't want to have something to show for the year that's like mega?

Yeah. So that's the first thing that I do. And I don't even know what it's going to look like. I actually do know what my is for 2026. But two years ago, I did a race called Ultraman. I did rim to rim to rim. So I can go back every year and pretty much do that. But here's the other thing that's great about that.

Not only do you have something to show for it, but I find that the more you experience, the more you have to offer. Yeah. You know? And I found that I'm showing up better as a husband. I'm showing up better at work. If I have something I'm really looking forward to

or something I'm training towards or working towards. It also forces me to say no to other things that don't move the needle. Like, you would think, like, whoa, you've thrown a marathon? How do you have time to train for that? Well, when you put that on your calendar, you start to weed out the things that, like, you don't need to do. You put that on your calendar.

It takes stuff off your calendar. Correct. Because you're not going to be partying because you've got to be training. Correct. Like, people might think that's insignificant. It's insanely significant. Yeah. Yeah, so I've been doing that.

Okay. The second thing, I actually named this after my friend Kevin. And I was on a hiking trip with my nine-year-old at the time, son, and my friend Kevin's nine-year-old daughter. We were on Mount Washington in the winter. It's like minus 30 with the windshield. It's ridiculous. And we're camping outside in a minus 40 sleeping bag and we're bundled up. And I'm like, I turned them like, Kevin, there's eight billion people in the world.

We're the only people out here. Like, there's no one near us. Yeah, we chose this. And we chose this. And it was your idea. I'm like, he's a police officer. And I'm like, how often do you do this? Yeah.

And the guy lit up. He's like, oh, man, ever since I graduated college, every other month, I do one thing that I normally went through done. I'm like, what are you talking about? He's like, like, instead of watching, like, the Georgia football game, I might go fishing. I might come out here to New Hampshire. I might take my kids to a show in New York City. I just do like a little mini adventure. I'm like, why?

He's like, if you can't take one day out of every eight weeks, one day. one day and do something for yourself is like you're really kind of work life balances out of whack you're pretending like you're going to get to all those things when you retire or when things calm down or go back to normal but they aren't no and time doesn't work it doesn't wait for you to do that sure so but then and then he was like here's the thing so I'll do like six mini adventures a year like one every other month so here's why those two things are so important let's say one of your listeners is 40 years old. I don't know. And they live to be 80. Yeah. And they just added from this podcast, those two things did everything the same next year. But they just did that consistently.

And they lived to be 80. Yeah. You'd have 40 year defining things that you might not have had. You'll have 240 mini adventures. Yes. It's like you see how that comes. That's a full life right there almost. It's insane. It compounds an insane value. Yeah. So once I started realizing that, God, man, I don't have to, like, change. There's 365 days. I'm only carving out like seven or eight of them, you know. But look how this works over time. That really has had, and it's true for me.

Like, you know, being 57, I've been doing this for a long time, and I built like this insane life resume of things. I don't even want to call them accomplishments because I don't look at them as accomplishments. They're experiences that have accumulated and now at 50s. I have this like, you know, I've lived with monks, I've run races, I've traveled, I've launched this, I failed at this. But through it all, it's just really been an incredible life, man. What's the third one? The third thing is I'm not really good at resolutions that they don't, most people aren't, you know, the statistics show.

Most of them don't make it even through January. But I am good at this. And that's just every quarter, I add a new winning habit. So I'm a big believer that we're all products of winning habits, winning routines, and a winning mindset. If you can get those three things right. And by simply layering in like a new winning habit, a quarter, like I don't drink enough water. I'm going to drink 100 ounces of water. Sure.

I'm never going to be late to a meet. I'm going to add a 10 minute a day meditation practice to my life. Just slowly continuing to layer in simple to add on to your everyday habits. and that's really worked out well, too. Yeah, because I think people, they're like, I want to become this transformatively different person or live a transformatively different life. But really, you're going to get there

by making a number of small choices or decisions that, as you said, sort of add up or ultimately compound over time. Because it's really overwhelming and radical to be like, I'm going to just transform. Like, it doesn't, for most people, work like that. No. It works by taking baby steps and getting momentum.

And I found like adding, one winning habit every quarter, every nine, you know, three months is totally doable. So like I'm going to start walking or I'm going to stop smoking or I'm going to like just things you're going to start or stop doing basically. Yeah. I mean, even just now, like one of the things that I'm working on is just like, I'm an interruptor. Oh. I'm an interruptor. So I'm like, I'm really like one Mississippian in my head after you stop talking to make sure that I'm not interrupting. I'm interviewing you. You should be doing the talk. Look, everyone's all. like, hey, you should really speak up more.

But I would say most of us talk too much, not too little. Right, right. So, you know, those are things, and I'm just, I'm not trying to do 15 things at once. Yeah. I'm just trying to slowly later. So that's four a year. You just have that four positive habits a year. Right.

That's big. I mean, that adds up, especially if you start doing them, and then next year you had four more, and next year you had four more. And now some of those habits you're a couple years into, you, that is how you become a transformatively different person. 100%. I mean, looking at me, I'm trying to fix the things and add habits that really will help me. So, for example, I've been notoriously late my whole life, you know?

Yeah. I'm still not great at it, but I'm, but that's something that I prioritize, like this month, man, 2026, I'm not going to be late to a meeting. Yeah. They're going to look at me like, what, yeah. We were planning on you being like. Right. And so those kind of things are what I'm talking about. Yeah.

And then, you know, layering in these little mini-adventures and a big kind of year-defining thing on my calendar. And then, you know, look, I really, I'm a big believer in planning. Yeah. And I'm aggressive with my planning. I feel like most of us play life on defense. Our life's fill up with Zoom calls and other people's requests for our time. and I don't think people need more time. I think they need a better system.

Yeah. And if you have a good operating system, I mean, for your personal life. Yeah. We have it for our business, right? We put systems in place for operating. But if you have a good operating system for your business, for me, that's my calendar. But where you're really following, like, you know, you're laying out what you want to do. And my 2026 is baked, fully baked, of what I want to do.

Yes. Family trips, vacations, one-on-one stuff with my wife with Sarah. you know, the races I want to run, the Mesoia, it's all on my calendar. Work's going to fill in around that. Yeah. But I don't think you can just wake up and wing it. Like, well, I don't know, man. And now it's all of a sudden in September.

And, you know, like, oh, I only got like 90 days left of the year. Like, it doesn't work like that. Yeah. Especially as you get older and you have more kids. Maybe when you're younger, you could do that. But for me, it just doesn't work. Creatine isn't just for building muscle. It's actually a daily essential for strength and focus, recovery, aging, cognitive performance. And now, Momentus, who's today's sponsor, is making your daily creatine routine even easier with new creatine chews. I took two of them this morning. Each chew delivers exactly one gram of CreaPura creatine monohydrate, which is the gold standard. It's single sourced from germ. Germany and its NSF certified for sport. Momentus spent years testing until they created this new

chewable that actually meets their Momentus standard, which is uncompromising science, meticulous sourcing, and real transparency. This is performance without pause made to support your body and your brain every single day. This is creatine done right. And right now, Momentus is offering our listeners up to 35% off your first order with promo code Stoic. You just got to go to Live Momentus. and use promo code stoic for up to 35% off your first order. That's livemomentis.com promo code stoic. Human. Your body has a performance superhighway.

60,000 miles of blood vessels that deliver oxygen and nutrients to every cell. This, of course, is your cardiovascular system. It's the foundational system that powers everything we do. Both elite athletes and longevity experts invest directly in the cardiovascular system because supporting healthy blood flow is critical for energy, recovery, mental clarity, and overall performance. That's where human comes in. That's human with two ends.

They started out of research at the University of Texas, near where I live, and have 15 years of experience making award-winning supplements for nitric oxide production and healthy blood flow, now used by over 160 pro and college sports teams. Human cardiovascular health daily is a plant-based and made from clinically. studied ingredients like grape seed and seed kelp extract. It supports nitric oxide production for healthy blood flow and energy while also supporting blood pressure and helping support the delicate interlining of your blood vessels. Just two capsules each morning will power energy and recovery while also playing the long game by supporting long-term vascular health and

healthy aging. Human has an exclusive offer for our listeners. You can visit human.com slash stoic for an extra 15% off your first purchase. That's enter code STO-I-C. Stoic at checkout. That's human with two ends.com slash stoic for an extra 15% off with code stoic at checkout. There's a famous story you might like about Alexander the Great, so he's trying to conquer this distant country, and obviously his reputation precedes him. So the rulers of the country sort of get together and they call a meeting like a parlor and they go, hey, we'll just give you this land over here.

You let us keep this. We'll give you this land over here. And Alexander the Great goes, you know, I didn't like march across the world to take what you're going to give me. He's like, I'm going to take what I'm going to take and you're going to keep what I give you. And Seneca tells this story because he said, this is our relationship with sort of self-improvement versus work, pleasure, etc. Right?

He's like, basically what we do is we let work take up all our time and then we use the little bit of leftover. So I think it's interesting what you just said that, like, if you lay out your calendar and you go, here are the important things that I want to do with my family, that I want to do with my health, that I want to get better at, you're like, work will find a way to fill in all the cracks. For sure. But most people, most of us do it the exact opposite, right? You're like, the presumption is the work gets up the vast bulk of your week and your year. And then you're like, and then I'll make time here or there for family, friends, et cetera. And then we tell ourselves this lie, of course, we go, and I do it all for my family. And it's like, the calendar doesn't lie.

You, you did it all for work. And then you gave the scraps, the leftovers is what your family got. It's what you got. It's what, you know, your spiritual health, all these things that you should also be working on. That gets the leftovers. And we should probably flip it. Yeah. I agree. I mean, that's what I've, I mean, one Mississippi. Yes. That is, no, I mean, that I agree. I mean, I think work's always going to find you, man. And if you think about how much time most people spend laying out their work schedule and reviewing that versus how much time they actually invest in planning their own personal life and a life of adventure and the things they want to do, you know, I just think it's as important to prioritize and plan your personal life as it is your

business. Yeah, to be intentional about what you want to do as opposed to what most of us do, which is, look, work is paying me money, and if I don't do it, the bill collectors will yell at me, or my boss will yell at me, or my clients will yell at me. So that gets all the focus, and then you're like, the rest of the stuff, I'll figure out, I'll wing it, or it'll get the leftovers. And like, your kids aren't going to yell at you now for it, but they'll resent you for it later, or you'll look back and go, hey, here's all the things that I miss that I can't do again. You know, it doesn't manifest itself in the day-to-day the same way that it does professionally. But you find out when the divorce papers come through or the doctor gives you the diagnosis for some preventable thing.

It's funny because I mentioned that I name that Kevin's rule, you know, that kind of principle. But I've been naming the people that have had the biggest impact on my life for the most part. And I've had a lot that have really impacted me. But the people that are the biggest impact aren't the people that have like necessarily millions of followers. There are people in my regular day life that I've come across friends or associates or whatever. And throughout my journey, I've been naming like tips, like Kevin's rule. I have my mom's, I have all these different rules. And you were just talking about your kids or children in general.

And it reminded me of like one of the rules that I had that I learned from a guy to basketball camp I was at is that he said to me and just talk about. is like, you know, I have a rule that I'm never too tired from my kids. Sure. And I love that. And it stuck with me. So I have like probably 20 of these rules I've named after people. Maybe one day someone will name a rule after me. But I love that.

And I think about it all the time. Like if I come home from a trip and my kids want to have a baseball catch. Yeah. And I'm like, oh, I'm too tired. You know, like something's wrong, you know? So. I think about that. Like, I try to remind yourself, the pool is never too cold.

Yeah. It doesn't matter that I just got dressed. Ryan's rule. I just got dressed. It's like when they want you to jump in the pool, you jump in the pool. And I don't always do it. You know, it's a rule that I don't always fall. But I certainly feel guilty every time I don't.

It's like, what am I prioritizing over this? And it's at a request. It's like an invitation. Yes. You know, that's a rule I got from someone's name is Russ Roberts. His rule is whenever your child, it offers their hand, you have to take it. Obviously, literally if your kid's like, wants to hold your hand, you take it.

But I think what he really means is like, when they're like, hey, dad, do you want to play video games? Or they're like, hey, I need to go to the store. Can you take me? It's basically whenever they are inviting you into their life or to do something with them, you take it. Yeah. I have a similar rule.

It's Ben's dad's rule. My friend Ben told me this about his dad growing up. And he said that, so for me as a parent, I find myself encouraging my kids to do the things that I love to do. Sure. So I'm like, oh, let's go play basketball. I love playing basketball. They might not want to do that.

Right. Ben told me that his father would find out what it is his kids like to do. Like, let's say maybe his son liked to bake. You know, he would then take baking lessons. Wow. And he would do, oh, man, it was like a mo, I was like crying when he told me this, man. It was like, I loved it. And his dad would sign up for all these things that his dad had no interest in doing.

Right. But his kids were interested in. I almost broke down. I was in a car once. I was in San Diego going to a talk and the driver picks me up and I was wearing a Metallica shirt or something and he goes, oh, do you like Metallica? Some heavy metal band. And I go, yeah, I do. I was like, do you know? And he was like, well, I didn't. And I was like, what do you mean? And he's like, you know, my son is really into heavy metal. And he's like, so every year I would take him to one heavy metal car. So he's like, I've seen this band and this band and this bend. And he was like, I never liked it.

But after, you know, 20 years of this, like I've seen all of them and I am a fan. I loved it so much not just because it was sweet, but like it tends to be with music or any kind of like cultural stuff that parents have the exact opposite reaction, right? It's like you like rap music and your parents are like, you can't listen to that. It's not appropriate or like turn that shit off. Like it's not just that parents tend to not be interested. They're anti-interested. They're like trying to crush that interest. And here, this dad with a thing, and this would have been quite some time ago,

so the music would have been more controversial than it is now. He's going like, no, no, no, you're interested in it, therefore I'm interested in it, therefore we're doing something together about it. And whenever you hear stuff like that, it's just the sweetest thing in the world. Oh, my God. Yeah. You got to do that. Yeah, especially because, like, you know, it all goes by so fast, which everybody knows,

but, you know, you think you're going to be the age you are forever. Sure. And, like, it's getting harder to do something. Like, you know, like, I'm 57. But, like, how many more relevant years do I? Like, I was on my, I have a lake house and I was taking the kids water skiing over the summer. I didn't see any 70-year-old's water skiing. Yeah, sure.

When I was on Mount Washington and it got a little busier the second time, we went, I didn't see these 70-year-olds going. I'm sure there are, but, like, I didn't see it. Well, that's the lie people tell themselves about travel and stuff, right? Peter Attia talks about this. Like, you're going to, you think you're going to do this when you stop working. Nobody's having fun traipsing around Italy when they're 75. They can't do most of the things. It's painful.

And so the whole point is you should do it now, not just because you might not be able to do it later because you could die. But it just won't be as good later. Yeah, you won't enjoy it as much. Yeah, I know. So, I mean, like, that's basically how I live my life. I mean, I'm trying to, I'm almost living, like, in a manic, like, trying to do as much as I can now. I don't want to say in a crazy way, but in a designed way. I would say, you know, like, because I'm very aware of that, you know, I was very aware, like,

when my parents were getting older and they lived in Florida and I lived in Atlanta, I wasn't seeing them that often. Maybe I'd see them like four or five times a year. Recognizing, like, man, if they live another 10 years, like, I'm only seeing them two or three times a year. Like, I don't have 10 years. I have 20 visits. When I started to, like, look at things like that, and now I'm looking at that with my kids, too, you know, it's changing. Yeah, I like, I like, like to look at things in five-year increments. So my son now is a sophomore in high school. So in five years from now, he's in a totally different phase of life. Yeah. In five years from now, my whole life looks different. So right now, everything's great. All my kids are home. Sarah's parents are

alive. You know, I lost my parents. Within the last five years, I lost both my parents. But in five years from now, all my other kids are in high school. My oldest is out of the house. I'm almost an empty nester. Parents, Sarah's parents and those that are older and they're 80, they're now in their 90s. It's a whole different chapter. Sure. You know, so you got to think about that.

And that will help you think about, at least in my case, how I want to live out this year, 2026 and beyond. You know, and that really dictates, do I want to go on that trip or do I want, my son's only here for two more years? Right. Is this going to, am I back by six o'clock? Like those decisions, they're, like, magnified and multiplied. And it's a really important lens to look through life versus like, oh, yeah, I'll just do it tomorrow.

And no, I had one of those where I was like, you know what, like, I get to pick my own schedule. Like, I was like, you know what? Maybe I'm just like not going to come into the office one day a week. And then I'll just spend more time with like it. And I kind of like, I've been thinking about it. And my wife and I've been talking about it. I was like, a plan. And then I was like, you know what?

Like, this year I'm going to do it. And then I, and then I was like, wait. Like, I missed it. Like, me not going to the office on Friday, does it do anything? Because I still have to take them to school. Like, I might as well go into the office after I dropped them off from school. Like, there was a time when that would have been really powerful and important. And this is, I think, a lesson just beyond parenting.

It's like, as you're making these plans, actually the value of those plans is often disappearing or the ROI is diminishing as you go. Like, I could have been there. You know, this time. But they're like, what are you doing here? You know, like, what did you do all day? Like, because I could, like, that little thing is gone. That opportunity just where they're at home all day. They're not at home all day. And by the way, they want to do stuff that doesn't involve me, you know, on Friday. Like, that's what's always changing. So you're always telling yourself, hey, I'm going to get to it later. But that's something else that Seneca talks about. He says the one thing all fools have in common is they're always getting ready to start. So you're making the plan you say you're going to do it but like the whole point is you got to fucking do it now because now is when the math on it actually works not two years from now yeah the last three years I've taken trips with a group of friends there's about 10 guys and and we wrote our bike across America we went to Finland to tour the best sonnas in the world we went on a sauna tour of Finland we did rim to rim to rim at the Grand Canyon you do that one where you jump in the actual

like through the hole in the ice yeah in the Baltic we did we did it all and when I first sent out the email, hey guys, we're going to go to Finland, you know, I literally wrote like, I know you're going to say like it's, I don't know the time or whatever, put this down and build around it. We're going to Finland, you know, and we've done it. And for the last three years, it was never the right, two weeks to bike across America, you're never going to have, everyone's got jobs. That's inconvenient whenever you do it. It's never going to be the right time. Yeah. You know, so let's just do it. And we're so glad we did it. And we're, and we're so glad we did it. And here's the interesting thing about that. This is crazy. But of the 10 guys that

did these trips with me, I only knew one of them 10 years ago. So I got this new friend group from doing these things like and that didn't exist in my life like 10 years ago. And I think a lot of people as they get older think like, where's my tribe or, you know, I don't know or like that's going to give you one. No. No, they're not. You got to go. and make an effort and not everybody wants that, you know, but it's been amazing, you know? I think there's something about like the Masogi thing, like doing challenges. Like so for Daily Stoic, we do this thing called New Year, New Year, it's 21 days of like challenges. And the whole point is they're like fucking hard.

Like how do you spend the first 21 days of the year doing something challenging? And like some of them are more challenging than others, some are physical, some are mental, some are spiritual, whatever. But I do think there's something about like doing hard stuff that's really good for you. And there's big hard stuff like I'm going to bike across America. And there's also big hard stuff like, you know what? I'm going to clean out that drawer in the kitchen that has become a doom bin of just everything. Like, I'm going to do this thing that I don't want to do so I can be the person who did it.

And that draw is so hard, I can't even do it. Exactly. I can't even do that. Right. Yeah. It's easier to run 100 miles than clean out that drawer. Yeah. Or mine is like I'm usually more of like an inbox zero person, but it's like I'm going to like declare email bank

bankruptcy and white. I'm going to start with zero emails on January. That's like one of my goals. Oh, I nuke my emails in December. I go to zero. Yeah. Delete all. Yes. Every year. Yeah. I mean, a big thing for me is coming into the new year light. That's like a theme. Like I want to come into the new year as light as possible. I don't want to carry a lot of stuff over. So that there's a process that I do. Yeah. The first thing that I do is I clean out my closet. That might sound ridiculous. Yeah. But I don't want to go into a closet with 8,000 things I don't wear. Yes. So I just have a very simple rule.

If I look at something and I'm like, should I keep it or not, that I always say, someone needs it more than me and it goes in the donate box. Yes. So I come in, I take care of my closet. I get it as lean as possible. Then I go to my desk. I get rid of all the papers, everything around that, car, everything gets clean. Emails, done.

Subscriptions I don't need, gone, deleted. Like, I literally spent, what does every business do at the end of the year? They balance the books. They balance the books. They do an audit. They do a review. I do the same thing with my life. And I'm going through, I haven't started yet this year, but I'll start to do that in, this is airing in January.

In December. Yeah, January December. But I will have done that. By the time this airs, I will go through all of that stuff, cleaning everything out, and email is a part of it. And I want to come into it, like, I don't want to be cheap. I don't want to come into January behind. Yeah. I want to attack January, like, clean light.

And I just call it coming in light, you know. And it's a process. I write thank you letters every year. Yeah, I read that. That seems like a good foundational habit. You wrap up the year. Right. How many people do you write thank you notes to?

Anywhere from 25 to 50 normally? Handwritten. Oh, of course. Yeah. Yeah. Handwritten notes hit so much harder. And then that lightens it for you because you're like closing. Closing it up.

You're balancing your debts or you're canceling out your debts or whatever. A little bit. It's also a habit that when I was 22, so like between the ages of 18 to 22, I slept on 18 different friends' couches. They were putting me up, trying to figure out how I'd be as an entrepreneur and, you know, trying to make it as an entrepreneur. And I failed in everything, so I needed couches. And I didn't have a lot of money, but my entire marketing campaign and networking campaign at that time was to write handwritten letters. I wrote 10 a day. I wrote 3,000 in one year.

Literally. I'm not kidding. Postcards. I'd send them to everybody. And it stuck with me because people would like remember them. You know, like, no, not everyone checks their emails or their DM. Everyone reads their mail. Well, especially now, getting a handwritten card is like even more out of the blue.

You'll get one. When I write into people whose podcast I was on, like usually I write like there's 8 billion people in the world and you chose me to be on your podcast. Like, thank you. Yeah. Thank you so much. That's another one. Like people want, they're like, I'd like to be more grateful. I want to practice graduate.

But it's like, it's not a thing you are. It's a thing you do. Like, you, you, it's not to this feeling. It's like, are you expressing it? I have a rule. Can I share a rule? Please. So, um, I have this.

Jesse's rule? It's Charlie's rule. Okay. After my son. All right. So my son at nine ran a full marathon. Whoa. So he was getting a lot of attention from it.

And I didn't even know he was doing it by the way. I didn't know to mile 20. I was, we were running the same race. And then I was like, what are you doing? Yeah. Like, I got six more miles left. I'm like, I'll run it with you. After that, he was getting a lot of attention.

People are like, you know, Charlie, that was unbelievable. And he didn't really know how to handle that. So he kind of like would look away when people congratulated him. He was like kind of shrug and be like, mm, thanks. And I sat all our kids down at dinner one night. And I said, Charlie, listen, if someone's giving you a compliment, you know. And I realize, like, I don't really take compliments well either. It's uncomfortable.

It's uncomfortable. But if someone's giving you a compliment, they're putting the energy out to recognize anything that any of you kids have done. It's important, you know, to look them in the eye and hit the tennis ball back and say, thank you so much. That means so much to me. Versus shrugging your shoulder and say, thanks, makes them feel uncomfortable, almost awkward where they're going out of their way to recognize you.

And it's really important that you guys just, you know, just try it and watch how they light up when you do that, you know? and I was teaching a program, like a coaching course, and I was telling this story to a bunch of people and explaining how, like, then I realized, like, I don't take compliments well. Yes. And I went through the, you know, we all practiced it.

And I walked over to one of the ladies that was there a couple of minutes later. And I said to her, I was like, Melissa, I heard that you got an Airbnb and you rented this Airbnb the night before the event. All the people came and they had dinner at your house. I'm like, that's unbelievable that you took the time and energy to do that. And she looked at me and she shrugged and she went, thanks.

And I'm like, Melissa, I just spent 30 minutes. And I realized that people really don't know how to take a compliment and how important that is for your own personal brand. You know what I mean? Especially at a young age. Like we want to get a reputation of being, you know, vibrant or personable or whatever. So I named the Charlie's rule after and I'm super aware now. And the rule is you got to take the compliment and then hit the tennis ball back. Yeah.

Thank you so much. I really appreciate it. Right. You know, they're going out of their way to recognize you. You have to make sure you go out of your way to thank them. So if you send me a thank you card, do I have to send you a thank you card back for the thank you card? And then we just go back an endless amount. No, but if I say, Ryan, this is an insane studio.

And this must have taken a lot of time to, like, physically do this. And if you guys put all these books here by yourself, that must have been an amazing. I'm proud of you, man, because this is a really good. cool environment, it would be nice for you to look back. I'd be like, just don't just change the subject. You're like, cool. I truly recognize how unbelievable this is. And by the way, it is frigging amazing.

It would be nice for you to return that to me. Well, the other thing you can do, by the way, as pertaining to this, is like, if it makes you uncomfortable, be like, it's great. Let me tell you about who actually did it. Yeah. Because, like, I didn't do any of this. This kid named Braden Wood, who's this kid came to my house. He was 16. He was like, hey, can I, like, do odd jobs or whatever. And he's now 24, and he does

incredible stuff like this. You can hit the compliment back by explaining and articulating what you put into it, what it means, how it happened. You don't have to, you know, you're not dodging it, but what you're doing is meeting that person's interest in curiosity and acknowledgement with those things back. Just think there's a lot of things like that that anyone can do. that make a big difference in, I'm a 980 on my SAT guy. I've sold five companies. I've had five exits. I've had a lot of egg on my face too.

But it's certainly not because I'm the smartest person. Sure. But it is because I've been writing letters and I've been communicating and I've been following up and I've been doing things that anyone can do. I'm so back of the pack as an entrepreneur. I don't even like to say, when people introduce me as an entrepreneur, I don't even like it because there's so many better entrepreneurs. It's like being a writer.

It's just, it's not something you should be describing their self by. It's, it's better for other people, but it can still be a little. I feel like I'm really good at living, at living life and designing life. But, you know, if I was going to say to you, what would you look for, what would be the things you'd be looking for if you were hiring a CEO or building a team? What would be some of the traits? And you'd be like, oh, I want them to be, you know, enthusiastic and honest and hardworking. And, you know, you could even make a list. And every word that you threw at me, I guarantee they would all be attitudes and not skills.

Yes. Enthusiasm isn't a skill. Yeah. It's a choice. It's a choice. Sure. It's an attitude. You don't go to school to become enthusiastic.

Right. A skill, you can go to a skill to become a painter. That's a skill. School to be, you know, learn a skill, a trade or whatever. And so the Charlie's rule plays into that a little bit. It's like, you know, there. The things that anyone can do, why not do, why not choose to do those great? Yes.

Like, choose to pour your soul into everything you choose to care the most. Yeah. You know, like make a decision. Like, I always tell my kids, like, you guys want to play and be the best team. Yesterday, I was dropping my son off of football. Literally, when he was going out of the car, I was like, be a leader. Hit everyone in the helmet. Pick them up.

Great play. Like, stand out for that. You can drop the ball, make it. But anyone can do that. Well, that's the thing is where whatever you end up doing in life, someone can probably teach you the skill of doing the thing, but they can't teach you to want the skill. They can't teach you to show up on time. They can't teach you to not be fucking nuts. You know, like, they can't teach you to be honest. Like most, I think about that all the time. Whenever you're dealing with like a contractor or something, you know, like those trades that are just incredibly frustrating whenever you're dealing with something like around your house all the time.

And you go, I just go like, at first I'm frustrated. It's like they're not coming back on time. They're doing this. You know, and then I go, you know what, the actual lesson here is I could learn how to lay floors, right? Like, so whatever happens in my life, I could figure out this actual trade. Not to, not to say that it's easy to do, but you could figure it out. It's not rocket science. Right. But, like, apparently it is hard to have some of these other skills, like being dependable, being honest, you know, getting things done quickly, having a sense of urgency. Like, you go, oh, okay, like, this is frustrating.

But what it is showing me is that if whatever happens in my life, there's a lot of rungs you can fall and still be reasonably successful because the rare things in life are what you're saying, enthusiasm and creativity and, you know, connection and service. All those things are the things that most domains and fields are desperately lacking in. And you can't outsource it. Like you can't outsource enthusiasm or soul. or you can't outsource, you know. Personality. No, I mean, it's like those are things that they're more like decisions. And I think that, you know, they don't teach those things at school.

Yeah. But everyone has those. Everyone listening to. And if you don't have the other stuff and you overcompensate by, thank you so much, that means so much. And writing letters and doing all these things that, like, to me, I never took a business club. My dad on the plumbing supply house. We never talked about business. I don't rely on things that were intuitive to me.

Like writing a note. it was intuitive. Like, I don't know, people are going to get that. It felt like the right thing to do. My dad wrote me letters when I went to camp. Sleepboy camp is a boy every day. I'm like, I loved it. People are going to love it.

And I think that those things, you know, especially if you're on a down tick. Because one way to put like a little stop plug in the down tick is to build momentum. So if you're doing things like that that make you feel good and make other people feel good, you can kind of very often stop the momentum, which is really important. Anyway, I don't know how we start. talking about this, but I think that's, it's an important thing to think about, you know, because anyone can do it.

Well, yeah. I can never play in the NBA. Yeah. You could teach me how to dribble this and I'll never be able to play in the NBA. But I can play in this field at a high level doing things that anyone can do. Okay, so you sent me your big-ass calendar thing. There is something to be said. Like my book, the book I'm working on right now, is laid out on my wall in my office.

There's something to be said, I think, especially in a world where everything is, an app or it's tech-driven for like just old school pen and paper and physical representation of things. Like to go to your point about, hey, do one big activity, do eight or 16, you know, many experiences, when you see a calendar with 365 squares on it, you go, oh, 16 experiences is nothing, right? You know, like it's half of one month. And you realize, oh, I can.

definitely make time for this. There's something about seeing it all laid out that's very empowering. Yeah, I couldn't operate without seeing my whole, the calendar, our calendar is 365 days, the big-ass calendar on one piece of paper. And I couldn't operate without seeing and tracking towards my goals, seeing where there's gaps in my time and laying out the whole year. Like, first of all, I'm visual, we all are. We think in stories and we remember in stories. So I don't get that on my phone when I'm scrolling. It's not a big enough picture. I can look at my week laid out on my phone, but I can't, you can't, a month is not,

is too, that's too many little things on one iPhone. When you start to see what you're actually doing in a year over the course of 365 days and like only a couple of those squares are filled up, you're like, whoa. Yeah. You tell yourself I worked on this for eight years, but actually you worked on it like eight days for eight consecutive years, which isn't that many. Function is the only health platform that gives you the data that most people never get, and it gives you the insights to start doing something about it, too.

With Function, you get access to over 160 lab tests annually, from hormones to toxins to markers of heart health, inflammation, and stress, and for an additional fee, you can also access MRI and chest CT scans, all tracked in one secure place over time. It's a near 360-degree view to see what's happening inside your body, which is why so many top health leaders are all behind function. If you want to give someone or yourself something truly meaningful this year, give them the clarity that comes from knowing their health.

Most gifts fade, but this one helps your loved ones stay healthy. And you can own your health for just $365 a year. That's just a dollar a day. You can learn more. Join using the link. Go to functionhealth.com slash Daily Stoke, or use Code Daily Stone 25 for a $25 credit towards your membership. So we live on a Halloween street.

We knew it was a Halloween street when we moved there. And then it has quickly become a Thanksgiving and then a Christmas street. Everyone's vying to outdo each other with their decorations. And I'll admit it sneaks up on us, especially as the competition gets more and more. The holidays are here. And if you're looking for holiday decor or last minute, refreshes around the house, get what you need fast with Wayfair. That's where we got a bunch of our Christmas decorations and a bunch of essentials because we have some of my wife's family visiting us

for the holidays, blankets, linens, all that kind of stuff. You can get all of it at Wayfair. You can also get big stuff like sofas and dining tables, beds, desks, and more all shipped for free. They don't have huge delivery fees for furniture. Find all your must-havs from furniture and decor to appliances and cookware all in one convenient place. Get last minute. Hosting Essentials, gifts for all your loved ones, and decor to celebrate the holidays for way less. Head to Wayfair.com right now to shop all things home. W-A-Y-F-A-I-R dot com. Wayfair, every style, every home.

I hired a speed coach to work with one of my boys on their speed, and the guy came over, and he must have drove an hour away. First he called me, couldn't get me on the schedule for like six weeks. So six weeks go by He shows up in a car We do a session I thank him so much For coming out

And I said you know Wow you know six weeks I want to set up another session but like this took six weeks You must be so busy And he's like busy He's like no I'm not busy I just got back from four weeks of fishing

Or whatever the hell he was doing I go what He goes oh no no It's by design I said what do you mean He said well like I realized that if I had to do all these sessions. It would take up all my time. So I moved to an online platform, training kids

had to run faster by videos. This is just doing this as a favor. I follow you on social, whatever, he's like, but that's all by design. And I left that. It's coach's rule. Yeah. I left that. And I'm like, I want to live my life by design. Yeah, sure. I want to design the life that I want to live. How many times I go away with my kids or what I do. Like almost certainly that guy makes less money than you, but you're not taking four weeks off to do anything. Well, no, you know what he is? Insanely time rich. Yeah.

Maybe I may be financially wealthier than him, but he's time rich. And let me tell you something. Don't minimize how important time rich is. It's probably the most, who cares you if you have all this money and you're not like taking the time to do what you want to do? Yeah. How many powerful people have no power over their schedule? A lot.

Like they wake up and somebody is telling them what they are doing all fucking day. and how many of those things do they actually want to do. So how powerful really are they? Right. No, this guy was the happiest guy. It reminds me of like, I'll never, like certain things you think about in your life. I was running when I was 23 years old. I lived in New York City.

I was on the west side and I went up to, on the water, up to like Harlem. You know, I was like in like 100 or whatever. And there was a guy I ran by every Sunday and he had this little fishing rod. I'll never forget this, man. And he was fishing over the side into the Hudson River. river. He had a little boombox, like a little lunch, like, lunch, construction lunch pail. And he looked like the happiest guy I've ever seen in my life. This guy, like, his kids were running around. He had a little dog. And you could just, I don't want to judge, but like based on the look of everything,

the shoes, the rips, the holes, the whole dirt. You know, like, live in a penthouse. This guy was not living on Park Avenue. Yeah. All right. And he was friendly and happy and every week and greeting people and fishing. And I was like, fuck. Yeah. I'm grinding my ass off. Right. Making X amount of dollar.

I'm probably making like 90 grand and spending 130. Yeah. You know? And this guy's probably like, you know, like, probably saved more money than I had. Yeah. And it's more time than I have. Right.

And I'm like, geez. But it's stuck in my head. Yeah. And time rich is important. But the life by design also hit me hard. Yeah. And that's what the calendar is. It allows me.

to design the things that I want to do first and fill everything in around that. Yeah, I have these, I do this journal and you write one line a day for five years. And it's very weird, like, you know, the first year, it's whatever. But like I'm almost done with my second one. So I'm on the fifth line. So you journal every day? I do. It's one of my favorite habits.

That's a good habit. If you're like, hey, I want to pick a new habit for 2026, just like I'm going to carve out five minutes to do some journaling, ideally on paper, just to process my thoughts, like to get I'm out of here and onto the page. I'm going to do that five minutes a day. That would be, I think, a foundational habit that would make most people happier, more self-aware, calmer. And you definitely have the time.

In one book? You keep it in the same book? So this one, the journal I love, I do a couple, but this one is one line a day for five years. So you're like, okay, here's where I was last year, the year before, the year before. It's very helpful to see the passage of time that way. Oh, yeah.

Because most of the time you're journaling, and then you finish the journal, only start a new one. It's a true autobiography of your time. Yeah, you're seeing and you're like, oh, I've been, sometimes you're like, oh, it's good. I'm consistent with this thing. And then other things you're like, oh, I started this and then it fell off. But there is something about, you want to see like, hey, are you getting closer or further away from the life you're trying to live? Because most of us are saying, well, yeah, I'm doing all this so that someday X, Y, or Z will happen. But like, your life isn't someday in the future. This is your life. And so I do try to think about

how close is the life that I want to the one that I have right now. And if it's too far, then, you know, it's not great. That's not great because now you're deferring and hoping that a bunch of things happen a certain way instead of just doing it. What don't you have that you want? Yeah, there's not that much. Like, you know, that's a question you probably get all the time. People are like, what are you working on next? And you're like, I like what I do.

This is, I want to do more of this. That's my, like, the idea should be that you're not. not, there's definitely be things like I want to run this race or I want to try this. But like, the idea of like, well, I got to do this new thing to top what I did before or I need to do this very different things. I don't like what I'm doing. I like, I like writing. And so if I can wake, if the majority of my days are I get to wake up and do that thing, that's success. I'm not trying to get away from that. I'm trying to do that. That was the whole, that's, I worked really hard to get in that position. Why am I going to try to get out of it? Right. Right. Yeah.

Yeah. It reminds me of another rule. Yeah. Okay. Lieber's rule. I got offered, I had like no money in my 20s, so someone had offered me $10,000 for 10% of my life going forward. And I was like, it was this guy, Steve Lieber. And I almost took it because I needed the 10 grand. By the way, 10 grand at that. I'm Elon Musk. Equity is expensive. You give me 10 grand. I'm Elon Musk. Sure. Sure. But I remember the first time I made $10,000. I was, what am I going to do with all money yeah he told me he was telling me about his life and he was and he was a manager and he came

to a point in his life where he would rather make 25 cents working for himself than a dollar working with the guys that he was making a ton of money but he wanted he was willing to take that to have control yeah and be in charge of his own destiny and like as a 20 you know like again like that makes a lot of sense now but like when you're 21 you're like I never heard anyone talk like that ever, you know? That was a pivotal moment in my life. Yeah, because most people are their vision of success. If you actually talk to the people that have that, they're all trying to get out of it. Yeah, exactly. You haven't actually thought about what it would be like to, you know, then you're like the dog that caught the car. Like, it's actually a miserable.

I remember Peter Thiel told me that once he went to Stanford and then went to Stanford law, and he got into like one of the biggest law firms. And then he realized he'd spend his whole life trying to get into a place and he talked to the people at the place. And they were all talking about getting out. And that's, I think that's more, that's true more often than people think it is. Yeah. Oh, for sure. Like you talk to people in politics, which, so a lot of people seems like it would be so cool.

And then they all just talk about how fucking much they hate it. Well, go talk to someone that's, that, you know, sells their company. Very often, like they go through, you know, they built up the stuff for this one day that they're going to exit and sell their company. And then they sell it. And very often, if it's a founder, they're really miserable. tragedy of their life. Yeah, they're miserable.

And then what do they do? They go start another company. It's like, you already did it. I know. You could have just stayed there. Yeah. Yeah, we are really good at coming up with ideas for exiting or getting to a place as opposed to how do we develop something sustainable.

Like, same true. We're good at planning vacations for like visiting places we want to go as opposed to designing a life that we like living in and don't desperately need an escape from. Yeah, coaches rule. You got to live, you know, life by design. Yes. I feel like my dad had that. I think it's real.

And I think it's just so important, man. Like, and I just, I recognize that people don't have, you know, people have to work, obviously. Of course. And it's, you know, it's easier for you to say, you know, I get all that. But my life at 21 when I look back at it was very similar to my life now. I was still running marathons. I was going to the polar plunging, Kolding Island. That was free.

I was going to all these speeches and offerings around New York City that didn't cost a lot of money. I'm doing on a bigger scale now, but I'm still doing the same kind of things that I love to do. I just have more brown rice on my plate. You know what I mean? So I was lucky enough to kind of recognize a lot of that stuff early on. Yeah. You know? And when I started Marquis Jet, which was a big deal for me.

Yeah. I was 28, 29 years old. I started this private jet company with my partner. we grew it from nothing to $5 billion in sales and we sold it to Warren Buffett's NetJets, Berkshire Hathaway's NetJets. And the gift wasn't like the money, which was definitely a big deal for me at that time.

Forget it. I'm not going to, but I'm 30 years old and we're flying the who's who of CEOs, athletes, entertainers, pop culture. And I'm getting to meet all these people. And I'm fucking young. Yeah. Single.

I don't know anything about, anything, you know? And I was obsessed with their habits. Yeah. And so any chance, I got a chance to meet someone at the airport or at one of our events or whatever, I'd ask them a million questions, like, where do you vacation? How many newspapers do you, for the time you go to bed? Yeah. You know, like, what do you do with your money? Like, anything, and they were willing to share, you know? You would think people would ask more than they do. Right. And you'd be surprised how people want to help people. Yeah. So when you ask, you get people like, because it's something they spent a lot of time thinking about and there's not that many people to share it with dying for people to ask them

they want to share all this stuff you know like especially if you toot a little ego like you know like Ryan you're the best in the world you're the best author I ever met what's the key to like oh well first of all thank you right I really admire how you do this and you're picking some tiny thing they they don't get to talk about a lot right and they're like yeah how much time do you have anyway back to that so I was obsessed with people's habits and I I started to pick up and try some of them, you know, like, I'm a product after 30 years ago of trial and error of all these different habits people were talking about, you know, like, oh, I read six newspapers. I read this and this. I get seven hours of sleep. I get up early. Like, I would try

all the different things because that's how, you know, you learn. I was at a conference and my wife's become really good friends with Warren Buffett over the years. And very often he'll ask to sit next to Sarah so they can get caught up or whatever. And like, sometimes, it's uncomfortable for me because I'm the plus one, which is fine. But I'm just sitting there while they're having this conversation and like, no one really wants to talk to me. They want to talk to Sarah.

And it's like weird, but it's like we go to this event and this time I'm sitting next to Warren and we're at the same table, but somehow Sarah, and I know Warren well too, but we're not... You sold him your company. Yeah, but so I just, I asked him out of nowhere

about his dad. And I said, Warren, can I ask you crazy question. And now this is a guy that's been asked about the yen and dollars and stocks for 70 years. No one's ever asked him anything like this. I said, I got four kids. Did your dad ever take you on a one-on-one trip when you were growing up? Three and a half hours later were still talking about this. Yeah. Three and a half hours later. The host of the conference was coming. They thought I was hogging him like from everybody. else. Like a line of people.

Do we have to save Warren from the... He's shooing people away. He's like, no, no, no. He's like, and he told me the most unbelievable. Never shared before stories about his relationship with his dad, how he took him to the Lionel train company in New York, and they went to the Goldman Sachs, and the CEO came out and shook his hand when he was 11 years old, and they went to a baseball game. They saw the longest baseball game in the history of baseball at Wrigley Field at that time. And now he had one mitt that his dad got him, and the whole neighbor. shared the myth.

Like, it was unbelievable. But to your point, people want to share if you ask them the right questions. Yeah, that's the power of a good question. If I would have said to him, he Warren, what stock should I buy? He would have been like, turned away from me. Yeah. But I asked him something that hit a nerve. Yes.

And there's nothing in it for you in that question. There's no agenda in that question. It's just about connection. Yeah. And people want to connect. Yeah. People want to connect. Speaking of which, I want to connect you with some books.

So let's go next to start. Let's do it. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode. Thank you.