Buckets of Rich, Attracting Luck, and Maintaining Balance — with Jesse Itzler - podcast episode cover

Buckets of Rich, Attracting Luck, and Maintaining Balance — with Jesse Itzler

Jun 27, 202446 minEp. 306
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Jesse Itzler, a serial entrepreneur, a New York Times bestselling author, part-owner of the Atlanta Hawks, and an ultramarathon runner, joins Scott to discuss his approach to entrepreneurship, including how it aligns with his fitness journey, and the strategies he implements to maintain balance in his life.  Follow Jesse on Instagram, @jesseitzler.  Scott opens with his thoughts on the EU’s antitrust crusade against Big Tech and why he believes breakups oxygenate the economy.  Subscribe to No Mercy / No Malice Buy "The Algebra of Wealth," out now. Follow the podcast across socials @profgpod: Instagram Threads X Reddit Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Sort of threading the needle between dad jokes and profanity. Go, go, go! Welcome to the 306 episode of The Prop Cheapod. In today's episode, we speak with Jesse Itzleris, your launchman, a New York Times best-selling author, part owner of the Atlanta Hawks and an ultra marathon runner. We discussed with Jesse his career journey, his approach to entrepreneurship, including how it aligns with his fitness journey, and the strategies he implements to maintain balance in his life.

I've seen this guy everywhere on TikTok because he has sort of a nice vibe that sort of melds his professional and personal life. He's kind of an attractive person who's sort of drawn to him. Okay, what's happening? Back in London after a week in the South of France, that's right. It is about 75 degrees. By the way, there's no air conditioning in the UK.

Did you know that? They don't believe in air conditioning. We do have indoor plumbing. I'll give them that. There's no fucking air conditioning. I get up last night because I'm hot because it's gotten up to a sweltering 72 degrees here. I'm like, I'm a little bit warm. I'm going to turn on the air conditioning. I'm looking for the air conditioning and I was looking for a long time. Why because there is no air conditioning? What's with that?

Anyways, moving on to some news. Apple became the first US company to be charged for violating the digital market's act, which EU regulators put in place back in 2022 to prevent online gatekeepers, air quotes from starting out competitors.

It's really interesting. In particular, in this particular instance, well, I think it's interesting. Maybe you don't. Maybe you're a sexual. Anyways, in this particular instance, the regular is determined that Apple makes it too hard for app developers to steer consumers to alternative offerings. Will you just figure that out under the Digital Marketing Act?

Bines can be up to get this 10% of gross revenue for Apple. That would be up to 38 billion based on last year's revenue. Okay, let me get this. Apple makes $380 billion. How is that even possible? How is that even possible? I sold my last company for 160 million. It was doing 20 million in revenue. It literally took an active God and me sacrificing my health and every relationship I had to get to 20 million in revenue.

In these cases, I've gotten a $380 billion in revenue. What are they doing? Selling like a baby's kidney. What on earth are they doing over there? $380 million? Anyways, because of this charge, Apple says we'll not roll out Apple intelligence in the EU this year.

They're taking their Apple and they're going home. That's the problem with this type of regulation across capitalist democratic societies, or G20 nations, when we don't have a collective action. It's the same problem that haunts parents with their teens with respect to depression and social media.

People who say, well, can't you just take away the social media of the phone? Clearly, don't have children. There's a collective action problem. If your kid's not on snap and all the other eighth graders are on snap, that kid actually is more depressed because he or she is ostracized or feels isolated.

It's a bit of the same thing with regulation. It just strikes me as so crazy that we wouldn't get together with my idol, Migrate Vestio. By the way, quick story. Your competitive commissioner, your competitive commissioner was on a train from I was on the Assella. I never take the Assella.

I think it's dramatically unimpressive. I want a lot of trains in Europe and then I get on the Assella and I think, well, maybe we are going to maybe it is the peak of our, I don't know, society or peak America. Anyway, and I saw this woman knitting and I'm like, that looks like Margarita Vestio.

It was sitting there meeting in between breaking up Apple and Big Tech. I went up to her and said, could I have a picture? She was so friendly. I don't think she has a lot of fans in the US. But I like her. I think she's unafraid, super smart. Those are homework. Anyways, an example of a great, a great regulator.

But they're saying they're not going to roll out intelligence. So they're going to take it home. And the problem with not having collective action or join regulation is that these big tech companies as a group have now become more powerful than any specific country, maybe even the European Union. We'll see, we'll see.

And they're not afraid to say no, this is more than them saying we don't want to comply. They're saying if you start regulating us, we don't want to play ball. And I think that where we would be best served as if we had some sort of multilateral cooperation around these things.

And so, in other words, it's just a race to the bottom. And I wonder if this is sort of sets off a race where a bunch of big tech companies are not going to be afraid following apples lead to say sorry we're not, we're not playing your super regulation concern for the Commonwealth, you know monopoly power games. Microsoft is also facing charges for anti competitive behavior.

Regulators do not like that the firm bundles its teams app with the office suite, Microsoft hasn't seen this type of antitrust in more than a decade. So, okay, what would be the biggest tax cut in history. If the US and China kissed and made up. China has the world's best supply chain still India is coming up Vietnam, Mexico, all pretty strong China, the gangster supply chain right flexible people works out quick story, quick story.

Super on a company called Altus above the company that I'm basically killed and pillage to get to 20 million in revenue for. We did a decent amount of business in China, we didn't work for Chinese companies have found Chinese companies don't want to pay for anything. They'll figure. But American companies looking to get into China would hire us to look at Chinese data around their digital footprint. And one of my clients, I think it was est a lot of China, they made a big bet on China.

And I was doing a swing through China to do events and I get there like 11 PM on a Saturday night. I don't know I'm I'm so bass aqua and I called the office of the head of I think was a state lot of China.

And to tell him I'll see you Monday at 9 AM. It's referred or forward to do a cell phone. He picks it up and I said I'm so sorry it's Saturday night of the PM. I didn't mean to wake you and he said, where are you? And I said, I forget what I was on the high reins. See it as a sky lobby that's like 1100 floors in the sky.

And he said, Oh, you're there. He's there. You wake him. Yeah, I'm a way. He said, Well, come over right now. That's fucking China. That's when I'm like, Oh, God, these people take themselves pretty seriously.

You call the head of Estee Lauder China and it comes in me to 11 PM on Saturday. So we can get to jump on his Monday morning. Think about that. Anyway, China takes themselves very seriously in the biggest tax cut in the world would be if the supply chain and the innovation and IP of the US got back together.

What do we have? We have an inflation problem. What do they have an unemployment and growth problem? Boom. Let's kiss and make up ladies and gentlemen in the more we get along and the more people who go back and forth between the China and the US less likely we are to go to war with each other.

The less likely they are, I believe to invade Taiwan, the less likely we are to start shooting or entering into a hot war with their navy. If and when they invade Taiwan, if we're all making a lot of money and interacting and speaking to each other, the second biggest tax cut in history, the second biggest tax cut would be if we invested $10, $20, $30 billion gave it to Lena Conn and Jonathan Cantor.

And basically totally overfunded the DOJ and the FTC and went on a breakup, Lala, Paloza. Why? Everything from chicken to home renovations to beef to cereal to confections to search engines to social media is controlled by a small number of companies. And what happens to an industry when it becomes too concentrated, they learn that they don't have to make great products, they can just raise prices and there aren't that many options and then boom, what happens?

Prices go up and the traditional means of establishing anti-competitive behavior is to look at prices, but how do you establish those metrics around companies that offer their products for free? Well, what happens is Amazon becomes a monopsony. And that is if you want to be on the Amazon platform and have access to 50 cents on the e-commerce dollars, probably not like 70, if you take out groceries and gasoline, you have to be on their platform.

And what do you know, the fees they charge, their retailers on the third party platform have grown dramatically, I think from something like 24 to 40% in the last decade. Okay, that is monopoly abuse. And what do you know? What do you know? How would you describe the Apple App Store, provide security, technology, you know that the people on the other end are going to provide a service and exchange for money, secure platform, communicate with them.

And then you have a platform, communicate, oh, wait, it's a credit card company. What do we need? What do we need? We need that Apple App Store, not to be charging 30% but to be charging to where 3% like every credit card company, but they get away with 30% why? Why?

Because they have a monopoly on essentially people who spend money online. This would be like you own the train tracks and you own the trains and you see where apparel is being dropped off and you use that data to go into your own apparel business.

And in a way, you don't charge your own owned and operated apparel company any transit fees and they can charge lower fees and no one can compete with them because you start a line of athletic wear or yoga wear and it costs half as much as Lulu Lemon and you get to see where Lulu Lemon is selling and you have your store called Apple Lemon and you charge half the price and you can still make money and you just wait until Lulu Lemon dies.

And perhaps Lulu Lemon's yoga pants don't get there as quickly as yours do you see you get my drift you get my drift so the fastest way to lower taxes on consumers globally would be to go in to the three or four biggest companies in every major category and break them up and oxygenate the economy similar to when we broke up AT&T. What were the arguments?

Well, we need to be big so we can invest in phone lines and catbacks. Okay, we've heard that before we're good people and it's a good brand and we're going to buy off a bunch of politicians boom.

They go and they break it up seven baby bells each of those companies worth more than the original AT&T within 10 or 12 years. Oh, and by the way, what did we have we at least tremendous innovation because guess what we had fiber we had data we had optics all lying follow at Bell Labs and they didn't want to compete with their own technology.

This would be the most dramatic tax cut in history second only to China and that is every company would begin competing for consumers lowering their rents on companies consumers and parents. You'd have more innovation on like what happened at Google Google basically invented AI and what do you know they were sitting on AI until chat GPT or open AI or Microsoft AI came in and said this is a real a real marketplace and basically scared the shit out of Google who was sitting on their hands.

And they didn't want to challenge search so they kept it kind of on the low down they didn't really go hard at it. That's what happens. There's a ton of technologies innovation waiting to be unleashed if we break these companies up the EU is taking action ahead of us recognizing they get the majority of the downside they get all the team depression the weaponization of elections and inequality.

The monopoly abuse but they get a fraction of the upside there aren't that many hospital wings or universities named after Google or Facebook billionaires like fuck that that's that stiff in their backbone and they're starting to go gangster here but if we don't have collective action across border cooperation it's going to be a race to the bottom and we're going to end up and even worse place with more depressed kids.

All number of people who make a shit ton of money but a middle class of the struggling labor that continues to see their wages a road and products that never recognize the full potential because they're totally focused on monopoly abuse is a strategy as opposed to innovation Apple was already find 2 billion back in March for its domination in the music streaming market that's fine and needs another zero these finds have become meaningless 2 billion dollars is nothing nothing for Apple Apple will lose or gain 2 billion dollars market cap in the next 10 minutes.

In the marketplace we need to add a zero to all these finds we need to go on a breakup law of Paloza. We'll be right back for our conversation with Jesse it's lure. Support for property comes from mint mobile have you ever given your house a good deep clean and then thought to yourself wow how have I been living like this that's the same feeling you might get when you switched a mint mobile and you realize you've been paying a fortune for wireless mint mobile has phone plans for

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This and other information can be found in the funds perspective at fundrise.com slash flagship. This is a paid advertisement. Welcome back here's our conversation with Jesse it's their serial entrepreneur best selling author and ultra marathon runner. Jesse where does this podcast find you? Atlanta Georgia where I live Atlanta nice so let's bust right into it give us your kind of origin story Jesse walk us through.

Your background and how you end up doing what you've done I've had a very unconventional journey and want a lot of different hats I started out. In the music business right out of college on school in DC and American university I was signed to a record label called delicious final and that didn't go great for me ended up getting draft from the label and I started doing things on for sports teams like the next thing song called go New York go.

I started a bunch of other teams and ultimately started a like a music marketing company that I sold to a public company and then I'm a big runner I've done a lot of long distance ultra races and when I was training for a hundred mile race I discovered coconut water in 2006 seven ended up partnering with a coconut water company called Zico which we sold the coke Coca Cola.

I just had a bunch of wrote a book had four kids got married move from New York to Atlanta and really just follow things that I love to do and launch a bunch of businesses some work in some day and here I am.

So let's go through let's go through the businesses what what we started your approach is starting businesses which ones worked which ones didn't and if you could draw a line through or trying to find signal from the noise in terms of why companies worked or didn't work what would that signal be. Well jumping right to that point I think at the end of the day usually for me it's come down to management and that's not hiring people that could take my day bring it to fruition.

I think the best ideas if they don't have good leaders and good managers will struggle and you know Scott I really enjoyed my twenties man I try to a lot of different things I slept on 18 different couches from 18 to 22 different friends putting me up going couch to couch trying different.

Businesses I call I sold Karen celery sticks door to door I was a kiddie cool attendin I clean pools I sold me chicken door to door I just tried so many different things when I was 28 years old I was a guest on a private jet. And when I walked on to the private jet it was like the scene in the Wizard of Oz when everything in life goes from black and like the color.

And I was like people fly like this this is insane I want to fly like this and that's how we got the idea to start this company called marquee jet I think a lot of the businesses that I've been involved with some which works many more which didn't work entrepreneurs can do two things they can make something better or they create something new.

And they were all the businesses that I've been involved with were a function of just identifying things that that one of those two categories either like wow like I'm a runner I would love what's the natural healthy way to get election like coconut water emerged through necessity and need and just keeping my eyes open for things that would.

Make my life easier better and that's how those ideas popped into my head so talk about marquee jet what what gave you the vision I mean it's not easy to start of explain the concept how differentiated from other fractional companies are owning a plane and what was your nation of marketplace Marcus who kind of what happened there.

Yeah well the time that we started this company which is around the year 2000 99 2000 there were really only three ways to fly privately you could buy your own airplane which was incredibly expensive you could charter a plane with their all out of inconsistencies who is flying the airplane how old is the airplane is managing the airplane.

Or you could buy a fraction of an airplane which also is a long term commitment and a lot of money that's what net jets was doing and flex jet and other fractional jack companies and I couldn't afford any of those options and they weren't realistic for me I wanted to take two or three flights a year with some friends treat my parents maybe a business trip so our idea is a 25 hour basically debit card you prepay for 25 hours put like 50 or 100 grand down for 25 hours and if you fly to you.

You have 23 hours left you have to own the airplane the plane is available on short notice and we you're right we had no aviation experience and we had no airplanes and we had no money but we went to the 800 pound gorilla net jets which had 650 planes the largest private jet fleet in the world and owned by Warren Buffett and we pitched them this idea of a 25 hour jack card and because we needed airplanes and they the CEO would send.

To my partner and I out of that meeting 12 minutes and literally said if you think I'm giving to 28 year old kids who didn't break probably didn't break a thousand on their SATs access to my planes that's not going to happen and kicked us out and the president grabbed us and said you know wait a second I think there's something here I want you guys to come back and repish this next week I'm going to set up a follow up meeting I want I want to hear more we came back a week later and we brought in our own phone.

I don't focus group and we literally set up a chairs in the board room and one by one eight people a real powerful real estate mogul from the York sports agent is stood up and said they were never by a fraction but they were by a 25 hour jack card and ultimately we got we got a deal to use their planes and put our program under the net jet fleet.

So on it was you know was catering to an audience that kind of afford to buy their own plane we made private aviation more affordable to the masses and it worked. Netchets I would think we want to do it in hopes that they could get people addicted to this and then move them up to fractional is that accurate. That's 100% accurate we were a marketing on and yes we were a farm system for their larger fractional program.

And so tell me about the industry now in terms of fractional how would you differentiate between kind of give us a lay of the land and how the market that business is evolved and eventually. Berkshire slash netchets about you out correct. Yes I've been added for almost 13 years now so I don't follow the industry super close I'm just a customer.

But I know a lot it's really it's a really difficult capital intensive business got I think when we started there were like 50 companies that put a flag in the ground that said they were in the private jet space and like to were profitable. It's a really hard business to survive in netchets at the at the luxury of having you know being backed by Berkshire so they built an incredible infrastructure.

But now you know 13 years later I'm not 100% sure how it's evolved but it's a lot of the same it's still caught by your own plane travel you know by a fraction of a plane charter or some kind of card or one off program and give us the journey around coconut water.

So my models I'm not a great operator I know what my weaknesses I'm a terrible operator a much better marketer idea guy and following piggybacking off of that model where like wow I can come up with an idea and partner with a company that has an expertise and I could just be a marketing arm for them.

I went to Coca Cola with this idea for coconut water and a PowerPoint and said I want to get coconut water business at this time it was a very very small category and beverage and they said we see this as an evolving area but we don't buy power points. But if you find an existing company out there that's proven that they can source the product sell the product they're on the shelves etc and you come in to help market it we love to be in business with you.

So we went to company called Zico coconut water that was doing about two or three million dollars maybe a little bit more in sales at the time and we did a three way deal my group my company.

Zico which existed in Coca Cola and coca an option to buy a hundred percent of the company down the road and two years later they executed that option so we got it really hot really fast and we did that through PR through we had a lot of celebrity investors the old model and in beverage was we're going to pay people as endorsers but the customers consumers pretty smart now and they they see that our model.

What is the way that you define or you view success and luck what has been your approach to putting yourself in situations where luck can find you.

Well I think as an entrepreneur a big part of it is luck and I've been super lucky and probably way more lucky than good but I put myself in situations where I can attract that luck I used to come home Scott from like you know I walk into Marquis Jen I'd be like I got a sale last night we had a bell I would ring the bell they look what you need you at the bar same bar I was that I'm like it but you left it 11 o'clock I stayed till two.

And I got the sale all you so lucky the guy came I was I'm not lucky I put myself in that situation you know luck doesn't happen Sunday night watching the Kardashians on your couch it happens when you put yourself in an environment where the universe can reward you for here and then you have to be good at what you do and take advantage of it so my twenties and 30s were. Built around putting myself in environments where I could get lucky.

So you do these ultimate competitions which are incredible feats of endurance and I wrote crew and I think one of the things that put me in a position of success is that you know as I'm sure I can't even I can't even imagine what it's like to run these distances or some these distances but.

In crew it's basically who can endure the most pain I mean there's some technique there's some strength there's some fitness but it's mostly an exercise and who's willing to enjoy the most pain and I've always thought that's an enormous advantage for an entrepreneur that when you think things couldn't get new worse and you just can't handle it anymore what you learn I would imagine in the in the ultra man and what I learned a crew is it when you think that it means you're about a third of the way to your limit and it always gave me a sense of comfort and confidence that I could keep going.

I'm curious what you think the relationship is between kind of what I'll call extreme fitness or extreme sports and entrepreneurship. In 2006 I ran my first hundred mile race and when I came back after that race I got my office together and I said double the business plan.

The correlation I mean when you do something like that you realize that the limits that we put on ourself are pretty much self imposed and we have so much more in the tank than we thought we could I mean I started out running two miles that was my goal and nothing changed on my body I'm still the same legs same build I'm not super strong nothing change the only thing that changed is I saw someone run a hundred mile race I went to watch a hundred mile race.

In 2006 and there weren't a bunch of Superman that started at the starting line people in fact weren't even that physically impressive but what happened was they didn't stop. They didn't they just didn't stop and I was like oh wow this is a test of will this is just will sign me up for this race and let me see how much will I had and when I did the first hundred mile race it changed everything in my life.

As it relates to entrepreneurship now for starters we talked about marquee jet briefly but if they would have said to me I was a kitty pool attended five years or started marquee jet I worked at a freaking kitty pool man and five years later we had this company that's doing five billion in sales and if they would have said to me when I started marquee jet you need department of transportation approval you need FAA approval you can have built the sales team raise money.

I would have been like what's the first thing Scott you said I needed the partner transportation approval there's got to be a lawyer that does that let me find that guy okay we got what's the second thing I need FAA approval and I broke it down into digestible bites it's just anything with a hundred mile race or the ultra man or even I'm sure when you race crew going like flagpole the flagpole or treat a trade.

You know you break it down into digestible bites so there's a lot of similarities between how you approach a race like that and how you approach a startup business especially if you have no entrepreneurial experience my dad on the plumage supply out we never talked about business there was no you know I had to kind of figure it out and then navigated on my own which actually became a blessing because it meant that I would do things differently than other people. We'll be right back.

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You talk about the buckets of rich that you believe in and I love that term buckets of rich time rich socially rich spiritually rich and actually rich purposefully rich physically rich and adventure rich. Can you walk us through those? Yeah, there's an old acronym that they use is my parents were getting older I did a lot of research around senior facilities.

I'm going to send my parents to a senior study and that's some of the prime an acronym that one of the centers used called SIPS and it stands for social intellectual physical purposeful and spiritual. What struck me is so interesting about that is that they didn't talk about Instagram followers how many do you have a watch the watch you wear. The car like financial wasn't even a category.

And they're grading your overall like half the most important thing your health you know your wellness your happiness so I started to like think about. My own circle of friends and people that are wealthy or and even myself and like what what are those buckets that I value the most. And they're the ones that you just said like you know you can have all the money in the world but if you're not time rich. How you know having the freedom to do what you want to do.

Or spiritually rich or you know then there's an emptiness to your wealth so that's sort of how I started to think about it you know I invest a lot in how I spend my time how I plan. How I think about time being as good as I can be in the buckets that matter the most to me. It's a really good way to me to measure my success you know my family I four kids. I friends my relationship my business my wellness etc how am I doing in those buckets.

What do you think about I've always I like to say you can have it all you just can't hold it all once because the time bucket. I have found at least I found that if I wanted to have the money bucket full at some point I'd have to sacrifice the time bucket that I'd have to pretty much go all in on work for a certain amount of time. That certain buckets were just going to know what the term has run run especially full or especially empty.

You know I was never able to really strike a balance as a younger man and achieve any level of success I know those people existed I wasn't one of them I found I had to go all in on something. Or it just didn't work and it came at a price you know it came at a price of my relationships I wasn't you know it was worked out but I probably wasn't as fit as I could have been or healthy as I could have been.

But now I have a lot of that balance I have a thesis and that is young people think they can have it all and I just don't think that's true what are your thoughts about trying to manage balance at a young age and you know all of these different buckets sometimes are in in opposition with each other.

Well it's an individual decision I think it it varies depending in my opinion based on your age so I think that I believe it was important to have your twenties I saw a lot of my friends go from 20 to 50 like that because they were working on Wall Street in front of a computer all day it they were sacrificing life they gave up their twenties you know the twenties are a time to try as many things as you can and see what you can do and see what you're good at.

And then you know and then master it in your thirties and get rich in your forties you're going to make five ten times as much money most people in their forties and fifties then you will in your twenties there's exceptions well but because you're going to be smart you're going to know more people you're going to be better what you do and I think a lot of people see on social media people getting wealthy quickly and think like well that's their story.

You know and you can't compare yourself to that there are people that do that but I remember going to Coca-Cola in my twenties with on the Zico meeting and the president of coke said to me it's going to take eight years to build this brand it takes eight years to build a brand in this country I always remember that and it's gotten sped up a little now with the internet and everything but it's your time.

So I think look balance is tough you always go I wasn't in balance when I ran my ultra marathon I was training you go in and out of balance but that sacrifice and what you're willing to give up is important to remember you don't get your twenties back you don't get your thirties back you don't get your kids growing up back I have four kids now that are all under the age of 14 so I'm going through this right now how much time go I want to spend at work and how much time go I want to spend with my kids.

What do you do you have any sort of guide post as a dad to try and make sure that you I mean because I'm telling you those your kids you're in the golden decade right now you're in the midst of those are literally the best years and everybody says that they're all great but I don't buy that I think some years are better than others and you're in what I call the golden decade sort of four to 14 and I sort of knew it I mostly know it but I wish I'd known it more and it imposed more roles on myself do you impose any sort of role in the world.

I'm going to impose any sort of roles other than trying to spend time with them. Yeah I have a rule I'm never too tired for my kids so if my kids want if I come home and my kids might have a baseball catch and I'm exhausted I'm still having the baseball catch because if I'm too tired when my kids want me then my work like balance is way out of wax so rule number one for me is I'm never too tired for my kids.

I've got a lot of a lot of rules I mean a new one that I just did is nothing to do with time but when my kids come into my room if I'm on my phone this is my office my phone is my office I don't go to an office this is my office so when my kids come in if I'm on my phone I would say I would say give me one second guys let me just finish this up the new me puts my phone down so my kids know that they're more important than my phone so that's a big switch I have a lot of

hard rails around when I use my phone so phone time at home and all that said my kids also know that mommy comes first like I've been told my whole life your kids come first they don't like mommy and daddy have to be right or nothing's right so you know it's important for Sarah my wife and I for our kids to know like you know mommy and daddy come first and then I'm a big show

don't tell you know like I include my kids we have family dinners as much as we can we don't say well we do four times a week as often as we humanly possibly can we have family dinners and we talk about a lot of things we try to expose our kids to a lot of things and we ask them to share a lot of things we have family meetings once a week so we invest a lot in the family unit can you describe if it's not too personal

I love the idea of a family meeting but I'm not entirely sure how what's supposed to happen I'm just curious give us a sense what happens in your family meeting yeah so we get together and on Sundays and it's short and we just talk about something like one thing that happened to us this week so I said you know in school I failed at this I did this I succeeded this if we have anything that we want to talk about like summer plans or goals or whatever will bring it up

it's a chance for everybody to kind of share get up to speed and like communicate in a group setting sometimes vote if it's like hey you know we're thinking about going on a trip this year what you know that kind of stuff gets discussed you know what it does

that allows everybody to be heard actually like it and I'm not a great communicator so for me it's not it's kind of challenging but the other rule that we have is when we have guests at our dinner table each of the kids has to ask the guest a question about them so it gives them a chance to practice there what I think is the most important thing which is communication and public speaking so that's another kind of rule that we have

so we talked a little bit about fathering what advice would you give to a young man who's just entering into a relationship and thinking about getting married what do you know now that you wish you'd known earlier in your marriage well in my marriage before I got married we never talk about what do you want to feed our kids we want to

temple or church or are religion like what is religion come into play and you know when we want our kids to go to school private school public school how are we going to you know discipline our kids what's our philosophy on discipline like that never crossed my mind to talk to Sarah about until we had kids you have to eat

I eat super healthy Sarah eats like the other end of the spectrum how do you want to raise our kids so like we never had those conversations and so that's just something to think about if you're getting married like how aligned are you on certain things and definitely how

aligned the on your values or whatever as far as parenting you know we try to praise the effort as much as we can and not the result so Charlie you know not oh you scored three touchdowns like I love watching how hard you work on the field like it's just I love how how much you know how you hustle today praising the effort is a big thing we try to expose our kids to his many

many life experiences different people as we can and so you it sounds like you have a healthy relationship with your partner good kids you've obviously checked a lot of boxes nonchalant or what what what's left for you what are you working on if you look out 10 years and you think this is really what I would like to have done or accomplished that I haven't done or accomplished already what what is that or those things

I feel like I'm finally at 55 I'm turning 56 in August in the right lane I do a lot of singing coaching and I like it I feel like I'm good at it I have a lot of experiences to share and I just share my experiences in business and being a dad all that stuff but I also feel like I haven't I never really talked about this but I feel like I haven't really figured out exactly like what like that

big thing I'm so I've done big things but the big thing I'm supposed to do to really contribute like to the world I don't think I've even hit that yet so I my eyes are always open for it I just don't I don't know I lost my dad my mom and my sister in the last two years so it's changed my perspective a lot on a lot of different things you know like what just like what matters the most to me when my mom my mom died a month ago

and the night she my sister had been living with with my mom because my dad when my dad died my sister moved into her house where and she would walk her to bed every night and the night of mother's day on the way to going to bed at like 11 o'clock my sister my mom stopped my sister and said

her name is John on my sister so John get the nicest glass glassware that we have and get up all the champagne so I'm sister got the glass you know like the nicest glasses in my mom's house they poured a glass of champagne and they made my mother's even drink they made a toast and she never woke up

so like she like basically toasted her life on the last night of her life which is amazing but I think like when I think back to that like to live a life that you can toast I don't know what I'm going to do in 10 years I have no idea but if I had the last glass of champagne tonight I mean I'm toasting to an insanely amazing life already so you know it can only get better I think but I don't I don't know what that looks like for me.

So I swear to go it's it's unusual it's as if your mother knew that that was it yeah it was unreal and having experienced that kind of loss in such a short concentrated time period as it I mean obviously it's got to impact you emotionally but is it impacted you in terms of how you approach relationships or what you're thinking about professionally or how you spend your time.

Yeah I mean I've always been good with spending my time like I said I invest a lot in planning really I plan most of my year in advance I have this big calendar I put as much as the things that I want to do in advance before I plan my work I plan my life

trips races blah blah blah blah one on one trips with my kids so like and then I just kind of follow the script but I think that what's changed is just a lot of the small things that I would used to like really spend a lot of energy on I just bounce off me.

And if you could give your 25 year old self you know say you had maybe 15 or 30 seconds with them right you find the time machine that's a good news the bad news is the only a 15 or 30 seconds with your 25 year old self what would you say to him. I would probably say it quote that Gandhi had that I live by which is um learn like you live forever and live like you died tomorrow I would tell my 25 year old self to like learn experience as much as you can do as many things as you can.

But the hope that those experiences will help you all the way down the line but also live like you died tomorrow Jesse it's there is a serial entrepreneur a New York Times best selling author part owner of the Lanah Hawks and an ultra marathon runner most notably Jesse sold his private jet company marquee jet to Berkshire halfway and his Ziko coconut water brand to Coca Cola his best selling books include living with a seal and living with monks he joins us from his home.

In Atlanta by the way how did Atlanta happened I we didn't go there Jesse I was New Yorker for 25 years. I met my wife my wife was a customer of mine at marquee jet that's when we met and when we got engaged and we're dating her business banks was based in Atlanta and we were splitting our time and then we had a kid and we're like we got to pick and the spanks was way more important than what I was doing and I moved down to Atlanta. I never move back.

I was there on big decisions on an influencer not a decision maker and influencers being generous anyways Jesse I really enjoyed this conversation best to you and yours. This episode was produced by Caroline Shagrin Jennifer Sanchez is our associate producer and true boroughs is our technical director.

Thank you for listening to the property pod from the box media podcast network we will catch you on Saturday for no mercy no malice as you're read by George Han and please follow our propgy markets pod again that's the propgy markets pod and subscribe wherever you get your pods for new episodes every Monday and Thursday you won't get these episodes unless you subscribe to the propgy markets pod.

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