Buckets of Rich, Attracting Luck, and Maintaining Balance — with Jesse Itzler
45:30 Share

Support for the show comes from Schwab. With Schwab Investing Themes, it's easy to invest in ideas you believe in, like online music and videos, artificial intelligence, electric vehicles, and more. Schwab's research process uncovers emerging trends, then their technology curates relevant stocks into themes. Choose from over 40 themes, buy all the stocks in a theme as is, or customize to better fit your investing goals, all in a few clicks.

Schwab Investing Themes is not intended to be investment advice or a recommendation of any stock or investment strategy. Learn more at schwab.com slash thematic investing. Support for Prop G comes from Heston's. Since 1852 and over six generations, Heston's beds have been renowned for their craftsmanship and use of high quality natural materials to help ensure your body temperature stays regulated while you sleep. Heston's offers a range of firmness options to suit different preferences and body types, ensuring personalized comfort and

The team visited a Heston sleep spa for an in-person immersive experience to try out some beds and found them to be incredibly comfy. You can visit one of their stores or go to hestons.com to book a personalized bed test or order a catalog to learn more.

Episode 306. 2006 is the year I go to belonging to the Canadian province of Saskatchewan. In 1906, Finland became the first European country to give women the right to vote. I actually sexually identify as Canadian. I'm asexual. Got it? Sort of threading the needle between dad jokes and profanity.

Welcome to the 306th episode of the Prop G Pod. In today's episode, we speak with Jesse Itzler, a serial entrepreneur, a New York Times bestselling author, part owner of the Atlanta Hawks, and an ultra marathon runner. We discuss 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, what is it, melds his professional and personal life. He's kind of an attractive person. You're sort of drawn to him. Okay, what's happening? I'm 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 going to get 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 U.S. company to be charged for violating the Digital Markets Act, which EU regulators put in place back in 2022 to prevent online gatekeepers, air quotes, from starching out competitors. It's really interesting in particular, in this particular instance. Well, I think it's interesting. Maybe you don't. Maybe you don't. Maybe you're asexual. Anyways, here's the thing.

In this particular instance, the regulators determined that Apple makes it too hard for app developers to steer consumers to alternative offerings. Well, you just figured that out. Under the Digital Marketing Act, clients can be able 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 act of God and me sacrificing my health and every relationship I had to get to $20 million in revenue. And these guys have gotten to $380 billion in revenue. What are they doing selling like a baby's kidney? What on earth are they doing over there? $380 million. $380 million.

Anyways, because of this charge, Apple says it will not roll out Apple intelligence in the EU this year. Well, they're taking their Apple and they're going home. And that's the problem with this type of regulation across capitalist democratic societies or G20 nations when we don't have a collective action. And 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 or the phone clearly don't have children. And two, there's a collective action problem. And that is 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. And it's a bit of the same thing with regulation. And that is it just strikes me as so crazy that we wouldn't get together with my idol, Marguerite Vestiaire.

By the way, quick story. You're a competitive commissioner. You're a competitiveness commissioner. I was on the Acela. I never take the Acela. I think it's dramatically unimpressive. I'm on a lot of trains in Europe, and then I get on Acela.

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 Marguerite Vestager. And it was. Sitting there meeting in between breaking up Apple and Big Tech. And I went up to her and said, could I have a picture? And she was so friendly. I don't think she has a lot of fans in the U.S., but I like her. I think she's unafraid, super smart, does her homework. Anyways, an example of a great woman.

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 joint 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 is if we had some sort of

multilateral cooperation around these things. Otherwise, it's just a race to the bottom. And I wonder if this sort of sets off a race where a bunch of big tech companies are not going to be afraid following Apple's lead to say, sorry, we're not playing your super regulation concern for the Commonwealth, you know, monopoly-powered 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.

So, okay, what would be the biggest tax cut in history? If the U.S. and China kissed and made up. China has the world's best supply chain still. India's coming up, Vietnam, Mexico, all pretty strong. China, the gangster supply chain, right? Flexible, people work hard. Quick story, quick story.

I used to run a company called L2C above, the company that I basically killed and pillaged to get to $20 million in revenue for. We did a decent amount of business in China. We didn't work for Chinese companies. I 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 Estee Lauder 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 p.m. on a Saturday night. I don't know. I'm I'm like so bass ackwards. And I called the office of the head of I think it was Estee Lauder China office.

And to tell him, I'll see you Monday at 9 a.m. It's referred or forwarded to his cell phone. He picks it up. And I said, I'm so sorry. It's Saturday night at 11 p.m. I didn't mean to wake you. And he said, where are you? And I said, I forget what hotel I was in. I think it was a higher range seat. That's a sky lobby that's like 1,100 floors into the sky. And he said, oh, you're there? He said, are you awake? I'm like, yeah, I'm awake. He said, well, I'll 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 he comes and meets you at 11 p.m.,

on Saturday so he can get a jump on his Monday morning. Think about that. Anyway, China takes themselves very seriously. And the biggest tax cut in the world would be if the supply chain and the innovation and IP of the U.S.,

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. And the more we get along and the more people who go back and forth between the China and the U.S., the 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 Kahn and Jonathan Cantor, and basically totally overfunded the DOJ and the FTC and went on a breakup lollapalooza. Why? Why?

Everything from chicken to home renovations to beef to cereal to...

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 dollar, it's probably more 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 increased.

grown dramatically, I think from something like 24 to 40 percent 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 in exchange for money. Secure platform, communication. 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 percent, but to be charging $20.

2% or 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 by the 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 Lululemon and you get to see where Lululemon 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 Lululemon dies and perhaps Lululemon's yoga pants don't get there as quickly as yours do. You see, you get my drift. 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 CapEx. 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 unleashed tremendous innovation because guess what? We had fiber. We had data. We had optics all lying fallow 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 airtightness.

Every company would begin competing for consumers, lowering their rents on companies, consumers, and parents. You'd have more innovation unlocked. Look what happened at Google. Google basically invented AI. And what do you know? They were sitting on AI until ChatGPT or OpenAI or Microsoft AI came in and said, this is a real marketplace and basically scared the shit out of Google, who was sitting on their hands. Why? Because 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. And that's what happens. There's a ton of technologies and 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 teen depression, the weaponization of the elections, the income 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's stiff in their backbone and they are starting to go gangster here. But if we don't have collective action and cross border cooperation, it's going to be a race to the bottom and we're going to end up in an even worse place with more depressed kids and.

A small number of people who make a shit ton of money, but a middle class that is struggling, labor that continues to see their wages erode, and products that never recognize their full potential because they're totally focused on monopoly abuse as a strategy as opposed to innovation. Apple was already fined $2 billion back in March for its domination in the music streaming market. That's fine. It needs another zero. These fines have become meaningless. $2 billion is nothing.

Nothing for Apple. Apple will lose or gain $2 billion in market cap in the next 10 minutes in the marketplace. We need to add a zero to all these fines. We need to go on a breakup lollapalooza. We'll be right back for our conversation with Jesse Itzler.

Support for Prop G 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 switch to Mint Mobile and you realize that you've been paying a fortune for wireless. Mint Mobile has phone plans for $15 a month after you purchase a three-month plan. You'll

Thank you.

Go to mintmobile.com slash profg. That's mintmobile.com slash profg. Cut your wireless bill to 15 bucks a month at mintmobile.com slash profg. $45 upfront payment required, equivalent to $15 per month. New customers on the first three-month plan only. Speed slower above 40 gigabytes on unlimited plan. Additional taxes, fees, and restrictions apply. See Mint Mobile for details.

Support for this show comes from the Harvard Business Review. If you're a business owner, a manager, or a boss of any kind, congrats. Must have done something right to get where you are, but I'm guessing that you still have plenty of room for improvement. Maybe you need advice on how to navigate a workplace conflict, or maybe you're wondering if AI has a place in your business. The Harvard Business Review is the place to find rigorous insight on strategy, leadership, and innovation that any professional can benefit from.

Since launching its flagship magazine, the Harvard Business Review has become a top source for rigorous insight and best management practices. And you can find the same level of expertise on hbr.org. And for just $10 a month, you can unlock unlimited access to case studies, podcasts, video series, newsletters, and articles updated daily. For me, HBR is about planes. Whenever I have a long trip, I buy an HBR.

And I typically find an article in there where I start underlying stuff and it kind of informs my management thinking, especially around HR and how to create the right incentives around a culture anyways. While much of Harvard Business Review's content is available for free after signing up at their site, subscriptions to unlimited content start at only $10 a month.

Support for PropG comes from Fundrise.

You know the adage, buy low, sell high. It's easy to say, hard to do. For example, high interest rates are crushing the real estate market right now. Demand is dropping and prices are falling, even for many of the best assets.

It's no wonder the Fundrise Flagship Fund plans to go on a buying spree, expanding its billion-dollar real estate portfolio over the next few months. You can add the Fundrise Flagship Fund to your portfolio in just minutes and with as little as $10 by visiting Fundrise.com slash PropG. Carefully consider the investment objectives, risks, charges, and expenses of the Fundrise Flagship Fund before investing. This and other information can be found in the Funds Prospectus at Fundrise.com slash Flagship. This is a paid advertisement.

Welcome back. Here's our conversation with Jesse Itzler, a 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 ended up doing what you've done. I've had a very unconventional journey. I've worn a lot of different hats. I started out

in the music business right out of college. I went to school in DC at American University. I was signed to a record label called Delicious Vinyl. That didn't go great for me. I ended up getting dropped from the label and I started doing theme songs for sports teams like the Knicks theme song, which is called Go New York Go, a bunch of other teams, and ultimately started 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 100 mile race, I discovered coconut water in 2006, 2007. Ended up partnering with a coconut water company called Zico, which we sold to Coke, Coca-Cola. And then just had a bunch of, wrote a book, had four kids, got married, moved from New York to Atlanta.

And really just followed things that I love to do and launched a bunch of businesses. Some worked and some didn't. And here I am. So let's go through, let's go through the businesses. What, what,

What was sort of your approach to starting businesses? Which ones worked? Which ones didn't? And if you could draw a line through or try and 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 idea and bring it to fruition. I think the best idea is if they don't have good leaders and good managers, then

will struggle. And, you know, Scott, I really enjoyed my twenties, man. I tried 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 sold carrot and celery sticks door to door. I was a kiddie pool attendant. I cleaned pools. I sold meat, 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 onto the private jet, it was like the scene in The Wizard of Oz when everything in life goes from black and white to 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 worked, 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, all the businesses that I've been involved with were a function of just identifying things that fit one of those two categories. You're like, wow, like I'm a runner. I would love what's the natural, healthy way to get electric, like coconut water emerged through necessity and need and just keeping my eyes open for things that would make my life easier or better.

And that's how those ideas popped into my head. So talk about Marquee Jet. What gave you the vision? I mean, it's not easy to start a... Explain the concept, how it differentiated from other fractional companies or owning a plane. And what was your niche in the marketplace? And walk us through kind of what happened there. Yeah, well, at the time that we started this company, which was around the year 2000, 1999, 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, where there are a lot of inconsistencies. Who is flying the airplane? How old is the airplane? Who's 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 NetJets was doing and FlexJet and other fractional jet 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 was a 25 hour, basically debit card. You prepay for 25 hours, put like 50 or a hundred grand down for 25 hours. And if you fly to, you have 23 hours left. You don't have to own the airplane. The plane was available on short notice.

And 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, NetJets, 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 jet card because we needed airplanes. And the CEO, Rich Santulli, threw my partner and I out of that meeting in 12 minutes and

And literally said, if you think I'm giving two 28-year-old kids who 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 repitch this next week. I'm going to set up a follow-up meeting. I want to hear more. We came back a week later and we brought in our own focus group.

And we literally set up eight chairs in the boardroom and one by one, eight people, a powerful real estate mogul from New York, a sports agent. They stood up and said they would never buy a fraction, but they would buy a 25-hour jet card. And ultimately, we got a deal to use their planes and put our program under the NetJet fleet. So our niche was catering to an audience that couldn't afford

to buy their own plane. We made private aviation more affordable to the masses, and it worked. NetJets, I would think, would 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 arm, 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 has evolved and eventually Berkshire slash NetJets bought you out, correct? Yeah. So I've been at it 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 a really...

difficult, capital-intensive business, Scott. 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 two were profitable. It's a really hard business to survive in. NetJets had 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 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 weakness is. 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 to the coconut water business at this time.

It was a very, very small category in beverage. And they said, we see this as an evolving area, but we don't buy PowerPoints. 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, et cetera, and you come in to help market it, we'd love to be in business with you.

So we went to a company called Zico Coconut Water that was doing about $2 or $3 million, maybe a little bit more in sales at the time. And we did a three-way deal. My group, my company, Zico, which existed, and Coca-Cola. And Coke had an option to buy 100% 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, um, we had a lot of celebrity investors. The old model 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 was right as a check, be an investor, Mr. And Mrs. Celebrity and help us promote it as a, as an owner of the company. And that model worked. And now a lot of, you know, a lot of companies have followed suit off of that model.

I like 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 Marquee Jet and I'd be like, I got a sale last night. We had a bell. I would ring the bell. They'd be like, what do you mean? You at the bar? Same bar I was at. I'm like, yeah, but you left at 11 o'clock. I stayed till two and I got the sale. Oh, you're 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 being there. And then you have to be good at what you do and take advantage of it. So my 20s and 30s were built around putting myself in environments where I could get lucky. So you do these Ultraman competitions, which are incredible feats of endurance. And I rode crew. And I think one of the things that's put me in a position of success is that

you know, as I'm sure, I can't even imagine what it's like to run these distances or swim 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 endure the most pain. And I've always thought that's an enormous advantage for an entrepreneur that when you think things couldn't get any worse and you just can't handle it anymore, what you learn, I would imagine in the Ultraman and what I learned at crew is that 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 and

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 100-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 leg, same build. I'm not super strong. Nothing changed. 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 supermen 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 have.

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 Marquis Jet briefly, but if they would have said to me, I was a kiddie pool attendant five years before I started Marquis Jet. I worked at a freaking kiddie pool, man. And five years later, we had this company that's doing 5 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're going to build a sales team, raise money. I would have been like, well, I said, what's the first thing, Scott, you said I needed Department of 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 the same thing with a hundred mile race or the Ultraman, or even I'm sure when you race crew going like flagpole to flagpole or tree to tree, 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 owned the plumbing supply house. We never talked about business. There was no, you know, I had to kind of help figure it out and navigate it 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. Support for Prop G comes from Greenlight. When you give your kid an allowance, you hope they spend it on enriching things like a new hobby or better yet, save it.

And you pray they're not funneling their last dollar into, say, video game skins. But no matter what, kids will never truly learn the value of the dollar until they have some cash to manage on their own. Greenlight is a debit card and money app to help them do just that. It's made for families. Parents can send money to their kids and keep an eye on kids' spending and saving, while kids and teens build money confidence and lifelong financial literacy skills.

The Greenlight app also has fun, accessible games that teach your kids how to save, invest, and spend wisely. And I mean, if they're gonna game, they might as well learn financial wisdom while they're at it.

Greenlight is an easy, convenient way for parents to raise financially smart kids and families to navigate life. Together, I've used it myself. The best endorsement I can give for Greenlight is that we are a Greenlight family and have been using Greenlight since well before they became a sponsor of Prop G. Sign up for Greenlight today and get your first month free when you go to greenlight.com slash scott. That's greenlight.com slash scott to try Greenlight for free. greenlight.com slash scott.

Support for PropG comes from LinkedIn Jobs. Finding a great new hire is impossible if you're searching in the wrong place. Traditional job boards might have been the only game of 10 for a while,

But today's business owners need a platform with more robust features and a broader reach, a platform like LinkedIn Jobs. We recently posted an opening to LinkedIn Jobs and we got a bunch of candidates. Some even felt fairly qualified, which is good news. And it's not that expensive. With LinkedIn Jobs, you can connect with qualified professionals you won't find anywhere else.

And according to LinkedIn, 86% of small businesses find a qualified candidate within just 24 hours of posting. So if you're not looking for your next hire on LinkedIn, you might be looking in the wrong place. Hire professionals like a professional on LinkedIn. Post your job for free on LinkedIn.com slash prof. That's LinkedIn.com slash prof to post your job for free. Terms and conditions apply.

Support for this show comes from AWS. We all know that AI is here and isn't going away anytime soon. And companies now are looking to break new ground in this space. It's the reason why AWS is doubling down on their investment in generative AI startups. By committing $230 million to accelerate AI startups and launching their new generative AI accelerator program, AWS is helping startups turn groundbreaking ideas into the future of technology. More

More than 80% of unicorn companies are already customers of Amazon Web Services, companies that are valued over a billion dollars.

The goal of this program is to enable startups to build generative AI applications that change nearly every industry. This program will look to accelerate the development of emerging generative AI startups from around the world. Out of thousands of applicants, AWS will select 80 of the most promising startups to receive up to 1 million in AWS credits and the resources they need to shape the future of AI. Learn more and apply before July 19th at startups.aws.com.

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, intellectually rich, purposefully rich, physically rich, and adventure rich. Can you walk us through those? Yeah. There's an old acronym that they use. As my parents were getting older, I did a lot of research around senior facilities and

but I'm going to send my parents to a senior facility. And I stumbled upon an acronym that one of the centers used called SIBS. And it stands for social, intellectual, physical, purposeful, and spiritual. And what struck me as so interesting about that is that they didn't talk about Instagram followers, how many do you have, or the watch you wear. 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, and even myself. I'm like, what, what are those buckets that I value the most?

and they're the ones that you just said. You can have all the money in the world, but if you're not time rich, having the freedom to do what you want to do, or spiritually rich, then there's an emptiness to your wealth. So that's sort of how I started to think about it. 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 for me to measure my success. You know, my family, I have four kids, my friends, my relationship, my business, my wellness, et cetera. How am I doing in those buckets? What do you think about, I've always, I like the saying, you can have it all, you just can't have it all at once because the time bucket is,

I have found, or 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, we're just going to know what the term is, run especially full or especially empty, right?

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. It came at a price to my relationships. I 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 now.

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 that sometimes are in opposition with each other?

Well, it's an individual decision. I think it varies depending, in my opinion, based on your age. So I think that I believe it was important to have your 20s. 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. They were sacrificing life. They gave up their 20s. You know, your 20s are a time

to try as many things as you can and see what you like to do and see what you're good at. And then, you know, and then master it in your 30s and get rich in your 40s. You're going to make five to 10 times as much money, most people in their 40s and 50s than you will in your 20s. There's exceptions, but because you're going to be smarter, you're going to know more people, you're going to be better at 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.

And you can't compare yourself to that. There are people that do that. But I remember going to Coca-Cola in my 20s 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 remembered that. And it's gotten sped up a little now with the internet and everything. But it takes 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 do I want to spend at work and how much time do I want to spend with my kids?

Do you have any sort of guideposts as a dad to try and make sure that you – I mean, because I'm telling you, your kids, you're in the golden decade right now. You're in the midst. 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'd call the golden decade, sort of 4 to 14. Yeah.

And I sort of knew it. I mostly knew it, but I wish I'd known it more and it imposed more rules on myself. Do you impose any sort of rules 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-life balance is way out of whack. So rule number one for me is I'm never too tired for my kids.

I have a lot of rules. I mean, a new one that I just did has 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, the old me 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 been a big switch. I have a lot of guardrails 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 are the most, 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 regularly.

as much as we can. We don't say, well, we're going to do it 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 of 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 in this. Um, if we have anything that we want to talk about, like summer plans or goals or whatever, we'll bring it up. It's a chance for everybody to kind of share, get up to speed.

and like communicate um in a group setting sometimes you can 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 scott it allows everybody to be heard i 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 their, 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've 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 talked about what do we want to feed our kids? Do we want our kids to go to temple or church or our religion? Like what does religion come into play? And, um, you know, where do 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, um,

You have to eat. I eat super healthy. Sarah eats like the other end of the spectrum. How would 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 are you 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, but like, I love watching how hard you work on the field. Like, it's just, I love how much, you know, how you hustle today. Praising the effort is a big thing. We try to expose our kids to as many life experiences, different people as we can.

And so it sounds like you have a healthy relationship with your partner, good kids. You've obviously checked a lot of boxes as an entrepreneur. 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 have liked to have done or accomplished that I haven't done or accomplished already? 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 and 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 even talked about this, but I feel like I haven't really figured out

exactly like what, like that big thing I'm, 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, uh, my sister had been living with my mom because, uh, my dad, when my dad died, my sister moved into her house and she would walk her to bed every night. And the night of mother's day, um, on the way to going to bed at like 11 o'clock, my sister, my mom stopped my sister and said, um, her name is Jana, my sister. She said, Jana, get the nicest, um,

glass, glassware that we have and get a bottle of champagne. So my 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 drank, 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 your

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 know what that looks like for me. It's a nice way to go. 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,

I mean, obviously it's got to impact you emotionally, but has 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. I plan most of my year in advance. I have this big calendar. I put as much of 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. 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 used to really spend a lot of energy on just bounce off me. And if you could give your 25-year-old self...

Say you had maybe 15 or 30 seconds with them. You find the time machine, that's the good news. The bad news is you only have 15 or 30 seconds with your 25-year-old self. What would you say to him? I would probably say a quote that Gandhi had that I lived by, which is, learn like you'll live forever and live like you'll die tomorrow. I would tell my 25-year-old self to learn, experience as much as you can, do as many things as you can,

with the hope that those experiences will help you all the way down the line, but also live like you'll die tomorrow.

Jesse Itzler is a serial entrepreneur, a New York Times bestselling author, part owner of the Atlanta Hawks, and an ultra-marathon runner. Most notably, Jesse sold his private jet company, Marquis Jet, to Berkshire Hathaway and his Zico coconut water brand to Coca-Cola. His bestselling books include Living with a Seal and Living with Monks. He joins us from his home in Atlanta. By the way, how did Atlanta happen? We didn't go there, Jesse.

Well, I was a New Yorker for 25 years. I met my wife. My wife was a customer of mine at Marquee Jack. That's where we met. And when we got engaged and we're dating, her business Spanx 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 Spanx was way more important than what I was doing. And I moved down to Atlanta. We never moved back. All right.

I always say around big decisions, I'm 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 Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from the Vox Media Podcast Network. We will catch you on Saturday for No Mercy, No Malice as read by George Hahn. And please follow our Prop G Markets Pod. Again, that's the Prop G 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 Prop G Markets Pod.