The Learning Leader Show With Ryan Hawk - 699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money

Episode Date: August 2, 2026

The Learning Leader Show with Ryan Hawk www.LearningLeader.com This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Jack Raines is a writer and investor. At 24, he quit his corporate finance job at UPS, bought a one-way ticket to Barcelona, and spent the next year traveling through 25 countries while writing a newsletter that grew to hundreds of thousands of readers. He went on to earn an MBA from Columbia, help build Sherwood News at Robinhood, and join the venture capital firm Slow Ventures, where he invests in creators. His first book, Young Money: A Field Guide to Finding Wealth and Purpose in Your Twenties, is out now. Key Learnings Jack's Grandma Ruth took him to Africa when he was 11. She was in her late 60s. She had the money. She said: "I can spend it on you now or leave it to you when I'm dead. This is better." Money has no value until you exchange it for something. We need to decide what we want that to be. Every year of your 20s is worth $10 million. (Nikita Bier) You'll never have this window of flexibility again. Say yes to interesting experiences in your 20s. Your income is going to climb exponentially anyway. Don't save $500 at the cost of a memory. Move to where the action is. Jack moved to New York for business school. Then San Francisco for a job. Then back to New York. High slope of learning. High slope of contact with good people. Network amplifies ability. It doesn't create it. A million times zero is still zero. A million times two is two million. The only real risk is not doing anything. Every opportunity in life comes through a person. The best networking tool is doing great work. How did Gracie Abrams open for Taylor Swift on the Eras Tour? She wrote great music. Taylor noticed. Taylor called. In your 20s, potential is valued at a premium. In your 30s and beyond, proof of work matters more. Experimenting when you are young speed-runs the learning curve. You develop the skill of taking shots. That skill compounds.  It's much harder to start being risk-on at 35 if you weren't risk-on at 25. Personal finance is simple. Spend less than you make. Build a six-month emergency fund. Take the 401(k) match. Contribute to your IRA. Don't gamble on individual stocks. Stay invested. Stay employed. Don't go into credit card debt. Don't get divorced. User error interrupts compounding more than anything else. Set up the boring foundation. Then stop touching it. Most retirees never touch the principal. (Nick Maggiulli) They stack money out of fear, then die with more than they started with. Daniel Kahneman on loss aversion: the pain of losing $100 is twice as strong as the joy of gaining $100. That's why people over-save. Your burn rate at 70 is way lower than at 45. No kids at home. No tuition. Less energy to do stuff. Plan accordingly. Bill Perkins' Die with Zero philosophy... A useful insight was in the first chapter: his best friend took a payday loan at 23 to backpack Europe for three months. Same career trajectory as Bill. Just way more fun at 24. People don't want to think about their mortality. So they focus on making the number go up. If you actually internalized that you're going to die, you'd be more intentional about your time and money. Jack's champagne moment a year from now: He sells a ton of copies of it. And it's still relevant. Reflection Questions Where are you spending your best years earning money you'll never actually enjoy? What would change if you accepted that your peak-energy window is closing? Where are you standing still because the risk of moving feels bigger than the risk of staying? What does the only real risk (not doing anything) look like in your life right now? What is the great work you could do that would make the right person notice you?  More Learning #539: Jack Raines - Playing Infinite Games, Living Life Backwards & Building Your Platform #548: Nick Maggiulli - The Power of Compounding #373: Bill Perkins - How To Get All You Can From Your Money & Your Life Podcast Chapters 00:00 The Price of Becoming - Pre-Order Now!  01:38 Meet Jack Raines  03:27 Grandma Ruth Took Him to Africa When He Was 11  08:04 Why Every Year of Your 20s Is Worth $10 Million  12:12 Quitting UPS at 24 for a One-Way Ticket to Barcelona  15:10 How to Increase Your Surface Area for Luck  20:00 Where You Live Is Who You Become  22:00 Why Memories Compound Faster Than Money  26:23 The Financial Stability Basics Nobody Wants to Hear  29:00 Get the Boring Stuff on Autopilot  31:15 Why Retirees Never Touch the Principal  34:02 The Bad Trade of Saving During Your Best Years  37:36 The Bill Perkins Die With Zero Debate  39:15 Experimentation, Agency, and the Only Real Risk  42:53 The Best Networking Tool in the World: Do Great Work  44:10 The Champagne Question: Making the Book Matter a Year From Now  45:53 EOPC

Before we get to this episode, I want to tell you about something I'm pumped about. It's called the arena. Great coaches want to surround themselves with other high achievers. Great coaches want to be in a group where high standards are the norm. That's exactly what the arena is, a private community of hungry, driven, growth-focused coaches, led by the Hall of Famer Sherry Cole, Brooke Cups, Garen Stokes, and Eli Liker. These are the people I personally go to to become a better leader. Here's what's different this year.

We just finished our first full year. It was awesome. Lots of coaches from all over the country at every level, from high school to college to the pros, across more than a dozen sports. Mike Powell with the Arizona Diamondback said, if you are looking for a group to push you out of your comfort zone, give you the tools to become a better human coach and leader,

this is the space. It's not comfortable, but you're going to grow. and connect. Applications for the next cohort are open now. The arena might be for you if you are a high caliber, high character coach who is not afraid to be pushed and challenge and work on yourself to be better for the people you are leading. If that's you, go to learningleader.com slash arena to apply. That's learning leader.com slash arena. Welcome to the Learning Leader Show, presented by Insight Global. I am your host, Ryan Hawk.

Thank you so much for being here. Go to LearningLeader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now, on to tonight's featured leader. Jack Raines is a writer and investor at 24. He quit his corporate finance job at UPS, bought a one-way ticket to Barcelona, and spent the next year traveling through 25 countries while writing a newsletter that grew to hundreds of thousands of readers. Since then, he's earned an MBA from Columbia, helped Robin Hood build its media company, and joined the venture capital firm Slow Ventures, where he invests in creators. His first book is called Young Money,

A Field Guide to Finding Wealth and Purpose in Your 20s. During our conversation, we discuss why Jack's grandmother Ruth took Jack when he was 11 years old to Africa and how that trip shaped everything he believes about spending money on experiences. Then how we can all increase our surface area for luck, and specifically what Jack does. We also talk about the best network. working tool, and then he shares what you can learn from studying how retirees spend their money. Super interesting. Ladies and gentlemen, please enjoy my conversation with Jack Raines.

I love your book. I love all your writing. I mean, you know, it's funny how quickly you became one of the few people who's every time you publish something, I read it. Blog, obviously your book now, like in that kind of Morgan Housel, Tim Urban, James Clear, realm of, all right, Jack, just published something new. I'm going to read it. So, dude, I, huge pop. There's some really high comparison points. It's like, yeah, they all, they sold a combined like 100 million books or whatever. So I appreciate it. No pressure,

dude. No, I'm serious. And I also think, too, like, you do a great job of being tapped into the age demographic right behind me, but you write in a way that really entertains me. I do a weird thing with AI. I was not going to say this, but we'll say it anyway, where sometimes I'll read something that's kind of confusing, and I'll say to Claude, can you rewrite this like Jack Raines? Can you rewrite this like Morgan House? I love it. That's one of my favorite uses of AI because it kind of rewrites complex things in the voice of the writers that I like.

And it's kind of cool to learn about history or something in a way like that. So I appreciate you, man. Listen, man, that's high praise. I appreciate you. Let's go back to when you're, this is where I was going to start. When you were 11, I love reading about your grandma, Ruth, mama. Mama Ruth. And she offers to take you on a trip anywhere in the world, right? And so you're thinking, well, Costa Rica or whatever, you're not really sure. But she's like, no, no, no,

anywhere, anywhere. So take for that moment, what you chose and what you learned from both that trip as well as her and her philosophy on how to spend money. So as a kid, I was a massive geography nerd. Like, I, in fact, I still have, like, around a corner of my apartment. I have, like, a map of the world with, like, pens on, like, all the places I've been. But, like, as a kid, I had this massive map in my room and like I'd memorized the capital of like pretty much every country on the planet. And when I was like really little, my grandma, my grandpa would take me on like board meetings around the U.S. Like I went with them to San Diego, D.C. like we'd fly all over the place. And yeah, when I was 11, I'm the oldest grandchild in my family.

She said, let's go on a trip for two weeks anywhere next summer. And I did not really know if anywhere meant anywhere or like relatively close to the same. to the U.S. anywhere. So I initially said Costa Rica or like a couple of other places in kind of Central America. She said, we can do that, but like where do you actually want to go? And the real answer was I wanted to go to Africa.

I was such an animal planet nerd as a kid. Like I knew all about the Serengeti and Gorogor crater Mount Kilimanjaro. Like I just thought... At 11 you knew about all this stuff? Yeah, yeah, yeah. I was like such a geography nerd. Also, I was addicted to play Halo 3, which is set

in Africa, which in the future, obviously. Obviously, like, you know, there's like missions where you're driving around Mount Kilimanjaro. You're in like coastal Tanzania. So like I had a lot of random touch points where I just knew stuff about Africa. And I thought that seeing like giraffes, zebras and lions would just be super, super cool. So I said, okay, like I want to go on a safari to Africa. And she said, okay, let's do it. And she found this tour group, T-A-UK talk tours booked in like three weeks later.

She's like, okay, we're going in June and you'll have to get like, yellow fever shot and then take like malaria medication in case you get bit by mosquitoes. She just had the whole thing lined up and we went to Africa for two weeks and I was kind of like, I sort of knew it was a little bit crazy for like your grandma from South Georgia, just like classic self-spoken, super drawn out Southern woman to take her grandkid to rural Africa. It didn't really click until years later when I was older that that was actually a pretty insane trip, but it was awesome. And she actually actually actually made me, which I thank her for this, like, journal about, like, I wrote this whole

travel blog in my 20s when I went on a backpacking trip, but that's really started when I was 11. I have this little journal called, like, Jack's Adventures in Africa. She made me write down everything we were doing. There was another family from New York that was there that had kids. I've actually reconnected with them that had kids my age that were there. And I was just writing down, like, all the random stuff we were seeing. And after the trip, years after the trip, when I was like in high school or college, I was like, why did you do that? And her take was really stuck with me was that my grandparents had like they're in their 60s pushing their 70s at that point they'd like made their money they had plenty of money and she was like I can either

spend the money on you and the rest of my grandkids now or like y'all and your parents are going to get it when we're dead and I just don't think leaving all the money in our will is the best use of that money I was like huh it was the first time I'd heard somebody verbalize thinking through like how they want to spend money over the course of their lives and at that point I was still a student. I hadn't really had a career and made money, so it just wasn't a thing I had to think about yet. But I think it was very formative on kind of how I think about the relationship between not just money and time, but money and life stages. It was useful for me to hear that as like a 16 or 17 year. We took a family vacation to the Bahamas this year. And one of the topics at dinner was, this is expensive. But this is part of the reason as to why we work really hard is to create fun token. And I forget where I heard that phrase. I didn't invent that, obviously.

But the hard work creates fund tokens, and we are cashing in our fund tokens for this week while we're here like Baha Mar and Jeskies and water slides and good food and all that stuff. And that seemed to click with our kids of like, oh, okay, okay. And so my thing was like, let's work really hard. Let's create fund tokens. And then we're going to cash them in sometimes

in addition to savings, low cost index funds, dollar cost averaging every month, all that stuff that's kind of boring. boring, but useful. So how did that trip affect you now in your mid-denal later 20s of how to best utilize money? So there's this, I don't, do you follow Nikita Beer on Twitter? He's now like the head of products of Twitter. It's crazy. I've seen you tweeting with him. Yeah, yeah. Yeah, he's one of like a cohort of people that I'm like internet friends with, but have never met. He tweeted one time, like, there was some, there's always discourse about like how much money do you

need to like be wealthy. Like it's the, the favorite talking point on Twitter of like, is $500,000 in New York poor or whatever. And he was being a little bit like speaking tongue in cheek, but I actually really liked his point where he tweeted that like every year of your 20s is worth $10 million, which I thought was pretty interesting. I would have sacrificed in 25.

I would have done a job I really didn't like if I knew it was going to get $10 million for that. I would have taken less money than that. So there's, I don't fully agree with that, but I do think this idea of like early adulthood years should really have a premium on how valuable you put them because there's this like very finite

window of time where you are like a fully independent adult but you haven't quite reached a lot of the like responsibilities that lock you into certain life stuff. For example, like I'm not married. I don't have kids. I think kids are freaking awesome.

Like I'm not in the like Gen Z camp if I'm never having kids. I'm like a big family guy. But I'm also aware that like there's a full subset of like life experiences and things you can do where you have maximum. flexibility that you really should exploit knowing that that door closes. And then by doing that, I think you can more fully enjoy that next phase of life in your 30s and 40s, like as you build a

family and you like progress in your career and become a leader in your community. So how that relates to money and time is really starting a couple of years out of undergrad, I became very aware that there was this pretty short window of time where I was going to have really high optionality. And there were a lot of like different life experiences I could go after that wouldn't cost that much money that would be highly enjoyable. That if I didn't do them at like 24 or 25, I just probably wouldn't do them or they wouldn't be nearly as enjoyable. And the, like the example I give in the book and I've like written a lot about this in like older blog post was I spent the better part of a year, just like backpacking Europe. And

Latin America at 24 and 25. And you meet like two types of people when you're doing a trip like this. You meet people who are also kind of in my bubble of maybe they're taking a gap year after college. Maybe they'd worked two or three years and took like four months between jobs to go do something fun or people who are just kind of running away from their problems. And it's kind of an age specific thing where as a general rule, the like early to mid-20 somethings are the we're having fun doing the hostile thing, hanging out with a bunch of strangers. And like we kind of all know we're going to go back to the real world within the next year, but let's have fun. Like, sort of like you're like Bahamas trip with a family, but like the like younger,

more like just chasing thrills, right? And then there's people who are like five or ten years older than me who just felt a little bit out of place. It's not necessarily they weren't having fun, but they probably would have enjoyed it more and just fit in with that lifestyle or type of trip better when they were younger. My like thought on it was, okay, if I want to do this like really cheap, call it like backpacking trip where I'm like staying in hostels with much of random roommates. I should probably do it where I'm young enough that sleeping on a train and being hung over

and miserable and like not really knowing what I'm doing is like fun and adventurous and not stressful. And that was why I did that trip. And as a broader philosophy, I from really ages like 23 to probably 27 or 28 was very much in the camp of like always say yes to like interesting experience, don't be afraid to spend money on it, knowing that this window of opportunity is pretty short. And also, like, I'm expecting my income to climb exponentially as I get into my 30s and 40s. Based on the path, I put myself on. So, like, I shouldn't worry too much about saving an extra $500 or $1,000 at the expense of, like, memories that could be really cool. Well, I wondered, too, the influence your dad had on you because he talked about this motorcycle

trip, right, that he had wished he had gone on, right? There was law school, there's life that happens, your mom did they have kids, right? And he didn't do it, right? And so what role did that conversation with your dad have on you? I love that you've read the book, by the way. I like the very pointed specific questions. No, it's interesting, right? So I, like, I was 24 and my parents had very much pushed me to be ambitious, but they never pushed me to do a specific thing. And my dad played football in college. I played football in college. He never pushed me to do that, but he did when I expressed interest and ability, pushed me to like try my hardest if this is a thing I wanted to do. So I had, for context, I'd gotten into business school at Columbia out of undergrad, but I had to

work two to four years before starting. It was basically you get an out of undergrad, you get work experience, then you go to business school. And I was about a year out from when I was planning on going to school. I've been working for 18 months. And I just like really didn't like my first job. Corporate finance, really boring. It was also COVID. So it was done. probably boring because I'm a pretty extroverted guy and I was stuck on Zoom calls like this all day, except I was looking at spreadsheets instead of you. And I just like called my dad and I was like, hey, this is going to sound crazy, but I'm thinking about quitting my job and just I was like, there's a one way ticket to Barcelona for like 300 bucks and I kind of just want to send it.

And I don't really have a plan. But like borders are reopening post-COVID. I kind of want to go see a bunch of places I haven't been. And I think this like free business school window is probably the right time to do it. And I had no idea about this until then, but he was like, I always wanted to do a motorcycle trip around the continental U.S. right after law school, but then I met your mom during law school. We started dating. We got engaged and then I'm practicing law. And he's like, now it's, you know, basically 30 years later. And he said, I don't regret any of it. Obviously, I wouldn't exist had he done that trip and it didn't work out with my mom or whatever, but he was like, I do wish I could have done that or something like that when I was in

my 20s just to say I did it. And it's like, he's not retired now, but is like, like, he could like just say he runs his own business. He can just go do it now if he wanted to. He's in his late 50s. He doesn't want to do that now. So his take was basically, if this is a thing you really want to do, you should go do it because you're not going to have a better window of opportunity. But he also was very stern that he was not going to subsidize or pay for any of it. And if I ran out of money, I was going to have to come up and figure it out. He's like, the things I will pay for for you are like your college and graduate school education. I'm not subsidizing you like backpacking Europe or partying or whatever, which I think is the right take.

I think like as a general rule, parents paying for education is good, but like don't enable hedonistic behavior. But it kind of like gave me the encouragement that, okay, he wanted to do this when he was my age and didn't. And still kind of wishes that he had done that. I should probably just say like screw it, take the trip, and then I'll make money later. That was the calculus for me. I also sense that for some reason the word luck has come up a lot recently. I've interviewed people who've written books about luck.

I see articles. I see, you know, it's out there for some. It's in my algorithm, I guess. Yep. And I feel like a guy like you who moves to where the action is, who travels on a one-way ticket, who's a social guy, read the whole, when you went to India for the wedding and stuff. How to blast. How to blast.

I feel like you're doing a good job of increasing your surface area to potentially get lucky. By instead of just resting and chilling out, you're like, I'm going to go out there, whether that's travel, whether that's moved to New York City, whether that's go to Columbia, whether that's moved to San Francisco and work with Sam and that team. You see like a series of decisions that you're continually increasing. the potential for you to get lucky. And so when someone's like, well, look at Jack, he just kind of got lucky, it's like, well,

if you actually looked at his choices, he has created the luck by going out there and doing the things that could be uncomfortable for a lot of people, how do you view luck in increasing your surface area for luck with the decisions that you make? I think like everything in life comes down to relationships. And I do think people over-emphasize

the importance of networking without thinking about like, like I view right, A network is a thing that amplifies your innate abilities where like if you've expressed ability to do well in a thing and you have a like high value network that opens opportunities, you become the guy that can exploit those opportunities that works out well for you. But having a strong network without you yourself being capable and competent is just kind of useless. It's like a million times zero is still zero, but a million times two is two million, right?

So the thing like I've always tried to do is put myself in positions to either. like do things that make me a more interesting person or do things where I am working with or surrounded by interesting people doing interesting things, which is why like moving to, I had a couple of different options for business school. I wanted to be in New York City. I came here for that. I love living in New York. I live in New York now. I think it's especially for young people like in the first call it 10 or so years of their career, probably the best place to live off of ability to make money and meet interesting people that will compound over time because it's just such a dense collection of ambition.

But when I took my current job in venture capital, it's slow, I had applied for a job initially in New York and then hit it off with one of the partners in the fund, and he was like, you should move to San Francisco. And I thought about it for probably 10 minutes, and then was like, okay, fine, I'm in. And, you know, I'd never lived in San Francisco, but the math was, I'll probably learn way more, way quicker

if I'm in the same city as the guy that I'm working for. And there's this whole cohort of, like, all the AI stuff is happening. I know there were a lot of people that I knew virtually from Twitter, newsletter, whatever, living in San Francisco, building companies, working in AI, also in venture capital, that I hadn't met in person. And I knew going in I didn't want to be there forever. But I think as a general rule, doing uncomfortable things that probably have high payoffs is usually the right decision over, you know, getting out of your comfort zone and just like avoiding complacency in general. That was a move that I was not comfortable with, but I knew was probably correct. And yeah, it off of both broadening my network and just showing me how that part of the world worked. How does the fundraising game out here work? Who's actually getting hired at these jobs?

Also, how much of what I'm seeing on Twitter is total BS. And some of these companies have no idea what they're doing or their dumpster fires. There's a lot of that. There's a lot of performative stuff on social media. And if you're not going and meeting with these companies in person and interacting with these people, you just don't really get how that world works.

Where when I was in New York initially, business school, everybody's going to banking and private equity and consulting and there's like this like track. And then you go to San Francisco and it's just out of control. People are throwing tens of millions of dollars at 21 year olds from Stanford to build AI for dogs. I mean, it is just an outrageous world, but it's awesome. And it's like as someone who's always broadly been interested in like tech and investing and kind of oscillating between like different versions of that, it was super useful for me to like really be up close and personal, just everything. going on out there. I still go back to San Francisco every month. But I've always optimized for

where will I learn a lot and like where am I going to be able to have like contact with interesting people with strong trajectories. I think if you repeatedly go for like high slope of learning and high slope of contact with good people, whether that's in the real world or like hanging out the right parts of the internet, those aren't like mutually exclusive anymore. There's just no way it doesn't work out well for you and create opportunities for you to take advantage of. Do you think you'll stay in New York long term? Let's say fast forward, wife, kids, do you think you'll stay there? I'm very much in the camp of I would like to stay in New York until I have school age kids. Like I have no issue with having like a toddler in New York

City. But then it gets into the I don't know how much money I'm going to be making. Let's say like realistically, I'm 29 now. It'll probably be eight to 10 years before I have a kid who's in the first grade. And that's if I like meet somebody tomorrow we get married in two years. years, right? So if I'm making enough money that I could have the lifestyle I wanted living in New York, I would be down with that. If it's a, wow, I could make this work. We can't save any money if I want to do the whole private school, blah, blah, blah. It's probably moved somewhere else. I don't really have anywhere that I have to live. Like, if I met a girl from Georgia and she wanted to move back to Atlanta, I'm pretty cool with that. Or like, Charleston, South Carolina.

I would be down to do the New Jersey, Long Island, Connecticut thing. Like, I'm, I want to be in New York and tell them at a point that, like, kids' school system starts to matter. And then that's probably the, like, driving thing of, where's the family support group? It's also, like, I'm in a position where I have a lot of other young, single, or at least, like, pre-kids, friends in New York. But, like, as my broader social groups' life circumstances change, the value of being Manhattan drops a lot once my career is more.

established and what's the people I like hanging out with aren't here anymore so it's like while I'm in this phase I want to be here I actually think if I was going to really play it out I'll probably be in New York for the next five to 10 years and then would like to move back once kids are like college age or at least like have an apartment here to come visit because I'd always like spending time here but I don't know it could be a thing where like something goes right I'm 40 and it's like yeah let's have a penthouse in the upper west side like I'm open to that for sure But I'm not so New York or nothing that like I would just not save money for the sake of living in Manhattan forever. Yeah.

One of the quotes, the best measure of one's life is the sum of memories you make while you're alive. And this is from the overall idea that memories compound faster than money. This is where you're ahead of your time. Can you riff and talk more about this? The best measure of one's life is the sum of memories you make while you're alive. and how memories compound faster than money. Money is so fascinating because it's the one tangible, quantifiable thing

that, like, relates to everybody, right? Like, it's kind of the lowest common denominator of, like, human comparison points where you can ballpark guesstimate how much money people make based off of what they do for work or, like, within a standard deviation of, like, net worth based off of, like,

where they went to school, who their family is, whatever. The trap you can fall into is treating money as the scoreboard and therefore treating it as like the thing you were trying to achieve. I am very pro making a lot of money. I would much rather be very rich than very poor. I think that's a like,

I think it's weird that people try to almost like vilify pursuit of money. Having money means you can just, you have much more control over your life. Like that's a very good thing to want. It means you can take care of your family. You can take care of people you care about. But the only purpose of money at the end of the day is to like spend on stuff. And that's not just like materialistic blow cash on like really expensive clothes or whatever.

It's like truly the end of the day, you're either spending money on yourself, on people you care about, or you're leaving that money to other people, whether that's leaving it as an inheritance, whether it's giving it to philanthropy. Like money, it is literally just a like non on its own non valuable asset. It's only worth of things that's at some point exchanged for. So the thing everybody has to figure out is like how much of that money do I want to exchange for things. now, both physical goods, experiences, whatever. How much of that money do I want to invest so it can compound and grow over time to spend on things later? And what I think is pretty interesting is like, my belief is that the amount of money it takes to like get a certain, call it unit of enjoyment out of life is probably a lot lower when you're young because you're just quality of life

and your expectations of quality of life are lower. For example, I live in a like 500 square foot studio apartment in New York. I have a fairly nice apartment. It's also just one dude living here, right? If I was married with a couple of kids, we need a bigger place. It's got to be more expensive. Or a few years ago, the whole backpacking Europe thing, I was in a bunk bed with like 10 random strangers,

and you have like a locker under your dad that you put your stuff in so people don't rob you. It was kind of hilarious being with like, there's like a French guy there and some of them were co-ed. It's like a French guy, Swedish girl, a bunch of like dudes that were at like Fordham. They were on study abroad. It's like a really funny setup.

I would find that just so annoying and just terrible. And I'm still in my 20s, but I'm like five years older. That's just not what I want to do. Like I'm just going to get a hotel or an Airbnb, right? So when you're really young, like a few years out of college, it just doesn't take that much money to like find the same level of enjoyment that it'll take later, which makes sense because also you make more money as you get older and you should be investing money so it compounds and grows over time exponentially.

So there's this like constant tug and pull of how much money. does it take to create those experiences that become memories now? How much money do I need to put back or how much work do I need to put in my career to increase my earnings to be able to maintain that level of enjoyment satisfaction? What you want to optimize for is hitting like a pretty high level of life satisfaction in your 20s and being able to like maintain, I call it like an eight out of 10, maintain that over the course of your life. But the amount of money it takes to maintain that goes up a lot, probably peaks in your late 40s, then as your kids grow up and start going to college,

it flattens out and plateaus until you die, right? So, like, how much money do you need to both earn and invest and, like, have expendable to be able to, like, keep that quality of life satisfaction is the thing people should be optimizing for. But because it takes more and more money to keep hitting that, people start focusing on money as the output they're optimizing for rather than money as step one, with step two being things you should put that money toward.

So that is the Jackerang's philosophy on life cycle of money. Okay, in chapter five, you have how to be stable from a financial perspective. I'll list out the bullets and maybe you can riff on these because, I mean, they seem pretty obvious, but they're not. If you actually follow these, I think you're good. One, spend less than you make. Two, build an emergency fund of six months living expenses. Take your company's full 401k match.

It's free money. contribute to your IRA, don't gamble on individual stocks, stay invested, stay employed, don't go into credit card debt and don't get divorced. Talk to me more about these bullets from Chapter 5. Yeah, I mean, to be clear, I've never been married nor divorced, but my understanding from seeing other people that have is like divorce looks like it really sucks, and it takes like all of your time, half your money, and like, I'm a huge Tom Brady fan, but man, his like post-divorce going on like maybe WWE and all this stuff is just like tough to watch. What's going?

Now, this is a little bit time sensitive, and we're both on Twitter 24-7, but, oh, my goodness. It hurts me, man. I'm a quarterback. Like, yeah. What's going on, dude? It's like watching his retirement arc versus Peyton Manning or Tony Robo, who have just, like, done a great job of, like, they're making some investments. They're talking on TV versus Tom Brady, like, viral clips of him, like, flicking off the Paul brothers and, like, fake slapping them. I don't know.

If you were old enough that you have, like, five-year-old kids and you want to be seen. at Michael Rubin's All-White Party, come on, man. Like, what do we do? You know, like, the hampons is for people in their 20s. Get out of there. At least that version of it. So, I don't know. Tom Brady's midlife crisis needs to be studied.

This is my main take on this. And I hope he gets through whatever he's going through because it's like, I'm not even a Pat's fan. I'm just somebody who respects, like, dominant performance. I really wish I just never saw anything about Tom Brady post-retirement because he really went out on top with the Super Bowl to Bucks. And it's just like, dude, even if he's making money from this, you're just, like, ruining your legacy. And, like, I don't know if it's because he, like, wants to be a billionaire and he's, like,

being too performative chasing these things or he just wants to be in the scene. It, like, kind of sucks, though. I agree. I hope LeBron James doesn't have a similar arc as the other kind of goat of this generation, but we'll see. Yeah. Sorry, I took you off track from the financial stability thing. No, you're good. I can riff on the downfall of Tom Brady forever.

I mean, look, I'm a Falcons fan. So, like, after what he did to us in the Super Bowl, several. years ago. He kind of deserves it. That's the end of my talk track. I'm Brady. Yeah, but what about those rules? You know, spending less, emergency funds, 401Ks, IRA, don't gamble on individual stuff. You're not smarter than them. I mean, most of us are not. Stay invested, stay employed, don't go into debt. Where are you at there? My take on personal finance is it's actually, like, incredibly simple to compound wealth over time in the U.S. where just like max out your 401k or at least get the company met match. And then like,

don't spend more money than you make. Literally, just track your budgets if you have credit card debt paid off immediately and then say for retirement, have it be like automatic contributions. So that way you don't have to think about it. It's just you have like, if it's $1,000 bucks a month, $2,000 bucks a month, $500 a month, just like have that going in the market and compounding. For the amount of like podcast, newsletters, whatever, that are giving personal finance advice,

up until you have like several million dollars and you're really optimizing for like taxes or estate planning or whatever, you can spend 10 minutes to chat GPT and figure out, like, how do I make sure my money is compounding at 8 to 10% a year? What I think is, like, much more interesting is, like, people don't spend enough time thinking through, like, how they want to spend that money. Again, it's not on the personal finance stuff isn't important. Like, you should have that foundation set where it's like, I don't think about the money going into my 401K, right?

For all the, all the stuff I say about don't pick individual stocks, I do still sometimes pick individual stocks, and I both made and lost a lot of money when I was 24, really aggressively picking stocks. But I'm, like, aware that that's probably not the optimal use of money or, like, brain power. Yeah, my, like, broader take on that is, like, it just isn't that hard to put yourself in a position where, assuming you remain employed and are competent at your job, like, you have a few million bucks saved up for retirement in your 60s, just by doing the boring thing right over and over and over again. And it's actually like user error can interrupt compounding way more than like you need to use like second and third level thinking to figure out how to make

more money. We just like overcomplicate personal finance. You should spend a little bit of time figuring out what's the like lowest lift hands off way to benefit from compounding and spend a lot more time thinking about once that structure set up, how and where do I want to be like spending this money and like you model out how much am I going to save up over time? Okay, what am I going to want to use that for? It's like the much more interesting question. Because you also cite some of Nick McGulie's work. Yep.

That retirees basically, they spend their whole life saving it. And then they retire, they don't spend it because they're like in this mode of save, save, save, and this is a good problem, right? But save, save, and then all of a sudden it's time to start taking it. Yeah. And they don't really do it. Can you talk more about that research, some of Nick's work as well as maybe what we could think about now before we get to those days, right?

Because again, I'm the generation right ahead of you. Those days are, they're not close yet, but they're going to get here and how to better think about that. So Daniel Kahneman has some really good studies on, like, humanity's propensity for a loss aversion, where to like really, really quickly summarize his work on this, the pain you get from taking a loss, like, financially is about twice as strong as the joy you get from, like, a gain, where if you make $100, you get like five feel-good points. If you lose $100, you get negative 10 feel-good points. And because of that, like, people are really wired to not want to lose money,

which means that when it comes to, like, saving for retirement, most people will really optimize for, I need to keep stacking money because I do not want to be in a position where I lose money. And granted, like, the older you get, the higher chance of, like, a health scare or there's a natural disaster that messes up your home. or like, the just over time, the number of things that can go wrong that could really screw you financially increase exponentially. So it's like, it's not an ungrounded fear that you could think I need to have such a big nest egg that like nothing can touch me. But going to at a Nix point, like,

Nick's the CEO of Ritt Holt's wealth management, I would say he's probably the one of the, if not the best, just pure play like personal finance guys out there right now. And he pulled a bunch of data over the last, I don't know what the time period was, 30 years or whatever, of like retirees. And his findings were that, like, most people, they don't ever touch the principle of the money, like, put their retirement account, meaning that, like, their gains are compounding faster than they're spending it down, when in reality, I don't think you should try to optimize for, like, I spend down all of my money in retirement because you actually just don't know how long you're going to live.

You should always keep a margin for error where you can keep compounding. But like, if you retire at, call it 70 with like $10 million and then you die in 90 with $25 million, that actually probably wasn't the optimal amount of, like, you probably should have spent more money sooner where like you still have money to leave to your kids and grandkids or whatever. But how much utility do you just like leave out there on the field that you didn't take advantage of when you were alive because you were, you had a scarcity mindset. So the way that I think about it is like, if you're that person who they couldn't spend on their retirement. if they tried to because the other thing is when you're in your 40s or even your 50s, your burn rate is probably way higher than it's going to be when your kids are out of the home and they're self-sufficient. And the amount of money you're spending on your kids in like high school and college of like sports and tuition and all this stuff, maybe like helping them out

right out of school. By the time they're 30, say they're 30, you're 60. They're probably like totally self-sufficient at that point. But you're going to be anchoring to while my burn rate when my kid was 21 was this and you think you need to keep hitting that when actually as you get close to you're just going to spend less money. You have less energy to do stuff. You have way less expenses on like your family. You're probably not supporting your kids anymore. So you probably should have spent more money on stuff when you were younger because like

the burn rate is not going to be that high later. Again, I think running out of money in retirement is a way worse problem than having too much money. Like I do not think you want to be like destitute and like a burden on your family in your 80s. But having way too much money at a point in life where you don't have the energy. you to do anything with it is like a completely self-induced problem that like shouldn't happen. So I think the thing to think about is like actually look at the data of like people in your

income cohort of what their burn rates actually are in retirement to realize that, okay, what I'm spending at 45 or 50 is actually probably higher than what it will be at 70. And then thinking about, okay, you might have like 10 years in retirement where you're still high energy maybe in your 70s where you want to go do stuff. and that's gonna slow down a lot in your 80s, where should I be spending while I actually have the ability to do it? Because I don't think people really internalize how much their mobility and energy drops with age,

especially like old age. And once you get to that point, like when you're 85, you can barely see or walk, there actually isn't that much you can spend the money on to do other than just healthcare-related, like staying alive stuff. So versus your 60, you still have a ton of energy. Your kids are probably out of the house. You should probably take the like, I don't know.

I have like a great uncle and great. They just twice now. They've just sailed around the world. They're getting too old now where they can't really do it anymore. They took a mini retirement in their 40s and just like sailed to Australia, New Zealand, which is like kick ass. It's my, it's my grandpa's sister and her husband. They did that. My uncle went down and visited them when he was in high school or college.

And then they did it again in their 60s. And it's like, yeah, take a mini retirement. You made all that money in your 20s and 30s and early 40s. It's like 25 years of making. money, take a year off and go do a sabbatical and then come back to it if you need to. I just, the whole idea of, I'm going to save all my money over the most valuable parts of my life to then try to spend it and be least valuable part of my life is just a really stupid trade where I think it comes down to either people aren't really running the numbers on it or

my more like meta philosophical and prospective take is like people really don't like contemplating their own mortality and aging and just like the like called depreciation, their physical self where to fully understand that you need to capture the moment now, you also have to accept that like you're fighting against the clock. It's almost easier to just ignore that reality. And then if you're ignoring that reality, you just keep focused on making the number go up. So my, this is my like crazy young person take on a lot of this is that a lot of people's problems just come from like they don't want to deal with the fact that they're going to die one day.

And if you actually internalize that, you would probably be a lot more intentional about how you spend your money and your time. Have you talked to Bill Perkins, the die with zero guy? We have never talked in person, but like we've chatted on Twitter before a few times. What do you think of them? So one, I think Bill Perkins has, I think he is the perfect type of rich dude where I don't know, as far as he made a lot of money as a trader and running a fund. He's also a pro poker player.

He's produced movies. He's a best-selling author. I don't know. I follow him on Instagram. Him and his wife and new kids seem to be having a great time just like bowling around on their boat or whatever. He made the money and knows how to spend it. But he started a couple of venture back companies.

He's like still a super active entrepreneur businessman, like runs a fund. But his old philosophy would die with zero and like spend down the money over the course of your life, I think is right. Like if you put yourself in a position where you're at the top of your game, what do you want to do with that? But what's really interesting about him is in the first chapter of his book, he talks about how his best friend in his first job Took a few months off and just went to Greece and just like hung out in Europe It took a payday loan from a loan shark because they were only making like 20k a year at the time in Manhattan

Which was just even back in then. That was nothing and just went to Europe for three months. Guess what he came back and he was a successful energy trainer in Texas Him and Bill had very similar career paths the difference was one of them had way more fun at 24 than the other one and like one of Bill's regrets was that he didn't really do a trip like that until he was 30. And by then, that window of like crazy young guy going on journey. He had some story about like meeting some Greek girl and like falling in love or some fleeing. Like he just didn't get all those random things at 24. And he was like, I could have done that and still have the same career. So Bill's whole take on like the usefulness of money I'm like pre-lined with. You just retweeted this. I think right before we started somebody's advice. Basically here it is. It says for young people. I just think I disagree.

I think it's for people. I think you could cut out the young part. Experiment as much as possible. Don't feel like you're wasting time. The only real risk is not doing anything. Again, we're increasing the potential. You mentioned this earlier, but every single opportunity in life,

literally every single one of them, comes through a person. Yep. And that comes through a person you probably have some sort of a relationship with. And the only way, I think, to develop an actual real relationship with a person is to go out there and be with them, to see them,

to increase the odds that you'll actually touch shoulders, you know, going out, they're doing things. So I think the only risk is not doing that. And I feel like this is kind of the mode where you're at. Yep. So that retreat was Stephen Wop. The company's called Wop. It's like an e-commerce company.

Hilariously, I joke that they're like the Shopify for course bros. but they're like the e-com platform for all the like, call it Gen Z people doing weird e-com sort of scammy stuff. Wop is a real business. I don't know if a single one of their customers have real businesses or not, but they built like a sick platform. It's funny. There's this whole subset of advice that like,

like Stephen's proud about my age. He looks like he's in his 20s. There's this whole subset of advice that like young people give that probably applies to everybody, but you don't want to be the 28-year-old who's like initially giving advice to the 50s. year old because you're not there. So you say this is for young people. That's

kind of like my book. Like the whole thing I have geared it toward people in their 20s. In reality, a lot of the like time and money and opportunity cost and status game stuff is like pretty applicable to anybody. But I can only like with confidence say like I know what it's like to be a 25 year old dealing with this

stuff because I have been a 25 year old. I've never been like a 40 year old with kids. But yeah, going back to like that take itself, I mean I the one thing I'll push back on you a little bit is like, I agree that like being like very like experimental, taking shots and trying stuff is basically like say like having high agency and the ability to like be uncomfortable is a useful lifelong skill.

I think you have a lot more leverage on it when you're young because like the older you get, the more you have to have like proof of work for people to take you seriously versus when you're young, I talk about this in my book, but your potential gets valued at a premium in your 20s. And then, like, as you hit your 30s and older, proof of work matters more and more. Being heavily experimental and trying a lot of stuff when you're young, just speed runs the time in which, like, you can make contact with interesting people in a lot of different domains.

And also, like, your learning curve accelerates because the more that you're experimenting when you're young, the more you can, like, go up these, like, proficiency curves and different vectors. And you can develop a feel for, like, what you actually like doing and where you want to spend your time. So by the time you hit your 30s and 40s and you really want to see those bets compounding, you have like a very good sense of self, right? It's like you experiment a lot when you're young. You develop a skill set to experiment and take shots versus if you never really take shots. I think it's much harder to start being risk on at 35 if you were never risk on in your 20s, right? So it's a lifelong skill, but like anything else, the ability to do things in the compound compounds,

but you want to take a lot of weird, interesting shots when you're young. like you can figure out which in those paths you want to double down it reminds me of um i have this section most recent book that's just called the best networking tool and in my opinion the best networking tool is doing great work yep which is what you're talking about like competence not just experimenting but i mean one of the examples it's a little bit crazy and it's not a perfect example because her dad's famous but like how does gracie abrams get on the airs tour as an opener i i saw her open as one of the shows I went to and was my daughters and um she did it because she she worked really really hard and wrote beautiful great music in some people's eyes i like it yeah

and taylor noticed and taylor called people who she noticed was really really good so how did gracy get in front of taylor she created great work she was very competent at her job right she's very good at being a musician and taylor said let's go did her dad and all that that help probably yes right but if she wasn't good it doesn't matter that's not happening i think part of it is the best networking tool in the world by far is doing great work other people will then notice and then that creates the opportunity for you to meet and then it's on you to make the most of those opportunities but the best networking tool is creating great work yeah yeah totally agree with that one question more before we go the champagne question comes from my friend jason

gainard it's a year from now you're surrounded by all the people you love friends family and And you guys are popping bottles like crazy. You're celebrating. I'm curious, what are you celebrating? I mean, hopefully my book blew up. Like, at the time of recording, this will come out in two weeks. I guess, like, when it actually, like, comes out, it'll be right around March day. I mean, the, like, you've been through the book gauntlet a few times now.

This is my first time going through it. It's like, there's so much you can do to try to make a book do well. But at the end of the day, you write the best thing you can. You do what you can to, you know, get people to know about it and care about it. And then ultimately, like, it either travels word of mouth or it doesn't, right? So, like, I'm less concerned with the, oh, I need to get big marketing pop. And I want this to be a thing that, like, a lot of people do that speed run the launch, fine. I wanted to be a thing that a year from now people actually care about and have, like,

told other people about. And whether that's like, I don't know, like, I'm not going to put a set number on number of sales or if it's New York Times list or whatever. But, like, for what I wrote to be a relevant thing, people are talking about a year from now, and there being some milestone or bench smart that I hit a year from now, probably that. Yeah, I love it. Book is called Young Money, A Field Guide to Wealth and Purpose in your 20s. As we just said, though, it certainly applies to people beyond that.

Look at that, dude. The hardcover, I think, looks a lot better. The colors look better than the soft back. It looks good. They sent me one of the soft ones, the early ones. I got to get the hardcover too. But it's really well done, dude. Like your other writing, it's obviously I love it.

big fan of your work, man. And certainly we're going to continue our dialogue as we both progress, man. 100%. Thanks again for having me. It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learning leader.com. Let me know what you learn from this great conversation with Jack Raines.

A few takeaways from my notes. Get the boring stuff on autopilot. Spend less than you make. Build the emergency fund. Take the full 401k match and automate the contributions dollar cost averaging every month no matter what. Set it up once so you can stop thinking about it and spend your attention on the decisions that actually change your life. Get the boring stuff on autopilot. Next, spend on the things that expire.

Some experiences only work at a certain age. Some of this comes from Bill Perkins and die with zero, meaning if you're going to go hiking, do it now. If you can go skiing, do it now. Maybe later in life, you won't be able to. So like in Jack's case, sleeping in a hostel with your best friends is an adventure at 24, but you don't want to do that at 40. So what's something you want to experience right now, but haven't done it yet? Take this as a nudge to do that thing right now, much like Jack's grandmother,

taking him to Africa when he was 11 years old and spending on experiences. And then the best networking tool, do. great work. The most reliable way to meet people worth knowing is to do something worth noticing. Jack has created some life-changing relationships for himself because he's had the guts to publish his work online and it's really good. And he's amassed a big fan base, which has led to all of those great opportunities. So how can all of us network with others do excellent work?

Once again, I'm going to say thank you so much for continuing to spread the message and telling a friend or two. Hey, you should listen to this episode of The Learning Leader Show with Jack Raines. I think he'll help you become a more effective leader because you continue to do that. And you also go to Spotify and Apple Podcasts and you subscribe to the show and you rate it, hopefully five stars and you leave a thoughtful review by doing all of that. You are giving me the opportunity to do what I love on a daily basis. And for that, I will forever. Be grateful. Thank you so, so much. Talk to soon. Can't wait.