699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money

The Learning Leader Show with Ryan Hawk www. LearningLeader.com https://www. LearningLeader.com This is brought to you by Insight Global https://insightglobal.com/learningleader/. 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 https://learningleader.com/jackraines/ - Playing Infinite Games, Living Life Backwards & Building Your Platform #548: Nick Maggiulli https://learningleader.com/nickmaggiulli548/ - The Power of Compounding #373: Bill Perkins https://learningleader.com/episode/373-bill-perkins-how-to-get-all-you-can-from-your-money-your-life/ - 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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Hawk?

  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 Sherri Cole, Brooke Cups, Garen Stokes, and Eli Leicher. 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

• 0:43Ryan Hawk?

  across more than a dozen sports. Mike Powell with the Arizona Diamondbacks 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 challenged and work on yourself to be better for the people you are leading. If that's you, go to learningleader.com/arena to apply. That's learningleader.com/arena.

• 1:30Ryan Hawk?

  Welcome to the Learning Leader Show presented by Insight Global. I am your host, Ryan Hawke. 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 Rains 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 Robinhood build its media company,

• 2:15Ryan Hawk?

  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 networking tool. And then he shares what you can learn from studying how retirees spend their money.

• 3:00Ryan Hawk?

  Super interesting. Ladies and gentlemen, please enjoy my conversation with Jack Rains. 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 publish something new. I'm going to read it. So, dude, I huge.

• 3:25Speaker 01

  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.

• 3:33Ryan Hawk?

  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 Rains? Can you rewrite this like Morgan Housel?

• 3:56Speaker 01

  I love it.

• 3:57Ryan Hawk?

  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.

• 4:09Speaker 01

  Listen, man, that's like high praise. I appreciate you.

• 4:12Ryan Hawk?

  Let's, let's go back to when you're, this is where I was going to start. When you were 11, I loved reading about your grandma Ruth, Mama Ruth, and she offers to take you on a trip anywhere in the world, right? And so you're thinking, oh, Costa Rica or whatever, you're not really sure. But she's like, no, no, no, anywhere, anywhere. So take 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.

• 4:38Speaker 01

  So as a kid, I was a massive geography nerd. Like I, in fact, I still have like around the corner in my apartment, I like a map of the world with like pins on like all the places I've been. But like as a kid, I had this massive map in my room and like I had 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 US. Like I went with them to San Diego, DC, 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 US anywhere. So I initially said Costa Rica or like a couple of other places in kind of Central

• 5:23Speaker 01

  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 Gorgor Crater, Mount Kilimanjaro. Like I just thought.

• 5:39Ryan Hawk?

  At 11, you knew about all this stuff?

• 5:40Speaker 01

  Yeah, I was like such a geography nerd. Well, also I was addicted to play Halo 3, which is set in Africa, which in the future, 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 and 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.

• 6:22Speaker 01

  And 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 made me, which I thank her for this, like journal about like, I wrote this whole travel blog in my twenties when I went on a backpacking trip, but that's really started when I was 11. I have this little journal called like Jackson Ventures 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.

• 7:07Speaker 01

  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 like had a career or made money.

• 7:51Speaker 01

  So it just wasn't a thing I'd had to think about yet. But I think it was very formative on kind of how I think about like the relationship between not just money and time, but money and like life stages. It was useful for me to hear that as like a 16 or 17-year-old.

• 8:05Ryan Hawk?

  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 of, as to why we work really hard is to create fun tokens. And I forget where I heard that phrase. I didn't invent that, obviously. But the hard work creates fun tokens and we are cashing in our fun tokens for this week while we're here, like Baja Mar and jet skis and you know, 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 fun 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, but useful.

• 8:48Ryan Hawk?

  So how did that trip affect you now in your mid to now later twenties of how to best utilize money?

• 8:57Speaker 01

  So there's this, I don't, do you follow Nicky De Beer on Twitter? He's now like the head of products at Twitter.

• 9:02Ryan Hawk?

  It's crazy. I've seen you tweeting with him. Yeah, yeah.

• 9:03Speaker 01

  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 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 twenties is worth $10 million, which I thought was pretty interesting. I would have sacrificed at 25, I would have done a job I really didn't like if I knew I 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 like how valuable you put them

• 9:48Speaker 01

  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 of 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.

• 10:32Speaker 01

  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 are 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, 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 posts, 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.

• 11:14Speaker 01

  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 20s things are the we're having fun doing the hostel 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 the family, but like the like younger, more like just chasing thrills, right? And then there's people who are like five or 10 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

• 11:59Speaker 01

  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 a bunch of random roommates. I should probably do it where I'm young enough that sleeping on a train and being hungover 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.

• 12:41Speaker 01

  And also like I'm expecting my income to climb exponentially as I get into my 30s and 40s, based off 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.

• 12:57Ryan Hawk?

  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's law school, there's life that happens, your mom have kids, right? Yep. And he didn't do it, right? And so what role did that conversation with your dad have on you?

• 13:13Speaker 01

  I love, I love that you've read the book, by the way. I like, 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 in 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.

• 13:55Speaker 01

  I'd 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 doubly 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 pre-business school window is probably the right time to do it. And I, I had no idea about this until then, but he was like,

• 14:38Speaker 01

  I always wanted to do a motorcycle trip around the continental US 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 like 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 twenties, 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 could 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.

• 15:21Speaker 01

  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 over 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, 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, the calculus for me.

• 16:01Ryan Hawk?

  I also sense that for some reason that the, the word luck has come up a lot recently. I've interviewed people who've written books about luck. I see articles, I see, see, you know, it's, it's out there for some, it's in my algorithm, I guess.

• 16:13Speaker 01

  Yep.

• 16:14Ryan Hawk?

  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.

• 16:28Speaker 01

  Kind of blast, kind of blast.

• 16:30Ryan Hawk?

  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 move to New York City, whether that's go to Columbia, whether that's move 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?

• 17:12Speaker 01

  I think like everything in life comes down to relationships. And I, I do think people over emphasize the importance of networking without thinking about like, like I, I view a, a network as a thing that like amplifies your innate abilities. Where like if you've expressed ability to do well at 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 that like I've always tried to do is put myself in positions to either like,

• 17:54Speaker 01

  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 like ambition. But when I took my current job in venture capital of slow, I had applied for a job initially in New York and then headed off with one of the partners in the fund. And he was like, you should move to San Francisco.

• 18:35Speaker 01

  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.

• 19:17Speaker 01

  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 and they're dumpster fires. There's a lot of that. Like there's a lot of performative stuff on social media and. If you're not going and meeting with these companies in person and like interacting with these people, you just don't really get how that world works. Where when I was in New York initially, it's 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

• 20:00Speaker 01

  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 with 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 in the right parts of the internet, those aren't

• 20:44Speaker 01

  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.

• 20:51Ryan Hawk?

  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?

• 20:58Speaker 01

  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, 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, like can't save any money if I want to do the whole like private school, blah, blah, blah. It's probably move 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,

• 21:43Speaker 01

  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 until I'm at a point that like head 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 once 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

• 22:24Speaker 01

  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. Cause 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, 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.

• 22:50Ryan Hawk?

  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?

• 23:15Speaker 01

  Money is so fascinating because it's the one tangible, quantifiable thing that like relates to everybody, right? Like it's kind of the like 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. And I think that's a like, I think it's weird that people try to almost like vilify pursuit of money.

• 23:57Speaker 01

  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 the things that's at some point exchanged for. So the, the thing everybody has to figure out is like, how much of that money do

• 24:41Speaker 01

  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 going to be more expensive. Or a few years ago, the whole

• 25:24Speaker 01

  backpacking Europe thing, I was in a bunk bed with like 10 random strangers and you have like a locker under your bed 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 coed. 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 twenties, 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. Cause 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

• 26:08Speaker 01

  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 and satisfaction? What you want to optimize for is hitting like a pretty high level of life satisfaction in your twenties 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

• 26:52Speaker 01

  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 the things you should put that money toward. So that is the Jack Ryan's philosophy on life cycle of money.

• 27:14Ryan Hawk?

  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 five.

• 27:48Speaker 01

  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, like going on like maybe WWE and all this stuff is just like tough to watch.

• 28:04Ryan Hawk?

  Dude, what's going on? Now, this is a little bit time sensitive and we're, we're both on Twitter 24 seven, but yeah, oh my goodness. It hurts me, man. I love, I'm a quarterback. Like, yeah, what's going on, dude?

• 28:16Speaker 01

  It's like watching, 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, what, what are we doing? Like that happens for people in their twenties. Get out of there. At least that version of it. So I don't know. Tom Brady's midlife crisis needs to be studied. That is my, my main take on this. And I hope he gets through whatever he's going through. Cause it's like, I'm not even a Pats fan. I'm just somebody who respects like dominant performance. I really

• 28:59Speaker 01

  wish I just never saw anything about Tom Brady post-retirement because he really went out on top with the Superbowl 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.

• 29:19Ryan Hawk?

  I agree.

• 29:20Speaker 01

  I hope LeBron James doesn't have a similar arc as the, the other kind of goat of this generation, but we'll see.

• 29:25Ryan Hawk?

  Yeah. Sorry. I took you off track from the financial stability thing.

• 29:28Speaker 01

  No, you're good. I can riff on the downfall of Tom Brady forever. I mean, like I'm a, I'm a Falcons fan. So like after what he did to us in the Superbowl several years ago, he kind of deserves it. That's the end of my talk track on Brady.

• 29:39Ryan Hawk?

  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?

• 29:52Speaker 01

  My take on personal finance is it's actually like incredibly simple to compound wealth over time in the US where just like max out your 401k or at least get the company mid-match and then like, don't spend more money than you make. Literally just track your budgets. If you have credit card debt, pay it off immediately and then Save 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 a thousand bucks a month, 2,000 bucks a month, 500 bucks a month, just like have that going in the market and compounding. For the amount of like podcasts, newsletters, whatever, they're 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.

• 30:36Speaker 01

  You can spend 10 minutes with ChatGPT and figure out like, how do I make sure my money is compounded, get eight 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 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.

• 31:16Speaker 01

  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, we just like over complicate personal finance. You should spend a little bit of time figuring out what's the like lowest left hands off way to benefit from compounding and spend a lot more time thinking about.

• 31:54Speaker 01

  Once that structure's 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 is like the, the much more interesting question.

• 32:06Ryan Hawk?

  Cause you also cite some of Nick Medjulie's work.

• 32:09Speaker 01

  Yep.

• 32:09Ryan Hawk?

  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, 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 and they, 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? Cause 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 like how to better think about that.

• 32:41Speaker 01

  So Daniel Kahneman has some really good studies on like humanity's propensity for like 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 a hundred dollars, you get like five feel-good points. If you lose a hundred dollars, 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.

• 33:27Speaker 01

  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 you're about to Nick's point, like Nick's the COO of Ritholtz 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 principal 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.

• 34:12Speaker 01

  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. Uh, 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 did 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.

• 34:53Speaker 01

  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 were going to be anchoring to, wow, my burn rate when my kid was 21 was this, and you think you need to keep hitting that. When actually, as you get closer to retirement, 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's just not going to be that high later.

• 35:37Speaker 01

  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 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 like look at the data of like people in your income cohort of what their burn rates actually on 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.

• 36:21Speaker 01

  And that's going to like slow down a lot in your 80s. Where should I be spending while I actually have the ability to do it? Cause 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 you're 60, you still have a ton of energy. Your kids are probably out of the house. Like you should probably go take the like. Like, I don't know. I have like a great uncle and great, they're 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.

• 37:05Speaker 01

  It's my, it's my grandpa's sister and uh, her husband, they did that. My uncle went down and visited them when he was in high school or college and they did it again in their 60s. And it's like, yeah, take a mini retirement. You made all that money in your twenties and thirties and early 40s. That'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, uh, 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 like least valuable part of my life. It's just a really stupid trade where I think it comes down to either people aren't really running the numbers on it.

• 37:41Speaker 01

  Or my more like meta philosophical introspective take is like, people really don't like contemplating their own mortality and aging. And just like the like, call it depreciation of 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, my like, 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.

• 38:21Speaker 01

  And if you actually internalize that, you would probably be a lot more intentional about how you spend your money and your time.

• 38:27Ryan Hawk?

  Have you talked to Bill Perkins, the die with zero guy?

• 38:30Speaker 01

  We have never talked in person, but like we've chatted on Twitter before a few times.

• 38:34Ryan Hawk?

  What do you think of him?

• 38:34Speaker 01

  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 bestselling 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's still like, like he started a couple of venture backed companies. He's like still a super active entrepreneur, businessman, like runs a fund. But his whole philosophy of like 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.

• 39:14Speaker 01

  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 at his first job took a few months off and just went to Greece and just like hung out in Europe. He took a payday loan from a loan shark because they were only making like 20K a year at the time in Manhattan, which was even back then, that was nothing. And just went to Europe for three months. Guess what? He came back and he was a successful energy trader 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, like falling in love or some fling. Like he just didn't get all those random things at 24.

• 39:59Speaker 01

  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 pretty aligned with.

• 40:07Ryan Hawk?

  You just retweeted this, I think, right before we started. Somebody's advice, basically here it is, this 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.

• 40:37Speaker 01

  Yep.

• 40:37Ryan Hawk?

  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 there, 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.

• 41:02Speaker 01

  Yep. So that, that retweet was, uh, Stephen WAP. The company's called WAP. It's like a e-commerce company. Hilariously, I joke that they're like the, um, the Shopify for course bros. But they're like, they're like the e-comm platform for all the like, call it Gen Z people doing weird e-comm sort of scammy stuff. WAP 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, there's this whole subset of advice that like, like Stephen's probably about my age, he looks like he's in his twenties. 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 intentionally giving advice to the 50 year old because you're not there. So you say, this is for young people.

• 41:46Speaker 01

  That's kind of like with my book, like the whole thing, I have geared it toward people in their twenties. 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.

• 42:28Speaker 01

  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 twenties. And then like, as you hit your thirties 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.

• 43:11Speaker 01

  So by the time you hit your thirties and forties 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 skillset to experiment and take shots versus if you never really take shots. I, I think it's much harder to start being risk on at 35 if you were never risk on in your twenties, 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. So like you can figure out which in those paths you want to double down.

• 43:44Ryan Hawk?

  It reminds me of, um, I have the section, most recent book. It's just called the best networking tool. And in my opinion, the best networking tool is doing great work.

• 43:55Speaker 01

  Yep.

• 43:55Ryan Hawk?

  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 with 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.

• 44:22Speaker 01

  Yep.

• 44:22Ryan Hawk?

  And Taylor noticed and Taylor called people who she noticed was really, really good. So how did Gracie 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 help? Probably, yes.

• 44:41Speaker 01

  Yep.

• 44:41Ryan Hawk?

  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, to make the most of those opportunities. But the best networking tool is creating great work.

• 45:00Speaker 01

  Yep. Yeah, I totally agree with that.

• 45:02Ryan Hawk?

  One question more before we go. The champagne question comes from my friend, Jason Gaynard. It's a year from now, you're surrounded by all the people you love, friends, family, and you guys are popping bottles like crazy. You're celebrating. I'm curious, what are you celebrating?

• 45:16Speaker 01

  I mean, hopefully my book blew up. Like at the time of recording, this, this will come out in two weeks. I guess like when it actually like comes out, it'll be right around launch 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 want it 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

• 46:01Speaker 01

  of sales or if it's a 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 benchmark that I hit a year from now, probably that.

• 46:12Ryan Hawk?

  Yeah, I love it. Book is called Young Money, A Field Guide to Wealth and Purpose in Your Twenties. As we just said, though, it certainly applies to people beyond that. Look at that, dude. I love it.

• 46:23Speaker 01

  The, the, the hardcover I think looks a lot better. The colors look better than the softback.

• 46:26Ryan Hawk?

  It looks good. They sent me one of the soft ones, the early ones. I gotta get the, I gotta get the hardcover too, but it's, it's really well done, dude. Like your other writing, it's obviously, uh, I love it. Big fan of your work, man. And certainly we're going to continue our dialogue as we both rest, man.

• 46:40Speaker 01

  A hundred percent. Thanks again for having me.

• 46:45Ryan Hawk?

  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 learningleader.com. Let me know what you learned from this great conversation with Jack Rains. 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.

• 47:28Ryan Hawk?

  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're going to 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.

• 48:09Ryan Hawk?

  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 want 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 Rains. 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

• 48:54Ryan Hawk?

  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 you soon. Can't wait.