The best measure of one's life is the sum of memories you make while you're alive.
The whole idea of I'm going to save all my money over the most valuable parts of my life, then try to spend it at the least valuable part of my life is just a really stupid trade.
Memories compound faster than money.
Every year of your 20s is worth $10 million. 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.
You're doing a good job of increasing your surface area to potentially get lucky. Instead of just resting and chilling out, you're like, I'm going to go out there. 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 2 million.
Starting a couple years out of undergrad, I became very aware that there was a pretty short window of time where I was going to have really high optionality and there were a lot of different life experiences I could go after that just wouldn't cost that much money. 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.
Experiment as much as possible. Don't feel like you're wasting time. The only real risk is not doing anything. Always say yes to interesting experiences. Don't be afraid to spend money on it.
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.
There's some really high comparison points. Like 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 Housel? I love it. And it's interesting what it like that's one of my favorite uses of AI because it kind of rewrites like complex things in a way 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 yeah, you're one of those dudes. So I appreciate you, man.
Listen, man, that's like high praise. I appreciate you.
Let's go back to when you were, 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 Costa Rica or whatever. You're not really sure, but she's like, no, no, no. Anywhere. Anywhere. So take me to 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 the corner of my apartment, I have 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 I memorized the capital of like pretty much every country on the planet. And when I was like really little, my grandma and 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 America. And 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 like the Serengeti and Ngorongoro Crater, Mount Kilimanjaro. Like I just thought I thought
At 11 you knew about all this stuff.
Yeah. Yeah. Yeah. I was like such a geography nerd. Well, also I was addicted to playing 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, like let's do it. And she found this tour group, Tauck Tours, booked and 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 we'll both need to get like you have to take like I think you have to get a shot and then take like malaria medication in case you get bit by mosquitoes. She 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 like softspoken super drawn out southern woman to take her grandkid to rural Africa. Um, I didn't really, it didn't really click until, you know, like 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 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. And it's like 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. Um, and I was just writing down like all the random stuff we were seeing. And after the trip, I asked her like years after the trip when I was like in high school or college, I was like, why did you do that? And her take which really stuck with me was that like 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 like 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 for like in our will is the best use of that money. I was like, huh? Like that's it. 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, like I was still a student. I hadn't really like had a career or made money. 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.
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How do you think about it now as to how you use money? I'll just surface a thesis because we took our family vacation to the Bahamas this year and one of the topics at dinner was like, you know, this is it's expensive and I said, but this is part of the reason 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 Baha 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. That stuff that's kind of boring but useful. So, how did that trip affect you now in your mid to now later 20s of to how to best utilize money?
So, there's this I don't do you follow Nikita Bier on Twitter. He's now like the head of product at Twitter.
It's crazy. I've seen you tweeting with him. Yeah. Yeah.
Yeah. We've been like Twitter I've never met him in person. We've been Twitter mutuals for like four or five years. He's one of like a cohort of people that I'm like internet friends with but have never met. Um 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 had like a 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. And the you know whether or not like I would not like there were 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. So like I actually 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 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 like 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 the way that like how that relates to money and time is really starting a couple years out of undergrad, I became very aware that there was this like 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 just 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 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. 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 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 your like Bahamas trip with the family but like the younger more like thrill running by 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. Like 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. And 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 like 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 interesting experiences. 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 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.
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, they have kids, right? And he didn't do it, right? And so, like 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. Um, no, it's interesting, right? So, I was 24 and my parents had very much like pushed me to be ambitious, but they never pushed me to do a specific thing. Like my dad played football in college. I played football in college. He never pushed me to do that. But he did when I like expressed interest and ability push me to like try my hardest if this was 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. 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 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 he was I had no idea about this until then, but he was like, 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 20s just to say I did it. And it's like he's not retired now, but is 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 cuz 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 gonna have to come home 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 yeah, 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 was kind of my that was the calculus for me.
I also think it I sense that for some reason the word luck has come up a lot recently. I've interviewed people who've written books about luck. We see articles. I see, you know, it's out there for some. It's in my algorithm, I guess.
And I feel like a guy like you who moves to where the action is, who travels on a one-way ticket, who's, you know, a social guy. I read the whole when you went to India for the wedding and stuff. A blast. I mean, 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 in that team. It seems 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 and increasing your surface area for luck with the decisions that you make?
I mean, I think like everything in life comes down to relationships. And I do think people overemphasize the importance of networking without thinking about like I view a network as a thing that like 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. It 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 2 million, right? So, the thing that like I've always tried to do is like 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 loved 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 with Slow, I had applied for a job initially in New York and then hit it off with one of the partners of 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 like 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 didn't I knew going in I didn't want to be there forever. But like I think as a general rule, doing uncomfortable things that probably have high payoffs is usually the right decision like over you know getting out of your comfort zone and just like avoiding complacency in general. And that was a move that I was not comfortable with, but I knew was probably correct. And yeah, it like off of both broadening my network and just showing me how that part of the world worked. Like how does the fundraising game out here work? Like 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 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 like 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 control. People are throwing tens of millions of dollars at 21 year olds from Stanford to build like 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. And I still go back to San Francisco every month. Like I joke that I like to dunk on San Francisco. It's like a very cool city. It's just like not where I would prefer to live right now. But I have 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 like mutually exclusive anymore. There's just no way it doesn't work out well for you and create opportunities like for you to take advantage of.
Do you think you'll stay in New York long term? Like let's say fast forward, wife, kids, you think you'll stay there?
It's an interesting question. I mean, 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 like 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 8 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 but can't save any money if I want to do the whole like private school blah blah blah. It's probably move somewhere else. And I'm like 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 want to be in New York until I'm at a point that like family really until 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 like young single or at least like pre-kids friends in New York. But like as my broader social group's life circumstances change, the value of being in 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 play it out, I'll probably be in New York for the next 5 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. Um, 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 lines I like that I because I think some people who are like the VP of sales at a Fortune 500 company, which is like the typical avatar for this show, and that person's probably like mid-40s with family and kids. So, they're like, why am I going to listen to this dude? You know, he's in his 20s and doesn't have kids yet. And I think if anyone's saying that, I think you're so misguided. One of the things that you write about because I think you write while I know your demographic is for that person maybe a little bit a few years behind you based on what this book is about. I think it's actually for people that are much older could benefit from it as well. 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 kind of like the overall idea that memories compound faster than money. This is where you're ahead of your time, I think, of your age. 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.
Yeah, 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. And I think there's this really risky like 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 versus taking a step further and thinking about like my view on money is that and again like 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. 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 at 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 is literally just a holding pattern that money is it is literally just a like on its own non-valuable asset. It's only worth the things it'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 your quality of life and your expectations of quality of life are lower. For example, I live in a like 500 ft studio apartment in New York. I have a fairly nice apartment. It's also just one dude living here, right? Like if I was married with a couple of kids, we'd need a bigger place. It's going to be more expensive. Or like 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 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 co-headed. It's like a French guy, Swedish girl, a bunch of like dudes that were at like Forum. 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 5 years older and that's just not what I want to do. Like I'm just going to get a hotel or an Airbnb, right? So it's like, okay, 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 like 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? Like I think 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 like 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 and 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 the things you should put that money toward. Um so that's that is the Jack Raines philosophy on like life cycle of money.
