So I can't hear the book, see your blog without thinking about this.
Criteria compared to your career, just so good. So good.
All right, I won't let that go any further because I only have you for a short amount of time. But to me, that's like the obvious song for you in the book because it just like it just brings this awesome energy, which is what I associate with your writing and you. But I like I literally cannot think about the book without hearing that song. So I don't know if that was the song you thought it was going to be.
No, that's exactly what I thought it was going to be. I mean, it took me back to like the high school, college football locker room. The amount, the total number of hours of Lil Wayne I've heard both for and against my will is probably like too high to count at this point. Hilariously, when I launched my Substack, like I guess five years ago now, and called it Young Money, I actually Googled, 'Can Lil Wayne sue me if I call a newsletter Young Money?' And apparently, like trademarks or whatever apply domain by domain, and like book titles and newsletters are totally fair game for whatever, but I did look into that.
Nice. I was hoping there would be more of a surprise. I didn't know like age difference where Lil Wayne fell for you and then like that particular song. He's had a long career, but like to me that that was it. So I wanted to welcome you in with that with that track.
Awesome. Well, I set the stage on social media this morning. I gave you a heads up that your money is called or your book is called Young Money. I think most people will see it as a financial book, and it very much is, but I see it as a life book. And so the angle I want to take for a lot of the conversation today is more about life and kind of what you've learned and how that influences your relationship with money and what you're writing about. But with that being said, I want to kick things off with asking you, how do you like what does money mean to you? How do you define money?
So it's it's funny. I mean, I view money as just a like numerical value of things that you either can and will pay for now or you can and will pay for at some point in the future, right? So it's it's easy to hyper obsess over what's my income today, what's my net worth today. But money simply put to me is it's just this medium of exchange for literally anything right now. You could also say that like part of that is having money in the bank account providing a level of like security and freedom and flexibility. That in itself is an asset too, like just the ability to do things. It's not just what you exchange it for. But you know, I think a lot of personal finance and a lot of personal finance advice, books, podcasts, blog posts circle around like how much money should you be budgeting or how much should you be saving, but there's very little that goes into how much money should you be spending and how should you think about spending different amounts of money over different stages of your life. Like there are unlimited resources out there about saving for retirement, maxing out your 401k, but very little put toward which experiences and which expenses are, you know, going to give you a lot more life satisfaction in your 20s or in your 30s or in your 40s than later on. So for me, money really is just a medium of exchange for those things that you want. The thing that people should spend more time thinking about is what are the experiences and materials and like safety nets that I'm going to want to have at different points in life and then backing into how much money will I need at that stage and how do I get there both from saving and earning. But it should always start with what are the things you're going to want to do and then figure out how to make the money equal that amount.
From my standpoint, reading your work for a long time, having a chance to, we were just talking about before we started, meet you at Future Proof a number of years ago, which was really like for me, I was starstruck, which is this is kind of like I was telling you, it's kind of funny that
I'm because I'm like I'm older than you, so you think about like oh like I've been I was writing for a while, I had a podcast, not by any means was I like super famous by any means, but like you would think that the younger person might be starstruck by the older person, but you you were with Nick Maggiulli, run into each other in the middle of Future Proof and like you had to introduce yourself like yeah I know who you are and like you knew who I was and I was like oh man like Jack knows who I am, that's pretty cool. So I just wanted to let you know that like that the old guy was impressed, was like felt special that you knew who I was.
Dude, you're glazing me way too much, but I appreciate it.
But so look, but where I was going with that before I wanted to put that in is I feel like you have a pretty abundant mindset when it comes to money and finances and how you navigate life. And I'm wondering if your ability to see money through the lens that you do, just as, you know, a form of currency and the way you kind of described it, do you think that that helps you have more of an abundant mindset to where money is not this really? I mean, it's important, but it doesn't sound like it it it rules your thinking, it rules your decision-making. Do you think that helps you navigate life the way you do?
So I think the abundant mindset's a good thing to flag. I mean, I feel like it's funny. I live in New York City, right? This place is expensive. Like I am in my studio apartment. You can see like there's a couch back there, bed behind me, whatever. And I'm paying more for this than a lot of my friends do for their mortgages in like Atlanta where I lived for a few years. So money is top of mind for me and that my cost of living is higher than it would be in other places and I need to make a certain amount to maintain that. I do think a lot of people get hyperfixated on okay like I say I'm in my mid to late 20s applying for a job. There's this salary band for that job and then this salary band for another job. I've just I've seen enough people make money from different versions of entrepreneurship, equity in the right companies, basically just staying in the game long enough and doing good stuff where eventually there were windfalls from it that I just view money as a pretty fungible asset where if you just keep putting yourself in and around where money's going and keep accumulating social capital, opportunities to turn that into financial capital will arise. So I've never like I've I've definitely been thoughtful about my career and I wrote about it in the book how I had like a career change a couple of years ago to open up more of those hopefully higher income opportunities down the road. But yeah, I think having an abundant mindset's important. If you have a scarcity mindset when it comes to money, you are and you're always focused on the bottom line rather than increasing the top line, I think you're going to shrink away from opportunities that might not be as obvious, right? I've just I've never doubted my ability to make money over the course of my life and my ability to at different life stages be able to like accumulate the amount of money I'll need to keep like basically subsidizing what I want at that point in life, right? But a big part of that is being like very self-aware of the things that you want and the things that you don't want. Where in New York particularly, you can get caught up in the rat race of spending more money than you should, going into credit card debt just to play the like status game, going to the right clubs, getting a nicer apartment than what you actually need at that stage in life. And I've tried to shy away from that, which makes it much easier to, you know, keep your eyes open for opportunities to make more money. What I never wanted to do is I never wanted to sacrifice things I really cared about at certain stage in life for the sake of this might be a little bit too expensive. I just don't think that's a good way to go about living in 2026.
I think abundant mindset people think it's harder to have and obviously there's circumstances and family narratives and things that kind of shape the way we view things. But the the thing you said that I want to highlight when it comes abundant mindset is just this understanding that money is fungible. So I have something later on that I'll bring up now. Like I believe that money is it's a form of energy and and it's it's a current. It flows. And I think there are things that we can do to control the flow of money to and to and through us. So there are things we can do and and ways we can look at life that we can bring more money to us if that's what we need. And I just think having that understanding that there are like yes, you could be boxed in in one regard, but there's other things you can do and other opportunities out there where you can go increase the flow of money to you. And just having that understanding and having that belief allows you to see possibility. So I think abundant mindset I don't think is as difficult as people might think it is when you just understand that there are opportunities we all have to go make a little bit more money and other ways to flow it to us. But then another thing you said is you didn't say the word, but a big word for me is alignment. Like the podcast is Aligned Life and from the reading and other podcasts I've listened to, you have a very very good understanding of what matters most to you so that you can allocate your resources towards that. And I think those two things, understanding that money we we may have more control over the flow than we realize and that when we operate in alignment, it makes it a little bit easier to allocate resources when it comes to us.
Yeah. I mean I for me in my call it early to mid 20s I was I was I think there's two ways to play your 20s and neither of them is right or wrong but they put you in different spots once you hit your late 20s to early 30s. There's one which had I gone to like a stronger undergrad school like say I've gone to like an Ivy League or like a UVA or Michigan or something like that for undergrad, very good chance I get on the investment banking train making like $150,000 out of undergrad and then you can accumulate financial capital very very quickly in your 20s compared to other career paths where you can give yourself some financial flexibility in your late 20s to either double down on that or take your foot off the gas and do something different. I went to a non-target undergrad school. I went to business school at Columbia to basically compensate for that and graduated at 27. But for my early to mid 20s, there weren't really any super high earning career path opportunities for me, particularly because I knew I was going to go to business school in a couple years. So I treated my early to mid 20s as accumulate as much social capital as possible and candidly have as much fun as possible for life experiences that you can only have at 24 or 25, knowing that with like the way that my life is kind of set up right now, the financial opportunities are probably going to start hitting my late 20s to early 30s and I'll be able to recuperate call it the the financial payouts that I missed at 25 or if I'd gone to a different school maybe I would have had access to. So what that meant for me was I write about it in my book, but a year before business school, I quit a job I didn't particularly like and backpacked Europe and Latin America for a year, which sounds crazy or scary, but I was spending maybe $15 a night on lodging to like stay in a hostel with strangers. I was spending nothing basically on food and drinks. And then I found a part-time gig working for a media startup online that basically subsidized my lifestyle where I wasn't saving anything, but I wasn't spending down my bank account either. And the opportunity cost of that was probably missing out on 50 to $60,000 of additional income, which in my head didn't really wouldn't move the needle on my lifetime earnings nearly as much as what came after business school. So when you talk about alignment, I kind of realized I had this finite window of like high optionality fun and I could go after where I would have opportunities to earn more money later versus if I try to double down on the money at 24, 25, it would still pale in comparison to how much I would make later. But the opportunity for the fun crazy stuff that younger me wanted to do, I just wouldn't be able to do later. You you know, you get older, the the prospect of getting married, having kids, buying a home, all that becomes more real, and you're not going to be chasing the cheap thrills like you used to. So younger me was really aware of the opportunity set he had and like how cheap it was to build memories that I would enjoy for years and I kind of sprinted at that. I don't necessarily think what I did was better or worse than people who choose a different path, but I do think you should be really aware of the time and money tradeoffs that you're choosing at any point in your life where I'm much more financially motivated now than I was call it four years ago. I also have much more lucrative opportunities around the horizon for me over the horizon for me now than I had at 24, right? So I should be and I just think a lot of people really only focus on the money part and not the tradeoffs and experiential part that comes along with that. Like there's there's no free lunch in any of this, particularly when you're young.
What growing up shaped your your perspective on life to where you realize younger you realized, hey, I don't have these opportunities. The next couple of years of working really isn't gonna make that big of a difference. Let me go do these things that I really want to do. Like I talk about living authentic lives. Like you were living your authentic life. You had the confidence to go do the thing you wanted to do even though it was against everything that we're taught growing up. So what was it that like is there anything you remember growing up? Anybody who influenced you? Like what helped you develop that mindset to say this is how I'm I'm going to prioritize doing what feels right to me versus what I'm told I'm supposed to do?
Yeah. I mean I was pretty fortunate that most people in my family are fairly entrepreneurial. My dad went to law school. He practiced law for a few years and then he hated it and him and his brother bought a couple of there's a company called Aaron's. They sell rent-to-own furniture. They used to be publicly traded. I think they got bought out. Anyway, they bought a couple of those stores and as of today they they operate somewhere between 10 and 15 of those in Little Rock, Arkansas and the surrounding Arkansas western Tennessee area. Super random. Like I grew up in Georgia, they owned furniture stores in Arkansas and we had a farm and they would sell like pine straw, timber, soybeans. But it wasn't like a nor it's not like my dad was on some corporate ladder. And then my mom used to be a school teacher. Then she was an interior decorator. Like she and her mom and her grandma had always been like painters and really artistic and she built a book of business from that. My grandpa started his own insurance company. Like all of my family models had just pretty differentiated somewhat idiosyncratic careers and I had like a decent lifestyle as a kid. So I my pattern match for what was normal was not you try to be VP of this and then director of this. It was kind of there's just a lot of ways to make money. And when I was 11, my grandma, my paternal grandma, Mama Ruth as we call her, she I write about this in the book, but she told me, 'Hey, I want to take you on a trip.' Like I I traveled a lot with my grandparents as a kid. My grandpa would have board meetings. They would bring me I would just bring my Game Boy and then like hang out with my grandma and it was great. And she said, 'I want to take you on a trip anywhere in the world you want to go, just to name a spot.' And you know, I had never left the United States before. I had a big map on my room as a kid. I was an Animal Planet, National Geographic geek. And I loved like Africa, Asia, Latin America. I knew the capital of like every country. And initially I said, 'Somewhere in Central America.' And she said, 'No, no, no. We can go anywhere.' And I said, 'Okay. I want to go to Tanzania. I want to go on a safari. I want to see all these animals, elephants, rhinos, giraffes.' And to her credit, which is like seemed pretty crazy at the time, my late 60s grandmother took her 11-year-old grandson to Tanzania for two and a half weeks and we had a blast. And after that, a few years later, when I was in high school, I asked her why she did that in the first place. Cuz since then, she took my little sister and I was the oldest cousin, like all my cousins on similar trips. Mine was the coolest, but everybody got to go on one. And she said that she realized, you know, in her 60s she was getting older and she could either leave her money to her family after she died or she could spend some of it on her grandkids while she was alive. And she figured there would be she figured it was just a much better use of money to spend it on creating fun memories while she was alive. And that kind of stuck with me and my framing on money is only worth what you eventually exchange it for. That's where I got that idea from. And it's something that stayed top of mind where you can always accumulate more money. You can always spend the money that you have, but being thoughtful on when and how you want to spend it just matters a ton. So I was fortunate that like in my formative years, I got a lot of exposure to what I think is a much healthier relationship with money.
I have this conversation with a lot of my retired clients about, hey, you've got more than enough money you're ever going to spend. Would you rather give it away when you're not here or you know die with a little bit less and be able to enjoy some of these experiences with the people you love or even just see the fruits of your labor of like okay you're going to give it away be there to be able to see the impact rather than be looking down and see the impact and it's something that I'm glad your grandmother figured that out because a lot of people have a hard time doing that like you figure the reason they get in this position is because they have one set of behaviors and where we're trying to get them to go is the other end of the spectrum and spend more. It's it's tough for people to do that. So I see that all the time. So it's cool your grandmother picked up on that.
So we there's another currency that I that we have in life and you talk we've touched on a little bit but to me it sounds like time is a very important currency and I think of it as a currency because we do spend it. And unlike money I don't it doesn't flow to and through. It's like it it it's depreciating all the time. So
It feels like it's accelerating all the time too.
Yeah. Yeah. So tell me tell me about your you know your view on time and why that's so important to you.
Money and time are like I would say that money and time are kind of the the the two the two currencies through which the rest of our life flows, right? Like you like you spend money to acquire things and then you're spending time whether or not you're conscious of it. Like every single action we take and decision we make has some time cost, right? Like it's it's the one fully finite, you know, time is the finite asset that like you will spend to zero regardless of whether or not you want to. Money is the the fungible renewable asset that like can go up and down and back and forth over the course of your life. Something that I'm increasingly aware of is time seems to accelerate the older you get. I'm not particularly old. I'm 29, but 28 went by faster than 27 or 26. And I do think injecting bits of novelty into your life help slow down the passage of time a little bit. But time slows down as you get f it time speeds up as you get older and older is something that I'm like increasingly aware of. You hear it as a kid that time is flying and you think that that's stupid because you're 10 years old and it seems like the school day drags on forever and then you know you're 29 and you blink and half the work day is gone or the week went by or here we are at the end of August and it's almost 2027, right? The the more I'm not the first person to bring that up. The the thing that I think is more interesting when it comes to time is that time also makes life very stage specific because as we move through time, you're not actually the same person at like a later point in time than you are when you're younger. Like you have the same DNA, the same name, but your values and priorities and desires and responsibilities just shift a lot with the passage of time. And that impacts the things that you're going to want to spend money on. So, you know, the example being when you're 23 or 24 and you're living with a couple of roommates and you're sharing a bathroom and like you have no money, but life is otherwise fun. And your idea of fun is like going out for dinner with your buddies and then finding like a cheap dive bar to spend the evening at or like going back to your alma mater for a college football game. None of that costs that much money and those like cheap experiences are a ton of fun to spend money on. You fast forward 10 years and you're 33 or 34. All the stuff you enjoyed doing at 23 or 24 probably sounds miserable or at least like Sisyphean, right? Like it's not it's just not your priority anymore. So knowing that your desires and optimal behaviors are going to shift depending on which stage of life you're in will also change how much money you want to have and how much you'll be willing to spend and what you'll want to spend it on at those stages in life. So you almost like I take the approach that you can kind of like you can almost think of your life like a timeline where you can divide it into stages by decades, five years, whatever and kind of work backwards from you know you can adjust like you can make inflight adjustments along the way but how much money do I think or what things do I think I'm going to want to do and will prioritize at this stage in life like when do I think I'm going to get married, have kids, own a home, how long do I want to work and as you work backwards from that you can start to slide in like how much money do I think I will either need to have or be earning at these stages in life to like make that a reality and you know it's like life planning people talk about retirement planning a lot and like career planning a lot but this entire like how am I Jack Raines going to change over the passage of time and how will that impact the amount of money I need to make and what I want to spend it on is just I think it's an underdiscussed phenomenon.
I think what you described is something to to consider and also I think you need to be directionally right. Meaning okay as you're reversing back you're trying to predict what future Jack is going to want and you know what today's version of Jack would want in the future but between now and then there's going to be experiences that you have that expose you to things you never knew existed that's going to change. So the way I think about it is with myself and also with the planning like life planning is what I do now like yes I'm a financial adviser but I want to talk I talk way more about the life that you as the individual want and then we can align finances later. So we just need to know directionally where we're going to go, but then remain open to what life brings us and not be too fixated on this is where I want to be when I'm 45 because maybe you end up being somewhere totally different, which is where you're supposed to be. And if you're too fixated, you miss those synchronicities of life. So you miss those random conversations that lead to something else because you're so laser focused. And I think it kind of goes against it's it goes against how we're taught to plan like know exactly what you want like even down to the dollar amount be so fixated on that and move towards it and there's benefits of being that way but I also think if you get too fixated and robotic you miss out on some of the cool things in life that bring you opportunities you'd never I mean I would say that your life is very much that way like had you not been open to go travel and things that happen who knows if you would have met this person that introduced that person and who knows how it changes your future. So I think that the my recommendation or my thing to consider would be think directionally where you want to go so you have a direction to head. Do the things to move in that direction but also be open to the experiences and the connections that life brings you that might take you a little bit different.
Totally. I mean, serendipity is the best thing in life, right? Like I I would I would say that most people's like whether it's meeting your future spouse or employer or best friend or business partner, like you you just can't you can I take two sides to it. You can put yourself in positions to like optimize for these good things happening like it's it's almost a trope at this point, but increasing your surface area for luck. Like being direction like that's my way of thinking about being directionally like like putting yourself in the right direction is how do I keep myself exposed to the opportunity sets that I want. But yeah, leaving wiggle room where you know 25-year-old you probably doesn't actually know what 45-year-old you is going to want to do, but if you keep working hard to go in the right direction, those opportunities will present themselves to you over time.
And how are you balancing preparing for the future knowing that we need to, but also maintaining the ability to have these moments and have joy and have fun today? Like how do you how do you balance the two?
Yeah, I I have a compared to even like four or five years ago, I'm I have a much clearer idea of what I'm prioritizing now and then which things in life are negotiables and which ones aren't. Like the things that aren't right now. I I'm from Georgia, lived there for 25 years, moved to New York for a couple of years. I moved to San Francisco for a year for work and it was I was making a career pivot from media into venture capital. I had very little leverage when it like I was offered a job based in SF. I didn't know if I'd get that job if I like stipulated I need to be in New York to do this. I moved to San Francisco. I've done a good job at the fund I'm at. They let me move back to New York. That's where I live now. I would like to stay in New York for at least the next three or four years because I look at it like I'm single, I'm 29, there's a bunch of personal reasons to want to be here. Namely, there's a lot of other young, single, fun people, both like friends, you know, potential partners, and
There's just the surface area for like running into other fun, interesting young people is much higher here than anywhere else. I don't really know if I would want to raise a family here. I'm very open to staying in the New York area or moving. Like that's not a... I am not one of the 'I have to be in Manhattan my whole life.' I don't really... it's not a priority. But I do care about being here right now because I don't think there's anywhere else in the world that I would enjoy as much for the rest of my late 20s and early 30s as New York.
So like on the flip side, career stuff, I really like working in venture capital. I like investing. I like tech companies. I don't know if I'll stay in an investor seat forever. If there's like a good opportunity with a cool company and I like the founder, or if I want to start my own thing, I'm very open to any version of where's the most interesting opportunity for me within this broader sphere of developing tech. Like four years ago, ChatGPT hadn't launched. Since it came out, there's companies that didn't exist that are worth billions of dollars, right? Like you can't over-plan what that looks like or even what investment groups look like and how they're allocating money. But staying at the cutting edge of what's going on at AI, which tech companies are working, how are investors thinking, I think that'll just keep putting opportunities in front of me that are interesting.
So it's like on the career thing, I want to stay in New York. There's a ton of opportunities in New York and there's new stuff popping up every few months. I know I want to live here. I'm a lot more malleable on the 'do I want to be an investor, would I want to join a company, would I want to start my own thing.' I don't try to over-architect the specific thing, but I do know I want to stay within a broader sphere of like tech and investing and blah blah blah. So I think just having like a clear set of 'these are the things I have to do, these are the broader areas I'm interested in,' but I'm willing to fit wherever I think is opportunistic matters. Like you should have some boundaries and some code on what you're willing to do and willing not to do, but your entire life can't be black and white rules. It's like bowling. You need like gutter blockers, but the ball still needs to be able to move a little bit.
So as you navigate kind of with that mindset in the past and going forward, like you've made some major life decisions again that appear to be what you felt was best for you in the moment. How do you go about navigating these decisions? Like, I'm a big believer in intuition. I've learned that not everybody has the ability to read their intuition as natively as I have, but like how much do you rely on your gut feeling? How much do you rely on looking two steps out and trying to plan your way? Like what's your decision-making process as you navigate? And the reason I want to ask that is as I observe you from afar, you are the epitome of somebody living their authentic life. You show up authentically in everything that you do, to the cowboy hat on the book, to the posting you used to do on LinkedIn that almost got you in trouble at Columbia.
It's funny that you say that, and we can talk more about that in a sec, but the dean of students who I had to meet with over that got an early copy of my book and she loves it. So this has worked out pretty well for me, but yeah, that did happen.
