The Prof G Pod with Scott Galloway - The New Rules of Money in Your 20s — with Jack Raines

Episode Date: July 30, 2026

Scott Galloway speaks with Jack Raines, author of Young Money: A Field Guide to Wealth and Purpose in Your 20s, about why young people may be over-optimizing for retirement at the expense of actually living. Subscribe to Prof G+ to join our next livestream at profgmedia.com. And if you're not already reading Jack’s work, check out his Substack. Pre-order his book, Young Money, here. Algebra of Happiness: Start writing. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Episode 407 person is Erika for Central Florida. In 2007, Brittany Spears shaved her head. True story, I'm going to do a musical drama about a group of high school students who are just horrified at the least talented person in their class becomes a huge pop star. It's called Britney's Peers. Oh, I know. We need to do better.

Welcome to the 407th episode of the Prof Gipod. What's happening? In today's episode, we're sharing our live conversation with Jack Raines, substack writer and author of Young Money, a field guide to wealth and purpose in your 20s. If you don't want to miss our next live stream, which I'm sure you don't, or other content exclusive to substack, you can subscribe at profitingmedia.com. That's profiteamedia.com.

With that, we hope you enjoy our conversation with Jack Raines. Good afternoon and welcome to our Profi Plus live stream. Today, we're joined by Jack Raines, who writes the popular substack newsletter, Young Money, His new book, Young Money, A Field Guide to Wealth and Purpose in your 20s, is out next week. Jack, thanks for joining us. Scott, thanks for having me. So let's bust right into it. Our general advice here, Prop G, is that young people, or for young people to work life balance is a myth and that there's only tradeoffs.

And again, it's my way. It may not be the right way. But you think of your career as a projectile or a rocket. the majority of the fuel is expectorated trying to get out of the soupy inner atmosphere. And I feel that the same is true in your career. It takes a lot of fuel to establish momentum in your 20s and differentiate yourself and put your career on a trajectory such that once in space. And you get a lot, you can cover a lot of distance with a little amount of thrust. And that is the first million is definitely the hardest or the first 10,000 is hard.

and then the next 10,000 gets easier, and then I think it gets easier. So, and I would argue that some of those early tradeoffs early in life are worth it for the optionality and lifestyle it gives you later in life. Again, let me do my land acknowledgement. Not for everyone. A lot of people decide they want to work to live, not live to work. Anyways, Jack, your upcoming book Young Money preaches pretty much the opposite. And that is, young people should spend more time, save less, and chase the things they

actually want to do now. travel, start a business, move on a whim, while they're still young enough to enjoy them, rather than banking on doing it once, they're comfortable. In other words, don't optimize for financial stability when you're young. Tell us why you recommend that path versus the one I took and how you came to the realization in your own personal life. So I'll also make my own land acknowledgement that like if you have a lot of debt, completely ignore anything I'm about to say. It's probably a bad idea, blah, blah, blah. Like there's a lot of this comes from if you're in a place where you can do something differentiated or different, there's probably a lot of value in

doing that if you're young. If you're like $40,000 in credit card debt, $100,000 in student debt, you should probably pay off the debt. But to get to my main point there, I actually largely agree with you that setting the foundation for your career matters a lot in your 20s. And a lot of my advice for like doing other stuff and taking other risk isn't that different from what you're talking about in that because your burn rate is lower, you probably don't have kids, you're probably not married, you just have a ton of optionality in what you can do with your time when you're young, and you can try and experiment with a lot of different stuff. So like, my actual advice is less so about like you should work hard in your career or shouldn't work

hard in your career, but you should take shots that you probably won't be able to take later in life because you are going to have to be more risk-averse because you have kids or you have a mortgage, or your just taste and desires are going to be different. But there's a subset of things that you're probably going to want to do in your 20s that actually cost a lot less money to enjoy when you're young when you're older and also like you might not be able to do them when you're older. Like my version of this was I'd spend a year backpacking Europe and Latin America before business school and I was living in hostels and I had a blast.

You're like in a bunk bed with like 12 roommates. Again, I'm 29 now. It sounds horrible at 24. It was a ton of fun. And that was just a trip I really wanted to do, and I wanted to do it when I was young enough, like, I could enjoy the cheap thrill as an adventure. But to your point, I always had a plan where I had gotten into a good business school. I knew that, like, most of my career progression and earnings potential would come,

call it age 27 and after once I graduated from business school. So to me, it was like, I had this fun adventure I wanted to do in a very finite defined window when it made sense to do it, knowing there was an end date. So I went for it. What's your advice for navigating the tension between prudent financial advice, like building healthy saving habits with the optimized for good memories while you still can advise? I think debt is a big part of it, actually. Like if you don't owe anybody money and you're young,

you're actually in a good spot. Again, the way I think about it is like my first job, I made, I think like $56,000 working in corporate finance for UPS in Atlanta, which isn't that much money, but my rent was also $1,300, $1,300 in money. because again, I was in Atlanta, not New York, S,F, L.A. So my cost of living was just really low. Like, if I had to, I could have lived on like $2,000 a month, right? So at that point, if you're not making that much money, but your burn rate's really low,

I think it's a really bad tradeoff to skip out on like a fun night out with friends or a fun trip or just like doing that spontaneous thing that could create a fun memory when you're 23 or 24, knowing that you're going to be able to have the next 50, 60, 70 years of your life to look back fondly on that. Bill Perkins has a, in his book, Die Was Zero. He uses the term memory dividends to talk about, like, creating memories that compound over the rest of your life. I think you have like a really fun window in your 20s because like it's the first time you and your friends are making money. You're kind of responsible for yourselves out of the out of the house. You can sort of do whatever you want. Again, if you don't have debt, you can like take some of those shots and it's okay if you're not saving that. much, but the caveat is you want to put yourself on like a career path where your earnings can

scale quickly and exponentially, where if you're 23 and you're making $60,000, fine, but like, hopefully by the time you're, you know, 28, 29, you can get into $200,000 plus and you can, like, more than compensate for the lack of money you were making early. So it's, I do think focusing on, like, skill accumulation, building a network, putting yourself in any positions to earn more money matters. But if you're confident that you're going to be able to double, triple, quadruple your income, you shouldn't overly stress about not maxing out your 401k when you're like 23. You've also laid out fairly concrete money mechanics, spending a bigger share of small income earning or early. And as you said, ramping up savings as your income climbs rather

than front-loading investments at the expense of experiences. What's a standard piece of personal finance advice that you think is part of the conventional wisdom that might be wrong for young people. Maxing out 401K. I think it's like so, like I think me, the best like normal, broad advice is get on a path to pay off like high interest rate debt, whether that's credit card debt, expensive student loan debt, paying that off quickly is like the most important thing you can do, both from getting your finances right and just like mental well-being, not having that hanging over your head. But like when I, when I was in business school, I was working part-time, but I was also living in New York, and I was working for a media startup, and I wanted to do, like, fun business school stuff,

whether it was a trip for spring break or whatever. And if the trade-off was, okay, I could put more money back toward retirement, or I could go to Japan with my friends, I just, I think spending a few thousand dollars on the trip was worth way more than investing another $3,000 or whatever, and then maybe it's worth what, $4,4,500 now of how the S&P has grown. But I think that like the blind advice of like maxing out whatever retirement options you have, it's well intentioned, but it doesn't always necessarily make sense depending on where you are on life stage. Like you hit a point where there's only so much, so many more life expenses you can cut

before you hit your bare essentials. And I think most money problems are actually solved by making more money and increasing the margin of error that you have. And if you're like at the lower end of what your projected earnings are going to be over your lifetime, I think it's okay to like dial back contributions to retirement. In chapter nine of your book, and we're brothers from another mother here, you say, pursuing your passion is terrible career advice, which is something we agree with and say all the time. Why do you think it's bad advice?

Well, I almost did it, right? Like I love writing. My first job was corporate finance. It was pretty boring. It was also during COVID, which I think this is a whole other topic. but like people my age, like mid to late 20s who graduated into COVID, kind of missed that I'm 22 to 24, I'm in an office, just like being forced to do stuff.

I probably would have benefited from that. I think everybody is somewhat a product to their environment. They grew up in or kind of came of age in. My whole thing on the passion is like, so I love writing. And I started writing a travel blog and like an investing blog during the pandemic. I mentioned I went to go backpack Europe. I was writing about what I was doing abroad with my friends. and I was writing about crazy stuff going on in financial markets.

And my substack started growing. I was like, I should really double and triple down on the media thing. So I'm working for liquidity, the media finance, meme page, newsletter, all that during business school. And going into my second year, I wasn't really sure what I wanted to do. And I got a job off of Robin Hood to help them build a media startup called Sherwood News. And at the time, like the two things I'd really liked were investing in financial markets. and media and writing.

So I figured I should go all in on the content path. I've enjoyed doing this. This feels like the right move. And then I got there and realized that like I liked writing when it was just me blogging and putting my thoughts out there. And it was like this fun thing building an audience on my own platform versus when your paycheck is determined by your ability to like churn out columns and like you're in a more structured corporate environment.

I both didn't see the long term like income and career progression for me. and the traditional media setup. And I also realized that, like, the other thing I'd been really pulled toward, like, investing in financial markets, I found equally intellectually stimulating, but it was also just a much, like, both higher earning and higher optionality career path.

So, like, I work for a venture capital fund now. I pivoted. But the initial mistake I made was, like, I love writing, therefore I should make my career writing. When the actual way to think about it was, I built a good network from writing, how do I leverage that career-wise? Well, venture capital is a deal flow game.

I have a good network. I have access to founders starting stuff. Can I leverage the thing I built with my platform so I could apply it? It's a more lucrative industry and career path. And yeah, that was the pivot I made. So, like, I think passion is stupid because, one, if you're passionate about a thing,

it probably won't pay you well. And then even if you find a job in your passion and go after it, there's a very good chance you'll start to really not enjoy that passion anymore. it becomes stressful because you're trying to draw blood from a rock, trying to make money from a thing you used to do for fun. But there's probably skill sets developed in pursuit of that passion that are high leverage in other fields. So, like, figuring out how to leverage those skills or interest in something the market actually cares about is very important. It both makes you enjoy your

passion more because you can make it your free time. And then also you can apply things learned from it to something that'll actually get you paid. Like, I like making money. I think it's very okay to be like a capitalist and desire of money. Life is much better. with money than without money. And yeah, the pursue your passion is just like rich people tell people to do that once they already have money, right? Like it's easy to say it when you have like $100 million. It's different when you're just coming out of school or you're broke.

You write a lot about the concept of optionality as a depreciating asset. And I love this part. You argue that not pursuing it at all is a path to a midlife crisis because the people who spiral the hardest are the ones who committed to the wrong path too early. Say more. Yeah. So like I, optionality is interesting.

And like I'm 29 now. So like late 20s. In New York, people say I'm a baby. And Georgia, I should have like three kids already. Being from South Georgia, living in New York,

he's the full spectrum of lifestyle optimization. Something in this happens a lot in the New York, SF Bay Industrial Complex is like people keep doing thing to stack credentials to actually do the next thing. It's like the example of this is I go into banking to go to private equity to go to business school to maybe you pivot to consulting or you try to join a hedge fund or whatever. But you kind of just stayed on a track that has like the next step laid out without ever thinking about what you want to do. And the issue of that is like at some point

the the optionality path runs out and you sort of end up in a nurse that kind of just takes you to like whatever options are left after you play the optionality game. The flip side is some people commit to stuff really fast where you know you go to. to medical school because you just think you should be a doctor without deciding if you actually want to spend your time doing what doctors do every day. And then at like 22, you go to medical school and then you're in residency. And by the time you're out making money, you're in your early 30s, you have a lot of debt. And it's like, all right, I just put a decade toward this path. And I actually, if I thought about it a little more 21 or 22, might not have enjoyed in the

first place and could have redirected. So this is actually, I have a question for you. Do you think it's, you know, you're older than me. So you've seen a lot of people's lives play out. Do you think the people who, like, cut off their optionality too early and committed to the wrong thing had less life fulfillment? Or the people who, like, chased optionality, preservation into their 30s or 40s were worse off? Yeah, I'm sort of a – I'm a bit of a boomer on this. And a lot of it is proximity bias because the people I grew up with were like me. I was in a lower middle class. Most of my friends were upper middle class.

they wanted to do something that would provide economic security for them, which is a politically correct term, a way of saying they wanted to make bank. And what I think a lot of us found was that you can't hate something and make a lot of money at it because I went into investment banking. I hated it, and it hated me. And I was never going to make a lot of money doing it because if you hate something, you're just not going to be very good at it. But you can find, joy is the wrong word.

You can find satisfaction in something that may not seem like fun, you know, tax law. If you enjoy numbers, you get the certification, you enjoy applying the law to taxation, helping corporations and individuals figure out their tax strategies, it can be actually kind of intellectually rewarding. It's like I'm trying to solve a puzzle, and it pays really well, which is exceptionally rewarding, especially it gets more rewarding as you get older because these terrible things called kids and aging parents demand or really appreciate you figuring out a way to develop economic security such that you can start taking care of them. I would say that I think a lot of my, I don't think people want to admit it,

but I think a lot of people who went into the vanity industries and then had to start their lives later than the rest of us, probably regret it. I lived with and knew a bunch of athletes at UCLA, some of whom went to the Olympics, and they were calling me a 28 looking for a job. it's great to win a bronze medal at the Seoul Olympics, but I'm not sure if they were really honest with themselves

if they wouldn't have gone straight into the workforce at 22 and then just bought tickets to the Olympics. So I'm very much a pragmatist around this, and unfortunately I think the stories that are publicized are the people who turn away the corporate world or the boring job or their parents' advice, and they decide their dream is to open a restaurant. And I don't want to crush anybody's dreams,

my advice to people who are pursuing what I'd call a vanity industry, is sure, go into it, but have clear benchmarks for yourself that if I can't move out of my parents by the time I'm 24, it probably means my chosen profession is not working and I need to think about something else.

And if I want to be enacting, if I can't have my own health insurance within three years, then I should probably pursue another profession because 83% of actors don't qualify for health insurance because they don't make more than $23,000 a year according to SAGAFRA.

and I think I probably stuck with some stuff too long. I stuck with red envelope for 10 years, believing that I was bigger than the market, and if I just threw everything I had at it, eventually it would be successful, and the market was bigger than me, and the company folded in 2008 after 11 years post-founding. A piece of advice I would give to young people

is that you have to discern between quitting and when working just gets hard. I mean, the majority of jobs and companies are awful in the beginning. You're going to face injustice and ask yourself, all right, if I stick with it, am I making progress? And trying to balance that with, there is a time to throw in the towel and give up and say, okay, this just isn't working. Let's move on. And the biggest failures in my life professionally haven't been the biggest failure. I mean, arguably the biggest failure I've ever had was I've raised,

a ton of money to start an e-commerce incubator in New York. The problem is I raised the money in December of 99, and it was kind of over within three months. We just didn't know it, because there was never going to be any more capital for an e-commerce incubator in New York in 2000. The good news is I recognize that, and the market basically, I failed fast, and it was just like a blip in my life. Failing slowly, the worst thing that can happen to you is there's just enough signs of success to keep at it, and then you wake up after throwing yourself at something for 10 years. So success is the best thing, but failing fast is the next best thing. And if, you know, so what I would suggest is sometimes it's hard to read the label from inside of the bottle.

So assemble a kitchen cabinet such that you can discern the difference between, yeah, welcome to the work week. Just stick with it. You're doing well. It's hard, yeah, but don't resist the temptation to quit. Versus, boss, you've been at this. The market is telling you something. You should move on to something else. Any thoughts?

That's kind of like the original thing that put us on this thread is my thoughts on optionality. And it ties to being honest with yourself about timelines. Like young people have like the best asset you have in your 20s is optionality and like every facet of life. Like relationships, work, whatever. If you're like a 24 year old single guy, there's plenty of girls you can date. Actually, you're like, you're probably more valuable in the dating market.

Your late 20s and early 20s as you actually make money. It's much easier. to get a job because you can take a starter job pretty easily. Like, if you show that you are smart and driven and will work hard and people like you, they'll probably hire you and know that it'll take a year or two for you to get up to speed. So, like, again, if you find the thing that you're good at and you enjoy, whether that's like a job or a person, like you think should be your person and it's just like, you just know everything is good, great.

You find that at 24 commit. Awesome. A lot of people aren't like that. And it's okay to like, if you try a job for two years and then realize the market outlook is bad or you're bad at this thing and don't enjoy it, pivot and try a new thing. And you can take several shots on goal and basically every facet of your life when you're young. And ideally from that, you can accumulate a lot of experiences quickly that you can learn from and have a lot more touch points on. Okay, I had two or three different jobs in my 20s. I was really good at this.

I sucked at this. I really liked this. I've now developed like a much broader skill set, like almost like a Swiss army knife or generalist than I'd otherwise have. How do I apply these skills I've developed into one thing that can compound? And I think it's easy at like 26 to feel like you're falling behind the people who locked in on, I think at 22. But I would guess that like, you know, when you're 50 or 60, it doesn't matter that much if you found your thing at 23 or 27. And it's way better to have like tried a few things and found something you're really

committed to at 27 than just like pot commits the wrong thing at 23. whether it's a person and you get divorced or it's a career path and you're not where you want to be 10 years down the road. So like on optionality, it's like you should rapidly exploit that when you're young if you have any doubt on your path, knowing that like it's okay to spend a few years figuring it out. We'll be right back after a quick break. Support for the show comes from LinkedIn ads. There's no worse feeling than making a major investment in something only to realize it didn't exactly live up to the hype, such as buying a nice piece of tech that ends up in storage collecting dust,

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of winning, open only to legal residents of the 50 U.S. slash DC. 18 plus voidware prohibited by law. Sweepstakes ends at 11.59 p.m. Eastern Standard Time on September 15th, 2026. You argue that ambitious young people tend to cluster around a few sectors, finance, big tech, tech startups, law consulting, and then something such as tech sales is undervalued because it reads its low status. What do you think are some of the other things that young people might be overlooking for that same reason? So the tech sales one is funny because there's been this whole rebrand of calling sales go to market because nobody that went to like Yale wants to say that they do sales. If you join like, I don't know, like say you join Cognition on there, like they're one of the hottest like AI coding companies right now, right? If you joined as like an account exec there a couple of years ago, you've made so much more money. than somebody who's like in private equity and their fund is kind of trash and the carries

underwater. Like the idea of saying I'm an associate at KKR sounds really good because people in New York know what KKR is. Guess what? The person out there slinging like cognition to random like tech companies might have pulled between 500K and a million depending on what they're like OTE is. So there's like a real arbitrage and like being able to take a job that sounds less sexy to like the other kids who went to

Wharton undergrad, but you can make way more money. Like, the guy I know Sam Buck who joined Rap really early. He was a Goldman for a couple of years. He was just like basically an SVR at Rapp. And nobody really heard a rap. They're like Series A at that point. And guess what? Ramp's valuation

has like, I don't know, 50X since then. He's not like a very high up VP or exact there. It was sales. Like even before, like, even excluding the equity cop. Like, I'm sure he had a very good commission comp on that as he grew into it. So, like, I think sales jobs in general, unless you are, like, a dialed financial

markets, like, I want to be a trader or hedge fund analyst, I think your typical investment banker, consultant or, like, private equity associate could probably earn more money and enjoy their life more if they just leaned into doing, like, sales partnerships, whatever. I think there's other stuff, too, with, like, you were talking about being, like, a tax accountant. Accounting is another one where, like, it's boring. most people interested in finance would prefer to go into banking.

But if you can carve out a niche where you're doing taxes, estate planning, stuff like that and move up where you're dealing with higher and higher net worth clients, there's just so much money to be made. So, like, as a general rule, boring thing where, like,

you either have to be, like, social or, like, fairly good with numbers to do, and you don't think it would be that impressive to, like, tell a girl to bar, there's probably companies where you can join and do that and make a lot of money.

versus I would argue, like, private equity, which is still the hot finance thing, so much of the compensation is backloaded and carry. And like private equity is an industry. You could argue it was bloated. And a lot of their marks are unrealistic on their portfolio companies. Like, are you going to get any of that carried interest in eight years? I don't know. They keep raising continuation funds to try to keep the game alive.

But that's what everybody's still pattern matching to. So my hot employment take is like tech sales is probably a better bet than private equity for your typical investment banker. We'll see if I'm right in five years. You are right. I think the most overcompensated, if you think about relative to the structural risks they take or the amount of hours they work,

the most overcompensated people in our economy are the salespeople. And typically I found in the companies I've started, people hate them because they show up at nine, maybe 10, they're hungover, and they're reason. smart, but they're not geniuses, but they played with either the wrong toys or the right toys. And I can't figure out if good salespeople have especially lower, especially high self-esteem.

And I think 98% of the public isn't willing to sell. I used to knock on doors and sell magazine subscriptions when I was in high school. You know, it just, the ability to endure sales is something most people are not willing to do. Do not call me again. Oh, so you're saying I should call you back in two weeks, maybe. I mean, you have to be willing to get out such a big spoon and eat so much shit. And most people just aren't willing to do that. So as a result, the people who do bring some intelligence, some EQ can just make a shit ton of money. It's also funny because like in every industry at the top of the ladder, it's still like a sales job.

Like an investment world, guess what? Like at the end of the day, the actual boss is the LPs. The guy raises money. Yeah, yeah, yeah. Like you want to go raise $500 million. you're selling yourself, your reputation, your performance. Like, the whole, like, picking stocks or companies doesn't even happen if you can't convince somebody to give you the money in the first place.

The two people that run a hedge fund, the two partners are usually the two co-founders, are usually an introvert who sees the Matrix, who really understands investing, and then a high-EQ person who can go convince CalPERS to give them, you know, $100 million. And that's the chocolate and peanut butter. A few of your recent posts also covered trends that we talk a lot about here, Profji, that we're all informed but no one really knows anything, that optimization culture turns people into slaves with their metrics, and that publishing AI written work disrespects the reader.

Say more? Yeah, I mean, one of my favorite takes is like the whole, like I've never had a smart watch, right? Like, I think the entire, oh, like, my eight sleep said that I didn't sleep well last night. Now my day is going to suck. It's like, I don't know, man. I sleep on a normal mattress. And if I wake up and feel weird, I probably need to take a cold shower or, like, go to the gym.

And I don't know. I think this whole, like, metric obsession, especially with health is a little bit problematic. Because, like, you then start architecting your life around, like, how do I hit the right number versus, like, in an ideal world, the number informs you of like, oh, maybe I've been drinking too much. or she changed my diet. But in reality, the number starts driving the decision rather than informing it. And I just, I don't know. Like, we have so many metrics for everything. Health, like, you have performance data on social media posts that can lead people to, like,

audience capture if they're a YouTuber or a podcaster. You have, like, health stuff that can make people, I don't know, like, you can't really quantify how fun it is to have three beers with your friends on a Friday. But guess what? Like, my sleep score is probably worse on Saturday if I got a little bit drunk. but did I have fun? How do you quantify the, like, the social benefit of, like,

I don't know, like three Heineken's versus, like, getting the Heineken zeros. I think the trade-off's probably worth it if you don't have an, like an addiction or substance abuse problem. And the same things, you're talking about, like, AI and content.

It's like, there's such this performative influence which is like, I need to keep putting content out that, like, on Twitter, I know you don't really, you're X, I know you don't really post on there anymore, but there's a whole, like, and the VC startup world, the amount of obvious, like, clod slop that people are trying to be thought leaders on there,

I just don't read it. I don't read a single X article because it's probably just performative slop. That, I don't know, it's all just like, I think metric chasing and performance chasing without actually thinking through, like, how do I want to orchestrate my life

and what actual goal am I optimizing for is pretty dangerous because you can just find yourself running around circles and doing things and you're just like letting a number drive your life decisions rather than like lightly informant. You argue that where you live is an underrated driver of well-being and that every person should spend a couple of years in New York before having kids, which again, we also agree with. Talk a little bit about where you live being an underrated driver of well-being.

So I'm from a small town in South Georgia called Tifton. That has like 20,000 people. I love being from there, never want to live there again. It was just like deer hunting high school football. You go to church on Sunday. That's it. Fine. I lived in Atlanta, Georgia for two years after college,

spent a year kind of bopping around Europe and Argentina. And then I was in New York for two and a half years for grad school and right after San Francisco for a year. Now I'm back in New York. So like I've done small town USA, West Coast, East Coast. I'm a little bit bopping around everywhere. New York is my, like it's like my take on New York. York is one, it's my favorite city. I think if you're in your 20s, it's like just like scrap up, live with two buddies, get a three bed, one bath when you're like 23 and just make it work,

live in Murray Hill. You're going to have a blast because like you can go out every night. You're going to meet like so many interesting, ambitious people doing a little bit of everything. The density of like cool people you meet both for, that's useful for like work, just like general fun. You never know who you're going to meet at the club, the restaurant, the bar, whatever. your dating life, you just have so many more touchpoints at a time when, like, you should probably be your most social. And then for me personally, it's like, I've been here for a few years and it's still my favorite place because, I don't know, my apartment, like, this is a studio apartment in the background. It's, I paid more for this than some of my buddies do for their mortgages in, like,

the Atlanta suburbs. They have like three or four bedroom houses. Guess what? My studio is like $4,400 a month. That's like a house payment. But I'm not optimizing for like square foot. of a house. I'm optimizing for surface area touchpoints with like a lot of my friends who live in New York and like job opportunities and like girls I want to date. And New York is just the, it's like the gravitational center of life when you're in your 20s and even 30s versus like when I'm back home in Georgia, I'm bored. I feel like there's nothing to do. I go home. I love seeing my family for three or four days and then I'm kind of on this what's next. So I think it's like life stage, Like, there's a version of me.

San Francisco's the same way. I think it's one of the prettiest parts of the country. I also found it, like, really boring and a little bit monocultural when I live there. It's so, as a VC, it's very tech VC-centric. And, like, if I was married with kids and living in, like, Marin or South Bay or whatever, I might feel differently. But I just, like, didn't really enjoy the, like, day-to-day outside of work that much versus New York.

It's a lot more socially stimulating. But it depends. If you're more introverted than me, you might find New York over the way. and would prefer to live somewhere else. If I was, like, married with kids and wasn't at the point that I could afford, like, a very comfortable, much larger place to live, I'd probably move to, like, New Jersey or, like, further upstate or Connecticut or Long Island, right? But, like, the happiness boosts you get from being in a city that you actually like is so underrated.

I think a lot of people will make a decision I need to move somewhere for job without thinking about the hit on their, like, well-being. And if you aren't happy where you are, if you're not around people, you want to be around, you can double your salary, but you'll be twice as miserable, too. We'll be right back. Running a business shouldn't feel like surviving a software group project. One app for accounting, another for inventory, another for sales,

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Less time spent on operations, more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. The first ever all-electric 26 Subaru Trail Seeker is the EV for the Trail Obsessed. With up to 444 kilometers on a full charge and DC fast charging

from 10 to 80% in about 30 minutes in ideal conditions. Plus, ample ground clearance and symmetrical all-wheel drive make the 2026 trail seeker the most capable EV Subaru has ever built. Test drive it at your local Subaru dealer or visit Subaru.ca. We're back with more from Jack Raines. So you're VC now, but you've sort of gained traction or awareness. I'll imagine deal flow through writing and you spent some time in media. I'm curious to get your take on the media industry and the

greater economy. Yeah. So on the media industry, I think it's a, this might be a hot take. I actually think it's a very good time to start a media brand because you can just do stuff a lot leaner now. Like if you look at the radio industry, it's like there was so much infrastructure. You had so many people working in the studio versus now. You can launch a podcast and hit publish and effectively get distributed to the entire world

immediately. Like I know you have a whole team that works with you. That team is still probably way leaner than it would have been. 40 years ago to try to have the same level of distribution, right? So there's a lot of like, what I'd say is like bloated media companies that didn't really adapt to social media and now kind of influence your creator first stuff that like their revenue model and their cost structures doesn't really make sense. But for like individuals or lean teams, whether they're building subscription model, ad model, whatever, I think there's like a lot of value building in

niches with like a pretty low cost basis and low headcount. On the, creator front specifically, like the fund I'm at slow ventures, we actually have a, like, we have our fund that invest in startups, like tech, AI for whatever, yada, yada, yada, like Silicon Valley, New York, we do everything. We have a separate fund that invest in creators and creator-led businesses where the bet that we're making there is that the internet is getting more and more siloed where like I have my internet, you have your internet, like algorithms and interests drive everything. People that are kind of like cult leaders in different pockets have interesting opportunities to build businesses around their niche or their audience

where if you're kind of seen as the like market or industry leader on your thing and you have hundreds of thousands or millions of followers, can you build businesses on top of that platform? We think so. I go two ways where I think old media has like a just a revenue and expense problem. I think really scrappy entrepreneurs who like get the social media game and are down to run, like, lean teams can build businesses with their pocketing six to low seven figures a year. And I think we're hitting a point now where, like, pretty niche creators. Again, most creators aren't that entrepreneurial, but the ones that are that really get distribution, they based instead of having to pay for meta ads, they have it built in, right? So they're like,

go to market has a massive advantage. So like, I think if you can carve out, like, I have a niche and I have industry expertise in this thing. And there's a pretty interesting opportunity to, I would necessarily say building media business, but leverage podcast, YouTube, Twitter, LinkedIn, whatever. So just drive a lot of revenue. I'm curious, what role does AI play in your written work? How do you use AI?

So the number one way is like as a thesaurus. Like when I was working on my book, for example, I actually tried to do a couple of like, I know you've written several books. I don't know what your process is. This is my first time doing one. And I underestimated like how, mentally, like, strenuous writing a book is. It's not linearly more difficult than, like,

it's not 30 times more difficult than a blog post. It's the 30th of the link. It's like 300 times more difficult. It was my... Yeah, but my advice would be just keep out it so you can find out it gets worse. Yep. Yeah. I can't, I can't wait for the answer. It doesn't get better. But on the AI stuff, I actually try to do the like, okay, could I have voiced the text or rough draft faster and then manually edit it? Well, that didn't work. It's like, you have to wrestle with the sentences and stuff. So I actually tried to do so many versions of, like, can I accelerate the process? Like, I feel like there's a lot of self-published books that are probably written by AI

or even, like, regular books where, like, you know, that like 90% of books or whatever written my ghost writers, I'm sure there's some clawed in that. I actually, I was like, can it even, like, mimic my voice? It couldn't. I fed all my blog posts to, like, see what it can do. But the thing that AI was very useful for is very useful for is, like, minimizing the feedback loop of like getting some version of feedback on your thing. So like when I was working through like draft chapters, I'm going to do this in blog posts sometimes, I will, to be clear, I never let,

I've never published a single word of like anything I don't think that was AI written. But I will say like, hey, here's old writing samples. Like here's different drafts. Here's whatever. Now here's the one I'm working on. Tell me like where the voice is weaker than like other stuff I've written. Tell me if I'm like using an anecdote multiple times within this book. Tell me. Tell me. Tell me if the flow here doesn't. Basically, like, tell me everything that sucks about the writing and the weakest points and strongest points go. And then it's like getting an extra layer of feedback

where you disregard some of, you take some of it, and then you go back and workshop it. But, like, when you're writing your own stuff, it's hard to be objective about how good it is. When you give it to AI, it can just digest all of it immediately and point out obvious flaws where you can start working again faster. So, like, my human editor is phenomenal. I got to do a lot of micro edits between the,

human edits where I just got more feedback faster. And on my blog post and stuff, it's obviously a gain changer for research. Perplexity is very useful for pulling stuff quickly. Having Claudecodes synced up to my computer, I can pull from different files where I have different information on companies that I want to like query quickly. The information retrieval and review are just set up a lot is kind of the biggest thing. Yeah, if you disarticulated the different people or skills in writing, there's the writing itself. there's the fact-checking and the editing.

And then at the very beginning, there's the research. I find it's a good, if a good researcher, a great editor and a lousy writer. Yeah, you summed up my like three-minute monologue in about one sentence. But yeah, I agree with that. And what's next to you, Jack? I mean, hopefully sell like a million copies of a book.

I don't know. No, I mean, like right after this, we have our like partner meeting at the fund I'm at to talk about startups who might want to invest in. Like in general in life, it's like I think I'm always going to write. I don't think I'm ever going to have a like full-time media type of job again. But like I view writing as a like very useful cathartic way to like flesh out ideas and figure out what you actually think.

I think it like strengthens you mentally. And like ideally write more books, because I don't have the next one now. I also like the call it investing tech industrial complex of like all the developments in AI are like really cool. It's fun to get to talk to these founders all day, look at different deals. I try not to think like too, too far ahead on like what specific thing do I want to do as far as as as much as like being really opportunistic about like where are the like coolest, most interesting high leverage opportunities and this like broader tech investing space and kind of like stay in that funnel. At the end of the day, it's like if you're working in a broadly growing

market with really interesting people and really interesting stuff. I think there's like good financial outcomes there that are interesting. So that's kind of the game I'm trying to play. And then the keep the writing and the platform is sort of my differentiator and sort of business card. I'm like, this is who I am and how I think. If you want to work with me, you know, hit me up. Jack Raines is the writer of the newsletter Young Money. His new book, Young Money, A Field Guide to Wealth and Purpose in your 20s is out next week. In addition, Jack will be joining us in October to answer your questions on personal finance, wealth, and more. As always, you can send them to us at office hours of Proptochimedia.com.

Again, that's Office Hours at PropgMedia.com. And one last thing, if you'd like to join future live stream, subscribe to ProfgegegePt Plus at Propgumedia.com. And if you're not already reading Jack's work, check out a substack and pre-order his new book, which will link in the show notes. Jack, thanks for joining us. Scott, thanks for having me. Algebra of Happiness, no mercy of malice, the newsletter we put out every Friday turns 10. It initially started as L2 was a reinvention of my first firm, profit, but rather than being in a transactional model where I ended up selling the company for 2.8 times revenues,

I wanted a recurring revenue model. And the way we would try and predict renewal rates was through engagement. So we launched a series of media products, a video series called Winners and Losers, talking about digital innovation. and then I started a newsletter every Thursday night that went out to all of our clients. And I would talk about whatever was on my mind. It was part engagement with clients, but it was also a catharsis for me just to talk about whatever I wanted. And also I enjoy riding, and I'm fundamentally a lazy person, so I have a lot of self-imposed deadlines. And I think that,

again, success is a series of small acts of discipline. So every Friday, for the last 520 weeks, we have put out a missive. It can be on anything from engagement levels on SNAP to the valuation of Wii work to putting my dog down, which was the most red post of anything we've done.

We started with 200 subscribers. We're now 430,000. We don't monetize it. Occasionally we have an ad, but for the most part, it's sort of the center of our content flywheel, and that is it gives us ideas around books, chapters,

stories for one or more of our podcasts. But it's sort of my home base and kind of the thing I would argue I, I wouldn't say I enjoy the most. It's the most rewarding thing. Generally, the most rewarding thing and the hardest thing are the same thing. And that's what no mercy, no malice has been. And I used to write it every Thursday night, just me, after having a few drinks, I'm not proud of this, but I think some of my better posts were written when I was a little bit fucked up because I'm less guarded.

And I try to imagine that no one's ever going to read it, but my kids in 20 years. that hopefully they'll understand me and the world a little bit better and miss me and see how much I, you know, thought about and love them. And I know they feel that, but sometimes I think it'll be really rewarding for them to know that at some point in the future after I'm gone. And also just to be fearless and use it as a means almost like working out, supposedly, physically working out makes you live longer. But I think mentally working out keeps kind of Alzheimer's away, if you will, and I find that focusing on or trying to restructure that last sentence keeps me sort of a mental crossfit for me. Also, I do believe that the written word

is still the most powerful means of communication. And that is, I just don't think people are going to be listening in 10 years to any of these podcasts. I don't think they're going to be going back and thinking, well, I want to listen to that podcast from a decade ago. I do think there's a significant number of people, though, that will read a couple of my books. And then my son's will read my posts from decades earlier. And it's very rewarding to think that you're doing something that sort of immortalizes you. And that is, the medium is the message.

If someone comes up to me and high fives me, I know they saw a video. If they come up and start speaking to me as if they're my friend, I know they're a podcast listener. But if someone comes up and wants to talk about the loss of their mom or the balance between being a present father and trying to establish economic security, I know that they've read something.

And it's very, it's exceptionally rewarding. And I would, what's the lesson here? If you want to be a great communicator, if you want to be a great storyteller, which I think is the fundamental skill as it's the means of transmission for survivability, and that's why Mick Jagger gets to hang out with a 35-year-old ballerina

because he's an incredible storyteller. and artists get so much attention, it starts with a written word. If you really want to be a great communicator, I think you have to learn how to write well. Also, the idea, or essentially, if you want to immortalize yourself, if you want to live forever,

the only piece of advice that would have is the following. Start writing. This episode was produced by Jennifer Sanchez and Laura Jenaire. Cammy Rieke is our social producer. Bianca Rosario Ramirez is our video editor. And Drew Burroughs is our technical director. Thank you for listening to the PropGPod from PropG Media.