The New Rules of Money in Your 20s — with Jack Raines

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

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

• 0:00Speaker 00

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• 0:31Speaker 00

  Hogging seats on a crowded train, not saying, excuse me, watching videos on your phone with no headphones in. Sometimes it feels like we don't know how to act anymore.

• 0:42Speaker 01

  What we have been seeing increasingly is people breaking rules. Why should I play by the rules if nobody else is going to do that for me?

• 0:51Speaker 00

  This week on Explain It To Me, how to mind your manners. New episodes, Sundays, wherever you get your podcasts.

• 1:01Scott Galloway?

  Episode 407, Person. Missouri State for Central Florida in 2007, Britney 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.

• 1:22Scott Galloway?

  Ah, I know, we need to do better. Go, go, go.

• 1:34Scott Galloway?

  Welcome to the 407th episode of the Prof G Pod. What's happening? In today's episode, we're sharing our live conversation with Jack Rains, 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 profgmedia.com. That's profgmedia.com. With that, we hope you enjoy our conversation with Jack Rains.

• 2:07Scott Galloway?

  Good afternoon and welcome to our Prof G Plus live stream. Today, we're joined by Jack Rains, 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.

• 2:23Speaker 03

  Scott, thanks for having me.

• 2:25Scott Galloway?

  So let's bust right into it. Our general advice here at Prof G is that young people, or for young people to work, life balance is a myth and that there's only trade offs and that, you know, and again, it's my way, it may not be the right way, but you think about 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.

• 3:09Scott Galloway?

  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 it gets, I think it gets easier. So, and I would argue that some of those early trade offs 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.

• 3:54Scott Galloway?

  Tell us why you recommend that path versus the one I took and how you came to the realization in your own personal life.

• 4:00Speaker 03

  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 it's against my main point there. I actually largely agree with you that like, 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 risks, 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

• 4:43Speaker 03

  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, you have a mortgage, or your just tastes 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 they well older, when you're older. And also like, you might not be able to do them when you're older. Like my, my version of this was, I spent a year backpacking Europe and Latin America

• 5:27Speaker 03

  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 thrills and 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 at a very finite, defined window, when it made sense to do it, knowing there was an end date, so I went for it.

• 6:07Scott Galloway?

  What's your advice for navigating the tension between prudent financial advice, like building healthy saving habits with the optimize for good memories while you still can advice?

• 6:15Speaker 03

  The, 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, 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 $1,200, $1,300 a month, because again, I was in Atlanta, not New York, SF, LA. 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 trade off 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

• 7:00Speaker 03

  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 With 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, and 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,

• 7:43Speaker 03

  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 a position 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.

• 8:11Scott Galloway?

  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, is part of the conventional wisdom that might be wrong for young people?

• 8:32Speaker 03

  Maxing out 401K, I think it's like, so, like, I think the, 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 wellbeing, not having that hanging over your head. But like, when I, like, 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.

• 9:16Speaker 03

  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, $4,000, $4,500 now of how the S and 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 in 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.

• 10:00Scott Galloway?

  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?

• 10:10Speaker 03

  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 nother topic, but like, people my age, like mid to late twenties 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 of their environment they grew up in or kind of came with age in. My, my, 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

• 10:55Speaker 03

  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 Robinhood 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 had 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

• 11:39Speaker 03

  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 in the, call it 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

• 12:21Speaker 03

  starting stuff. Like, can I leverage the thing I built with my platform so I could apply it to a more lucrative industry and career path? And yeah, that was the pivot I made. So like, I think, 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 like, 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 interests in something the market actually cares about is very important. It both makes you enjoy your passion more because you can

• 13:05Speaker 03

  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 money. Life is much better with money than without money.

• 13:19Speaker 03

  And yeah, the pursuit of passion is just like, rich people tell people to do that once they already have money, right? Like, it's, it's easy to say when you have like a hundred million bucks. It's different when you're just coming out of school or you're broke.

• 13:29Scott Galloway?

  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?

• 13:47Speaker 03

  Yeah. So like, I, optionality is interesting. And like, I'm 29 now, so like, late twenties. In New York, people say I'm a baby. In Georgia, I should have like, three kids already. Being from South Georgia, living in New York, you get the full spectrum of lifestyle optimization. Something, and this happens a lot in the New York SF Bay industrial complex, is like, people keep doing things to stack credentials to actually do the next thing. It's like, the example of this is, I go into banking to go into 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 with that is like, at some point, the,

• 14:32Speaker 03

  the optionality path runs out and you sort of end up in, a nurse 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 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 that I actually, if I'd thought about it a little more at 21 or 22, might not have enjoyed in the first place and could have redirected. So, I actually, 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

• 15:16Speaker 03

  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?

• 15:28Scott Galloway?

  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 the 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. Yeah. And what I think a lot of us found was that, you have to, you can't hate something and make a lot of money out of 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

• 16:10Scott Galloway?

  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 was trying to solve a puzzle and it pays really well, which can, 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

• 16:51Scott Galloway?

  industries and then had to start their lives later than the rest of us, probably regret it. I lived and with and knew a bunch of athletes at UCLA, some of whom went to the Olympics. And they were calling me at 28, looking for a job. And sure, 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, you know, turn away the corporate world or the boring job or their parents' advice, and they decide

• 17:33Scott Galloway?

  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 call a vanity industry, is sure, go into it, but have clear benchmarks for yourself. That if, 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 in acting, 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 SAG-AFTRA. 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

• 18:16Scott Galloway?

  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, you know, 11 years post-fa, 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.

• 18:55Scott Galloway?

  And the biggest failures in my life professionally haven't been the biggest fail. I mean, arguably, the biggest failure I've ever had was I 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.

• 19:36Scott Galloway?

  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?

• 20:04Speaker 03

  That's kind of like, like the, the original thing that put us on this thread was my thoughts on optionality and it's, it ties to being honest with yourself about timelines. Like, young people have, like, the best asset you have in your twenties is optionality in 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 twenties and early twenties, 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

• 20:48Speaker 03

  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 found 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 touchpoints on. Okay, I had two or three different jobs in my twenties. I was really good at this, I sucked at this, I really liked this. I've now developed like a much broader skillset, like almost like a Swiss army knife or generalist than I'd otherwise have.

• 21:33Speaker 03

  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, 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 commit to 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.

• 22:18Scott Galloway?

  We'll be right back after a quick break.

• 22:27Scott Galloway?

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• 23:12Scott Galloway?

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• 23:29Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch up when audit season comes around again. Vanta works differently. The regentic trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

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• 24:36Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch up when audit season comes around again. Vanta works differently. The regentic trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 25:21Scott Galloway?

  Over 16,000 fast-growing companies like Ramp, Ryder, and Harvey save time and resources while scaling fast with Vanta. Learn more at vanta.com/provg and get $1,000 off. That's spelled V-A-N-T-A dot com slash prof G for $1,000 off.

• 25:48Scott Galloway?

  You argue that ambitious, young people tend to cluster around a few sectors, finance, big tech, tech startups, law, consulting, and that something such as tech sales is undervalued because it reads as low status. What do you think are some of the other things that young people might be overlooking for that same reason?

• 26:08Speaker 03

  So the, the tech sales one is funny because there's been this whole rebrand of like, calling sales go to market because nobody that went to like Yale wants to say that they do sales. The, if, 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 a, 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 carry is underwater. Like, if the, 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 their like OTE is.

• 26:53Speaker 03

  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, um, the guy I know, Sam Buck, who like joined RAP really early, he was a Goldman for a couple of years. He was just like, basically an SDR at RAP and nobody really heard of RAP. They were like series A at that point. And guess what? RAP's valuation has like, I don't know, 50X since then. He's now like a very high up VP or exec there. It was sales, like even before, like even excluding the equity comp, 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,

• 27:35Speaker 03

  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, like you were talking about being like a, 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 like, move up or you're dealing with like 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 sociable or like fairly good with numbers to do, and you don't think it would be that impressive

• 28:20Speaker 03

  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 is bloated and a lot of the, 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, keep the game alive, but... That's what everybody's still pattern matching to. So my, 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.

• 29:00Scott Galloway?

  You are right. I think the, the most overcompensated, if you think about relative to the, well, 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've found in the companies I've started, people hate them because they show up at nine, maybe 10, they're hungover. And they're, they're, they're reasonably smart, but they're not geniuses, but they played with either the wrong toys or the right toys. And they have, I can't figure out if good salespeople have especially lower, especially high self-esteem. And I, I think 98% of the public isn't willing to sell. I used to knock on doors and sell magazine

• 29:41Scott Galloway?

  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, you're saying I should call you back in two weeks, maybe. I mean, you have to be willing to, 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.

• 30:11Speaker 03

  It's also funny because like in every industry, at the top of the ladder, it's still like a sales job. Like investment world, guess what? Like you, like at the end of the day, the actual boss is the LPs and like

• 30:21Scott Galloway?

  The guy who raises money.

• 30:22Speaker 03

  Yeah. You, 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.

• 30:35Scott Galloway?

  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 cowpers to give them, you know, a hundred million dollars. And that's the, the chocolate and peanut butter. A few of your recent posts also cover trends that we talk a lot about here, Prof G, 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?

• 31:12Speaker 03

  Yeah. I mean, I, one of my, one of my favorite takes is like the whole, like I've never had a smart watch, right? Like I think the, 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, 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, like maybe I've been drinking too much. You should change 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

• 31:57Speaker 03

  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? Like, how do you quantify the like, the social benefit of like, I don't know, like three Heinekens versus like getting the Heineken zeros? I think the trade-off is probably worth it if you don't have like a, 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. There's like, I need to keep putting content out

• 32:42Speaker 03

  that like, like on Twitter, I know you don't really, or X, I know you don't really post on there anymore, but there's a whole like, in the VC startup world, the amount of like obvious, like Claude slop, that people are trying to be thought leaders on there. I just don't read it. Like I don't read a single X article because it's probably just performative slop that, I don't know. It's, 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 in circles and doing things. And you're just like letting a number drive your life decisions rather than like lightly inform it.

• 33:23Scott Galloway?

  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, we also agree with. Talk a little bit about where you live being an underrated driver of well-being.

• 33:39Speaker 03

  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, and a little bit bopping around everywhere. New York is my, like it's, like, my take on New York is one, it's my favorite city. I think if you're in your twenties, it's like, just like scrap up, live with two buddies,

• 34:20Speaker 03

  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, 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

• 35:05Speaker 03

  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 footage 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 twenties and even thirties versus like when I'm back home in Georgia, I'm bored. Like 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 specific. Like there's a version of me. San Francisco is the same way. I think it's one of the prettiest parts

• 35:47Speaker 03

  of the country. I also found it like really boring and a little bit monocultural when I lived 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 overwhelming 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,

• 36:28Speaker 03

  the, the happiness boost 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 a 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.

• 36:49Scott Galloway?

  We'll be right back.

• 36:58Speaker 00

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• 37:28Scott Galloway?

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• 38:40Scott Galloway?

  We're back with more from Jack Rains. So you, you're VC now, but you've sort of gained traction or awareness and I imagine deal flow through writing and you, you spent some time in media. Just curious to get your take on the media industry and the creator economy.

• 38:57Speaker 03

  Yep. So on the, 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 influencer creator first stuff that

• 39:39Speaker 03

  like their revenue model and their cost structure just doesn't really make sense. But for like individuals or lean teams, whether they're building a 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 invests in startups, like tech, AI for whatever, yada, yada, yada, like Silicon Valley, New York, we do everything. We have a separate fund that invests in creators and creator-led businesses where the bet that we're making there is that the internet is getting more and more siloed. We're like, I have my internet, you have your internet, like algorithms and interest drive everything.

• 40:22Speaker 03

  People that are kind of like cult leaders in different pockets have interesting opportunities to build businesses around like their niche or their audience where if you're kind of seen as the like, like market or industry leader on your thing and you have hundreds of thousands or millions of followers, like can you build businesses on top of that platform? We think so. 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 where they're pocketing six to low seven figures a year. And I think we're hitting a point now where like pretty niche creators,

• 41:05Speaker 03

  again, most creators aren't that entrepreneurial, but the ones that are that really get distribution, they basically, 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 wouldn't necessarily say build a media business, but leverage podcasts, YouTube, Twitter, LinkedIn, whatever, to just drive a lot of revenue.

• 41:31Scott Galloway?

  I'm curious, what role does AI play in your written work? How do you use AI?

• 41:38Speaker 03

  So the, 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 to 30th of the link. It's like 300 times more difficult. It was mine.

• 42:03Scott Galloway?

  Yeah. Well, my advice would be just keep at it. So you can find out it gets worse.

• 42:06Speaker 03

  Yep. Yep. Yep. I can't, I can't.

• 42:08Scott Galloway?

  It doesn't get better.

• 42:09Speaker 03

  Um, but on the, on the AI stuff, I actually tried to do the like, okay, could I voice to text a 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 were whatever, written by ghostwriters. I'm sure there's some Claude in that. I actually, I was like, can it even like mimic my voice? It couldn't. I fed it like all my blog posts to like, see what it could do. Um, but the thing that AI was very useful for, is very useful for is like minimizing the feedback loop of like getting

• 42:53Speaker 03

  some version of feedback on your thing. So like, when I was working through like draft chapters and I 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 if like 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 it, 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

• 43:37Speaker 03

  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, 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. Uh, and on my blog posts and stuff, it's obviously a game changer for research. Like perplexity is very useful for pulling stuff quickly. Having Claude code synced up to my computer, I can like pull from different files where I have like different information on companies that I want to like query quickly. The information retrieval and review are just set up a lot. It's kind of the biggest thing.

• 44:14Scott Galloway?

  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.

• 44:32Speaker 03

  Yeah. You summed up my like three minute monologue in about one sentence. Yeah, I agree with that.

• 44:38Scott Galloway?

  And what's next for you, Jack?

• 44:39Speaker 03

  I mean, hopefully sell like a million copies of a book. I don't know. Um, no, I mean, like right, right after this, we have our like partner meeting and the fund I'm at to talk about startups we might want to invest in. But like in, in general in life, it's like, I, 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. I don't have the next one now. Um, 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 with these founders

• 45:23Speaker 03

  all day, look at different deals. Um, I try not to, I try not to think like too, too far ahead. I'm 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 in 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 like 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.

• 46:08Scott Galloway?

  Jack Rains 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. Uh, 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 [email protected]. Again, that's [email protected]. And one last thing, if you'd like to join future live streams, subscribe to Prop G Plus at profgmedia.com. And if you're not already reading Jack's work, check out his Substack and preorder his new book, which we'll link in the show notes. Jack, thanks for joining us.

• 46:43Speaker 03

  Scott, thanks for having me.

• 47:05Scott Galloway?

  Algebra of Happiness, No Mercy, No 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 2.8x 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 catharsis for me just to talk about whatever I wanted. And also I enjoy writing and I'm

• 47:50Scott Galloway?

  fundamentally a lazy person. So I, 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's can be on anything from engagement levels on Snap to the valuation of WeWork to putting my dog down, which was the most read post of, 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

• 48:34Scott Galloway?

  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 and 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, and, 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

• 49:18Scott Galloway?

  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 the Alzheimer's away, if you will. And I find that focusing on or trying to restructure that last sentence keeps me sort of, it's 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

• 50:01Scott Galloway?

  sons will read my posts from, 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 it's, 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

• 50:46Scott Galloway?

  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, it starts with the 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 I would have is the following, start writing.

• 51:27Scott Galloway?

  This episode was produced by Jennifer Sanchez and Laura Janer. Kami Reek is our social producer. Bianca Rosario Ramirez is our video editor. And Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.