How Much Money Is Enough? Plus, Why AI Won’t Replace Financial Advisors — with Jack Raines

Scott Galloway is joined by Jack Raines, writer of the Young Money newsletter and author of Young Money: A Field Guide to Wealth and Purpose in Your Twenties. Scott and Jack discuss what "enough" actually means, why the rent-versus-buy math rarely favors buying in the highest-cost cities, and what a financial advisor is really for once AI can place the trades. Want to be featured in a future episode? Send a voice recording to [email protected], or drop your question in the r/ScottGalloway subreddit. Plus, you can now call or text Scott a question at our new Office Hours hotline: ‪(201) 472-3656‬. 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.

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• 1:21Scott Galloway?

  Welcome to Prop G on Personal Finance, a special episode where we're joined by Jack Rains, writer of the Young Money Newsletter and author of Young Money, A Field Guide to Wealth and Purpose in Your 20s. Together, we'll discuss whether there's such a thing as enough wealth, how young people should save for a house in a high cost city, and whether wealth advisors survive AI. Jack, welcome.

• 1:42Speaker 06

  Happy to be here. Thanks for having me, Scott.

• 1:44Scott Galloway?

  Thanks for being here. Everyone was really excited to have a young, knowledgeable financial person on. All right, let's bust right into it. Question one, our first question comes from Natanya Cranford on Instagram. Is there such a thing as enough wealth? I still fly economy, but I can fly anywhere I want. Jack, is there such a thing as enough wealth?

• 2:04Speaker 06

  So I mean, I think the answer is yes, there is. The issue is humans are kind of status chasing monkeys where like, once you get to what you thought was enough, there's always another level. So like, it's a question of like, I'm from South Georgia, right? So my version of enough wealth, growing up, is a lot different than having lived in New York or San Francisco for the last four years. So I mean, my answer to that is like, yes, there is. The question is like, can you resist the like chasing people who are one level ahead of you? Because is there an upper limit to wealth? No. Is there enough wealth? Yes, depending on like where you set your standards for what enough means. You know, for some people, it's like several hundred thousand, a few million, tens of millions.

• 2:48Speaker 06

  But it's much more, can you resist just like chasing after other people that you view to be a little bit ahead of you?

• 2:55Scott Galloway?

  Yeah, I think about this a lot. I mean, on a very practical level, if you take your annual burn times 20, that's when you sort of financially are probably set, right? And can start to enjoy life. And also, I think a lot of people make a mistake. I had some questions from some people who are retired about how much money. And I'm asked about their life. I'm like, you should be spending more money. You know, you're not, unless you really do something stupid, you're fine. And you got, my sense is you guys don't travel, you know, spend some money. Order the good wine. And I think about this a lot. I think hoarding wealth is a virus that infects America. I just don't think there's any reason to have over a certain amount of wealth.

• 3:39Scott Galloway?

  I don't think you're going to get much happiness, if any incremental happiness. I don't think you'd be less happy. I think this notion that billionaires are less happy than millionaires is also a myth. But what you said, what is it? Humans are memetic and that is, we don't think about satisfaction from what we have. We compare ourselves to others. And I have more money than most citizens, but I would like, and I stopped aggregating wealth or purposely trying to aggregate wealth after about 10 years ago. I either spend it or I give it away now. But I still occasionally regret not getting, going more in on AI and trying to become a billionaire because I would like to fund NPR. I would like to have more political influence and candidates. You can always find reasons.

• 4:23Scott Galloway?

  I still feel insecure and I would love to have, you live in a capitalist society, no matter how wealthy you are, they're always going to create incentives to want more to keep you working, right? And keep you productive. But I do think there's an art to saying, at some point, I at a minimum want to focus on my relationships and get off this hamster wheel. And it's not easy. And by the way, that's a, that's a story of privilege because I think the vast majority of people are just trying to figure out a way to save enough to send their kids to college and not have medical debt. But yeah, that word enough is so powerful and it's consciously deciding yourself, when is enough and what would happen if I were fortunate enough to get to enough? Any closing thoughts on this?

• 5:07Speaker 06

  Yeah, I mean, there's, I have two things to add. One, do you know Nick Maggiulli? Anyway, he had in a blog post like four or five years ago, had a really interesting stat talking about how like, you know, most people are worried about not having enough money in retirement, but most Americans actually are spending less than like, they're earning more each year than what they're actually spending down in retirement. So to your point of like hoarding wealth being a virus, I think it's actually an inefficient use of money. If you have like several millions saved up and there's just no chance, like even accounting for what you want to leave for your kids or grandkids. If you're rapidly accumulating more and more money just from compounding in your 70s and 80s that you can't spend down, you probably should have spent some sooner. And the other, the other point I have on that is like,

• 5:51Speaker 06

  the whole point of wealth at the end of the day is somebody has to spend it on something, whether it's you, your kids, you give it away to like a philanthropic organization to spend. And having like a scarcity mindset where you're constantly worried about not having enough, even when you objectively have enough, is just depriving yourself of things you could spend money on to enjoy. Again, whether it's material things, experiences, relationships, and like the things that you can spend that money on that you will enjoy are just going to change a lot. The thing you'll enjoy at 25 is different from 35 or 45 or whatever. So I actually think one of the hardest things is like being willing to spend some money in your 20s when you probably don't have as much, knowing that like you'll keep compounding over time, right?

• 6:36Speaker 06

  But it's tough. It's like, it's a very tough thing to spend money when everybody else is still making money and thinking through like, our idea of what we're going to need later is always so much higher than what it actually is. I think.

• 6:49Scott Galloway?

  Fair enough. All right, let's, let's head on to question number two. It also comes from Instagram. J.Kim asks, how should young people go about saving for a house in a high cost of living city? Jack?

• 7:00Speaker 06

  So I think the first question is, do you even want to? Because there's a lot of people who will move to New York or especially San Francisco now with the AI boom, where I lived in SF last year and the going rate for like a decent studio apartment is around probably $4,000 now. That's for a, you know, 500 square foot shoebox. So the question is, okay, you can make the math work on that, but then you get married and you want to have kids. And all of a sudden, you probably need at least a three bedroom home, which is going to cost like, if you're actually in San Francisco proper, probably $3 million. I was looking at some three bed, two baths in New York. It's like prep for the same thing, call it $3 million minimum in a decent neighborhood. And then if you're doing that, okay, are you going to pay for private school?

• 7:44Speaker 06

  And what's that going to cost? Are you going to have a car? What's the parking going to cost? Like you, you end up in this thing where you're going to be spending so much money per year to keep up. Like the first question to ask is, should you even buy a home in like New York or San Francisco? Or should you live there to make money, meet your spouse, like save cash and rent? And then once you're at the point that you're having kids or thinking about school, you move to the suburbs or you move to New Jersey or Long Island or pick your version of that.

• 8:11Scott Galloway?

  Yeah, look, I think you're right. I think it's important to do the math that this, you never lose money in real estate. The American dream is brought to you by the National Association of Realtors, who always find a reason for you to keep just buying and give them their 5% or 6% commission. There are a lot of instances where it doesn't make any sense to, unless you just have a lot of money to buy versus rent. New York and San Francisco, almost always it makes more sense to rent. And there is a certain, you know, elegance to renting and slamming your keys down and being economically mobile because what you don't want is end up underwater on your mortgage or to be house poor and just so focused on making your mortgage that you can't enjoy life.

• 8:53Scott Galloway?

  The, I do think at some point, I mean, I'm torn on this because while as an asset class, homes have done the same or even maybe slightly underperformed the broader market, it is a great way to build wealth because people have a tendency to make that mortgage payment as opposed to maybe spending $2,000 or $3,000 saving and buying stocks. They have a tendency to make that payment. Also, I think there are some real psychic benefits, specifically moving towards a family or mating or having kids and procreating, which I think are rewarding. And that is, I was fascinated by the study that said that housing prices are a form of birth control and that is for every 10% housing prices go up, the birth rate has declined by 1%.

• 9:35Scott Galloway?

  Because, I mean, you're, you're a kid, Jack, but generally what you find is when you buy a house, you start fixing it up and you start fixing up a second bedroom and decide, well, maybe we should find someone to live in the second bedroom. I know, let's, let's, let's pull the goalie and have a kid, right?

• 9:49Speaker 06

  Create one, yeah.

• 9:50Scott Galloway?

  Yeah. So, and I think generally speaking, that's good for you, good for your wealth, good for your marriage. Well, I don't want to tell people. Let me be clear, you can't save a marriage having kids. That's probably not the thing to do. But I do think there is. Psychological return, psychic return in homeownership and that I think a decent policy, I met with a Democratic Senator this morning, a lot of people think is running for president. I mean, instead of drill, baby, drill, it should be build, baby, build. And we should have tax incentives and unleash the private home builder sector and, and YMB laws such that we go back to where I was. I was living in San Francisco out of business

• 10:30Scott Galloway?

  school. I bought a two bedroom house in Pachero Hill for $285,000. The average graduate of the Haas School of Business in 1992 was making a hundred grand. So it was 2.8 times my salary. Now the average Haas grad is making 200 grand, which is a great income. But the average home, I think in the Bay area as of last year was 2.2 million. It's probably closer to three now because you've seen this acceleration. So what is that 15? It's gone from 2.8 to, to, to 15 times. And like so many things in our society, housing has been a transfer of wealth from the entrance to the incumbents where they create artificial

• 11:10Scott Galloway?

  scarcity through sequestering housing permits, by putting housing permits or the authority in the house of current homeowners. This is an instance where it should go back to bureaucrats. You need growth. You need more housing. And people like you are having a tough time finding a house because people like me get very concerned with traffic and make it more difficult to build more housing such that the price of my house goes up in value. I think this is a big issue for America. You need a kitchen cabinet of people who can sit down with you and say, all right, give me the math, give me the numbers. Should you buy a house? Should you not? And even if it doesn't make economic sense, if you got rich parents and you got, you know, a dude you want to marry, buy a house. You know, it's just, there's a lot

• 11:53Scott Galloway?

  of nuance here. And I think people, this is one of those things where people will spend so much time deciding which iPhone they're going to buy. And they don't spend enough time for 1,500 bucks. They don't spend enough time thinking about what is arguably the largest purchase of their, of their life. I also think, and I'm sorry for the word salad here, that the IRL movement where Live Nation is booming and Taylor Swift tickets are going for, you know, $6,000 is that a lot of people of your generation have just given up on saving for a home. Tip, when I was your age, every dollar I had was going towards a little fund where I could save $60,000 for the down payment on a home. And now I think a lot of kids or young people are saying, there's no fucking way I can buy a home. I'm just, I'm going to go to Coachella.

• 12:37Speaker 06

  I mean, well, something else that's funny that you hinted on there was, and I totally agree on the like YMB versus NIMBYism. At the end of the day, we should build more homes and then people could like afford to move into a home. But a lot of the voters don't want their home prices to drop because of what we were saying earlier about it's a lot of people treat it like an investment asset. You don't want your $4 million home to be worth 2.5 million, even if a lot of 26 year olds can then buy homes. But this is especially true in New York. So much of the housing is like subsidized by people who do have rich parents. Like, you know, like, I didn't really pick up on this until like, I also went to business school. I was at Columbia and like you have people who are taking out a couple hundred thousand dollars in student loans. You have people who are

• 13:18Speaker 06

  like fine, but not like trust fund kid. And then you have people whose lifestyle subsidized or like parents will like buy them an apartment or townhouse. And everybody's competing for the same housing supply. So like for the, I guess for the people who are like making their own down payment for a home right now in a high cost of living city, so much of the already scarce supply is also subsidized by like family income, which I'm like all for. Like if your parents can like support and help with like big life costs, awesome. But it makes that really tight supply even tighter. So it's just tough. You have like a really tough supply demand market. You have a lot of factors against you. And yeah, there's a little bit of financial nihilism where people are like, I'll never afford

• 13:59Speaker 06

  a home, at least not in one of these two cities. So why not blow it on, you know, material goods, consumerism experiences. And it's just a pretty vicious cycle.

• 14:09Scott Galloway?

  Okay. So we'll be right back after a quick break.

• 14:21Scott Galloway?

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• 16:44Scott 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 Agentic 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

• 17:27Scott Galloway?

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• 17:54Scott Galloway?

  Welcome back. We're here with Jack Rins. Question number three comes from Cordova, Texas. Will there be a need for wealth advisors as AI tools develop over time?

• 18:03Speaker 06

  Oh yeah, 100%, I mean, like you don't, you don't get a wealth advisor to like help you outperform the market. There's a million like agentic AI things. Robinhood just rolled out some AI agent trading tool, like to actually place trades. Yeah, AI can do it. But wealth advisors are really there to like tell you what not to do and to fix behavioral problems.

• 18:23Scott Galloway?

  Great point.

• 18:23Speaker 06

  Market tanks, you panic, you want to sell. Like the amount of people who would have sold the bottom in 2020 when the market tanked or would have sold in 2022, Q4, when like the Nasdaq was cratering, where if they had a financial advisor who was like, stay the course, if anything, like increase your contributions now while stocks are on sale. Um, you know, for somebody who would have like impulse sold because they panicked, they would have missed out on the market doubling from those bottoms. So I actually think there's more and more and more noise that's causing people to feel more and more distracted when it comes to investing. And having a professional that can actually just manage your emotions and stop you from making like behavioral screw ups is more important now than it was at any other point because of like so much noise on social media.

• 19:08Scott Galloway?

  Yeah, it's.

• 19:11Scott Galloway?

  It's interesting about three quarters of Gen Z and two thirds of millennials seek financial advice online or via social media. And only one in seven Gen Z say they would turn to a financial professional first when faced with a question about finances compared to 39% of boomers. What's interesting is that, well, let me go to your point. I have found I didn't use a financial advisor, maybe I should have, but I didn't to get wealthy. I use them now to stay wealthy.

• 19:34Speaker 06

  Yep.

• 19:35Scott Galloway?

  And that is, I'm not really interested in their stock recommendations. I just don't think they know any more, any less than me about stocks. And also, to be fair, I think some of these guys are pushing their internal funds, which tend to have higher fees. And I think fees are the enemy of compounding returns. I think you want to be on low cost index months, you want to be diversified. I spend a lot of money on financial advisors, but mostly it's about diversification, tax efficiency, which is Latin for legal tax avoidance, and then things like trusts and trying to figure out a way like that I give my kids enough money someday such that they can do anything, but not enough money such that they can do nothing.

• 20:15Scott Galloway?

  You know, if you're blessed with some level of economic security, you want advice on how to be smart, how not to lose it, to find out if you're too concentrated. Should I be, oh, I should sell, I need money. Should I sell these stocks? A financial advisor might say, no, don't sell the stock, borrow against it and let it continue to compound because we can borrow against your stocks, you know, 10, 20% of their worth and not be that worried about getting too over levered. And you don't have to pay taxes on your gains. I mean, there's just, it makes sense. Once you have a certain amount, use AI, but use it to inform you and then talk to people who understand money, whether it's a financial advisor or just other rich people who really

• 20:58Scott Galloway?

  understand how to invest money. What's interesting is that while AI, I'm an AI optimist and think it's going to create more jobs than it destroys. And I think you're going to have more financial advisors in 10 years than you have now. And there's going to be a shortage. Nearly 40% of financial advisors are expected to retire within a decade, creating a shortfall of roughly 100,000 professionals. And AI tools may not, you know, may be structurally required to step in and fill the gap for retail guidance, but these LLMs have, you know, they have real biases and they're generally not good at giving long-term financial advice. And the quality of what AI tells you is based on the quality of the prompt, which is based on your financial literacy.

• 21:41Scott Galloway?

  Younger people who are not as financially literate are asking AI like, how can I get 10x my money in the next 12 months? And it'll come back, it'll say, look, that's unlikely, but the most volatile assets are crypto and try this. So a lot of it's prompt. And also, there's a study showing that these LLMs appear to be sexist and that their recommendations tend to be more conservative towards women than men, resulting in them not making over the long term as much, much money. In sum, I think it'll be an enhancement. It'll make financial advice more accessible, which is great and it's a good thing about AI. But it won't replace human advisors since the quality of guidance depends on who you

• 22:23Scott Galloway?

  are and context and nuance and tax. I think we're actually going to see more financial advisors and I would say that it's probably with the right credentialing, understanding accounting, very much you need to understand tax. If you have good relationship skills, if you're good at networking, if people know. Being a financial advisor is the worst job in the world for 10 years because it means to go in every fucking event and kissing everyone's ass and sitting them down and talking to them about their financial future and being their therapist when the market goes down. And then after 10 years, if you can survive it that long and build a book, it becomes the best business in the world because you basically have an asset base of people who keep paying you, you know, 10, 20, 50, 100 basis points on the assets under management.

• 23:07Speaker 06

  Their portfolios keep going that way.

• 23:08Scott Galloway?

  Hopefully, right?

• 23:10Speaker 06

  Yeah.

• 23:10Scott Galloway?

  Hopefully. But any closing thoughts on the career prospects of someone thinking of, thinking of being a financial advisor?

• 23:19Speaker 06

  Yeah, I mean, I think it's, I think it's one of those things where at the end of the day, it's always going to be a relationship game. And something that a lot of the Silicon Valley world misses is you can't just replace human relationships with technology. You can like amplify a lot of stuff, but when people are in like markets are volatile, people are emotional, they both like, they won't like a comforting voice to rely on on stuff or somebody walking back from the cliff. So, you know, I, my real advice is it isn't about like, should you go into this job or that job or whatever, but just don't like, I would not be pessimistic about AI's impact on relationship driven industries, you know, financial advice being one of those.

• 23:56Scott Galloway?

  Yeah. So again, everything, everything still comes back to the core skill, which seems to be the most enduring and that is the ability to establish, establish relationships. Jack Rains is the writer of the newsletter Young Money and author of the forthcoming book, Young Money, A Field Guide to Wealth and Purpose in Your 20s. He's holding it up. Jack, thanks so much for joining us and congratulations on your success.

• 24:18Speaker 06

  Thank you. Thanks for having me.

• 24:21Scott Galloway?

  This episode was produced by Jennifer Sanchez and Laura Janer. Kami Rieck is our social producer. Brad Williams is our editor and Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.