I think passion is stupid because, one, if you're passionate about a thing, it probably won't pay you well. Even if you find a job and you're passionate 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. Figuring out how to leverage those skills or interest in something the market actually cares about is very important. 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 when you have like 100 million bucks.
Good afternoon and welcome to our Prof Plus livestream. 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 at PropG Markets and on PropG is that for young people, the work-life balance is a myth and that there's only trade-offs. 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 expended 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, 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 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. Tell us why you recommend that path versus the one I took and how you came to that 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 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 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 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 than they will 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 spent 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. That 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 that 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 in a very finite defined window when it made sense to do it knowing there was an end date. So I went for it.
Yeah. It sounds like we're more in line than probably we thought. 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?
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 $1,200, $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 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 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. But like hopefully by the time you're, you know, 28, 29, you can get it to $200,000 plus and you can like more than compensate for the lack of money you were making early. So, I do think focusing on like skill accumulation, building a network, putting yourself in any 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.
You've also laid out fairly concrete money mechanics: spending a bigger share of small income 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 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 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 on the trip was worth way more than investing another $3,000 or whatever. And then maybe it's worth what, $4,500 now with 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 in life stage. Like you hit a point where there's only 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 another 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 of their environment they grew up in or kind of came of age in. But 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 offer from 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 turn 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 in 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. Like, can I leverage the thing I built with my platform to like apply it to 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 and you're passionate 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 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 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 when you have like 100 million bucks. 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, optionality is interesting and like I'm 29 now so like late 20s 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. Yeah, I mean, 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 optionality path runs out and you sort of end up, inertia 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 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, maybe self-selection, were very ambitious and wanted to go into something that they thought they would enjoy. No, that's not wrong. That's all right. The majority of 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. 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 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 strategy, it can be actually kind of intellectually rewarding. It's like it's 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 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 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 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 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. So, I would argue, and again, it's not romantic, that the majority of the regret is from people who got a late start because they didn't realize that they mistook their passions for their hobbies and for a career. If you listen to TikTok, it's all you need to do is find your passion and just never give up. No, there's a time to give up. There's a time to move on. And I think I probably stuck with some stuff too long. I stuck with RedEnvelope 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 of my life professionally haven't been the biggest failure. 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 3 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 recognized 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?
So, that's kind of like, the original thing that put us on this thread was 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 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 probably more valuable in the dating market in your late 20s than 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 my take on optionality in general is that it's actually very useful in your 20s. Again, if you find the thing that you're good at and you enjoy, whether that's like a job or a person that 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 in 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 a generalist, than I would 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 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.
Support for the show comes from MongoDB. AI-assisted and agentic coding can help you build faster than ever. But if your data layer is a bottleneck, what's the point? MongoDB actually gets out of your way. MongoDB is a unified AI-ready data platform that empowers you to build scalable generative AI applications. It eliminates the need for separate specialized vector databases by combining a flexible document model natively with semantic vector search, full-text search, and real-time
Operational data. Instead of wrestling with rigid schemas or translating data formats, MongoDB's native data model mirrors the language LLMs already speak. Plus, MongoDB gives you the flexibility to ship at the speed of AI. The ACID compliance lets you sleep soundly at night and scales to handle massive Fortune 500 workloads. Developers have a word for that kind of reliability. Actually, four words. It's a great database. Start building at mongodb.com/ai.
Support for the show comes from SoFi. One of the biggest advantages wealthy people have is the means to hire people who can help them make better financial decisions. But for most of us, there's six different financial apps that don't talk to each other. That's where SoFi Coach can help. Coach provides step-by-step chat-based guidance for all your finances, helping you pay down debt, save more, spend smarter, and invest. It doesn't just give you advice. It can actually execute the moves for you with your approval. You can also ask important questions such as, "Can I afford to buy a home this year?" or "How can I improve my credit score?" And because it's connected to your linked accounts, the answers are tailored to your specific financial situation. And if you ask SoFi Coach, "What should I do with $10,000?" If you're lucky, you might need the answer sooner than you think, you'll be entered for a chance to win 10 grand. Learn more and enter at sofi.com/propgcoach. That's sofi.com/propgcoach. This is a paid advertisement by SoFi Technologies and is not intended to be financial advice. No purchase necessary. A purchase will not increase your chances of winning. Open only to legal residents of the 50 US/DC, 18 plus, void where 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 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?
So 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. If you join like, I don't know, say you joined Cognition on their like, they're one of the hottest like AI coding companies right now, right? If you join as an account exec there a couple 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 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. So there's like a real arbitrage in 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 like joined Ramp really early. He was at Goldman for a couple years. He was just like basically an SDR at Ramp and nobody really heard of Ramp. They were like Series A at that point. And guess what? Ramp's valuation has like, I don't know, 50x'd since then. He's now like a very high up VP or exec there. It was sales. Like even before, 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, 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 like move up or you're dealing with like higher and higher net worth clients, there's just so much money to be made. 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 to like tell a girl at a bar, there's probably companies where you can join and do that and make a lot of money.
Versus I would argue that like private equity, which is still the hot finance thing, so much of the compensation is backloaded in carry, and like private equity as an industry you could argue is 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.
