In this podcast, Motley Fool co-founder David Gardner talks about a listener who says he invests $100 for each of his daughters’ birthdays, positioning them for success in their financial futures, and another listener who follows David’s advice to add up; don’t double down. David also shares some memories and reminds us that the math is always against you when it comes to sports betting. Plus, listener and host swap stories on selling Netflix (years ago) to build and buy their homes.

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A full transcript is below.

This podcast was recorded on Sept. 24, 2025.

David Gardner: One hundred and nineteen. That’s the magic number this week, 119. Because this is the 119th consecutive Rule Breaker Investing monthly mailbag. That’s nearly ten years of unbroken exchange, the final Wednesday of every month between you, my dear listener, and me the fool who gets to sit on the other end of the exchange marveling at your stories, your questions, your challenges, your inspirations, the sharing that comes my way from around the world for nine years and 11 months as of today, thank you, and thank you is going to be a recurring theme for this particular mailbag, only on this week’s Rule Breaker Investing.

Well, it’s not every week or month a new book comes out by me. Understandably, a lot of this week’s mailbag is going to be focused there. I also am guessing we might have some new listeners, an unusually high number of new listeners this week. I should explain that sound that some people love and some people don’t like at the start of my podcast. The one with the window breaking. Well, that’s not really a window breaking, that’s the sound of rules being broken. That was put in place by my original producer, Rick Engdahl. Yeah, July 2015, and we’ve been publishing a fresh new weekly podcast every week since going for the Cal Ripken streak here, never taking a week off. Yeah, that’s the sound of rules being broken. If you become a regular listener, I hope you’ll come to love it. Well, yeah, Rule Breaker Investing. The book came out just last week. It’s been a lot of fun doing media, some of it in New York City, a lot of it just sitting at my desk at home, being on people’s podcasts. We’ll talk about that a little bit this week. I’ve had a lot of fun reading reviews and if you do read the book and love it, I would even say if you hate it, I would love for you to leave a review anywhere where reviews are read. Amazon is where most people leave reviews, but I’ve read some really lovely reviews on Audible for those enjoying the audio book. But reviews help people discover books and with this, my final stock market book, I’m hoping as much of the world will discover it as possible, which means more and more people will be playing the only game that counts the long game with a strong long game. That’s my hope for my fellow humans and that’s the promise of Rule Breaker investing the book.

Thank you again for those who have already left reviews and I would love it, especially if you love it, if you’d think to leave a review somewhere online about Rule Breaker investing. This is also a fun day for me because Readwise, which is an app I’m going to explain a little bit more about in a minute, something I first started talking about a few years ago, just like Duolingo, the language learning gamified app, Readwise lives in streaks. Readwise, let me explain it now and then say why today is special. Readwise is an app, especially for those who love eBooks. I think two in 10 purchasers of books these days, nonfiction any by the eBook. Still the vast majority preferring hardback or paperback books. But for those like me who love their eBooks, as we highlight as lines jump out to us off the electronic page and you highlight it in pink or yellow or whichever color you choose, Readwise saves that. If you’re using the Readwise app, it uploads all of your highlights across all of your eBooks into the Cloud.

Then it brings those back to you ever after. You can get it as a morning newsletter, five of your favorite past quotes randomized and you can add more information or more thoughts to them. You can connect them together with other quotes from other books. It is an amazing resource, the Readwise app, and it really helped me write Rule Breaker Investing because it enabled me to save a lot of my favorite lines from books I’ve read and then bring them back into my book Rule Breaker Investing. I had a friend say, hey, David, really enjoy that. You must have used AI to source a lot of your quotes. I said back, no I didn’t use AI to source any of those quotes. It was all Readwise. I guess in a sense, Readwise, you could claim is AI, but the ability to hold and save forever the things that jump out to you in a book is such a powerful thing and my fun day to day is that I’ve now been using Readwise 999 days in a row here on Tuesday, September 23rd, 2025. When I first started talking about this app a few years ago on this podcast, you should know, I’ve stuck to my knitting. I’m eating my own dog food. I really love Readwise, clearly, because I’ve used it 999 days in a row. Shout out to Tom, Francis, Khalid, Arcia, Simon, and Mick because they are the seven other people who are tied with me at the 999 day mark because on Readwise, Lightly gamified, you can see who else has long streaks and Tom, Francis, Khalid, Arcia, Simon, and Mick. I don’t think any of you is listening to me right now, but you should know, I’m right there with you. I’m in quotes David with a little fool Imogi next to me on the Readwise standings. As this podcast comes out Wednesday, September 24th, will be my Readwise 1,000th day. But who’s counting? Before we get into our, I would say shortish mailbag this week, I want to mention there’s a bonus chapter that I’m writing for Rule Breaker Investing. If you’ve been to Rule Breaker Investing.com, you’ll see that it’s a free downloadable bonus chapter. It’s not pinned up there yet. It will by early October. But just to give you my dear listener a little inside window into what we’re doing with that, I’m basically going to make that chapter a mailbag. I’m going to take in some of the best most thoughtful questions and comments that I’ve gotten about the book and the bonus downloadable chapter will be my answers back, basically an FAQ to the book itself.

That’s where the bonus chapter is headed. I’ve already written much but I would appreciate your questions, especially next month on next month’s mailbag, [email protected] is our email address, and I would love some questions or thoughts back based on your reading of the book, because I’ll probably pull a few of the best ones and add those into the bonus chapter as well. In fact, just like software releases updated editions, I’ll probably add a little bit more into that bonus chapter over the course of the coming months version 1.1, 1.2, 1.3. Again, great questions, thoughtful challenges, anything that you enhance the experience. If you felt like the books missing something and you’d like something more, I’d love to hear from you [email protected]. We’ll talk about it on next month’s mailbag, but it might well end up in the Bonus Chapter itself. I see five mailbag items today, but first hot takes from Twitter. First one, at Sam Horn Intrigue. My author in August Sam horn Tweeting out. I am still hearing from people, Sam writes, who enjoyed that rock ‘n roll conversation as much as we did at David G Fool. Thank you for your perfect questions and for setting up that rising tide lightning round of what to say when. That was a lot of fun. Thank you, Sam horn. It was a delight to introduce you to my audience. Gotten so much good feedback. So many people have enjoyed reading your book already. Let’s do it again sometime, Sam. Thank you. matthard@307fool. Thank you, Matt. You said, love the 10 year look back. Lots will change for the companies you own, but the most important lessons are still true. Winners win, and they carry the build of your outperformance as long as you can hold on, and Matt writes hold with about 10 letter Os.

As long as you can hold on. Yeah, thank you, Matt. I’m really glad you enjoyed the 10 year look back. Again new listeners, years ago, I picked every 10 weeks on this podcast, I picked what I called five stock samplers. I’d pick five stocks to a theme. The aim was to beat the market with that sampler, and we’re now hitting the 9 year mark for the very first one. The first of those, well, that was this month’s first podcast. September 3rd, 10 years later, five stocks for the next five years. That was the first five stock sampler I ever picked. It was called Five Stocks for the next five years, and we’re reviewing those 10 years later. It does remind me that usually I go back over what we did this month. I’ll just mention, that was the first podcast this month. Then we had a Rule Breaker investing highlight reel putting together all my page Breaker previews on September 10th. We had an audio book sneak peek for anybody who might be interested in the audio book. That was an eight minute extra podcast, one of my shortest podcasts ever done just 10 days ago or so. Then of course, last week’s Market Cap Game Show Planes Stakes and automobiles with Andy Cross and Yasser El Shimi. That is the month that has been for this podcast. Matt Hard, thank you for writing in with your appreciation of the 10 year look. Every 10 weeks going forward, we’re going to go back 10 years and we’re going to learn together how those five stocks have done, why they did what they did, and let’s hope we’re beating the market. Pretty sure we will be, but not with every one of them. Well, there was one other theme to Twitter X hot Takes this month, and that was, yeah Book. I’m just going to read several off because it’s a motley array. When I said, there’s a lot of thank you this particular podcast, that’s what I want to do again. I want to thank each of you for taking the time to tweet out what you did. Happy to share some of my favorites here at the start of this month’s mailbag. Jean Marc Aas Jean Marc, you wrote, I’m going to wait to see if the reviews are good on David G Fool’s new Rule Breaker Investing book before I buy it. Said nobody ever can’t wait to crack open my new copy.

Thank you, Jean Marc. Nick Sipel at Investing Nick. In an era of fake gurus, David G is the real deal with real results delivered publicly over decades. More admirable than David’s returns though, is his work to teach investors how they can invest better. I’ll be reading David’s book next week. You should too. Thank you very much at Investing Nick. Always a pleasure, Nick. A thanks to you for helping the world invest better for making all of us smarter, happier, and richer. Thank you, Nick. At anendkatri. Anand, you kindly wrote. It feels like the best player of the game won the championship and announced the retirement and put everything in the last Masters stroke in this book. Thank you at David G Fool and at RBI Podcast, receive my copy and can’t wait to start. That’s very kind. Thank you, Anand. This is obviously somewhat embarrassing for me to read. Not every mailbag sounds like this. Otherwise, they could be cloying, but this is a special week. Carrie Huntley @chuntley1234, really appreciated. This one, Care at David G Fool. Since my Amazon pre order is on Ba Order, I decided to take a trip to a couple of Barnes and Noble locations. I was able to score a copy for myself. That preorder will be a Christmas gift for my niece and nephew. I can’t wait to get started, I especially appreciate Carrie that you took the time to take a photo, Carrie of you holding the book up in the Barnes and Noble. I see the intelligent investor hiding on a shelf just behind it. Anyway, a lot of fun to see that picture. Thanks for taking the time. I’m glad you had a Barnes and Noble near you and you could pick the book up there. I’ve been a little frustrated to see that the book sold out on Amazon the very first morning it came out.

There are more copies coming though. Everybody should know that and I guess it’s a good problem to have if you’re going to have a problem. I also want to mention how much I’m enjoying seeing the book in different places. Gilbert, another Twitter friend of mine, took a picture of Rule Breaker Investing sitting there on his chessboard. It was very artistic. I thought it made a good visual point. I just want to let all my readers know if you want to take a picture of the book in some fun, crazy place or making a fun visual point really plays well with me on social media. It is a treat to retweet those out and see that trusty little green side kick, that book appear at all kinds of different places. I’d love to see it on a ski lift here as we hit winter in the northern hemisphere. Just a couple more @emmett L Savage. Emmett Savage, David G Fool has been the most inspiring investor in my life and his new book will inspire the next generation of investors. Thank you very much, Emmett. I truly hope that is the case. That’s why I wrote it, and those words coming from you mean a lot. Finally, @raulseti, Raul, you said, My Rule Breaker investing pre order came in the mail yesterday, and I read it, cover to cover within a couple of hours. Beautiful and timeless investing wisdom in an easy to digest way, distilled differently than anyone else can. My biggest surprise was reading that David does sell underperforming businesses or for opportunity cost reasons. All this time, Raul concludes I thought he had never sold anything ever. I’m glad that you were disabused of that notion, Raul. Certainly, I’ve sold in the past. Most of the selling I’ve done, I’ve ended up regretting and I’ve certainly made that point. I once wrote a column for Motley Fool Stock Advisor members pointing out that if we at Motley Fool Stock Advisor had never once sold any of the picks that we’d made and just held every single one of them, every bad pick and every good pick right through two today, we would be ahead of where we are today and I’m still quite happy with where we are today.

There can be lots of reasons for selling. Sometimes I sell to harvest tax losses to net out a capital gain at the end of year. Sometimes I have to sell because one of my big winners just gets too big for my portfolio. It exceeds my sleep portfolio principle Number 4, and that’s the best reason of all to sell. When a stock like Amazon or Netflix blows up in your portfolio so much that you’re going to need to sell or maybe just give those shares away, which by the way, the best charitable way to give is shares of appreciated stock. I’ve done that. I bet many of you have done that too. It’s a neat trick if you can pull it. That wraps up my Twitter X Hot Takes. Let’s get in to the Mailbag now five items. Here comes Mailbag item Number 1. Thank you, Kevin McMahon. Hello, David. I recently listened to your audio book and thought it was excellent. Baseball played such a big role throughout your story. That really resonated with me since my dad and I have always shared a love for Strat-O-Matic baseball. The games and the statistics behind them have been a lifelong passion of ours. I was so excited about the book that I even became one of the first people to leave a review of it on audible. That being said, I’d like to pivot to your recent appearance on Chris Hill’s podcast Money Unplugged. As a longtime listener of Rule Breaker Investing, I was surprised by how much more I learned about you through that conversation. Highlights for me included your first memory of money, your family background, your early computer experience, your schooling, both high school and college, your journey toward a career, and of course, Kevin goes on more baseball. I especially want to call out your time in Rochester, New York. I grew up in the Finger Lakes region, Penn Yan near Rochester, so that really resonated with me. I would highly recommend not only your episode, but also the other conversations on money Unplugged. Chris Hill’s podcast is fantastic and your appearance made it even better.

Thanks again to you and the Motley Fool team for continuing to share your stories and your wisdom. Fool on. Kevin McMahon. Well, fool on back to you, Kevin. I, of course, loved reading your note. I played Strat-O-Matic baseball all throughout my youth. My brother Tom and I ran a whole league at our school. We had 11 year olds coming over to our house on weekends to bring out their Strat teams and play head to head. It was a league. We had about 20 people in it. It’s a very fond memory. I do remember my first copy of Strat-O-Matic baseball. I believe it was 1974, and two teams came in it. I got the 1974 Chicago White Sox and my younger brother, Tom, got the 1974 Atlanta Braves. He had Hank Aaron on his team. I didn’t. But I did have Dick Allen, who was just recently recognized as a Hall of Famer himself. Had a lot of fun just Tom and me playing those two teams. We had no other connection to them. We’re lifetime Minnesota Twins fans, but that is such a fun memory for me, and Strat-O-Matic baseball runs all throughout my youth. I eventually decided that pursue the pennant, which was a competing baseball product was even better, a little bit thinkier with a little bit more variety and fun. But I love dice sports games. I grew up playing all of the Strat-O-Matic games. I think at this point, Kevin, my listenership this week, maybe down to just you and me because I’m not sure anybody cares that much more about Strat-O-Matic than I do. But this is an opportunity for me to thank you for your note and to say that Chris Hill has a wonderful podcast and he sent the questions over ahead of time for his money plug podcast, and they were different from the types of questions I usually get if I’m going to be on somebody’s podcasts. I’m happy to answer investing questions all day long. Clearly, witness this podcast. But I also had a lot of fun because Chris’s questions, a lot of them are who you were and where you grew up and what you thought about things as you grew up. I think that’s why you were encountering some new biographical learnings about me, and it was my pleasure to share and keep up the great work Chris Hill with Money unplugged. Mailbag item Number 2. This one from Peter Pastrel DMD. That means, Peter, you are a dentist.

Thank you for taking the time to write in. “Dear, Motley fool”. You write, “I just received the new Rule Breaker Investing book, very excited to read it. Another point for David on Chapter 2 about not adding to your weeds and watering the roses,” Peter writes. Peter is, of course, referencing habit Number 2 of the Rule Breaker investor, which is to add up, don’t double down. I think part of the fun of this podcast going forward is, I can all of a sudden now be relating to the book itself, the six habits, the six traits of stocks, the six portfolio principles, haven’t been able to do that until now, but I think a lot of the questions and the conversation will often be about those six habits, those six traits, those six principles. Peter, you’re doing it right here. I think this is a new wave of mailbag item, and I really enjoy your thinking here. You go on. I used to always average down on my stocks that were down until I started listening to the Motley Fool around 2014. Here are two points, Peter writes. When people average down on their stock cost basis, they are basically saying, Peter writes two things. One, the market, which is generally efficient has this stock wrong. In my wisdom, this stock will go back up, so let me buy more. Not even the most seasoned investment professionals know for sure if this stock will go back up. Then Peter goes on to his point Number 2. What I’m saying by buying more of this down stock is that I’m smarter then the other billion investors that are saying this stock should be down 40% and I’m saying it will go back up a fools small F, Peter writes errand. I totally agree with David in that we should add to our winners and let the down stock go up on its own merit and not my feeble thoughts. Anyway, I bought three copies of the book, one for my son, one for myself, and one for my father for his birthday, 89 years-old today. What a great birthday present.

The Motley fool has made me wiser, happier, and richer. Thank you. Peter D Pastoral DMD. Peter, thank you. I really appreciate you sharing your thinking back. The concept of adding up is against most people’s instincts. It’s certainly, as I point out in the book, against what mutual really that they legally have to do, which is to rebalance to sell off their winners in order to add back to their losers. The idea being, of course, that those losers will come back. At least for Rule Breaker stocks, Peter, in my experience, a lot of my broken bad Rule Breaker stock picks never really do come back in any meaningful way. Rarely is there a remarkable comeback where a horse that was 15 lengths back all of a sudden comes out of nowhere with me adding to it all the way through the finish line. No, most of the time, the horses like secretariat, they get out front. They’re the ones who win the race, they win for us investors, and I’ve been trying to add to it along the course of the race. If you’ve read the book, I’m alluding to you get to invest the whole race, which is portfolio principle Number 5. Very rarely do Rule Breaker stocks make great comebacks. I think the only way really to get poor if you actually try to get poor investing in the stock market, which rises 9-10% annualized. The only real sure way to actually play that into poverty is to become hell bent on adding to a stock that’s down. As it goes down more, you add more. At that point you think, well, if I liked it at 20, I have to like it at 10, and then when it hits six, it’s a combination feeling. It’s on the one hand if I liked it at 20, and if I liked it at 10, I must love it here at six, but it also starts feeling a little bit desperate like I’m going to add money to this because if it just gets back to even, I’ll make money. I don’t think that’s a great set of investing habits. I don’t think that’s the right Rule Breaker mindset. That’s why we much prefer Peter to add up don’t double down and what you’re saying, your two points I agree with. In general, I think the market is generally efficient near term. The market has a very hard time factory in value over the long term, which is where our Alpha sits and why we beat the market and why we beat the pants off the market the longer we hold our stocks if they’re great Rule Breaker stocks. But I do think that you are going against a lot of wisdom if you start saying the market is wrong as your stock declines and you add to it on. That’s where I’ll leave it, wrapping up Mailbag item Number 2. But I have to say in conclusion, Peter, thank you so much for making a gift of my book to your dad. Happy 89 years, Mr. Pastrel.

Rule Breaker Investing Mailbag item Number 3. This one from Michael Baldwin. Thank you, Michael. You write, Hi, there. Was listening to the latest mailbag today. That would be last month, by the way, and thought I might be able to help read the question of share tracking tool. I’ll pause it there for sec. In last month’s mailbag, one of the questions was, how do you actually track your portfolio in a professional manner that is easy and enables you to know exactly how you’re doing compared to the market averages. Including complexities like adding in dividends, maybe even accounting for the implications of taxes on your portfolio performance as well. That was the question. Chief Investment Officer of the Motley Fool Andy Cross and I spoke to that a little bit. We both felt like there wasn’t a great answer, and that’s why Michael Baldwin is coming in with this note. I’ve been using Michael write share site. That’s share as in shariff stock and sight as in your eyesight, sharesight.com for many years. Michael writes, it includes pretty much all indices. It includes dividends, and has various performance tracking metrics, reports, etc. Whilst this is a dead giveaway that Michael is not writing from the United States of America. Whilst it is an Australian/New Zealand based tool for tax tracking purposes, it has taken the process of manually updating spreadsheets and trying to figure out formulas for compounding, while adding to or selling down positions, etc, completely away. I can focus on more important things. I hope this helps Michael Baldwin. First of all, Michael, yes, it does. Thank you. Thank you for sharing that. I love sharing out good solutions that fellow Fools are using and finding helpful. In particular, I think this no can help my Australian and New Zealand listeners because it sounds like that is where Sharesight comes from. Sharesight is a global tool, and anybody can go to sharesight.com and take a look at it, but it does sound like the tax tracking, if somebody wanted to do that is maybe more geared toward the other side of the planet from many of us here in the good old US of A. But it looks like a very clean tool. Clearly, it has a lot of fans, and I will say, having clicked into the pricing, the pricing is a little bit questionable to me as a capital F Foolish investor. First of all, for people who are serious, I do think it sounds pretty good. Not everybody is necessarily looking for professional level tracking of their portfolio and just noticing their pricing and plans. Anybody can use it for free. You get one portfolio that can have 10 holdings. If you pay $7 a month, that’s Australian. I think their listing is $9.33 US dollars per month, billed monthly.

Basically, pay nine bucks a month, you can track one portfolio with 30 holdings. If you pay $18 Australian, that would be $24 a month. You can track four different portfolios with unlimited holdings, and if you pay up a few more dollars than that, you get even more than that. I think in particular, what I’m looking at is paying $9 a month to track one portfolio. I’d probably be OK with that if I’m quite serious about this. My problem is you can only have 30 holdings in that portfolio. I would suggest to Sharesight that if somebody wants to track their portfolio, and I’m really speaking as an armchair investor to a lot of armchair individual investors out there, lot of us are going to have more than 30 holdings. If you’re paying attention to your GKC and I’m just going to leave that acronym there and wink at those who know what I’m talking about, you probably are going to have a growing number of holdings. You might even have well more than 30 when you start your portfolios, so you’d have to go from that $9 up to $24 monthly just to track a portfolio with more than 30 holdings. That would be my only misgiving, Michael Baldwin, but thank you for bringing Sharesight to our awareness. You concluded your note by saying, hope this helps. It did. Fool on, my friend. Let’s move on to mailbag item Number 4. Mailbag item Number 4 is from Joe. Last month’s mailbag began with this note from Joe. It was short, so I’m just going to read it again. This is what kicked off August. Hi, David. In February of this year, I turned all of my focus from sports betting to investing. I grew up in a house where we didn’t talk about money and I was clueless on the stock market. I knew I was missing something, so I decided that at the age of 43, it was time to get serious about planning for retirement. What a mistake waiting this long, but I’m glad I at least found my path now, and I’ve gotten my 10-year-old started off on the right path. Motley Fool Money and the Rule Breaker Investing podcasts were the first two that I started listening to in order to learn more. I’ve learned so much from you and your team. Thank you. Joe concluded his note shared last month with this. My question is this, he wrote, “If you were a new investor starting with your first $1,000 today, would you be more likely to invest in Rule Breaker style exchange-traded funds, ETFs, rather than in individual stocks?” Fool on.

Joe. That was the note last month, and I’m not going to re answer that. But if you’re a new listener, that conversation I had with Motley Fool Chief Investment Officer Andy Cross. Andy and I just kicking around Joe’s question, I think that’s worth listening to if you didn’t get a chance. It let off last month’s Mailbag. It was Mailbag item number 1 in fact. In fact, the podcast title of that whole mailbag was Sports Better Turned Investor. Well, let’s now get to this month’s mailbag item number 4, this one from Joe. Hi David, I just wanted to thank you and Andy for fielding my question and all of the discussion around it. I really appreciate your help and support. The book is on pre-order. I’m excited to dig more into all of it, especially the portfolio management piece. Thank you yet again and Fool on Joe. Well, I just wanted to share that Joe because I really appreciate you closing the loop. I love the journey that you’re on. My friend Alicia Aldrich here who runs Motley Fool PR. She’s been doing a lot of booking. Thank you, Alicia, for the work you’ve been putting in yeoman’s work here over the last few weeks, booking me on different shows and podcasts and that’s going to continue. Alicia dropped me a short note this week and she said, just for fun, think about sports betting versus investing because she knows I’m passionate on this topic. Alicia said Americans wagered $150 billion in 2024 on sports betting. Joe, it wasn’t just you.

Alicia went on projection show that there will be a record $30 billion in wagers just on this year’s National Football League season alone. I did include a couple of pages in Rule Breaker Investing about sports betting. I always want to point out two things. First of all, I think betting is fine. I’ve made bets myself. I think speculating is a great thing to do in life, just in moderation, of course, and also math, which is my main point about sports betting. The math is completely against you. Every sports bet is generally a 50/50 prospect. Let’s say you put down $100 with your friend. The house is going to take five or 10%, so five or 10 of your dollars just disappear, and let’s say with the $90 left, one of you is going to beat the other and walk away with their 100 plus the 90 from their friend. But if you just notice $10 disappeared from the $200 that were wagered. If you just do that for, let’s say, 20 consecutive sports bets, well, that $10 is disappearing each time, so those original 200 that were wagered are basically wiped out altogether by the house, and you’re likely to have lost money. In fact, anybody who consistently bets on sports is very likely to run an expected negative return. That means you’re losing money, not making it in volume over time. I had a lot of fun from my hotel room in New York City watching the Detroit Lions take on the Baltimore Ravens on Monday Night Football this week. It was a great game. I really enjoyed watching that game, and I really appreciate not betting on it because I didn’t have to sweat out my bet. I have had bets on games, and I often don’t enjoy the game that much because I’m just hoping that, in this case, a lot of people were hoping that the Ravens would cover their 4.5 point favorite. The Baltimore Ravens playing at home last night were a 4.5 point favorite. Half the people betting on Monday night expected the hometown Ravens to win by five points or more, half the people. History will show the Ravens did not. They lost by eight and a lot of money just disappeared overnight. Those who were betting for the lions against the spread, they’re happy, but they also paid five or 10% for the privilege of winning that bet. These days, if you invest in the stock market, commissions are down to about $0 per share, and Joe, you already know this. I’m speaking to those who may not. The stock market averages a 9-10% annualized gain. The opportunity cost that anybody in volume is paying for the privilege of getting to bet the Lions or the Ravens or whoever you’re betting on next week.

Again, if it’s all good and this is with a friend and it’s not a big amount of money for you, I’m totally fine with that, but anybody who’s taking this seriously, and I realize the whole sports media world and a lot of advertisers take betting very seriously these days, they’re really steering many people down the wrong track. If you care about your money, if you want to retire, especially if you want to retire early, I think, well, let’s just put it this way. I think you should be like Joe. Joe, thanks for your note. Fool on. Closing out this week, Rule Breaker Investing Mailbag item number 5, this one from Gorov Kumar. Gorov thank you for this wonderful note. Hello, David, and the Rule Breaker Investing team. I’ve been thinking about writing a post for the Mailbag, Gorov writes for quite some time. When I heard David on the Money and Plug podcast with Chris Hill this past week, I decided to do so and he numbers his points. One, a while back, David did a couple episodes with Jason Moser about getting kids started with investing. After listening to that episode, I decided to start investing for my girls, eight and four at the time in a custodial brokerage account. I decided at random to invest $100 for every year at their birthday in that account. $800 at their eighth birthday, 900 at their ninth, etc, and I’ve kept that going so far. The stocks that I bought in those two accounts were all Motley Fool recommendations, such as Netflix, Amazon, the Trade Desk, Mercado Libre, Starbucks, etc. I have not sold a single share in those two accounts since then. My kids accounts have done way better than my personal accounts where I’m a little more aggressive. Gorov goes on when I heard in the money unplugged episode that David, when you were managing your wife’s portfolio and your wife’s account was performing better than your account, I could totally relate to that. I want to thank you and Jason Moser for those episodes to help me get started investing for my girls.

Those accounts have turned a few hundred dollars into a substantial sum for my girls, and I’ve told them that as long as they don’t sell, I will keep investing $100 for every year on their birthday for as long as I can. I’m just going to pause it there for a sec. What a great dad. Gorov you go on. I recently asked my 17-year-old daughter because yeah, those who may not be familiar with this, that Jason Moser etc podcast that we did years ago was about nine years ago. Gorov’s eight-year-old is now 17, I want to thank Jason as well, again, and anybody who’d like to Google Rule Breaker Investing, get your kids started investing. You will find my two-part series dedicated to getting your kids started investing. Gorov, I think you’ve started to establish some of your own best practices. I love how you’ve gamified it. I love what you’ve done here. You close out point number one with this. I recently asked you write my 17-year-old daughter to calculate how long it will take for her account to turn into $1 million if we don’t invest a single cent at this pace. When she calculated that, her eyes lit up and she said something that was music to my ears. She said, Gorov writes, “Hide the username and password of this account from me and don’t give it to me when I turn 18.” Well, that was the first of Gorov’s two points. I think one of the things I love about this podcast and especially my mailbags is just getting to share other people’s great ideas, your inspirations, what you do for yourself, what you do for your kids. In this case, Gorov, I think you’ve opened some eyes and probably raised some smiles this month and probably there will be some other parents who start to do exactly what you did nine years ago.

They’ll start this week because they heard your story through this podcast. This podcast mailbag is only as good as the mail that comes in and the mail that comes in is often so very good. Let’s go on to Gorov’s second concluding point. You’re right. I’ve been investing with The Motley Fool since 2012 and done decently. In 2021, we decided to build a new house and we use proceeds from some of my winners like Netflix to build the new house. When you said on the Money Unplugged episode, don’t sell Netflix to build your house, Gorov writes my jaw hit the floor because that’s exactly what I did. I was initially very happy that I sold Netflix in 2022 when it dropped from $700 a share to $250 a share. Yeah, that happened, 2022, not so long ago. But not so happy you write now seeing it cross $1,200 a share. However, I was talking to my wife the other day and we both agreed that the new house has brought us immense happiness, and we’ve been able to create so many good memories in this house. We don’t regret the house at all, but selling winners like Netflix and Amazon, that does hurt some. Just wanted to send this note and share my gratitude for sharing your thoughts so freely. I look forward to the new episodes every week. I just received your book, Rule Breaker Investing earlier this week, finished the first two chapters. It’s a great read so far. This will make a great gift to anyone interested in learning about investing. PS Gorov writes, “My daughter, who is a high school senior is also reading this book and actually she shared a quote from this book in her college essay, which is related to investing in financial literacy.

She’s also applying to UNC Chapel Hill for the Moorhead Kane scholarship program. It was such a happy coincidence hearing on the Money Unplugged episode that you were also a Moorhead Kane scholar.” Thank you, Gorov Kumar. Thank you, Gorov. I saved this one to last because there’s a real connection across multiple dynamics here, synchronicity happening with this note, whether it was that you and I both sold some Netflix to buy our houses, and yet while that was a horrible mathematical move, neither of us regrets it because why do we invest in the first place? To buy a house, to build a house, or to put a kid through school, or to retire early. That’s why we invest. While I don’t think I’ve ever been a good real estate investor, I’ve never once regretted any house. I’ve only bought a few that I’ve ever lived in because I love living in that house. That’s why we invest. My house is much more meaningful to me than the invisible shares that I see on my brokerage statement, whether it’s printed out on paper or I’m viewing it on a glowing screen, why we invest is exactly what you shared this week. It’s not just about a house or Netflix. It’s also about a child, in this case, more than one of them and turning them on to investing. One of the main points I’ve been trying to make as I do media around New York City and the Internet’s writ large, maybe my main point is, this is what investing is. Rule Breaker Investing is just one form of it and we practice other forms just at the Motley Fool. We’re motley.

Anybody who’s been a member of ours for a long time knows not everybody at my own company would agree with me on any given stock pick or on any single page of my book. We are Motley. But I think one thing that is true of the Motley Fool and I think always will be, is that we’re there to invest. As I say habit number 3, invest for at least three years. That’s right. It’s very strange for me to do a lot of financial media when most people are traitors giving advice in the very near term about what’s going to happen this fall or in the next earnings quarter. It’s such a foreign language, I’m often speaking when I speak the language of investing, but I really hope that this book helps turn the tide for many Americans and many people living worldwide because investing is such a better practice than trading. Investing is a way better practice than sports betting, investing starting with its etymology, which I break down in the book and provide some visuals and I hope some inspiration investing is a very powerful act. It’s a beautiful word. It’s obviously one of my favorite words. Your note, Gorov Kumar is replete with investing in more than one form. I also wish the very best to your daughter as she applies for a scholarship program at UNC Chapel Hill, which improved my life in a way that I will always be grateful for. Thank you for all the tweets.

Thank you for all the mailbag items. I really appreciate. It’s obviously a special week for me. I obviously appreciate. That’s why I let off with a thank you and I’m going to close with a thank you. This is an unusual mailbag because it feels self-indulgent at different points, and I apologize if it ever did Chloe. Yeah, I hadn’t written a book though for 15 years and I’d been anticipating some of you had to all year long this past week in the book coming out. It’s understandable the mailbag would be dominated by it. By the way, just to mention something at close here that I mentioned early on, I would love for you to send me any questions that you have aroused from reading the book because I’m going to keep building out a mailbag, giving answers to the most frequently asked questions. A reminder, the Rule Breaker Mailbag happens every month thanks to this email address, [email protected]. Of course, you can also tweet us on Twitter X @rbipodcast. I want to thank my compadre, Brian Richards at the Motley of our top leaders at the Motley Fool, who has recently taken control of the @rbippodcast account. It really had been sitting dormant there for some years now, and he’s very actively using it. It’s a good follow too for Rule Breaker fans. Let’s bring on October. Shall we? Fool on.

Why do we both crave money and resent it? Why do some people sabotage their financial futures in the name of short-term comfort? And why is your brain — not the stock market — the biggest threat to your wealth?

In this conversation, we explore the surprising ways that psychology and money intertwine. Our guest, Dr. Daniel Crosby, is a behavioral finance expert, psychologist, and bestselling author of The Soul of Wealth, The Behavioral Investor, and The Laws of Wealth. His research dives into how our emotions, childhood scripts, and personalities shape the financial decisions we make every day.

Dr. Crosby shares why investing is an act of optimism, why income matters more than coupon clipping, and how our spending reveals truths about who we really are — even when we don’t realize it..

Key Takeaways

• Money is a mirror. The way you earn and spend reflects your real values, not just your stated ones. Tracking your money reveals gaps between who you say you are and how you actually live. 
• Income drives wealth. Frugality matters, but once the basics are handled, your long-term financial future is determined more by growing your income than by cutting costs. 
• Short-term comfort is costly. The biggest threat to your wealth isn’t the market — it’s the temptation to prioritize momentary relief (panic-selling, stress spending) over your long-term goals.

Resources & Links

Closing

This episode reminds us that building wealth isn’t just about math — it’s about mindset. The markets may fluctuate, but the greatest risks and rewards often lie within our own psychology.

If you enjoyed this conversation, share it with a friend, subscribe to our newsletter at affordanything.com/newsletter, and connect with our community at affordanything.com/community.

You can afford anything, but not everything. Choose wisely.

 

Chapters

(3:24) — Does money really buy happiness? Rethinking the $75k income myth.

(8:48) — Our conflicted relationship with money: Love, resentment, and the paradox of wealth.

(10:32) — Childhood money scripts: How early beliefs still drive adult financial behavior.

(16:10) — Personality traits & money outcomes: Why agreeableness and neuroticism matter.

(20:15) — Investing as an act of optimism: Human progress, markets, and long-term growth.

(26:39) — AI, work, and the future of wealth: Why EQ may outpace IQ in tomorrow’s economy.

(31:46) — Habits vs. willpower: Why automation and environment beat discipline.

(36:28) — Frictionless spending: How Apple Pay and subscriptions fuel overspending.

(39:32) — Offense vs. defense in wealth: Why income matters more than extreme frugality.

(55:16) — Chronic vs. episodic mistakes: Small leaks, lost compounding, and long-term damage.

(58:24) — The pre-mortem exercise: A Stoic-inspired tool to prevent financial failure.

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What if one of the best ways to get wealthy is to trick yourself into thinking you’re poor?

It sounds counterintuitive, even ridiculous. But after decades of saving, investing, and observing how people behave around money, I’ve realized one thing: abundance often breeds complacency.

When you feel flush, you spend more, work less, and get sloppy. When you feel broke—even artificially—you hustle harder, spend carefully, and grow wealth faster. And as we all know, the path to financial freedom comes down to one formula: save and invest as aggressively as you can, for as long as you can. The problem is sustainability.

The ~5% national median saving rate simply isn’t enough. Needing 19 years to save one year of expenses means you’ll never be free. Aim for at least 20%, and if you can push yourself to hit 50% for 10 years, your future self will thank you many times over.

Feeling Lazy And Unmotivated After Summer Vacation

Ever since coming back to San Francisco from my five-plus weeks in Honolulu, I’ve been feeling more lazy than usual. I started wondering why everybody doesn’t live in a place like Hawaii, where the weather is always great and the vibes are always friendly. Grinding so hard in San Francisco seemed pointless and a surefire way to burnout.

You don’t have to be rich in Honolulu because the beaches, hikes, and sunshine are free and accessible for all. If you’re a local, you even get Kamaʻāina rates for golf and other attractions, saving you even more money. Although I spent three-and-a-half weeks helping remodel my parents’ in-law unit, I felt much more at ease doing less.

The problem with coming back to San Francisco is that the vast majority of people are hustlers. Most are trying to climb the corporate ladder or build a company for greater status and money. These actions run counter to the FIRE lifestyle of giving up money and status for freedom.

But given I’ll be stuck in San Francisco for at least the next four years, I need to be careful not to act too lazy. Because if I do, I’ll start feeling FOMO from the ongoing AI/tech boom. And feeling left behind is one of the worst feelings you can have.

A Solution to Getting Rich Is to Feel Poor

As I found myself waking up later and later, I realized I needed a way to motivate myself again. Given I’m no longer a stay-at-home dad, increasing productivity felt required.

Then one day, while checking my banking app, I noticed that my checking account was in the red by $109.97. Doh! I had paid my annual life insurance premium automatically and forgot to leave enough in my checking account.

Since making a terrible two-year mistake with a life insurance policy, I’ve been intentionally keeping my checking account light to avoid wasteful spending. And with a free $5,000 overdraft line of credit, being down $100 wasn’t a big deal. I topped it up from money from our joint account.

But here’s what mattered: seeing red on my account made me perk up and take notice.

To be frank, I felt poor. How could I, with multiple streams of passive income, not even have enough to cover a life insurance payment? Yet with that temporary feeling of not having enough came a renewed sense of urgency—to stay on top of my finances and grind once more.

Living on the Financial Edge Makes You Focus

A couple of weeks later, rental income, dividend income, and bond income replenished my checking account. But the lesson stuck with me.

Having a checking account flush with cash earning 0.1% interest was actually demotivating. It pulled me back to the lazier state I’d fallen into after returning from Honolulu.

So I decided to transfer out nearly all my excess checking funds—keeping just enough to cover upcoming bills—into my Fidelity brokerage account. The goal was to always try and keep my checking account always close to $0 as possible. That way:

1. My idle cash could earn ~4% in a money market fund at my brokerage account.
2. I could dollar-cost average into stocks or bonds easily during market pullbacks.
3. I could allocate more into alternatives like venture funds to hedge against the AI revolution for my kids’ future.

Now, whenever I log into my banking app, I see hardly any money. And you know what? That scarcity forces me to think twice before swiping my credit card since I don’t have enough funds to pay by debit card. If a purchase isn’t a “hell yes!”, it’s a no.

Instead of ordering takeout, I’ll cook at home or live off my insides and fast. Instead of buying new sneakers, I’ll finally wear the ones collecting dust in my closet. This artificially imposed scarcity has reactivated my discipline. And long-term discipline is what we all need to FIRE.

Recreating the Hunger of When You Had Nothing

The whole idea of keeping yourself financially lean is to recreate the hunger of your early days, when you had little to nothing. If you want to achieve FIRE, sacrifices must be made.

Back in 1999, fresh out of William & Mary, I shared a studio apartment with a friend to save on rent in NYC. I’d get to the office by 5:30am and stay past 7pm to connect with colleagues in Asia before heading home. It was nice to also gain access to the cafeteria for a free dinner and some extra food for breakfast.

I put on 15–20 pounds, developed TMJ, and dealt with plantar fasciitis, all from the stress of hustling on Wall Street for money. But those sacrifices laid the foundation for everything that followed.

By living frugally after promotions, I was able to bank the difference and invest aggressively. That discipline compounded over decades, and has made living far easier today.

However, as I grind toward a new passive income goal by December 31, 2027, I see the wisdom of returning to that mindset. We must find ways to continuously save and invest more if we want to one day stop trading time for money.

The Bull Market Can Make You Weak

Bull markets are intoxicating. When your investments are compounding faster than your active income, it feels like you’ve hacked life with a cheat code. You start to believe you can’t lose.

But complacency is dangerous. I watched it happen in 2007. People levered up, bought multiple properties with no-money-down loans, and assumed the party would never end. By 2009, many had lost everything and had to rebuild from scratch. I was one of these people who foolishly bought a vacation property I certainly didn’t need in 2007. It ended up declining in value by 50%.

I don’t want to relive the trauma of seeing my net worth fall 35–40% in six months. And I don’t want that for you either.

That’s why artificially feeling poor—especially in bull markets—isn’t just a motivational trick. It’s a safeguard against overconfidence and reckless behavior.

Practical Ways to Feel Poor To Stat Disciplined When Times Are Good

If you’d like to try this strategy yourself, here are some ideas:

1. Keep your checking account lean. Only maintain 1 month of expenses in checking. Move the rest into higher-yielding accounts in your brokerage.
2. Auto-transfer your surplus. Each payday, sweep extra funds into a brokerage, high-yield savings, or investments. Out of sight, out of mind.
3. Challenge yourself with no-spend weeks. Pick two weeks a month to avoid discretionary purchases. You’ll realize how much you can cut.
4. Simulate living paycheck-to-paycheck. Cap your monthly spending at a fraction of your income, and redirect the rest into investments.
5. Revisit your “broke college” habits. Cook cheap meals, ride public transit, share resources, and embrace minimalism—even temporarily.
6. Audit your subscriptions. Cancel what you don’t truly need. Every forgotten $10/month service adds to lifestyle creep. Did I just see Apple raising their Apple TV+ by $4 to $14/month?
7. Practice gratitude daily. Remind yourself how far you’ve come, and that you can survive with less.

Artificial scarcity doesn’t mean living in fear, it means using small doses of discomfort as a tool to stay sharp, disciplined, and motivated. It’s about keeping things real and humble, while you build ever more wealth.

Embrace The Paradox of Wealth

So if you want to grow rich, adopt a broke mindset. If you can endure that self-imposed discipline, you’ll almost certainly end up wealthier than the average person who spends freely without intention.

In the end, wealth isn’t just about the numbers in your accounts. It’s about having the mindset to stay focused for decades. And sometimes, the mindset that works best is remembering what it felt like to have nothing, and making sure you never go back.

Readers, do you artificially make yourself feel poor to grow rich? In a country with so much abundance, how do we do a better job to combat laziness so that we can continue to build generational wealth?

Free Financial Analysis Offer From Empower

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Think of it as holding up a mirror: a seasoned expert, who builds and analyzes portfolios for a living, can uncover hidden fees draining your wealth, inefficient allocations slowing down your growth, or overlooked opportunities to put your money to work harder. Sometimes that outside perspective is exactly what you need to sharpen discipline and stay hungry.

The statement is provided to you by Financial Samurai (“Promoter”) who has entered into a written referral agreement with Empower Advisory Group, LLC (“EAG”).

Subscribe To Financial Samurai 

Pick up a copy of my USA TODAY national bestseller, Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled over 30 years of financial experience to help you build more wealth than 94% of the population—and break free sooner.

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Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

To celebrate Millionaire Milestones: Simple Steps To Seven Figures making the USA TODAY national bestseller list, I want to share how you might feel and what you might do as you hit various levels of wealth. Perhaps by sharing, I’ll motivate you to save and invest more aggressively. We’ll start with reaching your first million, then move on to $5 million, $10 million, and $20 million.

I stop at $20 million because once you surpass that threshold, there’s not much left you can spend money on to meaningfully improve your lifestyle. Beyond $20 million, building more wealth simply becomes a game, a personal challenge, or an exercise in greed.

As the Chinese philosopher Lao Tzu once said, “A journey of a thousand miles begins with a single step.” When it comes to building wealth, you must be intentional. Treat managing your finances with the same passion and precision you give to your favorite hobby.

Those who wing it will wake up a decade from now wondering where all their money went. But those who stay intentional—reviewing their finances regularly and investing in their financial education—will build lasting wealth. More importantly, they’ll unlock the freedom to live life boldly, on their own terms.

1. Reaching Your First Million: Relief, Validation, and a Sense of Real Possibility

When you hit your first million dollars, you’ll feel an overwhelming sense of relief first and foremost. You’ll think to yourself, “Finally, all those years of saving, investing, and grinding have actually amounted to something tangible.” It’s a huge milestone you should be proud of.

It’s like crossing the finish line of a marathon where the prize isn’t just a medal, it’s the ability to breathe a little easier. You won’t necessarily feel rich, especially thanks to inflation, but you will feel validated. You’ll realize that as an employee, building wealth is not just for other people or institutions, it’s for you, too.

Your first million will also give you a huge psychological unlock. Suddenly, you’ll see possibilities everywhere. The fear of financial ruin won’t vanish, but it will shrink given you’ll be able to generate $40,000 – $45,000 a year in passive income, risk-free at today’s interest rates. You’ll start to imagine what life might look like if you really ramp things up.

Most importantly, the first million is where you internalize a crucial truth: the snowball gets bigger on its own. Saving that first $250,000, as I write in my book, might have felt like climbing Everest. But once you have $1 million compounding at 5%–10% a year, you’re talking about $50,000–$100,000 a year in passive growth without lifting a finger.

You can aggressively play offense now, not just prevent defense. You can afford to take more risks, something I wish I did more of when I was younger.

Common Pitfalls Getting to $1 Million:

• Lifestyle creep: As income rises, spending rises even faster for the undisciplined.
• Investment FOMO: Chasing the next hot trend (and blowing your finances up) instead of sticking to a plan.
• Quitting too early: Giving up on saving or investing because the early gains seem too small.

2. Reaching The $5 Million Milestone: Confidence, Options, and a Taste of True Freedom

Once you reach the $5 million milestone, a quiet but profound confidence starts to settle in. You no longer have to calculate whether you can afford the organic blueberries at Whole Foods. A $7,000 unexpected home repair or even a $50,000 investment mistake that plummets 20% soon after no longer feels like a big deal.

You also start to realize you have options. A $5 million net worth can throw off $150,000–$300,000 a year in passive income, depending on how it’s invested. That’s enough to exceed the median American household’s entire pre-tax income of ~$80,000 without working another day in your life.

If you’ve been stuck in a soul-sucking job or run a business that gives you ulcers, $5 million lets you walk away. But of course, try and negotiate a severance package so you have an even greater financial cushion when you do. If you’ve been dreaming of living abroad, working part-time, or starting your own business, $5 million gives you the luxury of choice.

Unfortunately, you’ll still worry about your finances.What if the stock market crashes? What if rental income dries up? What if health care costs explode? But you will rationally make contingency plans if any of these things happen.

Overall, your anxiety will diminish because you know you have true staying power. In a previous Financial Samurai poll, $5 million was the ideal net worth to retire with, followed by $10 million. You are set for life if you remain vigilant with your finances.

What Happened To The $3 Million Net Worth Milestone?

Some readers have asked why I skip the $3 million milestone, given the jump from $1 million to $5 million is large. I agree it’s a notable step.

Hitting $3 million is a solid financial feat—it can free you from a bad job or open new doors—but it doesn’t feel much different from $1-$2 million. I chose to highlight $5 million because that’s when the sense of freedom and financial security starts to feel exciting again, much like hitting your first million.

Common Pitfalls Getting to $5 Million:

• Overleverage: Taking on too much debt or trading on margin thinking it’s a shortcut.
• Burnout: Pushing too hard at the expense of health, family, and happiness.
• Status signaling: Overspending on cars, homes, watches, and jewelry to “show” you’ve made it. It’s interesting, but some of the most insecure people I’ve met are also those with net worths close to the $5 million mark.

Here’s a fun clip from one of my favorite TV shows, Succession, which pokes fun at how $5 million is barely enough if you live in an expensive city like New York. You may not feel rich with $5 million in NYC, SF, LA, Seattle, or Boston, but you should feel comfortable enough.

Looking Back At Retiring With $3 Million In 2012

I left my banking job at age 34 with a net worth of approximately $3 million. Adjusted for a 4% compound annual inflation rate, that’s about $5 million in today’s dollars.

At the time, $3 million felt like enough because I only had myself, and eventually, my wife to take care of. My investments were generating around $80,000 a year in passive and semi-passive income. Combined with a severance package and the support of my wife—who was 31 then and willing to work for another three years—I felt it was time to peace out.

Still, I was nervous and insecure about leaving my day job so young. Looking back, I probably should have worked for another three-to-five years to further solidify my finances. With $3 million, I was much more argumentative in the comments section too. Now I’m not.

That said, everything has worked out because I found purpose. I found something I love to do that generates supplemental retirement income, and, more importantly, I became a father. In the end, retiring early gave me the flexibility to build a more meaningful and fulfilling life.

3. Reaching The $10 Million Milestone: Abundance, Status, and Subtle Shifts in Relationships

At the $10 million milestone, your world view may shift again. Scarcity thinking—the nagging belief that there’s never enough—starts to dissolve, but never truly goes away.

With $10 million, you’ll feel an underlying abundance mindset take over:

• You can generously tip service workers without thinking twice.
• You can say yes to experiences you once would have passed up because of cost.
• You can invest in your health, relationships, and personal growth without financial hesitation.
• You can eat wagyu steaks and toro sashimi until you’re sick of them both.
• You’re part of the richest rich class who didn’t get rich through index funds
• Upgrading to Economy Plus or even first class is no problem
• People don’t piss you off as much anymore
• You can more easily migrate to another country to save on taxes
• Perhaps best of all, you can easily speak your mind and stand up for yourself without fear of financial ruin

Being A Multi-Millionaire Can Have Its Problems

At this level, status becomes more visible, whether you like it or not. People may treat you differently once they know—or sense—your wealth. Friends and family might ask you for favors, loans, or business investments. You’ll need to develop a thicker skin and clear boundaries.

With $10 million, you’ll probably embrace Stealth Wealth like a secret agent trapped behind enemy lines. You didn’t spend all these years building your fortune just to get hit up for handouts, judged, or peppered with investment pitches every time you leave the house or turn on your laptop.

As a millionaire ten times over, people will be quicker to judge your actions and far less sympathetic when you’re feeling down. Even though millionaires need love too, people may simply not care if you’re feeling down and out. Hence, you purposefully become more guarded with your friends and acquaintances.

Thankfully, some of your relationships will deepen. You’ll naturally gravitate toward people who genuinely don’t care about your money.

No longer will you feel the need to maintain relationships just because someone holds sway over your financial or career future. Instead, you’ll start surrounding yourself only with people you truly enjoy being around. Say goodbye to toxic relationships!

Having A $10 Million Net Worth And Children

If you have children, reaching $10 million also changes how you think about legacy. How do you empower your kids without spoiling them? How do you prepare them for a world where they don’t have to struggle financially the way you did?

Fat FIRE parents might worry even more because they no longer have traditional day jobs that force them into the office 40+ hours a week. At least if you have a day job and a $10 million net worth, your children will know that you are working hard.

As a result, FIRE parents will likely have to make up a “trust fund job” to demonstrate their work ethic and purpose to their kids. Otherwise, they might ruin their perspective on life and money.

At the same time, with so much wealth, you may naturally start toying with the idea of making your kids millionaires too. You know firsthand how hard it was to get here, so it’s only natural to look for ways to help them shortcut the journey.

Just be careful. Taking away your children’s drive to become financially independent could end up being one of the greatest disservices you do for them. As you know, one of the greatest feelings is achieving something mostly on your own.

Common Pitfalls Getting to $10 Million:

• Neglecting tax efficiency: At higher wealth levels, minimizing taxes becomes just as important as investing well.
• Poor estate planning: Without smart legal structures, you risk losing millions to taxes or probate.
• Not cashing out or diversifying into safer assets: Outsized income and company valuations do not last forever. Without diversification, your net worth swings can be huge.

4. Reaching The $20 Million Milestone: Peace, Purpose, and a Reduction In Material Desires

Crossing into $20 million territory feels less like a major “event” and more like an arrival. You realize there’s almost nothing left to buy that will materially improve your happiness.

A $50,000 watch won’t make you feel better than a $500 one, so you don’t get one. A $200,000 car won’t make you happier than a $50,000 one, so you drive your current car until it breaks. You could buy a third or fourth home, but would you even have time to enjoy them? You can’t because you can only live in one place at a time.

The only real splurges you can enjoy with a $20+ million net worth are flying private, renting vacation homes for $50,000+ a month, and paying for $60,000+/year private grade school without worry. You could do these things with “only” a $10 million net worth too, but you’ll feel the expenses more acutely.

But even with $20 million, will you really be willing to spend $120,000 on a roundtrip private jet flight from San Francisco to Honolulu when four first-class seats cost just $10,000? Probably not. The more disciplined you are with your personal finances, the less likely you’ll be to splurge on such unnecessary luxuries.

You might also finally feel like you’ve won the lottery, as you could easily generate $1 million a year in almost risk-free income for the rest of your life. The happiest people with this type of outsized wealth recognize their luck and never forget it.

You start thinking about legacy in a more profound way:

At the $20 million milestone, the real luxury becomes time, health, and relationships.

• How can I make an impact beyond myself?
• Who can I help with this abundance?
• What institutions or causes will outlive me?
• Will my children grow up to be outstanding citizens who make something of themselves?

Ironically, at $20 million, if you’re not careful, you risk losing your edge. The hunger that fueled you to work harder, save more, and invest smarter might start to fade. That’s why having a purpose beyond money becomes so crucial.

In addition, once money is no longer a problem, all your other problems come into sharper focus. Neglected your spouse and children on your path to multi-millionaire status? That regret may now feel overwhelming as you can’t get that time back. Prioritized your career at the expense of your health? Suddenly, nothing seems more important than getting fit so you can live longer now that you’ve won the lottery.

If you ever reach this level of wealth, never voluntarily reveal how much you have. Let others guess, but never confirm. Instead, throw them off the scent by looking and acting as normal as possible. Your health, happiness, and safety depend on staying humble and low-key. If you must share something, let it be your generosity.

Your Financial Worry Might Actually Rebound

Ironically, reaching higher levels of wealth can bring back financial anxiety. The more you have, the more there is to lose. A 20% decline could erase $4 million to $16 million. It’s a gut-wrenching amount, even if you’re still financially secure. That’s why your mindset naturally shifts toward capital preservation, all while trying to stay ahead of inflation.

One reason real estate and private investments become more appealing is that you don’t see the daily price swings like you do with public stocks. With your money locked up for 5 to 10 years, you’re less exposed to the emotional rollercoaster of market volatility. As a result, you are more likely to feel at ease.

If you’re looking to diversify your real estate investments and generate more passive income, check out Fundrise, my preferred private real estate and venture capital platform. Fundrise manages around $3 billion in assets for over 380,000 investors. I’ve personally invested over $300,000 in their commercial real estate and venture capital offerings. They’ve also been a long-time sponsor of Financial Samurai.

At this stage, the real battles are psychological. You may find yourself wrestling with how you should feel about having outsized wealth. How dare you feel sad or ungrateful, but you sometimes do. Guilt is an emotion that sometimes emerges as you wonder why you?

In time, you might even downplay your financial success, convincing yourself you’re not as rich—or as lucky—as you truly are.

Common Pitfalls Getting to $20 Million:

• Losing your drive: Without new goals, it’s easy to plateau since nobody needs more than $20 million.
• Isolation: Wealth can unintentionally distance you from old friends and even family. Stay grounded, unless you proactively seek out friends who also have a similar level of wealth.
• Might get trapped in a bubble: Your expectations for how to spend, earn, and think about money can run completely counter to the 99.5% of the American population who have less.

Wealth Is Built on Thousands of Micro-Decisions

Each millionaire milestone you reach brings a sense of satisfaction. But it’s the $3 million, $5 million, $10 million, and $20 million marks that tend to feel the most significant.

None of these feelings—relief, confidence, abundance, joy, or peace—happen by accident. They happen because you took thousands of intentional steps over years, sometimes decades.

Remember:

• Every $100 you invest instead of spend
• Every hour you spend learning and creating instead of mindlessly consuming
• Every risk you take to level up your skills or career

It all adds up.

Time To Focus

Building wealth is a straightforward formula, but sticking with it takes resilience. Inflation will keep shifting the targets, and today’s milestones may look modest in thirty years.

But with enough discipline, patience, and purpose, you can achieve more than you ever imagined. The real reward is not just reaching a number, but growing through the process—learning, adapting, and gaining the confidence that comes from doing the work.

If you want to create a life of freedom for yourself and your children, take the first step today. You may find that the journey itself becomes the greatest part of all.

The Next Million Dollar Windfall: Investing In AI

One of the ways I plan to make another million dollars is by investing in private AI companies. Since private companies are staying private for longer, more of the gains are accruing to early, private investors. It only makes sense to allocate more capital to this space.

I believe artificial intelligence will significantly disrupt the labor market in the future, potentially making it harder for my kids to find fulfilling careers. To hedge against this possibility, I’m investing in both private and public AI companies. That way, if AI does end up reshaping the job landscape over the next 20 years, our AI investments could perform exceptionally well.

Check out Fundrise Venture, an open-ended product accessible to all. It invests in the following five sectors:

• Artificial Intelligence & Machine Learning
• Modern Data Infrastructure
• Development Operations (DevOps)
• Financial Technology (FinTech)
• Real Estate & Property Technology (PropTech)

Roughly 85% of Fundrise Venture is invested in artificial intelligence in some capacity. In 20 years, I don’t want my kids wondering why I didn’t invest in AI or work in AI!

The investment minimum is also only $10, making it accessible and easy to dollar-cost average in. Most venture capital funds have a $250,000+ minimum. You can see what Fundrise is holding before deciding to invest and how much. Traditional venture capital funds require capital commitment first and then hope the general partners will find great investments.

I’ve invested $253,000 in Fundrise venture so far, and plan to keep investing until I build a $500,000 position to hopefully make another $1+ million return within 10 years. There are obviously no guaranteed returns when it comes to risk assets, so invest according to your risk tolerance and goals. Fundrise is a long-time sponsor of Financial Samurai. Our investment philosophies are aligned. 

Pick Up A Copy Of Millionaire Milestones Today

As I wrote in my USA TODAY national bestseller, Millionaire Milestones: Simple Steps To Seven Figures, “If the direction is correct, sooner or later you will get there.” Make sure you have the right resources to point you in the right direction.

Good luck on your financial journey. If you want to become a millionaire or multi-millionaire, my book will help you get there. You can pick up a copy on Amazon, which has the best sale.

For those of you who’ve reached these millionaire milestones, how did you feel after hitting each one? Which financial milestone had the most lasting impact on your lifestyle and happiness? I’d love to hear your story—what changed for you, and what did you do differently afterward?

Subscribe To Financial Samurai 

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To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

How You’ll Feel Reaching Various Millionaire Milestones ($1-$20M) is a Financial Samurai original post. All rights reserved.

Here’s the thing about personal finance advice: what works when you have $10,000 won’t work when you have $1 million. 

Yet most financial guidance treats everyone the same, whether you’re scraping together a $1,000 emergency fund or deciding whether to upgrade to business class.

Nick Maggiulli, author of “The Wealth Ladder,” joins us to break down how money strategies must evolve as your net worth grows. He’s mapped out 6 distinct wealth levels, each requiring different approaches to spending, saving and investing.

The levels start simple. 

Level 1 covers anyone with less than $10,000 in net worth — that’s 20 percent of American households. Here, bad luck gets amplified. A flat tire that costs $200 could spiral into job loss and debt if you can’t afford the repair.

Level 2 spans $10,000 to $100,000 in net worth. Maggiulli calls this “grocery freedom” — you can splurge on the nicer eggs without checking your bank balance. 

Level 3, from $100,000 to $1 million, brings “restaurant freedom.” 

Level 4, the $1 million to $10 million range, unlocks “travel freedom.”

Getting beyond Level 4 — into the $10 million-plus territory — requires business ownership or extreme patience. Maggiulli calculates that even saving $100,000 annually after hitting $1 million takes 23 years to reach $10 million, assuming 5 percent annual returns.

The data shows income matters more than frugality, especially in the early levels. The median household income in Level 1 is $32,000, but in Level 4 it’s $197,000, and in Level 6 it reaches $4.3 million.

We discuss why homeownership dominates wealth in Levels 2 and 3, how investment assets become crucial in higher levels, and why many people in Level 4 choose “Coast FIRE” over the grinding path to Level 5.

Resources mentioned:

The Wealth Ladder Book

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I love index funds and ETFs for their low-cost nature and simplicity of ownership. However, if you want to build generational wealth before traditional retirement age, consider looking beyond just index funds and index ETFs.

Since starting Financial Samurai in 2009, I’ve written extensively about investment strategies, financial independence, and retiring earlier to do what you want.

Based on years of reader surveys and conversations, it’s clear this community is one of the wealthiest on the web. A significant portion of you have already surpassed the $1 million net worth mark, while many more are closing in. In comparison, the median household net worth in America is only about $200,000.

With this in mind, it’s time to acknowledge a simple truth: the richest people in the world don’t rely mainly on index funds and ETFs to build their fortunes. Instead, many use index funds primarily to preserve their wealth, not create it.

Why Index Funds Alone Aren’t Enough

Most of us love index funds for their simplicity, low fees, and historical returns. But if your goal is to achieve financial freedom before the traditional retirement age, or to reach a top 1% net worth, index funds alone probably won’t get you there before age 60.

To get rich sooner, you need either:

• A massive amount of income to consistently invest large sums into index funds, or
• To take more calculated risks in other asset classes

Simply put, index fund investing is best for capital preservation and slower, steadier growth. A potential 10% annual return is fantastic. But at that rate, your investment only doubles every 7.2 years. Hey, I’ll take it, and so would many of you. However, it’s simply not good enough for the richest people.

Your life is finite. Most of us only start working full time after age 18. Forty years might sound like a long time to build wealth, but trust me—it flies by. I’m 48 now, and I graduated college in 1999 at age 22. The past 26 years have zoomed past.

If I had only invested in index funds, I wouldn’t have been able to leave the workforce for good in 2012 at age 34. Don’t forget, there was a “lost decade” for both the S&P 500 and NASDAQ from 2000 to 2012. Relying solely on index funds would have delayed my financial freedom indefinitely.

Besides getting lucky, the only way to achieve financial freedom sooner than average is to take above-average risks by investing beyond index funds and ETFs. Looking back, I wish I had taken more risks.

The Average Rich Versus the Richest Rich

First off, if you’re rich—or feel rich—congratulations! You’re ahead of at least 90% of the world, which also means you’ve bought yourself more freedom than most. Although it’s tough, try not to let someone richer than your already-rich self get you down. The key is appreciating what you have.

That said, it’s important to distinguish between two types of rich, because they’re not the same. The personal finance community mostly focuses on the first kind—The Average Rich—partly because it’s easier to explain and attain, and partly because many financial creators don’t have finance backgrounds.

In fact, the lack of financial depth in the space was one of the main reasons I launched Financial Samurai in 2009. Back then, nearly every blogger only emphasized budgeting and saving their way to wealth. That’s solid advice for most people, however, I wanted to go beyond that. You can only do so much saving your way to wealth.

I wanted to escape the finance industry altogether and retire early. That’s when I started writing about FIRE for the modern worker. With the internet making it possible to earn and live in non-traditional ways, I saw an exciting opportunity to pursue a different lifestyle.

Ironically, it was 2009—during the global financial crisis—when the digital nomad trend really took off, as millions found themselves out of traditional jobs and searching for something new.

Now let’s definite the two types of rich people.

1. The Average Rich

This group includes individuals or households with investable assets between $1,000,000 and $5 million. They tend to be highly educated, dual-income professionals who max out their 401(k)s, invest in low-cost index funds, and own their primary residence.

Most of their investments are in public markets and real estate, and they typically feel financially stable but not truly rich. Some would describe this as the mass affluent class. Many started off or are HENRYs (High Earners Not Rich Yet), but then often slow down their pace of wealth accumulation once kids arrive.

You might think of the everyday rich person as someone with grey hair, a portly figure, and retiring around the more traditional age of 60–65. They’ve got a median-priced home and might fly Economy Plus if they are feeling particularly spendy. They aren’t eating at Michelin-star restaurants, except maybe for a rare special occasion, like a 30-year wedding anniversary.

The Average Rich know they’re wealthier than most, yet they still don’t feel rich. Instead, they feel closer to the middle class than to the truly wealthy.

2. The Richest Rich

These are the people with $10 million-plus in investable assets, often owning second and third vacation homes, flying first class, and making high six-figure or seven-figure investments. Their kids mostly go to private grade school, which they can comfortably afford without financial aid. They also freely donate significant sums of money regularly.

Instead of investing mostly in index funds to get rich, their money came from:

They might own index funds, but it wasn’t a driver for them to get rich. Instead, index funds are a place where they park their money, almost like a cash plus, until they find a potentially better opportunity.

20% plus or minus moves in the S&P 500 don’t phase them as the Richest Rich often experience much more volatile swings. In fact, the Richest Rich often have investments go to zero as they continuously fortune hunt for the next multi-bagger investment. So often, index funds and ETFs are a small percentage of their overall net worth (<20%).

The Richest Rich Tend To Be Seen as Eccentric

The Richest Rich are often viewed as eccentric, agitators, or downright weird by the general public. That’s because they tend to reject the status quo and do things their own way. As a result, they attract critics—sometimes lots of them—simply for not following societal norms.

They refuse to spend their entire careers working for someone else to make that person rich or organization rich. They aren’t spending a fortune to get an MBA only to work for someone else. Instead, they bet heavily on themselves through entrepreneurship and alternative investments. Index funds and ETFs? Boring. Too slow. These folks would rather build something from scratch or swing for the fences.

Many of the Richest Rich also go all-in on optimizing their bodies and minds. They train hard, eat clean, and track every metric they can—often in the hopes of staying fit enough to extend their grind and lifespan.

To most, they come across as quirky or intense. But from their perspective, it’s the rest of society that’s asleep, trapped in a system they’ve managed to escape.

Real-World Net Worth Breakdowns

Here are a few anonymized examples of the Richest Rich:

Example 1 – $30 Million Net Worth

• 30% ownership in business equity they started
• 30% real estate
• 20% public equities (65% individual stocks, 35% S&P 500 index funds)
• 15% venture capital funds
• 5% muni, Treasury bonds, cash

Example 2 – $300 Million Net Worth

• 40% ownership in business equity they started
• 20% real estate
• 20% in other private companies
• 15% stocks (half in index funds)
• 5% cash and bonds

Example 3 – $600 Million Net Worth

• 5% ownership in a massive private money management firm as one of their senior execs
• 15% real estate
• 50% in other private companies
• 10% stocks (half in index funds)
• 20% cash & bonds (~$180 million at 4% yields a whopping $6.4 million risk-free a year today)

None of them got rich by only investing in index funds. Instead, index funds are simply a low-risk asset class to them where they can park money.

Net Worth Breakdown By Levels Of Wealth

Here’s a good net worth breakdown visualization by net worth levels. The data is from the Federal Reserve Board Of Consumer Finances, which comes out every three years.

Let’s assume the mass affluent represented in the chart below is at the $1 million net worth level. Roughly 25% of the mass affluent’s net worth is in their primary residence, 15% is in retirement accounts, 10% is in real estate investments, and 12% is in business interests.

In comparison, for the Richest Rich ($10M+), at least 30% of their net worth is in business interests. Intuitively, we know that entrepreneurs dominate the wealthiest people in the world. Therefore, if you want to be truly rich, take more entrepreneurial risks and investment risks.

Time + Greater Risk Than Average = Greater Than Average Wealth

Building meaningful wealth often comes down to how much risk you take—and how early you take it. When you’re young, lean into bigger bets. Invest in yourself. Build something. Own something beyond just index funds. If you lose money, you’ve still got time to earn it back—and then some.

If I could rewind the clock, I would’ve taken more calculated risks in my 20s and early 30s. Rather than playing it relatively safe, I would’ve gone bigger on business opportunities and leveraged more into real estate. I also would’ve made larger, concentrated bets on tech giants like Google, Apple, Tesla, and Netflix. The CEO of Netflix, Reed Hastings, spoke at my MBA graduation ceremony in 2006 when the stock was only $10 a share.

In addition, I would have started Financial Samurai in 2006, when I graduated business school and came up with the idea. Instead, I waited three years until a global financial crisis forced me to stop being lazy.

But honestly, I was too chicken poop to invest more than $25,000 in any one name—even when I had the capital to put $100,000 in each before 2012. The scars from the dot-com bust and the global financial crisis made me hesitant, especially after watching so many wealthier colleagues get crushed.

Still, I still ended up saving over 50% of my income for 13 years and investing 90% of the money in risk assets, most of which was not in index funds. I’ve had some spectacular blowups, but I’ve also had some terrific wins that created a step function up in wealth.

Don’t Be Too Easily Satisfied With What You Have

One of the keys to going from rich to really rich is pushing beyond your financial comfort zone—especially while you’re still young enough to bounce back from mistakes.

You’ve got to be a little greedier than the average person, because let’s face it: nobody needs tens or hundreds of millions—let alone billions—to survive or be happy. But if you’re aiming for that next level of wealth, you’re going to have to want it more and take calculated risks others won’t.

I was satisfied with a $3 million net worth back in 2012, so I stopped trying to maximize my investment returns. Big mistake. The economy boomed for the next 10 years, and I missed out on greater upside.

Then in 2025, after another short-term 20% downturn, I shifted my taxable portfolio closer to a 60/40 asset allocation. The temptation of earning 4%+ risk-free passive income was too strong. From a pure returns perspective, that’ll probably turn out to be another mistake long term.

To balance things out, I’ve deployed a dumbbell strategy—anchoring with Treasury bills and bonds on one end, while taking bolder swings in private AI companies on the other. And you know what? It feels great. I get to sleep well at night knowing I’ve got protection on the downside, while still participating in the upside if the next big thing takes off.

Final Thought On Investing In Index Funds And ETFs

Index funds are great. I own multiple seven figures worth of them. You should too. But they are best suited for those on the traditional retirement track or those looking to preserve wealth.

If you want to achieve financial freedom faster or join the ranks of the Richest Rich, you’ll need to invest beyond index funds. Build something. Take risks. Own more of your future.

That’s how the richest people do it.

Free Financial Analysis Offer From Empower

If you have over $100,000 in investable assets—whether in savings, taxable accounts, 401(k)s, or IRAs—you can get a free financial check-up from an Empower financial professional by signing up here. It’s a no-obligation way to have a seasoned expert, who builds and analyzes portfolios for a living, review your finances. 

A fresh set of eyes could uncover hidden fees, inefficient allocations, or opportunities to optimize—giving you greater clarity and confidence in your financial plan. The richest people in the world get regularly financial checkups.

The statement is provided to you by Financial Samurai (“Promoter”) who has entered into a written referral agreement with Empower Advisory Group, LLC (“EAG”). Click here to learn more.

Diversify Your Retirement Investments

Stocks and bonds are classic staples for retirement investing. However, I also suggest diversifying into real estate—an investment that combines the income stability of bonds with greater upside potential.

Consider Fundrise, a platform that allows you to 100% passively invest in residential and industrial real estate. With over $3 billion in private real estate assets under management, Fundrise focuses on properties in the Sunbelt region, where valuations are lower, and yields tend to be higher. As the Federal Reserve embarks on a multi-year interest rate cut cycle, real estate demand is poised to grow in the coming years.

In addition, you can invest in Fundrise Venture if you want exposure to private AI companies like OpenAI, Anthropic, Anduril, and Databricks. AI is set to revolutionize the labor market, eliminate jobs, and significantly boost productivity. We’re still in the early stages of the AI revolution, and I want to ensure I have enough exposure—not just for myself, but for my children’s future as well.

I’ve personally invested over $400,000 with Fundrise, and they’ve been a trusted partner and long-time sponsor of Financial Samurai. With a $10 investment minimum, diversifying your portfolio has never been easier.

To increase your chances of achieving financial independence, join 60,000+ readers and subscribe to my free Financial Samurai newsletter here. Financial Samurai began in 2009 and is the leading independently-owned personal finance site today. Everything is written based off firsthand experience. 

How to Grow Wealth on a Daily Basis by Being Resourceful

Hey there — I’m Amos, and I’m here to tell you something that might change how you think about wealth:

You don’t need a lot of money to start growing wealth.
What you need is resourcefulness — the mindset that turns what you do have into something more.

In fact, when you get serious about using your daily moments wisely, wealth stops feeling like a distant dream and starts becoming a real, daily rhythm.

Wealth Begins in the Mind

True wealth doesn’t start with a bank account. It starts with how you see the world.

Being resourceful means:

• Seeing opportunity where others see lack
• Asking “What can I do with what I have?” instead of “What don’t I have?”
• Staying curious, disciplined, and adaptable, even when the outcome isn’t guaranteed

Every day gives you a choice: to spend, waste, or grow your time, energy, and attention.

Small, Daily Moves = Massive Long-Term Gains

Here are a few resourceful habits that build wealth quietly, steadily, and powerfully:

• Track everything — Awareness is power. Knowing where your money goes gives you control.
• Automate small savings — Even $1/day becomes $365 in a year (plus interest). It’s the habit, not the amount, that matters.
• Turn knowledge into income — Write, teach, create. Your ideas have value.
• Make one connection a day — Relationships are currency. One new person can open a world of possibilities.
• Build a ‘resource stack’ — List your skills, experiences, contacts, tools. Revisit it weekly to spot what you’re underusing.

Resourcefulness in Action: The Wealth-Maker’s Mindset

Let’s break it down:

• You have a phone – that’s a business tool.
• You have a story – that’s content someone needs to hear.
• You have 10 minutes – that’s time to learn, invest, or reach out.
• You have one connection – that could lead to your next project or sale.

Wealth grows when you stop waiting for better circumstances and start maximizing the ones you already have.

The Bottom Line: Be More With Less

Every wealthy person I’ve studied didn’t start with more money.
They started with more intention.

So if you’re asking, “How resourceful do I have to be to grow wealth daily?”

Here’s the truth:

As resourceful as you are willing to become.

Because daily wealth isn’t just about income — it’s about momentum, mindset, and mastering your minutes.

Keep showing up. Keep building.
And remember — you already have everything you need to start.

Ready to turn your daily habits into lifelong wealth?
Join the Age and Wealth community and get practical tools, inspiring insights, and weekly wisdom to help you grow — financially, personally, and purposefully.

Subscribe now and start building wealth with what you have, right where you are.

We’re halfway through the year, and if you’re like most professionals, you’re probably looking back at the past six months wondering where the time went. So the question here is how to Make Your Second Half of The Year meaningful.

The days blurred together in a whirlwind of meetings, deadlines, and endless to-do lists. You stayed busy, but did you make meaningful progress toward what truly matters?

If this resonates with you, you’re not alone. The mid-year mark presents a unique opportunity to pause, reflect, and realign your efforts for the second half. It’s your chance to transform from being merely busy to being purposefully productive.

The Busyness Trap: Why Activity Doesn’t Equal Achievement

In our always-on culture, we’ve confused motion with progress. We wear our packed schedules like badges of honor, believing that constant activity equals success. But here’s the uncomfortable truth: being busy often masks a lack of clear direction.

Think about the first half of the year. How many hours did you spend in meetings that could have been emails? How often did you tackle urgent tasks while important goals gathered dust? If you’re building wealth and planning for your future, every moment spent on low-impact activities is an opportunity cost you can’t afford.

The difference between busy professionals and successful ones isn’t the number of hours they work—it’s how intentionally they direct their energy toward outcomes that compound over time.

Step 1: Reflect on Your Progress

Take an honest look at the goals you set at the start of the year. Which ones have you achieved, and where have you fallen short? This reflection isn’t about self-criticism—it’s about gathering valuable insights to make better decisions going forward.

Review Your Original Goals.

Pull out those New Year’s resolutions or Q1 objectives you set with such enthusiasm. How many did you actually pursue? More importantly, how many aligned with your long-term vision for wealth building and career growth?

Identify What Helped You Succeed.

Look at the goals where you made real progress. What habits, systems, or mindsets contributed to these wins? If you increased your income, built new professional relationships, or developed valuable skills, what specific actions drove those results?

Recognize What Got in Your Way.

Be equally honest about the obstacles that derailed your progress. Was it a lack of time, unclear priorities, or energy drains that consumed your focus? Understanding these patterns will help you navigate similar challenges in the second half.

Assess Changes in Your Circumstances.

Your life and priorities may have shifted since January. New opportunities, challenges, or insights might have emerged that affect your original goals. Acknowledging these changes is crucial for creating a realistic path forward.

Step 2: Reevaluate Your Priorities

As the year unfolds, your priorities may shift. The goals that seemed crucial in January might no longer align with your current circumstances or the opportunities that have emerged. This step is about aligning your efforts with what matters most to you now.

Ask the Hard Questions: Do your original goals still make sense? Are there new opportunities or challenges to consider? Has your financial situation, career trajectory, or personal circumstances changed in ways that affect your priorities?

Adjust for New Opportunities Perhaps you’ve discovered a promising investment opportunity, received an unexpected job offer, or identified a skill gap that could accelerate your career. Your mid-year reset should account for these new possibilities.

Let Go of What No Longer Serves You. This might be the hardest part: releasing objectives that no longer align with your purpose. That side business idea that lost its appeal, the networking group that doesn’t fit your industry focus, or the certification that won’t actually advance your career—be willing to let them go.

Focus on Wealth-Building Alignment. Every goal you carry forward should connect to your broader financial objectives. If you’re building wealth for retirement, starting a business, or creating generational assets, ensure your priorities serve these bigger pictures.

Step 3: Set Clear, Actionable Steps

With clarity on your updated priorities, it’s time to transform big ambitions into achievable tasks. This step bridges the gap between intention and execution.

Break Down Your Revised Goals: Take each priority and break it into specific, manageable actions. Instead of “increase income,” define exactly how: “secure two new high-value clients by November,” or “complete certification program by October to qualify for promotion.”

Define What Success Looks Like. Be specific about your desired outcomes. What does a 20% income increase actually look like in dollars? How many new professional relationships constitute meaningful network growth? Clear definitions prevent you from moving the goalposts later.

Create Your Action Timeline: Assign realistic deadlines to each step. Work backward from your year-end goals to determine monthly and weekly milestones. This timeline becomes your roadmap for the second half.

Identify Resources and Support: What tools, training, or relationships will you need to achieve these goals? Do you need to invest in new skills, hire support, or build partnerships? Identifying these requirements early prevents surprises that could derail your progress.

Transform Ambitions into Daily Actions. The most important question: What will you do differently tomorrow? Your daily actions should directly connect to your bigger goals. If building wealth is the objective, how does each day move you closer to that outcome?

Step 4: Commit and Track Your Progress

The final step transforms your strategic second half into reality through renewed commitment and consistent monitoring.

Make a Renewed Commitment.

Your updated goals deserve a fresh commitment. This isn’t about perfection—it’s about showing up consistently for what matters most. Write down your commitment and revisit it regularly to maintain accountability.

Establish Your Tracking System.

Choose a monitoring method that fits your style: a journal, an app, regular check-ins with a mentor, or monthly progress reviews. The key is consistency. You can’t manage what you don’t measure, and tracking keeps you honest about your progress.

Schedule Regular Check-Ins:

Build review sessions into your calendar. Weekly reviews help you stay on track, while monthly assessments allow for strategic adjustments. These aren’t bureaucratic exercises—they’re course corrections that keep you moving toward your wealth-building objectives.

Celebrate Your Wins Along the Way.

Acknowledge progress, no matter how small. Completed a challenging certification? Landed a new client? Made a smart investment decision? These wins build momentum and reinforce the behaviors that drive success.

Stay Flexible and Adjust as Needed.

Markets change, opportunities emerge, and circumstances shift. Be flexible enough to adjust your plan while maintaining focus on your core objectives. This adaptability prevents you from rigidly pursuing goals that no longer serve your purpose.

By resetting your goals with intention and structure, you can finish the year strong, focused on what matters most, and empowered to make meaningful progress toward your wealth-building objectives.

When you shift from being busy to being intentional, something remarkable happens. Your efforts begin to compound. The relationships you build strategically open unexpected doors. The skills you develop systematically increase your earning potential. The investments you make thoughtfully grow your wealth.

Your Second Half Starts Now

Resetting your goals at midyear is a powerful way to regain momentum and ensure your efforts align with your current priorities. The past six months are gone, but your next six months are entirely within your control.

You can continue the cycle of busy work that leaves you exhausted but no closer to your wealth-building goals, or you can use this mid-year inflection point to design a second half that truly matters. The choice is yours, but remember: every day you spend being busy instead of being strategic is a day further from the financial future you’re working to create.

What will you choose to make your second half of the year meaningful?

JL Collins doesn’t know what the efficient frontier is. The author of “The Simple Path to Wealth” — the guy synonymous with VTSAX and chill — admits this right off the bat when we challenge him with advanced investing concepts.

Collins joins us for Part 1 of a two-part series where we skip the basics and dive straight into the complex stuff. We grill him on whether his simple approach actually beats more sophisticated strategies, and his answer might surprise you.

He concedes that Paul Merriman’s four-fund portfolio probably outperforms his one-fund approach mathematically. But Collins argues that execution trumps optimization every time. Most people can’t stick with complex strategies for 20 years, especially when those strategies require selling winners to buy losers – something that goes against human nature.

Collins prioritizes what works in real life over what looks good on paper. He calls index funds “self-cleansing” because they automatically rotate out failing companies and sectors while rotating in the new winners. You don’t need to predict which companies will dominate next – you’ll own whatever rises to the top.

The episode covers his thoughts on VTSAX versus VTI, international diversification, and why he’d rather put Tabasco than Cholula on his eggs — his quirky way of explaining personal preferences in nearly identical investment options.

Resources Mentioned
Episode 31, Interview in 2016 with JL Collins

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(0:00) Intro

(1:00) JL admits he doesn’t know the efficient frontier

(2:00) Simple vs optimal but complex paths

(4:30) Paul Merriman’s four-fund portfolio vs VTSAX

(6:00) JL concedes Merriman’s approach is mathematically superior

(7:30) Risk parity investing discussion

(8:30) Sequence of returns risk and retirement bonds

(12:30) JL’s birthday email from Jack Bogle

(15:00) VTSAX vs VTI 

(17:00) Total stock market funds across brokerages

(23:30) Mag 7 concentration risk

(27:00) Sears story and self-cleansing index funds

(30:30) International diversification and US dominance

(39:00) World funds versus separate international

(45:00) When to shift to world fund

(47:30) Bond allocation timing strategies

(48:30) Target date funds 

(50:30) One-fund vs two-fund approach

(52:00) Historical diversification and Nifty 50

 

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