September 2026 Mailbag: 16 Years Old to 25 Years Foolish

In this episode of Motley Fool Rule Breaker Investing, Motley Fool co-founder David Gardner reads and answers mailbag questions.

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A full transcript is below.

This podcast was recorded on Sept. 30, 2026.

David Gardner: It's mailbag time, and this month, our correspondence range from 16-years-old to 25 years Foolish. A young German reader is already thinking about something many of us don't think about until much later in life, time, freedom. Another listener asks whether in a world changing faster and faster, indexing might make more sense now than ever. We'll hear from a self-directed investor who's underperformed the account he wasn't managing, and he has no regrets. Later, one of the tougher questions any investor can ask, how do you know whether your losers simply need more time or you just didn't pick enough winners? Seven correspondent, seven stories and questions from across our Foolish universe. Your September 2026 Mailbag, only on this week's Rule Breaker Investing.

Welcome back to Rule Breaker Investing. This is the fourth consecutive week that Bart and I are doing and producing this podcast After Hours. I've mentioned this once or twice, I'm not going to complain about it, but I have grand jury duty here in Washington, DC, which is a five week. That's right. Five days a week, 9-5, five-week commitment. It's something quite remarkable. I'm not asking for praise for anybody. I want to give a shout-out to my 22 other grand jurors because everybody's got their own backstory. I will say this about jury duty. Obviously, almost everybody roots against it. A lot of people who've seen the Amazon Prime Video jury duty think it's funny. I do, too. Those are a couple thoughts about jury duty.

It's also inspiring to know that this is how our system works. In the case of grand juries, we have a different mission than typical jury duty. Those of you who are jurist prudentially inclined will already know this. I didn't, though. Grand juries don't sit on cases. You don't all have to agree and say guilty or innocent over a few days. Grand juries are only passing through possible cases, saying, yes, there is enough evidence, or no, there's not in order to create trials that other juries will sit on. Over the course, it's been four weeks for me now, I have participated in 46 separate cases with my fellow grand jurors voting in which ones we think should one day be a trial? They're all felonies. It's all the hardest, worst things that you'd want to see in your city or any other. It's been a really interesting few weeks. I look forward to doing this podcast again at normal hours come October.

I do want to give a shout out to a new listener, Patricia, because, Patricia, you are a new friend of mine. We met at jury duty, and you said you were going to listen to podcast this week. Thank you for listening in, and thank you as always, to every new Fool who joins this podcast, Rule Breaker Investing in any given week, and especially thank you to those who turn their friends onto it, who make an effort to let other people know about the beauty of investing, of breaking the rules, of being positive going through life, how to win the games of investing and business and life. That's what I'm trying to help us all do and you help me, too, back with every monthly mailbag. Yes, Patricia and every other new listener, you have happened upon what happens at the end of every month for this podcast, which is that I take in mail. Most of the time it is email. Our email address is rbi@fool.com.

We invite all commerce; drop me a line. If you have feelings or thoughts about podcasts we did over the course of the month. I'll be going over the September one shortly. But you're also welcome to drop questions, thoughts about investing. We sometimes have poems and other delights. We don't have it this week, but we have audio mailbags so if you'd like to drop an audio file, you can just paste that in to an email rbi@fool.com. We have seven mailbag items this month. It's been a very full month. Let's look briefly back at the month that was. This is the fifth Wednesday. Therefore, we've had four podcasts. The first was on September 2nd, old, new, borrowed and blue volume 11, as September hodgepodge, spanning a world series lesson for investors, an old Investing Truth in exactly 350 words, Kevin Kelly's invitation to live your most improbable life. Yes, blueberries.

On September 9th, it was 10 years later, five low risk stocks for the next year. Rick Munarriz joined me, and we reopened the only five stock sampler ever designed on this podcast for just one year. We discovered with the 10 years later series what another nine years can teach us about risk, resilience, and letting winners run. September 16th, I brought back Volume 4 of one of my favorite recent series ChatGPT Asks and David answers. ChatGPT returned to the pitcher's mound with five provocative questions designed to challenge my assumptions. Maybe expose a blind spot or two and send my answers somewhere sometimes that neither of us would quite have expected. ChatGPT asks and David answers Volume 4.

Then finally, last week it was our quarterly game show the Market Cap Game Show. We entitled it What's Rare Earth Worth? Mac Greer and Yasser El-Shimy joined me for our quarterly Game Show with you playing along last week as well. How'd you do? By the way, if you missed the opportunity, you can still listen back in and play. The market caps haven't changed that much. Ten fresh companies, two throwdowns and a market cap journey from Zoom meetings and sleep apnea to rare earths and 78,000 miles of pipelines. That rounds out the fourth of our September podcasts so far. That was the month that was.

Before we get started with our seven mailbag items, a few hot takes from Twitter. The first one I want to call out at ProShop Guy MF1. Mike, you wrote, while I scored eight points and actually beat the contestants, it is not apples to apples as a comparison. You go on, as a contestant, I would have to set the range myself, as opposed to just taking a position on each of the companies. As a result, my performance would vary in person. Well, this is true. Mike, you're pointing out that when you play along with the Market Cap Game Show at home, you never yourself have to set any of the ranges. Of course, my contestants do have to do that. But then again, they're professionals. The rest of us are amateurs, me included versus playing along at home, and I think it's easier to play the game that way. But you're right, Mike. It probably does pump up your score a little bit. Yet, I'm still going to say eight is pretty doggone good. Thank you for that.

Another tweet. This one from @307Fool my friend Matt Hard. Matt wrote, I have a fun addition to my final Thursday purchases of September. I should pause it there. Matt has a thing that he's done on Twitter for years now. Every Thursday, he buys some more stocks because he's regularly saving from his salary and investing. Every Thursday, whatever the market's doing, he's got another stock or two or three to buy, and he always posts them on Twitter. This month, for the first time, he did his first five-stock sampler. He said, just like on at RBI podcast, by the way, that is this podcast Twitter handle. I'm also at David G. Fool, but he's calling out at RBI podcast. Matt goes on, I will have groups of public purchases that I will track against a purchase of the Vanguard Index Fund on the same day. Month 1 is going to be my five biggest overall winners by percentage. I will reveal one per day. Company number one, Matt concluded, is my largest winner: Nvidia. That is a company that keeps coming back and will again later in this podcast. Matt also conducted a giveaway last week a few copies of Rule Breaker Investing my book, which he generously had simply purchased on his own and then gave away to respondents to a few of his threads on Twitter X.

Also shout out to Andrew Gibson for throwing in a copy of his own. Now, why did Matt do that? I think it's because it's the first birthday for Rule Breaker Investing. My book came out a year ago this month, and Matt, thank you very much for the celebration. I had so much fun writing the book, and it's been so much fun hearing from those of you who have read and enjoyed and learned from it and passed it on over this first year. I'm playing the long game in all things in life so I look forward to keeping that current and selling for a long time. I hope whoever you are, I hope your kids one day get to read Rule Breaker Investing. I should mention, by the way, that there was a wonderful review of the book put up on Twitter/X by Yavuz Macun, Y-Y-M-A-C-U-N on Twitter. Yavuz, thank you very much for taking the time to write a really nice review of Rule Breaker Investing on its first birthday. With all that said, let's get started.

It's your Mailbag Item Number 1. This one comes from David Reisinger. David is writing from Rottenburg Om Neckar in Germany. Dear David, I'm a 16-year-old guy from Germany. David writes, and I just wanted to send you a short message to thank you for your book, Rule Breaker Investing. My dad actually gave it to me. To be honest, I usually hate reading and almost never read books. David, I'm not sure how you get away with that going through school, but I think you mean outside reading. I can also understand that because if you have enough assigned reading, sometimes it's not that much fun to spend our time outside of school doing even more reading. You go on to say, I usually hate reading and almost never read books but yours was totally different. Through your book, I really discovered reading for the first time, and I suddenly realize how much cool stuff you can learn from books. Now I'm going to pause it right there, full stop because, wow, David, thank you. That line alone is like a mailbag mic drop moment. You really discovered reading for the first time and suddenly realized how much cool stuff is out there.

Wow. Thank you so much. I'm going to say, maybe listen back on this podcast to last month because every August, I welcome in authors of books I've read and admired, and I had three more great ones last month. You're probably in school right now, so you may not have time for extra outside reading, but you might really enjoy one or more of my authors in August interviews this year. Anyway, let me go back to your note. It goes on, I'm already investing a bit together with my dad, and I'm currently participating in the stock market game Trader 2026, hosted by Societe Generale. I loved your book, especially the story where you met Jeff Bezos. For me, the big takeaway was that you have to be optimistic and just dare to do things because if you never try David writes, the chance of failing basically 100%. You've probably heard this line before, David, but I'll just chip in here. You miss 100% of the shots you never take. I totally agree. I think we should be trying to put points on the board, a lot of the time in life. There is time for pause and for reflection, but more than anything, I think life is to be lived, and taking those shots is a great way to go through life. Sometimes I'm going to add in a line I read the other day. Closed mouths don't get fed. It makes the same point about you miss 100% of the shots you never take, except it's specifically about speaking up. Taking the time to speak up, even when sometimes it's uncomfortable or by nature, you're shy, there are lots of situations I think I can look back on my life and wish I'd said something. I'm going to put it out there again. Closed mouths don't get fed.

et me go back to your note. You write, "As I'm growing up, I've realized that time is the most valuable thing in life. Even though I'm fortunate to grow up in a great family, I see how much my dad works. Looking ahead, my biggest goal for my future self is time freedom, especially when I have kids of my own one day. I want to build a life where I'm not stuck working all day but actually have time for family, freedom, and the things that matter. I'm going to pause it right there once again, David, because I find myself wanting to comment throughout your wonderful note, and I'm going to do it again here. I'm going to say, here's the thing, though, for many adults. Our work deeply matters. I don't think you intended this, but I'm still going to speak to it. Just because I work or your dad works or some of us work a lot doesn't mean that that time is misspent. Time freedom is great, but in the end, you're going to spend all your time. You already get this on something and you want that to matter.

My own math, sometimes I think about life this way. This is simple multiplication I have for you. But I've sometimes thought a life well lived equals first fulfilling and satisfying yourself, multiplied by fulfilling and satisfying others. If you can take those two factors, make them as big as possible and multiply them, making sure that you're happy and that you're putting on your oxygen mask before you start trying to help others in some contexts and realizing that so much of our happiness comes from creating more happiness for others. When you multiply those things together, I think you're in a really good place with a life well lived. Some of that, is work, and I'm not looking to avoid work. This podcast is work for me. I love doing it, and I don't have any regret that I'm spending some of the time I could have had free talking to you right now. I guess it's worth saying in conclusion on this one, yes, we want to free up our time. We're going to spend that time, one minute, one hour, one day after another, and we want that to count.

There's a book called Moonwalking with Einstein that I totally recommend to you. It's all about human memory and how to improve your memory and how memory works, and just a lot of thoughts historically about the importance of memory. One of the points the author, Joshua Foer makes, and by the way, I totally recommend this book to you. I think you'll love this book. I think anybody listening who hasn't read Moonwalking with Einstein is going to love that book. But the richest life, he contends, is the one that you lead with a lot of variety, variety being the spice of life. We're going to have a much better memory and feel like we had richer, longer lives if we have a lot of different experiences. By contrast, if you're doing the same thing every day, day after day, even if it's satisfying, a lot of people who get older near the end of their lives start regretting that they just kept doing the same thing over and over because it made their life feel like it went by so fast. I think enriching your life through a wide variety of experiences is just as important, if not even more important than merely having free time.

Let me close out with how you closed your note out, David. You said, "Since I want to start taking the right steps early while I'm still 16, what action steps or mindset shifts would you recommend to a 16-year-old to build true time freedom for the future? What do you think is most important to focus on at my age? Are there any other books you think I should read next? My English isn't perfect, but I would be super happy if you find a minute to reply. Best wishes, David Reisinger," again from Rottenburg am Neckar in Germany. Well, I loved your note, David. It was my delight to lead off this mailbag with it this month. I feel like I've already said a lot, but I'll just give a few quick answers to your important questions at the end. You asked what action steps or mindset shifts would help a 16-year-old to build true time freedom for the future. I think you already know how I'm going to answer this. I'm going to say investing, because truly, at your age, and I love that your father's gotten you started investing.

Thank you, Vater, for great taste in investing literature and for making recommendations. I love, David, that you're already investing some. You're in an investment contest. You're doing it with your dad. Those are the important things, but that investing compounds over time, and you're going to find yourself with a lot of extra time, potentially free time, because you created financial freedom for yourself because you got started investing early. You already know this. You've read my book, but that is my number one answer to anybody who asks, how do I find more free time in the future? You also asked, what do I think is important to focus on at your age? I would say spending time with the best people you can find, whether we're talking about peers of yours. Who are the most admirable people who are in your classroom or among your friend group? If you run out of people or friends, you just found out something else that's admirable to spend time with, and that's books. Spending time with the best people and the best books that you can, I think, is a very worthy thing to focus on at the age of 16.

I would also say growing your friend group, because growing your friend group also will grow the variety of experiences that you have, and I already spoke to the importance, I think, of the variety of experiences that we can garner over the course of our early lives. It's so valuable over the course of your whole life to have lots of different friends and experiences. I was talking to a young grad the other night, somebody who's going to be coming out of college, trying to decide what should be her first job, and good news for her, she has a few different offers. I think my advice back to her, I'm going to give to you as well, which is that when I'm thinking about that first job that I would take, in addition to the salary, which will always matter, I'd also be thinking to pick the one that gives me the widest range of experiences of the job offers at hand. Which one is going to give you the widest range of experiences? Narrow jobs lead to narrow minds.

You asked about book recommendations. I'll close with these two, Atomic Habits and Getting Things Done. Both of them are non-fiction. Really important, develop your mindset around how to lead a great life. Atomic Habits, building good habits, getting rid of bad ones, and how to do those things. James Clear is a fantastic author. This is a mega-seller in the United States of America. I bet you can find a German copy. Getting Things Done, which is all about being organized and organizing your time and being productive by David Allen. I'm happy to say both James Clear and David Allen have been on Rule Breaker Investing, have been on this podcast. I admire their work, and they admired ours enough to join in with us, and you could listen to those podcasts as well, David, if you don't have time to read. There, I hope, is not too long, but a very full answer to a very promising young man. Thank you for reaching out, David Reisinger.

On to Mailbag Item No. 2, this one from Frank writing in, "Hi, David. I really enjoyed the pod where ChatGPT asked the questions. You gave the answers. Your answer to one of those struck me, the one where you said, you may have to pay attention more than you used to, and he's speaking about stocks and the market, based on the speed at which technologies are changing, and that that can be a bit stressful. Frank goes on, I know you're more or less an anti-Buffett on many investment themes a lot. I know you agree with as well, like being long-term and holding through thick and thin. One comment that came from Charlie Munger years ago struck me the same way as your answer. He said that business is like biology in that "everything dies." He recalled some companies like Kodak as one that just disappeared. Netflix basically caused whole industries to change, and some of them left way behind. There is a question here.

Would it make sense, Frank goes on, now more than ever, to tilt one's portfolio even more toward indexing? The index has a self-cleansing mechanism built in so that when one company rises, it automatically becomes an ever larger percentage of one's portfolio, like Nvidia, for example. For folks that are predominantly indexers, they have participated right along with the rise of Nvidia and other big winners. When something gets competed away and loses out to new technologies, it automatically shrinks. I know you believe the index fund is a great tool for investors, concludes Frank, who don't want to pick stocks. Could it be that this may be the way of the future even more? Thanks. Signed, Frank. Well, Frank, first of all, you know from our first book and the earliest days of The Motley Fool, we have championed indexing.

Back then, we were pointing out that index funds were so much better than managed mutual funds, which were all the rage back in the 1990s when The Motley Fool launched. That was a really important message we put out there, and we've always been big Jack Bogle fans. He became a friend of ours. Such an admirable man. Wish Jack were still with us. But he is through the company that he created, one of the world's largest asset managers, Vanguard. Of course, Vanguard has now been copied by many, as many people, many of our fellow humans are indeed indexing, which means basically take your money and instead of picking individual stocks, just buy all the stocks through the magic of an index fund. A single decision, you could just buy the whole market and enjoy, sometimes not enjoy the market's returns without really spending much time or money at all. These are very cheap ways to invest, very cheap expenses, and that's why they've been such a devastatingly great development for investors worldwide. So much better than many of the overpriced mutual funds that Vanguard has now put out of business. Yeah, you bet we're big fans of indexing. But you also know, Frank, because you and I have been friends and correspondents for many years here, you also know that I love choosing stocks and so much of, I think, the juice in life, not just in your portfolio, but that too comes from being an actor, being a chooser, choosing your own adventure, picking stocks. Doesn't have to be with your whole portfolio. We're going to get into that in a little while.

But yeah, I think the act of choosing is inherently valuable on its own. In some ways, we could almost draw the opposite conclusion from the premise you just put forward. Yes, I do think technological change is accelerating, and I realized on my ChatGPT Asks podcast, at one point, I talked about how that can make picking stocks potentially more difficult. If the world keeps changing faster with new technologies, it can be stressful, and can you and I keep up? But I'd also like to point out that that very change can create the very mispricings and extraordinary companies as well that a Rule Breaker investor hopes to recognize early and often as well. I find myself neutral in terms of whether I favor index funds more than stocks or not. You already know I'm all out stocks. Indexing is almost no part of my financial life, and I have done so much better than index funds, and I think I've met many Motley Fool members who, playing the long game, have done so much better than index funds because they did pick individual stocks.

I'll conclude before we move on to Item Number 3 by talking briefly about the age of big dumb money. This is not a passage or a page that I put in my book, Rule Breaker Investing. It is a point I've made on this podcast before, and because at some point I probably will write another book, not another stock market book. I'm finished with stock market books, but that doesn't preclude an investing book and everything that that word means to me. In some future investing book, I'll probably speak to this because I didn't in Rule Breaker Investing. But the more people index, the more big dumb money is in the system just sloshing around, buying everything, not discerning which are the good companies and which are the bad ones, simply buying everything, buying all the best companies in every industry and all the worst companies in every industry. Therefore, the more and more people who are persuaded to index, the easier it gets to beat the market as a stock pickers. Sometimes I get frustrated when people completely write off Motley Fool services or say it would never be worth buying individual stocks, that would just be gambling.

Silly talk. It would only ever be luck to beat the market averages. I, of course, have been fighting that fight for 35 years and counting, and in my own little way and in my own little world, I'm certainly winning. But the larger world seems increasingly to love indexing, and if it does, then you and I and fellow Rule Breakers, our job becomes easier because everyone else is asleep at the wheel, just mailing in their savings with the gentleman C every two weeks as they just buy everything, not all the best things. I personally think it becomes easier to beat the market the more people lean into index only in their financial lives.

Let's move on to our third mailbag item. This one comes from Andrew Gibson, andygibs53446 on Twitter, X, a familiar correspondent. Andy, you sent me a wonderfully overflowing note this month. Movies, miracles, investing, board games, Yoda, even red oak trees, all in a single mailbag item. You basically supplied me enough material for about three future whole mailbags, but with eight different points to make this week, I'm going to pull just one thread from your tapestry here, the one I found most interesting, we're going to run with that. First, just let me say thank you for a great note, Andy. You led off with it. I'm going to share this with a dad joke that you created with the help of Grok, which is Elon Musk's answer to AI. You used Grok to develop this PG-rated, you say, dad investing joke and here it is. You wrote, My friend bought a stock to hold forever, yet still refreshes ‘every 12 minutes.’ I think some of us can smile askance. I think I'm a bit guilty of that from time to time myself.

Anyway, Andy continues, David, do you believe in miracles? I've been watching Miracle on Ice, the movie, a lot lately for inspiration. I also just finished another movie, Eddie the Eagle, because of the mention the film got in your past episode with author Dave Ulrich in August. Andy says, I'd highly recommend Eddie the Eagle as well. A very fun underdog movie. Both of those movies are about people who had no business being on that stage, and then stayed in the game long enough for something improbable to compound. Andy goes on, that underdog to compounding arc is what I'm really after. I love the ironies and exceptions in Rule Breaker Investing and just your Foolish approach to life in general, the way your thinking never accepts certainty and stays open to being surprised by how a company's destiny can evolve.

Would you share a time in your career when the miracle started for some of your favorite Rule Breakers or maybe at your own company, The Motley Fool? When the inflection point began to show up, and the breakthroughs began compounding, were there moments that made you sit back in your chair in disbelief at a company's success? What was your emotional reaction as it happened? How did you keep your nerves calm when the obvious move for a lot of people is to lock in the win, aka sell? I'm going to leave it right there, Andy. I love the question. My first thought is miracles look sudden in movies, but compounding looks boring in real time. Amazon never sent me a memo saying, Hey, the miracle's now begun. Nvidia never announced, Congratulations, shareholders. You are presently aboard a future 100-bagger. Now, what you actually experience as an investor is quarterly reports, new products, competitors, sometimes some scary headlines, some huge drops.

As you also pointed to, Andrew, some wonderful surprises, too. If you're fortunate, you're going to experience year after year of accumulating evidence that the company you own is becoming something much larger than you originally imagined. It doesn't happen every time, but specifically with Rule Breakers, with the six traits we as Rule Breaker investors look for, you are setting yourself up to be surprised with those discoveries time and time again, and that will contend generation after generation. That's why I think the miracle metaphor deserves a little Rule Breaker tweaking, because our job isn't to predict miracles. I don't think I'd be very good at that. It's to recognize excellence, to buy it, to watch it and then try very hard not to interrupt it.

In his longer note, Andy reminded me of a story he'd shared previously about his friend Blake, who bought a stock at 25 and then watched it run to 70, and he wanted to sell. Andy writes, "I had to remind him, Blake, we're investors, not traders, like David would say, but do what you need to in order to sleep well." That's what Andy told his friend Blake. He goes on today, he thanks me for encouraging him to let that winner run. Still, that fear that what goes up must come down is real. The risk of giving it back is a feeling, not just a footnote. I'll leave it right there. Well said again, Andrew Gibson. Here's the mental move that I try to make when one of my stocks has done something wonderful. I don't ask, has this stock gone up too much? Because I think most people do that in that situation. I try to ask things like, has this company done anything wrong? Because a stock that goes from 25-70 is not itself evidence that something has gone wrong. In fact, quite the opposite can often be true. The market is increasingly recognizing what that company is becoming. It's bidding up its price.

Now, sometimes the story really does deteriorate. Obviously, we all know Peloton how that can happen from time to time. Businesses change, competitors arrive, or the world changes. Sometimes management stumbles, too. That's why it's helpful to pay attention, and I would say, don't manufacture a sell signal simply in the face of your own success. Andy, I'll leave your wonderful word miracle in place there, but with one Rule Breaker thought attached to it. Here I'm going to go for a notable quotable. I'm trying. Here it is. The miracle isn't that you found it. The miracle is that after you found it, you managed not to sell it. Fool on, Andy.

Let's move on to mailbag item number 4. This one comes from Foolish Leprechaun. Hey, David, let me start by saying, I was bummed. I could not make the logistics work around a trip to Ireland to see you all at this year's Investicon. I'm glad to hear that you found it to be a good trip, and it was indeed a fine trip. Thank you, Foolish Leprechaun. You go on. To provide some framework for my subject, I started personal investing later in life, June of 2020, to be exact. When many saw the market was down and thought it was a good time to get in. Although I was already in, because I had a brokerage account that was created from a combination of an old 401(k) that I had that was merged with an outgoing 401(k). I used this new account as a springboard to open an IRA and transfer funds into it for some personal stock investing. You go on. My first transfer was $10,000, and the stocks I bought were all based on a simple principle: find good companies beaten down and take the chance that they will rebound. Plus, some other home run-type chances that I was taking as well. The good companies included Harley-Davidson, Starbucks, and Delta Airlines. The home run swings that I still hold today were Jumia, LifeMD, and PowerPlug.

Foolish Leprechaun goes on. Three months later, I realized I put the cart before the horse and wanted to become educated. I joined a stock market site that provided a lot of metrics and information that I had to figure out on my own. They started a weekly podcast, which I loved, but when they took it away, I needed to find a replacement. That's how we, Foolish Leprechaun writes me, became friends, smiley. I'm glad you've been listening ever since. You go on. As my confidence grew over time, I continued to add from the managed account into my personal account to fund the stocks that I wanted to buy. I've now moved about 25% of the funds in my account, and after six years, my portfolio shows up 31%. My managed account shows up 105%. With that context, it's impossible to know how much I've given up in monetary gains by not leaving everything in the managed account. However, if I did, I would not have enjoyed the experience and education that I've received by creating my own personal account. I believe the financial impact of all this will actually be more toward what we leave our children than it will be for my wife and me as we near retirement. I wanted to get your take on this for others who may have thought or not thought about this investing approach. Thank you, and all the best, Foolish Leprechaun.

It's always disappointing to look up at the scoreboard and see that we're losing. We could have had a higher score had we been indexing. I don't want to be redundant with what I spoke to some minutes ago around indexing. But I will add in a few new thoughts. The first is that I like the architecture that you have built up around you. I like this idea of 25% of your money in stocks of your own choice, and 75% sitting in a managed account. It might be indexed; it might be managed. If it's managed, I hope it's managed well. Foolish Leprechaun, I actually think it's taken a while here, but you've gotten yourself to a good mix.

Now, if you didn't enjoy investing, if you didn't feel any benefit to studying the markets or following technologies or taking a shine to certain companies that express for you what you want our future to be, then I would say, you could probably go back and just index all of it. You don't need that 25%, 75% architecture. But I also regularly counsel friends and family members, if they don't want to go all in stocks or all in indexing, you can have a balance of both. What the numbers are is individual for each of us. You're right now 25% stocks, 75% managed funds. That might be the right number for you. What I often tell friends is, see how you're doing. If you find that you're winning with your stocks, start bumping up that 25% and bumping down to managed. Start to move some money toward what's working, what you love, where your energy comes from.

If, on the other hand, you find that your managed funds are consistently beating your own investing, and there are lots of reasons that could be, some people are even picking good stocks. They don't have the fortitude, the emotional staying power to stay with their own convictions. Sometimes it's not a problem of stock picking; it's a problem of the habits that we've built up as investors. Sometimes we're trading more than investing, or maybe you're not picking the right companies. If that's the case, I'd be the first to say you could start siphoning off some of that money from your stock portion of your portfolio back into the managed or indexed portion. I think that game of having two buckets and then having your money move one way or the other based on what's really working, not over any short-term period, but over the long term. It's not always just about the performance either, because a lot of it is about your own emotions, your own energy. I've already spoken to this, your passion, how you want to spend your life. We should all be trying to live our best life, and for some of us, that really does mean a very rich life of stock picking. It has for me.

But for others, it means they don't want to spend much of their time stock picking. They have a lot of other interests in life, besides. Now that we're in the fourth decade of The Motley Fool, I've met so many different types of people worldwide. I would never simply advocate one approach to how you should manage that portfolio. In fact, for those who have read my book, you'll know there are six principles that I believe each of us should have in managing our portfolios, also six habits that I think we should exhibit as Rule Breaker investors. Then one quick final note here, Foolish Leprechaun. You mentioned the legacy. You mentioned how what you're investing is really more for your kids than for you and your wife. It sounds as if you guys are pretty well taken care of. If that's true, congratulations. If much of the money is ultimately going to go to your children, I guess I'd just say I'd want them to inherit more than the securities, the investments, the stocks themselves. I'd want them to be able to answer questions like, why did Dad own these? What are some of the things Dad learned? What mistakes did he make? What did he believe about business and about the future? I think arming our kids not just with the stock portfolio, but with the wisdom and knowledge and background and context to explain how it all came about, why it mattered to you, and what you were truly giving them. A portfolio accompanied by stories and principles, I guess, is what I'm trying to say is a far richer inheritance than an unexplained statement from a brokerage account. I don't think you're going to make that mistake, but I want to double underline what we're really talking about sometimes, Foolish Leprechaun, when we're talking about legacy.

On to Rule Breaker Mailbag item number 5 of 7. This one from Brendan. Hi, David. I've been listening to Rule Breaker Investing. Really like the way you approach investing, particularly the focus on innovative and disruptive companies, rather than just following the conventional playbook. I'm Brendan, founder of Musa Audio. We're an audio production company specializing in podcasts and audiobooks, handling editing, mixing, and mastering for creators and businesses. Now, I know The Motley Fool has a substantial production operation around its shows, so I'm not sure who looks after Rule Breaker Investing. Specifically, I wanted to reach out and see whether you handle production in-house or work with an external audio team. If you ever need additional production capacity or someone to take on audio projects, we'd be very happy to help. Best, Brendan.

I easily could have not included this on the Mailbag, but it gives me an opportunity, instead, Brendan, to say, first of all, thank you. I'm delighted to report that Rule Breaker Investing has an audio production company. His name is Bart Shannon. Some podcasts require an executive producer, a producer, two associate producers, an engineer, somebody in charge of craft services. The credits can take 30 seconds to read. Hey, with Tiny Tim, God bless us, everyone. Anyway, around here, I have Bart. Somehow, week after week, Bart is enough. Thank you, Bart. Thank you, Brendan. I often say for our mailbags that I saved the best for last. That generally means if we're going to do seven mailbag items, that would be number 7. Indeed, I love number 7 this month, and I'm excited to share that with you. I also love number 6.

Now, they're very different because number 7 inspires us with somebody who's been playing the long game from a modest place and has done wonderfully well. It's one of those inspiring stories that I personally can never get enough of sharing out. I love it. I'm also willing to take on the tough questions, the people who didn't necessarily get it right. I shared one. Foolish Leprechaun has found he's underperforming with his stocks, and he could have left it in the managed portion of his portfolio. I'm always taking all comers, and I learned that specifically during my years hosting the Motley Fool Radio Show on NPR. National Public Radio has some really high standards, and one of them is: you take the letters as they come, all the good ones, and all the bad ones. I'm going to say I've saved the best for last because I think it's important to speak to both situations. Both of these, I hope, are illustrative, and we'll show them, you and me, all off at our best at our whole, our rounded best.

Rule Breaker Mailbag item number 6. Hi, David, I'm writing with a follow-up to two of our previous Mailbag conversations. Kevin McMahon writes, I subscribe to the Motley Fool Everlasting Portfolio 2021 on July 14th, 2021, and invested heavily in its recommendations. As of Sept. 7, 2026, that's when Kevin wrote this note, the portfolio is down 11.58% since inception, while the S&P 500 is up 89.50%. My full portfolio's membership expires Oct. 20, and I'm unsure whether to renew. I love The Motley Fool, but this experience has been difficult to stomach. I appreciated your April 2025 response, acknowledging that your July 2021 picks had struggled, too, and that they may simply need more time.

That brings me to something else you told me. In July 2025, I wrote in about owning 300-plus stocks, and you said broad diversification is one of the surest paths to financial freedom. It reminded me of Chapter 6 from Morgan Housel's book, The Psychology of Money. Chapter 6, Tales You Win. Housel tells the story of an art dealer who accumulated a huge collection, knowing that most pieces would prove unremarkable, while a small handful of masterpieces could become so valuable that they would drive the returns of the entire collection. Given enough time, the collection increasingly reflected its greatest winners. Kevin goes on. That seems very rule breakery. A stock can lose only 100% while a great winner can return 10x, 50x, 100x or more. Could you expand on how time and diversification allow our biggest winners to increasingly drive our portfolio returns, and how do we distinguish between a portfolio whose winners simply need more time and one that after five years just didn't pick enough? Great winners. I'm wrestling with that distinction as I decide what to do next. Thank you, as always, for suffering this fool gladly. Fool on, Kevin McMahon.

Well, Kevin, several foolish thoughts back for you. First of all, thank you so much for taking the time to write. Thank you for being a member of The Motley Fool, and I'm really sorry to hear that your own experience picking some of the stocks in some of our services has led you to be at a loss after six years when the market is quite a bit higher than that. I'm really sorry to hear that, and I understand your question. Are there enough good stocks in there? I don't know what the stocks are, by the way, and I didn't pick the stock, so I can't really speak to that part of it. Or should you maybe consider cutting bait and just going a new direction, or maybe returning to a previous direction? I do want to say a few more things, though. I do want to say that starting in 2021 was a hard time to start investing.

On this podcast, as I did 52 podcasts, the year of 2022 is I've done 52 podcasts going back to 2015. I well remember how hard it was talking about the stock market in 2022. I personally watched my portfolio get cut in half in just that one year of 2022, and a lot of those stocks haven't come back. Some have, but a lot haven't. I just wanted you to know if you followed my 5-stock samplers, here starting in the year 2021. Actually, if you go back to the final seven samplers I picked, starting with the COVID spring of 2020, those seven 5-stock samplers, only two have beaten the market, and the five that have lost have underperformed the market by 60-100 percentage points each. That's my way of saying if you lock yourself into a specific time and you make investing all about a certain month and a certain year, and you buy everything then, and you don't make any changes, most of all, if you don't keep adding to it, then you do put yourself in a vulnerable place where if it was just a bad market environment, if you'd started in 2007, for example, or in 1999, you just wouldn't have felt great six years later about your investing and your investments, and some of those companies don't come back. Some don't become big winners if you lock yourself into a single place and time.

The good news, by the way, for all 30 of my samplers were whomping the market overall, despite periods of extreme underperformance. I'd also say the same thing, by the way, about our Motley Fool services that I've worked on Motley Fool Stock Advisor, Motley Fool Rule Breakers. If you are just consistently investing not in one year, but through all years, all month, through all markets, I think you're going to have a much happier story. I'm pretty sure you already know this. But because your note just mentioned primarily how you put a lot in the market in a certain month, in a certain year, I sure do hope you know that I think it's so important to be constantly saving and adding abundantly growing a portfolio over time.

Before we move on to our final mailbag item this month, one or two more thoughts. Kevin, even if you don't do much better than the market averages, I was hinting at this a bit earlier, but I want to be more explicit about it now. Even as an investor, if you're picking stocks and you're not even doing better than the market averages, as I've often said, the act of striving, of trying, of caring, of choosing, of following, and of learning as you craft your own portfolio is very much its own reward. It has rewards that go well beyond just your investment returns. I'll give you three examples of the advantages that come to self-directed investors. None of these three has anything to do with your actual market returns, but all of them are, for me, very real. I hope for you, too. I would say, first example, you deepen relationships because investing gives you something substantive that you can explore with a spouse, with a child, with a parent. We've already had a story or two that way this month. With a friend, with an investment club. If you choose your own stocks and if you develop your own view of things, you become more interesting to other people around you. You become a resource to friends and family because you’re actually paying attention to the game, and you’re learning as you go, and you’re sharing that out into what I hope will become a decades-long shared pursuit.

Example No. 1: you deepen relationships. Example No. 2: I’ve felt this many times as an investor, over the course of my 40-plus adult years, you discover better products. When you're following companies, following stocks, it might lead you to the car that you end up loving, or the software that saves you hours every week or the medical technology you tell a friend about when they need it. How many stories have I heard through, well, mailbags on this podcast or through Fool Fests? We have one coming up shortly in October, a gathering of many of our longtime members here in Washington, DC. How many conversations have I had at happy hours or over coffees with people, who because they were researching the stock, knew about this product that enriched their lives or somebody else's? If you're just indexing and you're just mailing it in and not paying too much attention, you're much more likely to miss some amazing products and services that you could have found out about, that could have made for you a better life. By the way, obviously, as a stock market investor, you can become part owners of those companies as well.

Then example, number 3, you create opportunities. Again, this is also very real for me, and I've seen it many times. I hope you have, too. Knowing companies deeply can actually lead you to a new job. Or I referenced this earlier, but maybe an investment club friendship. That's another form of an opportunity, or maybe a conference you attend, some new industry you're studying, and you start meeting people or make new contacts in a new industry. Hey, you might even meet an entrepreneur one day whose business you decide to back. The act of studying and following trends, technologies, how our culture is changing, how business is changing, you're going to do that much better when you're researching stocks as a self-directed investor than if you're not. I think those are to me, three clear examples of the great rewards that come from choosing your own adventure as an investor. I'll close just by saying, of course, if, Kevin, you're not enjoying this or if you don't feel confident, or if you want to spend your time differently, then sure, I would say you can always revert to the indices.

That's still a fine answer for many adults who have time to compound over years and years. I mentioned this earlier, but I'll just point out again that one thing I've suggested to many people over the years is to play that game of apportioning some money toward index or managed funds and then some back to your own individual stock picking. I'm not sure what your own balance is, but you could scrutinize that, and you could move money accordingly. I should have mentioned this earlier, but that's even easier, of course, when you're doing that within a retirement account where selling has no tax consequences. Anyway, again, Kevin, thank you for being a faithful Fool over the years. Thank you for listening to this podcast, and I hope I had something there. You said thanks for suffering this Fool gladly as you signed off your note. I'm going to say it back. Kevin, thank you for suffering this Fool gladly.

Now we move on to Rule Breaker Mailbag item number 7. This one is from Ruthie Kreider. Dear Mr. David Gardner, my name is Ruthie Kreider, and I'm a huge fan and longtime subscriber. I'm an ER physician in South Georgia who's followed you and Tom Gardner since the 1990s when I was in college at the University of Georgia. First, this letter is long overdue. My intention is to share a piece of my story and appreciation for you and your team and what you've meant to me. Feeling grateful today for you and your brother Tom, all the advice, ups and downs along the way of being a Fool. I've long wanted to write you a personal letter, thanking you, but hesitated for different reasons, but today is the day. Especially with Nvidia earnings reported yesterday. Following your advice, I have slowly invested over many years, hoping one day to hit some winners and turn a small piece of the pie into a bigger one. I have followed you for years, received all my stock advisor tips in the mail, reading every one, and investing in some along the way. I didn't have much to invest, Ruthie writes, and because of the support of foolish investing, I continued to purchase small bits of companies. I particularly remember you being excited about two particular stocks along the way, Netflix and Nvidia.

At the time, I probably couldn't have even understood what these companies produced, but I knew your advice was valuable. I can remember your energy and enthusiasm in the articles I invested. I particularly put more money in Nvidia with your second recommendation from Stock Advisor and can't recall the exact wording from the article, but you were almost insistent that your subscribers purchase shares of Nvidia. There was a desperation in your recommendation for us Fools to invest. I'll just briefly rewind the pages of history and say, that was in 2009 when I made that second recommendation. Definitely wrote about it in chapter one of my Rule Breaker Investing book, Ruthie. But for those who wouldn't be aware, it was 2009. Nvidia, which had been a six-bagger for us, had pretty much given all of that back. We were back near our cost somewhere around then, and I was thinking, I still love this company. It's grown over the last several years, even if the stock went way up and then came all the way back down, let's go ahead and recommend it again.

Anyway, let's go back to Ruthie's clause here. Because of your advice, my financial future is forever changed. For a woman from the foothills of Georgia with little to no exposure to investors or investments growing up, please know your knowledge, willingness to share, openness to encouraging the small investors, you made such a huge, positive impact. I'm so thankful for your advice over the past two and a half decades, especially at a time where people didn't need a broker to invest. What an exciting time in history, Ruthie writes, the ability to choose the stocks we wanted without a broker. Would love to have the opportunity to meet you and thank you in person one day, but until then, a letter will have to suffice. Also, thankful for TMFC, which is an exchange-traded fund offered by Motley Fool Asset Management. What a fantastic investment, Ruthie writes, as well, and I share the joy of when it opened for investment. It seems like yesterday, smiley emoji. Fool on with gratitude and respect, Ruthie Kreider.

Well, Ruthie, thank you. I've often said, investing is an act of optimism. I think I just received a beautiful note from somebody who probably looks for the good in life and through regular small sums, taking some of that money that you've earned through the important work that you do every day, and you've put that money behind people and companies that you believe can make tomorrow better. Then, yeah, sometimes over 10 years or 20 years, or in your case, 25 years, the extraordinary happens. A few small decisions faithfully held become life-improving. I'm delighted that Netflix and Nvidia did that for you. I'm even more delighted by the gratitude and joy that are in your letter from the foothills of Georgia to an ER in South Georgia, 25 years foolish and counting. Thank you for your lifesaving and life-improving work, as well, Ruthie. Sounds like you're living a dream, so thank you for letting all of us share a little bit in it this week, my foolish best to you.

Thank you to all my correspondents. Again, a reminder, our email address is rbi@fool.com. If you'd like to be featured on next month’s Rule Breaker Investing Mailbag. Thank you, September. October, bring it on. Fool on.

David Gardner has positions in Amazon, Netflix, and Starbucks. The Motley Fool has positions in and recommends Amazon, Netflix, Nvidia, Peloton Interactive, and Starbucks. The Motley Fool recommends Harley-Davidson. The Motley Fool has a disclosure policy.