September 2026 Mailbag: 16 Years Old to 25 Years Foolish

26:18Let's move on to our third mailbag item. This one comes from Andrew Gibson, Andy Gibbs, 53446 on Twitter X, a familiar correspondent. And 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. So first, just let me say thank you for a great note, Andy.

26:58You led off with that. 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 the quote every 12 minutes. And 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.

27:48And I'd highly, 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 you're 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 your own company, The Motley Fool, when the inflection point began to show up and the breakthroughs began compounding.

28:40Were 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. And 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, yeah, some scary headlines, some huge drops.

29:32And as you also pointed to, Andrew, some wonderful surprises too. And 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 I will contend generation after generation. And that's why I think the miracle metaphor deserves a little rule breaker tweaking because our job isn't to predict miracles.

30:14I don't think I'd be very good at that. It's just to recognize excellence, to buy it, to watch it, and then, yeah, 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. And Andy writes, and I quote, I had to remind him, Blake, we're investors, not traitors like David would say, but do what you need to in order to sleep well. That's what that's what Andy told his friend Blake. He goes on today. He thanks me for encouraging him to let that winner run.

30:55Still, that fear that what goes up must come down is real. The risk of giving it back is a feeling, not just a footnote. And I'll leave it right there. Well said again, Andrew Gibson. And 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 do that in that situation. I try to ask things like, has this company done anything wrong? Because a stock that goes from 25 to 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.

31:40It'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, yeah, management stumbles too. So 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. So yeah, 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.

32:18The miracle is that after you found it, you managed not to sell it. Fool on, Andy. We spend a lot of time thinking about how to grow and protect our money, but one convincing text email or fake website can put all of that at risk. Today's scams can look completely legitimate, even like your bank. And by the time an alert arrives, the money may already be gone. CoverOn is built for what happens before and after a scam. It monitors for exposed personal information, suspicious account activity, and changes to your credit. And when prevention isn't enough cover on ads expert recovery support and financial protection for eligible losses instead of juggling separate privacy identity and security tools you get a more complete layer of protection in one place one scam can cost you everything protect yourself now the first 100 users get 20 % off with code rule 20.

33:25That's rule 20 at cover on.com slash rule 20. All right, let's move on to mailbag item number four. 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.

34:09Although I was already in, because I had a brokerage account that was created from a combination of an old 401k that I had that was merged with an outgoing 401k. So 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, well, some other home run type chances that I was taking as well. The good companies included Harley Davidson, Starbucks, and Delta Airlines.

34:50The 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. So 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. So that's how we, foolish leprechaun writes me, became friends. Smiley, well, 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.

35:33I'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%. So 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 kind of investing approach.

36:22Thank you and all the best, foolish leprechaun. Well, 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 just 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. So Foolish Leprechaun, I actually think it's taken a while here, but you've gotten yourself to kind of a good mix.

37:01Now, 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. And what the numbers are is individual for each of us. You're right now at 25 % stocks, 75 % managed funds. That might be the right number for you.

37:43What 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 the 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 just 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.

38:18Sometimes we're trading more than investing, or maybe you're just not picking the right kinds of companies. And 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. So 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. And 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.

38:56We 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. So 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've read my book, you'll know there are six principles that I believe each of us should have in managing our portfolios.

39:27Also, six habits that I think we should exhibit as rule breaker investors. And 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. And if that's true, congratulations. You know, 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 just the securities, the investments, the stocks themselves. I'd want them to be able to answer questions like, why did dad own these?

40:01What are some of the things dad learned? What mistakes did he make and 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. You know, a portfolio accompanied by stories and principles, I guess is what I'm 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.

40:45All right, on to Rule Breaker mailbag item number five of seven. 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.

41:23I 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. Well, 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. And 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 just have bart somehow week after week bart is enough thank you bart and thank you brendan all right well i often say for our mailbags that i saved the best for last.

42:25And that generally means if we're going to do seven mailbag items, that would be number seven. And indeed, I love number seven this month. And I'm excited to share that with you. And I also love number six. Now, they're very different because number seven inspires us with somebody who's been playing the long game from a modest place and has done wonderfully well. So it's one of those inspiring stories that I personally can never get enough of sharing out. and so I love it. And I'm also willing to take on the tough questions, the people who didn't necessarily get it right. I kind of just shared one.

43:00Foolish Leprechaun has found he's underperforming with his stocks and he could have just left it in the managed portion of his portfolio. So I'm always taking all comers and I learned that specifically during my years hosting the Motley Fool radio show on NPR. You know, National Public Radio has some really high standards and one of them is you just take the letters as they come, all the good ones and all the bad ones. So I'm going to say I've saved the best for last because I think it's important to speak to both situations. And so both of these, I hope, are illustrative and will show them, you and me, all off at our best, at our whole, our rounded best.

43:41Rule Breaker mailbag item number six. Hi, David. I'm writing with a follow-up to two of our previous mailbag conversations. Kevin McMahon writes, I subscribed to the Motley Fool Everlasting Portfolio 2021 on July 14th, 2021, and invested heavily in its recommendations. As of September 7th, 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 Fool Portfolios membership expires October 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.

44:35And 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 six from Morgan Housel's book, The Psychology of Money, chapter six tales you win hausel 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.

45:30Could 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.

46:20So I'm really sorry to hear that. And I understand your question. Are there enough good stocks in there? And I don't know what the stocks are, by the way, and I didn't pick the stocks, 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, as I've done 52 podcasts going back to 2015, I well remember how hard it was talking about the stock market in 2022.

47:00I 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. So I just want you to know, if you followed my five 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 five-stock samplers, only two have beaten the market. And the five that have lost have underperformed the market by 60 to 100 percentage points each. So 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.

48:05And 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 is we're 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 months, 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.

48:58and before we move on to our final final mailbag item this month one or two more thoughts kevin if 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 if 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. And 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.

49:44None 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. So 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.

50:29So example number one, you deepen relationships. Example number two, 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, D.C.

51:09How 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. And if you're just indexing and you're just sort of 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. And by the way, obviously, as a stock market investor, you can become part owners of those companies as well. And then example Number three, you create opportunities.

51:43And 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. So 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.

52:29So 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. You know, 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.

53:11And I'm not sure what your own balance is, but you could scrutinize that and you could move money accordingly. And 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 thank you for suffering this fool gladly. And now we move on to rule breaker mailbag item number seven.

53:44This 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 appreciate 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.

54:22But 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.

55:06At 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.

55:50But 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 Close 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.

56:34You 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.

57:15It seems like yesterday, smiley emoji, full 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. And 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.

58:07And so 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 life-saving 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. All right. Thank you to all my correspondents. Again, a reminder, our email address is rbi at fool.com. If you'd like to be featured on next month's Rule Breaker Investing Mailbag, thank you, September, October.

58:53Bring it on. Fool on.

59:08Learn more about Rule Breaker Investing at rbi.fool.com.