Rule Breaker Investing Mailbag: Add Up, Don't Double Down

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This podcast was recorded on Oct. 29, 2025.

David Gardner: World that sometimes feels too good at fanning flames, this week's mailbag reminds me we are a community of candle lighters. We've got investors naming their portfolios, questioning their habits, redefining their sleep numbers, and yes, still joking about repetitive acronyms. We're traveling from Devali Dias to Dutch diligence, from a Netflix spiffy drop to an IRA named Operation Freedom. Here's to the Builders, the optimists, and the rulebreakers. A little milestone this week. It is our 120th mailbag together. Only on this week's Rule Breaker Investing.

Welcome back to Rule Breaker Investing. Yes, the sound of rules being broken. I know some of our longtime listeners tend to turn it down just as the music plays out and the voice plays out, so they don't have to hear the sound of rules being broken. This is a really fun month for me personally. I hope it was for you. It culminated last week in Fool fest, which is our annual gathering with members, fool one members, in this case, who all flew in from around the country and really around the world to be with my brother Tom Gardner, our CEO, with me. With all of our advisors and analysts, so many of our staffers, it was a real delight. I know I'm speaking to some of you who were with me last week and thanks for joining us. You'll also note, if you have an already dear listener that my voice is not 100% this week. I would say it's about 82% right now. At the end of Fool fest, it was down to about 18%. I was squeaking, barely able to make things listenable. I'm happy to say here, recording Tuesday afternoon, October 28th, I'm most of the way back, but I know you will detect that this is a little bit more Debra Winger me than usual me. I hope you will grin along with me and bear it. Bear it, we shall, because this is an outstanding mailbag episode. We have eight items this week, and I'm really fired up to go right into them with you. But before we do, let me just look back at the month that was because this was a five Wednesday month. Therefore, this is the and final, this is the mailbag podcast for October. But let's just mention again the four places that we've been so far this month, starting on October 1st, it was blast from the past volume 11. Character. I absolutely love doing that podcast. If you had a chance to listen, I hope you enjoyed it. If you didn't hope you make an effort maybe to go back with me and listen to points made some years ago that are brought back because they feel particularly relevant right here and now blast from the past Volume 1, a week later. Nine foolish truths I hold to be self evident. This is a podcast I do once every two years, and I just put back out nine foolish truth, bedrock foundational thoughts about investing business and life. This is the 2025 edition. We won't be doing that one again until 2027.

In the middle of the month October 15th, joined by many foolish friends, as we told stories around the campfire, it was stock stories, volume 11, silicons, supply chains, and spicy wings. Thank you to each of my storytellers. The storytelling continued a week later when I brought back, as I do this time this scary time. Every year, I bring back fool all star my friend for so many years now, Robert Brokamp, who's been such a friend to so many in the Motley Fool community with his retirement advice, his humor, his great wisdom, and perspective. Once again, Robert brought scary true stories which makes them even scarier. Financial horror stories serving as warnings to each of us to make sure we're not falling into that trap or getting ready to get scammed. Robert doesn't just tell true stories, he gives us the key takeaways. It's a good one to pass around to friends so that you don't both fund a Nigerian prince. Of course, the final podcast this month is this one, your October 2025 Mailbag, couple of Twitter X hot takes before we hit item number one. Andrew Gibson @andrewgibbs53446. Andrew, you were reflecting, happy to say on our stock stories volume 11, and this is what you tweeted out. You said, what an incredible podcast of stories on the RBIPodcast. This episode felt truly relaxing and rejuvenating listening to great coworkers and friends come together, sharing laughs, lessons learned, and historical tales with humility and open minds was pure magic. It's the perfect way to recharge your batteries and immerse yourself in inspiring history. Hope everyone is having a great week and tunes in cheers and Fool on. Thank you, Andrew Gibson. Justin Harrison, thank you for this Tweet. You were reacting to my blast from the past volume 11. Character episode that Let Off The Month. Justin, @jsharry10 on Twitter X, you wrote, I loved, accept responsibility, blame no one which was one of the points made, and be a foreperson. Justin goes on. I do value seeing others' intentions, showing love and grace that also encourage results. It's a way of loving others well through accountability and care, growth with action. Thanks for your enduring wisdom. I say thank you back, Justin, because your eloquence is wisdom itself and I really appreciate you taking the time to write in. We had more than that, but with so many mailbag items left, I'm dropping the rest of our hot takeaes. Let's get right into Rule Breaker Mailbag Item number 1.

This one comes from my friend Amit Samani writing in from Bangalore, India. Hi, David, I'm writing this to you on Diwali an auspicious holiday for over 1.4 billion Indians around the world. It is a festival of lights, involving lighting dias and Lakshmi, the goddess of wealth is worshiped. Serendipitously, your blast from the past episode with this notion, which I included right there at the conclusion of lighting candles. While I'm bummed about still not getting my pre ordered physical copies of your new book in India, I finally reluctantly listened to it on Audible. It is truly a treatise, and the two minute things to remember conclusion alone is worth the whole book. Thank you for lighting the candle in each of us to not only become smarter, happier, and richer, but indeed become better versions of ourselves, Fool on Amit, Samani. Well, Amit, thank you very much. I dearly appreciate those words coming from you. I did end that episode about character, which touches investing, which touches business, which touches life. I think character is really important behind all of those things. I remember saying, at the end of that podcast earlier this month, let's you and me, fellow fools, fellow rulebreakers all. Let's be known for lighting candles, not fanning flames. Let's choose builders over arsonists. I'll just go on to say Amit that since it's my darn book and my darn podcast, I'm going to share those two minutes, those two pages that you mentioned right now, right here. They're basically just a listing of some of my favorite lines in the book.

They're key big takeaway items that I include in a short summary. Once again, they're at the books and I realize as I finished writing the book that a quiet summation of the most rule breakery points would serve as a good send off to my readers. I'm so glad you love them Amit and I'm going to share them with everyone right now. The concluding section is entitled Things to Remember. It's on page 231 and 232, and it goes like this. Six habits, six traits, six principles. Trading is the antithesis of investing in [inaudible] . Keep that jersey on. The stock market always goes down faster than it goes up, but it always goes up more than it goes down. Dips. Wait for dips. I try to find excellence, buy excellence, and add to excellence over time. I sell mediocrity. That's how I invest. Dark clouds we can see through. Throw good money after good winners win. The snap test. Would anyone notice? Would anyone care? Snap cola. Would you proudly wear the T shirt of every company you're invested in? There are no numbers for the things that matter most. The joy of investment gains is potentially infinite times the pain of loss. Buying in thirds, your sleep number. Back your thoroughbreds and retire. You also RANs. When you find a better place for your money, put it there. Whether you think you can or whether you think you cannot, you're right. If you read today's headlines, you'll conclude things have never been worse. But if you read history, you'll conclude things have never been better. Spiffy pop. What wins in investing wins in business wins in life. Thank you, Amit.

Rule Breaker Mailbag Item number 2. Speaking of two, this one comes in two different flavors, two different people with the same question, so I'm going to combine them here. It's all about habit number 2 for the Rule Breaker investor. First, from Martin Dahlgren. Thank you, Martin. Hi, David in the Motley Fool team. I'm a huge fan of your work. I've been reading your book since I started with the third edition of The Motley Fool Investment Guide back in 2017. I've read every book you and Tom have released, and I especially love your unique and witty writing style. Thank you very much, Martin. I really do appreciate that. I've been a dedicated follower of your Rule Breaker Investing concept ever since. I'm actively trying to apply the habits and principles, which brings me to a question about habit number 2. Add up, don't double down. My question is about how this habit applies to adding to a volatile stock that has gone up significantly, Martin writes, for example, if my initial purchase price is 10 and it rises to 40, great stock and I buy more at 40, would it be considered doubling down if I later buy more when the price drops to 30, even though I'm still up from my original purchase price? Thank you for everything you do for the investment community. Fool on from Sweden, Martin Dahlgren, again, thank you, Martin, for that note. Similarly, writing in from the University of Michigan, Jason Corso, who is a professor at UMshGo Wolverines. It looks like, Jason, you're the Toyota professor of AI at the University of Michigan, which sounds really awesome.

Anyway, here's Jason's question. I'm a recent convert to your foolish ways, although I did track and follow fool.com in the late '90s when I was finishing college. Jason Corso writes, if only I'd listened earlier. Well, I recently read your Rule Breaker Investing book. I've already revised my approach to investing. I manage about 50% of my portfolio, and my financial advisor manages the rest. I have a question about habit number 2. I agree with your add up don't double down habit, but there are so many ways to implement it that the habit alone seems insufficient. I'm a technical guy, Jason writes, so bear with me. The real question is, I want to add up. My portfolio is flexible. Every so many days I drop more money into the portfolio. I need to make allocation decisions. How do you really approach that up allocation? You may actually say it doesn't matter, as it's still better than doubling down, but this choice will lead to wildly different outcomes. Jason goes on to provide examples of a stock that has gone up all the way or a stock that's gone up initially, but then down the next year to other stocks that might go down then up the down. He looks at all the different outcomes and shows that, yeah, it's really quite different which one you might decide to add to. Thank you again, Martin and Jason. Anytime I get a question from multiple people, my assumption is, I need to add something or do something better or different. You both may know that I've written a bonus chapter for Rule Breaker Investing. If you go to rulebreakerinvesting.com, you can download it for free, and I basically make that bonus chapter an FAQ, a frequently asked questions, Mailbag like experience. The first draft is already up there. Anybody again, can download and read it for free. But I'm going to keep adding to it, and I think I should add something in this direction, given your good questions. Let me pre thank you for version 1.1 of my Bonus chapter, which will have some more material, thanks in part to this Mailbag Item.

The cleanest device is, of course, don't add to things persistently going down, especially when they start below your original cost basis and just keep going down. Again, the cleanest version of this advice do tend to add to the things going up. I think you both get that. When I write a book with six habits, six traits, and six principles, which is by the way, the 18 holes on a golf course. But as we do a fly by of each of those 18, I might say, it's natural to encounter them as rules based approach, the six habits of the Rule Breaker investor. Number 2 is add up. Don't double down. There's another one. Number 3, invest for at least three years. It sounds very rules based, and I hope you can both appreciate my love. Both for rules and, of course, for breaking the rules, which after all, is what we're all about. Let's go to the habits and just discuss those briefly. I call them the six habits of the Rule Breaker investor. They are not the six rules of the Rule Breaker investor. They're also not the six requirements, the six mechanical must dos of the Rule Breaker investor. I'm really trying to cultivate a habit in my readers, in this case, to tend to add to the things going up and not make the biggest mistake I think most people who somehow go poor investing in the stock market make.

That is that they think something is cheap, and then it goes down and they add more to it, and it goes down some more and they say, well, if I add now, if it just gets back to even, I'll double my money, and maybe it never does get back to even. That's almost the only way you can play the stock market, which rises on average 9-10% a year. That's about the only way you can play to poverty. That's why I really wanted to build up a habit around adding to the things that are going up. There are many different forms of investing, and you both know this is Rule Breaker Investing, and this specifically applies to Rule Breaker stocks. Some stocks are cyclical, they go up down, up, down. That's how they move forward through time. But we're really looking at rule breakers and Rule Breaker Investing. I think I owe you a little bit more thinking about how to approach existing stocks that are up for you but maybe are volatile. The first thing I want to say is, it's really more about the business in these cases and what the company is doing in these gray areas of the stock is overall a winner for me, but a loser in the past year. Rather than focus too much on the stock and what the stock has done, what should you do? Well, I think you should start asking yourself, why is the stock doing whatever it's doing? Can you pin down some clarity, some reasoning behind why the stock went up and then has been going down? Maybe without being too philosophical, I could ask this question. What is a winner? Well, on the face of it, a winner is a stock that's up. Yes, just as a loser is a stock that's down, but even more so in this context, for this Mailbag Item, I might want to say a winner is a stock that is going up.

Here's the key and only more and more looking like a Rule Breakers. Those six traits we look for in these stocks, you want to see those blossoming and growing. If the stock is down but the company is performing and looking more and more like a Rule Breaker every day, I'm very happy to add to that situation versus, let's say a company that as it falls in the near term is also tripping and maybe falling all over itself, tending to do so for reasons that diminish its Rule Breakers status. Quick example is coming to mind. Maybe it's having its competitive advantage threatened or eroded. Maybe some new technology is showing up that's disrupting this company that you've invested in. Maybe it's had more than one consecutive down quarter. Maybe the CEO just got kicked out and replaced or maybe the brand and reputation are, for some reason in decline. If you're seeing clear diminishment of the Rule Breakers stock traits, the six traits we look for in Rule Breakers, those are the stocks I would not add to. I hope this makes sense. As I say, I think I'm going to add this to the bonus chapter because you've really raised a good point. I don't want to be confusing. I want to be as helpful as possible. My best help for you both and anyone else who encounters this is when we think about adding to existing positions. A, let's make it ones that are doing well. The stock should be performing well generally. Sometimes it may have declined a little bit recently, but it probably is overall a winner for you. B, the actual business and company itself is looking more and more like a Rule Breakers as opposed to less and less. That would be the clearest reason to add or not to that stock. Thank you both for a great question. Fool on.

On to Rule Breakers and Mailbag Item number 3, this one from a fellow, Dave. Hi, David. I just finished reading your new book. I read it deliberately over 10 days to absorb all of your valuable insights. I found it to be refreshing, an affirmation of how I have been trying to follow Rule Breaker Investing principles after reading your first book with your brother Tom in 1999. I believe you and I are wired the same way regarding risk tolerance. I have always believed in being 100% invested in the stock market based on its history. I share your optimism for future results. It always goes up over time. I think I finally understand why you can never appear on CNBC. They cannot have a guest who goes against conventional wisdom. By the way, I have appeared on CNBC before, and I probably will in future, Dave, so I still smile at the point. You go on. I particularly enjoyed the chapter on sleep numbers. My current portfolio has NVIDIA, representing 44% of the total value. I guess that could be my sleep number 44. I suppose it could go higher still. If NVIDIA becomes a seven or $8 trillion company, is that possible? Well, we will see. Dave writes, I would be OK with that. Maybe Rocket Labs or Serve Robotics or toast will overtake NVIDIA. At present, I suspect the other winners in my portfolio like Shopify, Mercado Libre, CrowdStrike, and Meta will gradually consume that 44% going forward, and my sleep number will gravitate to whatever it will be. I am 67 and enjoying my recent retirement. I consider myself an investor capital, I a reader and researcher. I enjoy being an anonymous, good deed doer, hailing back to The Wizard of Oz, the 1939 version in my own community and to friends and family, a good deed doer. I owe my investing success and wealth to you and your brother Tom and other mentors along the way, such as Peter Lynch and Warren Buffett. About 60% of my net worth is in a 401K and 457 plan through my work. They consist of large cap US stock funds. I started my own investing portfolio back in the late 1990s from 0, making plenty of mistakes along the way, but I'm glad I persisted, as it is now 40% of my net worth, and I believe will continue to overtake my 401K thanks to the principles of Rule Breakers.

As a side note, I find it amusing when conventional wisdom says to gradually transfer percentages of your wealth from stocks to bonds as you age through your 30s, 40s, 50s, and 60s. If I had done that, Dave, writes, I would not be enjoying retirement today. While being 100% invested in the stock market is probably not the right approach for most people. I don't lose sleep over market fluctuations. I am prepared to weather the storms and I continue to be optimistic about the future. I know my investing purpose. For me, it's always been to maximize wealth generation over time. I will continue to be 100% invested in my 70s, 80s. He writes at the end with a question mark and 90s, full on Dave. Well, awesome note. I could just say awesome note, full stop and move on to the next Mailbag Item because Dave used so authentically and Foolishly conveyed your own mindset, your results, and though you begin by looking backwards, you end with looking to the future. You may know that's my license plate on my car here in Washington, DC. I love that word. My friend, I hope you live a long, long time. By the way, anytime we ever wish somebody a long lifespan, I'm always conscious of this new emerging word, which is really important, I hope to you, it is to me, the concept not just of lifespan, Dave, but of health span. Because what we really want to do is maximize our health span throughout life. That, of course, involves lots of things like financial wealth helps a lot with that so does remaining active, always on the go, always on the go, staying plugged in and invested in our society or in your family and friends, your community.

Staying in the game, one of those books Tom and I wrote years ago said, we don't like the word retirement. It doesn't sound like something I want to do. I don't want to retire from the world. I want to remain as invested as possible in the world and add value for as long as I possibly can. I believe, Dave, I'm preaching to the choir. One extra thought on sleep number. You mentioned that briefly. The real intent of sleep number from that chapter, chapter 16 of the book, is to cause people ahead of time to really ask themselves what is a number at which I will allow my largest position as a percentage of my portfolio to grow? What is that number? To think about it ahead of time. As you said 44 because that's your largest holding NVIDIA 44% of your portfolio, and you're right, that's much higher than most other people would tolerate. It didn't even sound as if you were starting to lose sleep over that. It sounded as if you'd be comfortable with it going higher. I'm going to challenge you back briefly and just say, what is your actual sleep number? Because I don't think it's 44, based on how you referred to it. I'm not saying you should allocate even more to NVIDIA. You know what you're doing. You've done it for decades now, and you're doing great. But just an extra thought there on sleep number. Anyway, let me end my answer as I threatened to begin it with a simple full stop mic drop. Dave, awesome note. On to Rule Breakers Mailbag Item number four, this one from Mark Minor. Thank you, Mark. Thanks to the Motley Fool, you write. I've had many spiffy pops in my Netflix investment, as well as in other stocks. Mark writes, however, when Netflix dropped 10% earlier this month, I lost more in one day than my initial investment. He goes on, not that I'm complaining. My initial investment gain is still a mind boggling, life changing 9,845% thanks to letting this winner win, Mark, yes, that means you have a 97 bagger in your Netflix, even after the 10% drop.

Congratulations, my friend. You go on, I'm curious though. Is there a name for such an occurrence when a stock loses more in one day than your initial investment, perhaps a spiffy-pop, rather than a spiffy-pop. As always, thanks for all you do for the Motley Fool community Mark Minor. Well, again, thank you, Mark. The correct term, I invented this one too, is spiffy-drop because there are spiffy-pops and spiffy-drops. You can actually encounter that if you go to fool.com/terms, you're going to see there an A to Z glossary of many of the most investment terms that we can think of. For example, just under the letter S, where spiffy-pop and spiffy-drop appear, there are a few dozen others that just start with the letter S. It's a very robust glossary of investment terms, and you would have found it there, but most of the world doesn't know to look there, but I did. I want you to know, Mark, that a spiffy-drop is a remarkable occurrence. They're going to happen anytime you have a stock that goes up 100 times in value, when it has a bad day, let's say losing 10% as Netflix did earlier this month. You're going to lose more in that single day than you put in the stock in the first place with your original cost basis. You will sometimes have spiffy-drops inevitably if you're having lots of spiffy-pops. I guess I would say it's a feature, not a bug. Netflix is my largest holding, so I certainly suffer it as well when it gave back following its slightly disappointing earnings in part because of a Brazilian tax situation. But anyway, the market chopped one 10th off of its value in a single day earlier this October. That's why we diversify and that's why we make sure we are comfortable with the sleep number of whatever our largest holding is.

Anyway, Mark, spiffy-drops come along sometimes with spiffy-pops and thank you for inquiring. Fool on. On to Mailbag Item number 5, this one from Maria. Hi, David. I've been a longtime fan of The Motley Fool Rule Breaker Investing and you're investing philosophy. Thank you, Maria. Thank you for all the inspiration, education, and good cheer you bring. I have a couple of questions I've been curious about would love to hear your thoughts on. You've mentioned before that you generally avoid investing in cyclical industries. I'd love to better understand. How do you personally define cyclical in this context? Are there particular sectors you generally stay away from? When evaluating strong past price appreciation is one of your six traits for Rule Breakers, how far back do you typically look to assess that? I believe I've heard you mention using a 3-6 month timeframe to evaluate past price appreciation. I'm curious how you think about a company that's shown strong long term performance over 3-5 years but is currently in a downturn over the past few months. How do you weigh shorter term declines against a strong longer term chart? Thanks again for the podcast and everything you do to help me become smarter. Fool on, Maria, writing in from Rotterdam in the Netherlands. Well, thank you very much, Maria, thanks for such a kind note and terrific questions. Let's start with cyclical industries. When I use that phrase, I'm usually talking about businesses whose fortunes rise and fall mainly with the economy's tides. You can think about big industrial stuff like airlines, autos, construction. How about commodity producers? When the economy and gross domestic product are humming, orders pile in, but when recession hits for these kinds of companies, they dry up. The pattern is a cycle. I would say it's not durably profitable. I do tend to avoid them because Rule Breakers, Maria, by contrast, are companies that create their own demand. These are the innovators.

These are the category creators. These are the disruptors, and their growth comes not from the economic cycle, but from solving problems or delighting customers in ways that the world hadn't seen yet. While the economy may wax and wane, great innovators, which is what the Rule Breakers are often just keep compounding, right through it. It's also worth pointing out that often their stocks don't do well in market down drafts. Often our Rule Breakers are more volatile to the downside. But here I'm talking about the company itself and its results and its performance, not its ever volatile stock. We're talking about companies that can continue to innovate into negative economic cycles. I was just looking back earlier one of our correspondents referenced our 1999 book when I first wrote about the six traits of Rule Breaker stocks. That book is Rule Breakers rule-makers. I have it on my own smartphone, as in the Kindle Lap, I have an electronic version of it. One of the things I like about the Kindle version of books and why I'm mainly an eBook reader, just one of the reasons is that you can see other people highlight parts of the book that you're reading. You can encounter what they call in the Kindle app popular highlights. I was just looking back at popular highlights for that 1999. Rule Breakers, rule-makers and I encountered this, which does a good job reminding us what Rule Breakers are and what they look like. I'm just going to share a paragraph here, Maria. This is from chapter 2 of that book, which was entitled First To A New World and I quote. We should address what you do when you can't really figure out what industry your company is in.

This believe it or not, is often the best situation of all. When some of the Internet's first great brands popped up and went public, one would typically find them lumped together into an industry classification called something like Internet. There one would find America Online, which was a service provider, Yahoo, a search engine, Netscape, software, and amazon.com, books, and all manner of others. Now, was Amazon.com a bookseller peers like Barnes and Noble or Borders Group, or an Internet commerce company peers like CDnow at the time, and Siberian Outpost, which is a phrase I wrote into that chapter, and I can't even remember what that company did. But anyway, back to the text to conclude that paragraph, I wrote, how confounding. When you have a hard time figuring out where to place a company, that inability frequently indicates that a company is creating its own industry, one of the most powerful Rule Breaker situations of all smile at such opportunities. I quoted that, Maria, just to hammer home the real difference between Rule Breakers and cyclical companies. Obviously, I'm not giving you a dictionary definition of cyclical. It's out there in other investment books. I'm focused on the Rule Breaker side of things, and I hope that definition or that consideration that you can't even quite place it in a traditional industry classification is another sign that you found a Rule Breaker.

Now, Maria, you went on with the second question about strong past price appreciation. I already spoke to that a little bit earlier on the Add Up, Don't Double Down Mailbag Item number 2. But let's talk just a little bit more about this because that stellar past price appreciation trait. That's one of my six traits of a Rule Breaker stock. I'm usually looking at what's happened in the recent past. Roughly the last three to nine months. Why do we care about that? Why do I emphasize that? Well, because I think we're looking for momentum, a certain type of momentum. It's momentum born of excellence. It's a stock that's up sharply in that window. It's probably reflecting real business progress or shifting investor perception. Therefore, I've always judged it a market signal worth noticing. It's one clue that a company might be leading, not lagging. With that said, context is always going to matter. A company, Maria, that's tripled over three years and then slipped 20% in the past few months. Well, that's not necessarily broken momentum. I would say that's just volatility.

In other words, a short term dip doesn't erase a long term pattern of excellence. I'd call that a leader catching its breath. But what I wouldn't do is chase every chart that's gone straight up or assume every downturn is opportunity. The key is and I spoke to this earlier, is to understand why the price has moved and whether the underlying story, the innovation, the leadership, the culture, still looks like a Rule Breaker to you. Based on how you asked that question, by the way, I'm guessing you may not yet have read my book Rule Breaker Investing. I think you'll really enjoy it. I do speak to this with a little bit more depth than I would in a Mailbag Item in a chapter in that book. I hope you'll take the time to read it because there's a lot more there than just that in Rule Breaker Investing. Thank you, Maria, for your note. It does remind me to mention that if you're a fan of my book, what you can do to help me most is to put up an online review, probably right there on Amazon, if you like, just your experience of the book. The more reviews that pop, the more people notice books, the more people will start to understand what investing actually looks like and we'll have more people playing the long game and thinking about buying excellence rather than waiting for dips. A little plug there if you really want to help me out, and I really do appreciate this, leaving a review makes a difference. Before moving on to Rule Breaker Mailbag Item Number 6, Maria, you're writing in from Rotterdam.

Now, as I read that, I was like, Rotterdam. I've never been to Rotterdam. I think we should have a brief moment. This is to benefit the Chamber of Commerce of the city of Rotterdam. I went to Wikipedia, and for anybody else like me, fellow Fools who don't quite know that much about Rotterdam, here we go. I'm actually going to pronounce it probably more like the Dutch here when I say, this is to the best of my ability, Rotterdam. Roll that R, Rotterdam is the second largest city in the Netherlands. By population, it is the largest by area. Rotterdam's history goes back to the year 1270 when yes, a dam was constructed in the Rota River. Hence, Rotterdam. In 1340, Rotterdam was granted city rights by William V, who is the count of Holland. The Rotterdam, the Hague Metropolitan area today with a population of approximately 2.7 million, is the 10th largest in the European Union and the most populous in the Netherlands. A major logistic and economic center, Rotterdam is Europe's largest seaport. Something else I didn't know. In 2022, Rotterdam had a population of 655,000 and is home to over 180 different nationalities. Rotterdam, in conclusion, is also known for its university, its riverside setting, it's lively cultural life, which I assume you're proud of and take advantage of, Maria, it's maritime heritage and its modern architecture. It's worth pointing out in closing that the River Delta that brings together the Rhine, the Muse, and the Schelt, that River Delta gives waterway access into the heart of Western Europe, which has earned the city the nickname Gateway to Europe and gateway to the world. There we go. I'm definitely now more educated on the Rotterdam. I trust, dear listener, you are too. Some of you actually live there, and I would recommend if you don't, you might want to visit sometime. There you go from the Rule Breaker Chamber of Commerce in favor of Rotterdam. On to Mailbag Item Number 6 of eight. This one from Jeff. Thank you, Jeff. Hi, David. I'm a long time fool dating back to your first book with Tom. When I finished my undergraduate degree in 1996 from Purdue University, Go Boilers. Jeff writes. A hearty congratulations on the recent publishing of your Rule Breaker Investing book. I am halfway through it as of now. It's been an enjoyable and renewing experience for me as an investor, who has managed my own and my family's money all along.

The review of the principles that I already knew and the learning of new knowledge and concepts has me excited for my next investing steps. The release of Supernova 2.0, the Motley Fools New Service coinciding with your books release, also has me really excited about growth investing again into the later chapters in my life. Jeff writes, the original Supernova services I subscribe to brought me and my family a lot of great investment ideas that have helped to set us up for success. In retirement down the road and my two kids future college education, I couldn't be more grateful to the Motley Fool for guiding me along in my investment adventure with these real money portfolio services. Now to my question. Is the Investor Island game still being supported? I imagine it is not. If that's the case, I'm sure I missed this announcement along the way. I recently got back on the app to play a game versus the demon bought and have tried to play versus live opponents only to be waiting for them to join after a couple of days. I can recall the last time I played the game, but it has been years. However, my eight-year-old son remembers me playing it years back and asked me about it. If there are still players out there who are playing, I'd be curious to know many thanks, Jeff. Well Jeff, the short and unsweet answer is, we no longer support Investor Island. It remains up there on the app store there for people who want to go back and enjoy a game that I and a talented gamer oriented small group of fools developed to create a game that people could use as strategy game since those who know me know I love strategy games. We created an original game with some brilliant game designers and use historic market data to drive the events from one turn to the next.

I truly loved working on Investor Island. It was definitely a bucket list item for me to launch a five star rated game in the Apple App Store, one that would help investors ultimately, it wasn't as commercially successful as I guess our company needed. So we ceased development on it. But as I mentioned, it's still up there and available. But I think you're right, Jeff, if you try to play multiplayer, it might be a very lonely existence. I suppose there's a chance anything could make a comeback. I never say never. I love doing Investor Island, so I want you to know that even though I'm sad about it, I'm so grateful you brought a smile to my face for sharing your own experience with it, including that of your son, Fool on Jeff and Fam. I'm sensing my voice is starting to fall apart. I didn't even start today as 100%. I was probably 82%, but I think I may be down in the '60s here, so just two more items as I leave it all out there on the field this week with this month's mailbag.

Mailbag Item Number 7, this one from Ross clearly writing again from the UK. Dear David, I had a good chuckle when listening to your description of repetitive acronym syndrome. RAS syndrome, when in the same podcast, you use the phrase period of time. Now, as a British resident, Ross writes, period has only one meaning for me. Time is unnecessary when used with period, which means a span of time. More importantly, thank you for the outstanding work done by you and your fellow Fools over the years. I have three of your books in my bedside cabinet, ready to go to children and spouse as presents. Best wishes, Ross. Well, Ross, you've definitely brought a smile to me. My face there. Thank you for that, my British friend. Yes, redundant acronym syndrome. That's actually the R word for RAS syndrome. It's redundant acronym syndrome strikes again. You know I love mailbag items around language. Anybody who's read my book knows that I pick my words carefully, I think we all should, because the language we use actually drives the actions that we take. Not one to one, not always obviously, but at least subconsciously, the words we choose are influencing us and others all the time. As an English major, I have a deep love and respect for language, and clearly you do too as well, Ross in my defense. While you do say in the UK, a period is, as you say, simply a span of time, over here in the States, the word has let's just say a few other associations. When an American says period of time, we're really just trying to clarify that we mean the chronological kind. I will plead linguistic innocence or at least cross Atlantic confusion on this one. Thank you, Ross and fool on.

Onto our final Mailbag Item this week Number 8, this one from Joe. Now, I'm going to declare right up front, this is a three peat. I believe this is the first ever three pet in this podcast history. By that, I mean, Joe, you wrote in a lovely note and appeared in our August mailbag. You then wrote a follow up and appeared in last month's September mailbag. Now here you are closing out our October mailbag. I don't believe I've ever featured a single person with their mailbag items three months in a row. If I'm wrong about this and any other fellow fool wants to point out, I've three peated with them, please write me, of course, our email address, rbi@fool.com. But to the best of my memory, Joe, this is the first ever three peat. Now, for those who weren't listening a couple of months ago, Joe wrote us in August, and he said this. He said, in February of this year, he turned all of his focus from sports betting to investing. Joe wrote, I grew up in a house where we didn't talk about money. 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 Joe went on waiting this long but I'm glad I at least found my path now. I've gotten my 10-year-old started off on the right path, and that was a portion of his August note. Here we go. Mailbag Item Number 8. Hi again, David. It is truly an honor to hear you talk about my journey on your podcast twice now. I don't want to pester you with emails, but I did want to report back after reading your book.

First, I feel like I should give some more background on my situation. When I said I had diverted all of my attention from sports betting to investing, Joe writes, I meant this for my hobby time. I have a long drive to work each day, so I mainly fill that time with podcasts and audio books. I did have an existing IRA that had rolled over from a previous employer's 401K. I had a good starting balance to work off of. I wanted to move away from index funds and into a more personalized investing approach and that was where my initial email came in. Now, after hearing your feedback and reading your book, I now feel like I have a clear path. My first step was establishing my purpose. My wife and I want to have freedom. When we retire, freedom to travel, freedom to treat ourselves once in a while, and freedom to explore what our new purpose is. The name of my IRA account is now operation freedom. While I continue to research stocks that fit the Rule Breaker traits, I'm building a portfolio with companies that I enjoy watching and am proud to own a piece of. One point you made that really spoke to me was that the joys of a winning stock are potentially infinitely higher than the pain of a losing stock. When I was sports betting, I really enjoyed futures bets.

For example, betting who would win the Psi Young or Rookie of the Year Award, or who would be a division winner in Major League baseball. I would research all of the sports books to find the best odds, thinking I would have one up on the sports books by doing this. Joe goes on the only problem is there was only ever one winner. I was playing a zero sum game. I could finish with three of the top four Psi young vote getters. That would be the top pitchers in baseball for a given season. Joe would have three of the top four but not win back any money. With stocks, there are multiple winners, albeit some bigger than others, but even the losers are unlikely to lose everything. Anyway, I really enjoyed reading your book and had so many more takeaways than I could capture in a relatively short email. Thank you for sharing your experiences and your wisdom. Fool on, Joe. It's funny, Joe. I read one review of my book that actually called out Chapter 14, which is entitled Know and Name It's Purpose. It is principle Number 2 of the Rule Breaker portfolio. But the reviewer said that chapter was nearly an utter waste of time. I quote," On one hand, this book is filled. He wrote with way too much fillers, such as spending a good ten pages on thinking about the purpose of your portfolio and its name.

He went on Newsflash. The purpose of people's portfolios is so blindingly obvious that pontificating about it, is wasting others' time." I will just not really so much react specifically to that review, but the chapter we're talking about here, Joe, know and name its purpose, which is what you're referencing in your note, it does make a simple point. I don't think it's filler. Having done someone else's podcast just a week ago, it was very interesting to hear them call out Chapter 14, no and name its purpose as one of their favorites. It sounds like it might be one of yours, too, Joe. Maybe for people who love purpose, who are more personally themselves, purpose driven, who look to buy purpose driven Rule Breaker companies. Maybe for us, these words, no and name its purpose are more meaningful what you choose to name your portfolio or your investment club, etc actually really does matter. It does guide your actions, and it does serve as an active reminder for you as the years go by, anyway. By the way, check it. Chapter 14 is not in the words of that reviewer a good 10 pages. It's just five pages. It was actually the shortest chapter in the book.

Anyway, let me close at the end of this month by saying, I loved doing this mailbag, in part, because I love receiving your questions and your thoughts. We had a larger load of incoming notes than usual, which I ascribed to my book having just come out and a bunch of you having already read it, which is awesome, it took me extra time and effort to keep that book short, to write it so that it was fast paced and foolish fun. I definitely put in extra time to make it read quicker and shorter. I also want to say finally now after 15 years of no new books, to help guide Rule Breaker investors. Dear listener, dear reader, you now have a trusty little green side kick on your Bookshelf, or your Kindle, or your audio book, which you can tune back into, again, anytime for inspiration. That trusty little green sidekick, given how subversive it is in its heart, it will continue to provide a challenge to the stock markets and investing world's conventional wisdom. I also want to say in conclusion, I think that trusty little green side kick will now begin to serve as a platform for greater mutual understanding on this podcast and its mailbags because once enough of us have read it, I don't have to re explain things over and over. We can get into deeper questions, deeper discoveries, more alluring mailbag possibilities. Yes. Our email address is rbi@fool.com. That is the same email we were using when we did our first mailbag, 120 months ago, November 2015. With this delightful exchange this week, we've just completed our 120th mailbag together. That's 10 years times 12 months. I'll just say in conclusion. I'm looking forward to number 121. See you next month. Fool on!

David Gardner has positions in Amazon, MercadoLibre, Netflix, Rocket Lab, and Toast. The Motley Fool has positions in and recommends Amazon, CrowdStrike, MercadoLibre, Meta Platforms, Netflix, Nvidia, Rocket Lab, Serve Robotics, Shopify, and Toast. The Motley Fool has a disclosure policy.