We wrestle with a values-alignment dilemma around owning Robinhood, explore what it looks like to turn investing into a real, score-kept game for kids (including outperforming Dad), consider a mischievous strategy for the Market Cap Game Show, and close with an inspiring note from a retired basketball coach whose patient, optimistic approach built lasting financial freedom.
Along the way, we're reminded that investing isn't just about returns -- it's about judgment, temperament, family, and choosing to be a "for" person over time.
To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. When you're ready to invest, check out this top 10 list of stocks to buy.
A full transcript is below.
This podcast was recorded on Jan. 28, 2026.
David Gardner: One of the great things about the Rule Breaker investing Mailbag is that it reminds me again and again that investing is never just about numbers. Sometimes it's about values, how you feel owning a business whose tools can be used well or misused badly. Sometimes it's about family teaching kids how to think about money, about winning and losing, about what average actually means. Sometimes it's about games we play, rules we bend, whether always clicking Disagree, for example, would be a smart strategy in the Market Cap Game Show. Sometimes these are my favorite times. It's about a life well lived, patiently, optimistically, Foolishly, one raise saved at a time. This week's Mailbag takes us to all of those places, different notes, different voices, same question underneath it all. How do we invest in a way that reflects who we want to be? Only on this week's Rule Breaker Investing.
Welcome back to Rule Breaker Investing. Here we are at the end of the first month of 2026. As I usually like to do for our Mailbags, I like to look back briefly at the weeks that were for this podcast. We had three essays from yesterday, Volume 8, followed by healing leaders, and then calculating risk Foolishly. Because I go back over the month it was, I like to remind, especially people who may have missed one of these why you might enjoy listening to them, let's briefly survey where we've been this month. We started with essays from yesterday, Volume 8, kicking off the year by reveal what I called an investor's secret weapon, and that would be history. We went all the way back to 2006, 2010, 2012, and 2014, revisiting opening essays written in the middle of forgotten sell offs, dispiriting markets, moments that felt like the worst possible time to be picking stocks. Along the way, we remember the brutal spring of 2006. Do you remember that? The second half of 2011 that wiped out half our gains? Do you remember that? The so called greatest issue ever that was from Motley Fool Rule Breakers, 2009, March when buying stocks felt awful, but it turned out to be truly a magical time to be buying stocks. We also revisited why language matters, which always matters to me as an English major and why all time highs are normal, why a single winner like Intuitive Surgical or Mercado Libre can erase years of doubt. History, it turns out, isn't nostalgia. It's actually confidence. That was the spirit of essays from yesterday Volume 8. We followed that with healing leaders, a practical conversation with Raj Sisodia and Nilima Baht anyone who leads anyone who invests or simply wants to make better decisions under pressure, Raj and Nilima argue that healing isn't soft at all. It's not a soft word. It's a strategic advantage, clearer judgment, less ego, more patience, more courage to go against the crowd. They walked us through their seven step framework in plain language, connecting it to sustainable outperformance in business and investing and offer a surprisingly simple place to start in 2026. Spoiler alert. I hope you will listen to it if you didn't get to, but the two words are practice, kindness. If you've ever felt successful on paper and depleted in real life, I think this episode is for you, healing leaders. T
hen last week, of course, calculating risk Foolishly, Volume 4. We looked at Etsy. We looked at Duolingo, and we challenged the lazy way. Many people talk about risk in investing. Instead of vague labels like medium risk, last week's episode taught you that a concrete 25 point system for seeing risk, clearly, using Etsy and Duolingos I mentioned, a live case studies can be awfully educational, awfully in the best sense of the term. Along the way, you're going to learn why studying risk is really about judging company quality and why I think higher risk doesn't automatically mean higher reward, nor does lower risk automatically mean lower reward. Better questions will lead to better decisions. We took you through 25 of them last week. It's an episode I only do once every two years. If you've ever wondered what risky actually means, I hope you will get in touch with calculating risk foolishly Volume 4. That is the month that was, this is the Mailbag, which we're about to get into. We have four Mailbag items this week. Before we start with Twitter X hot takes, though, let me briefly promote what's going to happen on this podcast next week. Because next week on Rule Breaker Investing, I'm delighted to welcome back Kevin Kelly, founding editor of Wired magazine, influential futurist, fellow Fool, one of the clearest long range thinkers of our time. Kevin has an uncanny ability to see what's coming before it's obvious. I've interviewed him before and this podcast, his wonderful book, The Inevitable. He's going to explain in ways that we can all understand how technology, business, and life itself will be changing in the coming years and decades. A conversation like next week's is going to stretch your time horizon and mine. I bet it's going to sharpen our optimism, as well. If you care about where our world is headed and how innovation really unfolds, I think you're going to find next week's episode well worth your time, almost certainly a bestie in the making. Summon the kids around the family fire and call your in laws. Next week, Kevin Kelly joins me on Rule Breaker Investing.
As is our tradition out to social media, we go. By the way, I'm @DavidGFool on Twitter X. You can follow me anytime you like. You can also follow this podcast and Rule Breaker Investing Writ Large. That's @RBIPodcast, and 14,900 of your fellow Fools also follow @RBIPodcast. I think you might enjoy following this podcast and our enlivened social media presence @RBIPodcast. Here come three, I want to call out in the past few weeks.
First, Yannis Stamatopoulos at Arkolos 77, Yannis you shared Rule Breaker Investing. The book by David G Fool was a great read with lots of investing nuggets. Yannis goes on, have now set the bar higher From multibagger stocks to spiffy pops, why not aim for the Yannis uses a moon emoji here. Why not aim for the moon by simply letting my winners run? While not everything he preaches will resonate with all, Yannis says, I myself will never buy a stock at all time highs or at an egregious valuation. We should all get to a place where we are comfortable doing what works for us on, and he calls out three things here. Imagine this bulleted list on how to invest the habits, what to invest in the traits, and how to build a portfolio, the principles. Thank you for that Yannis and what he's doing there, and anybody who's read Rule Breaker Investing can see that. He is calling out the three parts of the book in order, the six habits of the Rule Breaker Investor, the six traits we look for in Rule Breaker stocks. How to build a portfolio, the six principles of the Rule Breaker portfolio. Yannis, I'm not expecting anybody to agree with everything that I'm saying in my book, although I agree with everything that I'm saying in my book, but truly I hope everybody will pick it up and find something that they can appreciate that will make them a better investor, whether they want to follow me all the way through and agree with everything I've written from page 1-page 230 or just pick and choose. But I really appreciate you taking the time to tweet that out. Anyway, I so appreciate you taking the time to call that out.
Another tweet from Twitter X, this one @AndrewGibbs53446, Andrew Gibson. Thank you, Andrew. You wrote @DavidGFool, "Your last few episodes have been rocking. Really good catchphrasing and quotable lines, I had to watch the sting on Netflix after you told the story of going to the movie theater like seven times to see it back in the day. Super cool movie loved it". Andrew writes. Of course, he goes on, I couldn't stop thinking of slapshot, the movie with Reggie Dunlop. Fool on.
Well, thank you for that, Andrew. Yes, we were referencing in that podcast about how back in the day before streaming, before DVDs, before VHS tapes, one had to just keep going back to the theater if you wanted to see a movie over and over before it left because you probably wouldn't be seeing it for years after that. That was my experience watching the sting as a kid back in the 70s. I see you're a big Paul Newman fan in his iconic portrayal of I think it was Minor League hockey coach Reggie Dunlop in the movie Slapshot. I admit I've never actually seen Slapshot, Andrew. I know it's a cult favorite, especially among sports fans. It's quoted endlessly. Many people did see it like five, six, seven times in theaters or revival houses, simply because depending on when you saw it, there might have been no other way. Anyway, thank you for sharing that. Then a third tweet from social media @Joey_Higgins, CPA Joseph Higgins. Joe, you wrote, "At RBI podcast, I missed the Mailbag cut off, but I have a suggestion for future games, games, games, podcast, I'm betting most featured games are likely on sale for Black Friday". Joe writes, "Maybe move up that podcast to November instead of December". I want to go on to say, back to you, I do appreciate the thought, and you're not wrong. Black Friday timing could probably help some of my fellow Fools who want to buy a good board game for themselves or a family member during the holidays might snag a better deal.
But that said, I am pretty attached to the tradition we've built. Games games games does show up the first week of every December. The problem with doing it in November or earlier is that my last two podcasts every November are always my gratitude podcast, followed by the November Mailbag. It just gets really tight to program around the holidays. I think I'm going to keep games games games where it is. Another way of thinking about game games is it's not just about shopping. We're starting to get ready every December to gather with others, to gather with family, and I hope for those so inclined that there's a really good board game card game or word game somewhere nearby. It's not just about shopping in Black Friday. Although I do credit you with that thought, it's also about the gathering that we do together. That's it for my Twitter X Hot Takes. I do want to mention one special feature of rulebreakerinvesting.com, which is really the website for my book, most of all, but there is a tab at rulebreakerinvesting.com labeled Podcast, and it literally includes many of my episodic series all lined up together so you can find, for example, games, games, games, all eight that I've done over the last eight years lined up right there.
Most podcasts these days just come out chronologically and sequentially, and there's no order to it. For a podcast like mine, 11 years running, it can be hard to find the first volume of essays from yesterday, let's say, or the games games games from a few years ago. That's the beauty of the podcast tab at rulebreakerinvesting.com, where we've arranged many of my most popular episodic series, so you can just click through them one at a time and find every one of them. Onto Rule Breaker Investing Mailbag item number 1 here for the month of January 2026, we started off with a note from the Italian Fool. Thank you, Italian Fool.
Here we go. Hi, David. I'm wrestling with an investing decision and would really value your perspective. I try to follow a conscious capitalism approach, but I'm torn, writes the Italian fool about Robinhood. On the positive side, I genuinely love the product. I use several brokerages, and Robin Hood is my favorite by far, from the user experience to the interest on idle cash, the cash back card, and incentives. More importantly, I think Robin Hood has done real good, making investing accessible to younger people, popularizing commission free trading, and working to expand access to private markets. It was my first brokerage account, and it helped pull me into investing. My concern on the other side of the ledger, Robin Hood has helped popularize options trading and more recently prediction markets. While I personally have no temptation to use those features, I worry that many people will treat them more like online gambling than investing, potentially causing real harm. Other brokerages offer similar products, but Robin Hood's scale and ease of use amplify the impact. My question is fundamentally this. How do you judge whether a company creates more good than harm when its tools can be used both wisely and poorly? Should my decision be based on one, the value the product creates when used responsibly, or two, the personal value and positive behavior it enables users like me, or three, the likely behavior of the average user at scale? Is it reasonable to stay invested because I love the product and believe it adds net value to me? Or should I divest if I believe many users will misuse it? Even if the product adds a lot of value to my life, I'd appreciate any framework you use to think through these kinds of value alignment decisions. Thank you for your time and for all you do signed, the Italian Fool.
Well, first, let me just say credit where it's due that you're even asking this question tells me that you're already doing Rule Breaker investing the right way. Caring about whether a business creates more good than harm, I would say that is exactly what rule Breaker investing portfolio principle number one, is all about. That is, again, in my words that you should make your portfolio reflect your best vision for our future. I would say to you, the Italian Fool, that owning companies that reflect your best vision of the future is what we should all, not just aspire to, it's what we should all be doing. My aim in my response to you, is not necessarily to tell you what to do. I actually think you could come down in either direction on this. There are many different ways that people could come down on something like this, depending on who we each are. Instead, let me just give you some questions that I might ask, maybe a thought framework or two. The first is, I would say start with first principles. Robin Hood is a tool, and tools amplify the user. A hammer can build a house or it can break a window. The ethical question, to me, anyway, is whether the company is designing for stewardship or designing for compulsion. Then you also ask yourself at scale, like the scale of the product or service that I'm talking about. Thinking about Robin Hood at scale, and then I would also say looking at incentives. You might want to ask yourself, what does Robin Hood make the most money on and what behaviors does the app most encourage? It may encourage many different behaviors, but where are the real incentives? Is it toward investing? Who doesn't love? I certainly do the idea of commission free investing, fractional share investing.
These things are wildly good for investors. Is it encouraging and rewarding those things, or is it all about just activity and coming back and using it again and again, which isn't necessarily bad itself. I think Duolingo, a completely different business, but in some ways, a similarly attractive, one might even say addictive app. Duolingos clearly try to drive repeat activity, but I don't necessarily think that's wrong if the activity itself is good for the person or good for their family or the world. Looking at where the money is, the revenue is, is it disproportionately being driven by high velocity behaviors that we might consider harmful? That might tell you something? Or is it all about getting people to start investing? As you can see, I'm really just asking questions. I myself don't even use Robin Hood, so I don't know the answer to these questions. I'm just trying to frame it up for you.
Then I would also say that almost any product or service, when you think about it, even if it's a good product or service can be misused. For example, food. Most of us try to eat irresponsibly, but for a minority, food becomes compulsive or destructive. I think we would say the same thing of alcohol, clearly. Others would say the same thing about social media. For many, a way to stay connected, learn, be entertained, but for some, it becomes an anxiety engine. Or a time sink. The ethical question isn't whether it can be misused. I would say it's whether platforms are designing solely to maximize compulsion or whether they also seem to care about user well being. Those are some of my thoughts back for you, Italian fool and all others who ask similar questions. I want to praise that mindset in closing because investors who do ask questions like these about incentives, about stewardship, impact at scale, I would say you're playing a better game than people who only ask. Will the stock go up? Because win or lose on any single position, the way of thinking that you are exhibiting that I'm trying to speak to right here, that way of thinking also compounds like stock returns. But in this case, that way of thinking compounds into, I would say, better decisions. I would also add probably better sleep. I think, a better portfolio as well, one that you could feel proud to own and also that I think mathematically will outperform other portfolios you could have managed that are not guided by portfolio principle Number 1. Italian fool and all other fellow fools listening, I hope that was helpful Rule Breaker Mailbag Item number one.
On to Mailbag Item number two. This one from Mark. Greetings, David, last year, I wrote about turning investing into a game for my kids. This past year, the market humbled me, and it may have taught them even more. Another year over, another year to tally up our family's portfolio performances. Now, both kids were more interested in picking companies this year, so playing the investing game with real incentives helped accomplish my goal. They played it a bit safer. They wanted to reinvest in their winners, letting them run high Alphabet, Tesla, Nvidia, and Amazon. My biggest loser mark rights was the trade desk, which dropped sharply in 2025. It made me rethink my sleep number. I wasn't losing sleep, but it was tough to look at. That led to good conversation about diversification and the Gardner Kratzman continuum. It turns out both kids are already better on that measure than I am. Also, outperformed me in the Investing game for 2025. I'll just say, Mark, then includes the results of his family contest. I won't read them all out, but I will say that in 2024, they were all up over 50%, and it was very close. The S&P 500, by the way, was up 23% that year. For 2025, dad lost to Zander and Kenzie. What a great dad, though. What solid performance by the kids. Mark goes on to say, at the end of each year, we compare performance. If they beat the market, they earn a reward. If they beat my Roth IRA, they earn more. This year, Kenzie tying the markets sparked a great discussion about how matching average is actually an impressive outcome. Zander checked his performance throughout the year. He was ecstatic about his victory. Now he's already talking about a three pet. Let the trash talking begin. Mark closes. Zander did a deep dive into what his retirement portfolio may look like if he continued to receive 50% returns as he did in 2024. He determined that with 50% returns every year, he would be the richest person in the world. His eyes grew wide. I reminded him that 50% returns for the rest of his life is not realistic. But to keep striving for market beating returns, and it led to a good discussion about greed and the value of spending, saving, investing, and Mark rights giving. Thank you for the inspiration and for teaching accountability in stock picking. Well, first of all, Mark, congratulations to you and your family, and you certainly raised a smile over here in my neck of the woods in Washington DC. I bet for many listening right now. I think for a few reasons. First of all, you've obviously turned investing into a shared family language, playing the game with your kids, letting them pick companies, and tracking results, and feeling the wins. Feeling the losses, too, even as adults. That might be the most valuable investment lesson of all. I congratulate you, first of all, that you are even having that conversation and playing that game. I want to go further. I want to say you're teaching something. I think you underlined this.
You at least implied it, but you're teaching accountability, which I think is such a valuable concept. You're teaching optimism, too, by the way, but keeping score, comparing to the S&P 500, even letting the kids outperform you some years, you're reinforcing for them and for us listening to you that results matter and that matching average, sure, that can be an achievement for a lot of people. Not a failure. I'm always trying to beat the averages, and I think a big reason to invest in common stocks is to beat the averages, but not in any given year. We're talking about overall. Even in years where you just match the averages, if you are passively holding stocks, return the SAP 500 return, you're actually outperforming index funds because they're churning out and creating tax events for people who are investing in those index funds. It is true that matching average is a worthy achievement. We're all trying to do better than average as Rule Breaker investors. But finally, I also want to underline what Dad did for the kids this year. You modeled how to learn from losses, and I would say without flinching. I've lost so many times on stocks I bought for myself or for my kids stocks I've recommended to Motley Fool members. Losing, as I've often said, is such an important part of winning. The trade desk was not a good performer last year. I talked about this in essays from yesterday watching the market through 2008, '9 and how that felt for those of us who were investing. I would also say revisiting your sleep number and asking, do I have too much in any given company? Talking openly about diversification, you're showing your kids that great investors don't avoid discomfort. We use it to get better, and we're always going to feel it from time to time in future. There will be more bad bear markets, and there will be more better bull markets than bad bear markets. But learning how to lose, not just in investing, but in life is such a valuable trait, as well. That's accompanied by that accountability and that gamesman that you've brought to your family. Mark, thank you for sharing some of what your family does for many other families listening. I bet you've generated some enthusiasm. You may have some exemplars here now in the year of 2026 going forward. Full on. Onto Mailbag Item number three, Rich Kaplan, writing in Rich wrote. Hi, David, Happy New Year. I think the market is going up this year, says Rich Kaplan. Difficult to say after three up years, but I'm trying to channel my inner David Gardner. A comment about the Market Cap Game Show. This is a compelling comment, by the way, Rich, thank you for it.
You asked Emily Flippen about a tip on how to play the game on your recent Bestis podcast in December. My tip, Rich, writes, is simply to disagree with whatever the range cited is for the market cap posed for any stock. I'm pretty sure if you're able to go back through all the Market Cap game shows and tally it up, you'll find disagree earns a point at least 70 to 75% of the time. I understand this is not in the true spirit of the game and makes the game less enjoyable. Nonetheless, I am struck by how often this works. Fool on, Rich Kaplan Well Rich. First of all, I love the mischievous brilliance of this. I'm not ready to crown always disagree as the official Market Cap Game Show strategy, but I will mention coming up just weeks away now, as we hit the month of March, we will once again have March Market Cap Madness where we'll be playing the Market Cap Game Show with some of our world champions. All month long. I'm going to keep a personal tally. Rich, you should do this, too. Anybody else can be mischievous along with both of us. Let's count and see how many times in March Market Cap Madness disagree works. We've had dozens of Market Cap Game shows. I definitely don't have stats on all of them, so I can't confirm or deny your 70 to 75% supposition that disagree is the smart money answer. But we can at least use this coming March just weeks away as a wonder laboratory to test out your assumption. I will also point out I realize you said you don't think it's in the true spirit of the game, you think it may make the game less enjoyable. I disagree. I think that is fascinating. Because our final four will probably hear this podcast, they will factor that into their own strategies, won't they? The Heisenberg uncertainty principle reminds us that when you observe something or when you observe something about something, you change the nature of that thing itself. Rich, I think you may have changed the future course of all market cap game shows through your undocumented supposition that disagree is the smart money answer. Thank you very much for your note. Mailbag item number three, a delight for the Market Cap Game Show. We move on to the last Mailbag Item for a shorter mailbag this month onto Rule Breaker Investing Mailbag item number four. We've had three really good ones so far. Do I save the best for Last Each Mailbag? You be the judge onto this note from Tom. Dear Fools, my name is Tom. I'm a retired high school basketball coach in Dallas, Texas. I've been meaning to write in to tell how much the capital F, foolish way has changed my life. My late father and I were always interested in stocks and actually read the Wall Street Journal together. In order to see stock prices every day, how old does that make us feel? In fact, I got my BS in finance from the University of Illinois. I played basketball in high school in Illinois, and though my career path was supposed to be working in the financial services industry in Chicago, I always had a passion for basketball. When I got my first coaching job, starting pay, the year was 1990, $27,000. My dad encouraged me to contribute to a vanguard IRA, starting with as little as $75 a month.
As the years passed, I saved my raises. My dad used to always say, You live just fine on last year's money, save your raise. I've invested in mutual funds on a monthly basis since 1990, but never traded any individual stocks. Got involved with The Motley Fool in 2015 and really bought into your long term buy and hold mentality. I married late in life, 2017, and that's when I sold my house for a profit of $180,000. I needed to make a decision about how to invest this windfall. I took that $180,000 and bought 12 stocks that you recommended the best of them all being Mercado Libre, which is now a 20 bagger, and really enjoyed watching my portfolio grow. As I gained knowledge and confidence, I took the money in my traditional IRA, about $225,000 and started actively trading stocks. My wife and I use our full Roth contribution every year, and with a combination of all those, my portfolio is now worth almost $2 million after taking out 300,000 to buy a new lake house. I never once in my life, made $100,000 a year, close, but not quite there. I only say that to let people know they can do it. If I can do it. But mostly I say that to encourage other capital F fools who may think they're unable to do what the financial services industry says is too complicated for us so called dumb money small F fools to handle. In a sometimes cynical world, sometimes corrupt industry, your radiant optimism and your kindness are a bright spot in my day. With all that said, I can't begin to thank you enough. Fool on. Tom. What a beautiful note, and even more than the note itself, which I want to thank you for sharing with us all, Tom, I want to praise the actions that led to that beautiful note. You've reminded us that one doesn't need a flashy income. To build real wealth. What we need is time, I would say consistency. I would also say the courage to believe you can do this yourself, and not everybody obviously has courage like that. Tom never made six figures. He did save his raises, listening to a very bright dad with whom he used to pour over the Wall Street Journal Paper Edition and look at stocks and stock prices, even though Tom himself for many years, never bought a single stock, but you invested steadily. Yes, you let compounding do what it does best. I have to underline that from your story.
Also, for those listening, I want to say, Tom, the biggest edge that most people have, I don't think is information. It's very helpful in this info rich world to use recent information or future information. I would never again say that in order to improve our investing choices, but really the biggest edge most people have, I think, is not information. It's temperament. Didn't trade for decades, and then you moved thoughtfully into individual stocks when you felt ready, and then you let winners like, Mercado Libre, one of our 100 plus baggers at Motley Fool Rule Breakers, do the heavy lifting for you. I also want to say something about dumb money. It's very common these days that anytime so called retail investors are called retail investors, using that phrase often in journalistic creations, whether it's on television or in the newspaper, the retail investor is usually treated as if he or she is dumb money. I think that's one of the great myths and oversights of our time ordinary people investing with patience and optimism. And I know so many of them through the Motley Fool. Can and to outperform this financial services industry that, by the way, often benefits from making things feel too complex to even try. I'm not trying to be too cynical about this because I'm a for person. I just want to say I am for the dumb money. If by dumb money, we mean people who are saving their own money, choosing to invest it themselves rather than giving it over to somebody else to whom they'd have to pay, obviously, fees, people who have the courage to try this and do it themselves, maybe not all at once, and maybe it takes a while, but if that's what dumb money looks like today, count me in. With and for the dumb money so called. Then, let me just close with a note, of course, about optimism. I can't wait to have Kevin Kelly on this program next week because not only is Kevin Kelly a futurist, he's an optimist and so much of the future I wrote about this in my book, Rule Breaker Investing is often made to sound dystopian and scary. It misleads people into thinking they shouldn't invest because clearly, didn't you see Blade Runner? I don't want to live in that futuristic world. We would have thought back in the days when the original Blade Runner came out, I think it was set in LA in 2016, and by the way, LA in 2016 didn't look anything like Blade Runner. I would just say in conclusion, radiant optimism. Is not naive for people like Kevin Kelly, certainly, I'll speak just for me for myself, and I bet for a lot of you listening to me right now, it's not naive. It's actually practical. In a cynical world, choosing to think and act for the long term, choosing kindness and choosing to believe in yourself and your ability to learn more as you go, those things that optimism may well turn out to be behind the most profitable decisions you make in your life. I want to thank Tom for his wonderful note. As always, I want to thank all of my correspondents this week, and thank you, dear fool for suffering this fool gladly here at the end of the year's first mailbag. I hope you have a wonderful week. Thanks for tuning in and fool on.
