January 2026 Mailbag: Values, Kids, Games & Inspiration

0:00One 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. And 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. And sometimes, these are my favorite times, it's about a life well-lived, patiently, optimistically, capital F foolishly, one raise saved at a time.

0:49This 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. It's the Rule Breaker Investing Podcast with Motley Fool co-founder David Gardner.

1:15Welcome back to Rule Breaker Investing. Here we are at the end of the first month of 2026. And 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 eight, followed by healing leaders and then calculating risk foolishly. And because I go back over the month that was, because 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 revealing what I called an investor's secret weapon.

1:53And that would be history. We went all the way back to 2006, 2010, 2012, and 2014, revisiting opening essays written in the middle of, yeah, forgotten sell-offs, dispiriting markets, moments that felt like the worst possible time to be picking stocks. Along the way, we remembered the brutal spring of 2006. Do you remember that? The second half of 2011 that wiped out half our gains. Do you remember that? And 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.

2:45Why 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've followed that with Healing Leaders, a practical conversation with Raj Sisodia and Nilema Bhatt for anyone who leads, anyone who invests, or simply wants to make better decisions under pressure. Raj and Nilema 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 And yeah, 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.

3:56And then 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. So 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 Duolingo, as I mentioned, as 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.

4:41Better questions will lead to better decisions. So we took you through 25 of them last week. It's an episode I only do once every two years. So if you've ever wondered what risky actually means, I hope you will get in touch with Calculating Risk Foolishly, Volume 4. So 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.

5:27Kevin has an uncanny ability to see what's coming before it's obvious. I've interviewed him before in 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. So 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.

6:08So summon the kids around the family fire and call your in-laws. Because next week, Kevin Kelly joins me on Rule Breaker Investing. All right. As is our tradition, out to social media we go. By the way, I'm at David G. Fool on Twitter X. You can follow me anytime you like. You can also follow this podcast and Rule Breaker Investing writ large. That's at RBI podcast. And 14 ,900 of your fellow fools also follow at RBI podcast. So I think you might enjoy following this podcast and our enlivened social media presence at RBI podcast. So here come three I want to call out in the past few weeks. First, Yanis Stamatopoulos at Arkelos 77.

6:53Yanis, you shared Rule Breaker Investing. The book by David G. Fool was a great read with lots of investing nuggets. Yanis goes on, have now set the bar higher from multibagger stocks to spiffy pops. Why not aim for the, Yanis 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, Yanis 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, just imagine this bulleted list on how to invest, the habits, what to invest in, the traits, and how to build a portfolio, the principles.

7:46And thank you for that, Yanis, 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, and yeah, how to build a portfolio, the six principles of the Rule Breaker portfolio. And Yanis, 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 one to page 230 or just pick and choose.

8:27But 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 from at Andrew Gibbs, 53446 Andrew Gibson. Thank you, Andrew. You wrote at David G. Fool, 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.

9:17One 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. And that was my experience watching The Sting as a kid back in the 70s. And I see you're a big Paul Newman fan and his iconic portrayal of, I think it was minor league hockey coach, right? 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.

9:58Anyway, thank you for sharing that. And then a third tweet from social media at Joey underscore Higgins, CPA, Joseph Higgins. Joe, you wrote, At RBI Podcast, I missed the mailbag cutoff, 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. Well, 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.

10:42But that said, I am pretty attached to the tradition we've built. Games, Games, Games does show up the first week of every December. And 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. so it just gets really tight to program around the holidays. So I think I'm going to keep Games, Games, Games where it is. Another way of thinking about Games, Games, 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.

11:22So 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. Okay, 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. You know, most podcasts these days just come out chronologically and sequentially, and there's no order to it.

12:05For 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. All right, on to Rule Breaker Investing Mailbag item number one. Here for the month of January 2026, we start 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.

12:45I try to follow a conscious capitalism approach, but I'm torn, writes The Italian Fool, about Robin Hood. On the positive side, I genuinely love the product. I use several brokerages, and Robinhood is my favorite by far, from the user experience to the interest on idle cash, the cashback card, and incentives. And more importantly, I think Robinhood 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, Robinhood has helped popularize options trading and more recently prediction markets.

13:35While 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 Robinhood's scale and ease of use amplify the impact. So 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 in users like me, or three, the likely behavior of the average user at scale?

14:26Is 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. You know, caring about whether a business creates more good than harm.

15:03I would say that is exactly what Rule Breaker Investing Portfolio Principle No. 1 is all about. That is, again, in my words, that you should make your portfolio reflect your best vision for our future. And 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. So 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.

15:44So instead, let me just give you some questions that I might ask, maybe a thought framework or two. And the first is, I would say start with first principles. So Robinhood is a tool, and tools amplify the user. A hammer can build a house or it can break a window. So the ethical question, to me anyway, is whether the company is designing for stewardship or designing for compulsion. And then you also ask yourself at scale, like the scale of the product or service that I'm talking about. Thinking about Robinhood at scale. And then I would also say looking at incentives. You might want to ask yourself, what does Robinhood make the most money on?

16:31And 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. Duolingo is 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.

17:20So 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 Robinhood, so I don't know the answer to these questions. I'm just trying to frame it up for you. And 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 responsibly, but for a minority, food becomes compulsive or destructive.

18:01I think we would say the same thing of alcohol, clearly. Others would say the same thing about social media. For many, of course, a way to stay connected, learn, be entertained. But for some, it becomes an anxiety engine or a time sink. So 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. So those are some of my thoughts back for you, Italian Fool and all others who ask similar questions. And 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?

18:53because 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. And I think, yeah, a better portfolio as well, one that you could feel proud to own and also that I think mathematically will outperform reform other portfolios you could have managed that are not guided by portfolio principle number one. So Italian fool and all other fellow fools listening, I hope that was helpful.

19:34Rule breaker mailbag item number one. Did archaeologists discover Noah's Ark? Is the rapture coming as soon as the Euphrates River dries up? Does the Bible condemn abortion? Don't you wish you had a trustworthy academic resource to help make sense of all of this? Well, I'm Dan Beecher, and he's award-winning Bible scholar and TikTok sensation, Dr. Dan McClellan. And we want to invite you to the Data Over Dogma podcast, where our mission is to increase public access to the academic study of the Bible and religion, and also to combat the spread of misinformation about the same. But you know, in a fun way.

20:14Every week we tackle fascinating topics. We go back to source materials in their original languages. And we interview top scholars in the field. So whether you're a devout believer or you're just interested in a clear-eyed, deeply informed look at one of the most influential books of all time, we think you're going to love the Data Over Dogma podcast. Wherever you subscribe to awesome shows.

20:40All right, 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. So 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 writes, was the trade desk, which dropped sharply in 2025.

21:23It made me rethink my sleep number. I wasn't losing sleep, but it was tough to look at. And that led to good conversation about diversification and the Gardner-Kratzman continuum. Continuum, it turns out both kids are already better on that measure than I am. They also outperformed me in the investing game for 2025. And I'll just say Mark, that 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 Xander and Kenzie. What a great dad, though.

22:05What 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 kind of an impressive outcome. Xander checked his performance throughout the year. He was ecstatic about his victory. Now he's already talking about a three-peat. Let the trash talking begin. Mark closes, Xander did a deep dive into what his retirement portfolio may look like if he continued to receive 50 % returns as he did in 2024.

22:47He determined that with 50 % returns every year, he would be the richest person in the world. And 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, it led to a good discussion about greed and the value of spending, saving, investing, and, Mark writes, 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, D.C., and I bet for many listening right now.

23:29And 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. And yeah, feeling the losses too, even as adults. That might be the most valuable investment lesson of all. So I congratulate you, first of all, that you are even having that conversation and playing that game. And 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.

24:09You'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. Of course, 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. And even in years where you just match the averages, if you are passively holding stocks that return the S &P 500's 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.

24:54So it is true that matching average is a worthy achievement. Of course, 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 have lost so many times on stocks I've 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. So watching a big drawdown. Yeah, the trade desk was not a good performer last year. Watching the market. I talked about this in essays from yesterday.

25:33Watching 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. And that's accompanied by that accountability and that gamesmanship that you've brought to your family.

26:18So, Mark, thank you for sharing some of what your family does for many other families listening. And I bet you've generated some enthusiasm. You may have some exemplars here now in the year of 2026 going forward. Fool on. On to 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 Besties podcast in December.

27:01My 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.

28:00and 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 wonderful 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.

28:40I disagree. I think that is fascinating. And 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. So 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. I want to thank you very much for your note. Mailbag item number three, a delight for the market cap game show.