December 2025 Mailbag: “Am I a Fool?”

0:00Once you get to the end of things, it gives you a perspective you never could have had because you needed to get to the end of the story in order to see what happened and to then reflect more knowingly on what went before. That's what happens for me every year right around this time. We made it to the end, the end of this year, 2025. You can look back on it. You now see all that happened, all the good, all the bad, all the fair to Midland. And so we now have the privilege of perspective. what you simply couldn't have had about 2025 52 weeks ago. We can now, all of us, see the whole thing. Zooming out one level, we can now engage in what I call portfolio-level thinking.

0:50So here we are at the end of it all, 2025. This is the last Rule Breaker Investing podcast of this year. Next week's episode will appear, as always, on Wednesday at noon Eastern, but next Wednesday is January 2026. So here at the end of it, 2025, we'll close things out as we do every month. It's your mailbag. And so let's do it. Only on this week's Rule Breaker Investing. It's the Rule Breaker Investing Podcast with Motley Fool co-founder David Gardner.

1:28Welcome back to Rule Breaker Investing. Happy, yeah, sure, Happy New Year. A delight to have you join with me this holiday week across the entire world. And yeah, I just want to review maybe briefly before we get into it, my market call that I made at the start of this year. Actually, I made it on this very podcast last year. And I said in 2025, I think the market's going up this year. And fortunately, from that vantage point in December 2024, I got it right once again. Now, longtime listeners know that I'm smiling. You're smiling with me because I make the same market call every year. In fact, here's my market call for next year, 2026.

2:08I think the market's going up this year. And I especially remember last year around this time, a lot of people did not think the stock market would rise in 2025. And indeed, a lot of people don't think the stock market will rise in 2026. And they might be right because they're right statistically one third of the time. But the reason that I'm such a good market timer with an incredible history of correct market timing calls in a world where most people I think are flipping their coin is that I always say I think the market's going up. And so I get it right two thirds of the time. So there it is a reflection on last year's market call and now next year's market call.

2:48Well, this is the mailbag episode for December 2025. Let's look back briefly at the month that was. We've had four podcasts that preceded this one. The first one was Games, Games, Games, Volume 7, continuing our favorite foolish holiday tradition with a fresh set of tabletop game recommendations, moving deliberately from lighter, easy-to-teach games to deeper, more immersive experiences. And if you were not so much of a gamer, you could just hop off the train any time in an episode But as always, I did try to balance accessibility and then richness. Games for families and casual players early and the more strategic thinky fare later on.

3:31All vetted for availability and joy. I'm really happy to say I've already gotten a lot of notes from people who bought one or more of our Games, Games, Games Volume 7 and put it under somebody's tree this past month. And you know that sparks joy for me. You know, Volume 7 isn't just a gift guide, though. It's an invitation to gather and laugh and reconnect around the game table. I think if you have a table like that anywhere in your apartment or your house, I hope that you had an opportunity to spend it with other human beings around you these past few weeks, and even more so in the year ahead.

4:05Games, Games, Games, Volume 7, our first podcast this month. Our second was Old, New, Borrowed, and Blue, Volume 10, returning to one of my more flexible formats where I get to weave together familiar ideas with some new provocations. Always a little bit of borrowed wisdom as well. And of course, always to close, a touch of blue. Week three, the besties of 2025 celebrating the conversations that educated, amused, and enriched us most this past year on Rule Breaker Investing. Ten standout episodes return to the spotlight with many of the voices behind them rejoining for brief reflections on the year that was and the year ahead.

4:46So we had authors, we had athletes, we had analysts, producers, community members. The Besties every year captures the breadth of what this podcast aims to be. Thoughtful, optimistic, playful, and human. And maybe it is, ironically, my best podcast each year. Ironic, of course, because it can never itself win a Bestie. And finally, last week, the market cap game show Bubble Wrap and Sidewalk Robots brought another round of intuition meets valuation fun as Bill Barker and Matt Argersinger battled through 10 companies ranging from, yeah, packaging legends to autonomous delivery upstarts. As always, the game delivered, and it delivered Bill Barker into our Final Four March Market Cap Madness coming up in the first quarter of this coming year.

5:39Very excited to have all four seats filled. We'll have a March full of the Market Cap game show, and I hope you enjoyed playing along at home with us because that's half the fun. All right, I always open up every Mailbag episode with some hot takes from Twitter and a couple reflecting on, yeah, the first episode of this month. Thank you, at Gaurav K. Investor. Gaurav Kumar simply tweeted out, look forward to the Games, Games, Games episode every year. I think I have bought at least one board game from this list every year. Thank you, Gaurav and Paul Essen, at Paul underscore Essen. My favorite episode every year, Paul wrote Always helpful for coming up with gift ideas for my wife If you haven't tried it, Paul added May I humbly suggest the Slay the Spire board game My family's been really enjoying it It's an 8.7 out of 10 on Board Game Geek 1 to 4 players, medium complexity, a cooperative game And thank you for that, Paul You and I have gamed together in the past A former employee at The Motley Fool Always good to hear from you, Paul And yeah, Slay the Spire, I initially wrote you back that I hadn't really bothered with the board game because I am a fan of the video game very much.

6:52The video game, ironically, is built off of board game mechanics. It's a deck builder. so those of us who've played Dominion or other deck building tabletop card games we're interested to see it migrate that mechanic deck building into video games and Slay the Spire over the last seven years or so has been slaying the public as a huge money winner for the independent studio that produced it, Slay the Spire 2 is already on its way soon but it was all turned back into a board game and I told Paul I felt like I didn't need to play the board game because I already loved the video game Paul pointed out the board game enables you to play cooperatively with friends or family.

7:32And so guess what, Paul? Yeah, I bought myself a copy this past week. Slay the Spire, especially if you're a fan of the video game and would like to play Slay the Spire, in effect, with others around a game table, I will put in a recommendation for it as well. Thank you, Paul. And then final Twitter hot take, my favorite of the month. Certainly, I had an exchange with The Investing Monk on Twitter, at Monk Echeverria, and what a delight this was. He dropped me a note in early December saying, just now my six-year-old, the investing monk, wrote, climbed into my bed, saw me reading, and asked, Daddy, can I read to you?

8:10And he went on, I was halfway through rule-breaker investing. So he wrote, I handed her the book, and there it was, My little girl reading me aloud about letting your winners run high with the biggest smile on her face. Guess it's never too early to learn investing. He tweeted out. And then he went on. He wrote, when she finished the chapter, I asked her, do you want me to share this story to the author of the book? I have the intuition he would love to hear about it. He wrote, her eyes went huge. Can you really do that, daddy? I smiled, baby girl, you can do anything you dream in life So, at David G.

8:55Fool, she's now waiting for your reply So, late that night, I just dropped a simple tweet back And I wrote, to your daughter, the way you read to your dad With joy, curiosity, and that big smile Makes you a rule breaker already The best investors are people who keep learning new things and imagining big ideas. Keep reading, keep dreaming, and know you can do anything. And the closeout was a delight to receive. The very next morning, the investing monk came back with thank you at David G. Fool. First thing this morning, she ran to me shouting, did David answer? Did he? And when I showed her your message, she gasped and whispered, I'm a rule breaker already.

9:45I can do anything and hasn't stopped smiling since you made a little girl very happy and taught her a couple of very important life lessons on the way thanks for making the world a better place in so many ways and that was a very kind close from the investing monk but I've read many Twitter hot takes over Rule Breaker investing this podcast over the last 10 years or so and that has to be one of my favorites So cheers to at Monk Echeverria and that very wise, very foolish six-year-old girl. All right, we have four items on our year-end mailbag. I certainly got more than just this, but part of what I do each month is ask myself, what are the ones that punch most above their weight class that will most educate, amuse, and enrich?

10:35So again, thank you to all my correspondents, and thank you in particular to these four for these exchanges. Mailbag item number one, and I absolutely love this one. You know, it's my habit as I read a lot of mailbag items to pause at different points and inject a thought or two, but I'm just going to read this one straight through and then give some thoughts at the end. This is from Jake Dunn. Dear David, as we close out the year, I felt compelled to write in a first for me and express my gratitude for all that you and The Motley Fool have given me, not just as an investor, but as a person. Since joining TMF about four years ago, I've rarely missed an RBI or Stock Advisor podcast episode and often listen in to Motley Fool Money to glean a new perspective about a company or way of thinking about the world at large.

11:25I've learned so much about investing, but equally important, my life has been enriched in ways that are hard to measure on a stock chart. One of my favorite parts of becoming a fool is sharing this journey with my oldest son. Alistair. He's only seven, but he loves numbers and has always been curious about my investments, which I've shared openly with him, the ups and the downs. While he's often shocked by short-term drops, I'm quick to zoom out and show him that beautiful chart trending up and to the right over the long term. This summer, we opened a custodial brokerage account for him. my only rule was that a portion goes into a solid market-tracking ETF that I would help him pick.

12:13Beyond that, he picks his own stocks. He's hooked. Almost every night when I come home from work, I hear, Dad, how'd my stocks do today? He's learning patience, the importance of understanding, or at least being interested in, the companies he invests in, and the overall habit of investing for the future. He loves listening to the RBI podcast during our car rides and knows your voice well. One of our favorite episodes this year introduced a phrase that's become a family mantra. We are for people. While I've been fortunate enough to contribute to a 401k with a great company match since my mid-20s, My stock picking journey did not begin until I opened an individual brokerage account in the early spring of 2022 Thank goodness for The Motley Fool being there to help guide me and to talk me off the ledge As those first months were some rough early waters My portfolio certainly had a slow start for the first year or so But with patience and a little faith, I watched as it continues trending up and to the right I now hold 73 positions and haven't sold a thing in well over a year.

13:34Side note, my biggest investing regrets so far have been selling too soon. Early on, despite what I was learning from The Motley Fool, I regularly made the mistakes of selling after a brief pop to cash in on a small profit or emotionally selling a great company after a bad earnings report or some sort of media panic. I guess I'm a bit of a slow learner. As I write this note a few days before Christmas, my portfolio is up 53.77 % year-to-date in 2025. I'm letting my winners run and seeing more and more regularly occurring spiffy pops. Recently, Alistair and I were digging into the bottom of my portfolio as he likes to point out all my losers.

14:2225 of my 73 holdings are currently down. And he was a little confused when I said, that's part of the plan. He was amazed when I showed him that the returns from my fourth best performing stock alone, CrowdStrike, literally wipe out all of my current 25 losers losses. He had wide, excited eyes. Have I mentioned, I love the Rule Breaker style of investing. I share this not to boast, but to highlight what your philosophy has made possible for someone like me. An average guy approaching his 40s, not a math whiz by any stretch, busy with the demands of work, raising a young family. By following the simple blueprint you share so generously, I believe I'm building something special for my future and for my family.

15:15Thank you, David. Thank you for being a four person. Thank you for your knowledge, positivity, and kindness Thank you for giving me the tools and confidence to invest You've made a lasting impact on my life And now on my sons as well Wishing you, your family, and everyone at The Motley Fool A joyful holiday season And a wonderful new year with gratitude Jake Dunn P.S. I just finished your new book What a fun, digestible read that brings to life the philosophies and lessons you preach week in and week out. Well done. As this note came in, and our email address is rbi at fool.com. Anytime you'd like to consider being featured on our Rule Breaker Investing Mailbag, just email us.

16:04That's our email address. It always has been rbi at fool.com. And it's monitored in part by Brian Richards, who helps oversee the Rule Breakers franchise at The Motley Fool, my good friend and longtime compatriot, Patriots, brother in arms in service of breaking the rules. Brian sent me this note and he said, I think you're going to love this one, David. I did too, and I sure did. So to Jake and Alistair Dunn, I just want to say a few things. First of all, I love that Alistair comes back from school every day and says, Dad, how did our stocks do? I still do that myself at the age of 59. My dad's still around and I don't call him every day, but every day I do check to see how my stocks did.

16:44And some people think that's not the right way to approach it. Some people think, you know, you should just check in once a month or from time to time. Don't get too caught up in the market dynamics one day to the next. But from my standpoint, that would be like saying, well, I shouldn't follow my favorite sports team every day or week. I should just check in every few months or maybe once a year. And that would be a much poorer life for me. I love following the game of the stock market. but I have since I was a kid, just like you, Alistair, and I think I always will. So I want to say congratulations on your enthusiasm, and I know as you're growing up, you're learning that a bad day isn't that big a deal, and even a bad month, bad quarter, or bad year in the grander scheme are not that big of a deal.

17:28And Alistair, you have a dad who will zoom out and show you the bigger picture any time you were to get worried. I also want to say to both the Duns and everybody else who does this, I love that you're tracking against the market. I think it's smart that you selected a market tracking ETF for Alistair's account. It's just a quick way for any of us to see how am I doing with all the rest of my own stock picks? How am I doing against the market? And if you have a little ETF or an index fund, I haven't put that much in one myself ever, but it's still very helpful to just be tracking how you're doing against that.

18:03The third thing I want to say is that the biggest eye pop for most people who discover Rule Breaker Investing is exactly what Jake in his note conveyed, which is as he's sharing his portfolio with his son. you see gosh about a third of these stocks are are actually down how could that be a good thing but if you're playing the game right the game of rule breaker investing right and you're letting your winners run high and you're investing for at least three years and the list goes on of all the principles and all the habits and all the traits i'm looking for that i wrote about in my book this year if you're doing that right you're going to discover if you let time pass that not even just your best, maybe just your fourth best winner literally wipes out the losses of all of your losers and still leaves money on the table.

18:55And that's just your fourth best holding. So, so many humans live in fear of loss. They don't ever want to lose, especially when it comes to their money in the stock market. But if you're a rule breaker, you're playing the long game along with me, you're going to see you're going to lose a lot. And yet you'll see that your winners, even not even just your greatest winner, you're Your winners will wipe out all those losers and make you way more money than that. So I love that that's been your experience. And I love, Jake, that you got to share that with Alistair. And that both of you are sharing your story through this podcast.

19:29So many others are getting to listen to us here at the end of 2025. And to the Duns and to many of my listeners who understand what I'm saying and who are aligned with this as well, we are for people. Fool on, gentlemen. All right, Rule Breaker mailbag item number two. This one from Doug Schaefer. Doug, thanks for the note. Hi, David. I'm a new fool as I discovered your podcasts last summer and have enjoyed them tremendously. A question regarding 403B accounts for you. I'm someone who is fortunate enough to max out my 403B, which is$24 ,000 for 2025 and will be$24 ,500 for 2026. My question is, would I be wise to hit that max as soon as I can in a year?

20:21I'm able to handle contributing$6 ,125 for the first four months of 2026, and that would get me to the limit. That way, my money is invested sooner. Or, should I contribute all 12 months in case there are swings in the market? Thanks, Doug Schaefer. well Doug anytime I start getting questions about retirement plans while I have some knowledge and I have one myself I'm not an expert and I don't spend a lot of time thinking about them but we have people at the Motley Fool who do and I bet you know that and Robert Brokamp is one such now I didn't have time to get Robert on for a guest cameo this mailbag because it's holiday season and we're all in different places but I did get Robert to weigh in and give you some advice and answers back so here are some thoughts not just for Doug but for anybody who's thinking, is it the right thing to do, if you could, to max out your retirement earlier in the year as opposed to spreading it across the whole year?

21:22Robert had three points, Doug. The first is, he writes, the contribution limit for 2025 is actually$23 ,500, not$24 ,000. Robert adds there are additional catch-up limits for those who are 50 and older. So if Doug actually contributed$24 ,000, that would be$500 more than you should have You're going to pay taxes and penalties until it's fixed And the sooner you fix it by taking a corrective distribution, the better Now, he writes, Doug may have just mistyped this But Robert wanted to make sure that I gave the correct number to all of our listeners For when I shared this mailbag item So that's point number one.

22:05The contribution limit for 2025 is actually 23 ,500. Now, point number two, Robert writes, since the market is up more often than down in any given year, I think it's generally best to get money into the market sooner. And I want to say with Robert, I agree. That was going to be my own instinct. Generally, the earlier you get money into something that rises over time, the better you're going to do. There can be reasons sometimes to just go over the whole 12 months. If you're somebody who really has a hard time with market drops, wants to be more conservative, wants to just conservatively dollar cost average in a mechanical way and just do it equally every month and not feel the Sturm und Drang or too much the ups and downs of the market itself.

22:52If we face that in 2026, you could just drag it out and just make an equal contribution each month. But I like Robert's math here. Various studies, he writes, have looked at lump sum investing versus dollar cost averaging, basically have looked at putting it all in at once versus just taking that amount and spreading it over time. And lump sum usually wins. Of course, those scenarios aren't exactly like your own Doug Schaefer, but Robert says he bets the principle is the same. And then his third and final point, Robert shares that anyone considering this strategy with an employer-sponsored plan that offers a match does need to check with your plan.

23:35Because to receive the full match, you usually have to contribute an amount to the retirement plan with each paycheck of the year. So if you max out the account before the final paycheck of the year, you're going to miss out on some of that match. The amount that was missed may be deposited at the very end of the year if your plan offers what's known as a true up feature. But Robert adds not every plan offers this. So Doug Schaefer and anybody else listening to these thoughts, make sure if you do intend to max out your early contributions, make sure if you have a match that you're getting that match because that match is usually pretty valuable.

24:14And if the only way you can get it is to spread your contributions out over the whole year, month by month, We would suggest doing that. And a Merry New Year to you and yours, Robert Brokamp. Cheers, dog to you and to everybody else listening. That was Rule Breaker mailbag item number two. That means we have two left. On to Rule Breaker mailbag item number three, this one from Ben Stubbins. Hi, David. Longtime fool and rule breaker here, writing in from the UK. I've been investing with The Motley Fool and following your Rule Breaker philosophy for years And I've just had one of those, oh no, but also oh wow Moments that I thought you might appreciate on the podcast I've always thought of myself, Ben writes As a long-term, hold through volatility, let your winners run investor I love the idea of owning the next Amazon, NVIDIA, Mercado Libre, etc and I've actually owned a fair few wonderful businesses over the years.

25:20But recently, I decided to test how rule-breakery I really am. Of course, he puts one of my favorite adjectives, rule-breakery, in quotes, with that hyphenated Y on the end. Ben continues, I went back over my entire investing history and retroactively assigned a minimum holding period to every stock I've ever owned based on the kind of business it is. And he has five categories, and here they are. The top one are Rule Breaker category leaders, where he assigns seven-plus years to those stocks. The second is ultra-high-quality compounders. Ben calls them, he gives them five-plus years for those.

26:01The third, he calls them high-growth but volatile stories. For them, he gives them three-plus years. The fourth, speculative-slash-optionality tiny positions, to which he gives two-plus years. And finally, the fifth and last category he uses are defensive-slash-income holdings, for which he gives himself three to five years. Ben continues, I even gave myself a very generous escape hatch, because if The Motley Fool issues an official sell recommendation, my minimum holding for that stock becomes zero from that point on. So in other words, I only counted it as too early if I chose to sell before my own minimum holding period and before any Motley Fool sell alert.

26:52And the result, Ben goes on, was brutal. 72 % of the stocks I've sold, I sold earlier than my own minimum holding period. and on average I sold them 839 days, that's more than 2.3 years before that minimum date. Looking back at the names makes it even clearer. I sold Tesla years ago after a modest gain, long before its big surge in 2020 and beyond, exactly the kind of let your winners run high story I thought I was living. Also, I traded in and out of the trade desk and Shopify, taking nice profits but repeatedly stepping off the ride while the businesses continued to compound. Third, I even let go of an early position in NVIDIA for a small gain, well before it became the AI infrastructure giant it is today.

27:53On paper, I was, in quotes, taking profits and, quotes, managing risk. But in reality, my spreadsheet now shows I was paying a huge behavioral tax on my returns by cutting the flowers and watering the weeds. And even now, I can see the same instinct show up in subtler ways. Overtrimming winners that make me nervous. And tinkering with small positions just so I feel like I'm doing something. It feels prudent in the moment, but my backward-looking, minimum-hold analysis tells a very different story. The good news is that this has been a huge wake-up call. I've now one hard-coded minimum holding periods into my spreadsheet for every position I own.

28:49Two, color-coded which stocks I'm not allowed to sell yet based on his five business types. And three, Ben writes, I'm trying to channel my inner rule breaker more faithfully. Quotes, let your winners run high. and let my behavior finally match that philosophy. I don't actually want to know the pound value of what those early sales have cost me, writes this UK fool. I suspect it would be horrifying, but I'm genuinely excited that I've caught this pattern now, with 20 to 30 years of compounding still ahead of me. If this story is useful to other fools who think they're long-term players but sell a bit too fast, I'd be honored if you shared it on the podcast.

29:44Thank you for all you've taught me over the years. The philosophy was right. I just needed to bring my behavior up to its level. And in the ultimate foolish twist, I should confess that ChatGPT wrote this entire email, signed Ben Stubbins, who lists himself at the end as a very chastened but much wiser rule breaker. Well, that was a delight, hard at times to read. Ben, feeling for you and yet so happy that you're on the path that you are on now. and I really do want to say I love that you went back over your whole history and actually took the time to score it, to document the actual length of your holding periods, to see the performance that you've generated.

30:32I agree with you. You don't need to go back and see what you would have generated. That could be a little daunting. I'm just very glad overall you didn't turn the whole note, the whole mailbag item, and thanks for writing after a few years, into an exercise in self-flagellation. That's really not necessary. Our friend Shirzad Shamim would say you've just been given a gift and an opportunity. And yet, indeed, rather than turning your lessons into, I don't know, strike one, strike two, strike three against yourself, you turned it into a better new approach you're taking, learning driven, hard coded, color coded into that spreadsheet.

31:11And going forward, you're sharing it out to all as well, because we just did that through this podcast. So thank you, Ben Stubbins, for a witty at points, delightful, sometimes sad or hard to read note that, as it turns out, the whole thing was written by ChachiBT anyway. Fool on, my friend. All right. Rule Breaker mailbag item number four. And I'm going to say something like item number 50 something. If you count up all of our Rule Breaker mailbag items here in 2025, this is the very last one of them coming from Federico. Federico, thank you for this note. Hi, David. On a recent ski trip, I had the privilege and joy of hearing your audio book, followed by catching up on Rule Breaker Investing Podcasts.