"Rule Breaker Investing" November Mailbag: Gratitude and Paying It Forward

To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. To get started investing, check out our quick-start guide to investing in stocks. A full transcript follows the video.

This video was recorded on Nov. 30, 2022.

David Gardner: Here we are, Fools. It's the fifth and final Wednesday of November 2022. Seventy-three, that's the number I have for you today. If you're looking for a lucky number today, this week, this month, you now have it: Seventy-three, it's a prime number; mathematicians know how beautiful those are. And I do too, because this week's mailbag marks the 73rd consecutive monthly mailbag in Rule Breaker Investing history. Seventy-three with your Twitter hot takes, questions on Rule Breakers, thoughts aplenty, only on this week's Rule Breaker Investing.

Welcome back to Rule Breaker Investing. Let me be perhaps the last person to wish you happy November; the month is running out quickly. This is Nov. 30. The Rule Breaker Investing podcast comes out on or about 4 p.m. Eastern all year long, every week, and that particular day is right now.

It's been a fun month for this podcast. Looking back over our four previous episodes, we led off with Mental Tips, Tricks, and Life Hacks, vol. 7; that started it on Nov. 2. One week later, Company Culture Tips, Kara Chambers, Lee Burbage, back with me for vol. 10, intentionally picking the greatest hits from the previous nine episodes in that series. All of us can make our workplaces better; there are many different ways to do it. Ten of them were featured on Nov. 9. We then did a Reviewapalooza! episode; Emily Flippen joined me to review two five-stock samplers last week, the week of Thanksgiving here in the United States. It was gratitude 2022, celebrating the torchbearers, and the part of me that is only with you.

Well, here we are. It's Nov. 30. Here's some hot takes from Twitter reacting to the month that has been. Gaurav Kumar, @GauravKInvestor, it is so good to put a face to the voices. Gaurav, you're talking about having Kara Chambers and Lee Burbage, I think we just snapped a photo of ourselves, since we were all in Fool HQ together with our producer Rick Engdahl. There we were like old times, physically present in the same studio during the podcast, and we just put that out over social media, and you've got to see Lee and Kara. It's a delight for me to have seen them both for something like 17 and 25 years respectively, and counting. It was funny to think back to our first episode of Company Culture Tips together when Kara was celebrating her 10th Fooliversary and Lee his 17th. Then all of a sudden, fast-forward seven years later, and Kara has celebrated her 17th Fooliversary at The Motley Fool. Thank you for listening in, Gaurav.

Reacting to the same podcast, Jason Moore, @JimminyJilickrz, the most frequently (probably) quoted Twitter hot-taker following this podcast: Jason, thank you again. You wrote, "'compelling, not compulsory,' has been such a gem from the first time I heard it. I try and look for ways to bring this to many parts of daily life." Yes, Jason, you were rocking one of Lee's dictums, one of his prescriptions to himself and really to any HR department, if you will -- which is if you're having to make things compulsory, you probably should work harder to make them compelling, so that your fellow adults want to do the things that you're asking, as opposed to feeling like they're being compelled to fill out that form, show up for that meeting, do that thing you want them to do. "Compelling, not compulsory." A good way of thinking about planning family life sometimes, as well. Jason, thank you for that.

Two more. Carlos F-S, @cfs76: "Thank you, David! I started investing in 2021 and your [voice/advice] is always present. It has kept me calm during this period of sustained losses and it keeps me 'swimming'," writes Carlos. "Your @RBIPodcast has been a huge positive influence. I just wanted to say, Thank you, sincerely." Well, thank you back, Carlos. It takes two to tango. That's true in dancing; it's also true in podcasting. The reason I do this is because you listen in, and presumably the reason you listen in is because I do this and it's our pleasure to share with each other from week to week, in good times and bad.

One thing I did mention this month, reminding all of my fellow Fools this: Two years out of every three, the market rises, and that's why it goes from the lower left to the upper right over time. If two years in every three the market dropped, you can bet that stock market line wouldn't look so great over the long term. But the truth is, things go up more than they go down, and that's important to remember, especially in the dark times. Thank you, Carlos.

Finally @LibertyCentric, prepping me to hype up next week's podcast: @LibertyCentric writes, "My family thought they'd escaped 2022 without an abundance of board games under the [C]hristmas tree. Bwahahahahaha!! #boardgamesrule." @LibertyCentric, you're enabling me to preview next week's Games, Games, Games; I believe that one is going to be vol. 4. I've gotten into the habit once each year, the first week of December, so you still have time to order before the holidays -- my favorite board games, tabletop games, card games of the year that has been. I'll try to pick five that are typically lighter games, casual fare for families, and then five for harder-core gamers. I'm getting my lists together this week. I look forward to doing Games, Games, Games vol. 4 with you all next week

Enough then with Twitter, and I hope everyone's still using Twitter. I'm still using Twitter. I once applied for the blue checkmark, and I got it because I'm me, and it was just an authentication process. These days, the checkmarks they keep a-changing, and apparently, you might need to pay some money to use Twitter. No one yet has made me do that. I probably would pay Twitter $8 a month to post and continue to use it myself, but I realize that can be off-putting to some. Anyway, I think some form of social media connection is helpful. I intend to maintain that unless somebody has a much better idea for us. @RBIPodcast is this podcast's social media handle on Twitter. I am @DavidGFool on Twitter.

Rule Breaker mailbag, item No. 1 of six this week: Thank you, Rich Smith, for this note. "David, I want to send a heartfelt thank you and appreciation of the Motley Fool and all the podcasting content. I shared this with Motley Fool Money earlier, but this year, I won't be able to spend Thanksgiving with my family. I've mentioned it before in some of my previous messages, I'm a military Fool. I'm currently overseas for some extended duty, and wanted to offer my appreciation for what you all do. The podcast provided a much-needed reprieve from the day-to-day tempo. The market news, insights, and humor are something that I look forward to daily. Again, thank you to all the Fools this Thanksgiving season, and for helping me to pass the time while I'm away." Fool On, Rich. Well, "Fool On" has been the way I've signed off many a note since we started this company -- yeah, I think I was sending AOL emails from [email protected] back in the day in 1993-4.

Thank you for Fooling On Rich, and thank you for your service. I know so many of us here in the United States, and really all of us in every country in the world, are grateful for those who keep us safe. Thank you for the sacrifices that you make, small and large. There are many small sacrifices made by people serving the public every day. Larger ones like not getting to be with your family for Thanksgiving I particularly appreciate, so Fool On to you, Rich. I can see that you are a regular listener to Motley Fool Money.

Of course, this podcast comes out just once a week, but Motley Fool Money comes out every single day. If every listener of Rule Breaker Investing is not already also listening to Motley Fool Money, just search your podcast aggregator for Motley Fool Money, hosted by longtime Motley Fool personality and good friend Chris Hill, and a cast of thousands. Thank you, Rich, for being a daily listener to Motley Fool Money and a weekly listener to Rule Breaker Investing. Fool On to you, sir. Happy Thanksgiving to you in this season of gratitude.

On to Rule Breaker mailbag item No. 2. Welcome, Rick Munarriz, how're you doing?

Rick Munarriz: I'm doing great. Thanks, David.

David Gardner: I'm delighted to have you join with me for this mailbag point No. 2, Rick -- long-time analyst for Motley Fool Rule Breakers, writer for The Motley Fool. Man about town, is it fair to say that at this point, Rick?

Rick Munarriz: I don't know what man about town -- I've heard it used. I'm not even sure if it's a good thing or bad. I think it's a good thing. I'm a man about town, man about city, man about questioning things, I guess, so yes. Thank you, I will take it.

David Gardner: Excellent. Man about questioning things, and in this case, man about answering some questions. We've got a nice one in here from Max Karr. Rick, he writes, "Greetings, Fools. I'm a 22-year-old investor currently in my senior year of college. Love what you guys do. Very thankful I was able to find The Motley Fool at a young age. I've been learning so much with you all. I would like to ask about and discuss Robinhood [Markets]. I've used Robinhood since high school," Max writes, "I'm very thankful for it. Robinhood allowed me to begin investing small portions of money, getting some skin in the game, pushing me to further learn about and love the stock market. Although Robinhood definitely has competition, I've thought of them to be a bit of a Rule Breaker."

I'm going to pause it right there. Rick, as you think through Rule Breakers, and you know this framework as well as I do -- at this point top dog and first-mover, an important emerging industry, sustainable competitive advantage, strong past price appreciation -- the list goes on. We won't go through all six of the attributes we look for in Rule Breakers, but we've talked through them many times over the years, and we will many times again. Does Robinhood tend to grade out as a Rule Breaker for you, Rick Munarriz, or not as much a Rule Breaker?

Rick Munarriz: I think in some ways it's definitely very Rule Breaker-ish. I think you have the case where Robinhood disrupted. Obviously, it wasn't the first trading platform, the first way to trade stocks, equities, and crypto. But it did disrupt the market. The reason why so many brokers now have zero-fee commission trading is because Robinhood planted that flag and said, hey, free commission trading, and everyone said, well, we have to compete against that. It definitely disrupted the industry, and I think the founder-CEO Vlad Tenev has done a lot of things that are Rule Breaker-ish, like cutting his own path.

But on the other end of the time, the stock itself has been a disappointment since it hit the market. There had been some issues. Robinhood, like so many other trading platforms, [is] struggling lately. It's had two restructurings so far this year. There are some ways that Robinhood is not a Rule Breaker. But it definitely entered with a bang with a way of just taking a market -- the sleepiest markets are always the easiest ones to disrupt, and they clearly disrupted the brokerage market.

David Gardner: The stock has been really interesting to follow. It came public to a great deal of fanfare in the summer of 2021, when it seems like any stock that helped you in your home life, in your locked-down home life, enjoy yourself a little bit more was rocking and doing really well. The stock briefly, and I'm talking about for a week or two, touched over $80. Today, it's just below $10, Rick. The market cap for this company's still $8 billion, very substantial.

The next line I want to share from Max is known as "I understand the hate Robinhood has gotten now." What does that trigger for you, Rick Munarriz?

Rick Munarriz: Again, Robinhood, they've done a lot of good things. Just as Max, he discovered Robinhood when he was in high school, and his [inaudible], Robinhood got a lot of young people in the market. You, David, you were in the market very young. I was in the market relatively youngish. I would have loved to have a Robinhood when I was growing up, and I didn't have to go over to Morgan Stanley or any of the other major full-service brokers to get invested in the market.

Robinhood has leveled the playing field, so that is good. They have a cool little gimmick where if you open an account, you get a free share of stock; it's usually a low-priced stock. Already right away, they are just easing your way into it without having to have a lot of money to get into investors. In that way, yes, Robinhood does well in that regard.

In another regards, it's a platform that even now, even today, there's not a lot of stock trading happening on Robinhood. You think Robinhood is stocks; more than half of it, 60% of its transaction-based revenue, comes from options trading -- which is fine, but very speculative in the wrong hands, and 25% is in crypto. It was higher with crypto, but with the crypto market taking a hit. It's not the stock options, it's not like you and I that we grew up with a love for stocks and eventually said, hey, options are an interesting way to defuse some of that risk and largely sidestep crypto to a certain extent. But yeah, it is obviously catered to your young market. It gets a lot of young investors excited about trading and speculating. Obviously speculating isn't as good as investing, but it's a gateway drug to becoming a long-term investor, I hope.

David Gardner: This is not your granddaddy's, your daddy's [Charles] Schwab here -- or maybe it is, maybe this is the new form of Schwab, but there's a lot of trading. Every platform, Rick, has typically benefited from more activity, more volume, and more trading. Yeah, Max goes on, "Robinhood's mission is to democratize finance for all. This feels like generally a good push." He goes on and mentions the potential global markets expansion in the coming years. He also talks about a 3.75% interest rate on your uninvested cash, which is obviously a relatively new thing, reacting to higher interest rates. A lot higher than zero these days, which was they were about zero a year ago.

He closes, "I personally would like to live in a world where underprivileged people and investors are able to have the ability to save and put a portion of their wealth into a competitive risk-free rate. This reflects my best vision of the future." He ends by saying, "Could the 'hood be a Rule Breaker?" And Rick, to close, looking at this company, the first thing I see is that the stock, we talked about how it once was $80, it's now $10. It really has been bouncing around $10 for most of 2022, the volatility is pretty low in this one. Up to $12, down to $9, back to $11, down to $9 again. One thing I'd like to see is strong past price appreciation before I could get excited about ticker symbol HOOD, that's what I see. What do you see, in closing?

Rick Munarriz: Again, there's a little more than 12 million active monthly users on Robinhood right now. That may not seem like a big number, but for a trading platform, that is substantial. That is a lot of people. They're mostly very small accounts, so you have to keep that in mind. But again, 12 million was a lot less than where we were a year ago -- more than 20 million active accounts on Robinhood. I'd like to see that improve.

Like you, I would like to see so many other things: metrics improved, the stock price would improve. I think that's all reflective of the fact that the platform is going through a transition. I think Robinhood is promising, and it's always been on my watch list; it's always been there. It's a stock that I've been hoping gets it right, because even through their missteps, their company is doing a lot of things that you should be excited about, getting young people to invest. I hope it'd be more passionate about the discipline as an investor, because zero-fee commission trading is basically opening you up to a golden corral of investing, where you can just keep eating and eating and eating and tossing your plates, used plates, and grabbing a new one. But I do think that Robinhood's markets, their stock is in the right place, but I still think it has quite a bit a ways to go before it's actually Rule-Breakers-worthy.

David Gardner: Well, thank you. I agree as well. Technically, the company name is Robinhood Markets, which Rick was reflecting in a couple of different points. Ticker symbol HOOD. Certainly, a fascinating company to follow, one that has enabled many to get started investing cheaply. The bad news is it wasn't a great time to get started investing, as it turns out, from its IPO [initial public offering] in the summer of last year through a year and a half later to this year. But, yeah, in closing, I'll just add, Max, that I like to think that if I'm investing in something it's winning. We typically do better when we invest in stocks at their 52-week highs rather than their 52-week lows. Obviously, this rule has exceptions, but I would like to see Robinhood perk up and start to win before I committed significant capital at this point.

Rick Munarriz, Happy Thanksgiving. Good to be with you.

Rick Munarriz: Thanks.

David Gardner: On to Rule Breaker mailbag item No. 3.

"Hi, David, Rick, @RBIPodcast team, The Motley Fool Foundation, and everyone at The Motley Fool." Wow, Jumm, thank you so much. You've addressed us all with your opening. "It's a season of thanks, again," writes our biggest fan, Jumm, sometimes a correspondent for Rule Breaker mailbags. Great to hear from you again, Jumm. "It's a season of thanks, again," you write. "I want to take this opportunity to express my gratitude for all the hard work and everything that you and your team are doing for our community. I truly enjoyed all of this year's episodes. I will start my vote for 2022 Besties soon." Well, thank you for that, Jumm.

"This year," she goes on, "I would like to dedicate my special appreciation to a newly founded and growing Motley Fool Foundation. Although this year has been rough for many investors, myself included, due to the market's downturn, I remain extremely grateful that I still have the capital to invest. However, many people are still in a constant struggle. The foundation has opened my eyes to the possibility that there are many smart, innovative, and caring people with a passion to help solve and help those who struggle toward financial freedom. There isn't a lot of good news this year. But to me, the Motley Fool Foundation has been the light, joy, and hope that someone cares. Solving financial freedom is not easy; that's an understatement," Jumm writes. "But with the foundation, I'm very hopeful and will continue to be a strong ally in fighting and supporting in any way I can. I feel that my donation -- and thank you again for donating. It's FoolFoundation.org, my fellow Fools, it is the holiday time of year. We'd love to hear from you." Jumm, thank you for this.

"I feel that my donation isn't only deployed properly, but also multiplies to make a bigger impact through our fellowship. If I can have one small request, to hear an update from someone at the foundation periodically, either in future episodes of this podcast or other Motley Fool podcasts, I'm sure many members want to hear more and are eager to support. Thank you again to everyone at the foundation, everyone at the Fool for your hard work. Forever a Fool, Jumm." Well, Jumm, thank you very much.

And you know what? I've thought, yeah, we could do that in future podcasts, but why wouldn't we do that right now? Jennifer Gennaro Oxley, executive director of The Motley Fool Foundation: Welcome back to Rule Breaker Investing.

Jennifer Gennaro Oxley: Happy to be here, David. Always.

David Gardner: Jennifer, I know you're from a big Italian family first of all, so I always hear about big gatherings. What was your Thanksgiving like this year?

Jennifer Gennaro Oxley: We don't do the Italian thing for Thanksgiving. I will tell you it is hosted by my mother-in-law who believes in nothing more than the joy of the turducken from New Orleans, straight out of New Orleans. She orders it up, as she says, every year. It is a small affair, just with our immediate family, and the turducken is the star of the show. I will tell you, if any one of your listeners who have had it before, it is a unbelievable piece of culinary expertise between the chicken, the duck, and turkey.

David Gardner: It's like a turkey inside of a duck inside of a chicken, something like that?

Jennifer Gennaro Oxley: Yes. With all kinds of extremely healthy New Orleans stuffing. That's tongue-in-cheek.

David Gardner: Understood. Well, I myself always benefit every year. We call our Thanksgiving "Thanksgaming" in our family because we surround -- there's actually a lot more games than food -- but I have been the beneficiary of somebody else's generosity by Gardner cousins in Lancaster, Pennsylvania who have enabled me to eat for free for year after year. I hope they are listening to this podcast so they can hear again my gratitude, but I really appreciate going to big gatherings where I don't have to cook myself.

I know you do some of that yourself, but all right. Enough with the week that was, and the weight that we still need to lose. Jennifer, Jumm is here talking some about the foundation and the hard work that we're doing. I would love for you to just to share any updates, any thoughts here, as we end 2022.

Jennifer Gennaro Oxley: First of all, I just want to say thank you to Jumm. Jumm is one of the first people that I met when I came in in the last two years of meeting with your listeners and our members. I'll tell you one thing. I've always had a belief that in any of the work that you do, either the nonprofit space, or otherwise, you must partner and lift from within. You do that because it's critical that when we're designing new systems where we're trying to make the economy and the world more inclusive, that we are partnering with those that have had challenges to redesign it together. Jumm, you have been with us all the way, and I really appreciate it all.

I just want to say thank you, because there is no silver bullet in this work. The team here, we really enjoy your note because, A, it keeps us accountable, which is very important, because this is a public charity, and it's very critical that we are accountable and show discipline. The other thing, it gives me wings and it gives our whole team wings and hope -- you taking the time for that note. By the way, Jumm's story is on our website, FoolFoundation.org. If you want to hear more about how she started, how her family started, partnered with The Motley Fool over a long period of time, grew her wealth, and now she wants to pay a Foolward with us.

David Gardner: I'm glad you mentioned that. I enjoyed the video of Jumm telling her story, and I'm reminded Jennifer that all are invited at FoolFoundation.org to tell their story of either how they achieve financial freedom, for those who have, or how they are working hard to achieve financial freedom. It's still the case, Jennifer, that I can sign onto the website and, I don't know, turn my iPhone on myself, selfie video for two minutes, and send it in?

Jennifer Gennaro Oxley: It will always be the case. This is our foundation collectively and we need all of you, so your stories propel us all. We need you. Please send it in.

David Gardner: One of the thing I heard Jumm speak to, and I think this is important to talk about, is a multiplier effect. I think anytime we donate time, money, as they always say "time treasure talent," it's very satisfying to us. All the studies show just to put something of ourselves out there and show gratitude to the world, that's really healthy for us. But I think it's even more powerful, Jennifer, when we feel like whatever we do is going to be matched or duplicated or, I don't know, mass-produce that if I do X and there's a 3X or a 9X that comes out of that, feels great to me. Could you speak briefly to multipliers?

Jennifer Gennaro Oxley: When we started the foundation, we knew that one of our unique opportunities here was to partner with all of you, our listeners, our members, to not only redesign the systems but multiply the work on the ground. In the New Year, we will be expanding our work with the fellowship into more communities around the country. We'll be launching something called a green hub, which is our focus on one local area in South Carolina, which by the way, we have 15,000 members in South Carolina.

David Gardner: South Carolina is going to be a big state in 2023 for The Motley Fool Foundation.

Jennifer Gennaro Oxley: Why that's important is that speaking of a multiplier effect, many of our members that are in South Carolina have already partnered with us to find Rule Breakers in that local area that help people create pathways to financial freedom that are living paycheck to paycheck. The multiplier effect is not just financial, yes, of course, when we have donations that come into the foundation and then more and more command and allow us to scale the work. Thank you for that. That's one part. The other part is that hand up, that ever-important hand up, that members are already showing that our Fool listeners are showing in local markets to help us do the work, to help people that are living paycheck to paycheck. That's our multiplier effect both at hand up and the financial assets we need to scale the work.

David Gardner: Well, thank you for that, Jennifer Gennaro Oxley. A delight to have you join us for this mailbag. Thank you, Jumm, for your wonderful note and for the opportunity just to talk a little bit about that work. Jennifer, if I'm hearing about the foundation for the first time or maybe the 12th time and I'm thinking I'd like to get involved, what's the way that I can do that most conveniently right now?

Jennifer Gennaro Oxley: Two ways. Number 1 is go to our website, www.foolfoundation.org. When you actually send your note in, we listen, we respond immediately. We are so excited to hear from you. Please send your inquiries there. The second place is you can follow me on LinkedIn, Jennifer Gennaro Oxley, or any of our social media, which is all @foolfoundation.

David Gardner: Wonderful. Thank you, Jennifer. Fool On.

Jennifer Gennaro Oxley: Fool on.

David Gardner: Rule Breaker mailbag item No. 4. This one comes from Matt Cowen. Matt, you and I got to meet at our Motley Fool meet-up in Northern Virginia earlier this month, and I remember you asking me if you could send in something to the podcast, and I said yeah. You could ask me the question right there in the pub that day. But even better, you could type it out, share it, and then we could share it out through this mailbag, which is what we're doing this week. Thank you, Matt Cowen, for leaning in with the Fool. Hello, David. Here's the question I'd like for you to answer in your next podcast. How capital F Foolish or small f foolish would it be to let capital gains tax considerations drive a decision to sell? If it's not over personal, would you tell us about a time where income tax considerations were the driving force behind your decision to sell a stock? I look forward to your next podcast. Thank you, Matt Cowen. Well, whenever I think taxes, first thing I think of is the IRS. The second thing I think of is, well, not actually, but why not? Robert Brokamp, great to have you back, Bro, to Rule Breaker Investing.

Robert Brokamp: Let's just make it clear that I do have a personality and my life is not all about taxes.

David Gardner: We have tax experts at The Motley Fool who also have been on this podcast. You're not the only tax guy. I'm not even sure you fancy yourself tax guy around Fool HQ or do you?

Robert Brokamp: I would say financial planning guy, which of course taxes are a part of.

David Gardner: Indeed, and that's why often I love to have you on to answer questions like this. I will speak to Matt's question in a sec. But Robert, I have you on because you think hard about these things, you come up with frameworks and thoughts, and I know you have something to share back on whether we should allow capital gains tax considerations to, in Matt's words, drive a decision to sell.

Robert Brokamp: I'm assuming that Matthew owns a stock that he thinks he should sell, but he doesn't want to pay the capital gains tax. If that's the case, I frankly think you should bite the tax bullet and sell the stock, especially if he's proven that he's pretty good at knowing when it's time to part ways with some shares. David, you may remember Phil Marty, who is a retired IRS employee who answered all kinds of tax-related questions on our discussion boards. Sadly, Phil passed away several years ago, but he often told the story of when he decided not to sell his shares in Sysco during the dot-com days because of the taxes he would have had to pay. Well, the market took care of his tax bill by taking away his capital gains as Sysco dropped from like, I don't know, 80 to like 15. If you think it's time to part ways with the stock, don't let the tax consequences prevent you from doing it. Most people listening to this show will likely pay maybe a 15% capital gains tax rate, and that's just on the gains. You're not the cost basis or the reinvested dividends, and there are several ways to offset that tax bite if you want to.

David Gardner: I really appreciate that, and I think the higher-order thinking and what people want from Rule Breaker Investing and really for the Motley Fool overall is big picture. Let's start there. I think the big picture, which you've just given us, Robert, is that our decisions to sell most of all should be driven by two things. First of all, whether that stock looks dramatically overvalued or not to us. In other words, if the stock just on its own is asking to be sold, then waiting to sell because you don't want to pay taxes, that's not going to work out so well. You just gave a great example of that. But a second factor that does factor it is our own situation. For example, for me, sometimes I have sold a stock in part because I own too much of it. It's a great problem to have. If you own a stock that blows up in your portfolio, sometimes you're going to sell because of your own situation.

But here again, Robert, it's not about the capital gains tax considerations, it's more of an allocation decision. It's a, oh my gosh, I'm overweighted in Netflix because it's done too well. I have too much Netflix. I should balance out a little bit more. You and I know at least, I think you know this about me, I definitely know this about me, I'm not a huge fan of overbalancing or constantly balancing. Certainly, a lot of mutual funds have to do that to maintain regulatory practices. But for the most part, we as individual investors can allow winners truly to win in our portfolios. Anyway, I think for most of us, we need to see the big picture first and not get too caught up in, oh my gosh, I'm going to have to pay 15% of that here, or I also hear that in Washington, DC, we have one of the higher state or local tax bills as well. You can really lose the forest for the trees if you're thinking too much around the tax decisions instead of your allocation decisions as an investor.

Robert Brokamp: Yeah. As a financial planner, we financial planners often talk in terms of risk management. I'm glad you brought up the aspect of having too much in a single company. The truth is, a lot of risk management has a cost. It might be the taxes from selling something you're too concentrated. It might be paying for insurance, it might be other things that you do to protect your finances. It's a cost, but it's well worth the cost. As I suggested, there are ways to reduce that cost. You offset the gains by doing some tax-loss harvesting by selling some stocks that are down.

David Gardner: There you go.

Robert Brokamp: Of course, you can't buy it back within 30 days, but you could do that. You could max out your traditional pre-tax retirement accounts to lower your tax bill before the end of the year if that's suitable for your situation. There are various ways to do that. But if you do decide to sell, make sure that you set some of that money aside into a savings account so when tax time comes around, you have that cash to pay the tax bill. Because if instead, you reinvest all of the money, you're going to have to then sell some of that stock when it comes time to pay the tax bill.

David Gardner: Thank you, Robert. I guess I'll add one addendum. Matt, since you asked me point-blank, would I tell you about a time where income tax considerations were the driving force behind my decision to sell a stock? Yeah, I easily can. Just about anytime I've had a really bad loser, and I'm good. Sometimes, I hate this about me. I'm good at losing 50% or more with a stock pick, ones I've made publicly, ones I bought privately. Anybody who knows me knows I'd take more of a venture capital approach to the markets where I'm willing to lose and sometimes lose grandly in order to win even more grandly.

If you invest like me, you end up with a big loser sometimes and so you can net out some of the positive gains from appreciated positions against those losses. If I've lost $10,000 on a really bad investment and I'm overweighted in another stock, selling something around $10,000 worth of profit of that stock enables me to zero out my capital gains. Now, this is not something that I do repeatedly. But since Matt, you asked, is there a time where income tax considerations drove the decision to sell a stock? It wasn't the whole stock. It was just a portion of an appreciated stock where I do allow the capital gains decisions, in this case, capital losses, netting them out at zero to cause me to sell a portion of a winner. Robert, anything to add on that, or are we done here?

Robert Brokamp: No, you hit the highlights. I'll also point out that if you've made multiple purchases of a holding either through deliberate purchases or dividend reinvestment, that means you have multiple cost basis and you can identify the shares that you sell either to minimize the gains in this year or if for some reason this year has not been a great year for you and you're going to be in a lower tax bracket, you might want to realize some of those gains this year because you think you'll be in a higher tax bracket in the future.

David Gardner: Very well said, Robert. It's just a pleasure to talk taxes with you as many times as possible and as many mailbags as possible. I mentioned at the start of the show, this is our 73rd consecutive monthly mailbag. Does the number 73 have any resonance, any particular relevance to you right now? I realize this is an off-the-cuff question. A lot of us maybe watched some football over the course of this weekend and often offensive linemen would wear the number 73. Does seventy-three mean anything to Brokamps?

Robert Brokamp: I'm always thinking about in terms of either football or stock market history. When I hear 73, I think of the '73, '74 bear market, the crash of the Nifty Fifty, which was the worst bear market since the Great Depression. That's what comes to mind for me, and I bring that up too because I love safe withdrawal rates in retirement and how much you can safely take out each year. The worst time to be in that retiree and which gave us was really the genesis of the so-called 4% rule was people who retired around '67, '68 because very soon after they had the crash of the Nifty Fifty, which started in 1973.

David Gardner: I wish you hadn't gone there, but I'm really glad that you did. I was introducing 73 is a really positive number, but I think ultimately Robert, you made this positive by making market history front and center, which is a good thing to know and to respect if you're going to be a lifetime investor, which is what I hope everybody listening to us right now is well from Rule Your Retirement fame at The Motley Fool, we got this cameo appearance from Robert Brokamp. Great to be with you again, Bro, Fool-on.

Robert Brokamp: You too, David. Thank you.

David Gardner: All right. On the Rule Breaker mailbag, item number 5, this one from Mike McMahon ProShopGuy in and around the Motley Fool. Thank you, Mike. David, listening to your gratitude episode last week and your discussion of using the app Readwise. If you want to take it to the next level and begin to organize all of your notes in Readwise. Mike writes I would suggest you take Roam. The Roam application that's R-O-A-M for a spin. Roam is a note-taking tool for network thought, for example, all of your Readwise feeds get imported into Roam. Then Mike writes, I can tag individual notes to create connections to other notes. Another thing I use it for is capturing quotes which I can refer to later, nerdy. But I thought you might find it interesting. Mike McMann. Well, thank you, Mike. I have not used Roam yet, but I'm including this as a mailbag item because many may already have done so or if not, may appreciate knowing more. In this thought-driven world.

Increasingly we are an abstract world of thoughts. If the 19th and parts of the 20th century we're about manufacturing increasingly these days. Dematerialization, a really important trend spoken to by Kevin Kelly of wired fame, the author of the book, the inevitable. I interviewed him on this podcast a few years ago. I'm already thinking, by the way, I think I'd love to have him back in 2023. But Kevin Kelly is spoken to how things that used to be hardware around us. Let's say if you had a GPS, all of a sudden, well, your phone is your GPS these days and so that disappears. A lot of hardware, for example, DVD players or how about just DVDs at all these things. We were such a hardware-centric media-consuming world as recently as 20 years ago. Now, those have disappeared as well.

Increasingly, as human beings, maybe we're going to end up looking like the minority report where we're swiping through the air in augmented reality, I don't know what I'll be doing in 20 years. I hope I'll be doing something fun though, but increasingly I find that if you can manage your thoughts, tag them, organize them, make use of them. That leads to a better world. In fact, I'm on the Roam website right now, plugging it here. It's actually Roam research.com. But if you scroll down to the about section at the bottom of their web page, it says, "We believe that writing is a tool for thinking. If we can build a tool for helping people write, and organize their ideas more effectively, we can help them have better thoughts and solve otherwise intractable problems." That's their about section, and I like that. I'm happy to share that out even though I haven't tried it myself because I think more tools that can help us have better thoughts. Recall them, organize them. That feels like really important work here in the 21st century.

Thank you for sharing that out. Mike McMann. Part of what I did with the podcasts this month is in my mental tips, tricks, and life hacks, speaking to reading e-books and making better use of the highlighting features on the Kindle app in my case. Then that led to, oh, well, have you tried Readwise, and then Mike here is saying, have you tried Roam? We keep peeling back the layers of the onion, looking for better ways to organize toward better thinking. That's part of investing too, isn't it? Well, let's go on now to the final mailbag item, Rule-breaker Mailbag item number 6. This one's short and sweet, written by Dan Hayes Daniel's list yourselves as Dan from Danville, I might guess that's Virginia, although I'm quite sure there are Danville's in other states, but Danville, Virginia, isn't that far from Fool HQ. I'm a big fan of the Fool, says Dan, especially the Rule Breaker Investing podcast, I think it would be great.

You declare Dan, especially in a down market, to put all your cards on the table and review the very first five-stock sampler. That's a fun way to close out this particular month. Five stocks for the next five years was the very first five-stock sampler I did on Sept. 2 of 2015. What it closed out five years later on Sept. 2 of 2020, as presented on this podcast, a couple of years back, it was a winner. The five stocks for the next five years were and there were some good ones and some bad ones here. Activision Blizzard, Casey's General Stores, FireEye, MercadoLibre, and the Middleby Corporation. You have a video game producer, a convenience store pizza company, a cybersecurity company, and international e-commerce company, and a maker of pizza ovens, and lots of other kitchen aids to the commercial restaurant industry. What a Motley mix of five different stocks.

Dan, I'm here to let you know that even through hard times, I'm happy to say this five-stock sampler continues to be a champion now more than seven years later, I'm going to make a closing point about that in a minute, but I want you to know, I do keep tracking the five-stock samplers. I have them in a spreadsheet in this particular case, I'm not sure of the total return, and that's because FireEye got very confusing on they just sort back through this when I do a later review of this. In future years, FireEye rebranded as Mandiant then sold off a portion of itself to a private equity company before the rest of it got acquired by Google Alphabet earlier this year. It wasn't a great stock pick, but it's listed as minus 100% right now, my spreadsheet because Mandiant left the public markets, but I can tell you for example that Activision Blizzard is up from 28 to 74 over these seven years.

That's a nice more than a double. Casey's General Store's also up 105 to 243. I see MercadoLibre, up 110 to 937. That's been a good investment. The Middleby Corporation which was at $107 a share when I picked it in September of 2015. Well, when we closed it out a couple of years ago, five years later, as I said, it had gone 107 to 99. But these days it's up at 143 so that one is come back over. All these stocks have returned more than a triple against the stock market that has roughly doubled. Even after a really bad bear market, this five-stock sampler and many of the others still thriving. I look forward by the way, to these stocks continuing to rise. Activision Blizzard may or may not get acquired by Microsoft. That one's in the headlines right now. But stocks like MercadoLibre, we hold for the only term that matters, Dan, and that's the long term. That has continued to be a champion for this particular five-stock sampler.

Anyway, I really appreciate you enabling me a mini review-a-palooza here at the end of the month of November. While I haven't picked five-stock samplers for the last couple of years. The 30 that I did continue to be so interesting to follow and to learn from. I know we will continue doing that in 2023. Well, I want to thank you for suffering Fools gladly once again this week. As we get prepared for the very busy season of December. If you were listening earlier carefully, you already know where we're headed on this podcast next week. Get the friends and families circling around the fire for next week's games, games, games volume 4, if you desperately want a board game gift from somebody, you could afford them next week's podcast when it comes out, or if you'd like to give tabletop games as gifts to others, I'll have some ideas for you really looking forward to that next week, games, games, games volume 4 in the meantime, keep gaming and Fool On!