We've got the Rule Breaker Investing mailbag!

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 Oct. 27, 2021.

David Gardner: How much money could you have made on GameStop? Why is investing literacy so poor? How many stocks is too many stocks for your portfolio? He who plans early plans twice. Agree or disagree? Besides investing, what other situations are benefited by inertia, non-activity rather than activity. Do you agree with these cultural generalization shared this week about the American Midwesterners? Why did I follow you on Twitter? Do you dear listeners see any connections between crypto and Linux? Finally, I thank you by saying, thank you, you reply to me, no problem. This has never rubbed me the right way, but is this simply generational? Did I just ask nine questions in a row? Are these the nine mailbag items on this week's podcasts previewed? Does Betteridge's law apply to any of the questions I've just asked besides the last one? It's time, let's go, October Mailbag only on this week's Rule Breaker Investing.

Welcome back to Rule Breaker Investing. You may have already guessed there are nine mailbag items to talk through this week. Very much looking forward to all nine of them having previewed each as a question, not a headline but it's a question in this week's opening. Well, let's look back at the month that was. There were just three previous podcasts this month for Rule Breaker Investing. The first on October 6th, was mental tips, tricks and life hacks Volume 6. That's certainly generated some mail. We'll be talking through some of the viewers, some of what we learned together then, the following week was my nine Foolish truths that I hold to be self evident 2021 version, that one was on October 13th, I do that every two years that same week of October. I hope that you enjoyed it. In fact, I hope it sounded a little repetitive to you, because if it did, that means you've been around long enough that you're getting it and I'm delighted to know that I'm also always delighted to rollout the red carpet to anybody and everybody who is new this week of the podcast or any other, and nine Foolish truths I hold to be self evident. 

Well, if you're new this week, I would highly encourage you to listen back a couple of weeks and hear what we take for granted, which is really important to know before you get started with us on Rule Breaker Investing. Then of course last week, I think it was a tour to force personally, I loved this podcast, conscious politics with Matthew Dowd. Now conscious we talk a lot about on this podcast in many different contexts, politics, rarely. To put those two together though, and have somebody who is silver tongued and actually a practitioner of it themselves. I was excited to have that conversation with Matthew Dowd and that was the month that was which has generated, as usual, a Motley array of mailbag items. In fact, I'll be joined by a couple of guest stars today. I've got Jim Gillies coming right up real soon, his debut on Rule Breaker Investing, and then a regular go-to guests toward the end of the show, Aaron Bush. Those are my two guest stars this week. Now I want to mention before we really get started this week, that next week I'm pretty excited to be joined by longtime Fool and multiple time past guests on this show, Matt Argersinger, to talk about a subject we rarely touch on Rule Breaker Investing and yet it's such a big and broad subject and could I have a better tour guide? Could you? Then Matt Argersinger so real estate investing next week on Rule Breaker Investing, definitely rubbing my hands together about that one ahead of time. 

Well, before we get started with our nine Rule Breaker Mailbag items, let's do a few hot takes from Twitter from the month that was. Really three to share with you this month. The first one, "Frequent correspondent Jason Moore, @JimminyJilickrz." Love this. "Thank you, Jason." Quote, and he's quoting Matthew Dowd from last week's podcast, 'If you tell the truth, you don't have to have a good memory,' Jason, you wrote @matthewJDowd, dropping one quotable quote after another this week on RBI podcast a focus on conscious politics is the breath of fresh air much needed in today's environment. I highly recommend this week's episode. Thank you. Jason." From an entirely different angle. Meredith K, @MeredithK on Twitter, that means Meredith has probably been on Twitter awhile because there are probably lots of other Meredith Ks who didn't get to be at Meredith K so well-played. Meredith you wrote, "For many years, I took great pride in so-called bargain purchases on clothes, home goods, etc so of the six Rule Breaker's stock trades, the stock having strong past price appreciation still doesn't come naturally to me. But I'm far better than I used to be and actively work on it. Thanks to you." Meredith goes on, "I think of the same 'If you get 25 percent off $1,000, you still spent $750. You didn't save $250' Whether you spent $750 or $1,000," Meredith goes on, "how long will it bring utility and how much utility and joy does it bring matters a lot more both in regards to the stocks and purchases in general." By the way, I think these are good pre-holiday reminders to many of us as well. 

Meredith, you closed that with, "It made me think there should be six Rule Breaker traits for purchases other than stocks and maybe in many other areas, it could be interesting having other hashtag Rule Breakers on @RBI, podcast and various fields to give their rules." Well that's a really lovely thought, Meredith, and we may go there at some point in future. I certainly have sometimes thought of other lists of six that feel Rule Breakery and this could be one of them. Thank you so much for sharing. The last one up, well, it's not just one tweet, it's a few from @Tretter86, Ryan Tretter, who brought much amusement, at least to me, probably to a number of others reading on Twitter in the past week or so, Ryan, you started with this. You wrote, "Sitting in the car with my four-year-old and turned on @RBI podcast and I hear a voice chime in from the back the ughhh," that's ughhh spelled U-G-H-H-H with my interpretation, "not David Gardner. Turn on Mindy and Guy Raz [laughs] who knew she was listening? " Ryan writes @Davidgfool, etc. Jason, you responded. "I got a wide-eyed thank you from my 10-year-old last month when I showed them we're part owners of Roblox and Ryan, you closed out that brief exchange with, I like to think some of what David, his fellow Fools and stellar guests are saying is sinking in a little, as we drive along. My six-year-old son has certainly started asking me questions like, what's a company or can you buy a stock of Minecraft?" You were rolling on the floor laughing at that as I am with you, Ryan, I'm also loving that your four-year-old would rather listen to Mindy and Guy Raz and I totally get that. I'm honored, but I was also just delighted by a tweet you followed on with some days later, you wrote "Had a proud dad moment in the car today with my six-year-old son while listening to David on the Rule Breaker Investing podcast, six-year-old. Dad I want to be an investor when I grow up me, do you know what an investor is? Six-year-old. Yeah, they pick stocks like David Gardner." Well, I am deeply honored, I was the first to point out to you on Twitter, Ryan, that you, ie. the six-year-old's dad is also an investor, is also someone who pick stocks. I think that you are the best investor model for your six-year-old and one day we can get that four-year-old onboard as well. 

But this reminds me to say in closing that one of the life hacks, I think I covered this in a previous episode a few years ago and I share this out with all parents, but especially parents of young kids. One of the better things I did as a parent of three young kids back in the day was to whenever they said something funny, crazy, outrageous, I would immediately timestamp that and copy it down in my smartphone. I would put the exact date and time it was said and what the exchange was said verbatim as best I could remember and boy, have I been loaded up for years now with amazing lines for toast given the graduations, anniversaries, weddings, all kinds of family special moments. Ryan, I'm so glad you wrote those down. I highly encourage all young parents hearing me right now to spend that extra moment and just write it down with the timestamp. Takes two minutes, you'll be so grateful. Save it somewhere where you can find it 18 years later. You will be so grateful you did much hilarity will ensue. Rule Breaker, Mailbag, Item Number 1, we'll, as I mentioned earlier, I've got two guest stars this week, and the first one is my friend Jim Gillies. Jim will be joining me for this. Well, somewhat Jim Gillies story and has taken point to come up, but before we get into this, Jim, let me just first say thank you so much for making your Rule Breaker investing podcasts debut this second.

Jim Gillies: Thank you, David. I think this is the last Fool podcasts for me to come on and I'm a fish out of water in the Rule Breaker ended up on most of the time. This is a thrilling to me.

David Gardner: Well, that's kind of you to say. I think that you are a wonderful Rule Breaker in many ways. We may have overlap in our investing approach and we may have areas of uniqueness, but that would be true of me with almost anybody else on planet earth. Jim, I've so enjoyed your comments, commentary on Motley Fool Live The Morning Show so much that you've done over the last year plus but it's been a lot of years, Jim, when did you get started as a fellow Fool?

Jim Gillies: I think I came officially onboard on Canada day July 1st 2005. But I was a longtime board member and I've subscribed to practically every one of the time, all the newsletters at the time that were Stock Advisor James rule-breaker's side. I've been around longer than that.

David Gardner: That's wonderful. Jim, I'm going to ask you to do something that's unfair to you but would you in approximately 30 seconds explain your life before the Motley Fool and then, I'm prepping you for this, then after we cover that I'm going to ask you for 30-second more in terms of what you're doing today at The Motley Fool. Are you ready to play both games?

Jim Gillies: Sure, let's hit it.

David Gardner: Awesome. Game number 1. Jim Gillies, who were you before 2005?

Jim Gillies: Well David, I was a professional engineer. I have a couple of engineering degrees hanging on the wall which you can't see behind me here. But I specialize in process redesign, civil engineering, environmental engineering but I found my niche working in industry, basically taking all processes that it had, so we say some environmentally dubious impacts and redesigning them, rebuilding them and trying to make the world a better place from that perspective.

David Gardner: That is wonderful Jim and thank you for sharing that. I'm remissing not asking you for 15 seconds more. What was the moment that had you become a Fool? How did that happened?

Jim Gillies: Well David, I am going to admit to a felony here. I did steal the original Motley Fool investment guide. Now, I bought it for my mom, so I stole it from my mom. I knew nothing about investing. Like I said, I was an engineer. I was perfectly happy in my engineering life. I bought the book for my mom because she talked about, ''I want to learn this investing thing as I approach retirement''. She never read it, I stole it from her, I read it in the night. It sounds a little hokey and cheesy, true story, it basically changed the trajectory of my life.

David Gardner: That's amazing. Jim, what do you do at the Motley Fool today?

Jim Gillies: I am the lead advisor for Hidden Gems Canada focused on picking small-caps for Canadian investors. I'm also just analysts at large, advisor at large for all of the other Canadian products as is everyone else here in Fool Canada because we have a lot of products and we have a small team, so we like to be versatile. I'm a stock advisor Canada, dividend investor Canada, micro-cap mission which is obviously our micro-cap offering. I've been in a bunch of other services in the Fool over the years. I'm the small, the unloved often the so called garbage stocks, but it's my niche, so it's good.

David Gardner: Well, one thing we've done well at the Fool over the years and that's about 29 of them at this point is we've hired often the best available athletes and then we ask them as generalists, would you by the way play baseball, also corn hole? Also would you compete in decathlon for us? That's what you do to best available athletes. You just ask them to show up and they do a great job. Jim, I'm delighted to think it's been 16 years and let's not make it 16 more years before you return on Rule Breaker Investing podcast. But that's then, this is now. Rule Breaker Mailbag item number one entitled My Investing Story from W. D. Harris. Tom, my first wealth when I sold my business, WD writes, sold my first stock, Nortel, that's a Canadian company, Jim Gillies you know that.

Jim Gillies: Was a Canadian company.

David Gardner: Good point. Making WD writes 800 percent. Again, We're sharing this mailbag item because it's a remarkable story and Jim is part of the story and that's why I wanted to hear some Jim Gillies' take about the story. Let's continue the story. Sold my second stock, AmeriCredit too soon making 136 percent. W. D. Harris writes, bought more Nortel and held it into bankruptcy after ignoring it 2005. I think We all understand what that date might mean Motley Fool newsletter. He goes on, saved $180,000 working freelance in a profit sharing 401K invested in Berkshire Hathaway. Sold my Berkshire in November 2019 for $189,000 in cash. COVID ended my 40 year career, age 69, unemployed, WD goes on. I joined Stock Advisor Rule Breakers and I built a full IO. That's his way of seeing a portfolio, appreciate that. A full IO of recommendations which soon doubled. Trimmed my full IO to 50 stocks raising $101,000. Jim Gillies said GameStop wasn't dead yet. GameStop was a three legged stool. One, new console cycle, two, Ryan Cohen turnaround, three, over-shorted, short squeeze. Now, I realize Jim, you and I could talk about GameStop but we're really not going to talk too much about GameStop. We have limited time and we're going to focus on this remarkable story. WD goes on nearing the end here, I bought $101,000 GameStop at $4.76 a share before Reddit discovered it. Exited GameStop with $6.5 million, a 50 plus stock full IO, advancing 10 percent compounding by 37 years. I listened daily to Motley Fool Live, to Backstage pass, Rule Breaker Podcasts, Morgan Housel, Adding fuel to winners, Enjoying independence. We are so thankful for this full miracle. Signed W. D. Harris who lists himself as WD Fool and that's with quite a lot of O's. Wow. Jim, I shared this note with you via Slack earlier today. Said love to have you on. You said you knew the story.

Jim Gillies: I did know the story, it was communicated to me before. I have actually talked with Danny Harris a couple of times via email, his related version of the story to me. People say something makes their day or makes their week, the story made my millennium. I certainly did not expect what happened with GameStop to do what it did to the extent. I was pounding the table a little bit internally and our Fool IQ 20 and talking to other analysts at about $5 a share roughly where Danny WD heard this. This is the first time I've learned that Danny is 69 or I guess maybe 70 now so that this is a retirement thing which I am thrilled about, maybe even more. But I know I was talking about GameStop on Motley Fool Live about a year ago at $5. I recommended it in Hidden Gems Canada at $9 to a collective raise sparky and eyebrow like I'm used to.

David Gardner: Jim just to mention, mine was also raised a little bit. GameStop is a former Motley Fool stock advisor recommendation attributed to me because I'm the one who picked it and I'm a lifetime gamer and I've loved my GameStop over the years. But some years ago I decide this is not a company that's going to be that much more relevant going forward, I found myself buying consoles even let alone games on Amazon. I had felt as if the world had passed GameStop by. We're not here to discuss that right now. It's an interesting question but I felt I should put my cards on the table just to show I miss this Jim, I miss this. Back to you responding and thinking about the story.

Jim Gillies: Well, so like I said, I did recommend it at about nine bucks in Hidden Gems Canada. [laughs] It did OK. I will say though that the thesis, which W. D. Harris has, very much got the three-legged stool here. He is correct. That was basically what I was seeing. It didn't hurt that this company was basically $400-$500 million market cap with a reasonable pathway to that amount of money in cash. You aren't paying anything for the business. We did exit David. On the day when GameStop first hit 100 bucks, we did exit from Hidden Gems Canada because the thesis has turned. To my mind, this is not a long-term buy and hold. I have a lot of the reservations that you have about the long-term viability of a retail game platform. I'm excited to see what Ryan Cohen does, but the valuation here is very different, the squeeze is over. When the Reddit crowd came calling, I said I was not expecting to 10x in four months [laughs] on this Company. I feel that the prudent man rule called me to take it off the table for Fools in Gems. I am glad to see that W. D. Harris did also take his millions off the table. I hope he enjoys writing that tax bill, and I think it's a great story. This is further proof that there's always something interesting that you can find in almost every company out there.

David Gardner: Well said, and I really do want to praise what you did Jim, which was to lay out your whole thesis, not just on Motley Fool Live where I think I saw it, but of course for our Motley Fool Canada members before that and you nailed it. I'm here to say I didn't participate, although ironically this is in my portfolio today. One of the things we do at the Fool is we share the tickers that are in our portfolio and that's true of everybody from a techie we just hired yesterday right to the co-founders. You will see some people have seen GME is within my portfolio. That's because it was selected by one of my kids. I encourage my younger now adult kids to speculate from time to time, and so he has speculated. He's actually underwater on his GameStop, but some people might look at that going, "Wait, Dave must love GameStop." No, I don't have much thought about it. I will point out for people who don't follow this stock on a daily basis and those are into it, follow the stock on a daily basis, but it's at 173 even today, so wow. That move from 9-100 is awesome and we'd all take that and it's even higher, but at a $14 billion market cap, I'm not sure Jim, you or I, see the way forward in terms of winning stock from here. It's a meme-stock. It's been picked up with a lot of others. It's an interesting time. I think it's got to be one of the top ten stories of 2021 meme stocks easily. All the places we'll go, you never know who's listening to you or me or what they're doing. Sometimes we wouldn't necessarily do what they're doing or even endorse what they're doing, but when you hear stories like this you got to pinch yourself and say, "Well, in your case, that made your millennium." Now, Jim my obvious reason for inviting you this particularly week was Rule Breaker Mailbag item number 1, but hey, I've got you here and I thought I'd love to hear your comments, Jim, on Rule Breaker Mailbag item number 2, so will you hang with me five minutes more?

Jim Gillies: Absolutely.

David Gardner: Excellent. This one comes from Joel Jones. "Dear spiffy-pop," he writes, "I'm a 37-year-old ear, nose, and throat surgeon with an MBA and economics degree. I went to my farther for investing advice," Joel writes, "and he told me, 'The stock market is just professionalized gambling,'" exclamation point, "and sent me to his financial advisor who recommended some index funds he had sold my dad with a five percent load fee." Now, pause it there for a sec. Many of our listeners may not even remember or think much about loads these days. It's not as cool or prevalent as it once was, but let's be clear the five percent load fee is a five percent upfront sales cost that you're paying and you're basically just paying that to the manager to sell you the fund to congratulate him or her that they got you to buy their fund. Five percent of your assets gone off the top before you start getting invested, which is why the Motley Fool for many years, a champion of index funds I'm happy to say we are, has never liked load funds. Anyway, we're going to return to Joel's note here. He said, "He'd sold my dad with a five percent load fee and high expense ratio. Something seemed rotten in the state of Denmark. Despite my background, I really had no investing experience. Real knowledge," Joel writes, "is gained outside the classroom. Ironically, I signed up for the Motley Fool service one night while I was at a casino using the money I won at blackjack to buy stock advisors," so many people, so many stories. I love it. Joel closes, "I love your service, investing philosophy, and company culture. Why is it that investing literacy is so poor? It seems like many financial advisors are consciously or subconsciously hoodwinking us when they can't beat a low-cost S&P fund. Like Neo in The Matrix, I have taken the red pill. Given the evolution in the information age and online services like The Motley Fool, will we one day see a majority of us individual investors and the death of retail advisors? Cheers." Joel Jones, 37-year-old, ear, nose, and throat surgeon, Jim, with an MBA and an economics degree.

Jim Gillies: This is beautiful because it allows me to dovetail right into a personal story. By the way Joel, when you ask a majority of individual investors and the death of retail advisors, I say from your lips to God's ears. [laughs] My significant other, let's call her Lulu as in the Lululemon ticker because that's her name. When I met Lulu now Lulu is a professional, she's a chartered accountant. She has a master's degree in accounting. I want to emphasize that this is not a financially stupid individual quite obviously. They don't hand out those degrees if you can't add two and two and get the same number every time.

David Gardner: True that.

Jim Gillies: We each had our own starter marriages to be ready for each other, and so when I met her, she is a chartered accountant, extraordinarily financially disciplined.

Jim Gillies: She had every paycheck paid herself off-the-top going to one of these retail advisors who had saddled Her with a host of really crappy mutual funds, no five percent front-end loads thankfully, but there were a number of back-end loads, that is, you have to pay to put your money in, you get sucked on the tail end, when you take your money out, unless you're in a problem.

David Gardner: Don't let the door hit you on the way out dear individual investor.

Jim Gillies: Just seven-plus years. She had been extraordinarily disciplined for the decade before I met Her. Every paycheck going into this thing. When I met Her, she barely had the amount of money that she had contributed. She had back-end loads. I said, well, I can't predict the future. I don't know how long our relationship would last. But I can teach you all you need to know for investing. If you don't catch the bug and you don't love it like we do, I can teach you what you need to know, that we break up tomorrow, you are set for life. She's like, "Okay, those are big words buddy, let's go." I introduced Her to the concept of Index Funds. She is already doing the right things, she's already got the discipline. We pulled everything out of where she was, we got rid of all those terrible mutual funds, we paid the back-end load. She was a little reticent a little, but I said, "No, trust me, this is for the best." Nine years later almost, [laughs] I guess I didn't need to teach Her anything. But we didn't know. Nine years later, Her account is up. She's always had this discipline because she doesn't love investing. She just wants to get a market return and that's fine with Her. She values comfort security more than finding latest Rule Breaker or the latest insane stock from me. She is quite happy with that. Her portfolio has done excellent, frankly, over the past little while. We did this, I think in 2013. Importantly, she hasn't needed me. To me that's great because, again, I could be gone tomorrow, fatal bus accident, she'll still golden for the rest of Her life and we're even at a no cost to zero-cost broker now. You are correct, Joel, that something was indeed rotten in the State of Denmark. I actually think the world needs more, even if we're just helping fools at a level like what Lulu does, which is just Index funds and nothing more. 

I think that's great. I would much rather see someone paying ten basis points to 15 basis points on an S&P 500 Index Fund. Knowing that you have exposure to all of the great companies in the S&P 500, just go with that. Dollar cost averaging into that for two and three decades, you will be fine, but I don't think there's enough of even just that out there. I know I've certainly talked to a number of friends, family, neighbors, and it's the same stuff I always talk about. Index funds first, learn about what the stock market is, learn about the basics of investing. I've got a good friend from almost 40 years now, which dates me a little bit. He's a high school vice principal. He just started, we've just gotten started this summer in Index fund investing. I gave them Morgan Housel's book, I encouraged him to pickup Joel Greenblatt's little book that beats the market. He's devoured both of those. I think we might have a budding fool on our hands later David. But even if we don't, I know He is going to be fine for the rest of his life and I think that's a good thing.

David Gardner: Well, I thank you for sharing that story Jim. It reminds me, this is very true of you and I think a number of others that we know as fellow Fools. You can't not want to spread some financial literacy. I mean, you've got friends, family, you've got people that you are co-workers. How could you not want to save them a 5 percent load on their l account or help them understand the financial literacy that they miss. One of the learnings that we've had so far from the Motley Fool Foundation, Jim, which is certainly going to be looking at some of this and trying to fix some of this, is that the reason there's not more financial literacy in our US schools, I assume the same is true in Canada, but I never should, because I like some of the aspects of the Canadian education system are truly outstanding and we envy them. But I will just say that the reason we don't have more financial literacy at lower levels, like get kids start early, is because we don't have enough teachers that have confidence themselves that they can teach it and teach it well. The sad truth is, the reason it's not taught to our kids is because there aren't enough teachers who know it well enough. That's the say nothing Jim of Chartered Financial accountants or ear, nose and throat surgeons with MBAs.

Jim Gillies: That's the remarkable thing to me. Information almost sometimes in your coursework as Silo. She is a great accountant, she is the Chief money person for a local business, smart one, one city over. But she is the authority. She came through school with a financial leaning, with no investing. Investing financial knowledge because it simply wasn't taught. That is tragic to me because she is smart, dedicated, diligent, disciplined. I'm hitting all of the D words apparently, [laughs] and yet didn't have the knowledge. Yes, it was out there, she looked for The Motley Fool stuff, but she trusted someone. I don't even know who it was, who said, No, you need a professional retail advisor, like a financial advisor. This is too complicated for you to do yourself. Just what I've said earlier, David, is the ability just to dollar-cost average in the Index funds and do nothing else? Just as you're investing base. That is a 15 minute conversation at most.

David Gardner: What a valuable one that is for those who have it. We're going to try to reach many more. This podcasts is one small example of The Motley Fool writ large, is a much larger example. I'm looking forward to reaching more and more people. I will say Jim, one of the pet peeves I shared on my Volume 6 of my Pet Peeves last month is the phrase retail investor. I've just never liked that phrase and it usually comes from the industry that's selling stuff to us, so we're retail investors to them. I think of myself as an individual investor and I love that vision from Joel that maybe one day, yes, maybe from his lips to God's ears, as you said, Jim, maybe there will one day be more individual investors than financial advisors who might be taking advantage of so-called retail investors. Well Jim, it was a delight to have you on this week's Rule Breaker Investing podcast. Thank you so much for your perspective. Let's do it again sometime soon.

Jim Gillies: Thank you very much, David, and look forward to it.

David Gardner: Rule Breaker, Mailbag, Item Number 3, this one from Wim Michelson. I hope I pronounced your name correctly. Wim thank you. Hi, David. I started investing in the stock market the full way only since December last year. A whole new world has opened for me and I'm excited to finally find a way to invest in individual stocks that I feel comfortable with. I feel much better compared to investing in mutual funds, which felt to me much more like a black box. Thank you, Motley Fool. Now, before I continue onto Wim's actual question, I just want to point out, Jim and I just talked about mutual funds and I think they're a great answer, especially Index funds, especially ones where I know what's being indexed. I'm highly suggesting that anybody listening to me right now who favors funds or ETFs has clarity about what exactly they are investing in. Because if not, mutual funds are much more of a black box than investing directly in individual stocks where you know the companies that you're invested in. I really appreciate that point where I'm especially coming right after that conversation Jim and I had about funds. Anyway, back to your question. You said, "I do have some question which might be interesting for the podcast of which I am a big fan. I have built up a 35-plus portfolio, 35-plus stocks of Stock Advisor and Rule Breaker recommendation starter stocks and best buys over the past ten months." I would say you Sir are following best practices, that sounds great to me. "The problem I see for myself Wim goes on, is how to keep my portfolio within limits. There are so many great recommendations and interesting companies. I've sometimes skipped investing in some recommendations because I didn't want my portfolio to get too big.

Of course, some of these stocks would then start to beat the market big time. My luck again." Wim writes. In closing, "How to keep my portfolio size under control? Don't visit the Fool website anymore for a couple of months?" He's laughing at the end of that one Fool-on, Wim Michelson. Well, when you've asked one of the timeless questions that gets asked and reasked, if not every month on mailbag then every other month. It's only a few times a year I go back to this one because I could answer and reanswer this question every month. It's frequently asked. As a consequence of that, for frequently asked questions, I've tried to build up answers that I can point back to so you can hear past answers to all repeated questions. You just got started the Fool way you mentioned last December. Let me mention two resources to you that I think can be helpful. The first is that a few times on this podcast over the years, I've talked about how to manage any number of stocks. Whether you have 14 stocks or 140 stocks, I think the answer is the same. I did this long enough ago. I can't even remember the first podcast to have done this, but I can at least tell you that one of the series I do on Rule Breaker Investing is called Old, New, Borrowed and Blue. That episodic series, let me bring you four points each time and one of them is old. That's the first one. Something that I've already said before. The date was April 5th, 2017. It was Old, New, Borrowed, Blue volume 1. I highly suggest that you listen to my old point about how to follow any number of stocks and make your portfolio reflect your best vision for our future. I hope you'll be able to Google that and find that and listen to it. It's not long, but it speaks to how you should give some stocks overtime, extra time to follow, some, regular time, and some, downtime. It's a framework anybody can use. 

Again, this is one of those points that's recurred and I try to speak back to it from time-to-time. That's answer number 1 for me. Answer number 2, earlier this year, I laid down the list to Meredith K's point, a new list of six Rule Breaker principles. It was an important podcast, I think. The date was January 13th. It was a new year's gift, if you will, to the world, to my listeners. It was called: 6 Principles of the Rule Breaker Portfolio. I highly suggest you listen to that and think about principle number 4 regarding your sleep number. This was of course not just for when, this is for anybody with the recurring question, what's the right number of stocks in my portfolio? By the way, there is no specifically correct answer to that question. It's different strokes for different folks, but I'm trying to speak to all of the folks and all of the strokes with those answers. Thank you for your question, Win. Rule Breaker, mailbag, item number 4. Now, sometimes for mailbag I'll get a note this month, but it was actually reacting sometimes quite frequently to one from the previous month because notes come in. People think about them than they write us. It's off by a month. But I opened up September with, "I Fought the Law and the Law Won. That generated me some good notes including Greg Rowe." Thank you for this. Greg, David and crew, "I enjoyed the recent show on this topic: I Fought the Law and the Law Won." Now, for those who didn't hear it, I'm just adding that it was about laws, things like better law, which I've mentioned a couple of times today, Parkinson's Law. 

Often laws around human behavior that really do for me anyway, rise to the Law. That was the focus that if you try to fight the law, the law is probably going to win because these are human traits deeply embedded in us. That was the point of I fought the law and the law won. I encourage people to write out with some more of theirs and their reflections and that's exactly what Greg has done here. You said, "I listen to show each week along with Motley Fool Money on Fridays. I'm a Rule Breaker and Stock Advisor member. I wanted to share a few of my own for my time in the navy and on the joint staff." There are two that he shares. The first is, he who plans early plans twice. He said that's associated both with Parkinson's Law and our tip from October on inactivity sometimes greater than signed activity. He goes on the military, rarely lets idle time sit idle. Often you will find your time is filled planning for potential scenarios and yet when the actual scenario arises, Greg writes, you don't dust off the plan you made, but rather make a new one. There is utility in the mental exercise of planning for this scenario. But often it feels like make work since you know it won't be used. Now I see, Greg, you were a Notre Dame man. I see in addition to being a navy man, I think of all the great Notre Dame Football greats and I bet they had some great aphorisms too. Anyway, I like this one. He who plans early plans twice. You've beautifully illustrated that. I know many of our military listeners, some of them anyway, are nodding their head in agreement right now as I share your wisdom. 

By the way, it's not my wisdom, it's Greg's. I always hasten to add on our mailbag episodes. So much of this is just me channeling the wisdom of so many Fools around the world. It's a delight to bring you these kinds of insights from people who have so much more to share than I do. That's why I love mailbag. Let's go to Greg's number 2. He writes, here's another one. "If you wanted bad, you'll get it bad." That is, our correspondent writes, "On due urgency to meet a deadline is inversely related to the quality of the decision or product." By nature, Greg Rowe writes, "The military deals with emergent issues that need decisions in a tight time-frame to impact the outcomes and sometimes that's unavoidable. However, often, staffing processes drive poor solutions by not allowing for full vetting of issues and the outcomes are "sub-optimal." Somewhat related to the last one point number 1, in that you can attempt to plan early, but you can never predict the uniqueness of situations and then narrower range of options you may be left with. Greg Rowe closes, "While the nature of the military is certainly different than businesses, motive for profit, or example, mission assurance and redundancy are more important than efficiency. These lessons from working on a staff may also apply to business as well." Fool on Greg. Greg, you bet those apply to business. I think a lot of us learned at least a thing or two from your mailbag item this month. Thank you for sharing. Rule Breaker Mailbag item number 5. Tony Locker Atondo, thank you very much for this note.

Tony reacting to our mental tips, tricks and life hacks from this month's episode. "David/team, I was listening to your episode, tips, tricks, life hacks about how inactivity is rarely better than activity except investing. Have two examples that I relate to as an emergency medicine physician and resident/student educator." Tony adds, rugby player. One. "Sometimes in medicine, it's important not to act too quickly or overreact as you can cause harm with knee-jerk reactions." Well, gee, Tony, that one makes a lot of sense to me. He goes on to add, "Law 13, this is from Samuel Shem, The House of God. "The delivery of medical care is to do as much nothing as possible." Love that. You do add here. "In emergency medicine, you sometimes have to think and act quickly but it's important to know when inactivity is more important than activity." I think all of us have ever been to the ER. Well, anyway, the general appreciation we have for people on the frontlines, but especially, the emergency medical physicians, thank you for your service, sir. I really do appreciate that point about inactivity being so powerful in that context. The second one you share, you say, "When you become good at a sport, I think we're headed to rugby here, it may look like you're playing effortlessly," Tony writes. "With little extra activity, work smarter, not harder is the mantra." Tony shares, "I end up in more plays and creating more benefit to the team, not because I run around so much like in my younger days, but because I know where the play will be and I put myself there letting the play come to me." Hope you find these interesting, even if they may not be podcast worthy. Very respectfully, Tony Locratonda clearly Tony, they were DOMAJMC in emergency medicine. 

Those were certainly podcast worthy. I want to tack on to Tony's another note I received from Bruce Bally. Bruce also led off with medicine. He mentioned Hippocrates first do no harm. I hear you there. Bruce also added, he said second, "When I was a young whipper-snapper, my mother drilled into me and I expect yours did too." He says. "If you don't have anything nice to say about him or her, don't say anything at all." Those are three great examples of where indeed inactivity greater than sign activity, it's not just investing. But boy, if Rule Breaker Investing doesn't stand here firmly letting everybody hearing me right now know that inactivity greater than activity is so very true of how you handle your money as an investor. Anyway, thank you gentlemen for those notes. Rule Breaker Mailbag, item number 6, this one comes from Brandon. Brandon, thank you for this note from a fellow Fool and Rule Breaker. Brandon writes, "Dear David, I couldn't help but reach out to you after listening to your tips and tricks podcast this month. I was especially intrigued by your tip about building community at church by having people tell their stories. My current church," Brandon writes, "has struggled to build a strong community. I often feel disconnected from other members since few really know much about me." On a side note, I think that's sad and I'm glad you're writing, Brandon, and I hope they'll get to know you better and it's true if you too as you get to know them better. Anyway, continuing on, you said that, "I love this concept of sharing stories for 15 minutes before church. I would gladly share with others and would love to hear others' stories as well, yet I doubt it would work in our church. I've lived in the Midwest my whole life and currently live in a suburb of Minneapolis. 

Culturally, most Midwesterners are not very forthcoming. Indirect communication and passive aggressiveness are very common. Family and friend units can feel very closed off to outsiders or transplants as I am." Brandon wrote, "I grew up in Wisconsin. I have a hard time," he continues, "imagining people being vulnerable enough to share much of themselves in the form of their stories. Problems persisting for decades and across generations is quite normal. Passive aggressiveness does not lead to good conflict resolution or problem solving. Everyone knows the problem," Brandon writes, "but no one wants to talk about it. As a Rule Breaker myself, I tend to be fairly direct and forthcoming. Since I'm a natural problem solver, it often puts me at odds with those within my family, work, and church. I'm very curious about your thoughts on how to build community and a strong culture when vulnerability and openness are essentially countercultural. On a side note, I'm fascinated by all the great Minnesota companies, 3M, The Toro Company, Target, Ecolab, Best Buy, etc. I'm curious how they deal with the different cultural dynamics of the Midwest and how that affects innovation and problem solving." Signed, fellow Fool and Rule-Breaker Brandon Gerac. I was saying offline beforehand to my producer, Rick, I don't know that I have a great answer to this one. It was more just that I wanted to share that in the first place because I bet someone's going to write in with a great thought for you in future, Brandon, and while it's not totally within the purview of Rule Breaker Investing to go there, one-third of this podcast is about life and I love thinking about these things. I guess I have two quick thoughts for you. The first is that old line misattributed to Gandhi. 

Gandhi never said this. I know you've seen it on bumper stickers. I know it's there in TED Talks. Gandhi, check it, never actually said, "Be the change you want to see in the world." But regardless of who said it is a beautiful sentiment, it sounds of Gandhi. I think it's probably applicable here. I think, Brandon, if you simply authentically be who you are in the context of family, work, and/or church, and show vulnerability and share parts of your story at the right moment with the right group of people, I think that's probably the best I could think to do in most circumstances. Quick answer number 1 is be the change, and then a quick answer number 2, because I'm all about talking both sides of my mouth and trying to see 360 degrees around things, I'd be the first to say you need to do it at the appropriate moment in an appropriate context. I don't think you can show up from out of the blue, totally outside of other people in the room, totally outside their experience, and just hit them sideways with what you think they need to hear. I think the best thing you can do is get to know them, hear their stories, and then speak into that at the right moment, being the change that you want to see in that group. But I don't think you can show up, for example, let's have fun here with an electric blue mohawk haircut in an Amish meeting and say, hey, we need to loosen up a little bit more in this community. You might be right. I have nothing to say for against the Amish in this context, I'm having fun, but you can see what a fish out of water you would be trying to be the change. So I think you need to get to know a group of people. Isn't that the story of the movie, Dances with Wolves? Don't I remember that having seen it a couple of decades ago? Doesn't Kevin Costner's character take the time to get to know the native Americans that live within their culture before he can make a real contribution? 

Side note, I tried to bring that movie to movie night with our kids when they were teenagers some years ago and I made a tragic mistake. Turns out there are two versions of Dances with Wolves. There's the one I saw in the theater back in the day the year it came out, and then there's Dances with Wolves uncut, the long version with approximately, this is my call, 45 minutes of additional footage that is largely pictures from nature. That's right. If you want to see herds march across the American West, supposedly back in the 19th century, boy, is that version for you. Our family had to quit at about the two-hour point when I started asking, "What happened to the movie that I saw?" I realized, oh my gosh, I've just put my kids through half an hour of watching with beautiful musical accompaniment but no plot progression. A lot of wildlife. Maybe I clicked the wrong version on my Netflix queue back when we used to order DVDs. Anyway, there's a life hack for anybody, Dances with Wolves. But Brandon, I hope that's been helpful. I think we all need to have a little dances with wolves in us as we get to know our community and try to improve it. I love where your note came from. Thank you for sharing. Rule Breaker Mailbag, item number 7, lucky seven. Thank you, Colin Shannon. I am going to give you her Twitter handle, and it will become increasingly clear why I'm doing that @colin_shannon. Thank you for this note. "Rule Breakers Investing," Colin writes, "I hope you're doing well. My submission to the mailbag is not an investing question but a question that is to cure my own curiosity. Couple of months ago, I received a notification saying that David Gardner has followed me on Twitter. 

Now, being a young investor, 23 years old, who started during the pandemic and has been listening to The Motley Fool's podcasts faithfully since then, I was shocked to see that David Gardner had followed me. I figured that you must follow tens of thousands of people as some influencers do, but I quickly realized that I was one of the 470 people you follow. I figured it must be an accident and will be quickly remedied when a tweet or retweet of mine," Colin writes, "comes across your timeline, but it's been a couple of months and the David Gardner profile still says 'follows you.' Maybe you noticed that I work in college basketball, so you followed me out of your love of sports. Maybe my meager amount of tweets and retweets on life, politics, and investing hit a Twitter niche that you were interested in, or maybe love this phrase here, you're an educated man, or maybe Occam's razor applies, and the simplest explanation is true that I liked one of your tweets and you accidentally followed me. I write this mailbag submission with the knowledge this could lose me the Twitter follow if Occam's razor applies, but my curiosity made me ask, why did you follow me on Twitter?" Signed, Colin Shannon or as we usually say once again, @colin_shannon, spelled Colin and Shannon as English native speakers would expect. 

In this brief response, let me first encourage anybody else to follow @colin_shannon. I see Colin you're at about 300 followers right now, I hope that we can get you to at least 320 based on anybody hearing me right now, a lot of us do use or appreciate Twitter. I'm going to say, please follow @colin_shannon so we can further confuse this delightful 23-year-old. Colin, I don't exactly remember, other than when somebody says something interesting or funny, I often will click and see who they are. I saw from your profile that you are a basketball graduate assistant at Oakland University. Now, I don't know Oakland University that well, although I do believe this is the one in Michigan which will confuse a fair number of people. But Colin, I'm thinking a combination of a couple of things. First of all, you said something capital F, Foolish, you're connected in, you're a Motley Fool fan. I like that. Second, college basketball, check. I like that. Third, you just used Occam's razor in your note to me. Anybody who can rock Occam's razor, college basketball, and Foolishes gets my follow. I don't remember exactly what the instinct is, but here's one commitment I can make to you, Colin, I am never going to unfollow you on Twitter unless you try to make me for some good reason. Thanks for the note. Rule Breaker Mailbag items number 8 and 9, I mentioned at that top my friend, Aaron Bush, joining us again this week. Aaron, a delight to have you.

Aaron Bush: Thanks for having me, David.

David Gardner: You are very welcome, Aaron. We're going to talk a little bit about that at the end, but that's Rule Breaker Mailbag, item number 9, let's start with the real reason I thought, let's have Aaron on this week because we're talking some crypto here with Rule Breaker Mailbag, item number 8. This comes from Arvind Sharma who wrote a really nice note that I'm not even reading. But I'm going to read this part, "David, thank you for inviting Aaron and John Rotonti. It was nice to hear their views on inflation, crypto, and its role in the economy." Pretty sure Arvind is reacting to last month's mailbag with Aaron and I and John talked about crypto among other things. "Thank you," says Arvind. "After hearing Aaron's comments on cryptocurrency to use to interact with the community built distributed networks to serve a purpose or address a problem," Arvind writes, "I was thinking about one similar concept, open source codes. Open source codes are designed and developed, maintained," Arvind writes, "by the community. For example, the world-famous operating system of my days, Linux, was designed and built and supported by the community. It was FREE. So is it fair to say if Linux were to be built today in the crypto blockchain world, Aaron, it could be designed in a way where those who contribute to building this capability might be rewarded with, let us say, Linux cryptos? Those who would use Linux, would they need now to pay using Linux cryptocurrency?" Arvind says, "I'm using Linux as just an example. I understand it's designed to be free." In closing, I understand crypto and blockchain versus open sources, may be comparing apples to oranges. My brother, Tom Gardner, has always wittily pointed out that they're both fruits. Anyway, having said that for a novice like me, Arvind ask, "Does this Linux example give us an easy way to explain or think about cryptos? Curious to know your team's thoughts." Thank you rights, Arvind. Now, I maybe have some thoughts, but whatever my thoughts are, I subvert them to my pal, Aaron, who's graciously hopped off of his horse. Aaron lives in Texas now. Aaron, obviously you have a horse.

Aaron Bush: Obviously.

David Gardner: You just hopped off your horse to join the podcast and contribute some thoughts back to Arvind, and anybody else who's wondering, Aaron Bush, what about open source software and the idea that intellectual property can be compartmentalized into a cryptocurrency? What are your thoughts in that direction?

Aaron Bush: I look forward to hearing your thoughts on this too, David. But Arvind, I think that's a great observation and great thinking. Here is I think about it, and I think to look forward, we almost need to take a step back and look in the past too. The first wave of the Internet was really about building the protocols in the software that everything runs on. Linux is part of that era, but also projects like Hypertext Transfer Protocol, HTTP, the File Transfer Protocol, FTP, which is the backbone of the Internet, the Domain Name System, which is DNS and there's so many more. These are increasingly known as thin protocols. Tremendous work to develop them led to an enormous value creation, but the protocols themselves and the people who worked on them, essentially captured zero of that value. The second wave of the Internet was the permissionless innovation that those protocols enabled. Individuals and companies of all types took those protocols and used them to build great experiences. There are too many examples to name, but much of The Motley Fool stock-picking success over the past 25 years, for example, has come from intelligently riding that wave. Companies like, Amazon and Netflix and Booking and Salesforce and even the Motley Fool itself, created value for a lot of people by leveraging those open protocols built in the early days of the Internet, and then capturing much of that value through building corporations.

David Gardner: I lived through in creative part of that history, but it took Aaron to actually put it into the context of history to understand what the heck has been happening around Fool HQ for 29 years. Wow, Aaron, thanks. Keep going.

Aaron Bush: Sure. For the most part, that success of that second wave of the Internet has been a hugely positive force for humanity. I don't see that going away, but it's also not perfect. It's not the only answer to every problem, and it's not the only path of innovation. For example, we see social media companies are entangled in censorship issues. Financial companies are not necessarily open to all types of people. Creators and entrepreneurs are increasingly beholding to platforms that can change the rules at anytime and often take larger fees and sometimes they're worse than a lot of the value created today is mostly captured by ever larger and more centralized and more regulated entities, which by effect also stifles innovation to some degree. Although, companies which built on those protocols can be amazing forces for good and create lots of value, they're not perfect and they're not the only answer. Which is what has led to the third wave of the Internet, increasingly known as Web 3 today, which is in some ways going back to the early roots of the Internet with the ethos of openness, trustlessness, and permissionless innovation, and participation again, but in a way, where the value is captured in a more decentralized user-friendly way. Crypto is one piece of Web 3 and these new protocols like Bitcoin, Ethereum, and others are now occasionally called fat protocols in contrast to the thin protocols that I mentioned of old. This way, the protocols not only are digital infrastructure, but are owned, and governed, and operated through being tokenized. These tokens don't just create ecosystems but economies around these protocols. Those who contribute to these protocols, the development of the next phase of the Internet, actually capture that value, and it enables people to work together and create and capture value in more decentralized ways. In many ways, it also enables users and creators to retain more value in new ways too. 

Plus, the financial element creates incentives, which is why there's so many people innovating in this space today. It's still very early, but it's so fascinating to watch everything unfold and there are real success stories emerging. The last thing I'll say is that, there is much more to Web 3 than crypto and Internet money, but it is important, because these tokens, not only are the means by which digital goods and services are paid for, but they're the means by which people get paid for contributing to these open networks. The means by which groups of anonymous and decentralized people all around the world decide how to work together and decide on the future of these projects. It's the means by which security, in some cases works, and much more. It's very complex in the same way that the early Internet was complex. But really in short, it set the foundation for people to come together and work on and participate in big important projects and new ways. These aren't corporations or LLCs, they're something new, but maybe, just as if not more important in the digital world. As time goes on, I think everything will become more user-friendly and more intuitive, but we're at an exciting time. Really just to wrap that up, Arvind, I think your observation is spot on. Not all software needs to be tokenized and turned into some type of crypto platform, but it definitely has a role for taking the Internet to its next stage of evolution, which is very exciting.

David Gardner: Absolutely brilliant, Aaron. Thank you for that. Cogent explanation, it's reminding me, sometime in the New Year, park yourself a week, where I'd love to have you on, and let's just feature non-fungible tokens for one week of the Rule Breaker Investing podcast. I'm very interested in this. There seems some crazy bluster, but when you look through the smoke, some very real stuff happening. You're great at often seeing the signal and helping us ignore the noise. I think there's a lot of noise in NFTs, non-fungible tokens, but a lot of us hearing me right now, know more about that than I do. Maybe not as much as Aaron, but more. A lot of us don't yet know what the heck NFT stands for or why you and I should care. Aaron, I tend to plan this podcast at about 10 weeks in advance so I already know what I'm doing into January, but would you be willing to come back in January and let's talk in the New Year about NFTs?

Aaron Bush: Of course, let's do it. That'll be fun.

David Gardner: Awesome. Well, before then, let's spend one more mailbag item together. Here we go, closing the show this week. Arguably, from the sublime to the ridiculous we'll see, it's a phrase I often find myself using, because I like to live in both places here on Rule Breaker Investing podcast and at the Fool, write the sublime and the ridiculous. Let's go to Rule Breaker mailbag item number 9. Now I'm going to hasten to add that this note is not at all ridiculous. It's ridiculous that I would have featured something on this show that would have me reading this note back. Any ridiculousness and I'm not going to apologize for it, because I love it is from me. Thank you, Riley Herrimann for this note. Hey, David, while listening to your podcast about pet peeves, I was surprised to hear that you thought, you're welcome was the proper response to a thank you, and saw response, no problem, as potentially inappropriate. Now, I need to pause this for a second, just remind this was from our Pet Peeves podcast last month. I've already referenced this a few times. I don't want to air this Pet Peeve again, Aaron, but we're going to get to your thoughts very quickly. When I say thank you, I love it when somebody says you're welcome. When somebody goes, "No problem." I'm like. Well, first of all, I didn't think I was creating a problem. I was just trying to thank you. No problem has always felt like a wet prickly to me, like a wet willy, like your obnoxious uncle licks their finger and sticks it in your ear. It's a little bit more like that. No problem, or no worries, where I want to say to the person, "I wasn't worrying at all, you thought I was worrying? I was just trying to thank you." Anyway, that's what we're talking about here and what Riley's reacting to. I really love this. 

This is a note from a college student, it continues, "As a college student, I almost religiously say no problem in response to thank you, as I feel almost rude saying, you're welcome. A quick internet search" Riley writes, "shows it's a linguistic issue". I love this because Riley goes on to say that Riley asked their linguistics professor at college. I think this is Wake Forest University if I'm seeing this right. She said, "This professor says while older generations say you're welcome because they see the act of helping as something that's out of the way and not expected. Your generation, this professor says to Riley, often uses no problem because the act of helping is a given, and you don't want the receiver of that help to feel guilty or obligated to return a favor." Now that does seem to be an important point here, Aaron, as we're about to open this up because you and I are different generations Aaron, we're going to talk about this. "I don't think either is wrong," Riley concludes, "necessarily. I actually think it's interesting and funny however that baby boomers," by the way, I'm not a baby boomer. But anyway, "that baby boomers tend to feel disrespected by no problem or no worries. On behalf of my whole generation trying to clarify, no problem. Love your podcast and your service, best, Riley Herrimann." Well, I guess I could almost restate once again what I think, but I think I've already done that enough. Aaron, what is your reaction to Riley's note?

Aaron Bush: I can't say that I've ever thought about this before. [laughs] But I understand, I guess as I'm thinking about this, [laughs] no problem in my sphere has often been more casual and friendly while you're welcome is much more formal. So if you're hanging out with a friend and they grab you something, you say thank you and they say you're welcome, [laughs] it maybe can be interpreted as maybe there's a little bit of angst behind that comment and maybe they're not as welcome as you would want them to be. I think Riley might be right in saying that no problem is a way to remove any social indebtedness from the situation. I feel it's so commonly said though that I don't think anyone really thinks about that when they say it, but I think that is a valid observation.

David Gardner: I think that that is important what you've said and what Riley has pointed out, and admirable as well, because we don't want people to feel beholden. I see the instinct there. I guess I want to say, even though I'm not a baby boomer, I will admit I grew up as a little kid at the age of nine, well I went to a private school, but I literally wore a jacket and tie to every day of classes in elementary school. So thank you and you're welcome was probably a little bit more formal and just felt natural. One of my favorite responses when I say thank you to someone is you're so welcome. That's more of a southernism I think, but it's always made me feel warm inside. But It might make others feel obligated. I'm glad we're talking about this, even though arguably no one should still be listening to this podcast at this point this week. But it does remind me Aaron, of a different texting protocol that I bet you're familiar with, but I discovered with my kids. From day one when AOL Chat Rooms showed up about 25 years ago, I always have tried to perfectly punctuate anything that I'm saying to somebody in a live chat, I still do it on Zoom chats or anybody else's live streaming chat if I'm typing something. If I texted you, my pal, my friend, my friend Aaron, my son Gabe, my wife's dad, it doesn't matter. I'm always fully punctuating things. But is this true, Aaron, my understanding of those approximately 25-years, which I define as the length of a generation, approximately 25 years younger than I am. If you put a period on the end of a sentence via text, that's a huge point. I mean, it's a tiny little point, but it's a huge point. Is that right?

Aaron Bush: I think so. It's not necessarily a positive tone, it's a very serious tone. My generation, we overuse exclamation marks.

David Gardner: Okay. We all have our foibles and we all have our unique cultural identities. I'm the first to say, I don't love generalization. Earlier in the show we generalized, thanks to one of my correspondence, about the Midwest. A lot of people in the Midwest might say, "That's not actually how it is in my part of the Midwest." But a lot of other people might say, "Well that's a fair generalization about Midwesterners." Well we're generalizing right now about generations, which yes, up to a certain point works, but I'm the first to start rebelling. If we start expecting every baby boomer to think this or every Gen X or Gen Y or Z to say that. It's over winning at that point. Do you agree?

Aaron Bush: I think so. I would just say that I have a feeling most people do not think about it to this degree. [laughs] Part of why I love coming on and just talking about these crazy topics is because David, you just make me think about words and language so much more than I would otherwise. It's just a fun conversation.

David Gardner: Well I appreciate that Aaron. I will close by saying that we had a brief talk about the phrase wing it because for me, I have a national holiday, well it's just my own personal holiday, every year. October 24th where I encouraged myself and anybody else to wing it sometimes in life. I have a story attached to that, and if you follow me on Twitter you would've seen that on October 24th, which was Sunday of this past week because that's wing it day for me. But more importantly, where did the phrase, I start wondering, wing it come from? As it turns out, it comes from the theater. You know I love words and phrases and etymologies. It came from, I think the first use was around 1885 if I saw it right. It was somebody waiting in the wings as an actor who needed to somehow intervene on stage because something's gone wrong, or maybe they're the understudy. Whatever it is, they're determining quickly in the wings what they're about to pop up on stage to do. They are winging it. I'm glad we used the phrase wing it to close so I could share that. But yeah, I do think Aaron, that so much of our individual mindset is in fact revealed through the language that we, I was going to say choose to use, but I will say use. Not all of us are that intentional, nor am I, with every single thing said. But some of my biggest breakthroughs as a Rule Breaker is noticing that everybody is using this or that phrase in finance and I think they're getting it wrong or they don't know the history of that. We've talked about the word investing and investeries as an example, we're not going to do that. But anyway, Aaron, thank you for appreciating that about me, I think that we can all do it. It's not like I was a major in etymology. Well I was an English major, but not etymology, but we can all find out the origins of things and learn something from that. Aaron, you've done a great job thinking about the origin of very recent things that are very powerful over the next 30-100 years. Thank you so much for your insights, not just on cryptocurrency, but of course, lots of Rule Breaker insights over the years. I'm looking forward already to January.

Aaron Bush: I don't know whether to say no problem or you're welcome back, but I'll just say, it's always a pleasure to be on David. I always look forward to these Foolish conversations.

David Gardner: Thank you, Aaron Bush, and thanks to everybody for staying with us all hour-ish long this week for the October Mailbag for Rule Breaker Investing. We hope you have a great week ahead. I want to mention that Matt Argersinger is joining us next week to talk real estate investing, something we've really not done much. I remember earlier this year I had Ollen Douglass on to talk about venture capital investing. Investing takes many forms. Admittedly, common stocks tends to dominate my own time, but I want to always be sharing out other forms of investing and boy, did Ollen do a great job with venture capital investing. Will Matthew do a great job next week with real estate investing? Writ large and writ foolishly only next week on Rule Breaker Investing. Again, thanks to my guests, Aaron Bush and Jim Gillies, and as always, my producer, Rick Engdahl. Have a great week ahead, Fool on!



This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.