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Cool Stuff Under 20 Dollars – Short-Selling to Preserve Capital

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Cool Stuff Under 20 Dollars – Short-Selling to Preserve Capital

In this episode of Rule Breaker Investing: Mailbag, Motley Fool co-founder David Gardner is joined by a motley group of guests to answer some questions and tell some inspirational stories. Listeners share their thoughts on some past podcasts with evergreen conversations, how they’re saving time on investment research, and suggestions on how to automate investments.…

Cool Stuff Under 20 Dollars – Short-Selling to Preserve Capital

Cool Stuff Under 20 Dollars –

Cool Stuff Under 20 Dollars - Motley Fool Staff

In this episode of Rule Breaker Investing: Mailbag, Motley Fool co-founder David Gardner is joined by a motley group of guests to answer some questions and tell some inspirational stories. Listeners share their thoughts on some past podcasts with evergreen conversations, how they’re saving time on investment research, and suggestions on how to automate investments. Also, find expert advice on retirement planning, short-selling, why you shouldn’t miss next week’s podcast, and much more.

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 August 25, 2020.

David Gardner: Well, it’s the last Wednesday in August, and that means it’s time for our August 2020 Mailbag, looking back over the month that was, Authors in August, we talked of conscious capitalism of pandemics and of leaving your earthly riches well to your next generation. A motley celebration of different and new possibilities which happens every August, when I have authors of some of my favorite recent books join me on this podcast.

But as usual, many of your questions go right back to our subject as well, the subject from which this podcast takes its name Rule Breaker Investing. So, let us then, yes, with Lewis Carroll’s Walrus, “The time has come” the Walrus said, “To talk of many things: Of shoes, and ships, and sealing wax, of cabbages, and kings, and why the sea is boiling hot and whether pigs have wings.” Only on this week’s Rule Breaker Investing.

Welcome back to Rule Breaker Investing. Yes, Authors in August is now behind us, August is not out yet, but the three podcasts that I enjoyed sharing with you, my three new friends Jay Jakub speaking about Completing Capitalism; Jeremy Brown talking about his book Influenza, looking a century ago at the pandemic of 1918; and then, of course, last week Amy Castoro, her book Bridging Generations. Just another delightful way to spend a month that often some of us anyway try to spend at the beach; I did get a little bit of beach time in as well and some reading. And I hope you have managed to find, as I’ve said a few other times this year, some beach within your Summer, even if you’re not physically at the beach. One way that I enjoy escaping is through reading books, occasionally musing about whether pigs might have wings.

So, before we get into 11 mailbag items, including a few guest stars joining me over the course of this hour, I do want to mention what’s ahead for September, since August is finishing up. I’m excited, next week, to bring you my next Five Stock Sampler. Yeah, next week is a good week to listen to Rule Breaker Investing, because I’ll be picking five new stocks along a theme I haven’t yet thought about. I’ll also be reviewing a couple of past stock samplers from years behind. In fact, I have a penchant, for whatever reason, as the calendar works out, for making Five Stock Sampler picks in September. I have four past ones, so there will be a lot of review-a-palooza coming up this September.

I also believe we’ll get joined by John Mackey, the Founder of Conscious Capitalism. He has a new book coming out, speaking of books, called Conscious Leadership. I have the pleasure of reading the proofs of it ahead of time, and I think it is excellent. Great fodder for Rule Breaker Investing from, I think, one of the world’s great living entrepreneurs. I will mention as well, John Mackey is on our Board of Directors. Full disclosure.

I do want to mention that, if you haven’t already, I hope you’ll subscribe to this podcast on iTunes or Spotify or Google Play, which I think is becoming Google Podcasts. Anyway, all five of our Motley Fool podcasts, Motley Fool Money, MarketFoolery, Motley Fool Industry Focus, Motley Fool Answers, and Rule Breaker Investing are wonderful complements to each other. There’s very little overlap among those five podcasts. I know many of you listen to more than one. If you’re a fan of this one, well, if you’re hearing me right now, I hope you are. I also hope you know about our other four podcasts. You can also follow us on Twitter @RBIPodcast. You can follow me on Twitter if you like, I’m @DavidGFool. Finally, I hope you’ll give us a review for Rule Breaker Investing. Throw me some stars. Let us know how we’re doing. I read every comment.

And I have a rich assortment of stories and questions and points, some reflections on our books as well. Once again, this particular month for mailbag, I do want to make a pointer. So, if you’re hoping to have your story featured on this podcast, and I sure hope you are, I love sharing your stories, especially ones that inspire all of us in the telling, but you’re going to want to keep it not too long. It’s kind of heartbreaking for me, some of the best notes I get are four pages long.

Michael in Calgary, you sent me an amazing note, it even starts, “I wanted to quickly share the impact [laughs] of the Motley Fool on my life … ” and it goes on four pages. I just can’t, it’s too long for this podcast for our format. So, some of the best stories I get to read are longform, but they don’t just quite fit, understandably, for our hour-long or so mailbag podcast. So, I want to thank Michael for a beautiful note. And just explain it, if you’d like to retell it in one-and-a-half pages, that has a better shot at making our mailbag podcast.

Anyway, thank you for all the great notes for those who are featured this week and, of course, for the many who are not. I had 26 pages to read through this month.

Well, as I want to do mailbag, I want to go to Twitter first, here are some hot takes from Twitter in the month passed. I want to thank Joe Tenebruso @Tier1Investor. Joe did a great job breaking down some, what he calls, growth investing lessons that could make you rich. And he draws heavily on material from me and my brother, Tom. And for anybody who wants to check it out, you can find it on Twitter. A lot of the points any regular listener will be familiar with. Joe does a nice job summarizing them and just pointing out, for him anyway, how well they’ve worked. So, thanks again to @Tier1Investor for that tweet series.

I wanted to share this exchange between @fools_gd and @FromValue; this is a fun one. So, ShipOfFoolsGD said, “It’s actually sad to me that any sites post share prices. It’s easy to bash people who don’t know, but that is literally the metric that everyone sees, not only when buying, buy even in the newspapers back in the day. It also makes it harder to assess growth from years ago.” ShipOfFoolsGD goes on, “If it wasn’t for @DavidGFool and @RBIPodcast playing the market cap gameshow, #MarketCapGame … ” [laughs] thanks for that, ” … I probably wouldn’t get it either. Thankfully, companies like @themotleyfool exist to help us, but they aren’t the ones on homepages typically. In today’s $0 fee world, price is irrelevant.” And, of course, @fools_gd is speaking to the idea that market cap is a more important metric for most people than the price per share of a stock, but a lot of people don’t know what market cap is and they see the price per share of a stock and they hear about stock splits and they get very focused on something that’s not that important to most of us. And I trust you, my dear listener, understand that.

Well, anyway From Growth To Value responded, “Fractional shares are only available in North America, as far as I know, so stock splits still make sense for the rest of the world.” And that @fools_gd concluded, “Good point. (checks globe to discover that there is in fact more to the world than just America).” [laughs] Well, I’m guilty of that too sometimes forgetting that, yeah, my assumption is everybody can use fractional shares and it’s such a wonderful equalizer, it makes it so that no matter what amount of money you have, you can buy ownership in any company, because you can buy just fractional shares of stock. You don’t need to have a couple of thousand dollars to buy Amazon stock or Tesla stock these days when you have fractional shares. But as is pointed out, many people, especially globally, don’t have that access. So, in fact, stock splits do have more meaning than I was probably previously thinking. That’s one of the things I like about Twitter: It expands the mind if you’re following the right people.

Couple of Twitter reactions to my conversation with Jay Jakub and his book Completing Capitalism. From Ross Daines @rossdaines. “This week’s RBI podcast was very good. The concept of measuring social, human and natural capital by non-financial metrics is special. Too much financial capital and insufficient of the other three is really interesting thinking. Thank you @DavidGFool.” Well, thank you, @rossdaines.

And Jon Quast @TMFJaguar. I believe John is a contract writer for The Motley Fool. TMF, indicating The Motley Fool. I think that’s true, Jon. You and I haven’t met, but Jon said, “Listening to @RBIPodcast on Completing Capitalism. Could you imagine how cool it would be for companies to report their social, environmental capital gains for the quarter, as well as financial? How cool would that be?” And he leaves it rhetorical.

And then the last Twitter hot take. This one ‘s from Anthony Stevens @Anthonythesteve. Anthony you said “Do you guys ever miss having your hammered friends explain things to you drunk? If yes, listen to @themotleyfool @RBIPodcast @DavidGFool at half speed.” He includes the emoji face with tears of joy. “What an absolute treat!” Well, that’s pretty funny. I have occasionally done that. I’ve heard Alison Southwick, Motley Fool Answers, slowed down, they even played it once back on their podcast to the listeners and it was hilarious to hear people at half-speed. Sounds like it can be funny for me, too. I do want to assure everybody, I do not drink and podcast, but through the magic of talented producer Rick Engdahl, maybe we could have a quick moment.


Do you guys ever miss having your hammered friends explain things to you drunk? If yes, listen to The Motley Fool’s Rule Breaker Investing podcast @DavidGFool at half-speed. He includes the emoji face with tears of joy. What an absolute treat! Well, that’s pretty funny, I have occasionally done that. I’ve heard Alison Southwick, Motley Fool Answers, slowed down, they even played it once back on their podcast to the listeners and it was hilarious.


All right. Rule Breaker Mailbag item No. 1 kicking off August 2020. I’m going to call this inspirational story No. 1. And in fact, I’m going to punctuate this month’s podcast with some inspirational stories. I have four of them lined up. They all say something different. This is quite a short one, it’s from Adam. Love this.

He said, “David, want to let you know that last week’s wealth transition Rule Breaker Investing podcast actually achieved the impossible, it got my 70-year-old dad to download a podcast other than the sports one he listens to that I produce.” Adam writes. Adam also goes on, “When I sent it to him … ” that is, a link to our podcast, ” … I didn’t want to tell him he could find the transcript somewhere online, just to see how much effort he would put in to finding someone else’s podcast on the internet.” Adam concludes, “He says he has not listened to it twice and wants to get together to talk about it. Miracles never cease.”

Well, thank you, Adam. That is particularly inspirational for me, because I love to think that the effort that my podcast producer, Rick Engdahl, my talented guests that I have in for mailbags, and my own efforts do connect with you, connect with as many people possible, both in this country and in every country worldwide. We’re trying to spread Foolishness everywhere we can. And I really thought, in particular last week’s podcast with Amy Castoro, spoke to a really important aspect of investing that we rarely touch on here in Rule Breaker Investing. And I would say that The Motley Fool, which provides wealth management advice in different ways, probably still under indexes toward this.

So, I thought it was an eyeopener to hear from Amy talk us through. We went through a checklist last week, how many yeses could you give yourself, the question was for you, my listener. How many yeses could you give to the idea that, yes, you’re doing it right. You are preparing any heirs in your future and any money that you have to whomever you’re giving it, you’re preparing it well, so that it will be well received, well used and not cause unintended consequences that are negative, which as Amy pointed out, happens more often than not.

I thought it was a profoundly important conversation. Certainly, the book Bridging Generations, for those for whom it’s relevant, I think you will greatly enjoy it. And I think last week’s podcast is one of those that’ll be fresh and feel evergreen and you could forward it to a friend a year-and-a-half from now and it would speak just as well and just as presently to that person out of time and out of place. So, I really enjoy that. And, Adam, I’m so glad to hear your dad heard it twice and it opened up a conversation that I think will lead to real positive results for your family and many others that are beginning to think more about this kind of thing.

Rule Breaker Mailbag item No. 2 also reflecting on Authors in August. Really love this note. Thank you, Billy Bushman, in Ponte Vedra, Florida. “Thank you, David, for the influenza podcast this week. I listen to your podcasts going to-and-from work. But this one was special, because I gained more knowledge than expected about a subject I know so very little about. Jeremy spoke fluidly, demonstrating his breadth of knowledge. I would love to hear more from him. I fully expect that when Jeopardy starts filming new episodes after the pandemic, the Jeopardy clue writers will inevitably create a virus category, and I stand ready to impress my wife and kids with this newly acquired knowledge.” That sounds like a good prediction to me, Billy. You close. “I can hear my responses now, who is Thucydides? Where is Haskell County, Kansas? What is the alignment of Jupiter and Mars? I truly will [laughs] amaze them.” For those who don’t know what these questions refer to, I encourage you to listen to this fantastic podcast. “Thanks again, David. Cheers, Billy Bushman!”

Well, thank you very much, Billy. A delight to read that. Yes, you know, there is always going to be something for the American ear about the British accent, and Jeremy so well spoken, just a charming person on and off the air. But to think that we did cover Thucydides; Haskell County, Kansas; and the alignment of Jupiter and Mars, thanks to Jeremy’s wide-ranging intellect, it added a lot of fun to that particular week earlier this month. So, thank you for that.

You know, it makes me think. Let’s do Authors in August again next year.

All right, Rule Breaker Mailbag item No. 3. This one comes from J.J. Marshall. “Rule Breaker team, I don’t think enough has been said about how much TIME Rule Breakers saves you when it comes to researching companies. At one point in my life I had plenty of TIME … ” And by the way, throughout this note J.J. capitalizes, all caps, the word TIME. This is a major theme of Rule Breaker Mailbag item No. 3, and I like it. I like this point, that’s why I’m sharing it. Anyway, J.J. continues, ” … at one point in my life I had plenty of TIME to spend looking into companies with the goal of investing weekly or biweekly. I’m sure you know how much TIME that took. Don’t get me wrong, I love to do it.” J.J. adds, “With Rule Breakers I find a lot of companies that would have fallen outside of my filter, but just as important, Rule Breaker and Stock Advisor filters out a lot that fall into that filter. I don’t think enough is said about the latter. Just because you don’t invest in something does not mean that you didn’t have to take TIME to research those companies as well.” He goes on, “The only reason I was able to move back into investing into individual companies instead of just using funds, which I still use, is because of a friend recommending The Fool to me. Having Fool Live playing in the background while I work is eight hours of commentary on companies and investing strategies that has more substance than any other network I have run across. I have had companies I decided to invest in that I heard on Fool Live, but are not one of your current recommendations, I looked them up, did some homework, decided that a few did make sense to put some money into. The wealth of knowledge a subscriber gets access to is phenomenal. I just don’t think enough is said about how much TIME a subscriber saves on the research side of things because The Fool gives you a great set of targets to drill into. This is TIME an average investor like me gets back and can spend with his or her family. Note: The Motley Fool does a better job at picking companies than I have, so that’s whipped cream on the pie. J.J. Marshall.”

Well, J.J. I really appreciate your point about time, because I think about time a lot. After all we’re all spending it constantly and sometimes in a very conscious manner and sometimes unconsciously. And that can be good sometimes, right, when you’re in the flow, you’re doing ceramics, which is a side calling for you and time doesn’t even seemingly matter in that situation, but other times, since it’s always ticking, time really does matter, sure does matter for investing, and I would say, for spending time with family. I try to minimize the time that I personally spend investing and doing investment research, and that’s my full-time job, because I try to spend so much time with my family.

I am happy I can look back on having now raised three kids, having just dropped our youngest off for his senior year of college. And I can say that I was always the dad that made every soccer game; that meant a lot to me. And that’s in part because our approach to investing doesn’t take that much TIME.

Now, you did mention, and it’s somewhat ironic, that you spent about eight hours a day [laughs] listening to Motley Fool Live, so in some senses that’s a lot of time and we’re honored by that. I realize you’re saying you’re doing it, kind of, while you’re working, which makes me feel really good. But I thought it would be great to have somebody who works full-time on Motley Fool Live, and so my good friend Dylan Lewis. Dylan, welcome to Rule Breaker Investing.

Dylan Lewis: Hey, David. I love that email; I absolutely love it. Because anyone who works in multimedia at our company and anyone who spends time in the podcast booth knows there’s a poster, we’re not able to see it now because we’re not at HQ, but there’s a poster saying, our listeners give us something precious, it is their time. It is their most precious thing. And that’s in our studio. And anyone who’s working in content here knows that, and we are trying to give people as much value as they can get from us, because we know there are so many other things that they can be doing and should be doing. And we’re a part of their lives, but we want to make sure that money isn’t the only thing they’re thinking about.

Gardner: Boy! We almost should just mic-drop it right there, because that is such an important statement and that makes me very proud to hear you say that. And you said it so well, Dylan. And you’ve helped host Industry Focus for quite a long time, you’re working a lot on Motley Fool Live, you’re doing many different things in and around The Fool, you’re a face of a lot of our YouTube videos and have really built up a YouTube audience since you’ve been here at The Fool.

You know, I do notice the next to mailbag items we’re going to be covering also mention Motley Fool Live, and it’s a big development for us just in the last few months, it was a surprise when my brother Tom Gardner, our talented CEO said, hey, I think we should start live broadcasting at the start of COVID from our website. And boy! Is it going to be great to look back on that moment 10 or 15 years hence and think about how we put in extra time and did something that we wouldn’t probably have started otherwise, and to think what it became. Because I think what you’re helping to build, Dylan, is something special.

Lewis: Yeah, we knew that this was going to be a really stressful and difficult time for a lot of people, and we know that when people see a lot of crazy headlines and they see a lot of crazy stock market moves that it’s helpful to have someone sitting next to you saying, don’t worry, it’s going to be alright, you know, we’ve got this. And we realized that via Zoom and via an ongoing livestream seven days a week, we’re able to be that reassuring voice for people and make sure that they’re sticking to the core principles that we know work, they get a little bit of fun in there too, and they stay the course with their financial lives.

Gardner: Well, well-put again, Dylan. Thank you. And let’s just glide right into Rule Breaker Mailbag item No. 4, because it’s more Motley Fool Live talk. And I want to ask you a couple of questions about it. Right along with J.C. here, our correspondent, who says, “Hello! I hope all is well. Thank you so much for starting Motley Fool Live. It’s another great resource provided by The Fool. I have a few questions and ideas that might make the service even better.” So, I’m going to pause it there.

The reason I have people like Dylan on, and my other talented guests later this hour, is because I don’t actually know myself the answer to many questions. We’re now doing enough different things to The Motley Fool, I can no longer keep up or speak authoritatively about where we’re headed. And, Dylan, I know we’re building the plane as we fly it, so perhaps you, yourself, feel like you can’t definitively answer where Motley Fool Live is headed.

Lewis: [laughs] I can give you the most directionally accurate answer, but I don’t want to be held too closely to any of the specifics.

Gardner: Awesome. Well, J.C. goes on, and he said, I’ll just read all of this and let you respond at the end, he says, “Do you think you might create an app for smart TVs and devices, like a TV, Roku, Amazon Fire Stick, so that streaming the service to a TV would be easier. Also, are there any plans to present the replay materials as individual “shows” versus a full five-hour stream? As it currently stands, it’s very tedious to find an individual hour or a half-hour show on the full daily replay. What about the ability to subscribe to each show in a podcast app, so that one can find topics of interest and download them to their device? I feel that you are providing so much great information … ” J.C. concludes, ” … but the way things currently stand, I cannot easily access the content. Hopefully some of these ideas are already in the works. I look forward to the growth of the platform, am excited of things to come. As always, thank you for all the support and guidance you’ve provided throughout the years. Be well, J.C.” Dylan, your thoughts?

Lewis: Well, I would love for us to fulfill J.C.’s vision of what Motley Fool Live could be. And for folks that are not familiar, this is our livestream, it’s daily, we are 9-to-5 Monday through Friday with some rare exceptions when we have some cool interviews coming in. We do weekend content 12-to-5 and we’ve doing replays on Sundays to highlight our “best of” content.

And J.C. is queuing us up to become a full-fledged media network with Motley Fool Live, and I love it. I think the idea of becoming effectively a cable channel that also has podcast tendencies, a great replay library, all of these things is what we’re inspiring to be. I love that our listeners and our members are, kind of, holding us accountable and they’re asking us to top it along the way.

A lot of great suggestions here. One of the big things that we’ve heard from a lot of people is the replay value is huge. And we are trying to think of the best ways to get that content to people, you’ll see some stuff getting sent out to you in your services, if we do a deep dive on a stock, that’s included in your service as a recommendation. We want to make sure you get that, so you get the 30- or 60 minutes on that content. We also are doing that “best of,” like I said, on Sundays. We’re experimenting with a lot of different things. And as David said, we’re building the plane as we’re flying it a little bit. So, subject to change, but we want to make it as easy and as accessible for you as possible, and replays are going to be a huge part of that over the next couple of months.

Gardner: Well, thank you for that, Dylan, and that’s all welcome. I want to mention, again, a lot of our listeners know what Motley Fool Live is, others are hearing about this for the first time. Who can access Motley Fool Live, Dylan?

Lewis: If you’re a member of a Motley Fool premium service: Stock Advisor, Rule Breakers, any of our other services that are a little bit more theme-oriented, all the way to Boss Mode, you have access to Motley Fool Live, you can go to and get all the information there. You can watch it on an embed on that page, you can check out the Zoom app and get the full functionality. We have programs that involve polls, we have trivia, we like to gauge the audience to get a sense of what’s going on. For folks that are on the go, they can also call in, and there are instructions at for how to do that.

Gardner: That’s wonderful. So, it is definitely very much a member benefit. So, it is not a present, like free TV that we could just put out there on a Roku, because it’s a member benefit. I hope we’ll continue to broaden it. But free stuff, like our podcast, remains free. Anybody hearing us right now is getting this for free. But I will say, the premium elements of Motley Fool Live are pretty compelling. For example, about a month ago I interviewed the CEO of DocuSign, which has been a spectacular Rule Breaker stock, and that was an exclusive on Motley Fool Live. Next week, in fact every other Thursday. So, not this week’s Thursday, but next week Thursday, September 3rd, I will be on Live answering questions from Motley Fool Rule Breakers members with some of my teammates. So, that’s something else that we do on Motley Fool Live.

We’re definitely not saying all the cool kids are hanging out there, because I think our podcasts are still pretty cool, and I hope you do too, Dylan?

Lewis: Of course, I work on the podcast, how could I not think they were cool. But I like that you worked that plug in, David, because if you didn’t do it, I was going to. I think, I’m going back to that first question, you know, the idea of stock ideas and things like that. I think one of the cool things about the Rule Breaker hour that you and your team do is, you kind of get a sense of what it’s like to be in the meeting room when you guys are kicking around companies. You know, you understand how people are looking at different trends, what comes up as you’re talking about different businesses, it’s a little bit of a different look than some of the formal write-up and recommendations that people get from you guys already.

Gardner: Well, and I love it that it’s interactive as well. So, we use Slido, which is a way to upvote questions. And so, we just tackle the most upvoted questions for about half of our Rule Breakers hour each time. So, it’s been a lot of fun; I’m looking forward to it.

All right, Rule Breaker Mailbag item No. 5. This one comes from Sam Wright, it’s kind of a two-part question and we’re going to be welcoming in one of our wealth management retirement experts Ross Anderson for the latter half of this, but there’s some more Motley Fool Live, Dylan, so before I let you go, let’s hear from Sam.

Sam says, “I’ll start off by saying as a member of Rule Breakers, my biggest disappointment is that with new livestreams, there’s just too much information for me to view everything each week, especially since I can’t yet quit my day-job.” Sam writes, “That said, thank you for all you put out there. Most weeks I’m still able to listen to all the various Fool podcasts. I would say my favorite part of them, especially Rule Breakers, is the variety. You give great stock ideas and investing wisdom, but also talk … ” well, thank you for this, Sam, ” … about games, soccer improvements, social justice, the importance of having police friends as well as Black friends, etc., and I find that super-entertaining and thought-provoking, it keeps me coming back. It also helps me start talking about stocks with people who haven’t started yet.”

“I have two questions though, and the first one may or not be radii related, but is there or is there a way to make the RBI livestreams into a podcast?” More for you here, Dylan. “Maybe … ” Sam goes on, ” … password-protected or something, so I can download it and listen on-the-go. One of my biggest roadblocks is, I don’t have time to sit down at the computer to watch, but I can listen to podcasts almost anytime. If this is already a thing, I may just not be in the know.”

Well, Dylan, let’s you and I cover this right now, is that already a thing?

Lewis: You know, David, before I answer that, I think you set me up, because we had such a great glowing review of how respectful we are to people’s time, and then Sam comes in and says, I’m getting too much from you guys. [laughs] But it’s a great question, and like I said before, we’re trying to figure out the ideal way to get people the information that they want on their terms. And I’ll have a little conversation with Kate Hood, who handles a lot of the stuff underneath the hood for Rule Breakers, about some of the different ways we might be able to bring that hour, in particular, to members of the service. Because we know that a lot of people like to go for a stroll and put something into their headphones and don’t necessarily want to sit in front of the computer for everything they do.

Gardner: Well, thank you for that, Dylan. And I’m going to let you get off the stage and get back to work on Motley Fool Live, no doubt, but I want to thank you again for all that you’re doing. You’ve spoken so eloquently about Motley Fool Live and helping us think about how it works and how we’re building [laughs] this plane as we fly it. So, I just want to say, atta-Fool!

Lewis: Love it. Thanks, David. [laughs]

Gardner: You’re welcome. Thank you, Dylan.

And now, because we are a full-service podcast, there’s a second part of Sam Wright’s question, and I’d like to welcome in my friend Ross Anderson. Ross, great to have you back to Rule Breaker Investing.

Ross Anderson: Thank you so much, David. Happy to be here.

Gardner: Now, before we talk about the other part of Sam’s question, Ross, I think there’s an event that you’re part of that’s just for internal Fools, our employees, we have about 450 employees. I believe you’re about to get an audience for something that you were staging for our company, could you explain briefly what the email is that I got earlier today?

Anderson: Oh, wow! Yeah, so really for a long time I’ve been moonlighting as a DJ, and that’s just a fun hobby of mine, something that I do. And the people team here asked me to perform for our fellow Fools. And so, on Friday I will be welcoming a bunch of folks into a Zoom stream and try and play some music that makes people happy and puts a smile on their face.

Gardner: Well, that is awesome, Ross. Thank you for doing that. We could all use more and more smiles as we proceed through 2020. Let me ask you, you go by, like, your own handle, you got, like, your own DJ nickname and brand?

Anderson: Well, that was actually given to me, believe it or not, while I was at The Fool. So, people couldn’t believe when I started here that I didn’t have a cool name, and so one of our fellow Motley Fool Wealth Management planners, Sean Gates, came up with the name Albatross, and it stuck. And it’s got Ross in it, of course, which I sort of like. And I also have found a number of things with an albatross that I find unique and sort of represent me. So, I’m happy with it.

Gardner: So, you’re DJ Albatross?

Anderson: In theory, that’s the name we’re using for this. [laughs]

Gardner: That’s awesome. And I think we’re having fun with this, but I can never tell how real it all is, Ross. Last question for you that’s not about retirement investing, and that is, have you done this professionally, do you hire out for weddings? Give me a little bit of your backstory here?

Anderson: I do, yeah. So, you know, what started as really just an odd job in high school was something that I kept doing through college and I’ve continued to have as part of my life. And yeah, so I do weddings and private events and things of that nature and still just have fun with it and feel very fortunate that I’ve been able to keep that piece of my history alive.

Gardner: Are you open to me plugging briefly that side-business of yours by saying, for anybody in the Greater DC Area: DC, Maryland, Virginia. If I want to reach out to probably one of the best local DJs, because I have a special event this Fall or Winter, how would I get in touch with the Albatross?

Anderson: Well, so honestly events have been so difficult, obviously. And we haven’t been able to do much of this, which is why the Zoom is so much fun. The business that I do run is called Bela Sono Music. So, if anybody is local and wants to check it out, we’re findable, but certainly appreciate the plug.

Gardner: Yes. Well, maybe it’s more about 2021, not 2020. But Bela Sono, I’m assuming we’re going with the Italian there, B-E-L-L-A S-O-N-A, something like that?

Anderson: You’re close. So, actually I translated it into Esperanto, it’s B-E-L-A, with one L, S-O-N-O. So, it means beautiful sound in Esperanto.

Gardner: Wow! B-E-L-A S-O-N-O. Awesome! All right. Now, to Sam’s question. Second question Sam writes is about what retirement investing looks like. He says, “I’m still a ways away from retirement, but I talk with people who’re much closer, and I wonder what you plan to do or what you recommend for people entering or in retirement? I presume when I get there, I’ll have a large amount, I’ll want to keep invested in addition to the five to 10 years’ worth of expenses I plan to keep in cash.” Sam concludes, “Do you suggest keeping five to 10 years of spending in cash and the rest in stocks? Do you suggest a certain amount in bonds? I just hate seeing the drastically [laughs] lower returns with even the best bond funds. Thanks for any insight you can share. Sam Wright.”

Well, Sam, I may have a thought or two about this, but really this is where I lean into the many professionals I’m surrounded with here at The Fool, whether they’re working on Fool Live or Fool Wealth Management. Ross, when you get a call into Fool Wealth Management that sounds something like Sam’s, what are some of the things you say back?

Anderson: Well, so I think Sam’s, first of all, even his premise of the question is absolutely coming from the right place. And he’s referencing five to 10 years as his safety net; we generally talk about a minimum of three to five. But the most important thing that you can do, as you move into that distribution phase, is recognizing that you need a safety net. Stocks are unpredictable from a day-to-day, month-to-month and year-to-year basis and we don’t want to see you in a situation where you’re being forced to sell stocks at bad prices that are otherwise good companies. And so, creating that cushion is step one. And he kind of built that into his question, and so great job there.

So, let’s assume that we’ve done that basic task and now we’re looking at all of the money beyond that. And retirement is really a situation where you’ve gone from having one investing goal to two. And that one has been to maximize, to accumulate, to build wealth and to get to a point where you’ve got that financial independence. As we transition into retirement, we now have two goals, protect what we need in the short-term and continue to grow your purchasing power.

The stocks are still the most powerful way, in our opinion, to do that, growing purchasing power. Does it have to be 100% stocks? No, not necessarily. It’s really a personal choice, not everybody in retirement is comfortable with the same level of volatility. And so, the same way that Sam is probably managing his portfolio a little bit differently using The Motley Fool’s guidance than maybe other folks are, he’s kind of building that into his process already. And so, I think you should continue that. And hopefully he’ll have a very good and well-tuned sense of how much risk he’s really comfortable with. And I think that that’s what everybody else needs to be doing as well.

Gardner: And, Ross, what are your thoughts, to conclude here, on bonds and bond funds these days?

Anderson: Well, so we get all sorts of push back on it. We do have a bond strategy as part of the Motley Fool Wealth Management suite, not everybody is using it, but it’s there for those that do need it to reduce some of that risk. You know, as we get further and further into our investing journey, the ability to add cash, I think, becomes more difficult. Because if you’re saving the same, whether it’s $500 or $2,500/month, whatever your number is that you’re contributing on a monthly basis, that’s becoming a smaller and smaller portion of your overall investing. And so, if you want to be in a position to deploy some dry powder when things go sideways, you need to have something that’s a little bit safer, so whether that’s cash or some conservative bond product, you need to be able to have that so that you can deploy additional funds when you see a buying opportunity. And so, to do that means, yes, you’re going to accept likely lower returns in the short-term to have that product as part of your portfolio. I think we need to make peace with that.

If we want to stay fully invested, that’s obviously a choice that we can make, and you’ve got less flexibility to go buy on a dip or do some of these other things if you want to go deploy some capital. I do think that there is a need, in many portfolios, for something that’s a little bit safer. We could argue cash versus bonds. I do think bonds will have a greater total return than cash will. So, if we’re going to put those two products against each other, it’s funny that one of the main things that I hear about bonds is, when interest rates go up, these things are going to get clobbered. And I do think that that is — the price action on a bond is down when interest rates spike up, but that doesn’t mean a loss of investing capital, just like when we take out a mortgage on our home we’re making a contract to pay back that mortgage either in monthly payments or in a lump sum at some point, and that’s the same way a bond works. And so, if you can continue to hold that asset, you’re not going to experience a loss just because interest rates tick up a little bit, so I don’t think that they’re an evil product, but certainly a lower returning expectation than your great stocks.

Gardner: Well, thank you for that, Ross. And before I let you go, I have to ask, because you’re seeing a whole side of the world I don’t. You’re a sister company, Motley Fool Wealth Management, this is not the company that I work for, which is where Rule Breakers is located. So, Ross, I’m always curious, like, what are you hearing or seeing? So, while I have you, what’s the craziest call you’ve taken? One of our members dialing you up and asking you this or that?

Anderson: Well, you’re right. We get to hear all sorts of different things and I feel very privileged that I get to work on the frontlines and talk to folks that have Motley Fool Wealth Management doing the investing for them and have chosen to hand off that responsibility that our team takes very seriously. You know, one of the things that I find fascinating is just how people choose to spend their free time and some of the great things that they do as hobbies. We’ve had investors tell us that they do things, like, I think it was hang gliding with, like, a jetpack essentially, it was like a powered hang gliding. I mean, just wonderful, wonderful things. Plenty of folks that love scuba diving and sailing. And just hearing the things that bring joy to our clients and members. I think those are the things that are most fun for me.

Gardner: Wonderful. Well, I’m sure you’re talking a lot about things like bond funds and how much cash to keep in retirement, but you’re also finding out about the lives behind those questions. And that’s a lot of the fun that we share on this podcast as well, where we talk as much, it feels like, about life as we are about investing. Well, thank you very much, Ross, really appreciate that.

Anderson: It’s my pleasure, David. Thanks.

Gardner: All right. Now, on to Rule Breaker Mailbag item No. 6. And this is another inspirational story. So, we led off this podcast with the story of Adam somehow getting his dad to download a podcast and listen to it twice, which I loved. And thank you for this one, Jake Edmiston. It goes like this, “Hello, David. I’ve now been a Fool investor for about two years. I started to become more serious in developing better financial habits when my wife and I were going to become parents.”

We’ll pause it there for a second. You know, I find a lot of people who reach out to us at The Fool, who click on an advertisement or find their way to Motley Fool Stock Advisor, which is our base level service that so many people have today. And they’re motivated by life events. It’s not by a sudden awakening that they had, or a dream that they should start investing, [laughs] it’s that they have a child or they’re getting married or they’re hoping to retire well. And so, I hear that in your story, Jake.

You go on, “I found your services through ads. And my buddy who’s a CPA, and a person who I trust financially, told me you were legit. And he had colleagues who used your services for their portfolios. While I’m now subscribed to Stock Advisor for two years and Rule Breakers for about a year. I’ve since opened up a Roth IRA for my wife and me, and a Robinhood account because, well, it has no fees and now has fractional investing. I realize Robinhood gets a bad rep … ” Jake says, ” … but I don’t day trade, I just like the flexibility that it’s more liquid than a retirement account, if for some reason I need the money. I have found I really enjoy buying stocks. I literally have started dollar-cost averaging daily. I put a $1 or so toward a couple of stocks daily. I look at it instead of buying a meal out or coffee, I just invest. I put in $13/day except for Thursday, when I invest $85 and buy shares of the newest recommendations and Best Buys, hopefully I can continue to increase the amount I invest, but that’s where I am currently.”

“My question comes down to, I now hold over 100 stocks with most coming from your services and a few REITs that I like. Do you have a rating system or a way you would prescribe adding money to these stocks? I do add to my winners, but at this point I’m a little overwhelmed by the number of stocks. I don’t really want to sell anything. Just curious if The Motley Fool or another website had a numerical ranking that I could access to help figure out where to put the dollars each day? I appreciate all your help; all you’ve done for me and my family. I’ve been crushing the S&P since following your recommendations. I look forward to continuing to watch my portfolio grow to allow my family to reach financial freedom.”

Gardner: Well, thank you for that, Jake, and congratulations. And I really love the literally dollar-cost averaging a day. I love how it sounds like it comes down to $13/day you’re deploying it into a bunch of stocks and then $85 on Thursdays when you have more to invest and go deeper and wider. I will say that 100 stocks is a lot, I keep up with about 50. But I’ve previously spoken to this in past Rule Breaker Investing podcasts. I can’t right away put my thumb on one of them, but if you were to Google it you might find it, but basically here are my thoughts about managing any number of stocks.

First of all, I’m a big fan of having a lot of stocks. That diversification makes me happy; it makes me feel like you are set up for success. I don’t think you have to go beyond 40 often; you’re at 100. But I wouldn’t stress out about the smaller holdings. That’s one of my cardinal points when we talk about size of portfolio, you should be training your time and focus on your largest holdings. And in a 100-stock portfolio, I’ll just make up — if there are any stocks that you have 5% or more of your portfolio, spend most of your time thinking about those. Secondarily, think about stocks that are maybe 2.5% to 5% of your portfolio. Those are worth looking at, checking their earnings reports, keeping up, figuring out which ones are winning, which ones you might want to add to. Finally, ones that are less than that, you really don’t need to spend time on. And given that you have a 100 stocks, that’s going to mean the majority of those holdings conform to less than, let’s say, 2% of your portfolio overall. So, I would say for all of those, those are just kind of nice to haves or nice to follow. And you might be interested in some of them to add to them, but I really don’t think you need to spend much time, since that’s one of the themes of this week’s podcast, much time on those at all.

In closing, yes, we do rank stocks in some senses. We come out with our Best Buy Now lists, you’re familiar with those. So, we’re giving you our favorite five each month. There are other ways to rank stocks. You could use Motley Fool CAPS and see what the community sentiment is on them or you could listen to the very next mailbag item on this week’s episode.

Mailbag item No. 7. This one comes from Aziz Alawadhi, and Aziz is writing in from Nova Scotia, Canada. I really love this note. I always appreciate people who come up with their own approaches to how to do the work of investing. And in this case, I intentionally came up with this note after Jake’s previous note, because, Jake, I think Aziz has an idea for you, one you might want to consider.

It starts, “Hi, David. I wanted to let you know that out of frustration from having to decide which winners to add to from my portfolio of 32 stocks each paycheck, I’ve developed a simple algorithm for automating this decision that you and your fellow Fools might find helpful. I hope the word “algorithm … “” Aziz goes on, ” … doesn’t intimidate some Fools from trying this, although the word is used in computer science, you don’t need to know how to code to execute an algorithm, it is simply a set of repeatable steps which achieve an outcome. A cooking recipe … ” Aziz says, ” … could be described as an algorithm.” Beautiful job breaking down that term.

He goes on, “Onto the algorithm. I simply calculate the market outperformance of each of my stocks since the weighted average date of purchase and I divide it by the percentage of my portfolio that that stock currently represents.” I’m going to read that again, because some of us are very math inclined and some of us are going to want to hear this twice to picture it in our heads. “Onto the algorithm … ” Aziz says, ” … I simply calculate the market outperformance of each of my stocks since the weighted average date of purchase.” So, if he purchased it over three or four times, you weighted average their dates, and then he divides that by the percentage of his portfolio that that stock currently represents.

Aziz goes on to offer this example. “For example, if a stock is beating the market by 10% and currently represents 5% of my portfolio, well the resulting ratio would be two. Now, the higher the ratio, the more under-allocated I am to a winner, meaning that I should add more to that stock. As I add more to the stock, the denominator increases, decreasing the overall ratio for that stock, moving it down the ranking. Another added benefit of this method is, if a stock has been a big winner and now makes up a hefty chunk of your portfolio, using the ratio will prevent you from adding to it and increasing your exposure even further. Although the stock may be a winner, it is also overallocated in your portfolio according to this ratio, and adding to it any further would increase overall portfolio risk. The conclusion … ” he says, ” … adding to my winners using this method has served me well, as my portfolio is beating the market by 63% in the span of one year. Fool on! Aziz Alawadhi, Nova Scotia, Canada.”

Well, Aziz, a couple of thoughts back for you. First of all, thank you very much for sharing your approach to adding and building your portfolio. It certainly is one predicated on the notion of adding to your winners, but after all, for Rule Breaker Investing that makes a lot of sense. There are six traits of Rule Breaker investors, six hows of how you and I invest. And No. 2 is add up, don’t double-down. That’s something I’ve pounded home silly on this podcast, on Twitter, I’ll do it forever more. Again, there are six hows for how you and I should do the work of being investors, whatever stocks we’re buying. And No. 2 is add up, don’t double-down. In other words, let’s add to your winners, winners win. So, yes, Aziz, your algorithm has baked into it that that is the way to go. Not everybody does invest that way, some people don’t want to invest that way. So, this algorithm would not be for them. Anyway, I love the creativity of it.

And my second point, I also want to say, I think you’ve done a good job pointing out how, when winners win, they can sometimes just become too big a part of somebody’s portfolio. So, the discipline of your algorithm is, it disciplines you away from adding even more, arguably way too much, if you’re already heavily overallocated into a stock. I’ll also say that while it is an algorithm, and we’ve done some math here, and not everybody likes ratios and we’ve lost some of our audience [laughs] in the last five minutes, the vast majority, I think, can understand what you’re doing and can appreciate what it is. And it might well be helpful for somebody like Jake who’s looking for a more automatic way to allocate constantly, especially for somebody who’s literally dollar-cost averaging every day, I could imagine this is worth considering. So, I want to thank Aziz for sharing his approach to investing.

All right, on to Rule Breaker Mailbag item No. 8. I think we’re going for 11 this month. That’s rare. I hope this isn’t way too long a podcast. I sure am having fun; I hope you are too. And it’s time for inspirational story No. 3. Again, I have four queued up for this podcast. Here comes No. 3. It’s from Jason Moore.

“David, a celebration story for the mailbag, and many thanks for your great podcast. Here’s the tale of our first spiffy-pop.” Now, I’m going to full-stop there and briefly remind, especially new listeners, what a spiffy-pop is. It’s when you make more money because the stock pops for you. It has great earnings or it gets bought out or whatever it is, it makes a big move, but you make more money in that day than you paid for the stock way back when. In other words, the dollar move of your stock is greater than your cost basis. For a couple of decades now, just about, we’ve called that a spiffy-pop. And those are the pops that we celebrate, playing the long game of Motley Fool investing, and especially Rule Breaker Investing. So, that’s a quick reminder of what a spiffy-pop is, because Jason’s note is all about spiffy-pops.

Here we go, “Dear, David, here’s the tale of our first spiffy-pop. We bought Shopify for $39.93 a share on November 10th, 2016, after it had already doubled following your first Rule Breaker recommendation. On February 12th of this year, Shopify was flying high and I thought we might see our first spiffy-pop. That would mean the stock would need to go up more than $39.93 in a single day, but alas … ” Jason goes on, ” … it landed short by $1.50, closing with a gain of $38.50 for the day. And then the pandemic hit, and before ever tasting a spiffy-pop we ate three spiffy-drops in eight days, March 9th, March 12th and March 16th.” Jason documents, “But then only eight days after that … ” and this is reminding me of the incredible volatility of this March. He says, ” … eight days after that Shopify finally popped … ” as in spiffy-pop, ” … and it has not stopped.” And boy! Is that true, not just of Shopify, many other stocks have been behaving in this manner through 2020 in a way that surprises and shocks even me. But I’m never going to try to explain the near-term, we’re just going to try to own the best companies and hold them for as long as we can.

Anyway, Jason goes on, “Shopify finally popped and it has not stopped. Just four months later, on July 29, we sampled our first Shopify-flavored forget-me-pop.” That means that literally it spiffy-popped for the 13th time, we call that the forget-me-pop. There’s no real point in counting spiffy-pops after a stock has done it 13 times. I find it a little bit of a waste of time, but it’s a wonderful place to get, and it is remarkable. It’s going to take one of those once-in-a-generation stocks, stocks like Amazon, stocks like Shopify to have this kind of action. But, Jason, I am so excited to think that you experienced 13 spiffy-pops between March and July. And it’s forget-me-popped.

You go on, “What’s remarkable is that, while Shopify popped 13 times between March and July, it also spiffy-dropped eight times along the path from $400 to $1,000/share. It makes me think, what if we panicked and sold after the third spiffy-drop? All those spiffy-pops would have become what? Well, maybe … ” he suggests, “… whiffy-pops, the pops you missed because you panic and sell?” By the way that is a neologism, that is a new word creation. And I like that one a lot, Jason, the whiffy-pop, the one you didn’t get because you panicked and sold.

He concludes, “Popping and dropping is just the way that winners and Fools roll higher. A very Foolish thanks, David, for our first spiffy-drop, spiffy-pop, forget-me-pop and all the tip-top guidance and fun along the way to a smarter, happier, richer tomorrow. Yours, Jason Moore.”

Well, Jason, that was a delight to share with our worldwide membership. It’s always inspiring to see somebody actually go out there in the field and do it and make it happen, and suffer some tribulation and show resilience. I also want to say, let’s not forget that Shopify has been crazy good, unlike almost any stock you could ever expect. It only took four years for you to make that. A lot of my spiffy-pop stories take place over 10 years or longer. So, let’s all pinch ourselves a little bit that we found that company and the low-cost basis we did. And I especially love Jason that it had already doubled from our cost when you decided to buy it, and look how things have gone for you. Fool on, Rule Breaker!

All right, Rule Breaker Mailbag item No. 9. This one comes from Jared Carr. Jared, obviously listening to this podcast, because he’s reflecting on something that was said some time ago on it.

Jared, you wrote, “Hi, David. Thanks for the podcast and all you guys do at The Fool, all the services are incredibly enriching for myself, my friends and family that I’ve been able to pull into The Fool fold.” Well, thank you for doing that Jared. I’m a 35-year-old mechanical engineer living in Denver, Foolorado, [laughs] and I wanted to get your thoughts on short-selling. I’m a subscriber to Stock Advisor and Rule Breakers. Now, a few weeks ago on the podcast, you mentioned having a change of heart on short-selling. Sounded like you’ve historically been down on profiting from equity losses, i.e., “I was against it.”” Which is what I said, yes, indeed, years ago that is how I thought, “Similarly … ” Jared says, ” … I have always had the same philosophy, in principle, that I did not want to be profiting when others were losing, it just always felt wrong. Recently, I’ve been having a short-selling change of heart too, though, as I work on some strategies to preserve capital in the event of a market turndown, and short-selling with limited risk through an options strategy is part of that. It seems like a necessary strategy to ensure my gains and savings in retirement allows me to “retire” sooner with less savings, if I know the wealth is adequately protected and can even grow in the midst of disorder, an antifragile strategy, if you will. So, long or short, wanted to see if you would share your journey of your change of heart on short-selling?”

Jared, very kindly writes at the end; no one else ever writes this. “If you choose to include this in the mailbag podcast, feel free to edit as you see fit for the audience.” Well, [laughs] that’s very considerate. Now, if you heard a little bit of a giggle, that’s because I’m about to welcome on my friend Jeff Fischer, longtime Motley Fool, one of our longest-standing Fools. He’s helped run Motley Fool services, today he’s helping run 1623 Capital. Jeff, welcome.

Jeff Fischer: Thank you, David. Great to be here.

Gardner: I’m just so glad to be with you. I know you and I have not seen each other in months. I think one of the last times I went out to supper was with you and your lovely wife, and we two couples had a good time at a restaurant, Jeff! And nobody was physically distanced because this was pre-COVID.

Fischer: That’s right. That was late-February. We had a great dinner. I went to see a play. And Ruth Bader Ginsburg was at the play, it turns out, as well.

Gardner: I remember that, you’re right.

Fischer: And that was our last time out. That’s true.

Gardner: Yeah. Although, I will say I’ve been back to a restaurant a few times now in the last month or so, always outdoors. Feel pretty safe about it. I feel like the best restaurants are taking real precautions to make it so that we can all come back. Have you been to a restaurant since, Jeff?

Fischer: We have done takeout, and we, like you’ve, just been out outdoors all the time. So, that’s been nice.

Gardner: Yeah. Well, Jeff, you know, I was reading Jared’s note, of course, and thinking about you, because you, in a way, have made a career of understanding how to do short-selling well, and maybe with an options strategy. And I’ve never used options at all, as I’ve sometimes mentioned in the past on Rule Breaker Investing. So, I’d mainly like you to speak to Jared’s question. He does ask me about my journey; I’m not going to share it right now, it’s not that interesting or long a story, but longer that I’d want to spend near the end of this podcast with my good friend Jeff Fischer here. I will say that, in general, what I started to realize is, whether you’re buying or selling a stock, Jared, you are making a trade with somebody who’s on the other side of that. And when you sell a stock short, you’re just selling first and then buying later. You’re still making a buy and a sell. And so, if you think about it that way, I don’t think you’re profiting on anybody else’s demise. Although, ultimately, as the short seller, you’re hoping the stock declines over the period of time that you hold it.

Anyway, that was kind of the aha! moment that I had that changed me on this point. Jeff, what is your take on short-selling as a strategy, do you use options for it, what are your thoughts for Jared?

Fischer: All right. Well, Jared’s question is a great one. And, David, I love that we’re talking about it, because I first started selling short in 1996 with you and your brother Tom in the original Real Money Fool portfolio. So, our short-selling goes far back, almost 25 years now. And over time I’ve had different thoughts about shorting as well. Does it deserve a place in my investing? And so forth.

But for Jared who has thought about it quite a bit it sounds like, and he believes that it has a role in his investing, it can make sense, but I’ll preface this by saying that, short-selling, no matter how you do it, is very time intensive, it has different stress levels than going long, because it’s shorter term in nature, it’s expensive, whether you’re buying put options or selling short a stock. And the odds, especially with selling short individual companies, are stacked against you. The risk/reward is stacked against you, because a stock can rise and rise and rise. But it can only fall so much, and your gains are limited to how many shares you decide to sell short when you sell short, or when you buy put options, as Jared is speaking of doing.

So, all of that said, shorting is challenging. That’s why the funds that do it long, short equity funds, have the fees that they do and so forth, because it’s time-intensive, and it’s a different expertise, if you will, compared to going long a stock. So, Jared is looking to protect himself by purchasing put options or using other options strategies to effectively make money when the market declines. What he’ll need to do is maintain those positions, so if the market is rising, he’ll have to roll the positions to higher strike prices and pay again for his insurance, think of it as an insurance policy and so forth. So, the costs do add up. And in general, to really protect your portfolio in a meaningful way, you can expect to spend 4% to even 6% of your portfolio’s value per year in put options that are fairly in play at all times. So, those premiums that you pay to ensure your portfolio do add up, Jared, and it can be expensive.

So, I’ll say, before, David, I want to hear your thoughts, think about cash as well. I can’t give investment advice, but what about your cash balance? If you have enough cash, that can cushion you and work as a hedge as well and not be nearly as time-intensive or labor-intensive and costly as shorting can be.

Gardner: Well, thank you for that, Jeff. And I really don’t want to add too much, because, again, you’ve made a living thinking about how best to allocate across, going long, going short, and in-between; stuff like cash. And it’s really not part of my background. You helped run Motley Fool Pro for many years and help people do exactly this through that service. For me, and of course, for this podcast, we’re pretty much all along all the time. And the reason that I stopped shorting is because I decided that while it is fun and we’ve had a lot of fun together shorting companies — you and I once spent one hour in Donald Trump’s office, this is not a political statement, this is simply a matter of the historical record, we were short Trump Hotels & Casino Resorts. And very publicly, to the point that Donald wanted to meet us, and you and I shared that moment and no one can ever take that away from us, Jeff Fischer.

Fischer: [laughs] This is true. And what I’ll say about shorting overall is, the way I found that it works best, given I’ve been doing this for so long, is to have an active basket of shorts, and that’s really time-intensive, but in that way you have — say, you have 15, 20 different shorts, and they’re all small in size, so your risk is diversified. And you’re betting on companies that you believe are mediocre or becoming less relevant or failing financially, and therefore the odds should be in your favor. So, that’s one way to short. But the reason I’m a little cautious about saying that to Jared is, it’s very time-intensive and difficult to manage a whole portfolio of shorts like that. But if you love it and want to do it, that’s one way to approach it. Options are another way, and that could make sense for him as well.

Gardner: Well, and we certainly have a lot more information on our site. You can go to and Google these topics and hear more from people like Jeff Fischer who’ve written articles and tutorials around these things over the years. Our YouTube site, also a lot of information about different aspects of investing. So, I feel good that we have answers for people out there. But to conclude this one, Jeff, and then we’re going to go to the next. Yeah, I stopped shorting because I just didn’t feel like it was that worthwhile. Even though it’s fun to watch a stock drop 20% and feel like you beat the market, especially if the market was rising, you feel really great about that. You also feel good when the market is dropping, because you have part of you short. But truly, I think just buying to hold great companies and letting them compound over the years is so much simpler, and so that’s why I’ve ended up being the Rule Breaker that I am.

Anyway, thank you for that though, Jeff. Jared, thank you for that note.

Let’s go to mailbag item No. 10. Jeff, are you still with me, will you hang out for this one?

Fischer: Definitely.

Gardner: I know, initially, I only invited you to talk about Jared’s note, but I think you’re going to have something to say about Aiden’s note. So, let’s go here. “Dear Fools, I’m a high schooler named Aiden, who’s written in before. I love your support of conscious capitalism, and to that end I have this question, is not supporting the buying of Chinese stocks indirectly supporting and legitimizing a regime which is perpetrating what many news outlets have called a “second Holocaust” on their Muslim citizens?” So, this is a pretty deeply serious question from somebody who is in high school and thinking deeply about the full effects of our investment decisions. Just to conclude this one, he says, “I personally own” Which is an example of a Chinese company and one of our recommendations in Motley Fool Stock Advisor. He says, “I’m very happy with it, aside from this. I believe in your idea that we should invest in companies that make a better future, but if the government of that company’s mother country is evil should we still invest in that company? Thanks again, your Motley Fool Answers podcast has helped me in my college search a lot. Aiden Dire.”

Well, I’m delighted to know that Motley Fool Answers, which I mentioned earlier, is helping people search through colleges. That’s great to hear. But, Jeff, as you hear that question, I realize I’m just hitting you upside with something I hadn’t prepared you for, but I know you think about these things and I do too, can you give me an initial thought when you hear Aiden? Let’s pretend he raised his hand in the classroom and you’re teaching that high school class and you’re Jeff Fischer. What do you say back?

Fischer: Certainly. My first thought is, we need to find out if the company you’re investing in is complicit with the government that you disagree with? If the people working there and the people who have founded the company are engaged in behaviors directly or indirectly that you’re not proud of or that you flat-out disagree with or that you feel are inhumane, etc. Then, of course, you don’t want to be investing in that company.

But if the company is a company run by ethical people and doing good for its customers, it just happens to be in a country that’s run by a government that you disagree with, then I wouldn’t paint the company with the same brush that you’re painting the government. You do need to do more due diligence, though, to make sure that that is indeed the case.

Gardner: And it’s particularly interesting to me that Aiden happens to have mentioned, has gotten dinged, and rightly so, for a totally separate reason. And I feel that at least one note from a Stock Advisor member in the past week talking about its CEO, Richard Liu and an alleged sexual crime that he committed when he was on U.S. soil. I think it was last year. And does that mean we should even feel comfortable investing in that company? And people are going to come down on different sides there. But, Jeff, just broadening it a little bit, I’ll just share a portion of an answer that I sent back to that member this past week.

And I basically said, I think every company, just about, is bigger than any one person. And so, I look at the enterprise itself and I ask, is it doing something that I think makes my portfolio reflect my best vision for our future? If someone is a criminal, I’m the first to hope that they come to justice. And whether or not that happens or should happen, in the case of Richard Liu, is secondary to the advice that we give, which is, let’s look at the companies, and as you said, are they complicit with bad people? Are they doing bad things? Those are reasons I would never recommend a stock. And I’m really glad Aiden is thinking about this. And, Jeff, I think you helped him think about that in such a good systematic way.

But even as I, kind of, explain how I think about it, and hear how you think about it, I realized there are going to be a lot of different viewpoints. And, Jeff, would you agree with me then that a good takeaway here is, if you’re not comfortable investing in something, don’t?

Fischer: Completely agree. And I know we both love that Aiden is investing and thinking about these things in high school. That’s a fantastic early start to a lifelong investing career.

Gardner: Jeff, as we close, let me ask you, what was the first day that you purchased a stock? Can you tell that story at close?

Fischer: It was after Black Monday in 1987. I was 17 years old at the time. And I’ve been following the stock market since I was 13, and having seen the market fall some 25%, I thought very simplistically, well, things are lower now, so let’s buy my first shares of stock. It was a few hundred dollars. I invested in Citibank [Citigroup] and I invested in a company called Radice Corporation, which was a Florida real estate company. I just happen to like the tropics; I knew Florida a little bit. And that company went bankrupt the next year. [laughs] So, it was a good early lesson back then.

Gardner: What a great story. The day after the market crashed, a 17-year-old Jeff Fischer is in the brokerage firm opening up that account, slapping down a couple of hundred bucks on his first two stocks. Well, it’s gotten better and better ever since. Congratulations, Jeff. And what a pleasure it is for me to think that in my 28 years at The Motley Fool, the vast majority of those have been spent with you at The Motley Fool as well. So, thanks for all you’re doing for Fools everywhere.

Fischer: Oh, thank you, David.

Gardner: All right. And we’re going to close it out with Rule Breaker Mailbag item No. 11, which is our final inspirational story. Best for last; well, we’ll see. Before I go there, though, let me mention a couple of things noted from earlier in the show. The first is that I did just go back and find that it was the February 6th, 2019 Blast from the Past Vol. 2 podcast speaking about how you can manage any number of stocks. I referenced that a little while ago on the podcast. I did just kind of Google it and find, if you would like to hear me talk to that point, it’s in Blast from the Past Vol. 2 from 2/6/19. Google it or find it on iTunes or whatever, and you can hear me speak to that point.

And then the second thing I want to say is, I feel as if time was an [laughs] emerging theme for this particular podcast, given the note that we led off with about TIME. And so, I’m conscious this might be, like a lot of mailbags, one of our longer podcasts. I hope that this time has been worth it to you. I hope it felt chock-full to me, and we covered a lot of Motley topics with a lot of different voices. But I am always wondering, was that podcast too long? So, again, if you have any feedback for us, [email protected] or you can just leave reviews right out there on the internet, maybe let me know specifically if you wanted to write in, is an hour plus OK for you for our mailbags, occasionally? It’s not something I try to make a habit of. Or would you much prefer this podcast come in with fewer points, shorter each month’s mailbag?

And I would be remiss, as well, if I didn’t also mention that I was on somebody else’s podcast this past week. So, if you’d like to spend more time with me, in fact, about a 90-minute long podcast, I joined my friend Benton Moss for his podcast Circle of Competence. And Benton and I talk a lot about investing and some fun backstory. You may remember, Benton, in fact, it was one week after the podcast I referenced just a minute or two ago, Blast from the Past Vol. 2, the very next week, February 13th, 2019, I had Benton on this podcast. At the time, he was a minor league baseball pitcher, full-time blogging about his love of investing. Well, unfortunately, due to a career injury, he will not be pursuing any further, I don’t think, a career in professional baseball. But he made a good go of it. In the meantime, he has really embraced full-time investing, commercial real estate and other aspects. He’s one of the most intellectual people I know. He reads widely, thinks a lot as he blogs for his Circle of Competence blog each week, and now he has a podcast and I was on it. So, if you’ve not spent enough time with me already, 90 minutes more if you want to listen to me on Benton’s Circle of Competence podcast. Downloadable wherever podcasts live.

Rule Breaker Mailbag item No. 11. Rarely do we rock the double-digits. This one comes from Christian Belko. Thank you, Christian, for this closing inspirational story.

“Hi, David. I’m writing this to you as I get ready to move into my dream home. For the past six years I’ve saved and invested wisely, with some of the recommendations and best practices from The Fool, and now it’s paid off, as I’ve been able to buy a great home, do some renovations to improve the home for my family and set ourselves up for success in the home for the future. This was not without its challenges, though. Shortly after we purchased our home, my dog, who’s my best friend, needed spinal surgery to repair a herniated disk. We also had a strong storm just a few days ago which caused some minor flooding and a host of contractor-related repairs and upgrades we had to pay for. But I didn’t worry about any of those things because I had my investments. And I also had the knowledge that all of these things could be covered without having to make difficult choices or shortcuts. I was able to improve my family’s quality of life and keep our best friend around for many years to come. I wanted to thank you and all of the staff at The Motley Fool for helping me learn the power of investing and I look forward to starting up a new group of investments again soon. I’m planning to purchase a subscription to Stock Advisor as a thank you as well as to help me get started again with finding long-term winners for our future. Thanks for everything and Fool on! Christian Belko.”

Fool on yourself, Christian!

David Gardner owns shares of Alphabet (A shares), Alphabet (C shares), Amazon, and Tesla. Dylan Lewis owns shares of Alphabet (A shares), Amazon, DocuSign, and Shopify. Jeff Fischer has no position in any of the stocks mentioned. Ross Anderson owns shares of Alphabet (C shares), Amazon, DocuSign,, and Shopify. The Motley Fool owns shares of and recommends Alphabet (A shares), Alphabet (C shares), Amazon, DocuSign,, Roku, Shopify, Spotify Technology, Tesla, Twitter, and Zoom Video Communications and recommends the following options: short January 2022 $1940 calls on Amazon and long January 2022 $1920 calls on

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