"May you live in interesting times," is said to be an ancient curse. But is it? May was certainly an interesting month, and our mailbag doesn't disappoint! In this episode of Rule Breaker Investing, we have perspectives from all ages, from around the world, and even from the future! 

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This video was recorded on May 26, 2021.

David Gardner: Following 27 years picking stocks for Fools worldwide, well, it's not every day or month or year or even decade that I changed my life's work, my focus. It's probably understandable that this month's mailbag, more so than most others, has me reacting to your questions about perspective, about the whys and hows instead of just the whats or the whens. These thoughtful global listeners are so full of their own wisdom. It's quite natural for me to share Foolish perspectives coming in from Singapore, or France, or New Zealand, Dubai, or some place more modest like Alexandria, Virginia, where The Motley Fool is based and where many Fools too live. Perspective, not just one, many. A diverse and enriching set of perspectives, each of which looks to me like a little piece of glass, its own unique hue, its own unique shape. This month's mailbag may be thought of as a stained glass window, one that you could buy from right nearby looking through it or from a far looking at it, this week or perhaps again, a few months or years from now. Perspective, perspectives, only on this week's Rule Breaker Investing.

Welcome back to Rule Breaker Investing, I'm David Gardner. Thanks for suffering a Fool gladly again. This week, it is the final week of May of 2021. One of the things I always like to do for our mailbag episodes, which we do when months end, is I like to remind us briefly of where we've been this month with this podcast. You might think it was just all about my transition all the time, but the truth is that we did three podcasts before this one. The first one was on Company Culture Tips Volume 8: The New Normal. The second one was indeed about my announcement, it was called A Road Less Traveled in Ten-and-a-Half Chapters. I started writing it that morning. It was 9,309 words. It turns out that it takes about 61 minutes to read, which was how long the second week of the podcast was A Road Less Traveled, but then last week, back at it again to investing with calculating risk ratings, calculating risks foolishly with Alicia and Maria. It was a very Motley month taken all-in-all with a number of different perspectives. I used that word a few times at the top and I was thinking, how could I not invite in my friend and producer, Rick Engdahl. Because Rick, one of the things I've always appreciated about you, is you're pretty doggone, good photographer. I don't know whether you're a professional or not. I think that I would pay you. Rick, have people paid you for your photography?

Rick Engdahl: I try not to take any money from my photography. I enjoy the amateur lifestyle. You will appreciate the Latin roots of amateurs, it's doing the thing that you love the most, and that's more important than making money out of it for me, plus I'm not very good at the business side of things. 

Gardner: Well, Rick, I think you have a pretty good business mind overall, but I appreciate that point. I will say that if there's ever a hedge shot that we need to refresh for me from one year to the next because I don't ever want to be the guy who has the photo from 2012 and you meet me and it's nine years later and I don't look like that anymore. I like to have it updated every year. Rick, you're always the one who takes my head shots, among many others. But you're out there in the world, you're taking pictures of nature or communities. I see your work sometimes on Twitter. Anyway, this is a way for me to say that I think you get perspective. I think that especially when you think about a photographer who must position him or herself at a certain point, and then decide whether to zoom in or out, how much light is needed, and what is the actual angle and composition, that is a very rich understanding of perspective. I have to admit, I'm not really good at it. I never took a photography course. But you were saying something before we started the show that I really loved. What was that, Rick?

Engdahl: Just that these days, it's really difficult to purchase a bad camera. There's so many good cameras out there. Most people have one in their pocket, their phone. We all share these wonderful tools for taking photographs, in this case. The only thing that separates me from you or from the professional photographer or from anybody else is just that, is the perspective, where do you bring that camera? How do you look through it? What is the vision that you're sharing with the world? Perspective is extremely important, I think in that discipline.

Gardner: Thank you very much for that word. You're right. In fact, I'm glad we went there at the start of this week's podcast because I think it gives us a good perspective to carry throughout. Thank you for that, Rick. 

Without further ado, I say we get into this mailbag. Now, traditionally we've led off with some hot takes from Twitter, and I've just got a few this month. The first is from @AuthorUK, he is Owen Lean. Owen, I've been enjoying some of the videos you've been posting onto YouTube. I enjoyed this tweet. This is reacting to our risk ratings podcast. Just last week, you said on the RBI podcast, "Great podcast as always. Hypothetical question: if a company IPOs that specializes in haunted world conquest board games, can we call that a medium risk stock?" Owen, concludes, I'm sorry. Now, I have to admit, when I first read that I didn't fully get it, but there is this 15-second rewind, little button that a lot of us have on those smartphones that Rick just referred to on your podcast interface. Feel free to hit back 15 or back 30. Listen to that one again. Did you? Now, you'll know why Owen concludes, I'm sorry. Two other takes from Twitter are very similar but just reflecting a lot of others. Josh Johnson, @JohnsonJoshJoshua, you wrote, "Congrats on moving on to your next endeavor. Selfishly. I'm sad to see you stepping aside, but that will make the Rule Breaker podcast even more special. Fool on." Thank you, Josh. Santi, @SantiSketch, "Yesterday's @RBIPodcast," referring to A Road Less Traveled in Ten-and-a-Half Chapters, "got me teary-eyed, when in fact you're not leaving. What a journey, what a gift of teaching, giving, and sharing that you have. Truly remarkable. I will be sharing this episode with my friends and family. I was deeply touched. Thank you, @DavidGFool." Well, thank you, @SantiSketch. 

Thanks to so many Fools, for your notes that I received in the last few weeks. I love hearing each of your stories. We'll certainly be sharing some of those this week. But boy, I couldn't nearly share all that I'd love to share in this month's mailbag because there's just too much and too many good things, and that's a great problem to have. Thank you to each of you and for many other tweets in the past weeks. 

Rule Breaker mailbag item No. 1 this month. This one comes from [...] writing in from Singapore and thanking me. "Dear, David. My name is [...] from Singapore and yesterday was my birthday when I found out that you will be handing off your stock-picking responsibilities. What terrible birthday news, I thought to myself. I have been a fool since 2017, but luckily changed to a Fool since May of 2020, after discovering your Rule Breaker podcast. Yes, I've listened to every single one of them. In my opinion, you are the most inspiring person for investing for me the right way," says E. "You've provided perspective, the right Foolish mindset for the long game and taught me to be a part owner of many great companies." Well, I love hearing that from you. Thank you. "I listened to your conversation with Tom last night." Now, this is referring to a Motley Fool Live event that my brother Tom and I did talking together about this, about happiness. "I have a question for you. If happiness equals reality divided by expectation," which is indeed the mathematical equation I threw down in that Motley Fool Live event and one I've talked about in the past, probably on this podcast some before. But I'll say at once more, "If happiness equals reality divided by expectation, do you associate happiness with investing? For example, if a company went up by 10 or 20 times over a long period, does that make you happy? Should we lower our expectations about our companies to make us happier?" That's a fun thought. "Is that contrary to one of your teachings that you were optimistic that stocks will generally go up more than they go down?" which is the expectation and which I admit E. contrasts with the idea that you should keep your expectations low. This now concludes, "Maybe the bigger picture is that we shouldn't tie happiness with stock performance at all because life is much bigger than that. We should save like a pessimist, invest like an optimist, and live a happier Foolish life. Please let me know your thoughts on this. Thank you for all the invaluable teaching, Fool on." 

Well, I think you put it best right at the end. I love that. Save like a pessimist, invest like an optimist, and live a happier Foolish life. I can't really top that. I think you just provide better wisdom that I could answer with. I love that line. I guess I'll only add that part of what I appreciate you doing there, which I try to do myself, is to see both sides of a story, to see both sides of things. Sometimes I've said to talk out both sides of your math and know that you are doing so because then it reminds me and it shows me that you and I are seeing a fuller perspective and then choosing our golden mean along with Aristotle, somewhere within that continuum, being able to see the left side and the right side of the spectrum. E., I feel as if you just embodied the very wisdom, the perspective that I've tried to have. But in closing on this one, yes, I love happiness equals reality divided by expectations. What it reminds us to do, as fellow humans, is to try to keep our expectations low because your reality might be the same, let's say no matter what, but if you had low expectations, boy, are you happy. You're like, this was so much better than I thought it would be. That I think is probably the best perspective to take as someone investing going forward, not just for years, but for decades. Don't expect too much of yourself or the markets, and you'll probably be pleasantly surprised over and over for a long time. I wish that for all of us. 

Rule Breaker mailbag item No. 2. This one, well, comes in many forms. I've taken two notes, cobble them together. They're great notes, they're very understandable. I thought, why not have my pal and Motley Fool Chief Investment Officer Andy Cross in to join with me to answer these questions. Andy, great to see you again.

Andy Cross: Hey, David, always a great privilege to be on your podcast. Thank you for having me.

Gardner: Thank you. This is your, I'm going to say, it's your 27th appearance. I hope it is as good as the first 26.

Cross: I hope so.

Gardner: Andy, I've got a note in here from Cliff [...], Cliff says, "Hi, David. I read your email about your new focus and wish you all the best." Well, thank you, Cliff. Again, you can imagine many people besides Cliff saying this, and there's a slightly different version of this, which we'll cover in a minute or two, Andy. But let's start with Cliff here. My question is, and you mentioned this in your podcast, so I hope you will indulge me. Cliff says, "You said you had a team of analysts that pitch stocks, but that you have the final pick. Well, who will do that now, or once you stop focusing on that? Will it be a voting system among the analysts, or is there a lead who will step in to fill your shoes?" Again, thank you for this question, all the best from Cliff [...]. Cliff, there are a few things going on in this question, Andy. One of them is just how things have always worked. Between Rule Breakers and Stock Advisor, they've been a little bit different, so I will speak to that in a sec. Then there's the concept secondly of individual versus team. Let's try to touch both of those bases, and let's start with the first one. I will briefly explain how Rule Breakers and Stock Advisor have worked. Andy, you will come on and explain how they are going to work.

Cross: Sounds great.

Gardner: We can do this? Let's do it. The way that Stock Advisor as the oldest service of all, has always worked is that for my side of Stock Advisor, I basically try to come up with four or five different ideas in a given month. I send them off to my four or five analysts who come back with research reports. I read through each of the reports and I decide I really like that fourth one. That becomes the next Stock Advisor stock or sometimes I don't like any of them. Good news, I've done the same thing the month before or three years before that, so I have a deep bench, you can think of as a watch list, so I draw that. Sometimes when my analysts come back with four or five, I like three of them, and so I've got good ideas for the future. For Stock Advisor, it's been me saying, "Hey, go out and research these stocks and we'll decide what." By contrast, Rule Breakers is a team-based service. I've had about five analysts or so including myself, and each month each of us comes up with some of our best ideas. Then I look over those five, and I decide I really like Tim Beyers's recommendation this month and so that becomes the new Rule Breaker. That is the past, that is the prologue, that is the basis of how we've done what we've done. Now, Andy, you as our Chief Investment Officer, have been involved in talking through how we want it to go. I have said, I can give you some ideas, but ultimately I want you and our company to decide how these services should work. I love all my analysts, just like I love all my children. Andy, let's start with Motley Fool's Stock Advisor. What is the process in place for Stock Advisor for my side going forward?

Cross: David, before I get into the actual process because we're still working through this and still evolving as you can imagine. I think listeners can imagine, those who know your track record as Stock Advisor and Rule Breakers, we certainly want to do our best to continue the winning ways and continue the philosophy that you have set in both those services, that has won for so many, for so long. It's very important for us that we continue to represent the philosophy that you set up in those services. The beautiful thing, David, is the way that you have worked with so many analysts on those services and we have rotated a lot of analysts over the years during those services including myself at various points early in my career. That's a real win for us because we have that body of knowledge that are familiar with your approach in your services. I will say the team approach is going to be carried out throughout both Stock Advisor and Rule Breakers.

Gardner: Okay.

Cross: Then we'll get to the decision-making too in a second. But we will be leveraging the analysts that you've worked closely with over the years throughout both Stock Advisor and Rule Breakers and that was very important to us, including to your brother, Tom, as we think about making sure we carry on that legacy. It will be really leveraging those analysts that you've worked with closely. Now, some of them, of course, have moved on to other things. Jim Mueller, for example, is now working in a different capacity, so he won't be part of that team. But we do have a few including as you mentioned, Tim Beyers. Specifically, that's the team approach when I think about carrying on the work that you've done at Stock Advisor and Rule Breakers. At the Stock Advisor approach, what we are doing is, Emily Flippen, who has been such a wonderful investor and analyst here at The Motley Fool and gone on to great success in lots of different areas, leading services and working on your services in different capacities: Blast Off, Marijuana Masters, Rule Breakers at various points. We've asked her to work with me at the Stock Advisor level to really help identify the best recommendations we think about every month, which recommendation best represents the philosophy of Stock Advisor to take over and carry on that legacy you set. But the beautiful thing, the way that we've set this up is she will be able to leverage the research from across the team, from the likes of Tim Beyers, Aaron Bush, Karl Thiel, Rick Munarriz, Alicia Alfiere, Tom King. Those analysts, David, that work with you, so she will be utilizing the research and the thoughts and the opinions of that team. But really every month, she and I will work to make sure that we get the best recommendation on your side of Stock Advisor.

Gardner: That's wonderful, and I love how people can't see you do this because you and I are looking at each other with Rick Engdahl's handsome face. We're all seeing each other over Zoom as we do this podcast, but not our listeners. I love how you were able to just rattle off those analysts' names one after another without looking over any list just because you work with them every day and you know them. I really appreciate that, Andy, and I want to say that team-based approach, that's the way I love for The Motley Fool to work. In fact, the Best Buys Now process which we're not really going to touch on today, but of course, Best Buys Now will continue with their process and be big features of these services. Those have always been team-based and voting-base with a lot of the names of the analysts that you just mentioned, and the others besides. It's always taken a village to make Stock Advisor and Rule Breaker happen. Emily, guided by you and supported by our team within Stock Advisor. How about with the Rule Breaker service, Andy?

Cross: In the Rule Breaker service, we've asked Aaron Bush, who's been one of the best investors that Motley Fool the past really since he started with us, has built up a wonderful track record and lots of different capacities. Then David, as you mentioned, Tim Beyers. Tim, Karl, and Rick, I mentioned those three investors, you mentioned Tim to kick us off, have really been with you in Rule Breakers, I think from the very beginning, and have been instrumental in identifying companies to help you recommend to so many members over so many years. You go back and look at their track record and it really is so impressive. We certainly wanted to keep them involved. Tim and Aaron will step in to help lead that team in a very similar fashion to the way that Emily will be doing it at Stock Advisor. Now, Rule Breakers has two stocks a month, two recommendations a month, we'll carry that forward. We thought we wanted to make sure we had the right people who know your philosophy, understand that and have developed track records and can work to identify both the recommendations and as you mentioned, the Best Buys Now. Aaron and Tim will be helping to spearhead that process and identifying those recommendations again with my oversight. But really those two, along with Rick and Karl and Alicia and Tom and identifying the recommendations.

Gardner: I'm so glad you mentioned that, Andy, because in fact, on next week's Rule Breaker Investing podcast, we're going to do Telling Their Stories, Vol. 3 and my two guests next week will be Aaron Bush and Tim Beyers. The two people who really have senior authority for succeeding me with the picking within Motley Fool Rule Breakers. Now, I will mention, Emily Flippen was on the very first volume, Telling Their Stories, Vol. 1, in March. If you're interested in hearing from Emily and from Rick Munarriz, long time Rule Breaker analysts whom Andy just mentioned. They both told their stories on the March 10th episode of Rule Breaker Investing this year. So, a lot of opportunity for our listeners, Andy, to get to know these analysts better. If you're a member of any real vintage and if you're a Motley Fool Live fan, boy, have you had an opportunity to get to know people like Tim Beyers and Emily Flippen better over these many months. I feel as if we're handing the baton here, and I do like the relay race metaphor to people that are very familiar to our listeners and certainly to our members. Before I let you go, I mentioned a second question. 

A lot of overlap here, but I'll just share Mike McAlister's question as well. "I've heard David speak on how he has a great team that's always been there, and will continue to be there to identify Rule Breaker stocks. However, I know David has the final say. Now that David will no longer be doing that, again, who will have the final say? I really hope that you will name a successor to David and not just do a team voting approach, and not have one individual responsible and accountable." Mike says, "I've always believed in the saying, split responsibility is no responsibility." While I certainly can see that perspective. Mike goes on, "My thought is you need to have one individual ultimately responsible for the Rule Breaker portfolio. Please let me know if there will be a successor to David's role of final say on which Rule Breaker stock gets picked, both new picks and Best Buys Now." Andy, what's your take?

Cross: Well, I appreciate Mike's sentiments around shared responsibility is really no responsibility. I will challenge that a little bit in a friendly Foolish manner. First of all, David, actually let me say that that is something both you and Tom definitely agree on is that we wanted accountability. Tom was very clear when he and I started talking about the plans and the investors who are in place and thinking through. I was supportive of really widening out the team and leveraging the insights from all the analysts, including our whole Motley Fool team, by the way too. We have a large investing team that contributes ideas and conversations in lots of different ways. Maybe not officially part of the teams over the years.

Gardner: Yes. In fact, we have a platform, we don't talk about it that often, but it's called Fool IQ, and it's an internal platform where dozens of our analysts share some of their most recent research and their opinions about different stocks and allocate to their favorites. That's been a wonderful, growing Fool story over these last five, six, seven, eight years, Andy. That'll be another example, probably, a lot of listeners don't know that that represents a real asset.

Cross: That's behind the scenes, although it just drives the full screen up. Then, of course, we have caps too. There's lots of different ways for opinions to get bubbled up, but you do need that accountability and that was one thing we agreed upon. We're still working through the exact processes to go through that, how much to carry on. We will carry on. A lot of the research, David, in the process that you've had in place over the years, but probably each investor is a little bit different, although they have their own tweaks to that. But it's my responsibility to make sure that we have the best investors we can put in to carry on that legacy for you, and also across all of our services to get the best investors to deliver for our members, but we will have somebody accountable and responsible for those recommendations. I will say there's a shared accountability for the scorecard though. It will be a conversation, maybe a debate, as we think about getting the best recommendations every month for Stock Advisor and Rule Breakers. But again, we will have a person there with me making sure that we feel really confident about the decision every month. But having that team based influence, I'll say, but a single person making the decisions.

Gardner: Thank you very much for speaking to that and all of these questions, Andy, this week. I really appreciate your leadership and the hard work that you've put it in. Again, it wasn't a surprise to our company at all that I will be transitioning my stock picking responsibilities, this has been in the works for months now. I do feel really good, of course, and I've said over and over both on the podcast, Motley Fool Live, and other places, about the quality of the people and also the design of the process that has led to these forms of succession for Rule Breakers and Stock Advisor. I love being transparent. I'm so glad that you laid out some of our processes, Andy, and also some of the specific names of the analysts. I'm delighted most of all by your continued leadership and oversight of this. You've helped me out a lot over the years and I know you're going to help out our analysts a lot too. Thank you very much, Andy Cross, and thanks again for questions like, Cliff's and Mike's, and I'm sure we'll continue to get more questions from people coming in over the months and years. But I hope the question actually starts to look pretty boring overtime because I hope we have the same good answer all the way through. Andy, thank you.

Cross: Yeah. Thanks, David. I hope we do too. I'm really excited about the investors we have, excited about the evolution, and certainly excited about the next steps in your career.

Gardner: Well, thank you.

Cross: Leaving us with such a great team to be able to pass that baton.

Gardner: I appreciate that. Again, a quick plug, next week, Rule Breaker Investing, we're going to have Aaron Bush and Tim Beyers tell their story. Many different perspectives. A theme of this week's podcast continues here then with Rule Breaker mailbag item No. 3, this one comes from Matthew [...]. Matthew, thank you very much for taking the time to write in. "Dear David, I've been listening to your podcast for a few years now without fail. Last week I finally became a Rule Breaker subscriber, only to find out today that you're stepping down. I'm still eligible for a refund, but I have confidence in the team as I feel I got to know them on the podcast." Well, let me just say again, Matthew, thank you very much. I have mentioned how you can hear our analysts tell their stories on this podcast. I also want to mention, if you think about, especially Aaron, but Emily, Tim as well, and others, they've distinguished themselves in other ways too on this podcast. For example, their excellence on the Market Cap Game Show, known far and wide. Back to your note. "Anyways, my question," Matthew says, "Is not linked to your departure or maybe ever so slightly. I'd like to hear your perspective on a topic I ponder a lot these days. That's the importance of planning for the future versus living today fully, in investing but also life in general. I think it will help if I briefly give you some of my personal context first, that explains the three main reasons why I believe this question feels more relevant to me today. My story starts in rural France where I grew up. Nothing extraordinary, two siblings, my parents were music teachers, and we had quite a simple, happy life. We never flew to far away places or stayed at fancy resorts, but we have long holidays together, and I had the best memories of camping by the Atlantic shore. We were taught to take care of our belongings and not to value flashy things. Somehow, I became really good at deferred gratification; the idea of keeping what you have rather than using it now is so fundamental to investing, to the point that I would often save chocolate from Easter for later, only to find out months later that it [laughs] had expired. My parents were not investors. Apart from buying our family house and saving to buy a new car now and then, I think the French safety net is the main reason for that because they had a job for life, and were guaranteed a decent pension, so no real need to build a big nest egg in these conditions. Next chapter, I'm now 18. My town feels really small and I can't wait to discover the big cities. Being good at school and in science in particular, I took up engineering and studied in Bordeaux, Nantes, and even in Blacksburg, Virginia. Not too far from you for a semester of grad school. Okay. Not a big city." Matthew says. He's referring, I think, to Virginia Tech, which is not only an excellent school for engineers and scientists, but also a pretty good ACC competitor of my alma mater, North Carolina. 

Anyway, back to Matthew, he goes on, "I interned in Paris. I found my first job in London. I started from zero, without hand me downs, but also debt-free, once again, courtesy of the French education system. Two years later, I moved to Dubai to work as a consultant for its home airline. It was, of course, the complete opposite to my small town, but I loved the energy, and having kept my values and priorities, I didn't succumb to the glitzy life. My salary would be split pretty evenly into four," and I really am impressed by this Matthew. "Four. One, rent; Two, normal life; Three, travel. After all, I had to make the most of the perks that come with working for an airline, and four, the last 25% to savings. Because I was going to have to build that nest egg living in a place with no safety net, but hey, also no tax, can't really have it both ways," says Matthew. Wow. A quarter of your salary to your savings and investing for the future. Of course, it's a neat trick, not many of us can play that, but it's certainly aspirational. Finishing up with Matthew's story, he says, "Now I've been in Dubai for 13 years. As mentioned, I'm asking myself how to remove that stress from constantly trying to optimize the future. I feel I'm on the right track to having a secure future, so then why do I feel the need to check the stock market every day, or to think about buying a fourth apartment in France when we just bought the third? No one wants to become the rich but stingy old person busier protecting their wealth than enjoying their life. As I mentioned earlier, I feel there are three drivers behind this question. No. 1 is maturity. I guess being older now, but also married with two amazing kids turning three and six next month, my perspective has changed. I want to make sure I can set them up right financially, but I also want to make sure I enjoy every phase of them growing up without missing out on the small joys: the tickled fights, playing Lego together, cooking as a family, etc. No. 2 driver behind this question is that my wife and I are one of the many couples created by this amazing melting pot that is Dubai. I married a wonderful woman from Uganda, which is far from home, but actually we have more in common than we have differences. Aside, the benefit is I have the best in-laws I could've hoped for and get along so well with her parents and siblings. We traveled there often pre-COVID, and along with my other travels that also gave me a different perspective. One aspect relevant for my question is that the risk of it sounding like a cliche, they aren't as stressed about planning every small detail about the near future and are better at enjoying the present. But then again, I'm an extreme planner," says Matthew. "Often after planning a holiday for a while, I catch myself on that holiday, absorbed in planning the next day, or sometimes even the next holiday instead of enjoying this one, how insane is that?"

"The No. 3 driver behind my question is COVID. I must start by saying, we're very lucky, all our relatives are fine, our own health is good. The kids don't seem traumatized. We kept both our jobs. It hasn't upended our life as much as it has that many others. But I think it has changed everyone's relation to time and the ability to plan with certainty and to the 'real priorities in life'. In conclusion, I know there is no magic answer, but I'd be curious to hear your reflections on the topic. I'm really glad you're going to keep up the podcast. I truly enjoy your style and coverage of investment business in life. Fool on. Matthew [...]." By the way, Matthew, I did my best with your name. I think I nailed it, but I did receive, unfortunately, a two out of five on the advanced placement in high school after doing pretty poorly at my school French. 

Well, that was a longer note and I shared it because I love hearing people's stories, especially ones that are really interesting to me. I love your background, both where you started and where you are now and everything in between. There's never enough time to capture in one mailbag item for a given podcast of mine all the best answers. But I'll give you three quick thoughts back, you and everybody else listening. The first is, I've always loved the idea of thinking backwards from the future. I first really came across this from Jeff Bezos when he was on our radio show a couple of decades ago, and he said, he uses a geeky phrase to make decisions in life and he called it his Regret Minimization Framework, RMF, if you want to make it an acronym. But the Regret Minimization Framework, which reads roughly like this, "Ask yourself, when you're, let's say 80 years old, looking back from then to today and trying to make your best decision today. You should be making one that minimizes any regret you will feel when you're 80." The reason I liked that framework is it's pretty loose. It's wide open. Some of the time it tells you not to do what you're thinking you might do or say. It reminds you not to do that. Other times, it emboldens you to say yes, I should do that because I sure don't want to be the 80-year-old looking back and saying, "My one-shot I never took." Bezos Regret Minimization Framework is an excellent one that I think you and I can use as a perspective to make better decisions and see are we living enough in the present? Are we taking enough risk? Are we taking too much risk? That's thought No. 1 for you. 

Thought No. 2, if you didn't get to hear me interview Shirzad Charmine last year on this podcast, just Google Positive Intelligence, Rule Breaker Investing and you'll get to hear a one-hour conversation with someone with a remarkable background who's made so much of his life coming from where he started. A lot of it is about getting to note ourselves better, himself better, and specifically, for each of us, are we sabotaging ourselves? Are there aspects of our own thinking that aren't even real? They are just in our brain. They are what you and I tell ourselves, you know the reason he did that because he always does that or you know the reason she said that is blah, blah, blah and it turns out that may not be the reason at all. It's just what you and I are telling ourselves over and over some times as we sabotage our own thinking. Instead of looking at things positively, I think it's so helpful. We got great feedback from the podcasts we did with Shirzad last year. I definitely want to have him back on the podcasts again this year. If you don't already know PQ, you can Google, look it up. You can even take a test and learn more about yourself. I feel like I'm throwing acronyms at you with my answer is RMF is the first and PQ is the second. Well, the third one isn't an acronym at all. It's just a reflection that a lot of our perspective and I don't speak to it that often on this podcast is probably linked to your spiritual life. Now a lot of us have different beliefs, but I would be remiss if I didn't mention that, thinking about that and what are your beliefs about an afterlife or not? Where is your personal thinking in terms of the bigger, maybe the biggest picture of all, why are you here? For a lot of us, I think it's important to settle some of those questions, or at least beyond the path or the journey. But I think that perspective maybe your SQ, if you will, your spiritual quotient that has to factor into the perspective that you have today and how you decide to do what you do if the RMF and the PQ weren't enough for you. Matthew, I hope those were helpful and I really enjoyed sharing your perspective on this week's podcast. 

Rule Breaker mailbag item No. 4, and in fact, this and the next two. The next three are basically all about different perspectives and I think a lot of us can relate to at least one of these. Here comes one from Trevor Knight, Rule Breaker mailbag, item No. 4. "Hi, David and The Motley Fool team. I've been wanting to write for a few months now, but watching Tom's new recommendation video today online prompted me to finally write more on that later. First, a little bit about my investment journey. I decided to get into stock investing in August of last year and subscribed to Stock Advisor at that time. I've also found your Rule Breaker Investing podcasts earlier this year and that's prompted me to become a Rule Breaker subscriber as well. I heard that others are working their way through the entire Rule Breaker Investing podcasts history and I've decided to do the same. I'm in November of 2018, so I still have a ways to go." Well, thank you for that, Trevor, wow. "I also want to say thank you to everything you and your team do with The Fool: the podcast, the articles, the discussion boards have been a wealth of resources on investing and the markets in general. Your podcasts especially have been a highlight for me and even though I'm on older episodes right now, it's been extremely helpful to hear some of these insights and think about how they can relate to the craziness of the current market. Well finally, regarding your brother's newest investment recommendation, I want to again say thank you to both you and Tom despite how terrible the current market has been to Motley Fool stocks. There's a lot of negativity out there and you guys are getting a lot of unfair heat sent your way. I've been spending more time on the discussion boards lately and to be honest, it sucks. People are upset. They're wondering why stocks in some cases have dropped 50% since their recent recommendation. If I really think about it," Trevor writes, "if I'd not been reading the philosophy, reminding myself of the long-term focus of investing. I know it shouldn't have said like that and getting constant reminders on the Rule Breaker Investing podcasts, I would also be panicking. I only wish that others really understood what they were getting into before they signed up for the Motley Fool and started investing. It's easier to say you are good with volatility than to actually experience volatility. Thank you to both you and Tom for continually reminding us that we are in this for the long term. That stocks do go up and down and sometimes down a lot. I can't imagine having now much patience to deal with people who clearly didn't read what the Fool is all about. Just as a little addendum, I'm also one of the people whose stocks are down and not just down to the S&P 500 nope, down overall. I'm not one of those people who got in on one of your good companies early, I'm right there with all of those who are complaining. Sure it's not fun, but I know that I need to focus on at least three to five years down the road. Anyway, keep up the good work. Fool on. Trevor Knight." 

Well, back in the Elizabethan courts, there were the kings and queens, there were the fools, and there were also the knights, and you sir, have written very nobly, I appreciate you sharing your perspective. Indeed it is the perspective of many who would just have started in the last few months, and yes, indeed, a few of my recent picks have lost about a third of their value and for anybody who's been around as a rule breaker investing listener, this has happened a few times before in the last six years. If you've been around as an investor of any real vintage, then you've seen it many times over the last few decades. I think it's really important to keep reminding everybody hearing me right now that one year in three, the stock market actually loses value, and often that value can go quickly. As I've often said in the past, stocks go down faster than they go up. But the good news is they go up more than they go down. Again, speaking up both sides of my mouth, you have to understand both of those things to succeed in the only game that counts, which is the long game, what we play as investors. Trevor, I know I'm preaching to the choir here, but you are right, there is a lot of, not just the world, but even new Motley Fool members who may not yet have that perspective. I think our perspective is rooted in two things primarily. One is the things that we knew before we started, maybe you heard good or bad things from parents about the stock market or money, or from a school, or a mentor, and then the second thing is our own lived experience, and there's no way to substitute for that other than being in the game and letting meaningful time pass. Certainly three to five months is never going to be meaningful if we're talking about the game of the stock market. Thank you for sharing your perspective. 

I wanted to put it out there because there are a lot of people who are probably disappointed with how bad some of our favorite stocks have been just over the last few months, and yet we've had invested in them for years, we will be invested in them for years more, and I think that's the important perspective. 

Rule Breaker mailbag, item No. 5, again, we're still here with different perspectives, that is the theme as I read Doug's note. "David, congratulations on your pending retirement." By the way, I want to mention, I'm not retiring, I'm just transitioning my stock picking responsibilities, Doug and everybody else. I'm still here with you every week on this podcast. I'm still Co-Chairman of the Company, Chair of the Motley Fool Foundation and Chief Rule Breaker, so all of this continues, but admittedly, I do have some new time for some fresh pursuits which I will eventually figure out what they are over the course of the next six to 12 months. Anyway, back to your note. "I very much appreciate it," Doug writes, "your wisdom as a subscriber to a Stock Advisor and Rule Breakers for the past six plus years. As a weekly Rule Breaker Investing podcast listener, you and The Motley Fool have greatly enriched me and my family. As a result of my financial success, I'm now financially independent at the age of 42, and will be retiring from a professional career later this month. I look forward to being present more in my family's life while my kids are still young. I also look forward to spending more time with my parents while they are still alive. I have much thanks to give to you for your overall investing and teaching over the years, and specifically the recommendations of companies like Shopify, MercadoLibre, The Trade Desk, Amazon, Twilio, DocuSign, Zoom, and several other multibaggers for helping me achieve financial independence at a young age. I wish you the best in your future endeavors, Doug." 

Doug, thank you very much for that note and I'm sharing it because very intentionally, it's fun to hear some of the stocks, some of the companies that have given you the dream of financial independence had admittedly early and wonderfully early age. Some of those very stocks are the ones that people are pulling their hair out about, somewhere around about now, stocks that have lost a third or more of their value, even though there is still way up from where they were years ago. The very same DocuSign stock that's down about 30% in the last few months, has helped Doug and others toward financial independence, and that's because of their different perspective, and specifically letting time pass, which is the most important perspective I think that we can have as foolish investors. It's fun when we remember that happiness equals reality divided by expectations. A lot of it is what were the expectations when you started. Admittedly with the stock market so hot in 2020, a lot of people had high expectations as we entered 2021, but the market giveth, the market taketh away, tide goes in, tide goes out, and all the rest. The good news again, it averages annualized around 10% return over time. Again, annualized, that's per year, which is amazing, and that's what I'm focused on with my perspective. Anyway, Doug, thank you for that note. 

Now, to finish out this short series on perspective in different timeframes, how could I not go to Greg Heller's note, Rule Breaker mailbag, item No. 6. "David, as you step back from your stock picking role of The Motley Fool, I felt there was no time like the present to thank you for my successes as a Fool. However, winners-wise, if you'll allow me to use the made-up word. " I will, Greg, thank you. "Winners-wise, I have had few to-date. You see, I joined as a subscriber in January of this year, first to Stock Advisor, then Rule Breakers, then Market Pass and even added Rising Stars 2021. As I'm sure you know a few of those investments are positive as of mid May 2021. But this letter is not for me today, it is for me ten years from now. Having gone back and listened to the last year of the show, having read and watched and listened to as much content as possible, not just from David Gardner, but also from Tom and the amazing family you have built at The Fool, I feel so strongly positive in my expected long-term results that I don't want to wait until 2031 to say thanks. None of us knows what will happen in the future, whether it be the stock market or one's health, or anything else that happens over time, therefore, thank you. Thank you for giving me a map to follow. For the rest of my and my daughter's life, I had a good 30-year career, I've invested since I was 18 years old, but I had run out of ideas. I didn't see a good long-run plan to do much with my investments going forward. Turns out that I purchased a handful of successful Fool recommendations, such as Apple and Starbucks over the years, those have both been wonderful Fool winners, but the eye-opening approach to investing has me so excited about the future. So thank you, David and Tom for starting something so special and continuing it long enough that this Fool could finally find you. Thank you for helping me generate returns that will carry me through the best years of my and my family's life. Good luck in whatever finds you over the next part of your life, Fool on. Signed 2031, Greg Heller." 

Greg, of course, I love the idea that you wrote the note, not now whether you had losers in your portfolio, we all do or winners, nope, you did it 10 years from now and you reminded all of us of the proper perspective, not just to take in 2021, but any other year. Thank you, Greg Heller, and thank you 2031, Greg Heller. 

Rule Breaker mailbag item No. 7. I'm going to combine a couple of notes for this one. They're both reacting to our company culture tips earlier this month with Kara Chambers and Lee Burbage. The first one is from PT Lathrop. PT writes, "Hey, David loved the company cultures series. Quick note, when you asked Lee about does this asynchronous work, work? He responded with, think about what sport you're playing." Just to fill those in who may not have heard that podcast, I was asking whether a new hybrid world of work where you're not necessarily in the same office with people that you're working with, you may not even be in the same time zone. You may have completely different rhythms. I was likening that to the idea of being in a crew shell and rowing together. It's hard to win many boat races if somebody isn't behind you paddling or somebody in front of you paddles asynchronously with you. Sometimes I've worried, the future of work, if it is async, may not be as efficient as many of us hoped for. Lee Burbage, on that podcast, countered with the idea that maybe it's not about a boat race, maybe it's more about basketball and knowing who's good at what and passing to them at the right time and people taking different places around the court. 

Picking back up with PT Lathrop, who writes, "Fair and valid enough, but I think it's more a question of, are you in the speed and quantity game or are you in the quality game? If the desired outcome is a fast or more finished product, the asynchronous probably fails to the competition. But if the value of the final product isn't generated from its rapid production and/or quantity, then asynchronous might fare well. I'm sure, us apostles never see the timelines on The Fool's projects. But as your biggest fan and content devourer, it's the quality of all your products and services that is truly your competitive advantage, PT Lathrop." Well, thank you for that PT. Similarly, Carl [...] reacting to the same podcast earlier this month said, "Hey David, I just finished listening to your podcast from May 5th concerning company culture tips. I just wanted to say that I've been listening to your podcast since the beginning, and I really appreciate these company culture-related podcasts. I'm an unemployed mainframe computer programmer with over 38 years of experience. I have worked for many different companies in many different industries. I can honestly say that the best jobs are the ones where the company leaders truly care about their employees. These jobs are few and far between. I just wanted to say that I envy your employees. I hope they truly understand and appreciate that they work for a very unique and special company with leaders that appear to truly care about their individual well-being. Keep up the good work, Carl [...]." 

Well, Carl, best wishes for your reemployment. Sounds like you have a history of being employed, so if that is your desire, I'm sure you'll get back there, and boy, if you don't have a great perspective to make sure that if you have a day with three different interviews, maybe take the one where they care. Fool on, sir. 

Rule Breaker mailbag, item No. 8, this from another perspective, as we continue perspective week, apparently on this podcast, and thank you very much for writing in Simon [... . "Dear David, thank you for all you share in your podcasts. My initial motivation in listening was to glean some investing wisdom. However, my motivation has shifted over time and I now find myself looking forward to each episode for the stories and the creatively thoughtful way that you approach any topic." Well, that is very kind, and thank you Simon, and I'll keep trying to do that well. "May I also salute your courage in seeking new frontiers as you step away from the familiar. Bravo, and thank you for still continuing the podcast. I made somewhat of my own life-expanding leap into the unknown, three years ago, at the age of 43, when I quit my job as a data scientist, working at a 'Tech for Good' company in London, and traveled to Southeast Asia with no plan aside from a desire to do some somatic work with people, [...] algorithms," Simon writes, "[...] human bodies, and explore myself in a different culture. I know your appreciation of quotes so you might find this one encouraging as I did at that time." This one's from the Alchemist, a book I'm sure many of us have read. Here's the quote, "'When someone makes a decision, he is really diving into a strong current that will carry him to places he had never dreamed of when he first made the decision.' These years have taken me to places which while in retrospect, seem natural. They definitely didn't always feel like that at the time. Like so many others, 2020 added its own twist as I found myself forced to transition from being a yoga and dance teacher in Thailand to primarily being a dog walker in Switzerland for 10 months after getting stuck there during a ski reunion with old friends. The funny thing is I now find myself living in an eclectic cocktail of all of these experiences as I'm now the CTO of a start-up bringing AI corrections into online yoga practice. I'm back in Thailand, working remotely, engaged to a Thai yoga teacher, and we have four dogs." 

Before I go on, let me just say both to Simon and many others who wrote in this week, and I hope you will appreciate this in light of my Weekend Extra earlier this month, I love reading the stories of people who are leading a more interesting life. Back to Simon's note, "I was planning on ending my letter here, but it now feels apt to share with you my own story with investing and the Fool. My first foray into investment was during my first year of full-time work after graduate school, the year was 1999. I had little interest in the subject apart from the desire for easy money. Boy, did I get burned in the dot-com bust so much so that I avoided any investing in shares until 2014 when after reading a technical post about how Netflix were training their machine learning models. I thought to myself that if I don't invest in this company, I'll regret it. Similarly, I then bought Tesla shares that same year after reading a blog series on Elon Musk and thinking, this guy's a winner. After a dozen more additions based purely on my own instincts about tech companies that I'd used either at work or at home, I wanted more structure and education in how to manage my portfolio and avoid the knee-jerk reaction that triggered me to suddenly sell my Tesla shares in 2020 for no other reason than because I didn't like his tweets. Coming across The Fool was love at first sight, even your name resonates with me. The tarot card that I most consistently pick in readings is the fool, a card often interpreted in a very positive sense." Let me just insert I'm not a big tarot card person myself, but I've always appreciated that the fool, I believe, is No. 0 when they put numbers on the cards in those decks, which I think is pretty cool. 

Anyway, Simon writes, "Being able to be a Fool and break rules had brought my own life such freedom and sparkle that I was over the moon to discover your advice, principles, and lists, teaching me how to apply this same spirit to investing and I now have a portfolio that strongly reflects my values. I'm more of a supporter of the fringe, so even though I expect Amazon and Facebook to do great, I prefer supporting Etsy and Pinterest and is as geographically diversified as the far-flung corners of the globe that have shaped my own being." Simon mentions Coupang, MercadoLibre, and Sea Limited all happily, he says, hanging out together in his portfolio. "More recently, I've learned how to take a deep breath and stay with stocks during downturns, much like one can breathe through the discomfort that can arise in a yoga pose until the body and mind unfurl to a new and deeper place of well-being. Fool on, David, and keep the podcast flowing as you explore and experiment over the coming year. Yours, Simon [...]." 

For that kind of a note, I find myself not really feeling like I need to add much. A lot of the notes we get for mailbag are often with questions where I feel a need to give an answer, but sometimes I just want to say something like amen, or in this case I would say, lead a more interesting life, and remember, happiness equals reality, divided by expectations. Thank you, Simon. 

Let's go on to Rule Breaker mailbag, item No. 9. This is back to a more technical question about investing. Thank you, Daniel J., written from faraway, New Zealand. He says to be precise, "Hi, David. What is a good time to stop starter stocks? I have been a Rule Breaker and Stock Advisors subscriber for around a year, and absolutely love both services. I've also subscribed to all of The Motley Fool's podcasts, and soaked up their back catalog, like a sponge. Using the information and insights gained from both services, I've steadily built up not only my portfolio, but also that of my two-year-old daughter. Love it. Over the last year of absorbing, trusting, and testing your guidance on investing, it's become not only an interest, but a passion of mine, one I hope to foster with my daughter in due course. Throughout this learning journey I must have really aligned with the Foolish philosophy as I noticed that 15 of my current holdings were included in the recently released Starter Stock list, included for both Stock Advisor and the separate one for Rule Breakers. 15 out of the 19 that you had on offer, is not a bad score," says Daniel. "This discovery certainly validated my abilities in screening, evaluating, and selecting quality stocks. But my question is this, when does a portfolio not need more Starter Stocks? Is there a guideline around this? Is there a Rule Breaker trade, a philosophy that I could lean in on to help in this decision? Thankful for your amazing services, I wish I had discovered The Motley Fool sooner, my daughter, sure will, sincerely. Daniel J." 

Well, let me speak to Starter Stocks, briefly, Daniel, and everyone listening. Starters Stocks are a list of stocks that we've created that we refresh and update annually for both Motley Fool Stock Advisor and Motley Fool Rule Breakers, and yes, the newest additions are out as of the last three to five weeks or so between those two different services, and each one features a list of about 10 stocks, that we call starter stocks. Now, here's what we mean when we say starter stocks. That is a list of stocks specifically curated as our best ideas and picks for people who are new to our service, who are new to investing. The mental picture I've always used as a skier is a green circle. If you are a snow skier too, you will know that the green circle slopes are the bunny slopes, they are the easy ones. They're flat and welcoming, nobody should get hurt there, and everyone's having a good time. While the stock market can never promise that, sometimes the stock market does hurt us and even bunny slopes stocks can get knocked down in bad markets. 

Nevertheless, if you think about a company like Apple, for example, over the years, that's frequently been featured on that list and understandably so, one of the largest companies in the world, one of the best brands in the world, a company whose consumer products many of us recognize and probably touch every day. That would be a great example of a starter stock. Now the starter stock lists are there to get started with. We want you to get investing right away, you don't need to wait for our next monthly pick and then you have to wait for another month before getting a second pick. We've always generously tried to provide you a platter of delights that you can enjoy right away. That's the purpose of the starter stocks list. Daniel and others, the intent is not, by the way, that those are just for beginners or rookies or only people who could ski on green circle slopes. That really is not the case, most of those stocks I've held for a long time myself and would add to them anytime. The idea is not at all that you could ever overpopulate your portfolio or somebody else's with starter stock. I just want to make sure you understand the purpose of that list and how it serves, but you also would understand then, that we're looking for great companies, that are a little simpler to understand and invest in, they're probably a little bit bigger, a little less volatile. You can ask yourself in each case, is this one I want to have in my portfolio? I think I'm speaking to somebody who knows how to answer that question for himself, and his two-year-old daughter. Thank you for writing in. 

Finally, this month, Rule Breaker mailbag item No. 10. This one comes from my friend, Sam Stevens. "Hi, David. It took me an extra week to digest your ten-and-a-half chapters podcast, as it truly was a rich masterpiece of everything Rule Breakers that you've built over many years. It actually made me quite emotional, listening to it, as it reminded me of just how much you and this podcast have enriched my thinking, and consistently brightened my day since its inception. While I'm sad to see you leave The Fool, I'm actually really happy you've made this choice, a very Rule Breakery choice, stepping away from the game when you're on top, and in your prime, is a rare, but powerful move, that places you in good company, Michael Jordan, Sandy Koufax, and Bill Gates, to name a few. Your announcement made me think back to my first experience with The Motley Fool as a high school student. At an elite private school in Washington DC, I was fortunate enough to be part of an investing club that got to take a field trip to Motley Fool headquarters. The connection was, that longtime Fool employee, and I will certainly say podcast personality Bill Barker, his wife was my English teacher. It was truly an awe-inspiring experience to hear a panel of Foolish all-star investors, David Gardner, Andy Cross, and Joe Magyer. Three legendary investors and teachers, I still can't believe you guys took the time out of your day to speak to us about the importance of investing, and getting started early. That afternoon made an impression on me, so powerful, that I can say with confidence that one afternoon is the primary reason I've developed a passion for investing in the stock market, started a career in the world of investing, including an investing internship at The Motley Fool, which I cannot recommend highly enough to any young listeners. Reflecting on my experience," Sam writes, "I think about just how fortunate of an upbringing I had to attend the school that I did and to be introduced to The Motley Fool and investing the right way at such a young age. I absolutely love the Fool's mission to help the world invest better, but back when I interned, in 2012, my only complaint, with what was overall and unbelievable company in The Motley Fool was that it felt like its reach was concentrated in folks who were already older and wealthier, could afford a subscription, had enough money to invest such that $10 commissions back then didn't prove an unnecessarily high barrier. At the time, I used to think about how so many young people lacked a good financial education and were completely spooked out of the market after the 2008, 2009 stock market crash. But how the world has changed, investing is now commission-free. The Rule Breaker Investing podcast has been a marvel, bringing a truly unbelievable track record of success for free to the masses, especially younger people who are more likely to listen to podcasts. I've actually kept my own Rule Breaker Investing podcast, five-stocks sampler tracker and by my rough estimation, you've beaten the S&P 500 by an average of 79% per pick with a 59% accuracy. In fact, if you'd invested $100 in every pick, that's $2,000 a year, that's $11,500 total. If you'd been invested in an S&P 500 index fund you'd have a little over $18,000, but with free Rule Breaker Investing picks you'd have over $27,000," and Sam includes a link to his tracker. Well, thanks Sam. "In closing, I'm excited for the possibilities you'll have, as you step away from running the Rule Breakers premium service to spend more of your time teaching and inspiring young people, especially those who are less fortunate than I was, too many today. Despite the additional resources out there on the Internet and the success of The Motley Fool, too many today still get led astray trying to get rich quick on Dogecoin or GameStop. I cannot wait to see what comes next from you and I'm very thankful, the RBI podcast, will still be a part of it. I count you among my top three heroes." 

Well, thank you, Sam, "in the world and I can't thank you enough for how much you've inspired me. Fool on." Sam Stevens, whom I enjoyed working with nine years ago, thank you. For this final perspective, shared among others coming from different places around the world, on this month's Mailbag, May was quite a month, I'm looking forward to June. But we're not there yet. Keeping things in perspective, and doing our best to live in the present, with at least an eye or an ear toward the future, I'm thinking back to Chapter 3. A couple of weeks ago, My Road Less Traveled in 10-and-a-half chapters. Sam, and I hope many others, you will know that chapter, listen to it again, as Two Fools. That was its title, and that is what we are. You and I, Sam. That's what we are, you and I, my many correspondence this week from Thailand or the French Coast of the past, or New Zealand, or Dubai and that is where we are. Dear listener, you, yes, you with an opportunity to spend a bit of time together each week along the stony path of life. My dearly departed mother left me a painting of hers which hangs in a prominent place in our house today. It's a picture of a Fool. She painted the traditional kind in cap and Motley entertaining young people seated in a circle around them, the motto painted at the bottom. She pulled this from a book, speaks well to us, and I think, my perspective here at the end of this week's podcast for you, dear listener, and for what we do together here at close, it reads, "This is the way that one in cap and Motley stops for awhile along the stony path of life to make you laugh." 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.