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That's right, if you were counting three, Jason's clearly the Motley Fool over-indexes in members named Jason, and so I've made the mailbag items number 1 and number 4 and number 7 in order to space them out and of course to make them the bookends for this podcast and the page-turning middle for this 100th mailbag. Before I get started, two items of interest. First, let me just say very clearly that there are so many and have been in our so many wonderful contributors via mailbags to this podcast, whether you are a one-off or wrote me four of them last year.

I have had so much fun with all 100 of our Mailbags. I'm very conscious that in identifying these seven people as superstars, I hope you, dear listener, if you've made a contribution in the past that you're proud of, I'm grateful for it too. I'm sorry that I couldn't have everybody on this week's mailbag. I know there's some clear omissions, just like the Oscars every year can't name everything a best picture. I could never manage to bring in all my favorite contributors but you're probably one of them, and no snub intended, let's dance together again sometime, soon. Item Number 2 of interest is this weekend's extra because this podcast, this 100s mailbag, is basically structured as a series of just like a mailbag, individual interviews with these seven special people. But I thought we could do something more.

What if we had a group conversation explored for fun, open-ended questions? It would make it too long for our weekly podcast. Why not make a weekend extra of it? Please join me with these special fools starting Saturday morning as you like, a weekend extra from Rule Breaker Investing is on tap because it's our 100th and how could we not? Let's crank it up. Let's get it started. Rule Breaker Mailbag, item number 1, Jason Moore. Jason Moore first came to our attention on the August 2020 Mailbag. He wrote, 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 12 of this year, again, 2020, that's four years later, Shopify was flying high.

Jason wrote 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 at last, Jason went on, it landed short by $1.50, closing with a gain of $38.50 for the day. Then the pandemic hit, and before ever tasting a spiffy-pop, we ate three Spiffy-Drops in eight days. Jason documented those dates but then said only eight days after that, and this is reminding me of the incredible volatility of March 2020. Do we remember it? Only eight days after that, Shopify finally popped as in spiffy-pop, and it has not stopped. A year later on the February 2021 Mailbag, Tinker, Tailor, Soldier and Sailor. I got to tell Jason's story through his own words. I just entitled that one winner. Jason also is the reason that Arthur Brooks was on this podcast last year he read, love your enemies, said you have to read this, have them on the podcasts and we did. Thank you, Jason, and welcome back to Rule Breaker Investing.

Jason Moore: Well, thank you, David. It is a pleasure to be here and to talk with all of you fellow Fools.

David Gardner: It's going to be a lot of fun this week and our Weekend Extra. Jason, let me start by asking you for a two-line bio.

Jason Moore: Well, sure. It looks like I am the only quirky Canadian outlier in this eclectic group, so I am very happy to be here representing us. I am now 44 years old, a few years on since Tinker Tailor, Soldier, Sailor, and I have two young kids of my own under 14 now. I officially have a teenager in the house so everybody else can help warn me about that. I'm just looking forward to getting into chat with this magnificent seven of your own.

David Gardner: Thank you very much, Jason and I thought about what are just three questions I could ask each of our guests on the mailbag, this special 100th Mailbag. I'm going to ask you these three questions first, and this is going to really form the structure of this podcast, Jason Moore, what's the best investment you've ever made and what did it teach you?

Jason Moore: Well, I was going to talk about NVIDIA and Tesla, and I figured some other people on this show are probably going to be better suited to do that. I am going to include something that I have only realized that I stumbled into investing in my early '20s and it was quite by accident. You can picture a 21-year-old, Jason, cluelessly throwing money into his company pension plan with 100% match, let me tell you

David Gardner: Awesome.

Jason Moore: Here I was thinking, it's just another deduction coming off of my gross nets stopping me from enjoying my life at the time.

Jason Moore: As it turns out now, looking back on that, that money that I was putting into that plan actually helped turn into a down payment for my first house, and it has been my longest running investment that I've had. After I've gotten to know a lot more about investing through this podcast and through a lot of other information, I look forward to seeing what that's like in another 30 or 40 years.

David Gardner: That is just fantastic. Using the power of compounding returns, there really is no substitute. The earlier we can get anybody we're connected to on that train making their first investment, Jason, I'm quite sure those two kids under 14, including a teenager, I bet they've gotten a start on investing. I won't even ask you much about that, even if you haven't started accounts for them yet, which I suspect you might've, starting the conversation is valuable on its own, so I love that answer and thank you for sharing that to question number 1, Jason, question number 2, how has being a part of this podcast community helped your approach to investing, to business or to life?

Jason Moore: That is probably my favorite question. This community has helped me in probably two of the main ways, investing in life, I'll focus in a little bit on so in investing, the ability to reach out and talk to all of the other members who basically can share some of the same common beliefs, but the ability to reach out and get different perspectives about them and different insights from them has just been invaluable as I've selected stocks and selected book recommendations, and selected all of the other things that I've done. Pursuing the areas of interested that I feel like a complete beginner in. When I came to Motley Fool, I really was a complete beginner in investing and going through the forums and going through the podcasts that were available to me, has just helped me out in innumerable ways.

David Gardner: I'm really delighted to hear that, thinking back to the decision to call our company The Motley Fool, which by the way, it wasn't much of a decision in the sense that we didn't think we were going to be a company. This is just a newsletter for our parents, friends, it was a lark, but I'm so glad now in retrospect that it was The Motley Fool, because I think we're all Fools. To think that you describe yourself as somebody who's just beginning, not really knowing much about what's going on. That's really, that's all of us. At different points we switch on in our lives and many people sadly, never do switch on. But I like to think that our name is a welcome that too. It sounds like it was to you and just the overall vibe of we're all Fools, we're all in it together. Please help me with my insurance decisions because I David Gardner never ever want to talk about insurance or have to make decisions there. But some of you know something about that and that was the spirit of the Motley Fool from our earliest days on AOL forums. Thank you for sharing that. Jason, my last question for you, looking ahead. What's one aspiration or goal that you have?

Jason Moore: You know, I'm a big believer in setting goals with intention. Every year I refocus in on the list. But I really decided to try and come up with something new as we were going into this podcast. It's something that I have thought about a little bit before, and I have now set the intention, so brand-new just for your podcasts, did David, I currently only have a bachelors degree and a minor in psychology. But I'm setting an intention that I want to turn that into a PhD in the upcoming years and it might take me 20 years to get there. But I want to really dedicate myself into an area that I love and to be able to examine it at that type of a level would just be something that I'd really strive toward. We know it's not going to happen by accident. [laughs] If James Clear has told us one thing, is that we need to be able to turn those into habits and put them into intention and so that's my intention.

David Gardner: That is fantastic. I think Jason, that you have read so well, you've read deeply into this area. Psychology is waiting for you my friend and I might be waiting for you depending on what's going on in my life, whenever you do get this PhD, I don't know if you'll be my psychiatrist, sounds like you'd be a psychologist. But I think that the world is waiting for you to get there. I think it's great whether it's five-years or 20, I know that you will, and it's such a great subject. Well, Jason Moore, Thank you very much. You were the lead off hitter for this our 100th Mailbag and again, for the reason that you were the one who said we should do this and thank you. It's going to be so much fun and you started us so well.

Jason Moore: Thank you very much. I appreciate it. And Rick, if I may so humbly suggest the title for your episode as too many Jason's.

David Gardner: All right, mailbag, item number 2, Dave Geck. I associate Dave Geck first and foremost with the wonderful story he shared with us that I've since shared multiple times on this podcast. It was on the January 2018 mailbag where Dave shared the story of how he started the habit of saving back in his military days, laying out his simple plan for how he did it and years later, blew away his friends and even his own wife when he revealed he'd been saving about 42% of his gross salary, 42% year-after-year, and how that's compounded for them. Now if you're a regular listener to this podcast, you'll also recognize David's a gifted storyteller who sends a notable quotables from time to time that I've been both delighted and honored to share. Thank you, Dave Geck and welcome back to Rule Breaker Investing.

David Geck: Well, thank you, Dave. I'm from Texas, 71 years old. I started investing when I was at West Point at about 18 years of age. I've been retired for 10 years now, worked for various companies. The last one was for 17 years at General Electric. I've been married 43 years, have two children and five grandchildren.

David Gardner: That is fantastic. Thank you for giving us a window into your life, 53 years of investing, Dave. Just fantastic. I'm not surprised you've been retired for a decade or so for somebody who got started that well and has saved so well. Thank you again for the stories that you've shared, which has just been my pleasure to share. I was checking Dave, the very first appearance you had on this podcast was in fact correcting me when David Allen, the getting things done author, had been on the podcast and I had briefly talked about how I have a pet peeve against the phrase life changing or people who say that changed my life because at the time and I even said this on air.

That isn't necessarily a great compliment because the only constant in life is change and so just for something to be life-changing says very little about it. I said out loud, life improving is, I think what most people mean when they say life changing. Then I went on to introduce David Allen, getting things done. I'm a huge fan on the podcasts talking about his life changing work for me and you called me out on that Mailbag just weeks later and I really do appreciate that Dave. Dave Geck, what's the best investment you've ever made and what did it teach you?

David Geck: Well, I guess I should say the best investment was spending the right amount of time and effort toward my marriage, which have fooled by wife for 43 years to stay married to me, but, since it's an investing podcast, I guess I'll do a little braggadocio and mentioned about in 2007, I invested $629 in Netflix and last checked is worth over 145,000.

David Geck: Then again in August of 2010, I invested $614 in NVIDIA and it's $236,000.

David Gardner: That is absolutely spectacular.

David Geck: Two important things on that is I believe is that following Tommy E's advice, Tom Engle.

David Gardner: Long-time Fool, Tom Engle, yeah.

David Geck: Yes. A little is all you need if it's great and a little is all you need if it turns out to be bad. [laughs] I've got many examples of the other one.

David Gardner: I'm so glad you mentioned Tom Engle, longtime Fool, hero to many. Somebody who's added so much value to our online site, especially the Motley Fool forums over the years. Tom has also been a guest on this podcast laying out his philosophy. Many people love that line, a little is all you really need if it doesn't work out or if it really does work out. What an embodiment of that dictum, you and your story are Dave, that's fantastic. How has being a part of this podcast community helped your approach to investing to business or to life?

David Geck: Well, to me it's been an extension, I guess. Going on graduation from first I was an avid participant in the newsletters and participant in the forums and learned so much on those, like I said, on the Tom E quote. I just jumped over, I guess. I'm not much in the forums anymore. I don't even know if they exist to tell you the truth. But I jumped over into the podcast and I'm a prolific participant of those and miss some of the ones like answers. One of my great bird was investing in Asia. But one of my favorite also now is the Australian one with the Scott Phillips.

David Gardner: That's wonderful, Dave. I'm assuming that part of the reason that you joined The Motley Fool in the first place, when you think about your initial reason was that you'd been doing investing for 30 or so years before the Internet ever showed up. What inspired you to come to fool.com and make contributions and you did under your screen named Doug Echo for years and years and that's how I really first got to know you. But do you remember what triggered that?

David Geck: Sure. It was easy to remember what it is because everybody has complained about it ever since and that's about the marketing. Oh my God, it's so horrible, but every time I would hear somebody say something about it, I'd say, well, fuck me. [laughs].

David Gardner: That's really funny.

David Geck: I think it was Bill Mann who said, "We're embarrassed by it, but it's the only thing that works. We've tried other things, but it just works."

David Gardner: Well, I've tried to speak to that some over the years. It's an eye-opener to me, what gets people to click and what gets people to take action online. A lot of it is often as each of you would appreciate, but once you see it from our side, it's just such an eye-opener, is creating some sense of urgency. Like by midnight this Thursday, you have to join or not. While it's certainly true, we could have had you joined that Friday or that Saturday, it turns out for humanity, each of us, that setting even artificial deadlines that are real deadlines really causes people to take actions. That's one example. But I really appreciate that. I've tried to speak to that some over the years on this show as well. Dave, let me close it out for now by asking you question Number 3. Looking ahead, what's one aspiration or goal that you have?

David Geck: Well, when COVID came, I got way out of shape and my aspiration now is to get back into shape and I've got two goals on that. One is to be able to bench press 90% of my body weight. I always considered 100% to be good, but 71, 90% is the goal. The other is to be able to do three pull-ups. Before COVID, I could do six pull-ups. Now, I can just about getting my eyebrows over the bar, [laughs] but we'll get there.

David Gardner: I bet you will. Dave Geck, thank you very much. We love setting physical goals. Our health matters I think even more than our financial health. Sometimes it's hard to remember that from one day to the next, especially if you're in a grind, but when you're retired, COVID comes along, it set us all back. I really appreciate you sharing that and I'm looking forward to whatever your next mailbag submission is. But for this 100th mailbag, that was very special, Dave Geck, thank you for being with us.

David Geck: Thank you.

David Gardner: Onto Rule Breaker Investing Mailbag Item Number 3, Jumm. Jumm first wrote into that same January 2018 mailbag that Dave Geck did, so that makes it historic on its own. But here's how I introduced it on that episode, which now makes me giggle and I think people will understand why. I'm going to quote myself here. Mailbag Item Number 3, I said in, January 2018, "This one comes from Jumm. It's spelled J-U-M-M, but Jumm kindly lets me know that it's actually pronounced like gum. First and foremost, he writes, this is my first email ever to your podcast. It's been long overdue. I've been a member of Rule Breaker Investing and Stock Advisor for the past several years and I have to say," and this is why I read this note, by the way, to Rick, my producer and anybody listening at the time because Jumm said, "I'm your biggest fan." Well, over the years since regular listeners have gotten to know first and foremost that Jumm is a she, not a he. It's not pronounced gum either and we have seen this fantastic woman embrace rule-breaking in her investing, in her profession as a nurse, and in her life at large. Thank you, Jumm, and welcome back to Rule Breaker Investing.

Jumm: Hi, thank you, David, for this opportunity. It's been an honor to be part of this journey with all of you because I started listening to this podcast in 2015, but it wasn't until 2018 that I started to write in.

David Gardner: You really have and thank you. This special 100th mailbag is not an invitation to all listeners to just spam me with mailbag submissions all the time. We get a good, healthy amount from one month to the next. But it is an invitation to share the quality that you that you bring Jumm, that each of our 100th mailbag contributors has brought. I'm so grateful for your contributions. Jumm, I've really enjoyed getting to know you and you're such a generous person as well. You've sent brownies to Fool HQ at The Motley Fool Foundation before. I wish every listener was like Jumm. By the way, who's not gum and not a guy. [laughs]

Jumm: I didn't realize you called me a he until the end. When I listened to it the second time, I was like, I need to tell him that I'm one of the female listeners out there. [laughs]

David Gardner: And you did it. That was helpful as we can now clearly hear. Jumm, how about giving us a two-line bio?

Jumm: Sure. As everybody knows, I am a registered nurse. I'm 48 years old this year and I was born and raised in Thailand. I started saving as soon as I started getting my first paycheck, I was working as a airline stewardess for Japanese airlines. That was when I was 20 years old, afterwards when I got my degree in nursing and entering in the workforce in 2008 is when I started investing for the retirement in the stock market.

David Gardner: That is wonderful and I know your present self is really grateful that your younger self had the vision to do that. Jumm, what's the, what's the best investment you've ever made and what did it teach you?

Jumm: Well, even though I'm going to talk about a specific company here but I have to get it out there that I believe my best investment that I've ever made was 20 minutes of my time listening to the Motley Fool ads. I [laughs] decided to join the Motley Fool service because that's when it led me to discover this one company and everybody listening here for a long time knows there was NVIDIA. It is still by far the biggest holdings in my portfolio. But the procurement has helped me grow my portfolio in the past eight years. The lessons that I've got from investing in NVIDIA. I have three lessons, then I'm going to quickly tie them together. Number 1 is never underestimate the power of luck, good or bad in life. Number 2, the importance of patience and long-term mindset. Number 3, how to build a portfolio that will allow you that patience. Because we're all human. When the stock market is going up and down, we would want to sell at the downturn. David, you recommended NVIDIA in 2004. It's not until 11 years later that I decided to invest in it. I was extremely lucky to be able to get the money in at the time. I didn't have to wait that long. But some investors have to wait two decades for it to prosper the way that it did. That reminds me of some time, it does take that long for something to become the successful investment. I would like to build the portfolio that helps me being patient and two things that helps me do that is that I have to diversify. I don't put money in one company. Number 2 is do not put the money that you need in the next 5, 10 or even 20 years, in this case, in a stock market. Those two actually had helped me stay focused and not panic and sell when the stock market downturn.

David Gardner: Classic lessons, things that we've said for many years and yet it's not that easy to follow them. Sometimes I'm conscious that when I say things like, "Hey, be playing the long game." It's easy to say. I truly believe if you make it into a habit and I believe this August group this week has done that. But for many people that's very difficult. I really appreciate not just that you say it, but that you've lived at Jumm and now you're telling us the story. My second question for you, how has being a part of this podcast community helped your approach to investing to business or to life?

Jumm: I will go with life part this time. I've always been an optimist and being part of this podcast is actually empowered me to stay that way. Because, you know, I tend to give people the benefit of the doubt and focus on the positive rather than dwelling too long on the negatives,. Because I've been called Jumm's so gullible. She thinks that the world is so beautiful and nothing things bad is happening. That's not true. I am well aware of the bad things that are going on in life and in the world. But I truly believe to be able to get past that and you have to be an optimist. Because optimistic viewpoint, well it's a source of hope. That actually gets you out of the seat and go out and do things and believe that things it's going to get better. You can just dwell in the pessimistic viewpoint because that doesn't really going to take you anywhere. I thank you all for your optimistic, loyal view. When you respond to the negative comments on the podcast or the guests from in the past, for example, Shirzad Chamine positive intelligence. That's really helped me is tanked and I believe that it is OK for me to be who I am. It's OK to be positive and optimistic.

David Gardner: I almost could just end the podcast right there because that's really what more could I hope for from an audio medium that just gathers us on a weekly basis. Jumm, that was beautiful. Thank you very much. Looking ahead, what's one aspiration or goal that you have right now?

Jumm: Well, as I have achieved my financial independence at this age, I know that I could not have done it alone or by myself. I have had a lot of helped along the way. Whether being my parents who themselves struggle with money, they actually taught me the right virtuals and the disciplines that are around money. My ex-husband shout out to him who has supported me financially while I go to nursing school and also being the person that started me investing in retirement. The Motley Fool community has played a big part in growing my wealth. I would like to continue to pay it forward. Thank you, David and Tom for creating the Motley Fool Foundation's. I think the foundation is a wonderful Rule Breaker in itself. Because, unlike the traditional foundation, for example, you donate money to shorten hospital, which is a wonderful things to do. The money goes toward paying for the medical costs or buying some medical equipment of some sort.

Jumm: The Motley Fool Foundation, expanding donations by giving it to a fellow Rule Breaker who's already on the ground working toward helping with fighting financial independence. If you are in the position to help, I would really encourage everyone to look into this wonderful foundation and also myself. I will continue to do everything I can to let everyone know that investing is my passion and if anyone wants to knowledge, I will be there to help and share the knowledge with them.

David Gardner: Well, you just did that and on a stage today that I'm proud of, that enables your voice to reach many. You've already been doing that, each of you by writing into mailbags these 100 months in a row. But Jumm, thank you so much that was a gift. Man, am I glad to have you on our team.

Jumm: Thank you, David.

David Gardner: Thank you, Jumm. You bet. Rule Breaker, Mailbag, item number four, Jason Trice. Jason Trice, I think first found us. We'll find out from where I guess, but maybe from Twitter. I'm going to ask him directly, but I do want to say that I don't think anyone has added more value to tweeting out and summarizing many of the points and frameworks via Twitter than Jason Trice who is by the way, @Jason_Trice on Twitter an excellent follow. I couldn't quite find that first-time Jason, that you interacted with this podcast, but for example, September 13, 2017, I retweeted a post that you had made and it was simply a few traits that @DavidGFool looks for to find in excellent businesses and there are seven. I won't go through them all here, but three of them are recurring revenue, considered boring, and high customer retention. The list goes on but the tweets have gone on, the support has gone on. Jason, I feel like you may know my frameworks better than I do and I'm really delighted to have you on this 100th mailbag. Welcome.

Jason Trice: Thank you so much for having me, David. That's a great question. I can't recall exactly when I first came upon the Motley Fool. I know it was from some advertisements and I eventually clicked on one and became a member. During COVID, I actually started listening to the Motley Fool live show and that's where I learned about your podcast and began to listen.

David Gardner: Well, thank you very much and I'm delighted to hear that. Jason, how about a two-line bio? Who are you? Where are you from?

Jason Trice: Sure. I am a long lifelong Texan. I recently moved to North Carolina and I'm a father and husband. I was thinking today back to my first investing. I actually started when I was 20 years old. It was I used money from my dish-washing job at Chili's and my dad knew that I would waste it if I took it back to college. He convinced me to put it in a Vanguard Health Care fund and I forgot about it, so it turned out pretty good.

David Gardner: It's a reminder and this has been proven many times. Brokerage firms will publish, occasionally studies or academics will pull their information and the brokerage firms invariably demonstrate that among the best performing accounts at those brokerage firms over years are the people who forgot they had an account and it's simply compounded over time and that is in direct contrast typically to the very active accounts that probably make more money for the brokerage firms, but unfortunately not for the people who overtrade them, so kind of love that. What was Chili's like as an employer?

Jason Trice: It was great. The food was my favorite part. I would work at double and I would have a half turkey sandwich with the chicken enchilada soup almost every day. [laughs] so yeah, I loved it and I got half price food.

David Gardner: I love it. Well, that probably wasn't the best investment that you've ever made, but what was Jason Trice, the best investment you've ever made? What did it teach you?

Jason Trice: I'm going to break the rules a little bit, but I thought if that's ever OK, it's on this podcast. I heard the term for the first time a couple of months ago, memory dividends and it brought to mind a moment in my life where I was making a career change. In my late '20s, I had the opportunity to accept a job in a student ministry for a church and it meant a pay cut and it wasn't going to pad my 401(k). There wasn't a lot of opportunity for advancement so I had some fears going in, but I accepted the position and I ended up working there for 11 years.

I was able to go on mission trips to Kenya and Guatemala and Jamaica and I was able to work side by side with students and their families. When I heard that term, it made me think of that position and those 11 years and there's not a day that doesn't go by where I don't think of a student or an interaction I had in Kenya or something from that time, and so it was just a reminder that there are so many ways to invest and financial dividends are great and I've been trying to pursue that was a lot in the last few years [laughs] But the memory dividends are also extremely valuable.

David Gardner: Love that. Financial dividends for those companies that pay them typically paid quarterly. Memory dividends sounds like those are daily and really appreciate you breaking the rules with that answer, Jason. How has being a part of this podcast community helped your approach to investing business or life?

Jason Trice: The rule breaker community has been very valuable to my life. As you mentioned, I've been tweeting my lessons and I started I think around the pandemic sharing. I was listening to RBI podcast and someone mentioned the Run for Glory, going back into all the episodes back to 2015 and I started going through those episodes and they were so helpful to me as I began my individual investing career and so I started sharing them on Twitter and it was daunting at first. I was afraid to send the first one. I thought people, my inner critic was very loud in saying that I had no business sharing these investing lessons. When I did, I realized how supportive the community is and so I say that the community helped me understand the power of sharing my perspective and that my perspective is valuable and on the other side of that, I learned the power of understanding other perspectives. I get caught in my own bubble and in my own head sometimes and this community is so diverse, all ages and backgrounds and countries. I've learned so much from just the comments that the community has given me and taking time to understand other perspectives.

David Gardner: Thank you for that. I know you've even spent some time with Fellow Fools, formed some friendships over the years, whether by Zoom or face to face. You're not the only one on this podcast, but I hope everybody will take advantage of the opportunity to learn from the people, the seven amazing fools that you're getting to hear from today. Whether it's just online via Twitter, on our Motley Fool forums @fool.com, certainly meetups. Our company does occasionally have meetings for members and those things, or even just dropping someone online saying, let's zoom it out, so thank you so much Jason, and you are an embodiment of that and looking ahead, what does one aspiration or goal that you have?

Jason Trice: My favorite podcast episode is the, Lead a More Interesting Life One, which is funny because it was an extra but I've listened to that episode countless times and it's encouraged me so much in my life. The reason I share that is there's a quote from a Matt Damon movie called We Bought a Zoo, and he talks about 20 seconds of insane courage. In the movie, he's talking to his son and he's trying to convince them to ask a girl on a date and his son is nervous and he's afraid. He says, "Sometimes in life, all you need is 20 seconds of insane courage." That's been something that has helped me in my life. I was asked by a mentor one time to speak in front of a group of 100s of people and I was terrified and so my immediate response was to say no.

He said, "You can say no, but in three months I'm going to ask you again and you're going to say yes." [laughs] Three months later, sure enough it happened and as I said yes and I got up and I spoke and it was a big lesson in my life too, that a lot of good things happen on the other side of our fear and a good way to lead a more interesting life is to go right at the things that scare us the most. I think my goal moving forward is to embrace the things that scare me. I'm thinking about the second half of my life right now and what I want it to look like and how I can lead a more interesting life.

David Gardner: Well, Jason, I think you've led a very interesting life and those memory dividends are reminders of that for you every day. I know you share some of those images and stories out on Twitter as well, which I've encountered. If the first half of your life was that I'm looking forward to seeing the second half, especially based on what you just said. I hope you won't take any crazy risks. I think there's something good about that 20 seconds, but maybe not 20 minutes sometimes, but wow, what a great example you are for each of us, and thank you for sharing that.

Jason Trice: Thank you so much, David. It's really an honor to be here.

David Gardner: Alright. On to the 100th mailbag Rule Breaker, item number 5, Adam Nelson. Adam Nelson has added as much value to this podcast as anyone I can think of. Quite simply, he improved the Market Cap Game Show with a simple and brilliant suggestion. That came on the January 2021 mailbag. It was Rule Breaker Mailbag, item number 1, it came from Adam Nelson. "Let's do it, Adam," I said. "Hi, David, " he wrote, "I really enjoy these episodes. Thought I might suggest a change after listening to the last Market Cap Game Show try giving the guesser," Adam wrote, "the ability to state a range of market caps and then their opponent can say, inside or outside that range " Adam went on, "This is similar to the old card game, acey-deucey, which is always a good time." I have to admit Adam, I never have played that card games, so didn't know it, but I get the concept and I really liked it. Adam went on to provide additional insight about how to do it. I went back to double check.

Over the years in this podcast, I have called Adam Nelson a genius, a great man, a brilliant listener, a hero among humanity. If you ever run for mayor anywhere you have my vote. Savior of humanity, hero to many, hero among men. All because of that winning tweaks suggestion he gave to our game show, which I described thusly, that one tweak when the skies opened and Adam Nelson spoke down to me about how to improve the Market Cap Game Show. Leading me to state that I will always lionize him no matter what he does or says on the show or in the world at large. I'd nearly forgotten by the way, that in November 2021, in a mailbag, he provided a full rewrite of Hamlet's classic soliloquy to be or not to be. It was entitled, Adam knows this but many will have forgotten or missed it to Trim or Not to Trim. Thank you, Adam Nelson, and welcome back to Rule Breaker Investing.

Adam Nelson: Wow, David, thank you so much for that introduction. I'll probably be replaying that for my children. [laughs] four or five times every night before they go to bed, so thank you for the opportunity to be here. It's one of the things I love about you is you make this whole thing fun. Enthusiasm is contagious and I just really appreciate that you share the credit and you have a great community here. I do love games and since I'm batting fifth and the order here, I'll try to clear the bases [laughs].

David Gardner: [laughs] You know I love that. Adam, how about a two line bio.

Adam Nelson: Sure. I'm 37 years old, so I graduated from the University of Washington in 2008 during the financial crisis, and with a finance degree. That was my first lesson that it's not really possible to time the market, including the job market. [laughs] I graduated from the University of Washington and then after that, married my wife now over 15 years. We've got three wonderful children, three daughters, ages 11, 8, and 5, and we still live here locally in the area.

David Gardner: Fantastic. Thank you for the background, the story behind the man. Are you listening, kids? Let me mention, by the way, before I ask you my question, which is, what's the best investment you've ever made, and what did it teach you? I was also reviewing another mailbag item, submission of yours, a few years ago, Adam. You just mentioned Shirzad Chamine and Positive Intelligence and how meaningful his work was for you. Now, that's not the first time Shirzad has been rocked on this week's podcasts. I'm pretty sure John mentioned him as well, maybe others. Adam, any thoughts to share now or reflections on why?

Adam Nelson: I actually did want to share something about that, but I was going to save that for your second question here, so I'll save that in the tank.

David Gardner: Beautiful. Sometimes, I start to do things out of order and break my own rules. Let's get back to it. Adam Nelson, what's the best investment that you've ever made? What did it teach you?

Adam Nelson: For me, there are financial investments, of course, but I think one of the lessons I've learned as I've gotten older is investing in relationships is incredibly important. So I was a bit unique in that when I was 20 years old, I invested in a diamond engagement ring for my wife. I think now that we're many, many years down the road, I can look back and say that was an incredible investment and I haven't wanted to sell or trim that. I've been holding this whole time and I think it's compounding incredibly. What I've learned is that those relationships do take a lot of time, an investment, but they compound over time, and I think that can be a really powerful lesson for people to take away.

David Gardner: Glad you articulated that. It's easy using spreadsheets and percentage gains annualized to say, very numerically, the benefits of compounding returns when it comes to money or other things that can be easily counted. But it has been born in upon me a number of times, you just did it once again that the compounding returns happen in all areas of life. The investments that we make of time and especially in relationships, those also compound. Huge benefits, probably not played up enough in the first nine years of this podcast, but you just rang that bell one more time, so I wanted to ring it along with you. Thank you. So well, said, Adam. How has being a part of this podcast community helped your approach to investing business or life?

Adam Nelson: I think the wisdom of this crowd is evident, and everyone that has gone before me here has really shared some wonderful stories. John brought in the point about Shirzad Chamine and his Positive Intelligence book, and the optimism and positivity that goes along with that is really powerful. One of the takeaways that I had from his story was the concept of who knows what is good or what is bad. Regardless of your religious beliefs, I think it's a powerful concept for each of us to understand that sometimes bad things happen, or at least they seem to be bad at the time, but they can turn out to be really good and powerful events in our lives and turning points. If you have that outlook in life, I think it will help for dealing with these things that come along and turning them into positives in your life.

David Gardner: Shirzad makes a real point of asking you to ask yourself, how can I make this a gift and an opportunity? That's sometimes in the face of the worst things that we hear or that could happen to us. I'm I guess fortunate enough that I don't feel like I've had to ask something really hard like that since having Shirzad on this podcast four years ago for the first time. But I know if and when those things happen, and they do, that is an incredibly beautiful question to ask and it's a powerful framework. Adam, thank you again for highlighting that.

This really does tie into our financial investing as well, because you often have to believe, especially when the markets inevitably give back sometimes a lot on a recurring basis. It'll keep happening over the course of our lives. I've always tried to make a gift or opportunity that by just not paying too much attention. Rather than geek out over my portfolio where it is these days, I tend to spend more time outside or with other people, I just ignore. It seems irresponsible, but I've gotten good at ignoring bear markets and I feel like it's both psychologically healthy, but it is a way to turn some negativity into a gift and opportunity. Adam, looking ahead, what's one aspiration or goal that you now have?

Adam Nelson: Well, listening to everyone else speak, I would like to have more of those very long-term big stock portfolio winners, of course, as the years go on. I'm fairly young, but i have decades ahead of me where I can hopefully have some of those. One of the reasons for that I think is to share that with my family, with my community, and pass along some of those lessons to my kids. But related to that, what I aspire to with my kids, they're 11, 8, and 5, I think it would be really cool someday to play a round of golf with all three of them altogether. I think that's a long-term vision that hopefully it can become a reality, and maybe we do at somewhere exotic that I haven't been to. I haven't traveled as much in my life as I would like to. Living an interesting life, I love that concept as well, and I've done a lot of things and have a lot of hobbies, but i haven't traveled as much, so I would love to share that with my family, maybe play a little golf, have some more fun. That's a definite goal for the next decade.

David Gardner: Well, you've said it now, so it has to happen, but it was probably going to happen anyway because as we start to live into the things we're thinking and actually sometimes take that 20 seconds of courage and just race forward and go for it, we surprise ourselves sometimes by how much we become more of ourselves and the things that we thought we would be, the things that we said we would do, especially in front of tens of thousands of people listening on this week's podcasts, so the kids have been forewarned and it sounds amazing. Not if and when that happens, I hope you'll share out a picture that we could drop through our Motley Fool feed at some point, whenever that does happen.

Adam Nelson: I'd love to.

David Gardner: Adam Nelson, thank you so much for being a fellow fool.

Adam Nelson: Thank you, David.

David Gardner: You bet. Rule Breaker, Mailbag item number 6, Mike Mcmahon. Mike Mcmahon has been adding a lot of value across the Motley Fool, especially in our interactive spheres like, like Motley Fool Live. That's the TV channel that runs on our website for our members. This particular podcast and his mailbag submissions and his contributions on Twitter. Those are just the things that I know. I know there are a lot of other things that Mike cares about. I hope we'll learn a few of them right now. I first saw Mike write to this mailbag, I think it's March of 2022. He was reacting to the previous week's Market Cap Game Show. Mike asserted in that mailbag item, he said, listening to the Market Cap Game Show, I found the best outcome is just to always stay outside the range, especially for obscure companies.

Perhaps the scoring should be modified, Mike suggested, to award a full point for agreeing to within the range, and a half point for outside the range, and then another half point for correctly guessing above or below the range. As I thought about those, and I think I said this at the time, it made it a little bit more complicated than I want the game show to be, but I got Mike's point. Anybody who is looking for a pro tip, it might in future appear on the Market Cap Game Show, heed his warning and his advice. Mike Mcmahon, welcome back to Rule Breaker Investing.

Mike Mcmahon: Thank you, David.

David Gardner: You are the one who suggested in our notes and week leading up to this podcast that we make sure we have a little bit of a bio from each of our members. Mike Mcmahon, may I ask you for your two liner bio?

Mike Mcmahon: I'm 60 years old. I joined a company in 1979. It was a retail or West Coast retail that was part of Dayton-Hudson at the time that became Target, so it was a 30-year career with a Fortune 50 company. During that time, they had a 401K program that allowed me to start saving in 1985. For that 25-year period, I was able to make contributions so that 401K, so I've always considered myself a saver, even though you rarely had investing options and weren't really per se investing.

The company spun out from Target because Target needed to be more return on investment type of people, so an LBO bought out the company, and we ended up going bankrupt because as the result of the great financial crisis. In essence, my business career ended in 2009. For the last 10 years of that, I, in essence, was just being a contractor, doing minor things. I found a private job at a local golf course. That's when COVID hit in 2020. I was in the pro shop and I got kicked out of the pro shop because it closed and started joining Motley Fool Live programming, hence the name Pro Shop Guy, and I've been doing that for the last three years.

David Gardner: Thank you for a window into the life that you've led thus far. Mike, do you have any big takeaway reflection on Target or that time?

Mike McMahon: I think the biggest takeaway I have is the fact that the company that I originally worked for, which is what's called Mervyn's was a West Coast retail. They were born out of the ability to say, provide retail to the baby boomers, and successfully built on that whole model of providing value to companies or families that were restricted. But if you look at all the history of retail, we over-retailed throughout the '80s, '90s, and 2000s as a result, I think it's just a natural progression of e-commerce and everything else that squeezed all these companies like Sears and Pennies and [inaudible] .

David Gardner: Thank you for sharing that. Clearly, pattern recognition that you'd built up over decades. Most of the rest of us who don't know much about that industry, myself included, wouldn't have thought of it that way, but over-retailed, that's very interesting. Maybe even more interesting to me though Mike is what's the best investment that you've ever made and what did it teach you?

Mike McMahon: I would say initially it would be the postage stamp that I invested in buying the Christmas car to reconnect with a college girlfriend who then became my wife of 43 years.

David Gardner: That is phenomenal. Do you remember what the postage stamp looked like?

Mike McMahon: It was a standard issue at the time. It was in 1978. So you'd have to adapt to scholar that back. [LAUGHTER] The second thing I would say in terms of investments though, is beyond, once again, I really didn't consider myself an investor until the pandemic would be any investment in myself per se, in the personal development space. There's never been an chance for me to turn down buying a book, and as a result, I've collected a vast number of books over the 40 years of reading that I've [inaudible] . I think that's another compounding effect that occurs.

David Gardner: Bib Leo Fillia, it can be expensive. Not just in dollar terms, Mike, but it takes up some space. Are you able to fit it all?

Mike McMahon: That's source spot with my wife. [LAUGHTER] What are you doing with all these books and why not [inaudible]? So of course then again, technology saves the day with Kindle and our comments and our mailbag suggestions about read wise and being able to now store everything, get you in case [OVERLAPPING]

David Gardner: Love it. Mike McMahon, how is being a part of this podcast community? But I might even say the Motley Fool community more widely because you are very much identified by many Motley Fool Live fans as a regular supporter and contributor. I think you're a contractor to our company now as well, so thank you for that. How has this experience helped your approach to investing business or life?

Mike McMahon: I would say that the fact that when I retired, forced into retirement as a result of the pandemic and then joining Motley Fool Live community, as well as then, as Dave pointed out, going out and exercising, I started listening to podcasts. I take it two and a half hour walk every morning and listen to podcasts. It wouldn't have speeds, so I get over 20 hours of podcasts,

David Gardner: Oh my gosh. Wow.

Mike McMahon: [inaudible] regular rotation, I look forward to every Thursday morning being able to listen to the various different stylized programs that you provide us gives me food for thought and an opportunity to look at the world through a different set of eyes, and that's what I tend to think of most value or get out of.

David Gardner: You've just opened my eyes and I think everyone listening two and a half hour walk every day. In some ways I imagined it's only possible that if somebody is retired or semi-retired, although maybe there's somebody who can just like do conference calls and walk around for a couple of hours every day. But wow, what a wonderful habit to be in in retirement or semi-retirement and something that we should all aspire to. I always love meeting people who simply break the molds that I imagined were set forth for all of us based on how we're living our lives. That is a phenomenal contribution to your health and longevity Mike McMahon. Looking ahead, what's one aspiration or goal that you have?

Mike McMahon: I think that the fact that I truly believe I've got another 25-years to go, and so I actually just begun my investing career, as I pointed out, basically 401K program that basically allowed me to create a large amount of money that when I retired, I was able then to take and turn around. I had portfolio basically EFTs and mutual funds or it was as a result of the pandemic that I said, let's try the stock market thing and Motley Fool Live as well as your podcast [inaudible] gave me an opportunity. I completely transform my portfolio from safe and sound ETFs and mutual funds into over 150 company stock portfolio.

David Gardner: Love that.

Mike McMahon: Which is my starter fund that I've got 30 years to go through, in my opinion, so it's been fun.

David Gardner: Just getting started 25 plus years ahead, planning and investing for the future. What an inspiration, Mike McMahon. Thank you for joining us on this 100th mailbag.

Mike McMahon: You're welcome.

David Gardner: Rule breaker, mailbag, item number 7, last?

Adam Nelson: But not least.

David Gardner: I'm not going to say the other thing, but not least, Jason Newman, no one has written more good notes over more years to this podcast than Jason Newman. I first got to know Jason years before podcasts were even a thing. I think it was in New York City book signing in the 1990s. Jason's first appearance though on this podcast was the first year of this podcast. It was October 28th of 2015. The title of that podcast check at Google and listen to it, enjoy it. It was seven principles for all true investors. I'm going to quote what I said then as I introduced Jason.

I was reading a great post on our discussion boards on Motley Fool Supernova this week by one of my favorite Fools. His screen name is CMF, Jay New. CMF, by the way, means Community Motley Fool because Jay assists as a volunteer in our community. He's that passionate about investing. He's very successful outside of what he does at the Motley Fool is a media professional. Today, he was talking about the portfolio that he's built up using Motley Fool services. He has 90 stocks in it. Jay's not right here with me, I said on that podcast nine years ago, Jay is not here with me and I'm not interviewing him right now, but I'm pretty sure he didn't expect to have 90 stocks when he started investing a decade or so, which is by the way, more like two decades or so now ago, but now he has them and he hasn't been three buckets.

He's got the ones that he's very confident about, and then on the opposite side, the ones that are much more speculative or maybe out of favor, and then of course, the middle bucket in between. But he's taken the time to massage it into a meaningful whole, where he's got three buckets. But it's 90 stocks and this is a guy who is still pretty young and life with a lot of earnings potential going forward and a family to support. What a beautiful position. What an aspirational position for most of us to think that by the time we've just cracked 40 years of age, we have 90 stocks.

David Gardner: Jason Newman, you are actually here this time, welcome back to Rule Breaker Investing.

Jason Newman: David, thank you so much for having me. It is such an honor and a pleasure to be here on behalf of your August audience with this group of Fools.

David Gardner: You really were one of the early correspondents before we had Mailbag Jason, I was already sharing some of your story because, for me, you are the whole package. You're somebody who is an investor, but as Warren Buffett says, I'm a better investor because I'm a businessman and a better businessman because I'm an investor, maybe my favorite of all Buffett lines and as I got to know you now 30 years ago, I saw that in a much younger Jason Newman back then and I know you're a successful family man and a good friend to those who get to spend much. More time than I do with you but what a delight it is to have you on this podcast, Jason, what's the best investment you've ever made? What did it teach you?

Jason Newman: Well, with an honorable mention to my family and my friendships as mentioned before me and with all due respect to my investments, my first investments in Apple in 2003 and Netflix in 2007 and Tesla in 2011. Shortly after you all had Elon as a guest at Fool HQ, I would have to say it was the time I took to read you have more than you think by David and Tom Gardner in the late '90s. Shortly after that, the $2 bus fare I paid to go see you guys at that Barnes and Noble, that was September of 1999.

David Gardner: Thank you for that.

Jason Newman: One night after work. At the risk of bleeding into my answer for the next question, I would say it's the time and money that I invested and I'm not not being paid to say this in my stock advisor membership back then and to become part of this wonderfully Foolish community that you and your brother and so many, countless Fools have built. The friends that I've made along the way on the message boards at member events, at local gatherings, at moments like this and so that's by far and away, more valuable to me than any of the investments I've made in any one stock.

David Gardner: Well, thank you very much for that and given the low cost bases, I think you have some of the best companies in the world today. That is quite a statement and I really do know that sincere and receive that in the most enriched, happy manner. Thank you so much for that, Jason,.

Jason Newman: Thank you.

David Gardner: You're so welcome. You mentioned that that might bleed a little bit into your answer to my second question and now that I'm getting to ask it for a seventh time this week, I think you know what's coming, but how is being a part of this podcast community helped your approach to investing or business and or life?

Jason Newman: Well, at this point, the Motley Fool is part of my DNA, is part of who I am. I think if you talk to any of my friends and family outside the Fool community, they would tell you the same thing. To me, Rule Breaker Investing and all of the other Motley Fool podcasts, I've just been that constant reminder that there is more to investing than money and gains and losses in stock tickers and so on and so forth. It's the insights that I get from the other Fools on this call and countless others. It's the relationships that I've built through communicating with other Fools who also happens to listen to the podcast and Twitter and social media have been an incredible catalyst for all of that. I would just say it's that and then it's the constancy David. You are so humble and you'd probably never say this, but we're celebrating the hundredth mailbag. That means for 100 straight months you've been at this. You said you were going to do it at the beginning you've done it and it's like you said earlier, it's one thing to say it, it's another thing to do it and here we are a 100 months later. It's just that constant reminder it's that drumbeat

David Gardner: Well, thank you very much for that, Jason and I think that just as we talked earlier about compounding returns and the importance of that, not just financially, but relationships and the time that we invest. I love the things in the world that I can count on, I like the dependable, the world is crazy and sometimes for very understandable reasons people bail in that situation or they can't make the thing and they let you know just beforehand and I'm sure I've done that to people in the past and will in the future but really I do love the things that we can count on, the things that recur and I'm really glad I didn't say best for last and I don't feel that way because I love each of our contributors and the many that didn't get to be on this week's podcast who are every bit is worthy as any of us but I really appreciate especially Jason that I close with you because we have the longest association of my friends this weekend and thank you I value that back. Jason Newman, looking ahead, what's one aspiration or goal you now have?

Jason Newman: This is the one question I gave the most thought to, and one aspiration that I've always had since I started investing 25-30 years ago now, has been to journal. It's something that countless Fools have encouraged all of us to do and I'm so guilty of just never having done it and I've tried and I've started and I've stopped. What I started doing actually, ironically last month, is I've taken the statements of the portfolio that I began about eight years ago or so for my children and I've started my oldest, I think you know this David, my oldest son, has really taken an interest in investing of late. I've given him more and more peek under the curtain of what's there for him and so I've started taking the quarterly statements for his portfolio, and I've begun journaling next to each ticker, my thoughts on that company at that time. It's an excuse to journal, it's an excuse to teach him and I aspire to continue to do it, whether I will or not, remains to be seen.

David Gardner: Well, you're already doing it, so there's no substitute for continuing what we're already doing, turning them into habits. That's a wonderful gift and I will say having passed a portfolio onto three now adult kids myself. You went up to me because I don't think I provided them notes next to each of the positions, but that really is a great idea and for those who purpose that and make the time for that it's very valuable.

I know that our friend Mike McMahon, with whom we just talked, wrote into the mailbag just within the last year or two about the power and importance of journaling something Mike has been eloquent about which we shared through more than one mailbag over the last year or so. I think that were among friends, very good company to hang with and I'm not trying to title this week's episode, but I think that this 100th mailbag has given you and me, dear listener, you and me, some very good company to hang with and I want that for each of us in life.

Six degrees of separation as a concept many of us know about the ideas each of us is tied to every other person on earth by six degrees I know somebody who knows, somebody who knows that person knows that and you do that six times and you can touch almost everybody and I would say, even in the age of the Internet, maybe it's down to five. I'm not an academic researcher myself, but I wouldn't be surprised if six is shrunk to five, but a lesser discussed in this case, three degrees is the concept of cultural influence and that is that we are all influencing three degrees outward from ourselves.

Concentric circle, your partner, let's say concentric circle out from that, the person they work with. One more concentric circle out from that, that person's cousin. My wife's coworker's cousin helped me start working out in 2024. No one can actually say that because you don't know that, but it's real because we are social creatures we share it out, we share out the good and we share out the bad. I've always done my best to try to surround myself with as many good people as possible because then I know I'm being influenced directly and likely influenced indirectly in ways that can never appreciate that remind us all that no one has self-made, that we're all creating each other every day.

My wish for you dear listener, staying with us through this special, this memorable 100th mailbag I have to wishes the first is, I hope that you are inspired by the good people that you got to spend time with this week and second, I hope you'll join us for our weekend extra. We don't do this very often, but we're doing it this week. I'm just going to ask a few open-ended questions of this wonderful crowd and hear back some of their impressions that will come your way Saturday morning. It won't be that long, but a little bit more along some new angles from this wonderful group of Fools. There it is, a hundred. I sure hope it was worthy of the 100th consecutive Mailbag episode. I know one thing my guests were worthy. I don't know whether I held up my end of the bargain enough, but if I didn't, I hope you suffered this Fool gladly. I shorted love spending this time, this particular week, this particular month with these seven people and an eighth. You thank you so much for joining us. Fool-on.

David Gardner has positions in Apple, Netflix, and Tesla. The Motley Fool has positions in and recommends Apple, Netflix, Nvidia, Shopify, Target, and Tesla. The Motley Fool has a disclosure policy.

"Rule Breaker Investing" Mailbag No. 100! was originally published by The Motley Fool