So You Want a Career in Finance?

How do you get started with a career in finance? What about a career in financial freedom? Discussion of these questions and more in this mailbag episode of the Rule Breaker Investing podcast.

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

This video was recorded on September 28, 2022.

David Gardner: You want to get started with a career in financial services or investing, or financial freedom. Maybe you’re middle-aged and considering switching into our field, throwing away your collar, blue or white, in favor of a Motley cap. Well, if this is you, glad you asked because a few others did too this month, which is why here at month’s end in your Rule Breaker Investing mailbag, we’re going to speak to that, these things plus a visit from my Rule Breakers team and other sundry delights and treats only on this week’s Rule Breaker Investing

Welcome back to Rule Breaker Investing sundry delights and treats. I think I just said a little while ago. Reminds me of The Lion, The Witch, and the Wardrobe. Do you remember Edmond? Do you remember the white which, and do you remember the white witch offering Edmond Turkish delight? I don’t think I’ve ever had Turkish delight. I don’t think people talk about it much anymore, but I did do a little research. Apparently, it’s absolutely delicious and it’s not that easy to make. Anyway, various sundry, sometimes Turkish, delights and treats await us on this month’s podcast. This is your Rule Breaker Investing mailbag. To see where we’ve been this month, we kicked it off here in September with “Pet Peeves Volume 7.” My most self-indulgent, truly one of my favorite podcasts to do every year, but we only do it about once a year. It was this month. We followed it up with a “Review-a-Palooza” episode of two five-stock samplers, and then of course, last week was “The Market Cap Game Show” with a new rule, no spoilers, although really you should have listened to it by now.

But if you haven’t, you should go back and play. Which had an 11th stock included for the first time due to our new tiebreaker rule which we actually had remarkably to invoke. Let’s just start it this month with some of the hot takes from Twitter as I like to do, and let’s start with the “Market Cap Game Show” at @OtherMikeSteele, you wrote, “The shorter intro and faster jump into the game is a great improvement. Whoever suggested that is a genius.” It’ll be our little secret, Mike, who suggested that. Next, Gaurav Kumar @GauravKInvestor tweeted, “This was the best market cap episode to date, and yes, I have heard them all, going back to the first.” “The reference to Etsy,” Gaurav writes, “was the best part.” Ybmscr @ybmscr on Twitter, thank you for this. “The whole game,” you tweeted “is always awesome, probably because of its scarcity as you say, but there’s for sure a different level of excitement on the Final Jeopardy-style question,” also known as our tiebreaker. Ybmscr continues, “I wonder if there’s a way to always incorporate it so that we can have one even if there isn’t a tie.

It’s also the one question we’re choosing a range size is a lot more than just playing mind games.” You and I replied back-and-forth on Twitter about this, and I ended up so agreeing with you that going forward, the new format of the Market Cap Game Show, it will receive yet another tweak next time. We’re going to do what we did with the tiebreaker twice during the regular game. Kind of lifting another page from Jeopardy where you have a daily double, I will randomly be invoking that tiebreaker rule we won’t go into it. For those who don’t know what I’m talking about, you have to go back and listen to last week’s podcasts. But we’re going to invoke that tiebreaker within the normal body of the show for two of the 10 stocks. Randomly chosen, I know Rick Engdahl, my talented producer, will have some new sound effect for when that happens. We’ll try not to steal too much intellectual property from the people at Jeopardy.

Anyway, I totally agree with you ybmscr, and thank you Sam Stevens for the Stephens sudden death rule, which is about to become a regular feature. Not every question, just a couple of special times during the show for future Market Cap Game Shows. A few other tweets. Reacting to my Pet Peeves episode @KerryPrep. I was talking about astrology at one point in that episode. @KerryPrep writes, “For decades when approached with wide-eyed eager anticipation of a response when asked, “What sign were you born under?” my answer is, “A stop sign” A fellow wag. Two tweets speaking to our back catalog. We certainly take some pride on this podcast as a community for the value of many of our past episodes. If we were a news podcast, I would not encourage you to go back and listen to what we were talking about last week, let alone seven years ago. But as we are not a news podcasts, we are an advice podcasts, we’re a storytelling podcast. We’re an investing podcast. I do think our back catalog is valuable and I’m glad to hear you feel the same way @Mr_JMVela7 who tweeted this month, “Thanks to an interview with @JamesClear on @RBIPodcast I read Atomic Habits. This book really is life changing. I started creating new habits where I had been struggling for years. Do yourself a favor and read this book. Thanks @DavidGFool.”

Well, thank you @Mr_JMVela7. Of course, thanks again to James Clear for appearing on the podcast a few years ago talking about his wonderful best-seller, Atomic Habits. Jason Moore, @JimminyJilickrz, you wrote @DavidGFool and @TylerReber there even better than the pitch. Now, what is Jason referring to? He’s referring to a visit from a full techie named Tyler Reber came on last month, and Tyler, in addition to answering a mailbag item on last month’s mailbag, also, I got a chance to mention and brag about his beautiful photography. I really thought of as mainly ornithological, because I see so many great pictures of birds that Tyler has taken and posts up on our corporate Slack. But really, he’s a nature photographer. So Jason Moore is reacting saying those photos are even better than I was pitching them. He said, “Awesome work, Tyler, thanks for the tip about getting down to the subject level.” For listeners who didn’t get to learn that, since we’re all photographers today with our smartphones, Tyler was coaching us whenever you’re taking a picture of nature to get right down there on the level of the creature, or seeing that you are taking a photograph of it makes it much more vivid and exciting to be right at the level of what your photographing.

Too many of us, well I’ll raise my hand anyway, too many of us tend to stand up and point down with our cameras at the things we’re taking pictures of, so that was a great photo tip from a real pro. “Jason close that tweet. The last great photo tip from Rule Breaker Investing was to make the subject off center of the shot and it improved my photos tremendously. Looking forward to giving this a go.” Well, thank you, Jason Moore. The last tweet, I’ll call up Alex Carignan @alexcarignan13. “I will never understand people’s hesitancy,’ Alex writes, ‘to invest during downturns. If anything, I’m most hesitant when the market, he writes, ‘is at all time highs? I think I owe a lot of this @DavidGFool and @RBIPodcasts.” Well, thank you very much. Alex, I can’t always describe myself as a big bottom fisher or a hero in dark times, I’ve often said I’m not trying to be a bear market hero because bear markets don’t happen that often. I’d much rather as Rule Breakers, we’re all bull market heroes because that’s when the real numbers run up.

But I will say this, maybe the most thematic phrase for this podcast in the year 2022 is, has been, maybe will continue to be, just keep swimming, and when you rock Dory’s phrase and yank it out of its original context from Finding Nemo, and you use it as an investor, it reminds us to do exactly what Alex is doing, which is to continue investing during the downturns. You’ll be amazed by the results years from now. Well, thank you for a wonderful month of tweets. We are again @RBIPodcast on Twitter. I’m @DavidGFool if you want to follow me on Twitter. But man, do I enjoy following the community of so many Fools and Rule Breakers that has assembled in and around this podcast on Twitter, so thank you each. Now for the tweets though, keep them coming. We always appreciate it @RBIPodcast, of course, our Twitter handle for this podcast, you can find them. Follow me on Twitter if you like, @DavidGFool. Rule Breaker Mailbag, Item number 1, this one is from Jeff Chrishell. Thank you, Jeff for this note. David’s based on a true story tip, that was from my Pet Peeves Volume 7 podcast earlier this month, immediately made me wonder if such a visualization is available for books.

Now I’m going to pause it there for a sec, and just mention that as I talked about movies that claim to be based on a true story, or inspired by a true story, or based on a true story in Jeff’s words. I referenced the website informationisbeautiful.net and it really is beautiful, the page I’m talking about. If you hadn’t already done this, you can just google the phrase, movie visualization based on a true story, and the top hit will take you to Information is Beautiful. You’ll find what looks to my eye, I took chemistry back in high school, but is it a spectrograph? A left to right strip of blue and red shades, and what you’re seeing on that page when it’s blue, is that time, that portion of the movie that is actually true. Looking at movies based on true stories, you can look across the full two hours of the movie as a strip of colors, and see when it’s red and it was not telling the truth, it was inventing or is outright false, or blue when it was recounting accurately the events of that story.

It’s a really beautiful visual, and I wanted to make sure before I continue this note that you my dear listener know what we’re talking about. We’ll now return into Jeff’s notes because he’s talking about that same visualization if it were available for books. He goes on, “My wife and I read the Little House books written by Laura Ingalls Wilder when we were kids. I took them to record historical events. My wife recently discovered Pioneer Girl, the annotated autobiography of Laura Ingalls Wilder, which gives commentary on how parts of The Little House saga are the true story, and others were fictionalized.” Jeff writes, “It was a surprise to me,” and I also thought he writes of Tim O’Brien’s book, The Things They Carried. Its stories of the Vietnam War are fiction yet very true. A line in the chapter, How to Tell a True War Story, that’s the name of the chapter, is almost a summary of the whole book quote, “A thing may happen and be a total lie. Another thing may not happen and be truer than the truth.” Jeff continues, “I get the same feeling reading the works of Ernest Hemingway or John Steinbeck. Their fiction rings very true to me.

Maybe as my Little House experience would indicate, I’m just too credulous. It will be interesting to run The Old Man and The Sea, or Of Mice and Men, or The Things They Carried through a pedantic historical reality filter to see how much came out true-ish or false-ish. Thanks, Jeff Chrishell.”

Well, Jeff, unfortunately, I couldn’t locate any online tool that breaks down a book purporting to tell a true story, which of course, novels don’t, but purported to tell a true story. It would be really cool to look across all of the pages of a book or maybe tint them blue or read on the Kindle app as you’re reading. Of course, many people don’t really care much about this. They just want a good story, whether it’s true or not, but for pedants like me anyway, I want to include you, maybe you too Jeff. For pedants, we have to resign ourselves to informationisbeautiful.net, where, don’t forget this, there’s a drawdown box listed as pedantry on that page, and you can actually choose the level of how pedantic you want it.

How true you insist that your movies be. We talked about this a little bit at the start of the month, but just to quote it again, “If you draw down the pedantry box to only the absolute truth, than even the truest of based on true story movies,” I’ll give two quick examples in a sec, “even those begin about 20% of the time to be inventing things, because even if you’re going to be this pedantic, even invented dialogue can’t necessarily be proven in some cases as being true.” Two of the truest, based on true story movies of the last decade were The Big Short and Selma. The Big Short, 2015, based on the book by Michael Lewis, of course, 78.5% absolutely true, according to informationisbeautiful.net, and Selma, The King, 81.4% of that movie is true. If you want to go down to the bottom of the rankings quickly, The Imitation Game, 17.6% of that is absolutely true. One in six scenes in that movie are actually true.

American Sniper not grading out too well either at 29.4%. Onto Rule Breaker Mailbag, Item No. 2. This one in particular for the sports fans out there. If you’re not a baseball fan or not that interested in, I don’t know, everybody likes movies, we just talked about them, boxing, then you could probably jump to the next one. But I really enjoyed this note from you, Vince Greenery. Thank you very much. “Yo David, it’s me Vince,” he starts. “Hopefully, you’re not so young that you don’t remember.” Vince writes that my salutations, “Yo David, it’s me Vince. Was inspired by a movie you mentioned in your Pet Peeves Volume 7 podcast this month, Rocky.” Rocky would call out to his girl. I know many of us can hear this in our heads. “Yo Adrian, it’s me, Rock.” Why do I mention this? Vince says, “Well, you suggested that the movie Rocky was not based on a true story and you are correct, as you were when you suggested Chariots of Fire was, “but, Vince continues, “Rocky was inspired by a true story and here is that story. In March 1975, down-on-his-luck, a fledgling actor named Sylvester Stallone scrape together some money and bought a ticket to the closed circuit broadcast of a heavyweight fight between World Champion Muhammad Ali and Chuck Wepner.

Wepner, a liquor salesman from Bayonne, New Jersey, nicknamed the Bayonne Bleeder, was ranked so low that the fight wasn’t even sanctioned as a championship bout. It was the first heavyweight bout held in Cleveland since 1931. Inexplicably, the journeymen boxer hung in for nearly all 15 rounds with Ali scoring a TKO, a technical knockout in the 15th. If you know the movie Rocky, you can easily see that it was clearly inspired by this fight, where the huge underdog nearly pulls off the big upset.” Well, Vince, thank you for that storytelling. I did not know that. I did remember Chuck Wepner. It makes a lot of sense to me what you’ve said, “So maybe it was inspired by a true story.” Before I close, let me also comment on your baseball Pet Peeve about the win being assigned to a pitcher. First, the starting pitcher is the driving force behind the teams chances of victory as all the betting odds are primarily set based on the starting pitcher. In your example, the poor guy who did his job for four innings gets no credit, while the guy who did a bad job gets the win because the team rallies, and more than offsets their new pitcher’s poor performance.

In this case,” Vince writes, “Circumstances dictated the outcome more than performance, but isn’t that what happens with runs batted in a halo triple grounds statistic and for baseball fans?” Yes, I agree, Vince. He continues, “If no one’s on base then the batter has to hit a home run to get an RBI. The batter who has more runners on base when it comes to the plate, something totally beyond his control, will fare better than the one who comes to the plate with fewer base runners. There are other examples of widely accepted statistics being misleading.” He writes, “Batting average is another, and I think those of us who follow the markets or many other fields,” I don’t know. I’m sure this is probably true in what? Meteorology? There are many examples of widely accepted statistics that are misleading.” I remember a past Pet Peeve dear listeners, when I talked about how the chance of rain on your weather app should never ever say 0%. Well, maybe almost never ever, but how many times in Washington DC or North Carolina, my two regular haunts, do I see it’s 0% and it’s raining as I look at my phone? It should always say, 1%.

Anyway, back to close that Vince’s note, your love for baseball’s obvious, it probably won’t surprise you that similarly situated baseball fans have devised a statistic to assign wins to every player on the field. The formulas are arcane, but there is a statistic called Wins Above Replacement WAR for short, that tries to calculate how many more wins each player contributes over the course of a season than a hypothetical player who has fringe major league abilities, you may be surprised that the WAR of an all-star caliber player is between 4 and 5 wins above replacement. Now, Vince, I didn’t know about WAR. I do admire and appreciate it. I haven’t even looked into the arcane formulas myself, but I appreciate the effort to think through the full valuable player. After all, if it’s a hitter, that person is also playing in the field more than half the time really. What he does for his team in the field should be counted and indeed wins above replacement Looks at a player’s sum total. You can compare hitters versus pitchers. I’m going to stop geeking out on baseball.

Season is almost over, by the way, this is an appropriate end Vince’s has now, by the way, as a ‘dians fan, he says, my inclusive invention to bring them together, those resisting the recent name change from Indians to Guardians, and those accepting the new names. He writes, as Indians fan, I send you condolences regarding your Twins’ uninspiring performance this season. Fool on. Vince Greenery. Great. Now Vince, yeah, the twins really did collapse. They had the lead most of the season. Anyway, thanks for the fun. Let’s move to Rule Breaker Mailbag Item No. 3. This one comes from Brett Wyman. Thank you, Brett. Hi, David. I wanted to ask a question about the penalty box in Motley Fool, Stock Advisor, and Rule Breakers. From what I’ve heard, the penalty box is a place where companies get placed when the team has concerns about its ability to beat the market and it temporarily shifts from a buy recommendation to a hold. As the Motley Fool shifts more and more to focus on ranking current recommendations. Brett writes, “I would like to know more about why there aren’t more companies given a hold status”.

He goes on with both Stock Advisor and Rule Breakers having hundreds of active buyer recommendations. I think it’s safe to assume that the team has collectively have higher connections in some companies than others. Often on Motley Fool Live and again, many of you will know Motley Fool Live, but I’ll break in here for a sec dimension. I think of Motley Fool Live as the TV channel attached to fool.com, our website. It’s the TV channel for our members and it runs, well, not every hour of the day like cable TV with its 9,000, shares does. But during weekdays anyway, it’s pretty dependable from somewhere around 09:00 to somewhere around 5:00. We have a bunch of Motley Fool Live fans and if you’re a member, you should join us on Live.

If you’re not a member, Dan, you should become a member. You can join us on Motley Fool Live anyway, Brett clearly is because he says often on Motley Fool Live or an articles from the team updating us on how companies doing analysts will make it very clear that a company is going through a hard period. I understand why we wouldn’t want to sell that company just because it’s in a challenging periods since all companies go through tough times. But wouldn’t it make sense to shift that company to a hold until it starts performing again. I’m going to pause this for a sec because I have two all-star Rule Breakers joining me. I’m going to keep reading a little bit more of Brett’s note, but first let me welcome in. Tim Beyers and Rick Munarriz. Tim and Rick, welcome back to Rule Breaker Investing.

Tim Beyers: Thank you, David.

Rick Munarriz: Thanks for having us, David.

David Gardner: You bet, you’ve heard the first part of this and you probably already have an answer to or something to share, but let me just go a little bit further, and then we’ll open it up, guys. Brett goes on, for me, it gets a bit confusing when the teams are saying this company is an active buyer recommendation, while also acknowledging that the business is facing hardship and the thesis maybe in question, why to keep so many active buy recommendations rather than shifting older recommendations with lower conviction to a hold status? I’ll just skip to the end here he says, “Any insights you could give on how the penalty box relates to rankings and active by recommendations would be really helpful”. Well, Tim and Rick, I think part of the purpose of this podcast is to help, especially for Motley Fool members or people thinking about joining Stock Advisor or Rule Breakers. I have two of my great Rule Breaker friends here, Tim and Rick. Tim, let me turn to you first. What’s the first thing that comes to your mind as I read Brett’s note?

Tim Beyers: It’s a great question and I love the question and we often see Brett on Fool Live. It’s great a question coming from a great Fool. I’m going to key in on the last thing he said, which was any insights you can give on how the penalty box relates to rankings and to act buy recommendations will be really helpful. Let’s start with how to think about the penalty box. You should think about it as a hold. You should think about it in terms of stocks that we think could underperform the market in the short-term because there are questions. But really, I think of the penalty box. I think one of the things that Brett mentioned that the penalty box may not be and maybe I hope this is clarifying, Brett. We don’t necessarily put a company in the penalty box if we think the thesis has changed. If we think the thesis has changed, it’s much more likely, we would say, should we sell that company. However, if a company is in the penalty box, we do have questions that are at the moment unanswered because they’re unanswered, we think the odds of that stock lagging the market are higher.

Therefore, we’re keeping it on the sidelines for the moment. But I think David, we want to maybe differentiate between thesis change and we’ve got questions. We’ve got questions is potential penalty box. Thesis change. Maybe we should sell this because this isn’t the Rule Breaker we thought it is. Then everything else that’s a buy recommendation is we still think this is a breaker. Even if it’s going through hard times, we still think it’s a breaker. One of the defining things about Rule Breakers is that, David, I think you could speak to this they often go through hard times that it is a roller coaster ride and in some ways, the fact that they are going through hard times sometimes that’s a good indicator. Let me give you just one very short example of what I mean. There’s a current company on the Rule Breakers scorecard that has gone through a little bit of a hard time that I think proves the rule, that it is a Rule Breaker and that would be Snowflake, where Snowflake intentionally compressed its margins because it knew it had a problem in that it needs to be able to because it has a lot of its business is based on usage. The thing you want to do is increase more usage. They deliberately screw things up a little bit for themselves, for the benefit of customers, to make it more attractive economically, to use their platform.

David Gardner: That’s a good example, by the way, ticker symbol SNOW. Tim, how did you and the team react? Rick, I’m going to kick it to you right after that asking maybe for another example or two because I think examples are so illustrative for listeners.

Tim Beyers: For us, the way we reacted is, wow, I mean, they drove themselves into a ditch, but for all of the right reasons and so you may see now that on the most recent rankings, bringing rankings into this answer, Brett, Snowflake happens to be No. 10 on the list of the highest-conviction current stocks on the Rule Breakers scorecard. We think it’s doing the right things for the long-term, even though in the short-term drove itself into the ditch, David.

David Gardner: Yeah. Well, that’s really the opposite of the penalty box and a lot of ways guys, because the penalty box is there for, as you said, when we have real questions and real maybe misgivings if we have bad answers to those questions as we ask the questions. Snowflake is a great example of a company that has hit a hard time. I mean, the whole market has been hard for Rule Breakers for the last year or so. But the opposite of what we might expect that actually interests the team and Rick our new company rankings have Snowflake high. Rick, maybe speak to the rankings a little bit, and then do you have another example or two in mind here?

Rick Munarriz: Yeah, sure. The great thing about rankings, and especially with the fact that we’re not putting rankings are our current thoughts so you are getting our best ideas. We don’t have the bottom 10 rankings because we don’t think that’s useful. I think a lot of times when you’re talking about these hold, even though they’re helpful, obviously, the penalty box is helpful, you don’t want to be in a car where someone’s tapping on the break all the time because you really wind up going nowhere. I think that gets to the issue of what happens here. I think Brett had mentioned Netflix in the email. Obviously, you didn’t have to read it because I was just an example that Brett gave. Netflix while not a Rule Breaker stock as a Stock Advisor stock. This is a stock that I know fairly well because next month it’ll be 20 years. My first 20 years as a Netflix shareholder will be, I’m not going to say 20 years. I’ve been a Netflix shareholder for a long time and I feel the pain. I see the stock.

I know it’s well shy of where it was just a year ago but I think in the case of Netflix, it’s not that the thesis was broken or defied anything, it missed guidance. It took a step back. Once every year Netflix actually fall short of its own guidance because it gives us very conservative guidance. This very guidance that it’s not conservative is this very real guidance that it sees at the moment. It’s going to be wrong sometimes. It’s not trying to be underestimated, so it can be that easily. In this case with Netflix, you have a case where if we were to basically not that Rule Breakers has Netflix’s stock, but put it in the penalty box if it was one of our picks and we putting it in every time that it would miss, which would be about once a year or every time that it’s subscriber numbers didn’t go the right way, even though revenue growing, cash flow is growing, you get to this red light, green light situation, which is a lot like Squid Game, just to tie it all back to Netflix where it becomes this gory body count. I do think that it’s dangerous to just lean on that hold as in, like, I’m not so sure about this because we are, I think, while we have many stocks on the Rule Breaker scorecard. I think all three of us are confident in the stocks when the initial recommendations were made and we think that the companies are evolving and every company goes through growing pains.

Tim Beyers: Just adding to that super quickly, Netflix is the stock that could have gone into the penalty box because there are questions, but this is a good example of getting to Brett’s point about do we think that things have changed so materially at Netflix that we would sell it? Answer no. Are there questions? Yes, but are they serious enough to keep us from actively recommending it? No. There’s always this mosaic of questions. I think as an investor, it’s a good thing to always be asking questions.

Rick Munarriz: Not to make doesn’t even longer segment David, but as a fan design of Netflix, one thing that I think would make me personally as an investor, personally maybe consider putting Netflix in the penalty box is obviously the rolling out this ad-supported ticker right now, which is exciting in some ways because they’re going to be able to reach a wider audience, like when Tesla rolled out that Tesla 3 in the Tesla Y reach a wider audience by a cheaper plan. But have also, and you see people just basically leave the premium plan an awful lot to the cheaper plan. That would concern me as a Netflix shareholder because I would think that that would have been a terrible move in retrospect. I’m not completely Pollyanna about Netflix, but it would take something like that dramatic just audience shifting away from a premium product to a cheaper option for me to say, well, I don’t know, maybe I’m not so sure about Netflix.

David Gardner: Well, those are two good examples, Snowflake and Netflix. Well, I think I was the one who invented the penalty box and I’m not even that big a hockey fan, but guys, it just felt like a good metaphor for me; the idea of taking an active skater off the ice, giving it a two-minute penalty for high sticking or holding and not putting that stock at that moment out for members. I do want to emphasize for Brett and everyone listening. If you’re a Rule Breaker of any meaningful duration then you probably already know this as a service client of ours, you should know that we’re really focused on the top of those rankings and what the companies are that you and I think we should be buying next.

Not so much as Rick spoke to this earlier, we’re not enumerating the bottom of the rankings and carefully picking among which is the very worst stock versus the second worst stock in the service. That wouldn’t be a great use of our analyst’s time. It’s really not what our members want. Our members would like to know what is the next thing to buy, whether gentlemen, it is a new pick or an existing pick from the wonderful universe that we get to draw from. Brett, I hope that makes sense and everybody listening that we’re really focused on the top of the rankings. That’s brief thoughts for me, but as we exit this point, let me kick it back to Rick and then Tim for just a final thought, Rick.

Rick Munarriz: Just like you mentioned with the hockey reference and again, I’m not a hockey guy either, but I know that when a team is losing, you don’t put the whole team in a penalty box because hey, sometimes the puck isn’t just going your way, which is like this market feels. You put the person that did the infraction, the one that needs to cool down off the ice, so to speak. It is the thing where it’s easy to get emotional about these things when things are not going your way and you’re seeing so many stocks drop and why aren’t there more in the penalty box? But by design, I think just the fact that we have a handful of stocks in the penalty box, I would be frightened if we had too many stocks in the penalty box, as Tim said, that point to sell.

Tim Beyers: I would just add to that, stretching the sports ball analogy by crossing sports and going into World Soccer. The way maybe to think about rankings is a little bit like you’re starting 11 that you might put out on the pitch. Particularly if you have money to invest and if you’re new to Rule Breakers, a great place to start, I would say first is what we call the starter stocks. There’s an About page on the service and you can see all the things that we’ve laid out how to get started. One of the ways is to get started with our starter stocks. Another way is to look at the rankings and if you don’t have any exposure to any of those stocks, getting a little bit just to get yourself in the habit. David, I think I’ve learned this from you more than anybody else getting in the habit of putting a little bit of money to work. Even if it’s a really a little like 10-20, 50 bucks into a stock and developing a little bit of the habit, and we put together a tool for you in rankings to help you get into the habit.

We’ll make you a better investor because you’ll have developed that habit, you’ll be buying companies and then you’ll be following those companies and then you’ll be learning how to evaluate those companies. That’s a really great thing to do. The penalty box is a way for us to say, hang on a sec, if you’ve got some money to put to work, maybe don’t put them into these companies yet. But we’ve got these rankings over here and if you’ve got money to put to work, these ones, not bad. One last thing, a mechanism that we use those rankings for. Sometimes it allows us to revisit a great company that we just haven’t talked about very much in a while and a good one that David, nobody is more familiar with this company than you that we just addressed in the last round of rankings is Intuitive Surgical. Just hadn’t talked about it in a while and the company just keeps getting better. Does it belong in the top 10? You bet it does.

David Gardner: Well said Tim, well said Rick, thank you guys so much for joining and Brett Wyman and everyone listening, hope that was helpful, foolish best. Onto Rule Breaker Mailbag, item no. 4, this one from Charles Fick. Thank you, Charles. Dear David, thank you. I cannot express the thrill of hearing my note read on the podcast on July 27th, that must have been our July mailbag of this year. Thank you, Charles, my wife and kids were all asleep upstairs as I listened so I was pumping my fists and cheering all around my living room silently and alone, which was both fun, Charles writes, and funny and a bit awkward. I truly I’m a capital F Fool anyways, I wanted to write again to say thanks and let you know that I continue to enjoy the podcast each week. It’s so interesting to have heard the prior eight years of mostly successful five-stock samplers juxtaposed with what has happened to the market since 2020. What a wild ride it has been. Ironically, one of my best performers right now in my portfolio is Bluebird Bio ticker symbol BLUE. I bought it because you were recommending it on a previous five-stock sampler, April 2019 I think, and when I checked the current price, it had fallen so far.

I’m going to pause for a sec there. I’m not looking at the actual numbers, but Charles, you’re absolutely right. Bluebird bio, not a very good stock pick of ours in Motley Fool Rule Breakers for the most part and when I timed it up, if it was right, April 2019 or thereabouts. Man, it was about to lose something like 90% of its value. Let’s pick up Charles’ note right there. “I figured,” he writes “this guy is a pro. He thought it was a good buy at that much higher price, so it’s a much safer bet here at 10. Then I bought it five more times as it kept falling, making my average cost basis $6.19 a share. Now it is a small winner, a rare winner for me.” Well, before I go on to Charles’ question, let me just say, I don’t endorse taking this approach most of the time on Rule Breakers, we’re talking about adding to our winners. It is very true that it’s been hard to find winners over the last 12-18 months.

As long as you’re not throwing too much good money after bad, as we say, I guess I’m OK with bottom-fishing, the Rule Breakers scorecard, but those are treacherous waters as well to bottom-fish so proceed at your own risk.

Now onto Charles’ question and it’s a very good one. He said I did have one question for you. I’m interested in switching careers and getting into financial services/investing. What do you recommend is a good first step? Well, my first recommendation is not to listen to me because I didn’t really do that. I’m a stock picker but I didn’t get any formal training. I didn’t have to have a certification to start an online site that was on AOL back in 1994, but these days, I’m surrounded by financial professionals, many of them working for our sister company, Motley Fool Wealth Management. Back for a return appearance on this podcast, the ever delightful Megan Brinsfield and Megan, great to have you back. Our Director of Financial Planning at Motley Fool Wealth Management, a sister company to The Motley Fool LLC. Megan, how are you doing?

Megan Brinsfield: I’m Great. Thanks so much for having me back.

David Gardner: A delight. As Charles’ question asks, I’ll ask you, let’s just start it right there Megan. What do you recommend is a good first step for someone who wants to work in, this is a big phrase, financial services/investing?

Megan Brinsfield: I think that that is such a broad field or characterization of a field. I developed a little decision tree that we might go down. I do want to preface and say, I don’t consider myself a career switcher, but I would say I’m a career pivoter because I started in the world of public accounting and pivoted to be a financial planner. It wasn’t totally out of the blue, but it is something that required different certifications and different experience. That’s definitely something that you would want to consider if you are perhaps more established in your career and thinking about a change.

David Gardner: Just for the fun of it, and Megan share as much as you’d like. How many years were you in accounting? At approximately what age did you make a switch? For how long have you now been in financial planning?

Megan Brinsfield: I was in a purely accounting role for five years and then a hybrid role for three years. That hybrid role was where I really got to make that little switch step.

David Gardner: Did you have a strong sense at the start of that three years that this is what you’d end up wanting to do? Was there a catalytic moment for you?

Megan Brinsfield: I will tell you, I have a good friend who is also an employee of The Motley Fool, and she sent me the content from Rule Your Retirement and Robert Brokamp’s work. I said if there’s ever an opportunity for me to take on that position, it would really be a dream role. It was definitely a dream come true to work at The Motley Fool organization as a whole.

David Gardner: Well, and you’ve added so much value as you continue to work with members and often people who have big questions. Financial planning is something that runs deep, especially the older that we get and you start thinking about legacy planning in some cases or maybe I’m I showing my age at 56? Anyway enough about that. Megan, what’s the first decision tree question we should confront for Charles?

Megan Brinsfield: I think one that requires a little bit of introspection and assessment of your personal strengths really do you want to be someone that’s working with clients a lot and interfacing with people, or do you want to be more on the back-end doing processing and analytics type work? At Motley Fool Wealth Management as an example, we have our financial planners that are talking to clients every day. Then we also have our portfolio management team that is selecting the stocks that are placed in client portfolios. They’re really doing a lot more analytical work and working with each other as a team more so than working directly with clients.

David Gardner: I’ll just play the role of Charles. I don’t know Charles beyond his lovely mailbag entry, but I’m just going to say he says client-facing.

Megan Brinsfield: Right. I endorse that path. Once you decide you want to go down that client-facing path, a lot of organizations will split that role into a sales role and a service role. In the sales role, you’d be talking to new prospects every day and sharing your excitement around investing or a particular solution with them in the hopes of making them a client or working with them longer-term. Then in the service role, you might be responsible for a group of people who are already clients and you’re really their point of contact, that steady voice that’s going to keep them on a plan over time and implement changes with them, account for different twists and turns in their lives. Each is a very valuable skill but it’s really an assessment again, of where your personal value and joy is derived from.

David Gardner: Is there one more decision tree question to ask?

Megan Brinsfield: There is, and it is really what clientele you have a passion for serving. This can determine the types of certifications that you might need to get. Let’s say you want to work with young professionals who are just starting out. Well, a lot of that financial advice is tailored to things like budgeting, debt reduction, savings plans, and really getting your financial footing. Whereas if you would prefer to work with clientele that maybe have multi-generational wealth. You’re targeting Bezos as a client of yours. That’s going to be a very different set of issues to tackle and might require just some different knowledge level.

David Gardner: Well, I’m having so much fun. I’m going to stop being Charles and I’m just going to say, let’s go down the other side of the decision tree because it’s so interesting and thank you so much for organizing it this way. Portfolio management on the back end, what’s the next decision tree question for somebody who’s headed toward portfolio management?

Megan Brinsfield: Portfolio management in and of itself is an outcome of the decision tree in that you are responsible for someone else’s money. That’s a heavy burden. Not a lot of people can really take on that responsibility and not be wrecked with the overwhelming decisions of did I do the right thing? Knowing that a lot of people’s financial well-being is on the line. That is a heavy responsibility. It might be better to start out in a role where you are an analyst on a team and you’re contributing your ideas, you’re getting feedback on those ideas. Maybe you become familiar with some financial modeling before stepping up into a larger role where you’re making decisions on a lot of assets at one time.

David Gardner: Well, and that’s something that I can speak to because that’s what I have done. I’m not in charge of anybody else’s money. We do have those people that at The Motley Fool and forget about the Motley Fool we had. Though the world is full of many people, sometimes computers, in fact, increasingly, lots and lots of algorithms probably making decisions around asset management. But specifically for analysts, I think a really important attribute you should be able to exhibit is intellectual curiosity. I think the best people who think about what is the next stock to pick our fascinated by off in the future or what has worked in the past. Of course, we all have our eyes on the present because that’s what we’re all living through moment to moment.

But I do think that intellectual curiosity burns bright among most of the best stock-pickers at The Motley Fool. I’d also say something else to consider Charles and everyone else listening is, are you somebody who goes against the grain? I call them Rule Breakers. I’ve tried to be that and model that, and there’s no one way to do that. But I think sometimes you get an edge if you are zigging when the rest of the world seems to be zagging. Considerations for an investment analysts type. Megan did we get all the way to the bottom of the Pachinko table here? Or is there one more decision tree questions for this side of the game?

Megan Brinsfield: Well, I think that your insights were really valuable because I just have less experience with that more analytical, non-client facing side. I would say we’ve reached the end of the of the Plinko table. But I leave the final call to you, David. 

David Gardner: Well, if we did do the Plinko right and I’m not sure I covered every one of the basis we may have given short trip to one of those six. I’m not sure. Megan, you brought it. Thank you very much. For those who can picture Plinko or pachinko, that the balls dropping down and it’s bouncing left, bouncing right, hitting pegs depending on how you answer and what sort of interests are person you are. But at the bottom, there’s always a little window that the ball will disappear and there’s at least six different ones. Charles and everyone else listening, Megan has guided us through a pretty good thought exercise in terms of, you want to come to financial services and investing. But what exactly do you want to do? Megan, before I let you go, it occurs to me there might be a different answer. If somebody is 22 years old and just graduating college, let’s say and wondering, about this big field or what about the career switcher? Let’s make them older than when you switch your own career. Let’s say they’re around 49 years old today. Is there a different approach between those two people at those different stages of life?

Megan Brinsfield: I do think it’s worth appreciating the expertise that someone develops in a primary career before switching to another and recognizing that there are so many skills that can transfer from one roll to another. Maybe you worked in banking, our customer service or something like that. But you really enjoyed the buzz of getting to talk to a lot of people. That helps you in this Plinko exercise that we pointed out. You’re already a step ahead. Whereas I think if you’re just starting your career, it really is an opportunity to do a broad exploration. And not just choose one path, but take an opportunity to talk to folks that have spent a while working in these different careers and finding what really clicks for you and not being afraid to experiment.

David Gardner: Megan Brinsfield, Director of Financial Planning and Motley Fool Wealth Management. Thank you once again for joining with us, sharing your wisdom and your insights. Always a delight to be with you Megan Fool on.

Megan Brinsfield: You as well. Thanks.

David Gardner: All right, and onto Rule Breaker Mailbag, Item No. 5, this one really could be 4B because in a lot of ways it flows naturally from the question just asked, but asked for a different purpose. I’m bringing on a different expert. It’s my pal, Jennifer Gennaro Oxley, the Executive Director of The Motley Fool Foundation. Jennifer great to have you back to the show.

Jennifer Gennaro Oxley: Awesome to be here, David.

David Gardner: Jason had this, he dropped me a note privately and since it connects so well with the previous note, I haven’t given his last name, so we’re just going with Jason. But here it is, Jennifer. He said, “I am passionate about financial freedom and hope to work for the Fool Foundation one day. If you were me, what skills would you focus on building to ensure you were the perfect fit?” Now, Jennifer, I will note because Jason is someone that I know. I know that he is more of a mid-career person, so I don’t know whether the advice would be different for, let’s say a 42 year old than let’s say a 22 year old. But Jennifer Oxley, how do you take that one?

Jennifer Gennaro Oxley: Well, first of all, I’m excited that Jason has a passion for financial freedom because you know what, it’s going to take a lot of us to change this for everyone that’s living paycheck-to-paycheck. Jason, thanks for all that excitement and we hope to meet you one day. But let me tell you whether you’re starting out as someone who’s new in your career or you are where you are today. There are many skills that are transferable between different types of industries, whether it’s corporate, social impact, non-profit, or otherwise because it takes a couple of things to be successful at a foundation specifically ours. No. 1 is passion for the work that really makes it all easier when it gets hard, you stay in it. Then you end up scaling things because you love the work so much.

The second is a culture match with the company or with the foundation, whatever that is. If you have a dream to be a fool well, we’d love for you to be a fool, but low that it really comes down to that culture match. Then in foundations there are six areas that you may be thinking about that have transferable skills. Those six areas are strategy, advocacy, finance, communications, fundraising, and the ever-important community work. Whether you’ve done any of those things in your career or you have volunteered for a non-profit in your life. All of those skills are transferable. Take the passion, the culture match, and the transferable skills you maybe well on your way.

David Gardner: Jennifer, before I let you go, what’s going on in the foundation this fall?

Jennifer Gennaro Oxley: You know one of my favorite questions every day is what’s new at the foundation. I’m glad you asked, recently as a board of trustees, we decided to double down on the Rule Breaker Financial Freedom Fellowship Program. What that means is that we will be growing that fellowship around the country and we will start to focus in local areas. One exciting addition is Kimberly Driggins, who is the founder of the Washington Housing Conservancy. I urge you all to check them out because I’ll say it again. Kimberly Driggins at the Washington Housing Conservancy. They have an unbelievably unique model in the Washington, D.C., area, where they are combining social impact dollar, private equity in housing to create more units that are available for everyone, everyone that’s living paycheck-to-paycheck, our nurses, our teachers. All of the people in the world that we know are doing amazing work every single day and they’re striving, but they’re not quite getting there. They’re not quite getting close enough to financial freedom. Kimberly has some answers for them and that’s why we brought her on as a fellow.

David Gardner: Wonderful Jennifer. Yeah, I’ve enjoyed getting to know Kimberly and starting to work with her through the foundation that emphasis she has on mixed communities. The brilliance of it is this is a sustainable model that can work in any city, but it’s not hiving off one group of people and saying this is just for them, whether it’s high rent, low rent, or anywhere in-between. It’s the same building with families of all different ages. Some of them are working in restaurants and some of them are probably taking the Metro to work at their local law firm. It’s a beautiful model. It’s a beautiful future, mixed community living.

Jennifer Gennaro Oxley: Can I build on that, David? She is also thinking strategically around the community itself and everything someone needs to be successful. The other reason we invested in her is that she’s thinking about those five drivers of financial freedom, housing, health, education, work, and money. If someone has a healthcare issue, if someone is dealing with an education piece, what she is doing is putting these units in communities that have the services that are necessary for someone to connect the dots and live a better life. That is one of the reasons we’re so excited about her as well. Mix communities connecting the five drivers and an interesting investment model which is very cool for all of us to learn about. Again, Kimberly Driggins, Washington Housing Conservancy, our newest financial freedom Rule Breaker.

David Gardner: Well, thank you for that, Jennifer. So good to be with you again. I’m reminded to say, every listener of this podcast knows what about Rule Breakers. Rule Breaker Investing, investing takes many forms and so do Rule Breakers. For many years, the Motley Fool is helped you find the newest Rule Breaker for-profit company. We hunt them, we put them out to our members. We buy along with you every month. That’s exactly what the foundation is doing now. Focusing our Rule Breaker gays on the world of financial freedom and not-for-profits and asking, who’s breaking the rules. Of course, always in a good way who’s breaking the rules out there? Let’s back on my. I do want to return it a close dimension that for anybody Jason included who’d like to join in with the foundation, whether you’d like to work for us one day or connect with us in any way, foolfoundation.org is the website. Thank you again to Jennifer Gennaro Oxley, to Megan Brinsfield, to my Rule Breaker pals and to you for suffering Fools gladly once again, for this Rule Breaker Investing Mailbag, October is nearly upon us. Fool on.

Christopher Lewis

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