The MapleMoney Show » How to Spend Money Wisely » Insurance

How to Win at Insurance and More, with Joe Saul-Sehy

Presented by Wealthsimple

Welcome to The MapleMoney Show, the podcast that helps Canadians improve their finances to create lasting financial freedom. I’m your host, Tom Drake, the founder of MapleMoney, where I’ve been writing about all things related to personal finance since 2009.

Money can be complicated, even for the experts. It’s why my guest this week has a financial planner, even though he was a financial advisor himself for more than 15 years. He joins the show to share some outside-the-box money tips, including how to win at insurance, the value of timelining your goals, why focusing on risk tolerance is a problem, and why you, too, need a financial planner.

Joe Saul-Sehy is a co-host of the popular Stacking Benjamins podcast, and co-author of the book called Stacked: Your Super Serious Guide to Money Management. I sat down with Joe this week to chat about the various money topics he tackles in his new book, and an interesting connection to the Hardy Boys.

Early in our discussion, Joe makes his case against the DIY approach to managing your money. According to Joe, even the experts should get outside help when it comes to their financial goals, to avoid blind spots and emotional decision making.

We also talk about risk. Joe explains his problem with the way investors and their advisors approach risk tolerance, how ‘winning’ at insurance has more to do with risk management than anything, and why your emergency fund is the centrepiece of your risk management strategy.

Do you prefer to invest in socially responsible companies? If so, our sponsor Wealthsimple will help you build a portfolio that focuses on low carbon, cleantech, human rights, and the environment. To get started with Socially Responsible Investing, head over to Wealthsimple today!

Episode Summary

  • Joe explains why he wrote his new book
  • How to look for a financial advisor
  • The case against DIY financial planning
  • Why you should surround yourself with people smarter than you
  • The value of putting your goals on a timeline
  • The problem with focusing on risk tolerance
  • How you should look at insurance
  • Your emergency fund is the core of your risk management strategy

Read transcript

Money can be complicated, even for the experts. That’s why our guest this week hires a financial planner, even though he was a financial adviser for more than 15 years. He joins the show to share some, outside-the-box, money tips, including how to win insurance, the value of timelining your goals by focusing on risk tolerance as a problem and why you, too, need a financial planner. Joe Saul-Sehy is the co-host of the popular, Stacking Benjamin’s, podcast and co-author of the book called Stacked, Your Super Serious Guide to Money Management. I sat down with Joe this week to talk about the various money topics he tackles in his new book, An Interesting Connection to the Hardy Boys. 


Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. Do you prefer to invest in socially responsible companies? If so, our sponsor, Wealthsimple, will help you build a portfolio that focuses on low carbon, cleantech, human rights and the environment. To get started with socially responsible investing, head over to today. Now, let’s chat with Joe… 


Tom: Hi, Joe. Welcome to the Maple Money Show. 


Joe: I can’t believe I finally made it back. This is the height of my career. I’m announcing my retirement because I’m on Maple Money. And there’s nothing better, right? 


Tom: So your goal was to be a two-time guest on the Maple Money Show and then call it a career? 


Joe: That was it, yes. I made it the first time. I should have retired after the first time because my life went into this deep funk. But then you asked me back. And I had to write a book to do it, to get back. I was very thrilled I finally made it back and now I’m announcing my retirement. 


Tom: You might not want to retire quite yet because I know Miranda Marquit and Martin Dasko have this competition going. J.D. Roth might be there, too. I think they’ve been on three times each, so you might need one more before you want to retire. 


Joe: I know those names, Tom, and I can’t compete. And I don’t know if I have another book in me. Yeah, those are some heavy hitters.


Tom: Well, I’m glad you came back the second time. I wanted to have you on because of your book. We had Emily Guy Birken on, your coauthor with the book. She ran through some things and we had some fun. Despite it being a lighthearted topic, we managed to talk about the zombie apocalypse and the Holocaust. I don’t know how all that worked together but it was a great conversation. I wanted to have you on just to kind of round it out, finish off some of the other things because this book goes across the board. It’s not a very specific book. It kind of covers everything. Just to start us off, why did you decide to write this book and how did you bring Emily on? 


Joe: There was a book that I’d written that had taken me 10 years I finally got serious about finishing it. In meetings with my coach, I kept talking about my book but I didn’t do anything about it. Finally, I got serious about it and finished the book. I handed it to my alpha reader, my spouse, Cheryl. She handed it back to me maybe 15 minutes later and, in the nicest way possible said, “This sucks!” It didn’t suck that the tips were bad or that I didn’t know what I was talking about. It was that the tone doesn’t match the way that I like to teach, the way I like to talk about money. I think we need to have some heavy conversations, but I think the way we get there is by including more people and showing people that this can be easy and fun. That book was none of that. I knew the tone was wrong. I was in Portland, Oregon, at this wonderful bookstore called, Powell’s. Have you ever been to Powell’s? 


Tom: I’ve heard about it from J.D. Roth, actually. He loves it, but I’ve never seen it. 


Joe: And rightfully so, because it is a block long. It’s this mishmash of what had been a city block of different stores. They blew out the walls and took them (the buildings) over one at a time, I think because in some places, even though the roof is the same height and the floors are in the same place, in some places it’s two stories. In some places, it’s three. It’s almost like those M.C. Usher paintings where there are stairs upside down, going all over the place. That’s what Powell’s feels like, which is awesome because you get tons of inspiration from these places. I was wandering around the bookstore and ended up in the kids’ section, which you totally know is me. I saw the Hardy Boys detective manual and realized this book… I was in fourth grade and the Hardy Boys were pretty campy. They were these fun mystery stories for kids. Nancy Drew was the same way. But this wasn’t that. This was a book that, right away, said it was written with the help of a real-life FBI agent. The fourth grade me was all about that. I thought, “Oh man, I can know everything it takes to be a detective like the Hardy Boys are.” My brother and I carried this around. We dog-eared it. My dad (who worked for General Motors) would leave for work, and on a muddy day we’d go out and look at the tire tracks. My mom would touch a door handle and we’d immediately go over with some tape to get her fingerprints. All of a sudden I just had this inspiration that, if I can make a book that is like the Hardy Boys detective manual (that adults would carry around) but it’s about money, that is the tone I’ve been looking for. Now, I had tone but I didn’t have format. So, we flew home. We live in Detroit. And when we opened up the door, my mom was there. She had finally decided to trust me with the stuff that’s been in the attic that was mine, and that Joey had back when he was a kid. My little league pictures, the fifth place father/son bowling trophy. And there was the Cub Scout Wolf guide in there. The cool thing about scouts is that way before all these apps that you and I talk about that gamified things, making it easier, take some of the… You know, we get all bottled up in our head about how difficult this is. They give you much more of a playful growth mentality, where you think, “Hey, if I screw up, it’s almost like a video game, I’ll just try again,” which is a great attitude to have about money. I’m just going to keep trying stuff. I love that. I love the gamification. The way they did it was very interesting. The Cub Scout Wolf guide is not chapters, they’re achievements. You get badges. Badges at the beginning of Wolf are pretty easy. The ones at the back are much more specialized. So every “chapter”  achievement was things you were going to need. Then very succinctly, they tell you how to do it. Then there are three or four checkboxes, the things you have to do to show proficiency because it’s not about what you know, it’s about what you do. Then there’s a place for your mom to sign at the end so you can get your achiever badge. For people that haven’t seen Stacked, that’s the way Stacked is laid out. It’s very simple and foundational at the beginning, but in each chapter you have an achievement badge. And there are things you’re going to need which may be campy (but you might not need those things). But we do layout in a humorous style. We know what we’re talking about. We show you how to get where you’re going and have some serious checkboxes of things to do. So that’s where the idea for the book came from. But I thought, who’s going to buy this? I want to do this weird thing that sounds fun to me, but who else is it going to be fun for? I was reading another book by this woman and in the back, in the epilogue, she was talking about how she wrote it, which authors often don’t do. She said she’d had this book deal for two years and had done nothing. And that is totally me. I will do the stuff I’m doing now, and I’ll never do this big project that I say is important, but that really isn’t something that I do every day. If it feels hard, I won’t do it. Writing a book felt very hard, and I totally saw myself in the future saying, “This is me. This is totally me.” She was working at Vice, which is a huge online publication for people who don’t know, when she realized she was surrounded by all these great writers, surrounded by all these fantastic people. Our Stacking Benjamin’s podcast is published three times a week and on two of those shows I interview writers. I interview some amazing writers. Then I realized I work better with a partner. I’ve never written a book before, so I don’t know what I’m doing. Somebody is going to keep me on task. I know a lot of great people I could partner with, but my first choice was Emily Guy Birken because she’s got a great sense of humour, much like mine. In fact, a lot of the jokes in the book that people think are mine are really Emily’s. I asked if I could call her. We got on this Zoom call and I tried to sell her. By the way, later on, we did the same thing with an agent. And we did the same thing when the book went up for auction with different publishers to see who would publish it. Each of these Zoom calls, Tom, went like this, “What I want to do is take the Hardy Boys detective manual, combine it with the Cub Scout Wolf guide, but I want to make it about money, for adults. What do you think?” I was so pleased that neither Emily, nor the agent we wanted, nor the top publisher in the U.S. said no. They said, “Yeah, that sounds cool. Let’s do it.” I was sure they were going to just hang up but nobody did. This actually goes along with a lot of lessons we have in the chapter about finding advisors. Surround yourself with smart people that have been there before. People talk about having certified financial planners that have a background, they’re fiduciary and have your best interests at heart. But even before that, surround yourself of people that are smarter than you that have walked that walk before, that you trust and appreciate, that you can have open conversations with. People that will question you like do. There were times when Emily said, “No, we’ve got to cut that.” And I say, “What? That’s the best stuff we’ve written,” and she still says, “No, no, no. Here’s the reason why…” She would challenge me. I feel like we often surround ourselves with people that don’t challenge us. Think about who’s really valuable. Somebody that tells you you’re right all the time or somebody that has the guts to show you when you’re wrong? We kind of dive into that late in the book, on advisors. But Emily has been a great friend, holding my hand and helping us get this done. 


Tom: Yeah. I said this to Emily on our episode, it’s a different kind of book. One I had read early on was, The Wealthy Barber. It’s more novel style. But where I see the two books similar is that they’re both easy reading. If someone’s noodle this, it makes it a lot more interesting because there’s a lot of really knowledgeable, helpful books, but they’re kind of dry. It’s the topic we’re in. But so I see those two very similar in that. It just makes it a little easier to handle what can kind of be a tough topic. And also that they both kind of handle this “beginning to end” part of personal finance instead of just about investing, insurance or something. It’s like we’re going to touch on all the things and make it fun. That worked a lot for me early on. 


Joe: But yeah, and thank you for that comparison, because that was an early inspiration for me when I was getting involved in finance. That was my favourite finance book. That book just hit me so I’ll take that comparison all day long, dude. That is great. Thank you. 


Tom: You mentioned the similarity of financial advisors. How would you go about finding a financial adviser? For me, I’ve never used one. I just do the DIY thing. But I totally agree that there’s room for some advice. Like you said, no matter how much you think you know about something, it’s nice to be able to bounce something off. An adviser can be a good case for that. Personally, if I were to use one or if I were to recommend one, I always give the easy answer of fee-only. At least that kind of covers off any concerns about bias and such. You’re just paying for the advice, and that’s it. Is it more complicated than that? How would you suggest someone find an adviser? 


Joe: Yeah, great question. I actually broadened it out even more, even less complicated. While I think that everything you said is correct, I think people really begin to narrow their focus on what “advisor” means. When I talk advisors, I think much more broadly. I’d like to do that if that’s all right? 


Tom: Yeah.


Joe: The frustration that I have ever since, because, you know, I’m in this unique place where I was a financial planner for 16 years, then moved over the financial media for the last, 12, 13 years. I’ve seen both sides. And both sides frustrate the hell out of me. Advisors have conversations that are tone-deaf between each other, and consumers have inane conversations that drive me nuts, which don’t make sense—both of them do. I try to find the middle a lot. But the thing that drives me crazy about forums online are when people jump into a financial forum saying, “Hey, my advisor recommended X strategy or X thing and I’m wondering what you all think?” I’m going to start there because if you’ve ever done that, the first thing you need to do is fire your advisor, period. And the reason isn’t whether it’s good advice or bad because, if you are asking a group of strangers whether the person who supposedly has your back is doing the thing that’s in your best interest, you don’t trust them and they have to go. They have to go. My first thing is not about fee-only or CFP or what their credentials are even though it’s hugely important stuff. My thing is much more the assumption that we have online a lot, this question that’s not true. It’s not even the right question. The question, people say is, “You don’t need an advisor because you’re smart enough to do this yourself?” Of course, you are. Yes, you are smart enough. But that is not the question. I was in financial planning for 16 years and I have a financial planner. Why? I have a financial planner because I have blind spots, I get emotional, and because of the fact that there is new things coming out and I can’t know everything about everything. So, to have somebody who can also call out my B.S because I’m full of B.S. (on different topics) and get hardheaded, to have somebody who will say, “No, Joe, I don’t think that’s right,” is fantastic. We spend so much time wanting to be right all the time instead of really asking, where am I wrong? I love that question. I walk into any room and I want to be surrounded by people that are smarter than me on that topic. By the way, that’s not just for them. It’s for fitness, for diet. I want to question, “What can I do better? How can I do this better? What can I do?” I’ll give you an example of what I’m talking about. Mary Barra at General Motors has done a great job, in my opinion. General Motors, by the way, is not the hot topic. People might be surprised I’m bringing up GM, but I’m a guy who grew up in Detroit. And to watch this rust-belt company that was doing things so backwards when I was a kid, continue to stay relevant and continue to do these moves that keep them in the game… Their electric car platform is pretty cool. It doesn’t get much press, but they’re still in the ballgame. And Mary Barra, their CEO, is a big piece of that. Mary Barra is the CEO of GM just like you’re the CEO of your personal financial picture. Imagine Mary Barra with her vice presidents, (also known as) her advisors, right? She has people running all these departments that are smart people. Imagine her coming in and going, “Okay, you people do this car thing. Do it for six months to a year. Do whatever you’re going to do. And then I’m going to come back six months from now, and you just report to me about how we did about the car thing, and I’m going to go.” No. Mary goes to all the meetings. She’s still an expert about cars. She knows much more about cars than you and I. For us, that means we go to camp FI. We go to FINCON. We read the books. We listen to Maple Money. We do all the stuff so that we’re super knowledgeable and we know what’s going on, but what does Mary do next? She is somebody that runs the division so that she can focus on the big picture stuff. That’s what I think about advisers. So, if you’ve abdicated the throne and you’re no longer the CEO where you’re letting your advisors be the CEO, and you’re just kind of checking in once in a while, you need to fire those people or redefine the relationship. You need to surround yourself with people who are super smart, who have your back who aren’t emotional in no matter what it is that you’re trying to be good at. If you’re trying to be good at money, which kind of fuels everything else, I think you’d have those people. But really, then I leave the definition, the fee-only—that’s only tier for me. The first thing is just breaking through this ice that people have thinking they’re smart enough to do it themselves, which I hear all the time. And that is not the way to think about this. 


Tom: Even before that part, you mentioned the idea of surrounding yourself with people that make you better. One of my favorite quotes (that I’ll totally butcher) is you are the average of the five people you hang around with. I really like that because it applies to everything. It could be how you spend, how you invest. If you have a business, how that works. When you have that sort of motivation and advice where you can have these conversations, just like with an adviser, you can bounce things off people. Sometimes you’re not even looking for an answer. It’s just the fact you’re having conversations. That was just a recent episode, actually. You have these conversations and get these little nugget sometimes. Someone sees something different or knows something you didn’t even know you didn’t know. 


Joe: It’s fabulous. Here’s a funny analogy that I think fits exactly what you’re saying, Tom. I never wanted to run a marathon. I had been a runner, but a marathon was always too far. 


Tom: I still don’t want to run a marathon. 


Joe: Yeah, 5K, 10k… I had no interest. We moved from Detroit to Texarkana, Texas. My wife likes to run, too, but like a lot of people, she doesn’t do it unless she’s with a crowd of people. So she found a bunch of people who run. She had fun with these people. They were nice people. Now, by the way, they’re all my best friends. They’re a supergroup of people. They love board games like I do. We hang out together. We’ve gone on trips together. But because I hang out with people who run marathons, I’ve run 11. I would have never done that if my pack hadn’t done that. You know what I mean? I think you’re right on. If you challenge yourself to be around people—I certainly wasn’t challenging myself to run marathons because that’s a hard thing to do. The only reason I did it was because of who I was surrounded by. 


Tom: I don’t want to suggest everybody just dump all their friends but if you’re hanging around people that are doing things and making you feel like you need to do things, (like keeping up with the Joneses), if you’re going out for happy hour when you don’t want to and spending money in different ways, it definitely goes the other way. If you’re hanging around with people that are (not purposely) sending you in a direction you don’t want to go—I don’t want to say ditch your friends, but it might be time to look for someone. 


Joe: Exactly! Somebody actually gave me a great way to think about this. Don’t think about getting rid of your friends. You’re right, because that is mercenary. It’s horrible. It’s bad. But here’s what happens. Be additive. Add to your friend mix, people that inspire you, that are a step ahead of you, that are doing the things that you hope to do in the future. What happens is, you naturally spend more time with them and there’s only 24 hours in the day. Instead of ending the relationship in this mercenary way, it just kind of falls by the wayside. It’s not that you’re trying to get rid of a friend. It’s the fact that because it doesn’t feed you and clearly you’re not feeding them either, right? It just goes bye-bye. I think that’s much better. Add new friends and don’t worry about getting rid of the old ones. 


Tom: That sounds much more evolutionary than what I was about to suggest. 


Joe: Tom’s like Joe. At the end of this, I’ve got to talk to you… (laughs). 


Tom: Exactly. We can’t hang out anymore, Joe. (Laughs). Another thing I want to talk to you about in your book is this idea of timelining your goals. I saw it in the book. You’re literally drawing lines and little pictures. For me, I’ve seen a lot of benefit from writing down your goals. Truly writing them down. I don’t know what psychological thing that is when you could have a digital to-do-list, but when you write it on a whiteboard or something, all of a sudden it’s more real. I’ve been a big fan of that, but you suggest something slightly different. 


Joe: I do. I take it a step further because that same brain, hand, a mechanism that locks it in when you write it on the whiteboard is the same thing that happens when you make it visual. When we’re babies, we don’t know the language. We don’t know any of that. We just have our eyes and we see things around us. That is incredibly powerful on just a human level, making things visual. Another thing I like about visualizing your goals is that the thing that we need to have—and this is another reason why we try to make the book light—we need to have some fairly heavy conversations that are difficult to get into. The best way to get into these is to kind of ease into it. The conversation I’m talking about is when you put your goals on a timeline. What you do is take just a piece of printer paper, landscape style. Put yourself on the far left as a stick figure. Draw a line across the bottom that represents the rest of your life and then at different ages, put these financial milestones you know are coming. I’ll give you some of mine. Let’s say it’s the year 2000. My kids are five years old then. I have twins. I know I’ve got two college educations I need to pay for. I also know when I want to be financially independent. So let’s say that age is at about 55 or 60, right? I put that on there. That still is thinking big. This isn’t that pretty FIRE movement when you say, “I’m going to retire at 27 and live in a tent.” I’m not a second house person. That’s not me, but I do want to travel. So I want to make sure that by such and such date, I have flexible enough stuff that I can travel a lot more. Just put whatever your goals are on this timeline. Then you begin to look at each goal individually, but you also look at them together because different than writing them down, now that it’s visual , you’re comparing them to each other. And this is where the values thing that seems really deep comes in. For example, you say, “If I can’t afford all of these, what do I do with them? Do I push back that retirement and make sure I pay for all my kids college? Is college worth doing? Does it actually make sense?” There is no right or wrong answer. But we start having these “what’s important to me” conversations when we put them on a timeline against each other. The other thing that we do is get rid of the freak out factor about saving, investing, and budgeting. I know people that are—I’m thinking of Tiffany the budgetnista who is awesome. When you hear the word budgetnista, it sounds military. It sounds like I’m going to be militant about my budget and Tiffany’s neither of those things, by the way. I didn’t want to imply that. However, you and I know people that are like that and they’re not fun people to be around. If you’ve got a budget for no reason, it’s nothing. But if putting my kids through college is going to cost X number of dollars a month and I don’t have it, now I get into value discussions about what am I doing today that I don’t really value that I could instead put in savings to get this thing that I say that I really want. Now my budget becomes much more exciting because it’s on par with the things I want. The other thing is, I’d draw this on a whiteboard for clients and I was a planner. I’d say, “Tom, this retirement goal you have, what rate of return do you need to get that goal?” And everybody would always go, “Well, I don’t know.” And I’d say, “Well, you know, to make sure we get it, we should probably figure that out. How did you determine your investments in your retirement plan?” And people would often say they had taken this risk tolerance quiz. Risk tolerance quizzes drive me nuts. The reason they drive me crazy is risk tolerance is a really important thing, but how ludicrous is it to say, “How much risk can I take before I ask the question, how much risk do I need to take to reach the goal.” I should probably know that equation first. Let’s say that it’s nine percent. Most planners will say focus on seven or eight, if possible. Let’s say to get your goal, you need nine. Now, two things happen. Number one is, we do that risk tolerance thing, but it’s a little bit different now. Now it’s real. Now it’s like, “Tom, can you learn to be okay with the volatility it’s going to take to do that?” That’s a yes or no. And if it’s a no, by the way, that’s cool. We either back up the goal, lower the goal or save more money toward it. We have other levers. The other thing is, when it comes to investments, we  get this question all the time. What’s the best investment? What should I do? Here’s what you do. You start off with that seven percent. And instead of looking at the whole world of investments, which we waste a lot of time exploring investment choices that don’t match our goal, we can focus on the ones historically that have done seven and only learn about those. Now I can get depth in my investments. The other thing too, that comes to mind right now as I’m saying this is, it also becomes okay say, “Okay, that sounds really cool but it doesn’t match my goal. It’s no longer about whether it’s a good option or a bad option, it just doesn’t fit. It sounds really good but it’s just not a fit for me,” which is so much better than trying to evaluate in this vacuum. I like timelining your goals because your goals fight it out among each other, and you end up with a budget that is much more aligned your goals. You end up with these goals that you’ve thought about, which one’s more important than the other one (if you can’t do everything). And if you can do them all, it also helps you think even more aggressively. I think a lot of the time we leave too much of our genius on the table. We don’t take it with us. I love timelining for that reason.  


Tom: I had a couple of thoughts from that. When you’re looking at things in a timeline, your risk can be different because your example of saving for college is a shorter timeline, so you need to play it safe with that compared to retirement, where you can take a greater risk because you know you’ve got more time to (historically) balance it out. One risk profile quiz doesn’t actually cover the difference between saving for your kid’s education and saving for retirement. Those can be a decade or more apart, so that makes a big difference right there. 


Joe: Well, and to your point, people often just look at the next thing. How many times have people told you they’re going to start their emergency fund once they get the debt paid off? And then once they get the emergency fund in place and the debt’s paid off, then they start investing. There is this cool thing I just learned. You take a piece of paper—and you can only fold a piece paper seven times. I found that out literally last night. I never knew that. But I did know this analogy for a long time. If you take a piece of paper and fold it, which is the doubling that your money gets with compounding interest. Compounding interest is so important and we don’t understand it. But if you can fold that piece of paper only 50 times, theoretically, do you know far the paper stretches, if you can do that? To the sun! Think about how thin a piece of paper is. Fold it 30 times and it goes to the moon. That’s the power of compounding interest. The sad thing is, when we only look at that next goal and we’re not focused on those long ones that you’re talking about, we give up some of those doublings that we totally need. 


Tom: Yeah, I do like looking at them separately like that. I think that timeline format would work better for that because you’re not just saying, “This is how I want to invest.” You’ve got this one timeline for this thing and this timeline for something else. Maybe you’re even saving for a vacation next year, and that’s going to be quite different. Seeing it that way helps. The other thing I wanted to bring up from the timeline idea was, Todd Tresidder, our friend, gave me an idea that’s more business wise, but it applies. If you picture where you want to be, whether that’s the income you’re making or some other end-goal it’s so much easier to work it back to fill in those blanks where you say, “What do I have to do today? What do I have to do a year from now?” Having that end goal and working it back, he believes strongly, that basically, almost makes it self-fulfilling. 


Joe: You know, it’s funny. I don’t know if this book affected you the same way, because when I read it, I didn’t think it affected me at all. I remember reading this book in the 90s when it came out. I thought it was, alright, okay. But now I quote it all the time. Seven Habits of Highly Effective People by Stephen Covey. One of those things Tressider is talking about is beginning with the end of mind, right? If you begin with the end in mind, everything just happens. I quote that, nonstop. It’s funny because it was only a few years ago that I read that book so I guess it really made an impact on me. I remember reading it thinking it was all just kind of basic. But it’s not. 


Tom: It totally makes sense to me. And I like this timeline idea. I’m going to try it. I’ll let you know how it goes. Just to take that list of goals and make it actually plotted out seems like an idea that makes sense to me. 


Joe: Here’s what I was thinking when we wrote that. Obviously, this is something I did as a planner. By the way, Emily wrote half the book and I wrote the other half. Then we edited each other’s and smoothed out the language so it was harder to tell who wrote what. We also put our own spin on things. But I was thinking of the beginning of Ramit Sethi’s book, I Will Teach You to Be Rich. He talks about not starting with your goals but starting with something that is “plus” that. I like the idea of goals. He starts with things like calling your creditors and or lowering your cell phone bill. But I thought if the true place to start is your goals, I truly have seen with a lot of families how timelining their goals has changed the game for them and made them get things that they couldn’t get when they were just writing them down. 


Tom: And having those goals in that end result is more motivating. Calling your creditor is more immediately impactful but you need that motivation to carry it through anyways. In your book, you cover this idea of how to win the insurance game. When I look at insurance, whether it’s life insurance, car insurance, I’ll get a couple of quotes. I’ll put some effort into it (but I don’t put a lot of effort into it). I haven’t gone too deep into insurance as a topic even on the blog, to really understand it and make the most of it. 


Joe: This is frankly my favourite chapter of the book. It’s an area that most people don’t like talking about but I think Emily and I did a good job in this chapter of making it not only palatable but super interesting that kind of changes your opinion about this. The way we do it—and frankly is the reason it’s so exciting is because I had my eyes opened about how this works. Most people ask the wrong questions. It’s almost like we talked about with advisers. We have these questions, Tom, that we ask ourselves—that the industry asks us. And you have to question the assumption, which is so often the case. The assumption the insurance industry puts in your head is, do you need this insurance? Do you need term life insurance versus whole life? Do you need whole life insurance? Do you need disability coverage? Do you need this car insurance? Can you save money on your car insurance? These are the things they ask. You don’t want to ask those at first. Instead, start off by broadening it out. The broader question and the powerful way to look at this is not to look at insurance at all. It’s to look at what I call, risk management. And I don’t just call it that. Financial planners call it that. When you think about risk management, you think, “No matter what I do, what is my risk going to be and how do I best cover that risk?” I’ll give you an analogy. When I was in Michigan as a planner, I had a client that worked for the highway department and would often build new roads. She told me, as an engineer, what they would do is make plans thinking about every single thing that could go wrong. Only once they then eliminated all these possibilities, would they begin construction. That’s what we want to think about. What are my biggest risks? How do I cover those? Now, let’s examine this. Instead of going, is this an important insurance? The big question is, is when I die, what needs to happen? What would happen? I started thinking about those dominoes and think, “Well, I’ve got my retirement plan. I’ve got my savings account. I’ve got this money in place. I have insurance through my employer. I have all these assets that I can use.” You’re probably going to buy less life insurance as time goes on, as you get older, as you accumulate assets, which is exactly the way to think about it. People also question interest rates which are very low on guaranteed savings plans. But inflation right now is through the flipping roof! People will tell me, especially now, that they’re losing money in this thing. Your ROI on that emergency fund is not the half a percent—or whatever bologna percentage point you’re making. Your return on investment is this; I can raise the deductible on my car insurance because I’m self-insuring these small accidents. I can raise the deductible on my homeowner’s and my renter’s insurance—the part I pay out of pocket. I can maybe have higher deductibles on my other insurances. I need less life insurance. Also, by the way, another insurance is, if I have six months of savings in a savings account, I can ride out volatility in the stock market. I’ve seen people that say, “Oh, I’ll just put it on a credit card.” The second the stock market starts collapsing, your inner brain goes, “Oh, what if I lose my job today and I need money? I’ve got to sell it for 20 or 30 percent,” or whatever the discount is. You don’t have to worry about that because you’ve got six months you can ride out, in the bank. The emergency fund is the centerpiece of your risk management strategy. And it’s the very first thing to do. At the risk of monologuing too much, I’m going to say one more thing. The way to think about insurance (and which ones are important as you’re examining the insurances that you have) is you need to flip it on its head. Insurance companies have these people that sit in the back room with thick glasses called actuaries. They know all the actuary jokes, by the way. So for those who think that I just offended people, they’ve already heard the jokes. I know some actuaries and they’re cool people. But their job is to know what the risk is to the insurance company. They set the price of the coverage based on the risk. You and I hear all the time ‘X’ insurance companies ripping us off. I’m not sure how it works in Canada, but I’m sure it’s very similar to the States, which is that these are regulated on a state level in the U.S. You can fool a state regulator, let’s say, maybe for six months, for a year. But this is a very competitive marketplace. There is no way an insurance company product is ripping you off. Now, that doesn’t mean that there isn’t an insurance agent who’s after a commission, who’s putting a square peg in a round hole. That happens. But the product itself, I don’t think, is a rip off. The problem is usage. If that’s the case, and the insurance is expensive, why is it expensive? It’s expensive because of the fact the actuary says a lot of people are cashing in on this thing. So that’s why term insurance is very cheap. Only three percent of term insurance policies are ever cashed in for the death benefit. Ninety seven percent of the time the insurance company wins. And by the way, if you think you’re going to have enough assets by the time you’re 65, it’s a cheap way for you to cover. It works for everybody. If you’re not going to have assets, then maybe a whole life insurance policy changes this argument. It changes this argument from what insurances do I have to what risk do I have? To figure out which risks are the biggest ones, look at the insurances that are most expensive and think about those topics. Don’t think about buying insurance—but think about those topics. And if the insurance is very cheap, you probably don’t need to think about that topic that much. One insurance policy I see a lot of people have because they get it through work is accidental death and dismemberment insurance if they have flexible benefits—accidental death and dismemberment pays you money if you lose a finger and heavy machinery. That’s what it’s made for. I used to meet (and still do meet) who have desk jobs. They’re on a computer all day in a cubicle typing away. Well, dude, if I lose half my index finger between the J and K key, it would have been an awful day—a bad day. Generally, what you can do is get rid of that accidental death and dismemberment coverage. And instead, get good disability coverage. By the way, disability coverage is expensive. But you know why? It’s because we get disabled far more often than we think we’re going to. 


Tom: A lot more often than you’re going to lose part of your finger in the keyboard. I like a couple of the things she said there because I raised my deductibles as well. On my auto insurance, I think the default offered was $500 and I put it up to $1,000 or $2,000, I can’t remember. But it’s the idea being that you’re insuring against these catastrophic issues. A little fender bender isn’t necessarily that, especially if you have an emergency fund that can cover the deductible. But if I were to get an accident that’s my fault and someone dies, that’s obviously a much bigger issue then than my bumper getting dinged. I like that because it’s like your timeline where you’re taking this issue, breaking it down into what you actually need to do and not getting lost in the details. You can do it better. 


Joe: Well, the cool thing is, two things happen. We get excited about this topic with both timelining and this. We get excited about this topic that people find dry because all of a sudden now I’m in charge. And it’s not about buying insurance because who wants to go talk to insurance companies? When I think about covering my risk, I get much more excited. And I also find, by the way, you save a lot of money on insurances when you think about it that way. In some cases, people pay more in the worst case scenario. When I was a financial planner, you’d paid the same amount, but you restructured your insurances because they actually met the plan better because you were thinking about risk management. You paid the same amount, but you had much better coverage because it was where the risk actually was. Can I give somebody a really tactical tip? I didn’t realize how effective it was until it actually happened to me, which is to take your phone and pretend you’re on MTV Cribs. Go around from room to room and just video your entire house. Open up drawers and look at stuff because I’m going to tell you what happened. You were at the podcast movement Chicago, weren’t you? 


Tom: No, I wasn’t at that one. 


Joe: I remember our mutual friend, Miranda, was there. And Eric was there. Anyway, I was in Chicago and my wife came for a nice weekend in Chicago with me after the conference was over. When she left, our house got broken into. And for some reason, my alarm didn’t go off. We had failed to set it—I have no idea how we did that, but we did. My neighbor was walking the dog and said, “Joe, I saw your door was open and I went to close it because we knew you were out of town and it had been busted open and a bunch of stuff was taken.” It’s amazing. Our insurance company was great. They made me fill out a form of the stuff that I owned and if I didn’t have that video, I would never know. Now, I’ll tell you where I screwed up because I still screwed up even though I had all kinds of video. I didn’t get serial numbers on the big stuff. I never knew this either, but local police work with pawnshops in the area. If somebody brings in a TV, the pawnshop person (before they accept it) is required to put the serial number in a database. I hadn’t done any of that. So while I got back the stuff, we weren’t able to catch the crooks. In some case, they kind of had to say, “Well, that model is gone now,” so we had to guess and they had to guess. So it’s a great tactical thing. It takes you 20 minutes. Go videotape your house. 


Tom: I’ve heard this before and I have yet to do it, so nobody broke into my house yet. But afterwards, fine. 


Joe: If you’re going to do it, do it quick before Tom actually does it. 


Tom: Yeah, I do need to go ahead and do that. One of the things is, I kept putting off because I was thinking, “No, I’m going to take pictures and make a real long list in a spreadsheet and really capture all this,” because I figured that would be better than a video. And I guess it would be, especially when it comes to serial numbers and such. So maybe I’ll go to that video pretty soon. 


Joe: It’s like mom says, don’t let perfect be the enemy of good, Tom. 


Tom: Yeah, exactly. It’s one of those things where, like you said, only takes 20 minutes. I could kind of open the drawers in advance and video record everything. I should do that for at least a minimal solution compared to trying to list everything out. 


Joe: Yeah, I would have never of known half the stuff that was in that video. I would have forgotten more than half. 


Tom: Oh yeah. If someone had asked me right now to list everything you own—and I’ve got a lot of junk, so to list all of it out would take a long time. Thanks for being on the show. I think this is a great book for a lot of people. Listeners of this show probably know a lot about money, but it’s still a fun read. They can also go out and help other by suggesting this book. It could be a subtle way for someone that’s not so great with their money. They’re not too into this. You could say, here’s a fun book, why not check it out? With your podcast, I’ve seen you post bad reviews before. I saw a two star review for the book that said, “I’d skip this one,” but that person is wrong, in my opinion. You should go out and get the book. 


Joe: Actually, it’s funny. I read our reviews because I take them very seriously. We’ve only had three bad reviews for the book that I know of. We’ve had bad reviews over 10 years of our podcast but it’s always the same stuff. And these people clearly are not my audience. My goal is to make this comfortable for somebody who isn’t familiar with money. Somebody who feels like it’s going to be a chore, who thinks it’s going to be difficult and for those people who just want more tips faster without any clowning around. The bad review I get is always, they clown around too much. If you read a bad review of my book (which there’s three of them) it’s generally that we clown around too much. Yeah, if you don’t like humor, you can’t buy our book. Don’t even get it from the library. Don’t, because we’re not for you. If you’re a money nerd and you like things funny, the last quarter ( like the Cub Scout Wolf guide) builds on itself. The last quarter of the book is hell and nerdy. I’ll put the last quarter of the book up against any personal finance book that dives deep. But that’s the last quarter. The first quarter is very foundational for people that are brand new. But it’s built like the Wolf Guide. It’s not meant to be devoured. It’s much more about picking the achievement you need today in a way; read the chapter, click off the boxes at the end and have your mom sign it to get that badge. Skip the badges where you think you’re doing well. 


Tom: That’s exactly it. The one that said there’s too much clowning around. It’s just not for that person. And that’s fine. 


Joe: Yes, you’re not going to change that. And by the way, if you’re thinking about reviews, the best way to get to a creator better is by actually writing to me. I will read the review, but I often think it’s more fun. I’ve had some great dialogue with people that have helped me change my show and writing that I’ve done when they write to me. When you leave me review, we can’t have a dialogue. And maybe you don’t want a dialogue. If you do, and you want to talk about creating a show, Tom, I’m always up for that. Like you and I will, we could go all day just talking about how we make this stuff because it’s so fun. I think with any creator, they feel that way. They’re in the business of creating stuff. And if you think that we’re not doing it the way you want, write me. I can even tell you, I would tell that person, “I’m just not your audience.” However, when you tell people to skip it, think about this other person over here that’s totally intimidated. Has no idea. They cry about their money, right? They have no idea about the stuff Emily talked about on the episode when you and she were together about mindset, about getting in the right spot… They don’t know any of that stuff. So, yeah, skip it if you’re you. But maybe not everybody. 


Tom: So for anyone that thinks this is for them, if they haven’t seen Emily’s episode, check out They’ll probably also like your podcast. Can you tell them about Stacking Benjamin’s? 


Joe: We have fun. Mr. Drake has been on before. It’s been too long, my friend. We’ve got to reprise Tom Drake being on. I think you’ve been on two or three times, haven’t you? 


Tom: Yeah. Normally when you need a Canadian joke thrown or something.


Joe: We did that last time. We had a lot of fun, didn’t we, Tom, with the Canadian thing. And by the way, somebody did get offended about that. 


Tom: Yes, you mentioned that to me. Yes, yes. 


Joe: I said, “Wow, the Canadian was even making fun of these terms in this stuff!” Anyway, it’s That’s the website but the podcast is where you find all your podcasts. We publish three times a week. Our second-biggest audience is Canada. Our third biggest is Great Britain, and then the fourth is Australia. We do get into US tax law sometimes, but our show is definitely meant to be for a wide audience and is generally country agnostic. There’ll be that 10 percent, though, where we’re talking about how IRAs work but you can just fast forward through that. 


Tom: Great, thanks for being on the show. 


Joe: Thanks a ton, man. 


Thank you, Joe, for your insights on everything from goals to risk, to insurance, and more. If you enjoyed this episode, you’ll love the new book. You can find the show notes for this episode at along with a link to pick up Joe’s book. As usual, head over to the YouTube channel and subscribe there as we’ll be getting back to releasing never-before-seen content, soon. Search for Maple Money or go to and subscribe today. I look forward to seeing you back here next week when we’ll be chatting with Carley Thorne and Mercedes Gaztambide from CBC’s newly relaunched Money Sense. See you next week! 

If I could make a book that is like the Hardy Boys detective manual, but adults carry it around like that, but it’s about money, that is the tone I’ve been looking for. - Joe Saul-Sehy Click to Tweet