8-Figure Founder Shares Secret to Making More & Working Less with Jonathan Goodman – EP 221

Justin Donald: What's up, Jonathan? Good to have you on the show.

Jonathan Goodman: Hey, this is exciting. As somebody who read your book before I knew you, this is really exciting, Justin.

Justin Donald: Well, I can't wait to chat. By the way, you're supposed to be in town. We're supposed to be recording this live. But I think for both of our schedules, this actually worked out great where we can do it remote. And I just find podcasting so much easier to do remote type of sessions but YouTube really likes the in-person both people. It populates better. So, I have this love-hate relationship with the coordination of an in-person but how it performs on YouTube is always better.

Jonathan Goodman: I feel like if it's your full-time thing when posting is better. I popped out to New York City. I'm from Toronto, right? So, I popped out to New York City for a day and just basically went around the city doing live. And I was going to do the same thing in Austin for three days. And then I kind of thought more deeper about it. I mean, I have a seven-year-old and a two-year-old and a pregnant wife, and we're living in Mexico in the winters. And I have this book coming out. I have a book that's just come out and then I'm just about finished the first draft of the next book. And I'm like, "You know, like let's 80/20 this for a minute."

Justin Donald: Yeah, that's the way to do it. And you're at a point in your life where you don't have to be maximizing everything anyway. You've done well for yourself and we'll get into that here.

Jonathan Goodman: Yeah, we'll talk about it.

Justin Donald: Yeah. I'm excited to chat and really I'm just thrilled to be able to tell your story. You and I, we met at Mastermind Talks, so thanks to Jayson Gaignard. We appreciate that connection. And the first small group that we put together or that was put together for us, we were in that group together. And by the way, you'll be pleased to know that I'm actually hanging out with Sean on Friday. So, the three of us are actually all hanging out this week.

Jonathan Goodman: I love it. I love it. Sean's such a cool guy. He's nutty in every wonderful way. This dude, somebody who writes that many books, I think has to be a little bit of a nut.

Justin Donald: Yeah. How many books has he written? This is crazy.

Jonathan Goodman: I know. Written or ghostwritten?

Justin Donald: Yeah. I mean, it's over 100, I think, right?

Jonathan Goodman: Well, he's got a machine of other writers who work with him. And so, he explained it to me once. He's very, very good at coming up with a theme, coming up with the characters, coming out with the general story structure. And then he basically just has other writers fill in the gaps and then he just comes up with the next framing or scaffolding. I might have gotten that a little bit long, but that's kind of what it is, which is not uncommon to a lot of the authors that we know. I had somebody on staff for a number of years who wrote a number of Goosebumps, of Sweet Valley High books. He also did a lot of the cover stories for like GQ and stuff. He was the guy they'd fly out to interview Hugh Jackman.

But he told me he's like, "R. L. Stine literally just sat there and came out with the idea. And then it was just monkeys on typewriters. There was like 20 of us who were just basically writing these books' content all day, every day." That's how a lot of this stuff has come to be, so.

Justin Donald: That's awesome. Well, he's a genius. Sean Platt is who we're talking about just to make sure we give him a proper shout-out.

Jonathan Goodman: It's cool. It's cool figuring out what goes on behind the scenes of this stuff, a lot. Yeah.

Justin Donald: Well, you've written a ton of books, right? Eleven books. Is this your 12th or is this your 11th book?

Jonathan Goodman: This is my 12th. This is the first traditionally published book. All the other ones have been self-published. And take it with a grain of sand like this is my 12th book. Three of them were ghostwritten, actually, by this guy who did the Goosebumps and the Sweet Valley High. And one of them was a textbook. One of them was a children's book with my wife. But, yeah, most of them have been business nonfiction. And, yeah, it's been fun to work with a publisher. A lot of people kind of pooh-pooh the idea of traditional publishing, particularly if you already have a platform, particularly if you already know and have the contacts to like self-publish well and professionally.

I have found the experience to be quite wonderful, start to finish. The product that we've put together with the help of my agent, the publisher, and editor, and everybody has been so far beyond anything that I've ever been able to do with teams that I've been able to assemble to the point where I'm actually embarrassed by my previous works because of I look at this one and now this is what I compare everything to, which I think is a good goal to have whenever you take on any project.

Justin Donald: That's right. And we all evolve, you know? So, it's like what at one point you were proud of, ten years later you're embarrassed of because you're like, "Oh, it's so elementary. My writing style was so boring or whatever." So, I mean, when I just launched the Updated and Expanded Edition of Lifestyle Investor, I mean, the gap in time there is only, what, 4 or 5 years.

Jonathan Goodman: I was going to ask you, how many years? Yeah.

Justin Donald: And I felt the same way. I'm like, "Ugh, I didn't like the way that sounded or that flowed," and, "Oh, I should have expanded on this." I mean, it's like I could have rewritten the entire book. I really could have.

Jonathan Goodman: Yeah. I find that particularly the books and the stuff that I've written in the way that I communicated when I was young, I felt like, I don't know, maybe you'll resonate with this. You wrote that book a lot more mature and with a lot more life experience than I wrote my first book. I mean, my first book I self-published as a 24-year-old personal trainer and it was a book of how to be a good personal trainer, right? And so, I feel like looking back, I was overcompensating a lot for a lack of confidence. Like, "Who am I to write this book?" to the point where my friends call me John, but my professional name is Jonathan. My real name is Jonathan, but my friends call me John.

The reason why Jonathan is on my books is because when I was 24 and I self-published my first book, I wanted it to seem like I was older than I actually was. And I felt like the name Jonathan felt older than the name John. And so, now I'm stuck with that name on my books. You know, it's all of these little silly things.

Justin Donald: That's really funny. Well, I love learning some of the inside scoop here. You're a prominent figure in the fitness industry, so I like hearing about this. I think your first really big book was Ignite the Fire.

Jonathan Goodman: Yeah.

Justin Donald: Because that maybe have over...

Jonathan Goodman: I mean, that was the one at 24.

Justin Donald: 1,000 reviews on that one, right? Okay.

Jonathan Goodman: Yeah. That one sold over 100,000 copies.

Justin Donald: Wow. And so, was that geared towards trainers or anyone that wanted to be fitness-minded?

Jonathan Goodman: Ignite the Fire is a book for personal trainers on how to have a successful career. It was really the first book. I mean, now it seems so obvious to say this, but it was really the first time somebody in the fitness industry came out and said, "Y'all, I think we got this wrong. I think probably the importance of the quality of the workout that you give to a client pales in comparison to the importance of your ability to get somebody to want to do that program." Like, there's a lot of ways that somebody can jump up and down and sit down and stand up and lift something up and put it back down that will get them in good enough shape for their goals. What actually matters more is that they want to do it and that they do it for long enough that it makes an impact.

And so, the book was a lot more centered in psychology than it was centered in physiology or biomechanics, which at that point was quite rare. I mean, now it's pretty commonplace in the fitness bit. And then, I mean, I talked about business and how to structure your career and how to develop yourself personally when you're young in your career so that you kind of think long term, like how do you optimize mentors, how do you optimize learning early on and recognize opportunities for that early on that might actually even involve the tradeoff of perhaps a lower salary. How do you optimize for different types of opportunities over the course of your career and then different income streams, all that kind of stuff?

Justin Donald: Well, and you've got a bunch of income streams. We should talk about this. You started several businesses, so you're a founder on many levels. I believe one of your businesses is you have over 200,000 customers in over 120 countries around the world at $35 million in revenue. So, that sounds like you figured a few things out. You got into real estate investing early. I mean, let's tackle some of these things. Tell me a little bit about your businesses. And I think one of them is a software business, right?

Jonathan Goodman: I have a software company as well. Yeah. I mean, my entire model was based off of my life and business philosophy, which I call whales and minnows. You know, the cover of my book, The Obvious Choice, there's a whale made out of a $100 bill chasing a bunch of pennies. That's whales and minnows. The last chapter of the book is Whales and Minnows. And the idea behind that is quite simple. It's make it free or make it expensive. Show up or don't show up. Do the thing or don't do the thing. I think a lot of the time the problem that we fall into is that it's just so easy to kind of dip a foot in.

In a world where we all have a recording studio in our pockets, on our phones, where we can spin up a website for free, we can send out an email blast or social media post for nothing and have them access everybody maybe, but probably not, it's too easy to do a bad job these days. And as a result, a lot of people do but it feels like work. It feels like progress. And so, my entire structure is based off of I'm going to feed the whales, I'm going to sell to the whales, and then I'm going to use the spin-off of those high-profit enterprises to feed the minnows. And some of those minnows will eventually grow into whales, but other ones won't and other ones, I can feel good that I'm doing a good job for.

So, at the lowest level, I've got my books. My books aren't free, but they have zero expectation of service. And that's the line for me. Nobody buys a book and expects the author to service them in implementing the information in that book. Now, if I did a low-end membership site, for example, there would be an expectation of service.

Justin Donald: That's right.

Jonathan Goodman: And so, I've learned that the hard way. I've had three membership sites. Right? Two six-figure, one seven-figure membership sites, and I've shut them all down. One was a physical newsletter that we had. Yeah. We launched it at $40 a month and we had 1,516 subscribers on day one, and then we put it up to $60 a month. We ran that for ten months and then I had to like more conventional membership sites like protected information behind a password, that type of thing. I didn't like those because they require too many customers. And there was just a high expectation of service throughout, whereas books don't have that.

So, on the low end, I've got zero expectation of service. And then I have basically coaching programs, right? And I like coaching programs. People, "Oh, you shouldn't be in a service business. They're not scalable." It's like they are scalable if you know how to scale a coaching business. I think coaching businesses are one of, if not the best businesses to own because they kick off a lot of cash up front. You can run them at an extraordinarily high profitability like we run a coaching business that's at a 65% profitability.

Justin Donald: Yeah, that's nice.

Jonathan Goodman: It's very nice. They kick off a lot of cash upfront but I don't, just my own personality. I'm really, really good at starting things. I'm really, really good at taking things from 0 to 1. I'm not good at running things ongoing. I know this about myself. You would not want me as your coach. I would be a terrible coach. So, I own two coaching businesses. I have not worked a day actively in either coaching business. And so, they're fantastic businesses and both coaching businesses are basically people in fitness. I wrote the textbook for online fitness, so I kind of created that industry back in like 2012.

And so, both of those are for people who in person want to transition to online coaching and then people who are already online coaching and want to kind of scale up through online coaching. So, it's aspirational. There are two levels. What you do to get to 0 to $5,000, 0 to $10,000 a month is very different than what you do to get from 10 to 100, 200, 250. What you do to get from $250,000 to $1 million is very different as well. So, you kind of need different programs and different structures within those. So, I've got those two coaching businesses.

Justin Donald: And by the way, did you start those or did you buy those?

Jonathan Goodman: No, I started those. Yeah, I started those. I started those. I built the model and then put the operator in place. I believe very strongly in insane incentivization structures for key staff. I have figured out over the years painfully that one person who is stellar at their job, incentivized properly, is worth 50 to 100 people who are just good to okay at their job. And so, almost all of my expenses, all of my core expenses are directly tied via profit sharing or commission structures to revenue. And that works really well. That's not like a growth-oriented strategy. That's a John sleeps better at night optimization strategy. I don't worry about payroll because, by definition, a payroll is much higher.

That means that we've taken in much more money and that's very different than how things used to be. So, that works out really, really well. And then, yeah, I mean, I started a software company called QuickCoach. We have 43, 44, 45,000 users or something, and that's kind of my like moonshot bet. I knew what I was signing up for there. I knew that the odds that it worked were relatively small. It seems to be working. I recognized an opportunity in my industry on the low end. You know, 92% of personal trainers never have more than ten clients at any given time.

Justin Donald: Wow.

Jonathan Goodman: All the software platforms that exist that sort of trainers are what software, what SAS platforms tend to do, which is they go out and they get funding from private equity, VC, whatever, or they build and then they get funding later on or they get bought or whatever. And their goal is to basically invent new features so that their users pay more and then they charge based off of the amount of users that their customers have on the system. So, in this case, it's like, "Oh, if you're a trainer and you've got less than two clients, you're free. If you've got, whatever, 5 to 10 you're at this price, 20 plus you're at this price, 50 plus."

I decided to enter in the business with a different business model, which is really on the low end, serve the minnows with this scalable solution that by definition is simpler. No integrations. No automations. I wear a Casio watch because it reminds me to solve the problem simply and never touch it again. My software platform is the BIC pen, is the Craigslist, is the Casio watch of the software world. And the only reason why I was able to do it is because no other platform in my industry has a personal, recognizable face or brand behind it. And so, I'm able to acquire customers, win users in a way that other people aren't. Their user acquisition costs are simply too big to be able to attack this market on the low end where the majority of the customers are.

And so, any time that I'm trying to spin something up, it's like, "Do I have a really significant competitive advantage moat in this? Or if I don't, I'm not going to do it." So, the software seems to be working. It's profitable month over month. It's not crazy profitable month over month, but it's profitable month over month. And the nice part about it is that the expenses won't scale because it's kept simple. So, those are the businesses. And then like any good active business, Justin, I feel like it's silly telling you this because you know this better than I do, the best way to make money is with money. Well, I mean, my investments make way more money than my active businesses do.

And it's not even close. I mean, it's to the point now where it's just kind of silly, like to the point now where I look at how much money I'm making through my active businesses and I'm not really that motivated to work in them.

Justin Donald: That's right. Good to have good people then, these comp structures that you were talking about.

Jonathan Goodman: We could talk about the investments but I think that that's understated, though. And that's why I love the work that you're doing so much is because really, for most of us, I think that the goal of any active business is to make money so that you can make money with your money.

Justin Donald: That's right. Well, let's talk about some of your investments. Before we do, can you give us an example? You don't have to give away the exact secret sauce, but are you willing to share an example of what some of the comp structures are or look like or are even approximately like? Because there are probably a lot of people tuning in here that they have acquired a business or they want to acquire a business, but maybe they're unsure how to structure it in a way that they're worthy. They won't get an operator or the operator won't stick around. And it sounds like you have solved for that because as I always tell people, if you are incredibly generous on the split, and you've got to find the right person for this.

Jonathan Goodman: Yes.

Justin Donald: So, it's got to be the right person first and foremost, right? They need to have a work ethic. They need to be trustworthy. They need to be hungry. So, there's a certain skill set that you're looking for and a certain avatar you're looking for. But if you are extremely generous with the splits, they will stick around. So, I'd love to hear some of what you've done.

Jonathan Goodman: Yeah. So, there's a couple of different components of it. You can kind of poke at and pull at any of these strings if you want, Justin, but there's kind of three different components of it. And so, you have individual contractors, so for example like my content team around my personal brand, right? So, that's one where it's really performance-based incentive. Then you have the most obvious, the most common is anybody associated with sales so sales team, whether it is sales team on the front end like DMs, DM setting, like that type of thing, or whether it's phone sales team. We have both of those departments. And then operators of the business.

And so, my philosophy and there's a lot of people who have different philosophies. I'm not saying that this is right, but my philosophy is I really want ownership. And so, I actually still own 100% of all of the businesses that I have. I still have 100% ownership of everything. But in one of the businesses, for example, there was a number of profit shares associated with it. And so, I give away 50% of the profits in that business to a variety of people every quarter that they come in. And so, we have a lot of agreements as to what are the expenses of the business. For example, the salary that I take, part of my salary is considered an expense in that business.

So, one of the hardest things about profit share is you have to be very, very clear and really calculate well what is considered an expense and make sure you are on the same page because it can get very nuanced and very detailed and you don't want any bad blood. So, that just comes out every quarter. Like, if you are operating this company for me, you have $0 of a salary and you are 100% incentivized with this profit share. The same type of thing with a lot of our salespeople where they have zero... One of them actually has a, you know, she has kids. She's the major breadwinner in her family. And so, we guarantee her a minimum just because that makes her feel safe. She's always been well above that.

And we're both on the same page. We're like, "If you hit this minimum, you get a warning. If you hit this minimum twice, you get two warnings. If you hit this minimum the third time, like this is not working," but she's guaranteed a minimum. And then it's just you eat what you kill. I mean, it sells. It sells. And so, it's some combination of how many calls are booked to how many calls are progressed to the next call to if they convert to a customer to if that person renews longer. Our coaches own a little bit based off of their coaching but they're actually largely incentivized based off of whether that person stays longer. And so, they're incentivized based off of renewals.

Like, you want to incentivize the behaviors that you want to see in your business. Is that person going to renew? We can get them to sign up. The true measure of any successful business, especially one where, I mean, in this high-end coaching business we're talking $9,000 for three months. That person has to get a lot of value over those three months to renew at $17,000 a year. And then if that person renews like we just had somebody renew for the fourth time for the fourth year and he's been with us since day one in that business. Like, your coaching team has to provide a lot of value there so make sure you're incentivizing the right behaviors. And then the final one, this is actually my favorite because I think what a great incentivization structure does is it self-selects out the wrong type of people.

Justin Donald: Yes. Totally.

Jonathan Goodman: And so, what I will often do, for example, the two key guys that are on my personal brand content team, one of them is more for written stuff across Twitter. The other one is more for video stuff across YouTube and TikTok and Instagram and stuff. And the one across Twitter is on like kind of my book strategy team as well. They are both very much incentivized based off of performance. And they came to me and they said, "This is the amount of money that I want to make." And I said, "That's great. I want you to make that money, too. I want you to make way more than that. But I'm not going to pay you that unless you hit these goals." So, what we did together is we set low, medium, high.

So, for example, one of the guys, "Okay. Low, medium, high with this book launch. Number of books sold via pre-launch and first week, low, medium, high, with a kicker for a number of Amazon reviews that we get within the first five months." Okay.

Justin Donald: That's nice to tie that in. That's really clever.

Jonathan Goodman: Because those are the two most important things, right? Like, I want to give my book the best chance of success. If it's as good that I think that it is, it's my responsibility to start a ten-year flywheel at launch. And then the market will prove that out or not but I got to give it the opportunity. And so, what I basically said to him is, "Okay. You want to make this amount of money per month. You want to make whatever it is." I'm just going to use round numbers. These are not the numbers. "You want to make $10,000 per month. Okay. I'm going to pay you $4,000. I'm going to guarantee you $4,000. And then at launch, if we hit the low goal, I'm going to talk you up to the equivalent of if you made $10,000 at launch."

So, he joined me four months ago, right? So, six times four, 6, 12, 18, 24. So, I'm going to give you a $24,000 bonus. If we hit the medium goal, I'm going to give you a $35,000 bonus. If we hit the high goal, I'm going to give you a $75,000 bonus. Like, insane bonus, right, for this guy like to the point where you will have actually owned $18,000, $20,000 a month for the work that we did together. But you know what? You earned it. And then five months out whenever we hit, I think a goal was 1,000 Amazon reviews within the first five months. So, whenever we hit 1,000 Amazon reviews, so long as it happens within five months, you get an extra $15,000 bonus. The video guy is similar where we're putting a push into YouTube. Haven't really started yet, but we're putting a push into YouTube beginning of January.

And so, it's the same type of thing. Low, medium, high. You told me that you want to make X amount of dollars. I'm going to pay you like a third of that guarantee because you got to make some money. But then if you do what you say that you're going to do at the lowest level, you're going to make exactly what you want to make via YouTube subscribers. So, what we have is YouTube is primary and then Instagram is second. Okay. So, if you hit this low goal on YouTube, then you get whatever you asked for. If you hit this low goal in YouTube and you also hit Instagram, you get this bonus. But if you just hit Instagram and you don't hit YouTube, you don't get anything. And then medium, high, the same type of thing.

And we have that at 3 months, 6 months, and 12 months for the first year that we work together. And the nice thing about that is these guys are amped up by this. They're young. They are hungry, man. But I was interviewing podcast production teams and I offered a deal similar to this, to a podcast production team.

Justin Donald: They didn't like it.

Jonathan Goodman: And they said, "This isn't how we work. This is our fee per month."

Justin Donald: That's right.

Jonathan Goodman: And I said, "If you truly believe that you're going to do what you say that you're going to do, I will give you enough to make sure that your team is paid. Basically, your profit, Mr. Owner, of this podcast team is dependent on your success of how good of a job that you can do. And if you do that job, great. If you do a better job based off of these agreeable deliverables, you're going to make way more like stupid amounts of money." And they said, "No, we can't work like that." And I said, "Great, I'm not working with you." It self-selects out.

Justin Donald: Yeah, there are very few people in that industry I think that would work on a model like that. So, yeah, you're going to get a lot of self-eject.

Jonathan Goodman: You are. But that's what I like about it though is I have found that you kind of need a proxy, a very quick proxy these days to call up not saying that this team is necessarily bullsh*tting me, but it's a very quick proxy to be like, "Eh." That's a data point that they might not quite believe themselves what they're telling me. Or they're just not willing to go to bat for me the same way. I mean, these guys are my personal brand media team, a 19 years old and I think 26 years old. I'm 39. Like, they exist in my blind spot. Like, I don't know what they know. I don't know the people they know. I've never watched a YouTube video start to finish in my life. That's a blind spot. You know what I'm saying?

Justin Donald: That's a blind spot. Yeah. And they're matter experts, right? They're the area experts. I mean, they know it inside out.

Jonathan Goodman: And being able to say to them, like, "You're 19 years old. I know how much I'm paying you. And by the way, I also have a reasonably good understanding of how to invest money for the long term. And if I'm paying you this money like I'm happy to talk to you about this and share resources with you so that this one job that you're doing with me could actually set yourself up for life."

Justin Donald: That's awesome. I love that. And you're painting the picture long-term.

Jonathan Goodman: It's a strong motivator.

Justin Donald: Hey, let's talk about investments because you made a comment that I loved. You had said, "Hey, if we are really valuing what my business has produced versus what my investments produce, it makes all the sense in the world that I live in the investment space, not in the business space." Now, I can tell that you get energy. You like your team. You're doing some great things right now and business is humming, but it takes a really special person to be a great entrepreneur and a great investor. And so, I'd love to talk about some of your investments that you've done and the returns you've got and I know you've invested in I think you have 13 different rental properties. And I think even if that were the only thing you've done, that's a big win. But I'd love to hear about some of the wins and some of the losses.

Jonathan Goodman: Those are actually by far the worst investments that we made.

Justin Donald: Oh, are they?

Jonathan Goodman: Well, the first one was good. The first one was good. We bought an illegal duplex in a town called Midland just outside of Toronto, kind of like a cottage town. And we renovated it and turned it into a legal duplex. And then COVID happened and the price jumped up. And actually, ten months after we bought and renovated that property, we took 110% of our principal out.

Justin Donald: Wow.

Jonathan Goodman: And just left it and used that money to renovate our kitchen at home, but also buy three more investment properties in Sudbury. So, we told the bank that we were going to renovate our kitchen at home. We remortgaged our house. I mean, this was just sh*t dumb luck but we actually remortgaged our house at a lower mortgage rate, took an extra $200,000 out, added that to the money from that one house, and bought three more houses in Sudbury. And I think one's a five and two are triplexes. But in remortgaging our house, in Canada, it's five-year terms. And so, what we actually did is we reset the clock in the end of 2020 at 1.89%.

Justin Donald: That's nice.

Jonathan Goodman: For another five years.

Justin Donald: Yep. So, that's coming up then soon.

Jonathan Goodman: So, that's coming up at the end of next year. Yeah. But, I mean, mortgage rates are not 1.89% anymore, right? And so, we reset the clock.

Justin Donald: What are they by you?

Jonathan Goodman: You know what? I don't even know. I haven't even looked into it.

Justin Donald: Okay.

Jonathan Goodman: I don't even know. I know that we are on variable for all the rental properties, and it's cut them pretty thin, you know? They're cash flow positive. That first house, we've had to put a little bit more cash into, not a lot but a little bit more cash into because when we refinanced it. We just cut it really close. But we've also taken 100% of our principal out. So, that's fine. But those have actually been our worst-performing investments as a whole. They're fine to have but in Canada, real estate is weird that way. I mean, our house in Toronto, I don't know, we bought it for $1.55 million. It's probably worth about $2.5 million now. These 13 properties together are not worth half that, probably not even worth a third of that. And so, that's just the difference between Toronto real estate and maybe Vancouver and everywhere else in Canada.

Justin Donald: Yeah, that's interesting. And by the way, I know I have a lot of Canadian friends that will not invest in Canadian real estate. They will only invest in U.S. real estate interest, like many of them. I mean, enough that it's a pattern.

Jonathan Goodman: Yeah. I mean, if I'm completely honest, the real estate investing was a project that Alison really wanted to take on. You know, this was a number of years ago. Something that I really wanted to do was build our own family's personal philosophy towards wealth management, like how do Alison, my wife, and I think about money. Are we going to try to optimize wealth? Are we going to try to optimize lifestyle? Where is the line? What's enough? What safety blankets do we want? And so, I talk about it in this book just the importance of what I call leapfrog learning. Basically, you kind of want to attain a mediocre to low-level skill set in a whole bunch of leapfrog complementary skills to your core industry expertise.

And the best part about that is with enough focus, you can actually attain probably a good enough knowledge on that thing in about 60 days. And so, for me, wealth management was one of those. So, Alison and I both took 60 days a number of years ago. And the first thing that I did was I read a book just about money. Like, I have a kinesiology degree like I never studied anything like this in school. So, what does that mean? Where does money come from? What's monetary policy? Like, what do these terms even mean?

Justin Donald: Props to you, man. Most people don't even, you know, if it's not in their lane, they stay away from it. So, nice job saying, "Hey, I know nothing about this. I'm a kinesiology major. I've done well in the fitness industry, but I know nothing about money."

Jonathan Goodman: How do we figure this out, right? So, step one was what are these terms? And then step two was, okay, now we need to learn how to think about money. Because I knew at that point that my goal wasn't to make as much as possible. But then, okay, there's still a wide range. So, that's when I came across your book, first off. So, I read your book and I read. I'm a reader. Alison is a listener. So, Alison listened to a lot of podcasts. I read a ton of books on trying to gain insight into other people's philosophies in money, particularly people who work in the money industries. What do they do with their own money?

There's that stat. I'm going to get the numbers wrong, but it's something like 90% of mutual fund advisors don't invest in their own mutual funds. Like, what they say to do professionally and what they do do personally is often quite different because the game that they're playing, their desires, their rewards, the risk tolerances, their patterns in life are different than some of the people that invest with them, right?

Justin Donald: That's right.

Jonathan Goodman: It's just important to appreciate that there's good information for others that can be bad advice for you. And so, where is that line? And so, Alison and I built over the course of that period basically what I call my four buckets of wealth. And it's largely based off of quality of life and also just like safety nets. You know, I don't want to worry. I want to make sure we have enough, but I don't want to worry. And so, you've got conventional stocks, real estate, Bitcoin, and then personal brand reputation. And I view personal brand reputation, at least for my career, just as important to invest into as a stock.

Justin Donald: Yeah. Super smart.

Jonathan Goodman: And so, I started to look at it in those buckets. And it was more I want to hedge against the inevitable. Like, if one of these things gets taken out, I don't know which one of these things is going to win big but if one of these things gets taken out, we're still going to be fine and therefore we will be able to sleep well at night was kind of the...

Justin Donald: Yeah. I love that.

Jonathan Goodman: The thought process.

Justin Donald: The wealthiest people in the world, they diversify. They don't have all their eggs in one basket and they do quite a bit of diversification. Now, I'm curious. You and I were talking off-camera and you did really well with Bitcoin. I'd love to kind of hear the story because you kind of push some chips in early on in a way that I think maybe a lot of other people wouldn't do it. I mean, this is before it was really popular, I think, to kind of like be building a treasury in Bitcoin, right?

Jonathan Goodman: Yeah. So, I mean, it's funny because I didn't have a language for it back then. But in the end of 2019 all throughout 2020 into 2021, I systematically put 15% of my holding company's investment into Bitcoin. So, yes, I guess, I created a Bitcoin treasury and I just held it. It was just investment. I bought it super low. I bought it as it went up. I bought it as it was coming back down. It just didn't matter. It was kind of the Michael Saylor approach. It was like I do believe that this thing is going to go really, really high or it's not going to work. And if it's not going to work, I need to only put enough in that If I lose it all, I'm going to be fine. If it does work, it's completely irrelevant what the price is today.

Justin Donald: That's right.

Jonathan Goodman: And so, there's no point in even thinking about whether I bought it at. And so, I started buying at $30,000. I bought all the way up to $65,000 to $66,000. Like, I put $150,000 in it, $66,000 just before it crashed back down to $16,000. So, that felt horrible, right? But the way that I was able to mentally get over that and not watch the price every day and not panic sell or anything was this is the philosophy. This is the approach. And a lot of that came from the antifragile approach, Nassim Taleb's work into just understanding asymmetry. There's only been one other case in my life where I've looked at something and I'm like, "There just seems like there's something here that's really interesting that I've never really seen before."

If this works, this seems to be very, very clear that it is an unbelievable asymmetric bet, whereas if this works, there's basically no way that this is going to work small or it's not going to work at all. And then I looked at Bitcoin and all of the study that I did into money helped out, all of this work that I understood about asymmetry helped out. And what's money if nothing other than a story? Money is something that we all agree has value. It's not backed by anything, whether it's seashells, whether it is Bitcoin, whether it's dollar bills. The only reason that it has value is because the collective we decide that it has value. And so, then you have to appreciate the fact that there is a power in this story. And the more people that buy into the story, by definition, the more power that that story has and the more stable that story becomes. That's like there are millions upon millions upon millions of different people scattered around the world that own Bitcoin that have bought into this story. The odds that this can fail are getting smaller by the day.

Justin Donald: Agreed.

Jonathan Goodman: For no other reason than there are just too many people that agree that this thing has value. And so, I was like, "Okay. I have never seen this combination before in my life and I have not ever seen it since where there is this thing that exists where so many people are already bought into it that it absolutely could go to zero. But the odds are pretty small simply because the story has already grown to be so big and so generally accepted. And if it works, it's going to work big enough that I probably will never have to think about money again."

Justin Donald: That's right.

Jonathan Goodman: And so, I mean, I thought that I was crazy as I think everybody thought that they were crazy but it's too clear cut to me. And so, it was like, "Okay. Well, what's 15%? Let's do 15%. Let's do what everybody says dollar cost average." But dollar cost averaging was like $100,000 at a time. It was not small amounts. I did a couple, I did a bunch of big buys, and then I just did every single week. I just buy $8,000 or $9,000. Just every Friday at noon $8,000 or $9,000, didn't matter. And yeah, I mean, I held on to it. I sold the first bunch of it. Canada had this income tax raise in the period last year. And so, it was kind of confusing how they did it because the Canadian government likes to kind of hide tax raises behind confusing nonsense.

But they basically rose taxes on investment assets, about 9% on capital gains. And so, sheer dumb sh*t luck, my advisor also bought a lot of NVIDIA for us at $60 way back in the day. And so, we had this NVIDIA and this Bitcoin that had gone up so much. And so, we sold some of both, realized the gains. I have a huge tax bill this month that I just shifted money around. And then I mean I don't intend to sell it again. Like, not to say that I never will, but it was that philosophy of, you know, it was that approach of, "Hey, let's build our family's philosophy to what matters. Let's try to recognize these signs. Let's be very, very patient until there's an opportunity to be very, very aggressive and jump on it."

Justin Donald: Yeah, I love it. I'm absolutely in it for the long haul. I think at this point we've got mass adoption. We've got a pro-crypto government.

Jonathan Goodman: Well, that's the interesting thing.

Justin Donald: This is the wild card, right? So, if Trump moves forward and does create the Bitcoin reserve, which he said that he's going to do, well, now all the other G7 countries have to follow in suit. You're going to see more Fortune 500 companies having a portion of their treasury in Bitcoin, having some sort of a reserve corporately and holding it on their balance sheet. And I just think you're going to see this trickle-down effect from sovereign nations to the biggest companies in the world. And some of these biggest companies in the world, their value is greater than the value of these nations, right, than the GDP of many of the countries. So, like some of these companies are like sovereign nations in terms of control and power and output. So, yeah, I'm very bullish.

Jonathan Goodman: It would be very interesting to see what happens in the coming year, really, with the Trump government, with the pro-crypto government. Whether it happens now, whether it happens later, I think it's going to happen. I mean, if they establish a strategic reserve, Bitcoin is not just going to go up a little bit in price, right? Because the question is like how much is there actually left over? You know, 21 million is the cap. You've got a million in Satoshi's wallet that has never moved that, by all accounts, will never move. I mean, it's probably lost. Whoever was Satoshi or whatever group has probably passed away. And so, but then you've got all of the people who have just lost theirs.

Justin Donald: Yeah. People, approximate 4 million, right? 3 to 4 million.

Jonathan Goodman: So, how much is actually left? It's a smaller and smaller number but I don't know. I mean, go back to like the lifestyle thing. You talked about the real estate and I talked about how it hasn't performed that well for us. We also own within our portfolio, now, this is all through my advisor, but we also own reasonably significant holdings in a student housing holding company. And that's performed really, really well. That company actually just got acquired, so there was another 30% bump in that fund. But that's performed really well. But what I have realized, I guess, is that you can get exposure to real estate without physically owning the house. You know, we have a JD that handles it.

Justin Donald: Most certainly.

Jonathan Goodman: But this company, Alignvest, or whoever that owns hundreds and hundreds and hundreds of student houses is going to be more efficient, is going to have better systems, is going to have economies of scale that we don't have without 30 units across four properties.

Justin Donald: That's right.

Jonathan Goodman: And without the headache and everything. So, if I had to do it again, if I'm honest, I would not buy the physical houses. I would buy the holdings.

Justin Donald: Yeah, become an LP, a limited partner in a syndication or a fund. We do a lot of those and I...

Jonathan Goodman: Do you? Okay.

Justin Donald: By the way, there's the sacrifice so it's not that one is better than the other. You can get a higher return when you own deeded property, but you also have a lot more work. So, on the LP side, if there's a GP, a general partner that's running it and they're actually good at what they do, as an LP, you're going to make less than what you would with deeded property, but you don't have any real responsibilities beyond just vetting the deal at the onset. So, a lot to love about that. One more thing I want to talk to you about before we wrap things up here today. You've got a killer life. You've traveled and lived in over 13 countries. And one of the things that I love about you is every year you travel abroad for 4 to 6 months, I believe.

And I'd love to hear, A, just why you've chosen to do this and, B, like why this is a priority to you. Because like you, I love to travel. I haven't lived in 13 countries, but I've traveled to probably close to 80, probably over 80 now. And we've done, you know, we've lived abroad for a month or two, but nothing, I mean, you've gone much further than I have on this. And I just love to hear your thoughts because you've got a pretty epic life from the travels, I mean, in general, but from the travel side of things, it's awesome.

Jonathan Goodman: Again, there's trade-offs, right? It's what are you optimizing for? The only way to maximize is to minimize. You need to eliminate all of the sh*t that does not matter to you in order to maximize the very few things that do. And so, I think the first step is to really become true to yourself and figure out what really matters to you and how can you optimize every ounce of your day and your investment strategy and your work for that. Your question's a good one. Why? I think why we start doing something is very different than why we continue doing something. Why did I start working out? It's because my dumb adolescent self thought that if I got muscles then girls would like me more.

Why do I keep working out? It's because it's my mental health outlet. It's because I want to beat my kids at sports until I can no longer beat my kids at sports. It's because I don't want to hurt. It's because I have found that exhausting the body is a way to energize the mind. The work that I do, particularly writing, requires me to sit for long periods of time. Sitting and thinking for long periods of time is energetically and physically very, very taxing. You have to be fit. I want to be able to write books and to do this creative work for a very long time. The only way to do that is to keep my body strong. And so, why I started doing the thing is very different than why I continue to do the thing.

Why do people start traveling? It's because they want to see the world. Why do they continue traveling? It's because of what the world teaches them about themselves. And so, the real reason now that I pick up and leave every year, I call it the eight-four rule. And it's because I have realized that for me, seasonality in my life is very important to maintain. I get burned out if I live one way for too long, no matter how good that way of living is. And so, in the period where I'm in Mexico like right now I'm in Mexico, for example, in the period that I'm here, I'm in Mexico for four months, four and a half months, it's very much optimized towards creative work, family, and fitness. I am not pushing forward on I call it work or business at all. And it's a chill lifestyle. You know what I'm saying?

Like, people here work to live. They don't live to work. The energy is much more laid back. People are not on time when they do stuff. They sit around for a lot longer. They drink juices which is great. I love that until I don't and then I need to get the hell out. And then in Toronto, it's a much more frenetic, fervent energy. People there are trying to get ahead. Everybody's on time. It's all networking. It's push, push, push, push, push. And I love that energy until I don't and then I need to get the hell out. But what I've noticed is that these stops and starts naturally fill my cup in different ways and allow me to be excited and energized for the period that I'm in because I know that there is an end and then get excited and energized for the next period.

And I have found that it has been very, very key to avoiding burnout or what I call bored out over the course of my life. The other thing that it's done and here's the coolest thing, here's the thing that I only really started to realize the last couple of years is that what I actually do is I clear my schedule, I clear my calendar, I wipe everything off whenever I get to a new place. So, a minimum of twice a year, every single year for the last 13 years, I have wiped my calendar clean. And then I've built anew from first principles, from priorities, from big rocks. And I reassessed my priorities…

Justin Donald: It's changed over time, too. That's right.

Jonathan Goodman: Which change and iterate. You know, humans abhor a vacuum. We naturally add, but very rarely subtract. It's very nice to be able to say that when you agree to do something, you're going to subtract something off of your schedule. How often do you really do that? How effectively do you really do that?

Justin Donald: I think it's rare. It's rare for me.

Jonathan Goodman: It's hard.

Justin Donald: I have to be very intentional to do it. And actually, I'm proud of myself because this year I said I want to add some new masterminds, by the way, Mastermind Talks being one of them, but I said there's no way because I was at 14 that I was actively involved in. I don't go to everything. I just pick and choose. All I need is one good event and I can get massive value, right? And I live in the world of one mindset shift, one connection. You know, one strategy can more than cover the mastermind fees or dues, right?

Jonathan Goodman: Oh, God. One connection. One, yeah.

Justin Donald: Totally. Yeah. And so, for me, this year, though, I added a couple. I added two masterminds, Mastermind Talks being one of them, and so I actually did subtract two masterminds. So, I did kind of pull out of a couple.

Jonathan Goodman: So, you did do that. So, I can’t do that naturally. And it really hit me when we bought a house because for a number of years, for the first six or seven years that we did this, call it 8/4 Lifestyle, I owned a backpack and three T-shirts. I mean, really, that’s what we owned. I rented a car and I rented a furnished condo when we got back in Toronto. And when we left, we gave back the keys to both. We put our backpacks on our back and we set off.

When we bought our house in Toronto, I set my backpack down in the corner of the big walk-in closet. I hung my three T-shirts and I said to Alison, “I guess we need to buy a fork.” We owned nothing. You know how much stuff is in that house now? It’s amazing how much you fill space when you have space.

Justin Donald: That’s right.

Jonathan Goodman: And how little you think about that space. And so, what this lifestyle has done, you don’t need to travel, you don’t need to pick up and leave where you live, I won’t stop you, but you don’t need to do that. But this practice of wipe my calendar clean, reassess my priorities, and enter back into my calendar, a we prioritized version of it, based off of what is my focus right now. For example, right now, my focus is books. So, right now, my focus is my career and authorship, which is my next phase of my life. My best hours of the day of the week have to be dedicated towards authorship, has to be dedicated to your priority. And so, that gets put in first.

Justin Donald: That’s right.

Jonathan Goodman: And everything else gets slotted around the edges. And if that means that there are things that I don’t do or things that I don’t do as well, so be it.

Justin Donald: I think that’s a valuable takeaway, a valuable lesson. I love it. Where can we learn more about you and where can we find your new book?

Jonathan Goodman: I’ll answer your question in one go. The book is called The Obvious Choice. It’s Timeless Lessons on Success, Profit, and Finding Your Way. It is for anybody who owns a business. It’s for any market or sales person who works within an existing organization. And it’s published by HarperCollins. So, like, you can get it anywhere. It’s Kindle audio, hardcover, whatever you like, books. Buy the book. I learned a long time ago that books are the best value. I mean, I can see behind you, Justin. You got like 100 books behind you, right?

Justin Donald: I love it. And I actually read mine. So, the ones on this shelf, I’ve read. If they’re not on the shelf, I haven’t read them yet.

Jonathan Goodman: You want to know something? I wasn’t going to talk about this in my little shtick. But you want to know something that I’ve noticed? I decided years ago that any time, any book sounds remotely interesting, I need you to buy it to the point where, when I had an assistant, I kept a note on my phone like an Apple Notes. Anytime I heard about any book, I wrote it a note. And then my assistant just got the note once a month and just blindly ordered every single book to my house.

Justin Donald: That’s awesome.

Jonathan Goodman: And many of those books, I have never read and I might not ever read. But you wonder what the coolest part about it is that I noticed is that those books are on my shelf. I walk by them. I see the spine of the book. And in looking at the spine of the book, sometimes I’m actually reminded of the podcast conversation that I heard. When I heard the posting that I heard about the book, I remember the Facebook post or whatever it was, and I remember the lesson or the thing that that book was going to remind me of. And that actually provides me just that without ever even cracking open the spine of the book, enough value to have more than paid for the book.

Justin Donald: That’s awesome.

Jonathan Goodman: Which I was reflecting on that a little while ago, which is cool. Anyway, the book, buy it. I hope you love it. I’m on Instagram, I’m on Twitter, @itscoachgoodman. Send me a message anytime. Happy to chat. Share this episode there, tag me, I’ll say hi, I’ll say thank you. But the other thing that I’ll say is after you buy the book, if you don’t love the book and you want your money back, just send me a message and I’ll give you back 100% of your money.

Justin Donald: Love it. That’s awesome. Money-back guarantee and all.

Jonathan Goodman: There you go.

Justin Donald: And I’m just going to say, if you love the book or if you think it’s just solid, either way, give a good positive review.

Jonathan Goodman: Oh, yes, Amazon reviews.

Justin Donald: That helps authors big time. Well, Jon, this was awesome. Thanks so much for your time today and for sharing. And I love ending every podcast episode we do with a question that I ask our audience. So, what’s one step that you can take today to move towards financial freedom and living a life that’s on your terms, it’s a life by design, not a life by default? And I really challenge everyone to pick something that Jon taught you today that you learned and implement it ASAP. Thanks so much. And we’ll catch you next week.

Jonathan Goodman: Appreciate you, Justin.