We spoke to Jonathan Goodman in this week's episode of Moneywise. Jon is a bootstrapped eight-figure founder, bestselling author, and the creator of the Online Trainer Academy, the first ever certification for online fitness coaching. He built his $14 million net worth entirely from a one-bedroom apartment in Toronto, never raised a dollar, never sold a company, and he still pays 53% Canadian taxes by choice. At 40 years old, he takes his family of five abroad for six months every year while running his businesses remotely.
Like all Moneywise episodes, Jon breaks down his net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart.
We also went deep on: how he went from a $41/hour personal trainer to a seven-figure business in four years, his contrarian take on staying in Canada despite 53% taxes, why he thinks chasing tax havens is "a rich person's favorite pastime," his Bitcoin strategy as an asymmetric bet, why $7 million was his freedom number, and how he spends $150K/year traveling the world with his family.
Below you'll find my summary of the episode along with the entire transcript.
And by the way...this podcast, the concept of it came from Hampton. Hampton is a private, highly vetted community for high net worth founders started by Sam Parr. Members range from companies doing 3-5 million in revenue all the way up to hundreds of millions. The reason we started this podcast is because there are amazing conversations about money and growing companies that typically happen only behind closed doors, and we thought it would be awesome to share all of this information. If you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.
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Now, below are the notes and the full transcript.
Jon's path to wealth started on a red couch in his parents' basement. He was the senior trainer at his Toronto gym, maxed out at $41.80/hour Canadian, making about $70,000 a year. After pulling a hamstring playing hockey, he couldn't work for two weeks and had a moment of clarity: "Is this what my life is gonna be like?"
Growing up in a Jewish professional family, entrepreneurship wasn't even on his radar. "Every adult that I ever knew growing up was a lawyer, doctor, dentist, teacher, and accountant," he explains. He didn't know entrepreneurship existed as a path.
What changed everything was writing. He started jotting notes on the back of his training clipboard, accumulating 100,000 words over a year. His mom told him, "This might be a book." So he went to the bookstore, looked up bestselling fitness authors, cold emailed them for editor introductions, and self-published "Ignite the Fire" in 2011.
The business evolved quickly: personal blog in 2011, first online course (1K Extra) in 2012 that brought in $300K, then his first seven-figure year in 2013 at just $1.1 million. From 2015 to 2022, he ran a consistent $3-7 million/year business at 35-40% profit margins, all bootstrapped with 100% ownership.
Jon allocates 15% of his portfolio to Bitcoin, which he frames as an asymmetric, mispriced bet. In 2017, he almost put $500K into Bitcoin and Ethereum but backed out. Had he followed through, it would have been worth around $40 million.
He waited until 2020-2021 because the risk profile had shifted. "There are so many millions of people distributed around the world that all buy into the story that it would be almost impossibly difficult for it to not work now," he explains. He bought systematically at a cost basis around $31-32K USD.
His approach is purely long-term. "I've never looked at it as something to trade. If you held me up by gunpoint right now, I wouldn't even be able to give it to you. I'd have to go to multiple safety deposit boxes back in Canada." He sold seven Bitcoin for about $900K Canadian in 2025 to rebalance his portfolio back to that 15% allocation.
Jon extends this expected-value framework to warn against survivorship bias: "The psychology of the type of person who's going to make a decision like putting life savings into Dogecoin is the same psychology of the type of person who's going to make other aggressively stupid bets. When Icarus flies too close to the sun, you don't hear about it when they get burnt. You only hear about it when they win."
Perhaps the most contrarian take in the episode: Jon voluntarily pays 53% Canadian taxes when he could easily relocate. His take is sharp: "A rich person's favorite pastime is to sacrifice their quality of life to get more rich and pay less tax."
He tells the story of a friend who moved his family to Puerto Rico for the 2% tax rate. "He's like, 'It's miserable. The infrastructure is terrible. The schools are not great. We don't know anybody there.' Why there? 'Dude, I can pay like 2% taxes.'"
Jon's logic: once he hit $7 million invested, generating $280K/year at 4%, he was safe. "Knowing that I have more than that, knowing that I've never touched the principal, and continuing to earn more than we spend every single year, the very idea of moving to a place away from family and community just to get richer and avoid tax seemed like a really stupid game to play."
He believes that if you're rich enough to play the tax arbitrage game, you're probably rich enough not to need to.
Jon went through a real estate phase, buying a duplex just before COVID and leveraging it to acquire 13 rental units in Ontario through a JV partnership. He took 105% of his principal out on a refinance and kept scaling.
But he sold 11 of those units. The reason wasn't financial. "Even though it was hands-off with the JV, it still took up our cognitive load. We don't wanna play this game where we're refinancing over and over and over again." He now gets real estate exposure through REITs that own thousands of student houses across Ontario.
His home in Toronto (bought for $1.55M in 2019, now worth ~$3M) accounts for about 12-13% of his total 17% real estate allocation.
For 14 consecutive years, Jon has taken his family abroad for at least four months every winter. This year it's Japan. Last year it was Mexico. Before that, Bali. The family of five (plus his mother-in-law) runs like clockwork.
The breakdown: $11K/month for school through a program called Boundless Life, $6K/month for a three-bedroom rental, $25K for flights and vehicles over six months, and about $25K for sightseeing. Total additional cost beyond their Toronto baseline: roughly $150K/year.
His kids are part of the conversation. When they asked their oldest if he wanted to do a longer trip, he said, "Yeah, Daddy, I'd love to, but I wanna be in school. I don't wanna be homeschooled." Jon respects that. If the kids push back, they'll adjust.
The philosophy extends to how they think about their home. When they're abroad, friends stay in their Toronto house for free. "A home is a home. It's special. It is memories. I can make money in other places."
Jon draws a sharp distinction between your job (what you do for money) and your work (what you do for you). "Once you've made enough money in your job, it's important to stop that goal line from moving. When it comes to your work, you should never stop that goal line from moving."
He recently onboarded a five-person content team for $13K/month that lets him delete social media from his phone while still maintaining his presence. He gets one email per week on Thursday morning with everything to review. "I buy in that this stuff is important. But I don't accept that it's something that needs to diminish my quality of life or ability to focus or presence with people I love."
His biggest career lesson came from launching 32 different products over the years. "Society forgives failure, and really only one thing has to work." Of those 32, he describes "a whole bunch of bloop singles, a few legged out doubles, some strikeouts, and two home runs." The two home runs (1K Extra and Online Trainer Academy) generated $30-35 million.
His goal now: "I wanna be able to disappear for a month and have no one notice." Not because he wants to disappear, but because "the only thing that I think you can expect with any degree of expectancy in this life is that at one point the unexpected is gonna come and kick you in the teeth."
"A rich person's favorite pastime is to sacrifice their quality of life to get more rich and pay less tax."
"I call it walking costs. You've gotta keep your walking costs low. That's freedom."
"If you're at the point where you are rich enough to be able to play this game, you're probably at the point to not have to play this game."
"Society forgives failure, and really only one thing has to work."
"Your job is what you do for money. Your work is what you do for you."
"I can listen and read an unlimited amount of books about books, about writing, about how other authors live. I owned a B2B SaaS platform called QuickCoach. I couldn't even make it through a five-minute YouTube video on SaaS."
"The best experiences to me don't cost much money. The part that costs money, especially when you have young children, are things like babysitting, childcare."
"I keep my cup half full, because at one point something's gonna come and you're gonna be really happy that you have that extra space."
Daniel Berk: In 2009, Jonathan Goodman was a broke personal trainer living in Toronto making only $41 an hour. He started the blog, self-published a book by 24, and by 2013 he had his first seven-figure year. Today, he's done over $35 million in revenue, built a $14 million net worth, never raised a dollar, never sold a company, and takes his family abroad for six months out of the year, all while paying 50% on his income to his Canadian taxes by choice. This is the story of a guy who found his number and stopped chasing. Moneywise is a Hampton podcast. Hampton's a private community for founders doing two million or more in revenue. There's real conversations that happen in the Hampton community behind closed doors that you really just can't get anywhere else, especially if you're a wealthy founder. If you're looking for a community like this, go to joinhampton.com. Now, Jon Goodman on Moneywise. Welcome back to another episode of Moneywise. Today, we have Jonathan Goodman on the show. Thanks so much for joining us today, Jon.
Jonathan Goodman: Yeah. What a joy, man. I'm looking forward to this.
Daniel Berk: Me too. Me too. Uh, I wanted to just start off with your family growing up. You grew up youngest of four in a Jewish professional family. Sounds like there were doctors and, and lawyers and accountants. Uh, what was money like in your house growing up?
Jonathan Goodman: I mean, money... We were, like, middle to upper class, so we'd go out for dinner once a month at the Pickle Barrel. We had our timeshare in Orlando. But beyond that, yeah, if something was on sale, we, like, stocked up. There were four hungry kids. My parents never made a lot of money, but they made enough, and they were very smart with it. And although I was never really taught, like, explicitly about money growing up, through osmosis I could see what they were doing, and I think that that kind of watered down and, and, and helped me a lot now.
Daniel Berk: That's great. And when you started this personal training program in your 20s, you've-
Jonathan Goodman: Yeah
Daniel Berk: ... vocalized even on X and, and elsewhere on the internet you were a broke personal trainer. What did-
Jonathan Goodman: Right
Daniel Berk: ... a broke personal trainer look like? What, what did that actually mean?
Jonathan Goodman: All personal trainers. It's interesting 'cause I was about as successful as a personal trainer as you'd get in Toronto at that time. I... 30 client hours a week. I was the senior trainer at my club. I was referring my overload of clients to other trainers, but I mean, I was making $41.80 an hour.
Daniel Berk: Okay. That was what I was taking home. That wasn't what I was charging out at.
Jonathan Goodman: That was Canadian dollars or USD?
Daniel Berk: It's Canadian dollars.
Jonathan Goodman: Okay.
Daniel Berk: And I was getting a monthly salary for being a senior trainer, so I was making about $70,000 a year, right?
Jonathan Goodman: Okay.
Daniel Berk: Which is actually, like, a pretty good salary as a personal trainer. The problem is I was kind of at the cap.
Jonathan Goodman: Yeah.
Daniel Berk: In that industry, there's only so much you can grow unless you wanna own a gym or become a business owner, whatever. And so I, I reached this point, I call it my red couch moment, 'cause I was living in my parents' basement, and I was sitting on their red couch. And I looked up, and I was working, like, 12-hour days, and I had just pulled a hamstring playing hockey at night.
Jonathan Goodman: Oh, jeez.
Daniel Berk: And so I was off my feet for two weeks, which means I couldn't work for two weeks, and all that I could think about was, "Is this what my life is gonna be like?"
Jonathan Goodman: Hmm.
Daniel Berk: I know that I wanna have kids at one point. I know that I'm probably gonna get sick at one point. Like-
Jonathan Goodman: Yep
Daniel Berk: ... if I can't be in this career where I'm not going to be able to work, even if the money is, you know, good enough for now. And then, of course, there's the cap of the growth, which was an even bigger issue.
Jonathan Goodman: Okay. And the cap of the growth, is that what started you down this journey of, uh, of realizing you could actually make more?
Daniel Berk: Oh, God. Um, I don't know what started me down this journey, to be honest.
Jonathan Goodman: Every adult that I ever knew growing up was a lawyer, doctor, dentist, teacher, and accountant. Like, my dad's an engineer. My mom's a teacher. My sister's a lawyer. My brother's a small business banker. My other brother is a high school math teacher.
Daniel Berk: So you were around a lot of-
Jonathan Goodman: And so-
Daniel Berk: ... ambitious people.
Jonathan Goodman: I was around a lot of very smart, very intelligent people who had their lives more or less set in front of them.
Daniel Berk: Mm-hmm.
Jonathan Goodman: Like, like, they knew, and how I grew up was adults knew that they were making X amount of dollars this year. In five years, if they do a good job, they're gonna make Y amount of dollars. In 10 years-
Daniel Berk: Mm-hmm
Jonathan Goodman: ... they're gonna be at Z amount of dollars. And so they could very much plan for that, and if they save for that and if they assume a percentage of growth, I mean, this is kind of what I understood through osmosis growing up. Entrepreneurship wasn't a thing.
Daniel Berk: Okay.
Jonathan Goodman: So I never even considered it, to answer your question. I didn't even know that it existed, really, growing up, if I think back. It was just, I call it optimistic ignorance. I just kind of... I was personal training on the floor. I wrote down what I was doing on the back of my clipboard, or if I struggled with something or if I was asked a question by a client or if I had a crush on a secretary or if I saw another trainer instructing an exercise wrong, I wrote it on the back of my clipboard. And I went home at night. I thought about how I might be able to deal with that better. Call a friend, I'd say, "How would you deal with this?" And I wrote that down. It was personal development. And after about a year, I had 100,000 words written, and I showed it to my mom, and my mom said, "This is really interesting. You've got something there. I think this might be a book." I don't know anybody who's written a book. How do you figure out how to make a book? This is 2009. How do you figure out how to self-publish a book for an industry? I was 23 years old. And so I didn't know. You know, looking back, I didn't know what all the steps were, but I knew what the next step was, which was I knew where books existed.
Daniel Berk: Mm-hmm.
Jonathan Goodman: Books existed in the bookstore.
Daniel Berk: Mm-hmm.
Jonathan Goodman: So I went to the bookstore. I looked up the names of the bestselling fitness books. I found the authors. I cold emailed them and asked them for an introduction to their editor.
Daniel Berk: Wow.
Jonathan Goodman: And one thing led to the next. I self-published a book. I started a website, realized other people were writing interesting things on the internet, but they suck at headlines, and they suck at images, and they suck at contextual editing and promotion and distribution of their work. Why don't I just get permission and pay them to republish their work on my website? And that's how it started.
Daniel Berk: So when did this, what year did-... this start to really make money, when the business changed from $70,000 being a personal trainer to-
Jonathan Goodman: Yeah
Daniel Berk: ... oh, actually, there's, there's a real business opportunity here, and I should invest heavily and aggressively in, in growing this thing?
Jonathan Goodman: So Ignite the Fire, the book that I self-published, came out in 2011.
Daniel Berk: Okay.
Jonathan Goodman: The website, the Personal Trainer Development Center, launched in 2011. It was my personal blog basically. I called it Personal Trainer Development Center, and no shit, we put a building in the logo so that it looked more important than a 24-year-old kid
Daniel Berk: Nice
Jonathan Goodman: ... writing this from his one-bedroom apartment after a full day training clients. So 2011 was kinda like my personal blog. 2012 was when it started kinda doing it. I, I hosted, like, a seminar in a gym in 2011. I messed around with a little bit of affiliate promotions, but 2012 would've been the first year where I put out a course called 1K Extra at the time.
Daniel Berk: Okay.
Jonathan Goodman: Which was the first ever educational program that taught trainers how to train a client online. Very cool. And I put that out in 2012. 2012, I made about 300,000.
Daniel Berk: Okay. From the PTDC. And so from 2009, 2009, sorry, to 2012, you went from 70,000 up to 300,000.
Daniel Berk: Was that a steady growth?
Jonathan Goodman: Nah, it was, it was, like, 70, 75,000 in the gym. Maybe I did, like, 100 and 120 in 2011. I don't actually really remember.
Daniel Berk: Yeah.
Jonathan Goodman: I was investing a lot into the webs- Like, websites cost, like, 8 to 10 grand because-
Daniel Berk: Yeah ... you had to get somebody to code them at the time.
Jonathan Goodman: Yeah, yeah. I, I mean, I self-taught myself Photoshop on YouTube. Like, HTML, the same thing. It, it was way-
Daniel Berk: Yeah ... harder that back then.
Jonathan Goodman: Sure. Which meant that there was a, um, a costly signaling involved for people-
Daniel Berk: Mm-hmm ... publishing content online because of the cost.
Jonathan Goodman: So I spent a lot is the, is the-
Daniel Berk: Yeah ... story.
Jonathan Goodman: Sure. By, um... And then it, and then it jumped in 2012.
Daniel Berk: Yeah. Yeah. And I'd love to start unpacking that. I mean, you've described yourself since then as an eight-figure founder. I'd love for you to start to kinda walk us through from-
Jonathan Goodman: Mm ... $300,000 in 2012 until now.
Daniel Berk: What did that growth look like year by year? Yeah. Even if you can, you know, you can be high level, but year by year if you have that available. And what is the actual revenue across some of these different, you mentioned PTDC, right? Is that the acronym? The Trainer Academy.
Jonathan Goodman: The worst name. Not, not the Pakistani Tourism Development Center.
Daniel Berk: Okay.
Jonathan Goodman: It's the Personal Trainer Development Center.
Daniel Berk: Yeah, not to be confused.
Jonathan Goodman: Exactly. Personal, Personal Training Development Center, Online Trainer Academy.
Daniel Berk: Yeah. Your books. Uh, you know, walk us through kinda where you're at now with that revenue and, and what that looks like across all those business assets.
Jonathan Goodman: So 2012, I realized I had something. I cut back my clients to 25 clients a week and 15 hours a week. I kinda categorized them as, like, gold, silver, bronze. You know, I kept my gold. I arranged my schedule around them. All of the silver ones, I said, "You know, if you can fit in these extra blocks, great," and the bronze I gave away. By 2013, I stepped away from training clients full time to work on the website 'cause I was like, "I got a shot here," right? Like, I can always go back.
Daniel Berk: How much were you making when you stepped away?
Jonathan Goodman: It would've been about three... I mean, that was, it was early 2013.
Daniel Berk: Okay.
Jonathan Goodman: So, uh, about that 300,000.
Daniel Berk: Okay, okay.
Jonathan Goodman: Right. And that was also the first winter that I did abroad, and so that was the first now of 14 consecutive winters where I've traveled a minimum of four months, which I'm sure we'll get into. 2013 would've been the first seven-figure year. So 2013, I had done a couple other kind of online products. We built the first ever informational product for Facebook ads for fitness professionals. I did a postnatal one. We did all the stuff. I hosted conferences, but this online training thing kind of stuck, right?
Daniel Berk: Cool.
Jonathan Goodman: And so I, I started speaking about that. I started writing about that. I started doing all the SEO on that. And, um, 2013, 1K Extra would've led to just over a million a year. I think we did, like, 1.1. And then, yeah, I mean, look, 2015 to basically 2022, we did pretty consistently, like, 3 to 5 to 7 million a year. There was never a year that was spiked.
Daniel Berk: Yeah.
Jonathan Goodman: It was just this very consistent 35, 40% profitable, 4 million, $5 million a year.
Daniel Berk: 40% profitable, is that 40% in your pocket each year, or did you-
Jonathan Goodman: Yeah ... have...
Daniel Berk: Yeah. So 40% of the, let's call it 7 million, was paid to you, uh, for eight years in a row?
Jonathan Goodman: Yeah. I've always, I bootstrapped everything. I always owned 100%. I paid people really well, but I always owned 100% of everything that I did. I've never taken investment. Out of all of the businesses, we did 32 different products over those years. Right. That's how much stuff that I tried. And probably the biggest lesson that I realized is that society forgives failure, and really only one thing has to work. So I say of that, of those 32 products, a whole bunch of bloop singles, a few legged out doubles, some strikeouts, and two home runs. And so, you know, PTDC was always the parent company. It never did its own thing.
Jonathan Goodman: It always just had all of these business assets underneath it, from courses to I did a paid print newsletter, to membership sites. If you think about online marketing, I've tried it. But the biggest thing was 1K Extra. In 2016, we evolved into the Online Trainer Academy.
Daniel Berk: Okay.
Jonathan Goodman: Which was called OTA, which was the first ever certification for online fitness. Wrote the textbook, created the first ever certification. Self-published it. Nobody needs to give you permission. You know, you can just do things, right?
Daniel Berk: Yep.
Jonathan Goodman: And OTA, over those years, did 30 to 35 million in revenue. Between OTA and, and 1K Extra from 2013 to 2024, when it was finally shut down, did $30 to $35 million in revenue as an online course. So that was, that was the main thing for sure.
Daniel Berk: And those two things combined, uh, with some of the other ventures, where does that leave your total net worth now, both liquid and, and assets and illiquid funds and monies?
Jonathan Goodman: Total net worth is just over 14 million
Daniel Berk: So 14 million. Walk me through where that money is currently invested, uh, and/or just in cash. It's in a lot of fun things that we'll get to with the way you travel, and I'd love to, you know-
Jonathan Goodman: Right
Daniel Berk: ... divulge that a little bit here in a minute. But walk me through your actual personal spending. What does it look like in a given year, a given month? Where does that money actually go nowadays?
Jonathan Goodman: In terms of investments, it's, it's, it's basically all liquid. The only one that's not liquid is a, is a 2% kind of fund super precede investment I did in this baseball card company, 'cause I love baseball cards. That's actually going really well.
Daniel Berk: Great.
Jonathan Goodman: But, I mean, that... Beyond that, I mean, we're at about... I mean, I could give you the... where all of this goes within each, but it's about 17% real estate, 15% Bitcoin, 65% equities, which includes some REITs, so the real estate holdings are actually a little bit bigger, but the REITs. And then, you know, my other investment pillar is about 3% into my network and reputation.
Daniel Berk: Cool.
Jonathan Goodman: And the, the reason for those allotments is I take into account asymmetric investment opportunities, mispriced bets. And so-
Daniel Berk: Explain what that means.
Jonathan Goodman: Right. So I think that if you search for long enough, you can find the rare opportunity where if it works, it has an outsized impact for the amount that you invest. And if it doesn't work, you don't invest that much that it's gonna really affect you. And so if something can work one out of 100 times and pay for the 99 losses, it's probably a good bet to make. We can get into expected value equations if you want, for all my poker bros out there, but it's, it's basically if you have a wildly positive expected value, then the bet makes sense to make-
Daniel Berk: Sure
Jonathan Goodman: ... even if it's a far-fetched bet. You can expect it not to work because in the rare case that it does, it's gonna work with an outsized impact. And so I look at investments into Bitcoin and then my network and reputation both as asymmetric mispriced bets. And so my investment allotment in those is lower because I don't need as much actually invested into them because if they win, they're gonna win so big.
Daniel Berk: Mm.
Jonathan Goodman: So I don't need to do, I don't need to put as much risk into them.
Daniel Berk: Jon, it looks like you've invested quite a bit in Bitcoin. Walk me through some of your thinking around putting any money in Bitcoin.
Jonathan Goodman: I'm always looking for, uh, mispriced bets or asymmetric opportunities. And what's interesting about Bitcoin is that in 2017, I actually had half a million dollars that I was gonna put into half Bitcoin, half Ethereum. I had, like, the devices, like, the ledger devices to put them on and everything, and I didn't end up doing it, and I sold the devices. And if I did that, I'd have, like, yeah, $40 million or something stupid.
Daniel Berk: Everybody's got a story like that with crypto, right?
Jonathan Goodman: Yeah.
Daniel Berk: I, I have one too. But-
Jonathan Goodman: Yeah.
Daniel Berk: It's, uh, it's rough ... everybody's got one like that.
Jonathan Goodman: Yeah.
Jonathan Goodman: But in basically from the end of 2020 all throughout 2021, I put systematically 15% of my company's investment into Bitcoin. Not anything else, just Bitcoin. And I also maxed out my TFSA. So in Canada, we have a tax-free savings account. Basically, we get $5,000 a year that adds up, and whatever money you make in that account is tax-free. You can, you can take it out whenever you want. So it's a great place to, like, make a big bet in because if you, if it, if it grows a ton, you get that money tax-free.
Daniel Berk: Yep. I probably was one of the first, if not the first Canadian, to max out my TFSA in something called QBTC. If you're not Canadian, the TFSA, which is a tax-free savings account, is basically Canada's version of a Roth IRA in the United States. You contribute after-tax money, it grows completely tax-free, and when you take it out, you owe nothing. So what Jon did was take the money from his tax-free savings account, which is he started contributing the $7,000 max in 2009, probably was around $95,000, maybe a little bit more, and he put all that into Bitcoin when it was around $30,000. So at that point, if it went to zero, it was a real loss, but it was somewhat contained. And Jon, which he's about to get into, really thinks Bitcoin's gonna do super well. Uh, and so it was essentially a legal tax-sheltered lottery ticket, and now this is what happened.
Jonathan Goodman: Which was the first ever fund that allowed you to invest in exposure to Bitcoin in a registered investment fund. This was before the ETFs or anything were-
Daniel Berk: Wow
Jonathan Goodman: ... like, like, a couple years before they were available in the United States. And I still, I haven't touched it, right?
Daniel Berk: Good for you. What, what was the cost-
Jonathan Goodman: And the reason-
Daniel Berk: ... of Bitcoin at that, at that point, and how much did you put in?
Jonathan Goodman: I mean, it, it, it went up and down. Sure. Right? But my co- my cost base was, like, 31, 32,000 US.
Daniel Berk: Good for you. How much did you put in?
Jonathan Goodman: I won't say that. You don't, you don't, you don't tell people how much Bitcoin you have.
Daniel Berk: Okay. Fair enough. Um-
Jonathan Goodman: I'm curious. I, not, not a, not a crazy amount.
Daniel Berk: Give, give, give me a range. Hu- uh, million dollars.
Jonathan Goodman: Well, I'll tell you this. I sold... Last year in 2025, I sold for the first time ever, and I sold seven Bitcoin for about 900,000 Canadian, and that was to rebalance the portfolio at 15% allotment-
Daniel Berk: Okay
Jonathan Goodman: ... in Bitcoin.
Daniel Berk: So you, you put in, you put in well over seven figures.
Jonathan Goodman: Yeah. Yeah, yeah, yeah.
Daniel Berk: Okay.
Jonathan Goodman: Yeah, over years.
Daniel Berk: Got it.
Jonathan Goodman: But I did it, I did it, like, systematically, right?
Daniel Berk: Sure.
Jonathan Goodman: So small buys of-
Daniel Berk: Yeah
Jonathan Goodman: ... some bigger buys, but mostly, mostly smaller buys. But the reason for that is, and why I waited until 2020, 2021 and not 2017, is it seemed like there was this very unique time where if this thing works, it's gonna work really big-
Daniel Berk: Mm-hmm
Jonathan Goodman: ... or it's not gonna work at all.
Daniel Berk: Mm-hmm.
Jonathan Goodman: Like, like, I don't really think there's much in between. And when you study money and finance as much as I have, you pretty quickly come to the appreciation that money is a story that we all buy into. The only reason that money works, the only reason the financial system works, is because we've all agreed that this piece of paper is worth this many grains of rice.
Daniel Berk: Yep.
Jonathan Goodman: Like, that's, that's, that's kind of it. That's the reason why money works in Canada and the United States. That's the reason why money doesn't work in Nicaragua, because the government in Nicaragua basically says, "Screw you, rest of the world. Here's what our money's worth."
Daniel Berk: Yeah. Yeah.
Jonathan Goodman: And so it doesn't work there, right? What I felt was true at the end of 2020 into 2021 and continues to be true now-
Daniel Berk: About Bitcoin
Jonathan Goodman: is that there are so many millions of people distributed around the world that all buy into the story that it would be almost impossibly difficult for it to not work now.
Daniel Berk: Yeah.
Jonathan Goodman: And so it seemed like the odds of it not working and going to zero in 2017 were too big for me. They were still pretty small, but they were too big for me.
Jonathan Goodman: The odds of it going to zero now with so many stakeholders seems pretty small, and if it does win, it's not just gonna win by a little bit.
Daniel Berk: Yeah.
Jonathan Goodman: And so I've never looked at it as something to trade. Doesn't matter what happens in the short term. It's like if I wanted to sell it or if you held me up by gunpoint right now, I wouldn't even be able to give it to you. I'd have to go to multiple safety deposit boxes back in Canada. It's just, it's just locked away.
Daniel Berk: Very cool. I had a ledger, have a ledger. I just, uh, I just put my hands on it a few days ago, and I was trying to buy Dogecoin-
Jonathan Goodman: Okay ...
Daniel Berk: at .0002 cents-
Jonathan Goodman: Right. Okay ...
Daniel Berk: on Kraken when Kraken... This was in 2020, early 2020, late 2019-
Jonathan Goodman: Right ...
Daniel Berk: when no one knew what Dogecoin was.
Jonathan Goodman: Right.
Daniel Berk: The long of the short is I would've made about $10 million if it would have let me-
Jonathan Goodman: Right ...
Daniel Berk: buy it.
Jonathan Goodman: Right.
Daniel Berk: But the, it wasn't working. The whole system was crashing because me and every other rando that was up at 2:45 AM and had discovered Dogecoin was trying to buy it. So anyways, we all have a story like that.
Jonathan Goodman: But here's my, here's my, here's my opinion about that, is that if you did buy it, that would've been a dumb shit decision.
Daniel Berk: Oh, so idiotic. I mean, in hindsight it's like, oh, this is what could have happened, and I would've netted blah, blah, blah. But yes, it was, it was an idiotic decision for me to have been-
Jonathan Goodman: That dumb shit decision would... This is why I think percentages and expected value is so important because even if you make the best dec- the best investors in the world are only right 60 to 62% of the time with the best information, the best everything. Invert that, they're wrong four out of 10 times.
Daniel Berk: Mm-hmm.
Jonathan Goodman: Now, if you make the dumbest decision ever, which I would probably define putting your life savings into Dogecoin, like, in that bucket.
Daniel Berk: Yeah. Oh, for sure.
Jonathan Goodman: You probably had a 98% chance of failure, but there was a 2% chance of success, and that roulette wheel hit for some people.
Daniel Berk: Yes.
Jonathan Goodman: Now, the psychology of the type of person who's going to make a decision like that is the same psychology of the type of person who's going to make other aggressively stupid bets.
Daniel Berk: Oh, yeah. The difference is-
Jonathan Goodman: You're talking, you're talking to one of those guys right now, aggressively stupid.
Daniel Berk: Sure.
Jonathan Goodman: The difference is that when Icarus flies too close to the sun, you don't hear about it when they get burnt. That's right. You only hear about it when they win. I mean, this is the same for people who chase social media trends if they're trying to market. Yeah. It's no different. We, though, as an onlooker, the problem is we only compare ourselves to a representative assortment of people. We don't compare ourself to one person, and we follow them for a long enough period of time to see the ups and the inevitable downs. Instead, we compare ourselves to a representative group of people, and at any one point there's always gonna be one person winning, doing something that objectively is probably a really bad decision. We don't see that same person making multiple bad decisions and them not working out for that person two years in the future, 'cause we've moved on to the next person, and the next person, and the next person.
Daniel Berk: I mean, look, yeah, sure, buddy told me about Solana at the same time. I'd have $180 million if I bought Solana with the amount of money I bought Bitcoin with.
Jonathan Goodman: You can, you can always, you can always look back and what, what if, you know...
Daniel Berk: Yeah, what if I had the winning lottery number, you know? It's, it's a lotta, a lot of things-
Jonathan Goodman: Right ...
Daniel Berk: you can't control that are stupid decisions that a few people made a lot of money from.
Jonathan Goodman: Yeah.
Daniel Berk: No, that's, that's great. Real quick, today's episode is sponsored by Oceans Talent. If you're trying to hire a great EA or ops person right now, you're looking at 80 to $100,000, sometimes more, and I know a lot of founders have tried to go the remote route before and gotten burned.
Daniel Berk: Sometimes they get ghosted, the work's sloppy, you end up redoing everything yourself. I've heard the stories before, and I've even personally lived them. Oceans Talent is completely different. They pre-vet every single candidate with thorough skills assessments, so whoever they match you with is ready to go on day one. And it's not just EAs. They do marketing ops, finance, HR, sales, even AI workflows. I've hired people personally through Oceans Talent, and I'm blown away by the quality of work they produce. Sam Parr has his personal assistant through Oceans, and he describes her like this: "She runs my life. I couldn't live without her. I have total trust in her, and I don't trust anyone." That's the bar they set. So if you're a founder drowning in stuff a great hire should be handling, check out Oceans Talent at oceanstalent.com/moneywise. That's oceanstalent.com/moneywise. I'd love to know more about the real estate. You mentioned 17% is in real estate. What does that actually mean to have 17% in real estate?
Jonathan Goodman: So that is our home in Toronto, where homes cost a lot of money.
Daniel Berk: Sure.
Jonathan Goodman: And we did actually do a fair amount of residential real estate investing. A number of years back, bought one unit, converted it into a, a, a legal duplex. We financed that eight months later because this is just before COVID, and then into COVID. We got lucky. We financed that, uh, about eight months later and took 105% of our principal out. And then we ended up buying 11 more units in the next year. So at one point we owned 13 different, basically rental units in Ontario.
Daniel Berk: Okay.
Jonathan Goodman: We have since... And that was all with the JV. The JV got 50% of the upside. They managed everything start to finish. It was completely hands-off on our end. We put up the cash. They did everything else, right?
Daniel Berk: Right.
Jonathan Goodman: And, um, we actually have since sold 11 of those units. We only own, we only own that original duplex actually still. And we made s- we made a bunch of money on them, but what we realized was that even though it was hands-off with the JV, it still took up our cognitive load. It still took up our time. We don't wanna play this game where we're refinancing over and over and over again, getting more and more properties. You know, it's just more problems. And so we decided, along with our advisor, to sell those, and we can still have exposure to real estate. Like, we have a big holding in a REIT that owns thousands of student houses across Ontario-
Daniel Berk: Interesting ... for example.
Jonathan Goodman: Interesting. So we still have exposure to real estate at about the same percentage allotment. It's just not in our single family homes anymore. Yeah. It's more within REITs and, and, and, and equities because then it's just in the same bucket. It's, it's easier for us.
Daniel Berk: Yeah. Some people might say 17% in real estate is kinda risky. Is, is... I mean, is there a, is there a reason you put that much in real estate from the total net worth, or did you kinda fall into that?
Jonathan Goodman: The honest truth is that such a high percentage of it is our personal home.
Daniel Berk: Yeah. That's-
Jonathan Goodman: That's the only reason why it's so high ... that's a good point.
Daniel Berk: What percent is the personal home?
Jonathan Goodman: Yeah, the reason. We have, we have our personal home. We own, we, we bought my wife's family cottage-
Daniel Berk: Okay ... from her brothers and renovated it. And so the percentage of that in the family cottage probably-
Daniel Berk: How much did your home cost?
Jonathan Goodman: ... of the 17% is, like, 12, 13%. Okay. I mean, our home, I mean, Toronto real estate is just nuts, right? Like, we bought our home for 1.55 million in 2019. It's probably worth close to three now.
Daniel Berk: I wonder why you stayed in Canada. You had a business there. The taxes are through the roof, and, uh, you didn't leave-
Jonathan Goodman: Right ... when you obviously could have.
Daniel Berk: What, uh, what made you stay?
Jonathan Goodman: A rich person's favorite pastime, you know what that is?
Daniel Berk: You tell me.
Jonathan Goodman: It's to sacrifice their quality of life to get more rich and pay less tax. Okay, so a little additional context on this.
Daniel Berk: In Canada, where John lives, the combined federal and provincial tax rate tops out at 53.5%. That means for every dollar John earns above a certain income threshold, he keeps less than 50 cents. Compare that to Florida or Texas, zero state income tax. The federal bill's the same, but there's nothing on top of it. That's why so many wealthy founders play what John's calling the tax game. They move to Puerto Rico, Dubai, the Cayman Islands, or just across the US border to a no income tax state. In Puerto Rico specifically, there's an incentive called Act 60 that caps your investment income tax at 4%. So you can see why John's friends are making this move. But what John is actually saying, and he's about to get into this, is he's already done the math. There's a certain point where you're so wealthy that it just becomes a game. If you're not gonna pay the taxes in this place, you're gonna pay the taxes somewhere. And if the taxes aren't taxes themselves, you're gonna get taxed somewhere in your life. Here's what John has to say about that.
Jonathan Goodman: Ooh, I'm gonna remember that one. That's a rich person's favorite pastime. Yeah. You're right. I could evis- easily have gone to a... I could've basically, like, not shut down the Canadian corporation. Like, all my companies are in Ontario. Yeah. I could have just, you know, started shuttling money to an overseas account, right? Set up a new business, whatever. Look, I love Canada. I really do. I also think it's the responsibility of the young people who have the ability to own to support the people who don't and the older generations. I think that-
Daniel Berk: Yeah ... that's important.
Jonathan Goodman: I take a lot of pride in that. I also know that I have enough. I knew that once I had $7 million invested, I was safe. That's $280,000 a year.
Daniel Berk: What John just described is called the 4% rule, and it's one of the most well-known concepts in personal finance. The idea is simple. If you have a diversified investment portfolio and you only ever withdraw 4% of it per year, historical data shows your money will last at least 30 years, no matter what the market does. The rule was invented by a financial advisor named William Bengen back in 1994. He ran the numbers on every 30-year stretch of market returns going back to 1926 and found that 4% was the magic number. It was low enough that even the worst consequences of market returns wouldn't wipe you out. So at $7 million, 4% is exactly $280,000 a year. Just like John said, that number, 25 times your annual spending, is your freedom number. It's the point where mathematically you never have to work again if you don't want to. John hit it, and what he decided to do with that, that's the interesting part, and he's about to get into it. Yeah, I was gonna say- It was enough ... is that the number then? Do, you didn't, you didn't really want more after seven?
Jonathan Goodman: Not that I didn't want more. Of course I want more. You never don't want more. But I knew that I didn't need more. I knew that I was safe. I call it walking costs.
Daniel Berk: Yeah.
Jonathan Goodman: You've gotta keep your walking costs low. That's freedom.
Daniel Berk: Yeah.
Jonathan Goodman: You might join the bougie health club. You might go on the expensive vacations. But you don't ever let yourself get stuck by those things. And so-
Daniel Berk: Yeah ...
Jonathan Goodman: I knew that once I had $7 million in the bank account and a home, that's gonna kick off $280,000 at a, at a very reasonable 4% interest rate without touching the principal. Yeah. Knowing that I have more than that, knowing that I've never touched the principal, and continuing to earn more than we spend every single year, the very idea of moving to a place away from family and community just to get richer and avoid tax seemed like a really stupid game to play. There's somebody who I met recently, he's from the States, moved his family to Puerto Rico, and we were asking him about how living in Puerto Rico is. He's like, "It's miserable."
Daniel Berk: Mm.
Jonathan Goodman: He's like, "We don't like it. The infrastructure is terrible. The schools are not great."
Jonathan Goodman: We don't know anybody there." "Why there?" "Dude, I can pay, like, 2% taxes." Yeah. So just to get... If, if you're at the point where you are rich enough to be able to play this game-
Daniel Berk: Yeah
Jonathan Goodman: ... you're probably at the point to not have to play this game. Look, my goal is to not stop working. I think work is wonderful
Daniel Berk: Mm-hmm
Jonathan Goodman: And so I live a six minute and forty nine second walk from my parents. Nice. An eight minute walk from my sister who's in Toronto. Dude, it's, it's, it's bliss.
Daniel Berk: I resonate a lot with that. So yeah. Yeah. I, I live in Charleston. My family was in Seattle and Wisconsin and Boston, and after enough times of telling them all to move to Charleston, all of them-
Jonathan Goodman: Yeah
Daniel Berk: ... except my poker playing brother in Vegas moved to Charleston. So now-
Jonathan Goodman: Yeah
Daniel Berk: I'm a 10 minute drive from my parents in one direction and a 10 minute drive from my brother and his wife and their kids in the other direction. And all the cousins get to grow up together. I mean, there's really, to me, there's nothing more valuable than that in the grand scheme of things. And so I, I certainly-
Jonathan Goodman: Yeah
Daniel Berk: ... resonate with some of those thoughts.
Jonathan Goodman: I mean, Ontario has exceptionally high taxes. It's very employee friendly, so it's very difficult to run a small business there and expensive. Yeah. And the cost of living is really high. But what I've realized over my years of spending a minimum of four months a year abroad, a lot of the time around people who have made this decision. Yeah. I've realized, Daniel, that everybody pays the same taxes, but they just pay it in different ways.
Daniel Berk: Tell us more about the, the winters abroad. You started in 2013, you said? So-
Jonathan Goodman: Yeah
Daniel Berk: ... and you've done that every year for the last 11 years? Mm. Or I guess that would be 13 years. So where are the places you've gone, if you can list them off really quick and-
Jonathan Goodman: Oh, God
Daniel Berk: ... tell us why you've built your life in this way, because I think this is, this is incredibly unique to-
Jonathan Goodman: Right
Daniel Berk: ... take your wife and your kids-
Jonathan Goodman: Yeah
Daniel Berk: ... to another country every winter for, you know, three, four months out of the year. And I'd love to hear more about why you do that. And then also I'd love to get into the personal spending, 'cause I think the first part-
Jonathan Goodman: True
Daniel Berk: ... of the story is interesting. You know, personal spending, very cool. This is where I spend my money. But the, the abroad portion, I think that's actually where-
Jonathan Goodman: Yeah
Daniel Berk: ... your personal spending may get a little bit more unique, given different currencies, different lifestyles, different renting patterns. So tell me a little bit about that.
Jonathan Goodman: Yeah, I mean, I can, I can break down the, um, like our monthly spend, and we'll do this after. I'll break down my monthly spend when we're at home, and then our monthly spend when we're abroad as well. For context, I've been with my wife for 15 years. This year will be our 10th wedding anniversary.
Daniel Berk: Congrats.
Jonathan Goodman: Our kids are 8, 4 and 11 months. So I started doing this by myself, then my girlfriend started coming, then we were engaged. All of our pregnancies, you know, she's done checkups all around the world, and one of them, one of our pregnancies, she actually had cancer at the same time, so she was doing checkups-
Daniel Berk: Okay
Jonathan Goodman: ... and she was doing scans for cancer at the same time-
Daniel Berk: Mm
Jonathan Goodman: ... while we were abroad. So, you know, every year it's just been, "Hey, can we do this another year?" It's not, "This is our lifestyle forever." It's just like, "Can we do this again?" "Yeah, sure. Why not?" Where have we been? Oh, that'll... I'm sure I'll forget some places. Yeah. Hawaii twice, Costa Rica twice, Dominican, Nicaragua, Mexico five times. There's this little town called Sayulita. Greece on Crete. We were in Kotor in Montenegro, Uruguay. We are currently in Kamakura, Japan for three months. We were just in Bali and Indonesia. We did Koh Phangan in Thailand twice.
Daniel Berk: Do you have someone that plans this for you? Or do you do all this yourself logistically?
Jonathan Goodman: We plan it, but I love constraints.
Daniel Berk: Okay.
Jonathan Goodman: So I always look for constraints. Okay. For example, like I don't like connecting flights, so how did we decide to go to Abu Dhabi for four days before arriving in Bali? It's like, okay, where can we fly from Toronto that flies direct, that also flies direct to Bali? Abu Dhabi. That also in December is warm enough that we don't have to bring jackets because we're gonna be in Japan in the spring-
Daniel Berk: In Bali ...
Jonathan Goodman: and then Bali and-
Daniel Berk: Yeah ...
Jonathan Goodman: you know-
Daniel Berk: Yeah ...
Jonathan Goodman: in, in, in, um, January. And so there's like, there's like three options.
Daniel Berk: Sure.
Jonathan Goodman: So I'm always looking for constraints. Even when we decide to go to a place, like we were in Crete, for example, in Greece. How do you decide, even once you decide to go to a country, how do you decide where to go to in that country? And even when you decide what city, where in that city?
Daniel Berk: Tell me how.
Jonathan Goodman: And so I work backwards from what's important to me. Fitness is the answer.
Daniel Berk: Mm.
Jonathan Goodman: I have discovered through a yearly, twice yearly cycle of wiping my schedule clean and building it back up from scratch via first principles-
Daniel Berk: Mm-hmm ...
Jonathan Goodman: that when I schedule my fitness first, everything else falls into place. And so when we decide to go to a place, I actually research where I'm gonna work out first, and I find the workout, and I put that as the pin in Airbnb, and then I make sure that I can walk or bike there, whatever the mode of transportation is.
Daniel Berk: Sure.
Jonathan Goodman: You know?
Daniel Berk: Yeah, yeah.
Jonathan Goodman: Walk, e-bikes here in Japan, motorbikes in Bali, golf carts in, in, in, in Mexico. Uh
Daniel Berk: Yeah.
Jonathan Goodman: Whatever the crazy-
Daniel Berk: Yeah ...
Jonathan Goodman: mode of transportation is. But I make sure that I can get there. So that's how we decide, like, what town to go to, where to be. It's this process of iteration, Daniel. Like you asked why I keep doing this.
Daniel Berk: Yeah.
Jonathan Goodman: It's not a year-round sun, you know? That, that, that's not the purpose. What I realized is that I need to reintroduce seasonality into my life, and so I love Toronto. I love the frenetic, the go, go, go, the hustle culture. I love the societal, the social obligations in Toronto. I can be at a business dinner five nights a week in Toronto if I want to, right?
Daniel Berk: Yeah.
Jonathan Goodman: I love that, until I don't.
Daniel Berk: Sure.
Jonathan Goodman: After about six to eight months, then I need to get the hell out, and then I go somewhere else where we don't know anybody, where it is a focus much more on fitness and family, and it's a much more relaxed, it's a much slower pace. I love that for about-
Daniel Berk: Yeah ...
Jonathan Goodman: three to four months, until I don't, and then we return to Toronto. And the thing about renewing seasons is that you're always excited for the next season to come. Like I'm a baseball fan. Toronto Blue Jays, up until last year, were garbage. But every year you're excited for the new season. That's how it works. And so-When I started thinking about my three priorities, health, relationships, money, I realized that every season needs to have a priority focus, and I need to have a system to renew and refresh and iterate multiple times a year. So every time we leave one place, calendar gets wiped clean. We build from first principles when I enter a new place over and over and over and over again.
Daniel Berk: Do you still work while you're in those places, or is it in your mind, like, more or less vacation with your family?
Jonathan Goodman: No, I work, but I don't put pressure on myself to really push forward in work. There's a time and place for that. Uh, I'm, I'm in this phase of my life at f- I'm forty years old, where I have the golden tri- I have the possibility of the golden triad of time, of health, and money all at the same time. There's only a short window in our life where we kinda have that.
Daniel Berk: Yeah.
Jonathan Goodman: I also have young kids. I also have aging parents. I'm also probably at the highest earning potential that I'll ever be at. That's a lot of pressures kind of coalescing at the same time, and I used to find that that was very difficult to remedy, to figure out how to do it.
Jonathan Goodman: Because no matter how well I was doing on one of those three priorities of, of, of the, of the health, of the relationships, of the money triangle, even if I was crushing it in one, I'd always feel guilty for the one that I was maybe not doing as well. Work's going really well, but, like, yo, my fitness isn't as good. Or like I'm crushing my fitness, but, like, kinda should be spending more time with my parents.
Daniel Berk: Yeah. Right?
Jonathan Goodman: Yeah.
Daniel Berk: Real quick pause because this is important. If you're running a company, you already understand leverage. You apply it everywhere in your business. Most founders, they treat health like it's a rounding error. Inconsistent training, reactive eating, good weeks, bad weeks, start, stop, repeat. That was me. I didn't need motivation because I had plenty of that. What I needed was structure. I needed systems, better energy, lower body fat, more muscle, something that actually stuck and not some 12-week sprint that I would abandon when things got busy. And so I hired a coach, and it was one of the best decisions I ever made. Training built around my schedule, nutrition that survives travel, clear targets, clear metrics, daily accountability, no guesswork. And so today's sponsor is brought to you by Daily Body Coach. They are a premium online coaching for entrepreneurs and executives who want their body keeping up with their business. It's run by an exited software founder who's already a Hampton member, and yes, a bunch of Hampton members already use it. Everything's personalized. They're coaches. They're available seven days a week. And the habits they help you build survive board meetings, late nights, and back-to-back travel weeks. This isn't about looking good on the beach. It's about being strong and sharp in your 40s, 50s, and 60s. So if you're serious about it, go to dailybodycoach.com/hampton. Like, dailybodycoach.com/hampton.
Jonathan Goodman: And so I designate seasons to prioritize one arm of that triangle, one side of that triangle. The other sides of the triangle aren't ignored, but I make a checklist for them, call it, like, the wheels on the bus checklist to make sure the wheels don't fall off the bus, more than anything so that my monkey brain doesn't feel like I'm losing-
Daniel Berk: Mm-hmm
Jonathan Goodman: ... in those places while I'm gaining in the other. This is where I push back on consistency. Yeah. I'm consistent in the two. I'm intense on the one.
Daniel Berk: Yep.
Jonathan Goodman: Intensity transforms. Consistency is what maintains.
Daniel Berk: That sounds just like a personal trainer to me. I feel like I'm in the gym right now learning how to, how to, how to stay, how to keep the gains.
Jonathan Goodman: Bro, it comes from that, though. It comes from that. I mean, I don't know, I don't know a single person who has ever achieved anything meaningful with their health, with their family, or with their business that hasn't gone through multiple intense periods in order to achieve it.
Daniel Berk: Yeah.
Jonathan Goodman: I think consistency is undoubtedly important, but you have to have those intense periods of focus. Um, there's a lot of lip service to focus. I don't see much focus.
Daniel Berk: That's great. Tell me more about the split. When you're at home in Toronto, what does your monthly spending look like? And then when you're abroad, right now you're in Japan, we can use that as an example. Right. Sure. Of course, the spending's gonna look different with all the different countries you listed. But walk me through the personal spending in a normal nine-month period in Toronto versus the three-month period abroad.
Jonathan Goodman: Yeah. I mean, it's usually four to six months abroad. And, and to be honest-
Daniel Berk: Four to six months
Jonathan Goodman: ... it's probably gonna be-
Daniel Berk: Okay
Jonathan Goodman: ... it's probably gonna be six months, like, moving forward. We'll probably be-
Daniel Berk: Okay
Jonathan Goodman: ... two-
Daniel Berk: So you're gonna do half and half then?
Jonathan Goodman: Probably for the next couple years.
Daniel Berk: Great.
Jonathan Goodman: Only because school is becoming more important.
Daniel Berk: Yeah. Uh, that's true. So-
Jonathan Goodman: Your kids' age makes, uh, makes sense.
Daniel Berk: That's right.
Jonathan Goodman: So we did one school semester in Bali, and we're doing one school semester here in Japan. Uh, each of three months.
Daniel Berk: Do your kids enjoy that? Is it, is it easier for them to transition across a border and almost be a stranger to their, their group of friends in, in school?
Jonathan Goodman: You know, they do. My oldest particularly. My middle guy is four.
Daniel Berk: Sure.
Jonathan Goodman: He would just be starting kindergarten next year, so he's technically actually in school earlier. He doesn't know any different.
Daniel Berk: Yeah.
Jonathan Goodman: My oldest, who's eight, turning nine in next week actually, he's never not known this.
Daniel Berk: That's true.
Jonathan Goodman: So he enjoys it. He's very much a part of the conversation now. And when we decided last year that we wanted to do a bigger trip, he was in a, a local school in Spanish in Mexico last winter. And we asked him if he was down to do a longer trip, and he said, he says, "I, I, yeah, yeah, Daddy, I, I'd love to, but I wanna be in school. I don't wanna be homeschooled."
Daniel Berk: Yeah.
Jonathan Goodman: So he's very self-aware that way. We have met other families abroad that have kids around the same age that have different lifestyles similar to ours for as long as we've been doing it, whose kids are starting to push back. And if that happens, you know, they're a part of the conversation.
Daniel Berk: Yeah. Cross, cross that bridge.
Jonathan Goodman: We might stop doing this.
Daniel Berk: Yeah. Yeah. Yeah. Probably. Totally. Cool. You wanna know about spend?
Daniel Berk: Yeah. Tell me about your spend in Toronto. We'll start there.
Jonathan Goodman: Yeah, I mean, Toronto, um, call it 12 months per month. 12, 12,000 a month. One, 12.
Daniel Berk: 12,000 a month. And how does that break down?
Jonathan Goodman: 12,000. About $8,000 a month in the mortgage.
Daniel Berk: Okay.
Jonathan Goodman: Um, we have a low rate. Canada has five year terms, so we actually just renewed it. Uh, we have a low rate, and so there's no point in, like, paying it down. It-
Daniel Berk: Yeah ...
Jonathan Goodman: we, we chose a variable, and if the rates spike up, we'll just pay it down super aggressively.
Daniel Berk: And this is all Canadian dollars, by the way, right?
Jonathan Goodman: This is all Canadian dollars.
Daniel Berk: Okay.
Jonathan Goodman: Yeah.
Daniel Berk: Cool. Yeah. Just for the listeners to know that.
Jonathan Goodman: Food prep, babysitting, groceries, about $3,000 a month. I imagine groceries as my kids get older, I'm already seeing it is gonna start to go up.
Daniel Berk: Yeah. I cannot... Even, even the eight-year-old, man, when he decides he wants to eat, it's gonna get expensive real soon.
Jonathan Goodman: Yes. And then, you know, things like entertainment and eating out, about $1,000 a month, unless the Blue Jays make the World Series.
Daniel Berk: Yeah.
Jonathan Goodman: In which case-
Daniel Berk: We can cross our fingers. I'll cross my fingers for you with that one ... many more.
Jonathan Goodman: Well, it was, it was cool last year. I mean, this is one of the really cool reasons. Can I, can I share a story that's-
Daniel Berk: Please ...
Jonathan Goodman: was really fun last year? So I grew up huge baseball guy, baseball fan, watching the Blue Jays. They've been shit for so long. My brother and I, he's a year and a half older, but my brother lives in Nova Scotia, which is a-
Daniel Berk: Okay ...
Jonathan Goodman: three-hour flight away from Toronto. So the Blue Jays are in the ALCS. They win game six against the Seattle Mariners. It's 11:19 PM at night. Game seven is the next day. I text my brother and I say, "I just bought you a flight, and I have tickets tomorrow. Get your ass on a plane."
Daniel Berk: Nice.
Jonathan Goodman: 9:00 AM, he shows up at my house. We go to game seven of the ALCS together, my brother and I. Jays win, make the World Series. Incredible. Game seven of the World Series now against the Dodgers. I text him at night after game six, "You know you're getting your ass on a plane again, right?"
Daniel Berk: Yeah, the plane's at your door-
Jonathan Goodman: He comes in-
Daniel Berk: ... right now. You're getting a chauffeur this time.
Jonathan Goodman: He comes in for game seven of the World Series, and we go together again.
Daniel Berk: Wow.
Jonathan Goodman: Spent about 15,000 bucks on tickets and flights.
Daniel Berk: Yeah. Phew. Why not?
Jonathan Goodman: The best.
Daniel Berk: That's a memory-
Jonathan Goodman: The absolute-
Daniel Berk: ... that's so great ...
Jonathan Goodman: the absolute best. So yeah, about $1,000 a month.
Daniel Berk: Yeah, sure. Sure.
Jonathan Goodman: Unless, unless the Blue Jays make the World Series. Yeah. Honestly, man, expenses beyond the mortgage are pretty inconsequential and small.
Jonathan Goodman: Our favorite things are free and close to us. Right. I don't wanna get in a car. I want to ride my bike. Allison and my favorite date is to take our paddleboard down to the river with a sandwich, and we just paddle and float and eat a picnic on the paddleboard.
Daniel Berk: That's nice.
Jonathan Goodman: Like that, and that's the same thing as I get into the conversation about spending money traveling. Like-
Daniel Berk: Yeah
Jonathan Goodman: ... we spend a tremendous amount of money on things like nannies when we travel-
Daniel Berk: Right
Jonathan Goodman: ... so that Allison and I can do like what we did last night, where we take the train to Fujikoma and go up the second floor and have, I shit you not, horse sashimi-
Daniel Berk: ... for like 20 bucks. Nice. Wow, okay.
Jonathan Goodman: In this little place where there's no English, and sit on the floor on, like, little pillows. Like, like, the best experiences to me don't cost much money. The part that costs money-
Daniel Berk: Yeah
Jonathan Goodman: ... especially when you have young children, are things like babysitting, childcare-
Daniel Berk: Yeah
Jonathan Goodman: ... that type of stuff. So what do we, what do we spend when we're abroad? First of all, friends stay at our home. We don't rent it. To me, a home is a home.
Daniel Berk: Mm-hmm.
Jonathan Goodman: It's special. It is memories. I can make money in other places. I choose to view my home as a sacred spot. The people staying there this year is a nanny who lives down the street working for a family for eight years, finally was able to get her husband residency in Canada, and so they're staying in our house while they set up their lives together.
Daniel Berk: Cool. So you're still paying the mortgage then and, and allowing them to stay there.
Jonathan Goodman: We're still paying all the expenses-
Daniel Berk: Cool, cool
Jonathan Goodman: ... and the mortgage.
Daniel Berk: Cool.
Jonathan Goodman: They take great care of our house, but also they're making memories in our home-
Daniel Berk: Yeah
Jonathan Goodman: ... that makes our home more special.
Daniel Berk: Yeah.
Jonathan Goodman: All other costs are about the same regardless of where we're living, you know, like entertainment, eating out, food prep, babysitting, groceries. They were about the same, so I kind of just ballparked them about the same.
Daniel Berk: Yeah.
Jonathan Goodman: There's an additional about $150,000 a year that we spend-
Daniel Berk: Yeah
Jonathan Goodman: ... when we're-
Daniel Berk: And how does that break down?
Jonathan Goodman: ... like for the six months abroad.
Daniel Berk: Yeah.
Jonathan Goodman: The school for the three kids, $11,000 a month, so-
Daniel Berk: And that's, is that just across wherever, whatever country, or is that with current schooling in Japan?
Jonathan Goodman: With current schooling, so we're in a program called Boundless. It's boundless.life. They operate in, I think, seven different cities. We were with them in Bali. We're with them in Japan. So that's according to them.
Daniel Berk: Mm-hmm.
Jonathan Goodman: I imagine, you know, if you were to source, like, different private schools, it could be more, it could be less, depending on where you are. So for the three kids, over the course of two semesters, you know, six months, 66,000 bucks, right?
Daniel Berk: Yeah.
Jonathan Goodman: On, on average, the homes that we rent wherever we're at is about $6,000 a month. We need a three-bedroom. My, my mother-in-law, Allison's mom, often travels and lives with us. She's here with us in Japan.
Daniel Berk: Cool. All right.
Jonathan Goodman: So, you know, we have six humans, right?
Daniel Berk: Yeah.
Jonathan Goodman: So we rent a three-bedroom. So it's about 6,000 a month. It's about 25,000 bucks, I figure, for a six-month period on flights and vehicles. Vehicles change wherever we're at. Like I said, it was motorbikes in Bali. It's, it's, it's e-bikes here, plus trains in Japan. Flights are a lot, but you only really fly there basically, and then you fly out. And then I'll ballpark another about $25,000 or so over those six months for sightseeing. Like, next week is Golden Week here in Japan. We're gonna go down to Osaka, and s- we're spending five days in Osaka. We'd be doing some of that kind of thing if we were at home in Toronto, but-
Daniel Berk: Yeah
Jonathan Goodman: ... figure it's about 20. So, so if you add all of that up, it's about $150,000 a year on top of what we would otherwise spend. So the way that I did the math for you here is base of $12,000 a month, and then I took that extra 150,000 over six months and I just split it across 12 months.
Jonathan Goodman: You're looking at about 22 to $25,000 a month spend-
Daniel Berk: Cool ... is where we're at. Okay. In our conversation ahead of time last week, you mentioned that one of your goals is to be able to disappear for a month and have no one notice, and I'm, I'm curious, it's a very specific metric. Where did that come from? And, and what happened in life for that to become your definition of freedom?
Jonathan Goodman: Not that I want to disappear. But I think the fewer people who rely on you, the more machines that you can build around you, the better. Like, if I have a project that I wanna focus on or if something happens that's unexpected where people need me, like, I don't know, my wife getting cancer, which happened, or my wife getting pregnant and being bedridden ill for two and a half months, and I take on a lot more of the household responsibilities. The only thing that I think you can expect with any degree of expectancy in this life is that at one point the unexpected is gonna come and kick you in the teeth. I think it's very important to keep your cup half full, because at one point something's gonna come and you're gonna be really happy that you have that extra space. It's very common to fill our cups to the brim these days. There's a lot of pressure to do that. Well, that's fine until something unexpected happens.
Daniel Berk: Yeah.
Jonathan Goodman: And you never know when that's gonna happen, how it's gonna be, right? But that's when life gets miserable. So look, I always work backwards. I find that my brain is really good at identifying an end state and then working backwards and building a plan to move forwards. So I identify my lifestyle properties, right? What do I, what do I wanna be in place? Basically, I wanna be able to spend a ton of time with my family, I wanna lift weights, and I wanna write books. Like, like, that's what I wanna do. So let's work backwards and figure out how to make that happen. So I just, I just onboarded a five-person team, which costs $13,000 a month, to basically produce and publish my content for me. And so I was able to finally delete all social media off of my phone.
Daniel Berk: Wow.
Jonathan Goodman: Now, this isn't me saying that social media isn't important. This is me saying it's really important, but I don't, I don't buy into the fact that I need to be connected all of the time. And so we have an AI layer on the bottom of it. We have two content writers. We have a project manager, and we have two VAs. And I get one email a week that's in my inbox on Thursday morning. That email has all of the content for me to review, has any questions for me and FYIs, and I commit a half day to a day a week where I'm the last touch on every single piece of content that goes out. But I get one email a week and I go through it. I put on old school hip hop.
Daniel Berk: Nice.
Jonathan Goodman: Going to see Wu-Tang Clan here in Japan actually next week. And just whip through it and edit it, and then they take it and they schedule it.
Daniel Berk: Yeah.
Jonathan Goodman: If there are questions personal for me in the DMs and stuff like that, they get screenshot, they get sent to me through Telegram.
Daniel Berk: Nice.
Jonathan Goodman: Because Telegram I only use for work. There's no notifications.
Daniel Berk: Yeah.
Jonathan Goodman: And it works-
Daniel Berk: No family ... wherever you are, so.
Jonathan Goodman: It works wherever you are. And I respond to the DM, to the VA who's sending it to me, in Telegram, and they copy and paste it back to the DMs. My stories is wherever I'm at. I take a picture and a caption and I text it-
Daniel Berk: Yeah ... to a VA.
Jonathan Goodman: I buy in that this stuff is important.
Daniel Berk: Mm-hmm.
Jonathan Goodman: But I, I don't accept that it's something that needs to diminish my quality of life or ability to focus or presence-
Daniel Berk: Yeah ... with people I love. So, uh, that, that's a good segue to something I thought about with something you've written and I've been wrestling with.
Jonathan Goodman: What's that?
Daniel Berk: The idea of retirement.
Jonathan Goodman: Yeah.
Daniel Berk: When I think of my threshold number, let's call it $10 million. I'm not there yet.
Jonathan Goodman: Sure.
Daniel Berk: But when I get there, I think of what I will do not having to make money, and it looks a lot like whatever I want, and it doesn't look that much like work.
Daniel Berk: But something you wrote, it's a calculation actually, and you kind of divulged this to me in our last conversation. It's in one of your books. Working 10 years longer reduces-
Jonathan Goodman: Yeah ...
Daniel Berk: the required savings by something to the effect of 96%. It's insane. Which I think is, uh, obviously a very provocative claim.
Jonathan Goodman: Mm.
Daniel Berk: And I'm curious, is there something emotionally uncomfortable to you-
Jonathan Goodman: Yeah ...
Daniel Berk: or even to the philosophy that you've built your framework around money about retirement? Or is retirement something entirely different to you than not working?
Jonathan Goodman: Well, first, first where that number and calculation comes from, all the credit to David Coburn, who wrote a fantastic book called Let's Retire Retirement. Financial advisor, great guy. But the numbers of course change a little bit, but the calculation that he did is he said if you expect to work at 60, until you're 65 years old and then your income goes to zero and you're just pulling from your income, you need to save... And again, all the numbers change depending on how old you are. But the calculation that he gave is he said you have to save $4,000 a month, right? Which means that maybe you won't go to as nice dinners. You're not gonna take unpaid time off, et cetera. If you expect to work in some capacity until you're 75 years old that generates even $1,000 a month in income, that number decreases by 96%. You only need to save $200 a month. And what that means is, yo, go out for that nice meal. Do what we do. We rent a huge cottage or house multiple times a year, and we just invite our friends. We have a number of rules. One of them is book it and then invite them. Instead of saying, "Hey, do you wanna do this? Do you wanna do this? Do you wanna do this?" We have booked a six-bedroom cottage on the water in the summer for this weekend, first come, first serve. You want in or not, right? You can book that. You can spend the $12,000 and book that.
Daniel Berk: Yeah.
Jonathan Goodman: You can take that unpaid time off. You can maybe not take that promotion that would take you away from your kids while they're young. Whatever, right? It's a very provocative calculation. Look, the odds that any of us that are listening to this, that are by our very nature entrepreneurial or thinking this way that we're gonna find a podcast like this, you're not gonna stop making money, man. You might not be as aggressive or financially ambitious. You're gonna make something when you're older. I mean, it's just gonna happen. And so what I've done myself, my philosophy is this, is that we need a better definition of terms. Similar to like every guy, a friend is somebody that you met once at like a colleague dinner, and a friend-
Daniel Berk: Yeah ...
Jonathan Goodman: is somebody you know-
Daniel Berk: You don't even know their name ...
Jonathan Goodman: since you were eight. Like-
Daniel Berk: Yeah ...
Jonathan Goodman: like yo, we need like, like we need a different term for buddy, like, like as a-
Daniel Berk: Yeah. Yes. It's, it's, it's kinda the same.
Jonathan Goodman: Your job is what you do for money. Your work is what you do for you. It is very important to understand the differences between these two things. Once you've made enough money in your job, it's important to stop that goal line from moving. When it comes to your work, though, you should never stop that goal line from moving. You'll never hit it. Continue to push that down the road as much as you possibly can. We're told growing up in North America that we should follow our passion, and I think that we should, but I think our passion should be our work, not our job. Because very often, when our passion becomes our job and we rely on the money made from our work, it tends to diminish the love that we have for our passion. That's one of the benefits of living in all these other countries that I've had. Go to South Central America and live there and get to know the people there. They have deep-rooted family values. They're physically ambitious. They're healthy. For the most part, they don't really care about their job that much. They're proud of it. They do it. They show up every day.
Jonathan Goodman: It's important, but their job is what they do for money, and then they have their hobby, the thing that they love on the other side of it, and their job feeds that, not the other way around. There's something about that, and I, and I, and I, I'm not saying one way or the other is better, but I do think that it's a challenging conversation to have, and if you've reached the point where you've made enough money, yeah, you gotta get that goal line to stop moving. Doesn't mean you're not working, though. Mm-hmm. You should absolutely work.
Daniel Berk: That's great advice. I'd, I'd love to bring the ship in here for a landing by asking you if someone's listening to this podcast and they're wrestling with the, the tax game, you, you mentioned, you know, people moving to other countries to save, you know, oh, it's only 2% tax. You even said earlier, if you're not getting taxed here, you're getting taxed somewhere. What do you tell the person that, let's say they're in Canada right now, and they feel-
Jonathan Goodman: Right.
Daniel Berk: ... the tax pressure, and they're looking-
Jonathan Goodman: Yeah.
Daniel Berk: ... at Miami. What's your advice to that person?
Jonathan Goodman: I mean, work backwards from your lifestyle properties. What do you want your day to look like? That's what we do in fitness. What do you want your body to look like? What do you want your health to look like? Cool. Imagine that is the reality now. Work backwards. What needs to be in place in order for you to get there? Okay. Are you willing to do that or not? Be realistic. If you're not, we need to adjust the end state. If you are, then there's only one question left. Are you gonna do the fucking reps, or are you not gonna do the fucking reps? That's, that's the first law of fitness. Figure out your goal, figure out the reps to accomplish that goal, then it's a binary decision. You can do them or you're not. So it's not me saying, "Don't move to a tax-free state." Instead it's me saying, "Where do you ultimately wanna be? What do you wanna be doing every day? What's the pace of your life? Who do you wanna be around?" Okay. Work backwards.
Daniel Berk: Yeah. What does that look like? Seems like you've figured that out more than a lot of people. A lot of people are still chasing for what's next, what's more, are not satisfied. When I hear you talk about your life, it sounds like you, you're satisfied, like you, you have a full, rich life. What would you say to people who are, uh, can't ever be satisfied, they can't ever get enough?
Jonathan Goodman: Just find the right thing to chase. I decided that I wanted to build a profile in the authorship space, and that's been really difficult. It's been really challenging, but it's been something to chase, and it's been fun. What is it that you consume an unlimited amount of content around and you're never bored? That's probably the right thing for you to chase with your work. Not necessarily for your job, but that's a pretty good indicator of what... I mean, I can listen and read an unlimited amount of books about books, about writing, about how other authors live, about their... I owned a B2B SaaS platform called QuickCoach. It's the biggest professional loss I've ever had. I lost 1.4 million bucks on it. Well, it was stupid that I even did it. I couldn't even make it through a five-minute YouTube video on SaaS. It bored out of my goddamn mind. Shouldn't have done that, even though it was a good opportunity. People who bought it from me, I mean, at a huge loss, are gonna make millions on that thing, and I hope they do. So what I'll say is it's not any different advice. It's know thyself. What do you naturally, what naturally appeals to you?
Daniel Berk: Yeah.
Jonathan Goodman: What can you listen to? What do you read when nobody's looking? How can you figure out a way to challenge yourself with that and pursue that as much as possible and remove the money equation from it? Make your money elsewhere.
Daniel Berk: That's great. That's great advice. John, this has been incredible. I appreciate your time.
Daniel Berk: I appreciate you sharing your thoughts, your frameworks, your philosophy on life. I think it's incredibly interesting that you travel like you do. People travel, right? Travel is a, a novel concept, but what you're doing with your family every year, almost, uh, clockwork, and you're thinking thoughtfully about where your kids are gonna go to school, and even involving-
Jonathan Goodman: Right
Daniel Berk: ... the older kids in the equation, I mean, I think it's just a very intentional way to build your life. I really appreciate you sharing that with us today.
Jonathan Goodman: Yeah. It was... This is stuff I never get to talk about, so this is fun. Thank you.
Daniel Berk: Yeah, absolutely. Thanks, John.