Your Seat at the Table - Real Conversations on Leadership and Growth

Breaking Scarcity and Redefining Wealth with Garrett Gunderson

• Mike Maddock & John Tobin

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Ever notice how money advice often tells you to wait—save more, take more risk, and hope it all works out decades from now? We flip that script. With Garrett Gunderson, we explore how to break scarcity thinking, redefine wealth as the power to be present, and design a life you don’t want to retire from. For decision-makers dealing with financial anxiety—and for any leader who’s ever felt alone in tough calls about money—this conversation reframes wealth as stewardship, not accumulation.

Garrett shares the family stories that seeded his early money fears, the hard-earned lessons from 2008, and the shift from hoarding to intentional design that changed his marriage, health, and business. The throughline is question-driven: instead of asking how much you can pile up later, ask what your money should be doing for your life right now.

We dig into three sticky myths—“it takes money to make money,” “high risk equals high return,” and “you’re in it for the long haul”—and show how each one quietly asks you to outsource agency and delay joy. Garrett introduces investor DNA: risk lives in the investor, not the investment. Focus builds wealth; diversification preserves it. It’s a form of peer-powered disruption in personal finance—less hype, more clarity, and decisions you can actually explain.

We also unpack fee blindness and why a single percentage point over decades can erase hundreds of thousands, making transparency and low-cost structures non-negotiable. From there, we move into the systems that protect what money is meant to serve: weekly marriage check-ins, vision sessions, and family traditions that anchor presence. Sometimes the most powerful move is deciding what’s not your problem—and letting money stop stealing attention from what matters most.

Garrett also reveals how he simplified his portfolio to align with his values and built a modern, accessible family office model for entrepreneurs on the rise—pairing coordinated legal and tax strategy with AI-powered workflows to save time, cut costs, and increase accuracy. For anyone ready to challenge their comfort zone around wealth and run toward the roar of financial truth, this episode offers a practical path to cash flow, resilience, and meaning—without “set it and forget it.”

Real leaders. Real stories. Real action. If this resonates, follow the show, share it with a founder who needs it, and leave a review with the money myth you’re letting go of next.

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SPEAKER_00:

All these really wealthy people have a family office.

John Tobin:

Yep.

SPEAKER_00:

But what about all the entrepreneurs on the way up? They don't have that comprehensive, coordinated team. But thanks to AI and thanks to my ability to partner with attorneys and accountants now, we can offer those full services at a fraction of the price and still be wickedly accurate, extraordinarily efficient, and get people's financial house in order. It's like I'm so fired up about it because it's been my life's work that finally came to fruition this year, really.

Mike Maddock:

Welcome to the Your Seat at the Table podcast with your host, Idea Monkey Mike Mattock, and ringleader John Tobin. We're two founders, a serial entrepreneur and a billion-dollar operator, to talk to leaders about how, when, and why they made their most pivotal decisions in life. Join us as we share wisdom, mistakes, and a few laughs learning from the brightest minds in business today. Some people think about uh how you spend your money, how you spend less money, how you save your money, how you invest your money, how you diversify your money, how you protect your money, how you grow, earn more, fear your money, make your money last, make your money do more, protect your money, donate your money, make your money create generational wealth, pay less taxes on your money. Garrett is my favorite money muse because he's thought about all of that and way, way more. 15 years ago at MIT at an entrepreneurial conclave, Garrett gave me the gift of a paradigm shift about money that I never forgot and has made my life and my family's life way, way better. So thank you, Garrett, for giving me that gift. Appreciate that. You're my favorite money muse. That's what I call you. And you've written one of the best-selling books on insurance, but you don't want to sell anybody insurance. You've done a stand-up special about money, a comedy special. So you can catch that on Amazon if anybody wants to see that. You've written all kinds of books. You've thought about money more than anyone I know. So before we start peppering you with questions about money, we have lots of them. Tell us how you came to think about money so much in your life.

SPEAKER_00:

My family kind of struggled with money from a standpoint of like my great-grandfather wasn't making enough in Italy. So he left his pregnant wife behind to come to America to provide a better life, which meant originally he was a goat herd because there was a mine disaster before he finally became a coal miner and met his daughter at seven years old for the first time. So that created like folklore in our family, like a level of scarcity that you got to hold on to what you can, that if you don't have enough money, you could lose your family and lose everything that you care about. So it became like very much miserly hoarding, you know, putting cash in coffee cans, putting them in the cellar, uh, you know, having the first dollar they ever earned. I think my great aunt applied for welfare, but they denied her because she had$550,000 in savings because poverty is kind of a mindset, not always a bank account, you know? And so that was that was like the and I believed for a long time, yeah, you know, like it's just how much you can save. Like that was my original thought until when I was selling insurance, I got my first MDRT award, which is an insurance agency award. And I was really proud. And then I talked to this woman, Nancy, and she's like, I can't wait you get to the top of the table. You'll see they view money differently. And I was like, Well, what do you mean? And I just kept asking her questions, and then she's asking me questions, and I'm answering them with like saving, saving, scrimping, sacrificing, delaying, deferring every answer until she goes, I wonder what it's like living in the financial prison you built for your wife.

Mike Maddock:

I was like, Oh, well, yeah, I'm kind of the issue. So say more about that. What kind of financial prison? Because I I know that there are a lot of couples that think about money differently. Um my wife and I think about money a little bit differently. How did you build a financial prison for your wife around money?

SPEAKER_00:

Well, if we went back to we we were dating in college, and I was fun, I was romantic, we did great things, and then when we got married, we moved in together, and all of a sudden I was like, I'm responsible for the you know safety, security, and protecting this family. And so I just went into I'm gonna work as much as anyone could ever work so we could live a better life in the future, and I'm gonna save, like no one can save, but we'll live in this crappy apartment, even though we're making six figures, which you know, back in 2020, that was something. And uh, and basically just I was arguing over the heating bill. I was pinching pennies with the budget every day. Like she was like, I didn't know who I married, is what she said. She's like, it was like a different person because that different, like, you know, my family heritage kind of came in and was like, ooh, you never know what could happen. You better hold on to what you got.

Mike Maddock:

So you were selling in a million-dollar round table. That's MDRT. So I am and top of the table is for the top one quarter of a percent of insurance people. You were selling insurance at that time, is that right?

SPEAKER_00:

Yeah, I was selling insurance. Uh started when I was 19 years old at Guardian. And uh, you know, I was I was trying to tell people I was a financial planner, but I was really just an insurance salesman, but I didn't like saying that. Yep. Um I've known many of those. Yeah, I just didn't feel like my tie was short enough or my belly was big enough at the time to say I was selling insurance, so I tried to sound better than I was. Um, and then I pretty much sold insurance to like 2006, and then I was gonna go speak at a guardian agency, and Guardian Compliance said, We need to see your talk. I was like, Well, I don't know exactly what I'm gonna say, but here's the gist of it. And they're like, Yeah, you can't do that. I said, What if I wasn't insurance licensed anymore? Then you could do that. So I resigned at that point, gave up my renewals, started doing radio shows, started writing books, that kind of stuff instead of selling insurance.

Mike Maddock:

And the that is the book Killing Sacred Cows, right? Was that the book we're talking about right now?

SPEAKER_00:

Yeah, I wrote that thesis that there's nine financial myths, nine financial myths that people don't understand or see because they're the the they're very elusive, they're very subtle. Like if they were obvious myths and obvious lies, we would point it, we would know, but they're so subtle that people actually believe them. And so I kind of point them out so that people go, Oh, I can now avoid that myth or mistake. And it kind of gives them permission to prosper, permission to succeed, and it helps them to think more abundantly versus coming from scarcity, kind of like my background of scarcity to becoming more from a place of serving others, solving problems, adding value, and realizing that there's not a finite pie that exchange actually creates wealth. And so, how do we create more exchange? How do we add more value? How do we all that? Yeah.

Mike Maddock:

Okay. Are you well that what are they? Let's let's hear some of a couple.

SPEAKER_00:

All right, so let's just we'll pick three. Because all three are kind of inside of financial planning. The first one is, and I've heard so many people say this, it takes money to make money. That's like one that they say, it takes money to make money. Well, that's like a chicken and the egg scenario, right? Like, you know, like how how did money even come about? It was just a man-made efficient tool to exchange. So it takes relationships and ideas, value and exchange. And when we think it takes money to make money, we become less resourceful, less resilient, we feel more defeated. And the people that tell us it takes money to make money, it doesn't take their money to make money, it takes our money for them to make money. If you think about Wall Street, they're getting paid fees, whether you make money or not, all that kind of stuff. It, you know, so that that's the first one. The second one is high risk equals high return. Like we've heard that how many times? But risk means chance of losing. So increasing our chance of losing doesn't help us win. What it does is it gets us separated from the outcome of our money. And we go, well, I don't know, so I'm just gonna trust Wall Street. Would we trust Wall Street with anything else? Like, what kind of brand is Wall Street? Wall Street Airlines, you flying them, Mike, you're getting on that flight today. How about Wall Street Daycare? Are you taking your kids there? They're like, oh, sorry, we lost 7% of your kids, but it's just toes. You know, I mean, like somehow the people that we have the movies, Wolf of Wall Street, Wall Street, you know, boiler room, we're like, yeah, that's where we're gonna hand our money over and trust what's going on. So the riskiest thing we do is not know what's going on. And then the third thing is you're in it for the long haul. Well, that has us neglect stewardship, neglect creating cash flow, waiting for 30 years, not measuring whether it's working or not. It's always this narrative is just set it and forget it. Invest really often and always. So this belief that wealth is a function of how much money can you put away, how much risk can you take, and how long can you wait has failed 95% of the time, because 95% of Americans are not financially independent at age 65. That's a 95% failure rate because there is no understanding of if it's working or not. And ultimately, what most of the advice is is you turn, you see these Gubers that go, well, if you just start at age 20 and save$2,000 a year, that's more than if you wait till 30 and save all the way till you're 60. Well, what happens to those people that are 30, 40, and 50? Or what happens when 2008 occurs or 2020 occurs? Because, you know, like we have all these losses. And if you have a hundred grand and you lose 10%, you're down to 90 grand. When they when you turn on the news, like the market's ried, it's back up 10%. Yeah, 10% of 90 grand? That's not even back to your 100,000. You lost the time value of money, and you probably had to pay fees. So we've just been indoctrinated to neglect our money, to just hand it over because we're told it's just too complicated. Trust someone else.

John Tobin:

Yeah. So is that is that part of the premise to manage your money yourself? Like don't uh don't give it to Wall Street, like you said, or is that and and maybe maybe uh like there's a there's a little skepticism for me, a little bit, just you know, like kind of uh I'm definitely you know uh didn't come from money. You know, had and my my dad definitely was more like what you're talking about, where it was buy a house, save, save, save as much as you can, scrimp where you can, uh paycheck to paycheck. He was uh I was one of seven kids and he was a teacher, you know, good guy, really smart, but didn't make any money. He would work on the weekends as to make ends meet, and um I remember literally payday on a Friday, Thursday, every other every other week, you'd open the fridge, it'd have nothing in the fridge, a thing of water, baking soda in the corner, condiments on the on the shelf. My mom would make breakfast for dinner typically, just to make ends meet. And so I grew up like thinking I've gotta have money. And like my parents didn't fight a lot. What they fought about was money. So like that's that's my relationship with money was like I better have a lot because I don't want to be as miserable as they were. Anyway, so my point is like what do you what do you tell people when they're younger, I guess, to get them to start to think like this.

SPEAKER_00:

So there's a lot to unpack in that. And the first thing is which I love, um you know, the first thing is all right, I get there's a lot of people out there that are just W-2 earners that are not in some doing something they love, they're exhausted by the end of the day. And so for some of my advice, it can't really apply to them because my first advice to people is discover your investor DNA. See, risk isn't in the investment, it's in the investor. So, what kind of investor are you? I was told in my early years, if you're gonna be wealthy, you got to own a lot of real estate. Well, guess what? I owned a lot of real estate and it didn't make me wealthy, it made me exhausted. I'm talking to bankers, attorneys, property managers, you know, I'm talking, I'm talking to like maintenance people and tenants only if they're very upset. Like it wasn't a good situation for me because I didn't love looking at spreadsheets. I didn't love looking at property, I didn't love the entire process. But that was one of the things that gurus would say is you got to own real estate. Well, not if it's in your investor, if it's not your investor DNA, which is what are your like core values? What are the things that you deem important? What are your core competencies? Where do you have an ability to learn at a more rapid rate in a category more than another? And then what is your focus? Because we've been told forever diversify, but diversification is great for preservation. It's admission of ignorance on the way up, though. I don't know how it's gonna work. I'll just spread myself thin. And so I think you've had I just met you, but from the early story, is like you've had to have a pretty amazing focus to build what you've built. And you've got some pretty amazing investor DNA in what you've done in business to create what you've created. So I get that maybe a teacher isn't gonna go do that. Maybe they need to follow with less guilt and shame the Dave Ramsey model, because I just feel like he guilt and shames people a little bit too much, but at least he's and he's gotten he's gotten a little arrogant and cocky.

Mike Maddock:

He used to be so humble, not to go after Dave, but I I'm a big fan of his, but now he's like, well, what? Like now he's just snarky. Like, what happened to the humble, I lost everything, Dave Ramsey?

SPEAKER_00:

What happened was he's he's he's got a conflict in his philosophy, and this is the conflict that will help answer the question. We've seen over 20, 30 years index funds beat managed funds the majority of the time, especially even hedge funds, which are supposed to be the best of the best. So he's selling leads to financial people that are doing managed funds so they can get paid, which to me is against the philosophy of reducing expenses. And only because we go, oh, well, it's a percentage. 1% doesn't seem that much. 1% on a hundred grand over 30 years, if it earned 10%, it would grow to$1.74 million, no tax, no fees. If you only earn 9.2% because of fees, it grows to$1.4 million.$340,000 cost from that fee. So where I'm saying, like, hey, people that spend more than they make, they've got to they've got to create a more strict budget. Maybe the best thing they can do if they just blow money is pay off a mortgage and fund a retirement plan. My problem with that is it's extraordinarily one-dimensional. You've only deferred taxes, not actually saved them. You've you've worked against inflation by using every extra dollar to pay off a loan with valuable dollars today that would have been less valuable in the future, which allows you to grow. So, like, I just think that a lot of the advice is this people, and this is I've talked to too many gurus one-on-one, and they'll say people are stupid. I hate that sentiment. Like, I'm like, if they were so intelligent around finance, why how would you make your millions and tens of millions of dollars? You know, it's like we have to help people. They've been they haven't been trained in this, and if school tries, they don't do any better. The economist did an article in 2014 that showed almost no statistical relevance on training kids about money in school. And part of it is because personal finance is different than economics and corporate finance, but economics and corporate finance tell us more about money than personal finance. Personal finance looks at it too one-dimensional. Here's a good example. Let's say that, you know, let's say I'm willing to lend you money today and I'm not gonna charge you any interest. How much would you take?

SPEAKER_03:

As much as you give me. Right.

SPEAKER_00:

How fast do you want to pay me back if I'm letting you come up with the terms?

SPEAKER_03:

As slow as possible.

SPEAKER_00:

Super easy, but like Dave Ramsey says he wouldn't take a dollar, which is just absurd. Um, because you could arbitrage that by putting it in the safest thing possible and you're still in a positive return. Um, but it's because of the dogma in his mind and not looking at the economics. And so what people do is we see like now they're talking about 50-year mortgages, and almost 99 out of 100 people go, This is crazy. Look how much interest you pay, which shows they know nothing about how interest works. See, if I can earn 5% or I can pay 5%, I always have an interest cost. If I pay cash, I forfeit the right to earn 5%. If I borrow, I pay the 5%, but then I can still have my money. Like, so if I have a 50-year mortgage and I pay it like a 15-year same payment, if it's the same interest rate, it pays off in 15 years. I get most people won't do it that way, but we have to at least look at what's really going on to inform people so they can make better choices rather than go, they're not gonna understand it. Let's just tell them pay it off. Don't do it.

Mike Maddock:

Yeah, that's a challenge. People don't know that you know, paying uh$500 more on their mortgage creates anyway. I so uh you let's talk about wealth. You have a great definition of wealth. I think it is the best definition I've heard. So talk about that for a second. What what how do I know if I'm wealthy?

SPEAKER_00:

If you have an ability to be present. And and that's the thing, yeah. The model I shared with you, right? That that wealth is a function of how much money you can put away, how much risk you take, how much time you can wait, that's never about being present. That's about chasing a one day. That's about having more someday. And so it's like sacrifice today because one day it's gonna pay off. And look, there is there's so many studies that we've seen, right? Like the marshmallow experiment and all this kind of stuff, that if we have the ability to be patient, that's different than sacrifice. It's saying, What is it worth it? It's opportunity cost, it's it's looking at the big vision, but for too many people in finance, it's if you will live like a miser today, you'll have a better life 30 years from now. But every study shows if you're miser today, you'll be a miser in retirement. You don't have to be able to do that.

Mike Maddock:

So this is the gift, this is the gift that you gave me. This is the gift that you give gave me. And contextually, uh my I did a science fair project with a guy named Mike Roach in seventh grade on cancer. He died two years later. And my uh late wife's mother died when she was 16 years old. They saved forever, went to Norway. She was she was dead three months later. She was she was sick. They finally did that trip to Norway. My roommate from college died the day before his 40th birthday, and I saw you and came up with the because of what in in part because of what you said, uh I just decided money was for memories, period. And that we were not gonna wait a day and have made some ridiculously stupid financial decisions if you ask a financial planner. But I'll tell you what, when my late wife got sick with brain cancer, I asked her, What do you want to do? And she said, We've done everything and all those memories that we had with our own.

SPEAKER_00:

How much peace is that? Yeah.

Mike Maddock:

Yeah. I mean, we did we just did all those stupid things early. And um, I'm so grateful because you because you know that the book uh Die with nothing. They show you that graph where by the time you have money and have the physical ability to do all those things, it's such a short window. So people wait and wait and wait, and then they their bodies just won't let them climb that mountain or go on that trip. So I I want to thank you for that gift.

John Tobin:

So um So Mike, what was yeah, but was the the conversation, or was it uh Gareth, did you speak at GOT or something? Or like is that what it was? Or and and when when you when you heard that, was it this awakening, Mike? Like in terms of this is what wealth is, wealth is making memories.

Mike Maddock:

Like, is that is that how you well the it it it gave me the courage to invest in myself? And the reason is because the honestly, the most money I've ever made, the most money I've ever lost has been at my own hand, and I'm fine with that. Like when I invest in my own businesses, I am in control, I'm accountable, I have a mirror, I can blame myself. Uh so he it it it gave me the cur he he basically made the point that all the money the scarcity thinking all the money that I'm giving someone else who says wait wait wait wait wait and I've watched people do it and you have too John was was just bullshit. Like they're taking all the money that you're giving them and they're investing it so they can do all the things you want to do today. What are you waiting for? And I'm not giving you enough credit Garrett because you're much more eloquent about money. All I can tell you is the light switch went off in me and I'm just like wow that's really interesting. And I just behave differently from that moment on and I'm happy I did. Not I did a lot of things wrong I still do but it was just this awaken like huh and I have memories to show for it.

SPEAKER_00:

So I'm grateful when I when I'm when I used I don't have any money in the stock market which is as a money guy probably surprising for most people but the reason I don't is because it's not really my investor DNA and even deeper is I believe I vote with my dollars. And 40% of the S P 500 I would love to go away because I don't think they're helping humanity. I really think they're destroying it. And so I don't want to support that. Yes it's more liquid than my businesses. Yes it's more liquid than the the few pieces of real estate that I intimately know and utilize and don't even create cash flow from but helps as a hedge against inflation. You know, I just simplified my financial life if we if we go back to my 20s I believed that work was the holy grail because I was trying to prove to people that I was valuable and I was doing it through material things and through awards like I'm hitting Inc. 500 award I'm SBA Young Entrepreneur of the year. And at the same time like my wife is like I feel like a single mom. You know so like I'm losing the game of life because I said yes to every speaking opportunity. And so I had over a hundred real estate properties two oil and gas deals uh two IPOs like I had a hard money lending fund and I remember my grandfather who's my hero we hosted the Super Bowl party at my house which is for his birthday and I watched five minutes of the game because I was on the phone the whole time dealing with all this real estate stuff that was going on. I took my wife on a trip to Tempe. I was closing a real estate deal the whole time like I was never present and she was just kind of resigned to like I guess this is who he this is who he is and I don't know what to do about it. And then all of a sudden 2008 happens and it's like oh I worked so hard to build this portfolio that is just drowning right now because it wasn't really in my DNA. It was just doing it only for money. I had no real purpose other than greed I had no real competency other than basic financial knowledge but it was actually outside of my my key realm. And then 2010 comes I've cleaned it up I'm having the biggest year in business ever and my wife is just like numb like just like yeah like who cares? Here we go I'm having this like big I'm having this like really big moment where I'm like dude this just happened and she's like I brought home just like I made a hundred grand a day and they just we just took a distribution and she's like so and I was like well I thought you'd think this was cool. She's like I could see the addiction I see where we're going and so I I basically had to like I had to realize that what I was doing in business that was working I wasn't doing that in my health and I wasn't doing that in my marriage. So I just kind of reverse engineered a little bit I was like well in business I have mentors I'm reading books I'm you know I'm doing these certain I'm doing these meetings. So I'm like why don't I set up meetings with my wife every week why don't I create a vision for our marriage and say I want to be a premier romantic and extraordinary husband. That will be my vision and these weekly meetings all how am I doing on a scale of one to 10 as a husband and uh you know how am I doing as a father and like what are the big things you want to look forward to and I created this format. I was like hey we're gonna have if I'm gone more than four days in a month I take a full day off during the weekday. If we are going to spend 14 days away from the kids um for overnight trips through the year so that we could just you know and I'm like we're gonna do date night every week you don't have to worry about it in the meeting if you have ideas throw them out to me but I'm taking care of you. Like I just started doing this and then I was like you know what I'm just gonna think of like who are my best friends and this was actually when I was at uh G O T I thought of this I was I thought who are my best friends that are amazing at marriage and older than me and I picked three friends I'm like these three have the best marriages they're all older than me and my wife we're gonna get together we flew to Chicago we sat down she interviewed the women what are your best practices I interviewed the men what are your best practices and the women could convince her of stuff I couldn't convince her of like we should put each other first not the kids she's like I don't trust you to that you won't put your business first you know like you know I'm like hey we should get a nanny to support part-time she's like that would make me a failure as a mother but these women all had nannies so all of a sudden she could listen to them and I decided in 2012 I met with my CEO I go I'm gonna take so much time off this year. I don't want it to hurt the business but I want to show my wife she's our biggest priority what do you think we could do he goes I could improve our margins we could improve some of the things in our offerings that aren't profitable enough start removing them so even if our revenue dips I think we'll make the same amount of money and halfway through that year I said I'm only gonna speak 10 times I'm only gonna speak if I bring my wife and the kids which made me a horrible speaker Mike because I just show up get on stage speak and I was gone you know and I'm just hanging out with them. But my wife halfway through the year was like are we okay? Like what do you mean? She's like well like you're not at work very often you're always we're doing all these fun things and like we're spending a decent amount of money like are we okay and I'm like yeah you asked me when we were dating would I be willing to give up what I was doing if you were sick or if we had to move and I hesitated and I could see that always created this level of fear in you I'm here to show you like you're such a priority and that's been the richest reward I've had is investing in my marriage.

Mike Maddock:

Like hardest but richest I'm gonna quote you because I think this is a in a headline what you're talking about. And I think this is the central theme to um what you preach for you very like you're like a minister today. So I'm enjoying it.

SPEAKER_00:

When you design a game that is worth playing you've already won yeah when you design a game that is worth playing you've already won talk about retirement well for like you know what's crazy is I write the book Money Unmasked and it's my first book that I just wrote I had an amazing editor. She's like you know you actually might know her AJ Harper she helps uh McAlowitz with a lot of his books McAlowitz and and so like I'm writing this book and it's taken me seven years to write because I keep writing it and I like going through stuff that I'm writing about and in the book it has two main concepts. One is scarcity comes from playing not to lose which we've talked about with my family history but the more subtle thing where scarcity comes from is playing to win which is always about the future never enjoying the present right that's the playing to win and most entrepreneurs wear that as a moniker a badge like I'll I'll I'll I'll play to win you know but my dad said you never you know you can never buy back the memories you never have and and so this is kind of like going through a little bit of the story I'm sharing. And so the design of the book is how do you design a game where you've already won because the win is in the work that you've designed the life that you love so you're not ever going to retire from it. A lot of people retire from their business because they overwork themselves in the name of growth but at the expense of personal growth at the expense of quality of time at the expense of quality of life. And so as I'm writing the book I have this epiphany I've sold my business but I did a lucrative licensing deal and I'm like wait this isn't aligned with my brand they don't share my values anymore but it's seven figures a year and I'm like damn I'm playing not to lose I hate every minute of anything I do for them even though it's not a lot of time and so I'm like I'm gonna have to cut this off because I'm launching the book right now and if I don't cut this off I'm a liar. I'm still playing not to lose but at the same time I had this new thing where I had a friend that was a partner where I was now playing to win. He's going through an existential crisis hadn't done any work for like a year. I'm working tirelessly and splitting half of it I'm like oh wait play to win on one side play not to lose so I'm a relationship guy I cut off two relationships within months of each other I have so much stress that my kidney's going to stage four failure. I now have adrenal fatigue and I'm just laying in bed not able to sleep but exhausted while I'm launching a book about loving your life and I'm like why do I write these things because I know I'm gonna have to face and go through it. Like I write killing sacred cows and I go, hey net worth's not as important as cash flow, which isn't even as important as living a life that you love and I'm like eight million dollar net worth declines eight million dollars during 2008 and I'm like okay yeah you did it proved my point I've shown through example but but that was and so coming out of it it's awesome that I invested so much of my marriage because my wife was my confidant through 2004 and through this year that we built a business that we love working with people that we love but it was like I had to I had to shake like my lack of confidence from 2023. I had to get over this health thing which seemed insurmountable and and my wife helped me figure it out with the right people and the right doctors and like how I eat now and how I handle stress. So you're gonna retire and retire? I retired for about three days when I sold the business and had finished doing comedy and I realized I had nothing to do but watch TV and there was nothing on that I wanted to watch because everybody else was working. I was like retirement means to take out a service like something due to a cow behind the barn. Like when they retire a player's jersey that's not good news it means they're not useful anymore. Right? So it's like hey Mob, what do we do with dad now that he's retired? I don't know, put him in the spare bedroom next to the treadmill nobody's used. You know what I'm saying? Like retirement is an antiquated philosophy that came from the industrial age when you had to retire in order to survive and live some semblance of a life because you're working seven days a week doing assembly line work that is excruciatingly painful. And so now we're in a place where it's a different age what if like I know there's still plenty of jobs that people hate doing but for someone like you guys if you retire you remove this wisdom because you've gotten smarter over the years not less like an athlete loses a step over time. Yeah an entrepreneur gains a step and so there's so much you can contribute and give back and what I found is when I sold my business it was a really hollow feeling for a while. It was like I I felt unimportant I lacked value. Thank God I picked up comedy like immediately afterwards which was fun but it wasn't like it wasn't transformational. So you know being on the road doing comedy clubs kind of lost its luster after two years. So I really respect those guys for doing it but it wasn't going to be quality of life and family life that I wanted. So I had to go what's something I could dedicate my life to what's a vision I wouldn't retire from and you know what I'd love to do I love to sit down with people and help them build their their legacy like their family constitution which is in their own words before it we get into the legal ease of the trust or a family retreat structure or build a family you know um crest or like all that kind of stuff and people are crying they're emotional I'm emotional like why would I stop doing that that's the most richly rewarding thing that I do that's not for my family. And I even do that for my family which by the way I told Mike this 10 times harder than doing it for a client one they're just one tenth as impressed as the client the client's just like how can you do this and my family's like now what can we can we go? Like come on guys I'm trying to read I'm crying they're not so is that is that what you do and or and is that like your job would you say like now or do you just is that is that what you do like uh I don't know in in your spare time I guess like what I do eight I do 18 of those a year and they come out to my cabin which is a more of a lodge than a cabin it's on a river aspen trees everywhere and we just sit down one on one and build it out and it's like so um it's so much fun. It's not scalable but it's rewarding. I love it. So it's not the whole business I do what I've figured out and it's taken me only like you know since 1998 we just figured it out last year and it really dialed in was all these really wealthy people have a family office. Yep. But what about all the entrepreneurs on the way up they don't have that comprehensive coordinated team but thanks to AI and thanks to my ability to partner with attorneys and accountants now we can offer those full services at a fraction of the price and still be wickedly accurate, extraordinarily efficient and get people's financial house in order. It's like I'm so fired up about it because it's been my life's work that finally came to fruition this year really. I mean I launched it July of 24 but it's taken until this year that we had all the tools and resources and team to fully implement and like I'm showing other family offices what we do. We can get something done in 30 minutes that takes them 20 to 40 hours to do thanks to the models that we've built and it's it's pretty that's what I love to do. Yeah right so I mostly you know speak and write to to promote that.

Mike Maddock:

You're you're I just want to I want to make sure we land this plane because yeah uh now that you said that when you design a game that's worth playing you've already won I think that's very wise and most people the people that you're talking to have the power to to redesign their lives. They just don't think to do it. You said something else that I think I mean some you you have these ability to drop phrases that really hit me in the heart and the head and one of them was sacrifice is habitual. Sacrifice is habitual and and I I think about m my youngest son complaining that when we go on vacation I well he's just gonna work anyway and the I like to work I like it I like getting up I like doing stuff I'm gonna be busy and for me but but I told my story most of my life I'm doing this for you I'm giving up all this stuff for you and it I think that story in my brain became a habit that that I was almost unaware of and you said yeah sacrifice is habitual isn't it like oh my gosh what am I doing what part of the game am I playing that I don't even realize I could I could switch if I was just more aware of why I do things yeah I I remember telling my wife I think it was 2010 I'm doing this for you I'm doing this for the family and she goes I didn't ask for any of this she goes that's the biggest lie you're doing it for you you know and if you watch Breaking Bad there's a moment at the towards the end where where Walter White you know says I did it because I liked it.

SPEAKER_00:

It felt good right like it was the first honest moment that he had you know in the whole show and I still haven't watched one episode it's time I think I should get on that bandwagon. It's really good that that is my favorite TV series. It's dark I I had my son watch it he'll never touch meth. It's like dude watch this he'll never touch it. But uh so I told my wife that and she just called me out and I think a lot of entrepreneurs work is a good escape. I mean it's it's not always an escape but sometimes when we're not feeling 100% we get so much positive feedback by working it it lets us be a little bit present into the work to get something done and feel accomplished to help our employees to help our customers like there's a lot of love in that and you know as we know early on in business we're willing to do anything for the business and sometimes that's the worst habit because then people just rely on us and we're the bottleneck. When I I went to Italy for a summer everyone had to grow up everyone had to mature everyone had to figure it out on their own. And then I remember going to our events and people be talking about our program and they weren't using my name anymore. And it hurt my feelings a little bit honestly I was like I shouldn't be this fickle I shouldn't be this immature but it's because this is good news. It means we're maturing it means that other people can provide the value. And what I'm really working on in my life today is I have really strict parameters. So instead of letting a project take over I just create parameters so and rules that help me to be intentional with my family with my friends. So this is like you can create traditions that that have these things happen on a regular basis. We have traditions in our family that are outside of religious traditions or outside of holiday traditions that really help us out. We have you know like uh I just have rules just like I said with with travel and stuff like that but then I have rules of like where the computer stays and never goes and when I like even at my cabin I built a special room above the garage that's the only place I work I never work in the cabin because in the cabin is family time fun time relaxation so that I so I spatially anchor my life to support what I want because it is easy to work um it's harder to be intentional with the family but when you break the habit and you start getting present with the family like I found that's why I got into comedy. When we're laughing we're present we're not worried about the past we're not concerned about the future we're in the moment and so laughter is a big part of our family. We're gonna have a little family party coming up and I know that there's gonna be ton of laughter and nobody's gonna be thinking about our differences in politics or our differences in philosophy that we're just gonna laugh and make we're gonna make fun of each other and that's uh part of what makes our family like work so well.

John Tobin:

So I I love I love the tradition thing and it's almost like you're you're creating habits to get out of your habits in a way. I mean you're creating but but I because I was going to ask you like how do you wake yourself up I mean maybe other than a significant other reminding you is there is there a trigger that you can put in your brain like oh I'm doing it again or I'm trapped again get out of it. Like is there any any anything that you do or is it these traditions that have helped you um the rules traditions however you want to frame it uh that that have helped you re reminders because I I think that that happens to me I go I go in you know uh almost did big slumps and then really really ride the wave and like going crazy and that's kind of where I am right now like really really all in on work and it's it's actually fun though but but but am I just kidding myself that it's fun? I don't know. Like maybe I I can convince myself. So I I don't know is there anything to trigger or like a a wake up in a way I will talk to my wife when things are going to go in waves and get permission.

SPEAKER_00:

I'll say like in July I'm like I'm gonna launch this program I want to test some things before I you know bring in a sales team let me know when this becomes a problem. Okay. So the first few months we're high five and celebrating we're marking off and then she's like yeah okay cool yeah I'm done and I was like all right like that was you know so I create those agreements beforehand. The other thing I do is I have these things in the calendar 30 minutes coffee and carry I like alliteration right so it's 30 minutes in the morning and then I've carved that time out and she knows once a week I might say you know what I'm in the middle of writing right now. Can we just skip coffee today? But I make sure that it's the majority of the time that we do it. Then the second thing I do is vision and visit So last night we got in the hot tub and we just talk about what's going with the kids, where we headed as a couple, what are you most excited about? And it's more visionary. We're caught carrying coffee is more like the stuff that needs to be handled. Hey, we need to set up that extra bank account, like that kind of stuff. And then we just have our weekly meeting. And that weekly meeting is we do Sunday brunch with the kids, and then her and I do a meeting afterwards. We play some records, we have some coffee, we kind of go over things. I got to tell you, we don't have to do that as much anymore. Like sometimes that meeting, she's like, we're good. Like because I have those other pieces. But during a busy time, that one weekly meeting is critical because what happens is rather than her at the end of my day, when I'm tired, I work really well in the morning. I don't work well at night. Like at night, I go to bed or I went to bed at 8:30 last night and I got up at seven this morning. I've obviously need some extra sleep and I'm cool with that. But um, she'll make fun of me for going to bed too early. Uh but when I when I'm really in that season of like flow in the business, we have to have that weekly meeting. That way I can really do a check-in. How am I doing on a scale of one to 10? You know, uh, and and just making sure that I have at least a date night or a dinner or something. So now she's getting that quality time, which is an important thing for her, even though it's just two really focused moments in the week. And then when I'm in a less busy season, I'm doing the coffee thing, we're doing the vision and visit thing. So we've got a little bit more going on. And that way I'm never completely abandoning it, right? And so I just find carving time out like I feel that if something lives in the calendar, I am really good with it. If it doesn't live in the calendar and it's an intention or to-do list, it can totally get blown off. So I make sure that I put her as a priority and I always go, remember, she's the biggest client that I have, if I'm gonna use business terms. So I need to treat her like the most important one of them all, because when it wasn't good, nothing felt fulfilling. Everything felt hollow. There was no celebration, you know? So that's the that's that's my methodology for doing it. And I just have someone in my life, she's really good at just telling me. She's like, she's not mean about it, but she'll just be like, huh. We've had a lot of conversations this week. You do all the talking, you never listen to anything I say. And this last year, she's like, I don't even know how you've become this good of a listener. I'm like, it's it's effort. Honestly, I just I've gotten good at listening. I'll call to tell her something, listen for 20 minutes, and be like, by the way, and she's like, Holy shit, I just but I realize it's because for years I haven't given her a chance to talk.

Mike Maddock:

So 23 years you've been together. Yeah. Um, couple kids. So I the the central theme of your seat at the table, and you might have already covered it, but I want to just give you a clearing to hit it if you want to. The biggest decision you've ever made. Context, what was the decision? What happened, and how how's it worked out for you?

SPEAKER_00:

The biggest decision. Because I've shared other things, I'll share that when I decided to go into finance and and have my own business, I was really in a depressed state before that because it's 1999, the economy is off the charts, I'm going to a very small school, and I'm a really good interviewer. I couldn't have I wouldn't have been great at all these jobs, but I could get any job because I could do a good job in the interview. So I got offered it to work at an investment bank. I got offered to work at the second biggest fund uh company at the time as an institutional investor, which may mainly would have had me doing things like taking big clients out to golf, and I hate golfing. It was like all these job offers, right? I would have had the biggest offer for Anderson, which wouldn't have for that my school had had, but like they were about to go through Enron in just a few years. And so I was, I was all my professors are like, these are great offers. You need to take these offers. And I remember the one place I went to interview, there was a blizzard the whole time I was there, and I'm dating my now wife, and I'm like, How do you feel about moving to Milwaukee? She goes, I think if that's where your dream is, you should move there. She didn't say I would that she would move there. She was kind of like, I don't want to be a dream. And I was like, so, and I also like my grandfather was my hero, and you know, he he had he was entrepreneur. He had a he played the accordion and played in a band, and he also had a TV repair shop, but he was a coal miner. And my dad was a coal miner. And so, like, they just felt like having your own thing because of you know, my great-grandfather was risky, and so it was really hard for them to support it, even though they wanted to. I mean, they were my first clients while I was still in college, but now when it was like, I'm gonna graduate, I'm gonna go into business, that was instrumental because if I would have taken the corporate route, I would have I would have hated life. I just I was unemployable in reality, but I would have maybe fought through it just out of survival and deciding to be an entrepreneur. I think I broke a lot of our generational chains and and false beliefs. And I remember it was 2001. Um, I got this really big check, six grand, you know, six-figure check. And I'm like, second year in the business. So I went straight to my grandfather and I shut up my bank account. And I like I could sense his relief. And he just like grabbed my shoulder, got really teary-eyed, and he was like, I'm really proud of you. And I was like, I was like, Yeah, that was so such a good and now, you know, my parents became clients, my mom worked for me for a long time, my sister works for me, my brother-in-law, like it's been a it's been a wild ride, but such a richly rewarding experience.

John Tobin:

So you say you went went to business for yourself, but it it started as selling insurance effectively, right?

SPEAKER_00:

Yeah. So I started selling insurance and then I met three other younger guys. They were all in their 30s. I was in my early 20s, and they were surprised by what I was doing. So we formed a partnership, the four of us, and uh, that was in 2001. So um, I I was still selling insurance kind of, but we were now charging fees, we were doing other stuff, we were running events, we had a monthly membership, and that was part of the issue that Guardian had eventually when we started a radio show and I started doing speaking outside of the you know, charges our clients.

John Tobin:

Yeah, that that is a decision though, like especially having all those opportunities that are just kind of a path, like a clear path. Um that what you did was not very clear, frankly.

SPEAKER_00:

And I mean, if I would have become an investment banker, it would be against most of what I stand for today, but I would have made a lot of money. I mean, investment banking is super lucrative, you know? Yeah.

unknown:

Wow.

Mike Maddock:

The um you're you remind me of a story. I started my first business right out of college as well, my first real business. And but in in college, I had all kinds of jobs. And one of them, I was a doorman at 40 East Delaware. So fast forward six, seven years, and we were doing business for Leo Burnett, big advertising agency, and their largest account, the person that ran it, called me one day. She's like, Mike, my sister needs some help. I'm like, okay. She goes, You need to call my sister. So I call her sister. We do a bunch of work for her at the logo, little tiny company. And fast forward 30 days, I get the check and I see on the check that it's 40 East Delaware. And then a light bulb goes off in my head. Like, oh my gosh. I call her up. I'm like, hey, hey, I was your doorman. And she's like, excuse me. I go, I was your doorman. I I used to hold the door for you. She's like, okay. I'm like, yeah, yeah, you just sent me a check. And like there was this moment for me where it's like, I have because I remember holding doors for people and sit behind the counter going, someday I'm gonna get to live in a building like this. So there's these moments, it's just like, yeah, she wanted a handkerchief. She thought I was a stalker or something. And all I was doing was celebrating that, you know, someone that I used to hold the door for was actually paying me for something. Yeah. These moments.

John Tobin:

That's good. My my my little moment like that is just joining the first time, well, the first country club I joined. So I was I was a caddy when I was 13. That was kind of my first job. And you're meeting all these successful people. I mean, it was uh south side of Chicago, so they were marginally successful, to be honest with you. But like to me, it was like so amazing. I'm talking to all these like professionals, and it was like, someday, someday, I'm gonna have a country club, I'm gonna belong to a country club. Yeah. And uh yeah, that was that was a big moment. It's kind of funny when you look back on some of those.

SPEAKER_00:

Now you're like, do I want to own one or just belong to one? You know?

Mike Maddock:

Well, and he's actually the nicest guy to do caddies, I'm sure, in the world because my friends that were caddies and now own businesses, you want a caddy for them because they remember what it felt like. And those those guys learn so much from just hanging out and being in those conversations, just listening to the dialogue and how people like, hey, have you heard about Bernie? Do you trust him? There's so much to be learned walking along business people um at the golf course. And they they sometime when we're having uh a beer together, remind me to tell you the story about my buddy Jeff catting for Michael Jordan. It's worth something, maybe in another podcast. Hey, um, how about some rapid fire questions, Garrett? You ready? Let's do it. Yeah. Oh, here are the rules though. The rules are you have to just like first thing that comes to your head, all right? Okay. All right. All right. One word that you can do.

SPEAKER_00:

You know, this is I know it's okay.

Mike Maddock:

It could be a sentence. I just want what the first thing that pops in your head. So one word most CEOs misunderstand about money.

SPEAKER_03:

Keeping it. Uh best money decision you ever made. One habit every financially free CEO has. Uh worst money myth entrepreneurs don't believe.

SPEAKER_00:

Money myth would be there's deep down they think there's only so much to go around.

Mike Maddock:

What's more dangerous, data or scarcity thinking?

SPEAKER_03:

Scarcity by far. By far. Okay, finally, finish the sentence. Money should give you more Options. Awesome.

Mike Maddock:

Garrett, so fun to hang out with you. Uh Garrett Gunderson is the name. I don't need to tell you how to get hold of him, because all you have to do is type his name into any kind of search tool, and you'll find him. He's everywhere. Uh, you can see his stand-up comic bin on Amazon. I watched it. It was good, Garrett. Well done. I can't believe you did that. And um just a ton of books and my favorite money muse, Garrett Gunderson. Thank you for spending time with John and I.

John Tobin:

That was amazing, Garrett. Great to meet you. And uh yeah, I could spend days with you, honestly, and and pepper you with a lot of questions, to be honest with you. Because I I I don't have what you have in terms of the thinking. I still don't. And I should, but I still don't. Even after listening long.

SPEAKER_00:

That's for sure. Like, there's nothing like writing a book and being like, I'm not fully congruent with what I'm writing about right now. Let's go through this. I love that. It's painful.

Mike Maddock:

We write books to work on ourselves, let's face it. Totally. I mean, that's what we're doing. It's total therapy. I have a book I've been trying to finish for five years, and I feel so bad about it because every time I pick up that, I'm like, I'm living a lie.

SPEAKER_00:

Yeah, wait till you see my next my next book. I don't know when I'm gonna I've had the manuscript done for two years, but it's using humor to teach finance. It's shorter, it's punchy, it's really meant for younger people because I think they'll get through it. I I'm gonna illustrate it. I'm really excited about it, but I feel like Money on Mass still has some legs that deserves a little attention to get it out there because it's it's you know, most of what we talked about today is really that Money on Mass book and what comes from there. And, you know, Mike, you've asked so many questions that it and the the vignettes that you love, it's because I wrote about it. Usually when you I can pull out vignettes because I write about it, and then it really gets me to think about it. It's not just you know as organic as it sounds sometimes.

John Tobin:

Well, I can't wait to introduce you to my kids, honestly, because I I I think um, especially my son, I think he'd really get into uh a lot of the things that you're talking about, and um I I the he could learn a lot. So amazing.

Mike Maddock:

That's the highest compliment you can get from a father, by the way. Yeah right there. Thank you. Well done, Garrett. Thank you.

SPEAKER_00:

Good to spend so much time with you this week, Mike, and good to meet you. Yeah, I mean, Garrett, thank you.

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John Tobin

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Mike Maddock

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