Comedy, Rockefellers, and Tax Secrets Used by the Ultra-Wealthy

Brad Johnson: Welcome back to another episode of Do Business. Do Life. We’ve got a return guest, a man named Garrett Gunderson. Welcome to the show, Garrett. What’s up?

Garrett Gunderson: It’s been a minute. It’s been a little bit, so it’s good to see you again, man.

Brad Johnson: Likewise. It’s the OG podcast, the Elite Advisor Blueprint, we connected, and you were like a fairly early guest on that. And then I think we went to a couple of groups together and MastermindTalks, the one I remember where we really spent the most time together, Jayson Gaignard’s. I know we’ve got a friend in him in common, and then a lot of friends in common that attend that regularly. And then just really got to know you, man. You came out, hung at the house. We hit a CrossFit workout in the morning. And so, what I love is you’ve done some cool things in finance, New York Times bestseller, built some incredible programs, but you’re just a fun hang. So, I was looking forward to this one. So, tell me what’s new in Garrett’s world lately.

Garrett Gunderson: So, I sold my business in 2021. We were doing about $10 million of revenue just in coaching and digital sales. That’s not financial transactions. So, we were doing pretty well there, but I was pretty bored with it. Because as we scaled, I didn’t really get to know any of the clients anymore. We’re doing the same event all the time. So, it was a machine, but it was called Wealth Factory, and it felt like a factory to me. So, I was like, “Yeah, I’m going to take a break. I’m going to figure something out.” And then I decided to do comedy during that break. I filmed a comedy special, April of 2021. It’s on Amazon Prime. I did two tours, 16 cities the first time, eight the second time. The whole special is around money. So, I figured I wasn’t going to be the funniest comedian, but I could be the funniest money comedian, you know what I’m saying?

Brad Johnson: Based on the dryness of financial content, you’re like, “I can crush this demographic. No problem.”

Garrett Gunderson: Even if there wasn’t any, I was like, “This is the best way to go.” And so, I did that, and that was pretty fun. And now I do a little bit of comedy. I had a friend that called me say, “You want to do comedy?” So, I put him up on stage for an event that I was a judge of. And then I did like five minutes. And it’s funny. I’m just at a part of my comedy career where they’re like, “Alright. You got to do one new minute to start the show.” I tried something way out on the edge. It definitely did not get a lot of laughs, and I was completely comfortable. And then I had my five minutes set, and three minutes into that, I go, “Let’s go back to my opener.” And I got them to laugh, which was great, by making fun of how it went.

But it’s like, dude, when I started, that would’ve just tore me up. I would’ve lost sleep about it. I would’ve felt terrible. And now the way that translates is I spoke to a couple of thousand doctors two years ago. And I had an hour and 45 minutes, and they showed my comedy trailer before I went on. So, I was like, “Well, I’m going to be out there a long time. Might as well do some comedy.” And I remember the event organizer came up and he goes, “Dude, that was amazing, but we should have given you more time.” I was like, “More time?” Like, an hour and 45 is a decent amount of time on stage, right?

Brad Johnson: Yeah.

Garrett Gunderson: He’s like, “Yeah, man, 20 minutes isn’t enough.” I was like, “Dude, I did an hour and 45 minutes?” But comedy resets people. If you tell the joke, the energy goes right back to where it was before. So, it can really keep people engaged and alert. And I’ve had times where I’ve shown up to an event. I was speaking an hour south of here, but there’s major traffic. So, the other speaker was late, and there was like a traffic accident. So, they said, “Hey, can you do two hours instead of one?” I just like, “Yeah, how much comedy can I do?” They’re like, “As much as you want,” because they’re eating dinner and dinner sucks. I hate speaking at dinners.

Round tables, noise, but if you can make fun of people, you can have a good time. And then they pay closer attention. Man, Brad, they say that people remember three times more when they’re scared or when they laugh. So, I figure I’ll let the news scare people. I’ll just make them laugh while I teach this stuff.

Brad Johnson: I love that, man. And I’m actually at one of the MastermindTalks. I think Jayson had you, right as you were putting the set together, I think you stood up and, I mean, dude, you’re funny, like it was good stuff. And so, let’s go to just one of the prior episodes we just dropped was with Nick Whitaker on our team, just coaching on how to take public presentations as an advisor and convert into appointments and hopefully clients. Dinner seminars, educational events, that’s nothing new in finance. But let’s look through the lens of standup comedy, because I think a lot of people get scared to present, but standup comedy is a whole another thing. You’re pretty vulnerable up there. You tell a joke. It doesn’t hit.

So, what are the things you learned from stand-up comedy, whether it’s winning over a room, whether it’s dealing with a heckler, that you think could apply for a financial advisor out there that’s presenting?

Garrett Gunderson: So, the night before I filled my comedy special was probably my biggest lessons ever because I was like, “Oh, certain people that aren’t going to fly in because they’re worried about COVID.” It was April of ‘21, or they just had scheduling conflicts. So, I’m like, “I’ll do a rehearsal and I’ll have people on Zoom.” And I just had the camera crew kind of seeing how I moved. It wasn’t in the main area, it was in my office, and I was tired and I was in my head. And so, I realized is, if you have a different conversation in your head than you have with the audience, you’re disconnected. And so, like at the end, my friend, Sally, I think you know her, she was like, “Hey, we’re proud of you. Tell me what you thought. How did you think to do this?”

And I told a story. And everybody’s laughing, and it’s like 10 minutes free flow. My manager pulled me aside. He goes, “That’s the guy that needs to show up tomorrow, like the guy in the beginning.” And I was like, yeah, because in the beginning, I was like, “Man, I’m tired. I don’t want to do these jokes. People are on Zoom. They don’t even have their sound on. I can’t even see them.” So, I’m having this conversation. So, the next day I was like, “Hey, I’m going to be so present that anything that comes to my head, I’m going to say out loud.” So, literally, my son yawned in the special, so I made fun of it. People laughed. I lost my place once. We started joking about it. Everybody laughed.

Like, what happens is there’s like happy accidents can actually be the funniest moments, and people want to be with you, not you trying to impress them, not you thinking about what to say. It’s when you’re in that moment. So, I just learned how to be really, really present. And so, when I’m up on stage, whether it’s a speech that I’m giving in finance or whether it’s something that I’m doing for comedy, it’s just about being in the moment. So, let’s say that I say something that’s not funny happens, or I trip up on a joke or something. I just acknowledge what is. I make fun of myself. I make fun of the crowd and say, “Oh, I didn’t realize you guys weren’t smart enough to get that joke. Let me do that one like let me do that simple.” And then they laugh.

But if you don’t acknowledge it, you get off rhythm. You feel that disconnect. You can feel the effort that comes from you. And what I find is if you can’t feel your feet, you’re not with the crowd because then you’re efforting. If you’re leaning forward too much, it’s because you’re efforting. When you can be just grounded when you can breathe, like you could get really present when you breathe, and people can be drawn in when you just breathe and take a beat. Like, pause is one of the things most advisors are scared of, but if you could just pause for a minute, people start to pay attention again. It gives them a chance to process. It just takes confidence to do it.

Brad Johnson: Yeah. It’s wild. Two things come to mind here. Number one, I’ll hit the last one, pause. I remember this was a sales training, probably a decade ago, and I remember they were talking about people that have influence, what are the common themes? And one of them was they speak slower. And it’s like, “No, they’re just pausing to actually figure out what they want to say.” But you can’t tell that on the external when it’s delivered, right? It seems prophetic when people take these long, drawn-out pauses. But to your point, if you just work that in, now, it actually gives you a chance to pause and be present in that moment. But the way it’s received on the other side, it’s like, “This dude just went to a whole another level.”

It’s wild because most people just get all like, it’s like Tommy Boy at that scene where he is like, “I just get so… And I screw up the sale.” So, I want to go back to another word you said, though. You said connection. And so, as you started to gain more confidence in your standup and you’re like willing to call yourself out and say, “Wow, I sure just messed that one up,” what did you start to learn about the audience? When you kind of had self-deprecating humor but you were able to connect in that moment instead of just glance by it and hope they didn’t catch you, what were like the learnings that came out of that?

Garrett Gunderson: Yeah. So, I was trying a new set. I had 20 minutes, and probably seven, eight minutes was new. And towards the end of the set, I kind of got off rhythm because I was looking at note cards. That’s kind of usually a disconnect, and I was kind of rehearsing. And I just felt like, “Man, this really feels long,” even though it’s like 60 seconds when the crowd’s not laughing and you’re not with them. And so, when I came off the set, I just talked to the guy I was opening for. We just had a conversation, and he was like, “Hey, dude, you just froze up. You kind of got stiff. You kind of got in your head.”

And so, I realized like saying something perfectly isn’t as important as just being connected and just saying something authentically. And a lot of times, like when you watch a lot of comedians, some of their best jokes were the unplanned jokes. That’s why people love crowd work a lot of times because it’s in the moment. It’s co-created with the crowd. So, it’s those, like I had an executive producer, Marty Callner. He won an Emmy with Seinfeld. I mean, he’s done so many of the big specials, and he is like, “I just want you to realize we always can edit, but what you want to look for is those magical moments where you do something unexpected.” So, when I film the special, I have a joke about money losing its power or not being… Like, basically comparing like money needed Viagra, something cheesy like that.

But I screwed it up. I started laughing, and then I talked about this time I took Viagra in Paris. And it was like a five-minute story. People were laughing hysterically. My wife’s in the front laughing. I was wondering if she would get mad about the whole thing. And it ended up making the special. It was just in the moment. I’ve already filmed the special, the first show. The second show was kind of like, in case there were some things that we missed, and we ended up taking a bunch of stuff from the second. But part of it was you just have to recognize like the crowd wants you to win and just be with them instead of trying to be impressive to them. Like, that’s a big difference.

I just gave a speech on Saturday. They had chairs up there, so I just sat on the chair for the first 20 minutes. I’d had a conversation with them, but then I would get in these streams where I’d get up and I’d be passionate. I’d get the applause, break, and then I’d go sit back down. Then I would pause before I’d write on the board. I’d take a deep breath, and it like draws people in. And so, I think a lot of that comes from just stage time, but I know my worst times on stage is when I was trying to be something, do something, get something, have people receive me a certain way, worried about what I was saying. It was all like this internal dialogue that wasn’t about them. And the more you make it about yourself and the less you make it about them, the more disconnected it feels.

Brad Johnson: So, a couple of things there. The crowd wants you to win. I love that. When you’re internalizing it’s about Garrett versus about them, when you make it about yourself, that’s where you’re going off track. When you’re just like, “I’m here to connect and kind of flow with them,” and you call it crowd work. Is that a comedy term of like that’s a certain type of comedy, crowd work, or can you explain what that means?

Garrett Gunderson: Yeah. So, maybe someone like says something in the crowd. I’m going to acknowledge it. See, I did this set in Vegas a long time ago, and there were three really drunk girls, and I didn’t say anything. And so, it wasn’t a good set. And my wife’s like, “Well, maybe they just weren’t a good crowd.” I’m like, “No, I wasn’t a good comedian because I didn’t address those three girls. Everybody would’ve laughed if I went after them. Nobody was there to feel bad.”

Brad Johnson: Because they were kind of disrupting the show, like for everybody.

Garrett Gunderson: And if they’re disrupting, they can’t hear the jokes, and I’m not acknowledging it, which feels weird. So, then I remember I was doing a comedy set. I was roasting Dan Martell, and there were a bunch of people there, and someone heckled me. And I don’t even know what they heckled by. Just immediately caught them in the corner of my eye, and I looked over. They had food all over their hands, and I go, “Let me guess, you’re single.” And they’re like, “He’s going through a divorce.” I’m like, “Well, let me tell you whose fault that is.” You know? And like, dude, but I mean, he heckled. And I have the stage. I have the power when I have the stage. The crowd’s on my side, not his side. And someone that’s disruptive, you could just put them in their place.

And what I think is the first thought’s the funniest. It might not be the nicest, but the first thought’s the funniest. So, I just go unfiltered with the first thing that comes to my mind if someone’s going to try to heckle. But the crowd work is sometimes like people delay their laughter, and I’m like, “Oh, it feels good. It’s like someone’s on Zoom here.” Like, I just joke about it and then everybody’s laughing. They laugh. If it’s just that someone does something silly, I’m going to be super playful. If someone does something mean, I’m going to be funny, but in a pretty direct way. I didn’t have to do it very often. But like, if you don’t, they start to take over the show. They start to disrupt the crowd.

And I remember my very first time giving a speech as a financial guy, there was someone that is in the back of the room, kind of like somewhat heckling, but he looked like a Santa Claus. So, I’m like, “Could someone tell Santa Claus to shut up?” And, dude, everyone laughed. He laughed. He came up afterwards. It got everybody on my side because I acknowledged what is. I wasn’t afraid to say what was going on.

Brad Johnson: Well, you’re hitting something, and at this stage in my career, I’ve seen hundreds of financial presentations, some with the live crowd. And you do have to have confidence. Like, at the end of the day, it is your comedy skit. It’s your seminar if you’re the advisor on stage, and I want to go back to, you said it earlier, the crowd wants you to win. Like, the crowd’s showing up for a reason. And if you let somebody else in the audience dominate it, make it about them be disruptive, you’re actually doing a disservice to the greater whole, right? So, it’s almost like you’re up there defending like, “This is for us collectively. It’s not about you.”

And so, do you just have kind of, because, trust me, there’s plenty of hecklers at financial seminars too. Do you have like pre-prepared comments that you go to? Is it always that you’ve used before that you know kind of settles things down? Is it just spur of the moment, whatever comes to your mind? Is it a combo of that? Like, if you’re an advisor back in that world, how would you think about it if that’s popping off in one of your seminars?

Garrett Gunderson: It’s spur of the moment, the first thing that comes to mind. I mean, I’ve seen what people have done that have handled hecklers, and I always keep that in the back of my mind because I could always use it, but usually, just go with the first thing that comes to mind. And there’s not a lot of them. Some of them, they’re not even hecklers. They’re just loud. They don’t recognize how loud they are. Like, when I was in Dallas, dude, people were super drunk. They were just really, really drunk. So, I was like, “Cool. Let me address this.” And I remember we kicked off our tour in Phoenix, and I was a little nervous, man. It was filled, like the Tempe Improv had a ton of people, good energy, but my opener was really flat.

And so, when I came out, I was kind of just doing my jokes, and then I finally stopped and I was like, “This is the opening night. This is pretty cool, like we’re all here. Thank you for showing up.” Like, I just had a conversation with them then went back into the jokes to crack the tension, right? To just be like, hey, they could feel that it was off, and then all of a sudden they’re with me. If I would’ve just kept going, going from joke to joke, it feels too rehearsed. It feels too inorganic. And so, again, if I’m having a different conversation in my head that I’m having with the crowd, I’m not connected. It’s that simple. If you could be present enough with them that you’re speaking to them without a separate conversation, they’re going to feel that. They’re going to feel that confidence. They’re going to feel like they’re with you.

Brad Johnson: Man, dude, I know we talked right before we hit record. I’m like, “Dude, let’s get into some of the standup. I think that’ll apply.” But this is so spot on with I’ve been in seminar rooms where the audience is not with them, but nobody’s acknowledging it. Right? And the advisor just keeps going, and it’s a dead seminar with poor results. So, I want to go back. If the conversation in your head is different than what’s going on out there, you stop. Like, you’ve learned to stop, acknowledge it. It’s almost like it’s just stream of consciousness a little bit like, “Hey, guys, like, let’s come back together here,” like a huddle almost.

Garrett Gunderson: Well, I think about MastermindTalks when I did comedy. I’ve probably been doing comedy for a year. And I was the host that night. So, the first person goes up, they’re supposed to do three minutes. Smart person, they do 20 minutes and they read their comedy set. It was probably two minutes of jokes and 18 minutes of pain. And so, when he came off the stage, I’m like, “That’s the longest three minutes of my life,” is what I told him. And he was like, he could tell it. And I got up on the stage and I said that I go, “Wow, for someone so smart, that was a pretty dumb three minutes, guys.” Like, I just acknowledged it, and then I was next.

So, I had to now cut my time down because it’s the evening. We got other stuff planned. And I had to introduce myself. So, I remember like going, “I think our next comedian’s probably the best looking guy in comedy. They say that he is a genius when it comes to finance. They call him sexy Jesus. It’s me, Garrett Gunderson,” or whatever I said, right? And people were like, “Oh my God, did the other comedian not show up?” because they didn’t know I was doing comedy. And I saw that, so I acknowledged it, made fun of it. And then I went into my set, and the set went pretty well, and then I introduced the final comedian.

But like you just have to be aware. And if someone’s scared and they don’t have confidence, they’re not aware. So, you got to get comfortable with the stage. Like, I challenge myself, like I know that my hair sometimes I would joke that I look like Jesus. So, I used to put my hair in a bun and wear a hat. I used to like my manager would say, “You have to have an opener.” I’d be like, “I’m going to Philly. I’m not going to have an opener. I’m going to Miami. I’m not going to have an opener.” And those cities were more intimidating than others because I was like, “I’m just going to challenge myself.” And I did practice every day. I did five days a week from November 2020 until April.

The night of, I did five days a week from 5:00 to 6:00 PM. I set my basement up as a comedy set. I had chairs down there. Sometimes there was a live audience. Sometimes there are people on Zoom. And, dude, if you can do Zoom comedy, you can do anything, you know? And it’s just like, if you’re going to be a good speaker, study the craft. Do the work because then you’ll have the confidence, and it’ll be natural. If you don’t do the work, you’re going to feel uneasy. The crowd’s going to feel uneasy, and you’re going to be frustrated with your result.

Brad Johnson: Let’s go to Zoom versus live, because a lot of advisors are facing that right now, where, I mean, a lot of advisors are doing appointments just like how we’re recording this right now. What’d you have to change in a Zoom presentation versus the live to keep the energy up?

Garrett Gunderson: So, look, a Zoom webinar is pretty easy, I think. I do a lot of webinars, and so what I do in Zoom is I script my opening and my closings. And I read it, but you can’t tell I’m reading it. And what that does is it creates the right frame that then I can do the content in the middle, and I could be a little bit more at ease. But what I’ve done is I’ve created predictability with what I’m saying, how I’m setting it up. Because if I don’t, it’s easy to have that hour. If I’m doing an hour Zoom, it’s easy to get off track. So, I’m really clear about like making us promise about why to attend, what the old way is versus the new way. Like, I just really have that frame, and then I’m pretty loose with my bullet points when it comes to the main content, but now I have everybody engaged and they’re paying attention, and I just bring energy to it.

I definitely just bring energy to the Zoom meeting. When I was doing Zoom comedy, that’s brutal because you can’t hear them laugh like you’re talking, and they’re laughing, and it doesn’t really translate. So, what I found was if I had at least a few people live, I remember my manager watching a Zoom, and he couldn’t see the people that were live because the camera’s on me and they’re sitting all around. And he’s like, “Dude, how did you get that timing down like that?” And I was like, “Oh, I had people there in person.” He just thought I was like the best ever. It’s just because I had that live energy of someone in person.

Brad Johnson: So, it’s like the litmus test because you’ve got to wait for a joke, the punchline to hit. You can’t just go straight into the next one. So, having that live audience kind of helped you for the virtual audience as well.

Garrett Gunderson: Right. Because Zoom has that delay sometimes. Or if I’m talking, I can’t hear your laughter , you know? But if you can get Zoom timing down, then on-stage timing is just so easy.

Brad Johnson: Well, you hit something that is spot on. People, humans, primacy and recency. Remember, the first thing, the last thing. So, it’s cool that you tied that into your Zoom presentations. It’s like, “I’m going to script the open, so I know it’s good. The close is good. And then I’ll kind of freestyle a little bit in the middle with my bullets.” You said something to the effect of you make sure the energy, you keep it high on a virtual presentation. Are there tricks to that? Is it voice inflection? Is it you’re standing up? Is it hand motions? What are the ingredients to keeping the emotions high or the energy high?

Garrett Gunderson: I like talking about the topic anyway, so I can’t help myself. It’s like, if anything, I have to remind myself, and I just joke. I’ll be like, “Hey, I might sound pissed. I’m just passionate,” so I make a little joke about it, and then I just get into it. It’s just like who I am. I don’t really have a trick to it. But it keeps me engaged. It keeps me excited. When I’m doing videos, sometimes I try to make it more like I’m just talking to someone in the green room instead of having that voice that sounds like a presenter. And that’s harder for me because it’s just, yeah, I like to bring that energy. So, that’s where the skills more is like, how do I just make it more laid back sometimes?

Brad Johnson: Well, before we get off the comedy topic, I’m just curious because I’ve known you for a while, and I don’t have a lot of friends that have a prime special that people can literally go out and stream right now if they choose to. So, we’ll put it in the show notes. So, the official title is the American Ream. Not dream. Ream. How does one go about getting a streaming comedy special on a big service like Prime? Like, how did you go about doing that? Was there a business model in your mind? Was it just like, “I had some good connections that hooked me up”? How’s that work?

Garrett Gunderson: In 2014, I wrote down that I wanted to do stand-up comedy at MastermindTalks, and we mailed those letters. And it was like a year later that said, “Do standup comedy.” So, I went to Italy, came back, and made my wife laugh at a baseball game. I’d had the whole summer to think about like, “Hey, what do I do?” I have this downtime. I had more time to think about hobbies and stuff. I’m like, “It’d be fun to do comedy.” And when she said I was kind of funny, I translated that to comedic god. That’s what I heard in my head. And then my buddy, Keith, introduced…

Brad Johnson: Hey, dude, if you can get from your wife you’re kind of funny, I’m telling you, like my wife, she’s like all of my jokes suck. So, I think that’s actually impressive.

Garrett Gunderson: So, I was like, then I spoke at an event that Sunday, and the guy introduced me, Keith Yackey, kept saying, “Our next speaker’s hilarious.” So, I told some jokes. They laughed. And so, I immediately called my buddy, who was a runner-up on Last Comic Standing, and I was like, “Hey, can you be at my office tomorrow? I have some ideas. I look like Jesus. I just don’t have his powers, is kind of the premise.” And I wrote four minutes and 20 seconds of comedy bit. Did it. He’s like, “This is really good. You should open for us.” And so, I just started to open for him and my buddy that I went to high school with, and they had a lot of sets. And so, I just got a lot of stage time.

And then when they filmed their comedy special in 2019, Barry Katz was there, who was a manager for Chappelle for eight years, or Louis C.K. way back in the day, or Bill Burr. Like, he managed Dane Cook, a bunch of people, the names that you know, and he just thought I had a good set, and I did. It was in the round. It definitely was one of my better sets. You might’ve seen that. I think we passed around MastermindTalks. It’s the one that was really well filmed. And so, Barry’s like, “Hey, I think you’ve got something here. Nobody could really do what you’re doing financially in the comedy world.” And so, he’s like, “I feel it in my bones that you’ve got what it takes.”

So, hired him and took me like a year of telling myself I could be a comedian, and meeting with one of Chris Rock’s writers and having him work through some things with me. And then finally, I was like, “All right, let’s do it.” In November of 2020, I was like, “Let’s do it.” We did it April 15th. It was like, I just said, “Let’s do it,” on tax day. That was pretty quick, but it took a long time to get on a streaming platform. I just kept asking everyone I knew, like, “Hey, who do you know?” I spoke at a family office event with 20 billionaires. There was someone in there in film production, met with them. I met with another financial guy that actually had a connection, and he’s like, “Yeah,” because he lived in LA. He’s like, “I got a connection,” and that’s the guy that got it.

I just kept asking everyone for years, “Hey, who do you know? Who do you know? Who do you know?” Getting a ton of nos. Like, Barry gave it to everything. HBO Max watched it six times and said no. Netflix watched it three times and said no, because they each had their unique tracking links. Comedy Central said… Everybody said no, because I had no social media presence. I was unknown. And they liked it enough that they’re like, “Yeah, we would consider it, but it’s too big of a risk for us.” And then finally, this firm, Multicom, said, “Yeah, we can get it on Tubi, Roku, and Amazon Prime.” And so, that was super exciting. Not profitable necessarily. More like a good way to spend money and a great hobby than it was.

I mean, I got paid, I think, five speaking gigs at $25,000 a piece doing comedy. And then I would fill these comedy venues, but they were like $75 a ticket. Sometimes it was friends I’m giving tickets to. We just didn’t make a lot of money doing it. It was just kind of a fun experience.

Brad Johnson: Well, I always look at just life in general and think about who you were before and who you are now. And I can promise you the skills you’ve developed, just being able to, the confidence to walk in front of a crowd, get heckled, throw some jokes out there that didn’t land. Like, you’ve grown tremendously, I’m sure, through that. But I’ll tell you the other lesson I take from it. You wrote it down on a piece of paper. You hear it all the time. Have a vision in business, have goals, have champagne moments, whatever you want to title them. But you declared it, and then you kept at it. Like, you didn’t just give up once.

You’re like in a room, “Hey, anybody have this connection? That connection?” And I’m going to say that’s pretty inspiring just in general in life to those listening. It’s like, if you want something, go declare it and go get it. Like, don’t just talk about it and bitch that it never happened. And I just love that about you. You’ve always kind of done that in all different aspects, whether it was… Dude, did you set out to become a New York Times bestseller? Did it kind of accidentally happen, and you wrote a book?

Garrett Gunderson: No, I announced in front of a room that I want to be a New York Times bestseller when I wrote Killing Sacred Cows. I got the self-published version in my hands. I was hosting the event with 85 people. I said, “I want to make this New York Times bestseller.” I told the crowd, someone came up and they said, “If you’re serious about it, I’ll help you. I’ll find the team that can help you.” And he did. And so, yeah, I declared it. It was definitely something I wanted to do.

Brad Johnson: So, there’s a theme here I’m seeing, Garrett. You’re making these big declarations that many people would be like, well, no way that’s going to happen. So, you almost don’t limit what your dreams are, but secondarily, when you’re in these rooms, you are seeking out others that can help you get there. So, it’s kind of the Jim Rohn, you’re the average of the five people you surround yourself with. Is that a natural thing that you do? Did you have to learn to do that? Like, how did you learn to seek out these different coaches, advisors that can help you get where you want to go faster?

Garrett Gunderson: I just have friends that are more successful than I am. So, that’s helpful. It’s harmful to a degree because I’m susceptible to jealousy sometimes and it annoys me because I just do things that are very creative, artistic, and if I just would stick to some of the business things that I should do, I’d have a lot more money. But at the same time, I live in the house I want, have the cabin I want. So, I have to remind myself of those things. So, that’s what, when they say it’s like the five people you surround yourself with, well, five people I surround myself with a lot are worth hundreds of millions. I’m not there yet. So, the good news is they show me away. The bad news is I judge myself for not being there sometimes. And I think about the mistakes I’ve made that prevented it from happening and all that kind of stuff.

But at the same time, I think that quality of life is what matters and wealth is our ability to be present. And if I was making a lot of money, which I’ve done before and not enjoying what I do, I’m not fulfilled. Like, I had seven figures coming in from my other firm, whether I really did anything or not. It was recurring revenue. It was a licensing deal. And it didn’t make me happy because I was just like, I don’t feel any level of value creation. I don’t feel like it’s on brand. So, it’s really painful to separate and sell that business.

But now, I’m creating a business with new rules. The rules are, I get to work with people I love. I get to do the things I love, even if they’re not the most scalable thing if it helps me feel connected. I get to live by my values and say no to things that don’t align with them. And so, it’s like, it’s interesting because some of those businesses are really starting to take off, like this week has been a record week. We put more people in our multiplier program, which is my financial community, where I teach every single week on either make more money, keep your money, grow your money, or grow yourself. And then we have one-on-one coaches that help them get their financial house in order. And then we have a network of attorneys, accountants, and investment advisors that we don’t own the businesses, but we vet them. And dude, that thing’s really growing right now. And I’m starting to get really amazing connections. I’m still trying to figure out media. I used to run a radio show five days a week, two hours a day.

Brad Johnson: Dude, what haven’t you done? You’re like a Renaissance man.

Garrett Gunderson: I burned myself out, though, dude. Five days a week, two hours a day of radio was before podcasting. And we even started building a following, but I just got tired about doing this every day. And then podcasts came out and I took 10 years off. So, that was just bad timing. And even I was just so anti-social media and now, I’m really going, hey, I see the merit and value of it. And so, I’m a little late to the game on some of those things and trying to figure that out. And it’s interesting and fascinating and frustrating all at the same time as I try to discover, because I’ve sold a lot of books. Rockefellers has sold hundreds of thousands of copies, so that thing’s done really well. And it’s never hit a list because it’s self-published.

But there’s financial advisors that buy it every day and they sell boatloads of insurance. I just heard of two guys this week that are both rookie New York Life agents that did seven figures of commission their first year just handing the book out. Like, that’s the kind of stories I’m going. I should probably start selling insurance being that I’ve sold more insurance than probably anyone through my books.

Brad Johnson: Well, it’s wild. I mean, some people don’t know this about you. You actually start as a financial advisor, right? Was that your first official job? Because it sounds like we’ve got radio hosts sprinkled in there, comedian, but was financial advisor your very first job straight out of college?

Garrett Gunderson: I was in college 19, got an internship with Guardian, peddling life insurance and mutual funds. And then when I graduated, it was my full-time thing and I did a lot of one-on-ones. Until 2005, we started to build this thing called the Producer Revolution, where we would give a daily email, which was called the Producer Perspective at actual CD once a month that we’d mail out with a physical newsletter.

Brad Johnson: You were ahead of the game.

Garrett Gunderson: Yeah, we hosted these events once a month that we’re in person and that really took off. And then my two business partners died in a plane crash. We had a little plane. And so, that kind of changed that. And I created a program called Freedom Fast Track, which was more comprehensive. People would pay a down payment and then they’d pay $2,000 a month and we would be comprehensive financial services. They’d have four types of coaches, a business strategist, a financial architect, a results facilitator, and a wealth engineer, which was more on their personal side. Like, what are their preferences? What is their quality of life? What is their money mindset?

And then we’d just had a financial network and that just hit a place where it was hard to grow because as soon as we hit 105 people in that program, it would break down because we’d need more attorneys, we’d need more accountants, we’d need more investment advisors. And it’s hard to find people that share our values and that were as good at education as the original network. because we had people that were amazing attorneys, but they were amazing at presenting, which that was super helpful because then they could be engaging. And so, yeah, we built a business off of that.

I bought another business in 2014 that was really good at digital marketing and selling online financial programs. And then that became Wealth Factory that I sold. And now, multiplier is kind of the main thing I’m building. But the thing I’m excited to tell advisors about is I’ve been licensing my What Would the Rockefellers Do book to financial advisors. So, we write a foreword for them. So, now, their names on the cover of the book. And then there’s two QR codes in the book. One for people to download a legacy builder toolkit, which is basically how to create a family constitution, which is a preamble to your trust. And it’s like, encapsulates the values of the family, the signposts you want for future generations and the philosophies that would help guide what happens for generations to come, family retreat, how do you invest in your heirs? How do you have great traditions along the way? And then also, just like the building blocks of the basic estate plan and what it looks like to pay your kids and maybe put insurance on them. So, you can use the Rockefeller method that passes wealth from generation to generation and keeps replenishing the trust.

And so, that second QR code is they book appointments. They book appointments with the advisors. The QR codes point to the advisor and it becomes an amazing referral tool. It becomes an amazing business tool. So, a lot of people just give it to their existing clients and they sell a boat mode of their life insurance because now they’re going, yeah, I should get insurance on my spouse and on my kids. And if they’re older on their grandkids because every time someone dies, it replenishes the trust. And it gives them permission to spend more of their assets knowing that death benefit’s going to come in.

And then it kind of, like, look, a lot of this is a philosophy that came out in 1947 from corporations, even though the Rockefellers came out with it before, and it was called non-qualified deferred comp. So, corporations used to say, like GE, they were like, hey, we want to become number one or number two in every category, but we’re not number one and number two in every category because some of our competitors have better talent. So, we’re going to have to recruit that talent away from them if we’re going to be number one or number two. And when they would recruit that person, they’d say, if you work with us for at least seven years, we’ll give you a pension. And now, they would get a vice president over an entire division, but as soon as that person came on, they bought whole life insurance. They used the cash value to supplement the pension, depending on how long the person lived. And then when the person died, it would replenish 100% of what they spent, plus a positive return. And then the corporation was going to be along around longer than the individual.

Well, Wall Street came in and they’re like, this is crazy. Whole life’s anemic. It’s just doesn’t get that much interest. And why would you sit here and do this? So, they convinced companies like GE to put their money in the stock market and say, hey, let’s just say the market does 10%. This is the 90s, especially when they’re making these convincing stories. Like, conservatively, it’ll be 10%. Let’s say you pay out 6% or 8%, you get that spread and you’re going to be able to take that money and have it for the company and have it for executive bonuses and all this kind of stuff. Well, they didn’t really consider disinvesting. They didn’t consider that sometimes they’d have to pay a pension on a year the market was down and it would start to pull out that capital. And ultimately, that was one of the big demises of the pension is volatile markets, especially from 2000 to 2002 being three negative years, or 2008 to 2010, so many of them went bankrupt because they abandoned the Rockefeller method inside corporations.

So, the Rockefellers go, hey, we can’t control what every person in our family does. Are they going to be able to grow the wealth or will they actually spend the wealth even though they have incentive-based trusts that they don’t just get the money, they have to be doing productive things in society, but interest rates can change, taxes can change, inflation might come in. So, they basically put insurance on every single family member, and then when that person dies, it replenishes the trust. So, regardless of what happens, they continue to preserve wealth and protect it and perpetuate it for almost seven generations now, where the Vanderbilts didn’t have this methodology, a) the Vanderbilts didn’t use trust planning. So, a trust is really critical.

And the second thing is they didn’t use insurance. And so, within 54 years of William Henry’s death, which was the eldest son of Cornelius, the first Vanderbilt died broke. And by the way, Cornelius handed most of his wealth to William Henry, who doubled their estate nine years before he died. And it was the last time that estate grew. So, there’s just this methodology and I’m like, hey, so advisors that want to sell more life insurance as a part of their portfolio, and Brad, I just look at it as an asset allocation decision. Fixed income. It’s not going to compete with investments. Investments are going to outperform cash value. That’s just what it’s going to do. But fixed income like CDs, money markets, bonds, treasuries, munis, like no capital depreciation. And if you’re with a mutual company, it’s outperformed bonds in any 30-year period of time, even after the cost of insurance. So, I’m like, this is kind of a no-brainer for someone to be able to round that out in their portfolio.

Brad Johnson: Well, I mean, you’re preaching in the choir here a bit. I grew up on the insurance side of finance. Yeah, these tools exist for a reason. And I look at the kind of the term fiduciary that gets thrown around loosely these days. But my definition of fiduciary is have all the financial tools in the toolbox and then select the best one to get the job done. And you kind of did it very eloquently there as far as, what are the pros and cons of market-based returns? Yeah. Greater return potential, but greater risk, greater volatility. And sometimes, when you’re dependent on that income stream, less volatility is actually what you need. So, I love that.

Garrett Gunderson: Yeah, here’s what’s fascinating. If you can have a two-and-a-half-year distribution diversification, so if there’s a two-and-a-half-year period where you don’t have to take from your variable accounts like the market, you can take 33% more in retirement. So, if you could just pull from cash value for two and a half years, allowing down years of the market to recover, you have 33% more cash flow from that asset because you don’t start to deplete it. So, distribution/diversification is essential and the death benefit becomes a permission slip to spend more money knowing that it’s going to be replenished into the trust rather than just live off the interest. So, those are pretty, we’re talking 20%, 30%, sometimes 50% more cashflow in the future because you have coordinated assets essentially. And so, look, I put together GarrettGunderson.com/Brad where people could just get a free copy of What Would the Rockefellers Do. So, they could just download the book.

Brad Johnson: Look at you just throwing gifts out to the audience. I didn’t even know you were going to do that. Thank you.

Garrett Gunderson: Yeah, and by the way, if they’ve read the book in the past, I updated it in 2023 just because interest rates have changed and just because I added new dimensions of, from research of these components of family constitution, family retreat, and even the family office concept of how that trifecta really helps support the trust and the insurance. And so, I think that’s really useful and helpful and probably good conversational points for anybody that’s meeting with clients.

Brad Johnson: I want to hit on something. I was looking for the book. I couldn’t remember the name. It was actually written by, I think, Vanderbilt’s either great grandson or great, great grandson. It’s called the Fortune’s Children, but it basically shares the story of, I think by the third generation, all of their wealth was gone, like after the, was it the Gilded Age where everybody’s just building these monster mansions?

Garrett Gunderson: They built 10 in Manhattan that they don’t own any of. They own The Breakers in Rhode Island. They don’t own that anymore. They own the Biltmore Estates that’s gone.

Brad Johnson: The Biltmore, that’s still on my list to go see. That’s actually what they took.

Garrett Gunderson: I’m supposed to go speak there in October. They invited me to speak on the Rockefeller-Vanderbilt story. We’ll see. I get…

Brad Johnson: Hey, hook your buoy up. Let me know.

Garrett Gunderson: It’s a real estate event. Bring you out, man. We’ll go hang. It’s pretty crazy. They had more money than US Treasury. The Vanderbilts did at one time. That’s how wealthy they were, but they had no infrastructure to preserve, protect, or perpetuate it. And they really just created wealthy socialites other than William Henry. And like Gloria Vanderbilt is a Vanderbilt and she inherited some money, but Anderson Cooper didn’t. He had to fake press credentials just to get into the job that he has. And he has a very mixed emotion about the Vanderbilt fortune. And when you look at it, it’s pretty negative because of what happened without the right infrastructure. Like, I don’t want my kids to get some inheritance. I want them to have a heritage. I want them to have an opportunity fund. Not something that prevents them from being productive or understanding what they’re capable of.

But at the same time, I don’t want my grandkids to ever have to finance at a bank. I’d love for them just to, the trust is filled with death benefit, cash value then, that cash is in there. We don’t have to even invest in the market. We can just be like, great, we’ll finance the house, so the preferred rate. You don’t have to jump through quite as many hoops. We’ve got the collateral behind it. And then, we could take small pieces of money and invest in your education and incentivize good behavior. And you don’t have to get money from the trust, but you can. And like, let’s create really cool traditions and let’s fund really good retreats, but let’s not fund laziness. Let’s not fund lack of purpose.

Brad Johnson: I want to go down that rabbit hole because there’s a couple ideas swirling here. Number one is we just had two stories play out there. You had the Rockefellers, you had the Vanderbilts. Both had the– was it even at the time, even more money than like equivalent of what Elon Musk has today? I believe. I believe proportionately, like time value of money.

Garrett Gunderson: When you look at GDP, when you look at the percentage of GDP, it’s pretty big.

Brad Johnson: So, you have these two stories play out, and from the book Fortune’s Children, one of the things I remember, he just goes into, like, they were just throwing rages like in the 1800s, 1920s, 30s, and just blowing all this money. They didn’t earn it, they were just gifted it. There were no requirements to steward it. And we’ve all seen that. Like I remember the kids that had their parents’ credit card in college, like, that money spends differently than money you had to work for. And so, I think it’s human nature, if you’re just blessed with too much money, you typically don’t do very wise things with it. You have a friend, Rich Christensen, that wrote a book that really impacted me as a parent, Toes Turn Purple. And one of the things, very successful businessman, five sons. Is it five?

Garrett Gunderson: Yeah, five.

Brad Johnson: Yeah, five sons. And he had almost this coming-of- age ritual. I know you guys have done some joint work and you– I think you called it like a family constitution. Is that what?

Garrett Gunderson: That’s my term, family constitution. His book’s about family retreat. How do you invest in your heirs? What do you do when they turn 6, 8, 10, 12, 14, 16? I mean, it is a brilliant road map and he’s raised amazing kids, so he’s proven it out, not just in philosophy, but in practicality. And he’s been a huge influence for me to have my family mission statement, to have my family guidance, to create certain traditions, like he’s been the one that’s ushered that in. The family constitution, I would say that Andrew Howe was really instrumental in that initial philosophy. He had a book entrusted that I loved, and he’s been my attorney for 20 years. And he is like, hey, what if there was a letter of wishes or a statement of purpose that you began your trust with? And I just like to call things my own verbiage and I was like, what if we had, call it a family constitution? And then the trustees use that as a guideline for how to do things because, look, if you’re so rigid, things are going to change in 10 years, 20 years, 30 years. And it might not be valid. It might actually be detrimental. So, I’m like, what are the signposts? What are the philosophies? What are the guardrails? What are the ideas that my family can understand who I am, what I stood for, and what I hope to contribute to them so they don’t have to make all the same mistakes?

And I just had a client in town on Friday. And she built this beautiful family constitution, family crest, because I do these one-on-one deep dives. And she took it back, called her son. He got emotional. She got emotional. Read it to her husband. And it was like, it’s just a beautiful, like, the whole notion was we’re here for a hand-up, not a handout. We’re here to help you with a good start. Not to prevent you from getting where you want to go because we are over– like, it was just this beautiful like, and it will be the beginning of their trust. And so, now, it’ll be part of their family and she’s going to host family retreats and then have fun games and traditions, but then have deep conversations. And these are the things that you don’t have to be wealthy to do. You just have to be loving. You just have to take the time to do it.

Brad Johnson: Well. And let’s apply this to the world of finance. I mean, there’s a lot of advisors out there. Obviously, the typical path is I want to work with people that have more money because there’s more opportunity to help them, obviously, typically, more complex plans and the revenue is typically greater. But I think a lot of people, like the financial planning experience, especially when you get into wills, trusts, estate planning, it’s very sterile, it’s very lawyer-esque where everything’s straight over their head and it’s hard to connect with. So, it sounds like one of the things, like if you were going to give an advisor advice and they were working with 5 mil, 10 mil, 20 mil sort of clients, you would take the approach of more conversational, like, what do you want? Like, what’s important to you? What sort of rituals? What do you want your grandkids to remember these core statements before you’re even getting to the trust or estate planning side of it? How would that work if you were an advisor?

Garrett Gunderson: So, for me, someone pays 35 grand to spend the day with me and then I build their team for them. I don’t do one-on-one meetings. I do one-to-many with Zoom. I do this kind of stuff. The only time I do one-on-one is twice a month. And it’s just because I like to be that connected. But if it was just getting their financial house in order, I referred out couple things. Number one, legacy leads to a bigger client. It just does. It’s a different context and shift in the conversation. So, What Would the Rockefellers Do has helped advisors upgrade the level and caliber of person they work with?

When Renee came in, we sat down and we talked about her finances, where she had exposure, where she had risks, what she wanted. And I just like, well, you have term insurance that’s going to go away. What if we made that permanent? What would that mean as far as being able to spend more money along your lifetime? And then we got into the legacy planning of family constitution, family crest, we designed it. And I didn’t get into any of the details. I just referred all the details out. And then now, she gets to talk about whether she’s doing premium finance or split dollar or like, I’m not getting into those weeds. I’ve just created the context that she’s going, yes, this is a plan that I want. And I get there by asking questions to discover what matters most to her, and then making the connections to make those a reality. It’s that simple.

And the thing is, when I have a whole day with someone, I get to ask them a ton of questions. I get to know them. I get to know what’s important to them. I’m not rushed at all. And like, I have one tomorrow, and this is the third time I’ve met with them. Their business is growing 40% month after month. So, they just have growing pains and I’m there to kind of help out. And this is the first one where we’re really focused on their personal finances, not their business, but I just do those deep dives twice a month. That’s 24 a year. And then I just refer that out to advisors who are really capable.

Now, what would the Rockefellers do? We provide leads to advisors, like, I’ve provided 150,000 insurance leads since 2015. That’s how many insurance leads we provided by that book? That’s just to our people. Now, I’ve got advisors using it, generating their own leads, using the exact system that I built. I’m here to help change conversations. The conversation of insurance is boring and mundane, and we have fewer people have insurance now than 50 years ago, yet the population has grown in the United States, or it’s almost equal number of policies, but not equal number of people is, because people don’t want to talk about it. But if you talk about legacy, you talk about Rockefellers, you talk about Vanderbilts, that’s something that engages someone that then has them think about legacy, which insurance is a part of that plan. And so, it’s how you lead the conversation, the context you set that gives you a much more connected conversation.

Brad Johnson: You are an entrepreneur. You have a lot of entrepreneurial friends. We’re talking about some of the conversations you’re having with entrepreneurs. If you were an advisor out there that wanted to ratchet up and say, hey, I want to work with more business owners that have higher net worth and obviously, hopefully, big exit someday, which is more assets to work with, what would you change in the conversation?

Garrett Gunderson: I just lead with tax. I just lead with tax, because if they’re successful, they’re overpaying tax, and so, I can immediately find money, I can immediately show them improvement, I can immediately build rapport. We’ve been doing tax as a lead since 2004. You find that more and more now these days than it was back then. But yeah, if you get really good at tax, like I’ve had people come in and we save them $3 million in one of these one-on-ones, they’re just ecstatic the rest of the day, right? And it’s like, it’s not that hard of work. It’s just that most accountants file 800 to 1,000 returns a year, so they’re not focused on strategy. They’re commoditized into filing. And so, they’re more historians than strategists.

I’m not a CPA, I’m not an enrolled agent, but I know the strategies and can talk about them in general. And then I find the firms that can help with the implementation so that it’s not just information, it’s implementation. And so, I just lead with tax. It’s that simple.

Brad Johnson: And you’re right. I have seen that become more and more of a trend, especially as the net worth goes up. And I would say, I don’t know an exception to the rule of any of the members of Triad that are starting to elevate in the 5, 10, 20 million sort of clientele that aren’t. If they’re not leading with taxes, it is definitely one of the first two or three topics they’re hitting every time.

Garrett Gunderson: Yeah, we have an entire tax funnel for our licensees, our tax navigator and entire funnel, so that if they’re going for that, yeah, Rockefeller is the main one, but then we have tax as the secondary one in the entire system because that’s what’s going to get you those clients.

Brad Johnson: What are some of your favorites? I’m compliance suitability, don’t worry. I’ll put the disclaimer out there. We’re not going to get into tax advice on this. But if you were presenting at a public seminar and you had one or two big tax ideas that almost always are going to perk up an entrepreneur’s ears, what sort of high-level topics would you be discussing?

Garrett Gunderson: You give me five minutes on this, I’ll give you a framework.

Brad Johnson: Yeah, yeah, go for it.

Garrett Gunderson: I don’t know we’re out of time. I’m enjoying it, so…

Brad Johnson: Hey, yeah, run with it.

Garrett Gunderson: So, look, I always teach this framework that there’s three buckets. The first bucket is the team, the second bucket is the deductions, the third bucket is the classification of income. The third bucket is where most of the strategy comes from. The first bucket is, hey, if entrepreneurs don’t get timely data because they don’t have a bookkeeper, a controller, or a CFO, they’re going to overpay tax. So, we’ve got to have timely data.

The second thing is we need a strategist, not a historian, and a strategist is going to proactively navigate deductions. The third thing is we need an attorney. If they haven’t cracked a million of revenue, that could be a corporate attorney. If they’re more than a million in revenue, it’s probably a tax attorney. And the fourth person is, if they own a commercial building, they need a cost segregation engineer. So, that’s the team.

The deductions, it’s really simple. I just go, hey, when you spend money, I want you to go, could this relate to my business? If you know it does, you just document it. If you’re not sure, you have a quarterly meeting with your tax team and say, in what cases could I write this off? Or what percentage can I write off? There’s a lot of things I get to write off because I have a conversation that isn’t just a no-brainer.

I bought a Can-Am. Well, the Can-Am is mostly used when people come to my one-on-ones. We go to the cabin, we take a drive in the Can-Am. So, I write off 50% of it because it’s the beginning of my podcast. It’s in the footage. But I can’t write it off all because sometimes I just take my family out for it, even though I’ve got all of them as employees. Second thing is I take trips sometimes. I’m like, hey, we’re going to make sure to do corporate compliance on this trip, so we’re going to write off 40% of the Italy trip. Like, those are why you want to have those conversations.

Now, a lot of things that people miss on deductions is, like, we now have R&D back in a big way. So, R&D in the new big beautiful bill, people can go back and amend. And if they’ve been spending time on tech and different things like that, they can get credits. 199A, that qualified business deduction, that can give them a 20% deduction, especially if they have W2 employees. That’s something people miss quite often. 132(j), if you have employees, like, I think every entrepreneur should have a company that’s just them and their family, and that company has some income flow through it and they can abuse that company for tax purposes. They don’t have partners, they don’t have anyone to report to. Like, I’m an intellectual property company. My iPhone’s 10% of it. My kids are employed by it. And guess what? We use 132(j), which says they can write off all the maintenance to my pool, my hot tub, my cold plunge, and my gym. And that’s because all my employees are available to use it. Guess what? That company is, all my employees are my family.

Brad Johnson: Hey, those are nice perks for that company, by the way.

Garrett Gunderson: Yeah. So, 280G, you get to write off your home 14 days a year. So, I always make sure, like if I have an event here, I’ve had events at my house.

Brad Johnson: Is that also known as the Augusta Rule?

Garrett Gunderson: Yeah, 14 days. Deductions are helpful, but they’re not the most important thing. I think the most important thing is the third category. The third category is reclassification of income. So, the first thing is we want active income to be passive for tax purposes, if we can. Number two, we want ordinary income to become capital gains, if at all possible. Number three, we want to employ tax-free strategies. And number four, we want to look at tax arbitrage. So, let me give number one. Anyone that is the only owner of their business, they can take a salary plus distributions, especially in an S-corp. They’ll avoid self-employment tax on the distribution. If they own a building, they can charge themselves the highest possible rent based upon comparables that come in 1099 versus W2. That’s more tax efficient.

Ordinary income to capital gains, I mean, if someone’s doing business internationally, they can do an international sales corp, an IC-DISC. Everything comes to that, capital gains, not ordinary income. So, that would be an example. More risky is an 831(b), a captive just because they’ve been abused, but you can put money in pre-tax. If you don’t have a claim, you get to pull it out, capital gain. I just think it better be a feasibility study. You better not put insurance in there. There’s just too many people that abuse those. And if one person gets audited with a firm, everybody gets audited.

The third thing is tax free. This is an important one, section 1202. If someone’s a C-corporation and they’ve been around for at least five years and they’re a qualified company, they get to sell for $10 million per partner tax free. Guess what? That’s $20 million if you have a grantor defective trust in there as one owner and then yourself. So, that’s $20 million of tax-free income upon sale with section 1202. There’s also charitable trust, right? If they have highly appreciated capital gain assets, they can donate it, sell it, not pay tax, get a partial tax deduction, take a lifetime income. And then finally tax arbitrage, you spend a dollar, you get more than a dollar back. These are ones that can be done right and they could be done wrong.

There’s a lot of people that do conservation easements. They get in trouble. Why? Because it’s in a syndication. They’re with a bunch of other people they don’t know. They have to follow a lot of rules. But if you own, like I have two friends that I’ve seen this last year, one has 10 acres. Well, they have three one-acre plots in one zone. They have another two-acre plot on another zone, and then five acres for their main house. I’m like, we’ll see if you can split up that two acre to two one-acres and then you can just conservation easement of anything that you’re not going to build on, and then all of a sudden, you get to give up the development rights, that’s going to be clean. If it was like, hey, Brad and I and a hundred other people we don’t know are going to put money into something that’s supposed to be a conservation easement, guess what? You’re going to get audited. You’re going to lose.

Another one is I buy art. I buy art from an art investor and I put it up at my house. I just put it up in July. It’s going to be hard, willing to donate. We love this art. It’s just like, I look at it every day, but when I’ve owned it for three years, it goes from book value to appraised value because the art world, the United States, is based upon donation. In Europe, it’s based upon purchase. So, what you find is a lot of people donate art in the United States because they get major tax deductions. I’ve been doing it since 2006. Because when I bought my first collection, I started donating in 2010 and ultimately, I’ve got back $2 for every dollar I spent. That’s tax arbitrage. Don’t let the tax…

Brad Johnson: So, let’s dive into that one. That one’s interesting. So, here’s this art I love. I want it in my home. So, you’re using it for– is there a time period? Did you say three years that you use it?

Garrett Gunderson: Three years to go from book value to appraised value. But here’s the trick, you’ve got to be able to buy the art in a way that it’s deeply discounted when you buy it. Meaning, I’m buying art collections. So, the artist is going to sell at a discount, plus I’m also not selling out in the open market. They know I’m donating in three years. That donation actually helps their art value. If I sell it on the open market, it would be detrimental to their art value. So, I’ve given them a really good reason to sell the art to me in mass, like in a big collection.

Brad Johnson: Interesting. And you’re donating it to a museum or what?

Garrett Gunderson: Yep, museums.

Brad Johnson: So, you donate this art to a museum and it goes to appraised value, which is typically going to be on the higher end. And so, now, for that artist, it helps them because their art that they’re hopefully still selling just bumped up to a higher market value.

Garrett Gunderson: Correct.

Brad Johnson: Interesting.

Garrett Gunderson: It’s now displayed, it’s now seen. It wasn’t sold, it didn’t get saturated, right? The museum’s like holding onto it.

Brad Johnson: Interesting. How did you become such a tax nerd? Where did this happen? And by the way, I say that with respect, by the way.

Garrett Gunderson: No, it was just, I didn’t want to pay the taxes I was paying early on. I was paying a lot of tax early on and I was like, what am I going to do? I got into a lot of real estate to avoid tax and I hated real estate. So, I’d rather pay tax than own real estate, personally. Someone just said, oh, if you’re wealthy, you got to own real estate. Guess what? My real estate owned me. I had over a hundred properties. It’s like I’m talking to bankers and attorneys and property managers and sometimes tenants, and no tenant ever gave me a card or a hug. They only call me when the maintenance people somehow didn’t do their job or something bad happened. So, yeah, because you have the 750-hour rule that if you do that, you become a real estate professional. You get bigger write-offs. And I did that and I was like, no, I better figure out other tax strategies because real estate’s not going to be in my wheelhouse moving forward. And so, I got rid of all my real estate between– like, I started to sell it in 2007, but I was a greedy bastard. So, I put it on the market for too much. I sold a little bit and then I ended up selling a lot of it for very little, but through 2008 through 2009. So, that was greed. Greed costs me. I put it up for sell at the right time. I put it for 10% above market. Some of it sold, and then all of a sudden, it started to slide, and then I held onto a lot of property.

Brad Johnson: Well, you’re not alone on that one in ‘08, 09, I can promise you that. Well, my man, I know it is Friday. This has been absolute rapid fire, which is always is when you and I hop on a Zoom or just in person in general. As we wrap here, is there anything? You’re talking to a lot of advisors out there that are either watching or listening to this on audio, any parting words of advice just to a financial advisor out there, where you’re like, hey, here’s, you grew up through kind of the school of hard knocks. You’ve obviously worked with a lot of advisors over the years, a lot of entrepreneurs. Any closing thoughts on that side?

Garrett Gunderson: Yeah. So, when I was young, I got a good head start by being collaborative. I didn’t know what I was doing when I was 19 years old, but I had people that were willing to sit down and meet with me. So, I brought in people that were really intelligent and I just got to watch them work while they got paid and I got paid. So, it was like having, I’d split the case and I’d watch how they would communicate. And so, I became friends with them. They were excited because I brought in things that I couldn’t handle on my own, and I was just willing to talk to people that I wasn’t ready to, like, so when I was 21 maybe, I gave my first speech to an agency. They basically had heard that I was doing really well. They’re like, oh, you should come speak to our group.

So, I’m still in college, a senior. I’m studying in a book to try to prepare for this speech. And I had read an article on charitable trust. So, I talked about charitable trust. Mind you, I’d read one article, I didn’t know sh*t. And this guy comes up, he is like, hey, my dad’s selling his business. Do you think we do a charitable trust? I’m like, sure. I should have said, I don’t know, I just read one article, right? He brings me to the attorney. The attorney tears me to shreds because I definitely don’t know what I’m talking about.

But I was resourceful. So, I called the guy that wrote the article, this guy Greg Barrick, I said, and his secretary’s like, this is pretty amazing, a 21-year-old kid’s calling here. He just got crushed by an attorney. Greg’s going to like it. Greg gets on the phone, he’s like, dude, I got you. We’ll help him. It’s amazing that you’re young and you’re making this call. And the guy ends up doing a charitable trust, saved some tax on the sale of his business. It works out really well because his son had already sold him a whole life policy 20 years before, so he had a death benefit. Didn’t disinherit his family. So, I just got resourceful.

So, I decided this was kind of fun. So, I started hosting a study group, and it was just four of us. And then people heard about it. Within nine months, we had 150 people in the study group. And my whole philosophy was I just share everything I learn. So, I didn’t hold anything back. I didn’t have any secret that I didn’t tell someone else. I was showing case studies. I was debating accountants. It was just like, I want to be a better speaker. And I remember this guy came up to me, he is like, “Dude, I don’t understand. Why are you doing this? Like, I wouldn’t share my best practices.” I’m like, “Well, how good are you doing right now?” He’s like, “Well, I could be doing better.” I’m like, “Yeah, because you won’t share your best.” I’m like, what I’m going to tell you is, because you asked me, Brad, how’d you learn so much about tax? When I put my best foot forward, everybody came up and said, do you know about this? Do you know about this? Do you know about this? I learned most of the tax strategies from that study group, because people would come up and say, hey, have you heard about this?

And so, I started letting advisors shadow me. They just watched me because I was in my mid-20s. They were like, how’s this kid doing so much business? And they could just pay to shadow me. By the way, clients did more business with me because they’re like, this 40-year-old dude’s paying this 25-year-old kid, like, he must be really good. So, like, I made an extra 2,500 bucks for the day for this advisor watching me. I had more people converting. So, I was just super collaborative. And I still am. That’s why I’m like, hey, man, if people want to license, what would the Rockefellers do? They get the entire turnkey system. They want to license all the tax strategies and tools that we put out with the tax navigator. Like, I’m just, hey, I’m not taking a percentage of their business, I’m just giving them the tools and they just pay me straight up, but it’s 20 years of work that they get condensed.

So, to me, you find those people that are abundant, that are collaborative. You help make them money. They’re going to help you make money. I mean, it’s the reason you’re following Brad is because he’s sharing what they do, how they do it. They help people market. They help people understand this financial world. And when you have a community like that. That’s what’s going to help you get further. And plus, you’re listening to stuff like this that who knows what the hell we’re talking about. Comedy one minute, taxes another minute.

Brad Johnson: Got to keep it fun, man.

Garrett Gunderson: Life-changing content. Yeah, I mean, it’s just disappointing that Brad lost his longer hair.

Brad Johnson: I know. Dude, we used to be twins there for a bit. I think mine was a little curlier.

Garrett Gunderson: I mean, you were Travolta from Pulp Fiction, bro. You were just 100% to me. To you, not think Travolta.

Brad Johnson: I don’t know if it’s me getting older or what, but I get Travolta a lot these days. Or maybe it was just growing the hair out, but I did dress up as him in Pulp Fiction and my team did a side by side. The scene where he’s got the coat, he’s picking up Uma Thurman. And he’s like, he is glancing around. Like, they did a side by side. It’s pretty wild how close it looks. So, maybe we’ll throw that picture in the show notes too, just for fun.

Garrett Gunderson: Nice.

Brad Johnson: But, well, hey dude, I always learn something every time we talk. I always have a good time, get some laughs in. And you didn’t disappoint today. My final question for you. This is kind of part 2 of my podcasting journey. You were fortunate enough. Like, I should say, I was fortunate enough to have you as a guest on my prior show, The Elite Advisor Blueprint. This one, I feel like it’s kind of the grownup version of that show, Do Business, Do Life. You’re a dad, I’m a dad, you’re a husband, I’m a husband. And as you said, like, it’s about more than just making a bunch of money. You got to have fun. You got to create those moments that matter. And one of the things we say around here a lot is build a business that blesses your life, that doesn’t become your life. And that’s really a lot of the mantra behind DBDL. And so, I’m just curious, I’d love to hear Garrett’s definition of what does do business, do life mean to you?

Garrett Gunderson: Build a life you don’t want to retire from, even though you can. It’s like, you just choose what you do every day. It’s a get to versus a have to that you live on purpose and that you build the retreat along the way so you don’t have to retreat one day because you’re exhausted. I just feel like taking time off and then coming back, even if it’s a week, two weeks, even if it’s a month, instead of being like, I’m just going to grind and then when I’m 65 and too old to really enjoy it, my kids are too busy, like, that’s crazy. Like, our boy, Derek Coburn wrote an amazing book, Let’s Retire Retirement. And he is just like, he’s making an argument of just more time along the way instead of like, because when your kids are at home, you get the most of the time that you’ll ever get with them, and if you train them, that all you do is work. When you have the money to take them to do stuff, they’re going to be trained to only work. They’re not going to be able to go do that stuff with you.

So, it’s like, create a great life, create the life you love. That’s the game. And it’s not always an easy game, but it is the game, like doing the things that you love does, like comedy, it’s a detour. It was fun. And it definitely has a ramification financially. But at the same time, like I said, we have the cabin we want, the house we want, the life that we want overall. What is an extra, I could have made millions more during that time, but I would’ve been millions more miserable just doing things that were mundane and boring to me. So, you got to fight for the life that you want. Don’t let it get swept up in bills and effort and grind because everybody on social media will tell you it’s about the grind, I’m like, no, sacrifice is a lie. Like, you either, you choose into the life that you dream of and then the work is worth it. Sacrifice is when you choose into a life that you don’t care about enough, that you give away what’s most important for something that temporarily makes you feel good.

Brad Johnson: Well, and to your point, you could have made millions more. And what are you going to do when you’re 65 and the kids are off doing their careers? You would pay millions to buy that time back now, you know.

Garrett Gunderson: Dude, I got to tell you, it was so special. Like, my wife was in the front row during the second show and when I told that Paris story, she was hysterically laughing. We have it on camera. My youngest opened it for me. He did five minutes of comedy at 13 and just absolutely crushed it. He watched me struggle to get there. My oldest would watch. Anytime I was in the editing room, anytime I was watching the special with someone, because I was excited to share, he would sit down and watch it and laugh. Like, they got to see what it looked like for me to pursue a dream that I didn’t have the capability from day one.

Like, when they came into watching me in finance, I’d already had a New York Times bestseller. When they were kids. I’m already their hero. But staying their hero, that’s a different game, as they age and everything and they see that like when my kids are young, they’re like, “Dad, you could beat up Mike Tyson.” I’m like, “No, I really couldn’t.” They’re like, “Yeah, you could.” And I’m like, “I appreciate you guys think that way, but you just don’t understand.” But being their hero later on, my son, I just turned 47 and his card said, hey, man, I work out because I watch you and I have a job and I put half my money in Bitcoin because of the conversations that we’ve had. And I was like, I love that, man. It’s like, that’s awesome.

And my son was just like my homie all through being young and then when he grew up, he just sat with his friends and I had to just be okay with that because he needs to create his own life. But I also, when he does want to spend a moment, I’m taking advantage of that. And we’re doing quarterly retreats as a family right now. We just booked one last night. We’re flying into Austin. We’re going to go see a game at Texas A&M because my son might go there and then, the next one’s going to be in Phoenix and then we’re going to do one in Jackson Hole. But we got these quarterly retreats just to get together as a family, hang out and talk, spend some good time together because I don’t know how much longer I’ll be able to get the kids to do that.

Brad Johnson: Yeah, I love that, man. When we first met, I mean, I had like a five, six, seven-year-old. Now, I’ve got a 15-year-old. And you’re right. Like, they really quickly go from your little homie to like, dad’s not the cool guy in the room anymore when you’re 14 or 15. The jokes don’t hit the same, which is sad. It’s kind of that dad sadness, but it’s a different season. You have to embrace it. And we all had that too. Like, I wasn’t hanging with my dad at 15, thinking he was the coolest guy in the room, and he’ll tell me that. So, we just– it’s these seasons of life and I love how intentional you’ve always been with those, man. So, we’re long overdue for a hangout in person, so…

Garrett Gunderson: That’d be great, man.

Brad Johnson: We need to make that happen. But always good to get to spend some time with you virtually. So, Garrett, thanks, man. As always, thanks for pouring in to the audience here, and until next time, my man.

Garrett Gunderson: Thanks, man.

Brad Johnson: All right, we’ll see you.