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Some people in the financial industry have the habit of taking everything as gospel. They consider anything they learn off of a book or from a mentor as 100% true. Garrett Gunderson found humor in all of this and talks about things that most people are too afraid to say, merging money with funny. Learn all about wealth with some jokes on the side with Patrick Donohoe and his guest, Garrett Gunderson. Garrett is the Founder of Wealth Factory and the author of Killing Sacred Cows. Learn how to give important information while still being funny, understand why wealth disappears when you’re no longer true to yourself, and so much more.

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Merging Funny With Money: Understanding Wealth And Humor With Garrett Gunderson

There is a saying that embodies the idea of absolute and unwavering commitment. That saying is, “Burn your boats,” which is to say when you make a decision or a commitment, there’s no plan B, no escape clause, and no way to back out of the commitment. My good friend Garrett Gunderson has made a pretty bold commitment. He’s made one of the riskiest moves that I’ve seen in a long time. He spent what most people would consider a fortune on training, coaching, Hollywood-level film producer and production crews, and other consultants to create this one-hour comedy special primarily focused on the topic of money and personal finance.

In June of 2021, I was fortunate to be invited to the live taping. It is seriously a level ten. It met all expectations and exceeded them. It’s honestly hilarious. Before this film is actually made available, Garrett is going to be doing a multi-city tour and it may be coming to a city near you. Why did he do it? Why comedy? Taboo topics of politics and religion have a stepchild, which is money and personal finance. The stack of cognitive biases that prevent the mind from rationally evaluating financial strategy is pretty thick. The exception is someone having an open mind. However, the rule is that what’s familiar or what’s status quo is to stay on that course.

Garrett hypothesizes that humor is a catalyst to breaking through these filters. He’s written three books, one of them is a New York Times bestseller. He’s been in the space for several years and despite what most would consider a success, his mission is to break through what keeps holding people back from living a life that they truly want. He’s spoken on videos and has a pretty broad social media audience. He’s taken his message as far as he can go. In this three-part series, you’re going to learn a few things about what he’s doing and why he’s doing it.

Number one is how powerful ideas have made their way into our belief systems with any vetting, scrutiny or evaluation, and how difficult it is to go back and objectively understand these beliefs without shortcuts such as humor. Number two, you’re going to learn a unique perspective on wealth and what people are really after with their goals like retirement or financial freedom. In the third episode, we’re going to talk about Garrett’s journey where he put his successful career and reputation at risk and why he’s done it, and everything that has led up to this point in time to this decision. You are going to love these episodes. I can’t wait for you to experience this new content from Garrett. To learn more about his tour and if it’s coming to a city near you, go head over to FreeFlow.group. Enjoy.

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What’s up Garrett?

I’m doing good. I got to spend a little time with you which was nice, doing some comedy for your financial guys.

You’ve come such a long way. I remember back in the early days, you always had humor but you brought it to a totally new level. I’m excited to talk about what you’re up to. I first want to set the stage because there are probably people that have not heard of you before. I was hoping you would walk through your journey in the financial advising and the personal finance space. You’ve written two bestselling books and one of them is a New York Times bestseller. You’ve experienced quite a bit. I’d love to hear about your journey because that’ll set the stage for what you’re doing right now.

I won $5,000 for being the Young Entrepreneur of the Year as a teenager. That seemed like a ton of money for me. I came from a coal-mining town.

That’s a huge amount of money.

I had this crazy thought when they handed me the check like, “Nobody else made that much money in that second.” That sounds ridiculous but that’s a teenager’s mind. I was just thinking, “This is amazing.” I want to invest it. Part of it is because I lived in this little town. I want to get to the big city which to me, Salt Lake City was big and intimidating even though it’s not, but coming from a town of 12,000, it seemed big.

I tried to invest the money but I was under eighteen and my mom wouldn’t sign off as a custodian because the Italian side of my family would put cash and coffee cans and put them in the cellar. Everything felt risky and looking back, it probably would have been because that was the ‘90s. I probably would have put everything in the stock market just because it was doing so well in the ‘90s. Not knowing why it would work or how it would work.

I remember when I was eighteen, this guy that worked for World Financial Group came and showed me this variable universal life policy and ran the illustration at 18%. At $70 a month, I was going to be a multi-millionaire 40 years down the road before I was 65. I’m like, “That’s illegal to show 18% first off. No investment in the history of the world has ever done 18% a year for that period of time,” but it was fascinating and I’m like, “This is compound interest and it’s not taxable.” That led me to ask a lot of questions and get an internship when I was nineteen years old for Guardian and Park Avenue Securities.

You know the way that really works. An internship was, “Bring your family and friends so we can sell them products.” The guy that ran that was very big on whole life. At the time, I didn’t think whole life was that sexy so I liked variable whole life because Guardian had this variable whole life product. You could put it in the market, which was again in the ‘90s, it was doing well. In the year 2000, two things happened. Number one was this dude from New York came up. He was bald but had a ponytail. He had a New York attitude, he was teaching, and he was slamming variable whole life. He’s like, “These are the ‘90s. This is the best you’ll ever do.” It was early 2000 and it started dipping for a couple of months. He’s like, “I’m going to compare with this couple of months of dip to a great decade to what whole life would do.” It was even.” He’s like, “This is even with no risk or minimal risk compared to high risk.” I remember getting a sinking feeling in my gut like, “Oh my god.”

Because you got people set up on.

The good news was Guardian would let you convert. They just let you convert the policy over to whole life. We went through and started converting policies. Also, at the time I went back to one of my professors from college, Steven Harris, who managed $5 billion of municipal bond funds for strong investments. They were the number two investment company in the world at the time. He was the number one investment money manager in the world for municipal bonds. He was always number one as the guy, and then he decided to become a professor. He walked away at 55 and said, “My next 25 years is going to be to pay it forward and be a professor.” We became friends and he helped me dissect what was going on in the market.

I didn’t know what I was doing and so between that guy from New York and him, I got all my clients but went out of the stock market. I started doing that in March of 2000. Everyone but one was out by May of 2000. For those that don’t remember, 2000, 2001 and 2002 were three double-digit negative years in a row. I saved hundreds of thousands, would have been millions. I didn’t have that much money under management because I was a kid, most of my clients were family and friends from small towns, but it helped me preserve some of those relationships. It was hard to tell people I didn’t know what I was doing but that began my journey.

Another mutual friend of ours, Mike Isom and I started flying together all over the country. It was 26 straight months. I flew somewhere to interview people. I went to symposiums or workshops because I wasn’t married yet. I had made some money in college and didn’t have a lot of expenses. I owned a property in Cedar City, Utah, where I went to school. My then-girlfriend, now wife, was living there while I was living in her parents’ basement because I was such a cheapskate back then, and just spending everything on learning this kind of stuff.

That’s when I started to focus on efficiency. I realized, “If you can save on tax, it was a pretty guaranteed rate of return. If you can save on interest, that’s a pretty guaranteed rate of return. If you can save on non-performing fees, hidden commissions or improper structure to investments, it was a guaranteed return. If there were duplicate coverages or improper structure with insurances.” These were all ways that you could put more money in your pocket without having to take more risks.

I teamed up with three other young guys that were always asking questions and always showing up to these kinds of things. We partnered with a firm called Ingenuity. We started this thing that was $20 a month because we realized, we can make people more money but they’re still the same person mentally. We would have people be like, “My friend did better in the stock market and I’m not in the stock market because you told me not to be in it.”

We figured we got to help people with their mindset. These producer perspectives, we email out to people five days a week. We had these producer forums once a month and we start to open up in different places and we bring speakers in. We have newsletters once a month and interviews once a month on CD that would acknowledge people. We started to focus on mindset while we were still helping people with their finances.

You get exposure to the mechanical, the more objective numbers side of things. You go and study. You timed it perfectly. Nobody knew that dot-com was coming or when it would hit. It was great timing, then you pivot and now you have a combination of the numbers side of things, making people more money but then mindsets. What led to the mindset? What led to that shift into the mindset as opposed to just continuing down the path of making people more money?

I had this partner, Les McGuire, who was very philosophical. We were in a program called Strategic Coach and every time we fly to Chicago to go to these sessions, we get these healthy debates and talking about things and dissecting everything. We would always talk about our clients and what was happening with them. I was talking about annual reviews every time in person. I was doing quarterly phone calls. I was really proactive with that. No matter what was going on in their finances, they still seem to have the same level of stress and the same issues.

Funny Money: There was no court jester of finance who’s out there poking fun at it. People can get easily offended by some jokes.

We were seeing they’re investing in our lives, going to things like Landmark Education and Strategic Coach. It turned me from being a total jerk to only a jerk. Eventually, I’ve evolved into a pretty decent person. Thank God for my wife, I did all this work because I look back to the kind of person I was. We recognize the impact it has on our lives. We had this philosophy that the best investment is yourself. Invest in yourself. You’re your greatest asset. It’s like, “What are we doing to help people with that? We’re just helping them with their assets, not with their mindset.”

That’s why we started that membership which was called The Producer Revolution. It was a pretty sizable movement. It created some fanatics and we had some philosophies that could have been developed a little bit more. The answer to every problem was, “Create more value. Don’t be a consumer.” There are almost some angst and judgment that came along with it. It’s kind of a visceral you get when you’re twenty years old and think you know everything. It was progress. It definitely wasn’t perfect, though.

That was back before we had to build our own platforms. There wasn’t WordPress, Kajabi, and all these plug-and-play things. We were hiring developers building it on C# platforms and spending hundreds of thousands of dollars, and then it becomes antiquated so quickly. It was a good step in the right direction. I remember in December of 2006, I was in Phoenix with one of my clients and he was good at mapping things out. We were writing this seven-stage process called the Freedom Fast Track, and the second stage are Sole Purpose Activator. It was a foreign weird thing to think about considering someone’s sole purpose, which is their values, their script route to operate combined with their abilities, and also what they’re passionate about in the highest context of how they live.

To put that in a financial program and then later I was like, “This is what makes personal finance, personal.” It seems common sense now but at the time, it seemed radical. It seemed out there. It seemed almost airy-fairy and I’m going to get attacked. I did a little bit but not too bad. I eventually wrote the book Killing Sacred Cows shortly after that. Now I’m in a whole other world of recognizing that there are just not as many people that want to be educated as that want to be entertained, and that finance is super intimidating for a lot of people.

What led to that understanding? Not to say that people have all stayed the same over the last couple of decades but now we have a different society. Social media took place in between the time you started and now. I would say, from a political standpoint, from a communication standpoint, even internationally, the world is now getting way more connected. What are some of the experiences that you’ve had that started to set your course a little bit different than you may have thought in the beginning?

I started speaking more heavily in 2005. We had some events before that but my other partners did some of the speaking, I was only doing it here and there. In 2005, I was speaking every month for our own things and flying to other places. When I was going to speak at other people’s events, sometimes I would be in a breakout session back in those days, but I was in a breakout session on finance. I might be going up against any other session. It was hard to get as many bodies in my session as everybody else’s session. I started hiring a lot of coaches like Roberto Monaco, Jonathan Sprinkles and Teresa Easler, everything around speaking. I can’t be a financial guy that people are intimidated by money and bored to listen to it.

I started doing that and I remember I went and spoke at this event in Vegas. It was all dentists. Every speaker had time on the main stage but for a very short period of time, it’s ten minutes. Sometimes at dental events, you get CE credits for going to courses. I’ve never got to offer CE credits so I’m now competing with people that are known in that industry and that might be icons, maybe they’re the best oral surgeon or whatever or they have CE credit and I’m a financial guy.

I remember I’ve been working for a while with these coaches and I got up and I get my ten-minute talk. I had the smallest room in actual physical size. I had only a small square to stand in because people are sitting on the floor. People were outside the door looking in because I’m joking around a little bit. I’m giving them a lot of information. My tonality is going up and down. I’m not monotone. I’m not wearing a tie. I started growing my hair right around that time and it was like this entirely foreign thing. That was the first taste I had of it. That was like, “There’s something different.”

A lot of times, at those events, you do short videos to say what’s the description of your thing was. I started learning marketing so I could write what it was and they could engage in different levels. I saw that entertainment at a pretty early time. There are a lot of times where I would show up at an event and one of my coaches Michael Port would say, “A surprise and delight speaker.” Nobody knew my name but I would be the number 1 or 2 rated speaker out of 15 to 20 speakers because I could bring that energy and entertainment.

I was in Italy for a summer with my wife taking all this time to relax. We had so many good nights where we’re all joking around and having fun. Because I had two months of time off, I was thinking and writing some jokes for fun. When we came back for my birthday, we went to an Atlanta Braves game and I’m telling her some jokes and she’s laughing. My wife is like, “Where are you getting these jokes?” I’m like, “From my own brain.”

I’m proud of myself here because to make her laugh, she’s not a fan. She’s not like, “Garrett’s a money guru.” No, she’s like, “Take out the garbage. I knew you from college.” I remember she comes to one of my events and there are more than 30 people at this event. I finish speaking and she goes to the bathroom and someone about them goes, “You’re Garrett’s wife? Congratulations.” She goes, “Congratulate him.” She’s not impressed but she’s laughing.

That was a Friday. That Sunday, I flew from Atlanta to Vegas and one of my friends at Keith Yackey’s event goes, “Our next speaker is hilarious. One of the funniest dudes you’re ever going to hear.” I’m like, “I got a fifteen-minute financial thought and he just said I was one of the funniest dudes. How do I do this?” I walked out on stage and I go, “Maybe the worst introduction I’ve ever had but I guess he didn’t mention I wrote a New York Times bestselling book called Killing Sacred Cows, which might sound amazing and flattering until the very first podcast I ever did and the guy called it, “Killing Scared Crows,” the entire one hour and a half.” At the end he says, “What should I invest in?” I go, “I’ve got a few suggestions. Bifocals, literacy or a new career.” The crowd’s laughing, I’m kind of teaching and I’m getting a setup.

I called my buddy who’s a comedian at the airport. I said, “Come to our office tomorrow. For two hours we wrote some jokes and I did an open mic. From August 2017, comedy became a hobby but during COVID, it became more of a complete pivot into a way to integrate my career. Because you were there, the night that I filmed my special called The American (D)ream, where I took this merge of money and funny and did an entire comedy special with some of the biggest names to ever produce comedy being involved.

My executive producer, Marty Palmer won an Emmy with Seinfeld. My editor, Michael Schultz won an Emmy with Chris Rock. My director has more comedy specials on Netflix than any other director and he was up for the Emmy for The Fresh Prince Reunion. They understood that there is no court jester of finance who’s out there poking fun at it. Back in the day, the court jester couldn’t make fun of things that were real that anyone else would get killed by the royalty. I can start poking fun at something so that we can start looking at it a different way. When I show up and talk negatively about a 401(k), it’s offensive to some people. It hurts them because they’ve worked so hard to put money into it. When I tell jokes about it, then they go, “That’s true.”

The magician or the funny archetype is a hard archetype to own. Naturally, that’s not your archetype but yet you discover this part of your personality that connects to people at a different level. In my experience in finance, you can easily toe the line of making people wrong and offending them. We’ve all done it and in the financial world, there are some very determined belief systems that are reinforced by books, personalities and media. If you think or believe something different, it doesn’t even matter the logic behind it. From an emotional level, people are like, “Don’t talk to me.”

That’s what is interesting about what I’ve learned from you because of this pivot that you’re making. When you have this humor, first off, tapping into that, you got to be vulnerable. I’m not sure if you can fake funny, maybe you can, I don’t know. To me, I feel that’s the genuine person when they’re funny. Number one, it brings down those barriers. Number two, just comedy in general, you’re able to talk about taboo or off-limits things.

The American (D)ream is the right title for that.

Even if you go to Chris Rock’s stand-up routines or Eddie Murphy’s stand-up routines, they talk about hardcore things that you don’t talk about at a dinner table or at a conference.

Without the comedy, it’s canceled. People are angry.

For sure, but when there’s a comedy, that’s an interesting dynamic where these experiences that you’ve had that taught you about personal finance, it’s a challenging industry. You’re always up against belief systems but then you figured out a way where you tapped into something genuine by yourself, where you’re able to connect with people at a different level where they’re now open to talking about what was off-limits before.

I wrote this poem and part of it says, “Comedy is the key when no other will do. Love is the answer but can’t always get through. Satire is pointing out what we hide, but everybody already knew.” That’s my summation of why comedy is so profound because they say that when you scare someone to death, they remember. I don’t want to do that to people. It’s almost as effective to make someone laugh.

I was talking to my sound engineer. We’re doing the final process of the special and he goes, “There are so many gut punches in this. I got to be candid with you. When they told me what you were doing, I thought, ‘How is that ever going to work?’” He goes, “It’s great.” It’s cool to win over some pretty intense critics in that world with a lot of stature and knowledge. Some of it is a joke that happened to come out that night that I was not expecting. I was saying, “This is too funny not to include,” but the theme is there. It’s going to help the masses face a topic that they’ve been afraid of.

Funny Money: There are some very determined belief systems that exist in the finance industry. If you think or believe something different, people will not talk to you.

I’d say that as you look at humor, you look at roasting or whatever comes to mind. When Demi Moore was roasting Bruce Willis, it was fascinating because those are things that without that platform, that conversation does not take place. It’s almost like society has gotten to this superficial level, which we’re all involved with, where it’s who you are, but then it’s who you are in public.

There’s a joke in my special that my manager is scared of. You heard the joke because you were there. I’m talking about how kids now don’t labor. They don’t need Labor Day off. Driving around with Uber isn’t labor or getting Jamba Juice or typing on a Zoom meeting isn’t labor. Having a baby is labor. That’s why they call it that, because it’s hard work that wrecks the woman’s body. Ladies, you deserve a few hours off afterward. He’s like, “You can’t say that joke.” I’m like, “It’s a joke because it’s stupid that guys would say something like that or feel that way. That’s what makes it funny.” It’s not like I’m saying it as a sexist. I’m saying it as the opposite like, “How stupid are we?” That’s why you get a laugh out of it but we’re a sensitive society.

The sensitivity is the conflict between who we are in public and who we are internally, and that gap continues to widen. These are thoughts that everybody has but nobody’s willing to express because it would violate some stigma associated with their public personality or public profile.

My sets are pretty clean because it’s not made funnier with vulgarity because I want to have a reach. In my everyday life, I swear a lot more than when I’m on camera. I’m also thinking about, “Does it add to it?” I remember, I posted one of my comedy sets and someone was like, “This was supposed to be clean. There are sexual innuendos in here. It’s so filthy.” I’m like, “I’m a filthy mind, what am I going to say?” I don’t want to mute myself. I want to be able to say things that other people can’t say and that’s what makes it funny.

I also want them to remember some things that helped them in life. The goal is, it has got to be funny first. It’s not just another lecture. I am truly declaring myself a comedian and based upon who’s involved with the project and where it’s going. I remember I did a practice run for a group of your advisors. You were laying on your side at one point laughing at my insurance jokes. I was like, “This is fun. This is good.” That’s good because I was doing a lot of Zoom at the time to prepare. Zoom is not as fun as people in the same room as you. You can only hear laughter one way a lot of times on Zoom. It’s been a challenge but a good one.

You said you want to get through to people to help them. When we first met, there was sincerity and genuineness about you where you wanted to make a difference. You talked about the things you thought were most important for other people to hear. Your journey led you to the point where even though you were saying the things that would help people, there was resistance on that initial layer that they were not able to get past, therefore, they weren’t helped. Maybe get into where you’ve come with your understanding of what wealth is and what people are pursuing. Unpack why aren’t people achieving the levels of life that they want especially in a society where all the information, all the books, everything is there to do it but yet people are still stuck, in a sense.

Wealth for me is knowing what your win is and living by your rules and your win, not everybody else’s. We lose wealth when we try to conform to society. When we try to please others at our own expense. When we buy into this notion that this is going to be a temporary thing. That we’re going to give up so much of what we enjoy so that one day we can finally live a life that we can love. The problem is those habits become who we are.

I had this conversation with someone and I said, “I’m leaving social media.” He’s like, “How are you going to do business?” I’m like, “There was business before social media, there will be business after. Social media is not part of my win, it’s not part of my wealth.” I don’t want to have digital assets where how I’m viewed is based upon the number of subscribers, likes or comments because then I’d start thinking superficially about what would be viral or controversial versus being who I am. This is a weird notion but I’ve had a renaissance in my life where I decided hobbies were going to be as valuable to my wealth as my business activities. They would be on par. They wouldn’t be beneath that.

I started taking courses on being a barista. My friend, my client and I built this thing called The Roast, which got a big bougie seat and I could pull it behind my eBike. It’s got a chalkboard that you open up and it’s got an espresso machine you could put up there. It’s got a generator on it and it’s got a sound system so I could roast coffee while I roast bad financial ideas, almost like jaywalking would be on the street. I’m like, “That’s fun.” I became a whiskey sommelier and then I started learning how to fish. I started taking classes at Trager and I went and shot an elk with a bow. I started doing these things that weren’t anything to do with money. They were just about my own enjoyment.

I start thinking about, “What art do I enjoy in life? What are the art forms that I would do for myself?” I write some poetry sometimes. Comedy was part of that. Some of that crossover into a business world or a financial aspect. The start was considering my life and myself valued a lot to take time for myself for no other reason and that I would enjoy those moments, not because of validation by the external world. By doing that, I feel like I can be more connected to the world versus having the world tell me what wealth is or what my win is. That has been this revitalization of my life. I feel more inspired. I have more ability to connect with people.

A lot of my hobbies have to do with satiating experiences, either meditative experiences or satiating. Satiating experiences are how can I create conversations that lead to connection? When I’m making a latte, I’m listening to someone. We sit down and we have that latte and we have a conversation while we sip on that latte, which prolongs that conversation. I started smoking a tobacco pipe every now and again, maybe once a week or so. I’m doing that with my dad who grew up Mormon so that was a surprise that he enjoys it. He texted me talking about having some tobacco and pontificating something about life. My mom’s like, “That reminds me of my dad. He used to smoke every Sunday.” I was like, “That’s a 30-minute smoke.” It’s a beautiful artifact.

I started to invest in hobbies and I have this philosophy in life that I win when I play. I play doing comedy. I play while writing. Even my new website, I’m writing. I’m writing things that are funny and enjoyable that are part of that process. I created life on my rules and on what my win is. I’m not trying to retire from anything. I’m not trying to run from anything. I’m not trying to hide from anything. That can be difficult at times but it’s rich and rewarding. That’s wealth. When you know your win and you’re living your life based upon winning all the way along and not about arriving somewhere.

That was the point I was going to make a follow-up question to because this is something that most people would resonate with, “That would be nice.” They look at you and others who fit that persona and they say to themselves, “I have to do this first to do that.”

That’s sacrifice. Unfortunately, we learn that through conversations and culture. Did you ever play The Game of Life, the board game? The only way you win is by getting your college degree. That creates a subtle belief about why we have to go to college. You played Monopoly. How do you win a monopoly? Get as many things as possible. It’s a zero-sum, winner-takes-all game. We start buying in that belief with capitalism. That isn’t what true capitalism or free market would be. It’s what cronyism becomes. It’s survival of the fittest versus collaboration.

I’m like, “I’m playing games that everybody else told me to play, go to college, get a degree, have a big business and grow that business.” It was always about, “I’ll take care of my health later. I’ll have time for my family later.” Those were always in the background and then the great lie that all business owners ever tell their spouse, “I’m doing this for you,” but it’s not. It’s for the fulfillment of our narcissistic ego and this unfillable void of more is better, and all those notions that we learn in society, especially here in America. There is merit to some of that but there’s a lot of false reward to a lot of that, especially when we’re trying to prove something to other people.

I was practicing my comedy set. I had a terrible night. It was on Zoom and some people on including some who used to coach me in speaking and I had some friends in a dining room and there’s a chef in the kitchen. It was at my friend’s house. My wife’s in there doing her culinary homework in the kitchen. It’s noisy and they’re like, “Can you be done in an hour?” My set is an hour and a half. The worst thing you can do is take an hour and a half in comedy and make it an hour. The best thing you can do is to go, “I won’t show 1/3 of my set.” I condensed it and the guy said, “You sucked.” I did. That’s the truth. It wasn’t good. What was hard is not to have that be a chip on my shoulder be like, “Wait until I do this on the next show.”

What I did was I waited. A month later, I finally shared it and he goes, “I can’t believe that’s the same thing.” I’m like, “I had an off night.” I learned a big lesson from that. A big part of the lesson was along the way enjoying it. Not waiting for April 15th but being like, “I had this set in March in Ogden at the Wiseguys Theater.” It was an amazing set and it was one of the best nights. It wasn’t that the night was only good. As a standalone, that was a win. That was an enjoyment. Enjoy that moment. Extract that moment. Even leading up to that night, my last line, I felt was awesome. I couldn’t wait to sit but I was like, “I want to enjoy every moment on that stage.”

Often, in life, we’re trying to get to the next moment. It’s a silly movie but a movie that impacted me was Click with Adam Sandler and Kate Beckinsale. He could fast forward through anything. He missed everything. Most people would do that without proper perspective. We’ve learned that pain is something to avoid. What I’ve learned is pain is part of the process and it’s a gift even if we don’t like the wrapping. It’s a tap on the shoulder. If we’re willing to go through it with love and compassion, on the other side of that pain is always connection and lesson.

My wife woke up early one morning and I’m like, “What’s up?” She’s like, “I’m sad because I’m trying to get our son in this camp. He’s got to have certain vaccinations.” My son had an adverse reaction to a vaccination back in the day so he’s not up to speed on certain tetanus and polio, which I don’t even understand why you would have to have that. She’s like, “I don’t think they’re going to let him in camp. He’s struggling with friends.” I was like, “If you need to call the camp and have me on the call, I’ll be on the call.” Otherwise, I was doing my best not to get sucked into thinking that I have to make her happy, that that’s my responsibility or that there’s something wrong with her being sad.

She was able to get a hold of the camp and they’re going to let him in. Even what she did, I do a lot of times, which is we suffer in the future. We start thinking about what’s coming up and we start thinking, “What can go wrong with that?” We start suffering for something that hasn’t even happened, and 99% of what we worry about is never a reality. The stuff that has the biggest problems are things we could have never predicted. I feel like we’re going to have the tools and we’re going to have the lessons through those even if it is painful. The people that struggle the most are the ones that try to avoid the pain, hide from the pain, run from the pain, and go around the pain when going through it is the only way.

I was reading Meditations by Marcus Aurelius and the definition of a meaningful life hasn’t changed at all since then but yet the world has become more complex. It’s been more difficult for people to have those moments of meaning.

We’re better at faking things now. We have tools to make things look and feel real.

Funny Money: Don’t mute yourself. You want to be able to say things that other people can’t say.

It makes it even more difficult.

Filters, social media and editing. I don’t know how to describe it without sounding too crazy but I’ll say it. I’m in acupuncture and relaxing. I have this moment of clarity. I felt like it was God saying, “There’s nothing to worry about. I’ve got you. You’ve got this. When you make mistakes tonight, it’s part of the process. Make them. It’ll be okay.” You’re in Show 2. I didn’t make as many mistakes in Show 2 as I did in Show 1. In Show 1, I forgot where I was at one point. This girl was laughing so hard that I got distracted because she thought the word cavemen was funny. I kept saying cavemen but at the end, I go, “Does anyone know where I’m at?” Everyone started laughing because I’m making a mistake. My manager yells and so I picked it back up.

In the second show, do you remember the tooth bunny bit? I was meant to say the Easter Bunny and I said the tooth bunny. That stayed in the special. It was a mistake but it was funnier. I talked about the Easter Bunny. No wonder we have a problem with pedophilia. We have a stranger in a costume here and kids go to him and he’ll give you things for free. I go, “That reminds me of a story with my wife.” Everybody started hysterically laughing because the last word was pedophile. What I was supposed to be referencing was free because she went to spring break when we’re dating and said, “I don’t need any money because the guys are super nice. They’ll give you drinks for free.” Those were accidents. Those were mistakes that made it funnier.

The fact that I went in without knowing, I was able to be in that moment without fear. I didn’t tense up. I laughed with you guys. I rolled with the punch. In life, we try to control the uncontrollable and that creates unnecessary stress and worry. That worry starts to become who we are instead of who we are. Everybody gets a dumbed-down, lesser version that’s not present because of how we handle things, because of what we think is right and wrong, because of how we don’t want to be judged. Ultimately, we don’t show who we are because we think that if we’re someone else, people will like us more. That’s my estimation.

I’ve done a lot in my life too. I don’t think you can completely avoid that. It’s part of our makeup. It’s part of our DNA. We’re more aware of it.

I have too many windows open that are running in the background and slowing the software down. I’m like, “Why am I worried about that? Let’s have a conversation. I’m going to call that person. This person didn’t text me back. Do they not like me? I’ll call them instead of sitting there and worry about it.” I always think, “Maybe they have other things going on. Maybe a lot is happening in their life. If they don’t like me, that’s up to them.”

You’re walking on the side of the road with a stranger and you have ten minutes to talk to him. What do you tell him? We’re all human beings. We all essentially suffer from the same programming in a sense. We’re all part of the experience where stuff happens and we respond to it in similar ways. It’s this never-ending pattern that we get stuck in. You’re talking to someone for a brief period of time, what do you say?

What would life be like if we trusted ourselves more? What would life be like if we listen to our intuition? Intuition is such a gentle nudge. It’s an inner knowing. It’s a gut feeling or a light feather to the face. It’s super easy to ignore but the more we ignore it, the more we have unrest, depression and we succumb to scarcity. Intuition doesn’t always lead us towards the easy path. That’s the thing. That’s why we like to ignore it sometimes. Sometimes it leads us down to a challenging yet rewarding path. Sometimes it’s because we think that we’re too alone, we think that we’re not capable or it hasn’t been done before. When I say we, I can be good at talking myself out of it.

I had surgery on November 3rd, 2020. I was in my bed for several days. I was eating gummies for pain management to go to sleep. I didn’t want to take any opioids. I don’t do good with weed at all. It makes me disconnected and I can’t even formulate good sentences. I found myself being like, “Why do I think I could be a comedian? This is stupid. This is dumb.” At that time, I was like, “I’m going to do a special.” I had written an outline.

This is was early 2020?

Yes. November 3rd was the surgery date. I turned on The Zen Diaries of Garry Shandling that was done by Judd Apatow. It was him talking about his doubts of ever been good enough to be a comedian and all this kind of stuff. He has some cool things he wrote in his journal, which reminded me of things I’ve written in my journal. I was like, “I’m going to do this.” I can’t even walk down the stairs because of the surgery and all this stuff.

November 15th was when I called comedian Marcus and said, “I want to write this. Do you want to help me?” He said, “Sure. We could write a special by January.” Barry Katz, my manager in the Industry Standard podcast, announced that I’m going to do it on April 15th because I said I was considering it. All of a sudden, a brand new comedian is going to film an hour special that I started writing on November 15th and I’m going to perform on April 15th, where most professionals are going to take a year to do this.

I’m on Zoom five days a week testing this out. You were there for one of them. I’m walking, reciting, rowing, rewriting and it worked out great but it was uncomfortable. I had to face many demons of insecurity like how to be direct with people, how to ask for what I want, how to allow a vision to expand beyond my comfort zone and make changes, how to say no to things so I could truly focus on this, and how to allow other people to support me. There were many things that had to go on for that to occur and that was the most growth.

Who I am from January 2020 to who I am now, I have to reintroduce myself to the world from who they knew in the past. I’m willing to listen to intuition. I’m willing to do the harder things and process through pain. I’m convinced that on the other side is love and connection. I feel worthy of love. I feel that I still have insecurities but I still love myself even if I’m imperfect. I’ve adopted the statement, “Perfectly imperfect,” as part of my life. I don’t have the answer but I do have the question. My question at all times whether it’s convenient or inconvenient is what would love choose? What would love do? How would love show up?

I used to think that what was most unique about us was our abilities because that’s maybe a Strategic Coach concept but what makes us most unique is how we show love, express love and receive love. I’m like, “What if I mastered that? What if I invested in that and not in all the other stuff about more, but how to show up as love? How to choose love when it’s difficult? How to choose love when I want to pout and be a victim? How to choose love when someone I feel has wronged me or said something negative about me?”

When I said to someone I looked up to, “I don’t want to be part of this anymore,” something that was on the board, he was like, “That’s going to impact us.” I’m like, “I know but you’ll figure it out.” “What am I going to do?” “You’ve always found a way.” In the past, I would have been like, “You’re right. Let me do it,” even though I don’t feel like I have the time or capacity or I don’t feel like this is my calling because I want to appease you. I was like, “You can even go and tell people that I’m an ass and I’ll be okay.” I’ll keep showing up as love. Part of the time, that is having clear boundaries.

What I took from that is the question you ask yourself, especially when you’re experiencing fear, anxiety or stress.

It’s easy when times are good.

The primal part of us shows up when things are not how we expected. Number one, it’s the awareness of it. Number two, it’s not relying on those carnal instincts. It’s strategically designing a way in which you can ask yourself different questions and catch yourself and then be more present and enjoy that moment.

I don’t know how you feel about this but the way I feel about this is I have the ultimate testing ground, having a wife and having kids. I can be neutral about things in business and not take much offense to it or not have to drag me into drama or a lot of emotion. If I don’t get my way with my wife, I can find myself on the couch. I find it harder to ask for forgiveness immediately or to not be right at the moment and listen. That is the ultimate place because I’ve shown her more of who I am than I’ve shown anyone else in the world.

Funny Money: You lose wealth when you try to conform to society or please others at your own expense. When you buy into this notion, you’re going to give up so much of what you enjoy.

There was a time where I believed that she didn’t love me and I wasn’t lovable because I’ve shown her so much. When I recognize that was a limiting belief, I’m able to even give her more love without the fear of not being reciprocated, “What if she doesn’t like this about me?” I joke that this is the 26th version of who she’s been married to. I’m like, “The only woman that’s been married to more men with one marriage is Danielle, Garrett White’s wife.” He’s on version 35. He’s even faster. He goes full steam ahead on any good idea and maybe he’s not like that now.

It’s one of those things where I hope that that’s what we all pursue. I don’t think there’s this end to our becoming. You have so much brilliance and meaning when you’re living in present moments because that’s where it all exists, but it’s this constant awareness that you can continue to iterate, improve and be better. It’s not to take away from how you are right now but be even better and continue to improve on the experience. I don’t know if we’re designed to sit still. He’s certainly not designed to sit still.

I was a miser when I was first married. I was all about the game of preservation, cutting and budgeting. My kids are fascinated when they hear these stories because they don’t know that version. I remember my youngest ask my wife, “Why is dad like that?” She goes, “He thought it would be the best thing for our family at the time.” In our first year of marriage, I felt like my wife was going, “What the hell did I get into?” I’m like, “We need to balance this checkbook. Why did you spend so much on your classroom? You’re supposed to get paid as a teacher and not be paying out. Why is this electrical bill so high?” I’m ridiculous and she was patient. She keeps holding a mirror up and saying, “Is this what you want? Is this who you want to be?” She creates that powerful listening for me that I could be like, “I could probably do better.” For her to still love that version but I appreciate this version even more. This is probably good that we’re not talking finance because people can learn finance from your book or my book and all this stuff. This is the stuff that is underneath it that captures wealth.

That’s where I wanted to go. Maybe it’s not direct but there is a total correlation between your enjoyment of life, who you are, and your understanding and your experience of wealth. We all live in a society that we should be in amazement 24/7 because of how we get to live compared to the past. Yet, there are still absolutely miserable people. You have people with lots of money. It’s this insatiable thing where they think that physical things are going to quench that thirst. At least my experience with things, I would love to get your thoughts. Your levels of impact have improved. By impact, I mean ways in which you create wealth. It’s improved because of your internal improvement. I’m not sure if there’s a direct correlation but I know that there is a tie. At least that’s my experience.

We’re in a consumeristic society where the eternal quest is for more.

The limbic part of our brain or that monkey brain, all it knows is to consume as much as possible.

Redefining the game changed everything for me. What if more meant more peace and less worry? What if more meant more leisure and less sacrifice? What if more meant more meditation, more recreation and less frustration? In my twenties, I had so much ambition that more meant more revenue, even more employees so I can tell people how many employees I had. Do you remember my office back then? It was way extravagant for where I was at that point in my career. It was more about more shows and less personal growth because I didn’t have time for it. The work was being at work versus working on myself.

I had enough of it because I was like, “If I do this work.” I remember one of our mutual friends, Vince, was like, “Go to Landmark.” I thought it was going to make me a better financial advisor and it did, but not for the reason I thought it would. In my twenties, I did a lot of talking on this podcast. I do a lot of talking but now I’m focusing on listening more. Not just listening to people but listening to intuition because I feel like intuition is the source. It is the knowing, the divine path or the divine will. I can have free will but that can be a lot like a detour a lot of times than listening to that intuition. My self-choice would be to pay attention to it or not. I might be a little bit deeper on the philosophical level but I found that to be true.

I don’t always listen to my intuition. I was in LA walking and I saw this kid that looked like he was in mental pain and angst. He didn’t look like he’d been homeless or if he had been homeless. My intuition was like, “Go talk to him. Walk by.” It was inconvenient because there were other people. I’m walking in the airport and I see this girl. She’s a little bit heavier but she was beautiful. I’m like, “Go tell her she’s beautiful.” I was like, “I’m married. That might be weird.” My intuition is like, “Maybe she does need to hear that at that moment.” I start rationalizing and justifying out of safety, protection, convenience, inconvenience or hustle. I’m listening to my intuition because I had a dream to write a one-man show. It was a dream. I woke up and I’m like, “I’m doing it.” You’ve seen it. You’ve seen the impact it has. It’s not even officially out yet but that’s intuition.

Important Links:

• Garrett Gunderson
• FreeFlow.group
• Strategic Coach
• Killing Sacred Cows
• Meditations
• Industry Standard

About Garrett Gunderson

I am the author of the New York Times and Wall Street Journal bestselling personal finance book Killing Sacred Cows: Overcoming the Financial Myths That Are Destroying Your Prosperity.

Founder and Chief Wealth Architect of the Inc. 500 firm, Wealth Factory. A regular on ABC’s Good Money, he has been on Fox, CNBC, as well as hundreds of radio interviews, and I contributor for Forbes. I also am a frequent speaker at workshops and conferences and live in Salt Lake City.

I have also been interviewed by some of the greats in the personal development space like Hal Elrod, Robert Kiyosaki, Ryan Moran at the Capitalism Conference, Dan Sullivan from Strategic Coach, the Mindvalley Podcast, Project Life Mastery with Stefan James, Joe Polish of Genius Network, Entrepreneur on Fire with John Lee Dumas, The Science of Flipping with Justin Colby, The How of Business, and many more!

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