Redefining Your Path To Success With Garrett Gunderson

The path to success is different for all of the most successful people in the world, depending on their backgrounds and their industries. But their stories have a lot more in common than you might think. Together with Dr. Diane Hamilton, acclaimed “financial genius” and author, Garrett Gunderson, gets into the commonalities that run through the stories of the world’s most successful. The paths forged by the people that have come before might just be the blueprint to your success – or at least the inspiration. Make sure to give yourself this chance to come into success!

TTL 664 | Path To Success


I’m glad you joined us because we have Garrett Gunderson. You’ve probably read his books. He’s a New York Times bestselling author. He’s also a financial genius and he does so much from stand-up comedy. It’s amazing the variety of things he does, but he’s the guy that tells you how to get wealthy and stay that way.

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Redefining Your Path To Success With Garrett Gunderson

I am here with Garrett Gunderson, who is called a financial genius in entrepreneurial circles, but he says he wasn’t born with a silver spoon. He has blue-collar roots, which make him passionate about helping others build economic independence. You’ve seen his New York Times bestselling books. He’s everywhere. I don’t know if you’re familiar with all of them, but Killing Sacred Cows is a huge one. He’s got 5 Day Weekend and What Would the Rockefellers Do?: How the Wealthy Get and Stay That Way, and How You Can Too, which I’m interested in. I was watching one of your videos, Garrett, on the Seven Foundations of Wealth. I want to get into that, but it’s nice to have you here.

Thanks for having me. I look forward to this conversation.

I was looking forward to it too. I’m a bit of a Quicken junkie. I’ve always been interested in finance. How did you get into the business?

I had a business when I was fifteen years old, detailing and washing cars, nothing too fancy. When I had a $600 income, I won a competition, Young Entrepreneur of the Year, Rural Entrepreneurship which came with $500. I was like, “That’s awesome.” The next year, I won $1,000 in the competition, then I won $5,000 for being the Entrepreneur for the State. I wanted to invest that money. The reason I want to invest wasn’t any big idea. I want to get out of a small town and I was excited to get to a big city. I thought Salt Lake City, where I live, was big, which is funny to think that I’m here. I was curious about how do you invest and where should you invest?

I interviewed a lot of people. I cleaned cars for the credit union. I talked to the president there. I talked to my uncle, who had a bunch of money. I would meet with people that were in the fraternity, but much older than me and graduated in the financial space. When I was nineteen, I got an internship which is basically a glorified way of saying, “Peddle mutual funds and life insurance to your family and friends.” I did that and it was okay. For the first couple of years, it was fine because I was making everybody money, not because of what I knew, but because the market was growing. In the year 2000, the market started to decline and that’s when my real journey began. I decided after telling people I didn’t know what I was doing, which was hard to do because I was slightly an arrogant kid at the time, but it saved them from having a lot of losses in the market, I said, “I’m going to figure out how this works.”

I started flying somewhere every month for 26 straight months while I was still in college. I was interviewing people and going to things. You can leverage your age when you’re young. People will meet with you but probably would never give you the time of day. If they want you, you become friends with their secretary and then they will anyway. That’s what happened. I started to demystify something that was complex for a lot of people. I started to dissect what was going on and questioned everything. That was the beginning. I’ve been fascinated with money because it doesn’t come with a good rule book, yet we all deal with it. It’s one of the biggest reasons that people are in pain and confused and not able to give their gifts to the world. People listed as a reason for divorce, but the reality is when we don’t understand money, a lot of times, we don’t get excited about the future because it feels scary. I feel like I have a deep amount of compassion, love and empathy for a topic that a lot of people are transactional about.

You touched a lot of curiosity in everything you’ve said, which is the topic that I talk about. I love how curious you were. Why do you think you were when other people aren’t? It is such an interesting topic to me.

One is coming from a small town and not being around people that were financially savvy. Curiosity was the only way. It wasn’t like I was taught something and I knew it definitively or I was around people that talked about it all the time, but I knew that it existed. You could see it on television or read about it. I was subscribing to the Wall Street Journal when I was eighteen years old. I don’t anymore because I don’t need it. I’ve left that world and that thinking process. I was curious because I want to be successful. When I was five years old, I had a teacher throw something away because I didn’t do what I was supposed to and figured I was stupid. It was me trying to prove to people that I am smart and because nobody knew about it, I could figure it out, I thought it would make people love me more, to be honest. At least it got me started. That’s a limited game, but at least it got me in the right direction.

You mentioned not taking the Wall Street Journal. What don’t you find helpful about that?

I’m not in the world of stocks. The world of stocks is about big corporations that I don’t necessarily agree with how they do business and how they operate. They raise their stock prices on the back of employees and sometimes by cutting corners with customers and the pressure is on the leverage of the shareholder because there’s a shareholder fiduciary responsibility for a CEO. That fiduciary responsibility doesn’t exist for employees. I feel like the people that are making things amazing are small business owners. The people that become something because it’s something that they care about and they’re connected to. They’re not trying to sell out and be corporate and exit so they can have a huge windfall of money that they could buy a bunch of stuff that isn’t going to give them a fulfillment that they think that they want.

I’m not passionate about these companies, about stocks, and about reading earnings reports or why this company is going to be great. There’s a lot of misinformation because of strong bias. If a company is going to have an IPO, the majority of the major institutions are going to say, “Why should you buy that?” There are not many people saying, “Why you shouldn’t? Why it’s not a good idea?” It’s against the good old boy network and the code, the way that it works in how you do things. You might have some people that say something negative about a company here or there, but we could see people like Jim Cramer that said, “Bear Stearns was a steal.”

He went down again and said, “I can’t believe everyone isn’t buying,” then he went out of business and talked about the next thing. We’ve got this notion that investing is synonymous with stocks. Investing is synonymous with skill-building. Investing is synonymous with figuring out who we are, how we can contribute, and that you are your greatest asset, not some stock-bond or piece of real estate. We need to get clear about what we’re here for, what we can do best and find something that’s fulfilling enough that we don’t want to retire from it. Putting money in these other things is a mere distraction more than it is what people want.

[bctt tweet=”Any business that’s going public is not a small business anymore. ” username=””]

You were talking about small business. What do you consider small? How big is too big to be considered small to you?

Any business that’s trying to go public. If it’s going to go public, then that’s not a small business anymore. Any company that’s remains private, there might be different variations of that. A lot of times, the original reason that the stock market existed was quite amazing and beautiful in a lot of ways because it was a way for companies to raise capital. Back in those days, we didn’t have the ease of transaction. We didn’t have the internet to be able to have a market where a company would require capital to build something, that would take some time to come to fruition, or take bandwidth and be able to hire people. That’s an awesome thing that they could go public and raise that capital.

It’s shifted in nowadays world. Going public means exiting, getting the BYOD, getting the payoff, and it’s the end of the road to a large degree and you’re already wealthy. It’s not about raising capital anymore, at least for the majority of it. It’s lost its purpose. Unfortunately, a lot of people blindly hand their money over to it, not knowing if the companies are going to be successful or not. How it works, who’s involved, how they’re going to benefit, what the fees are, and what the volatility impact is going to be on them. We see a 95% failure rate when people turn age 65.

90% of Americans are not economically independent and that’s the US Department of Labor statistics. People are funding retirement accounts and it gets them a false sense of security that they’re going to be okay in the future and be able to spend this money. The reality is it’s not what it’s cracked up to be. I want to make sure that people learn how they can get immediate cashflow, how they can improve their finances through organization and simplicity, where they can find guaranteed returns. The only way I know to get guaranteed returns is to save on tax, save on interest, save on non-performing fees, and save on dues and fees of coverages or costs with insurances.

When we start getting into speculation, then we play the game of volatility and risk. That volatility and risk might take our eye off the ball of enjoyment of life. It might take our eye off the ball of investing in ourselves. It might have us get false hope that it’s going to be better in the future. We turned out, we get there and we find out its not 95% of the time. We’re in a broken system because of a lack of responsibility because it’s hard to have the courage and face our finances. There’s a myriad of marketing and misinformation. This is misleading. I’m packing a lot in these statements here, but find to unpack them.

I had interviewed Kenneth Fisher about the stock market. In his book, he talked about once you read about something that’s happening, it’s already too late. It’s already built into the stock and people who are trying to time these things can’t do it. Do you agree with that?

Totally, the market reacts to that information. It’s moving quickly and we have supercomputers that are part of the trading process. Even if you’re buying a stock, someone could buy that out from under you, raise the price a little bit, and sell it to you and skim the difference. There’s a book that I read on that and it is phenomenal.

In real-time, everything is a game. If you could figure out how to play it is the question.

If you want to play it, that’s the second question, like, “I’m in the game. I’m in this world for value creation.” For me, the world has bought into this bold statement, but I feel it at a deep level. We bought into this notion that it’s a competition. Everything’s a competition, like sports. We believe that money is like sports. We believe that business is like sports that one takes the other losses. There is a winner and a loser that pits us against each other. The reality is that it creates a selfish notion. That selfish notion justifies false reporting. It justifies doing something and saying, “Even though that might not have been the best thing to do, it’s what you’ve got to do. It’s business.”

We get this notion that stifles creativity and value creation. When we play in the world of value creation, it’s born of collaboration instead of competition. It’s born of delegation instead of hoarding and doing everything on your own. It’s born with creativity and sharing that to uplift an industry, rather than be the best in the industry and keep everybody else in the dark. It’s even a game of elimination, not doing what no longer needs to be done because it’s not who you are. There are things that we can all make money with. The question is, should we make money with it? It might be a distraction. Disguise is an opportunity. It might drain our energy and we could’ve done something more useful with our time. We may neglect our health in the name of, “One day, someday it will be better. I have to hustle.” I can go through these myths that have permeated people’s minds based upon the faulty, selfish notion of competition.

I came from a family that everything was a competition. I can relate in terms of what we’re taught. I’ve often made the comment that my dad would want you to trip the guy next to you if you were running against him to win. That’s a bad thing in my mind. It taught me, which is interesting because later, I ended up teaching ethics. I use examples of my childhood and how not to do certain things. Are there companies you won’t buy from because of what they do ethically?

I’m not the moral authority on this and I’m not enlightened enough to make all those choices well. I do everything I can not to buy from Monsanto, but who knows everywhere where their tentacles are? I feel like we bought with our dollar. I’d prefer not to buy on Amazon a lot of times, but candidly, they’ve made it convenient because they are the epitome of competition. What they’ve done to a lot of my clients that are Amazon sellers, changing algorithms on them, creating an Amazon choice after that person did all the research, taking away all their reviews so that Amazon populates higher. There are some vicious things that happened there, but at the same time, I don’t invest in those companies. I do my best not to spend dollars on those companies, but I am human and I am flawed.

TTL 664 | Path To Success
Path To Success: How do you invest, and where should you invest?


They are convenient. I heard you.

Some people probably think I’m like, “They’re putting me in a political camp.” I don’t have a political affiliation because I can see clearly communism is this great lie, that if you forfeit something, they’ll take care of you. Because we worry about our family, we worry about others, it’s easy for people to buy in that line. You find out that there was a tyrant that was basically lying to people and you don’t end up with a better life. Socialism, I see why people start gravitating towards it because we want people taking care of it. It’s unfair that only a few people have so much wealth and there are people that are starving. We see this problem in the world and we think an ism is going to solve it. A lot of times, that’s a big heart, small brain, then capitalism has this massive lie, which is, “This is a free market. No, this is the takers market. This is a competitive market.” Its none of those are the answer. When you put an ism behind it, what it blocks is humanity, connection, love, and value creation. All we’ve got to look at is the free market. It is giving people a willing choice to make decisions. Yes, they’ll be taken advantage of at times and they’ll learn lessons. No one can govern it all.

I never want my wife to be hurt. I never want to see my kids in pain, but the bottom line is if I hover over them, I’ve taken away all their freedoms. I can’t control all the variables and as soon as we expect someone to do that for us, we’ve lost the game. Part of the game includes pain bottling and the other side of it is love and connection. Part of the game includes lessons along the way, mistakes and harm. We were going to have these experiences. Mistakes are part of the process. It’s what it means to be human. When we try to forfeit our responsibilities and our freedom because we think someone else cares more about our money than us, we’ve already lost. A lot of people have got to that point where they’ve already lost the game. They don’t know it yet.

You’re talking to many different generations who have a different perspective. Boomers are trying to retire, maybe they want to, and they’re behind where they think they should be. Millennials are maybe late to entering the workforce because of other reasons that they don’t see the need to hurry up.

They saw too many people work their life away.

Gen X, the Sandwich Generation is taking care of everybody on both sides, their kids, and their parents. You’ve got a lot of different types of issues that you’re talking to many different people. I watched a part of your video. I didn’t get through the whole thing, but I loved it. That part I did see of Seven Foundations of Wealth and you’re talking to many people here. Let’s look at those Seven Foundations from Gen X from an older perspective. How would it relate to them? Can we go through some of those Seven Foundations? I think they’re important.

The notion of retirement is part of the problem. We were sold a bill of goods that the younger generations are not buying. That bill of goods is going to school, get good grades, get a good job, work hard, and have a pension. We’ve seen that get dismantled. When people take jobs, which I hear all the time, it has good benefits, but it’s something that they despise. It’s something that they give their life away and time for money. They want to retire. If you enter a situation you want to retire from, it’s not the right situation. Retirement is problematic. Back in the day, when retirement first came up, people were working assembly lines. It was physically exhausting. They were working seven days a week. People were dying.

Retirement was you’ve broken down your body. That was the time of brawns. We’re in the time of brains, where brains are rewarded a lot more than brawns because we have machines and we have different efficiencies. If we keep operating, when we’re trying to retire one day, we won’t have more longevity. I get that the numbers have gone down a little bit in America due to suicide and maybe part of the food that we eat and the lifestyle that we have but still, it’s a lot longer than it was in the ‘40s and ‘50s. People are going to have 20 or 30 years of not working. That becomes not only a burden on society, but it’s also a burden on themselves because when people retire from purpose, they invite more sadness and misery into their lives. We have to redefine and recontextualize what retirement is. We have to recontextualize this notion of if you hustle, if you work hard enough, and if you sacrifice, then one day, someday you’ll be able to live a better life.

The problem is if we become habitually that way of sacrifice, which is, “I’m giving up. I’m delaying gratification. I’m working so hard that I’m exhausted. I got adrenal fatigue. I don’t see my family. I feel guilty all the time.” We go, “I did this and we finally get to retire.” I see that a lot of times. They lose a lot of important things along the way, including who they are and what’s important to them and society rewards it. Society doesn’t reward family. Society rewards work. It’s confusing. I broke down crying to my wife because we talked about some things in the past. She’s like, “You were selfish in your twenties.” She hits me with it. I was all about, “I’ve got to make more money. I’ve got to do more so I can fill this unfillable void that I’m not perfect. I want to be loved.” At the same time, I’m harming the people that I love the most.

I left the hospital after my son was born and not thriving. He was hooked up to IVs in some weird incubator and my wife is still reeling from the delivery and struggling. I went to work because I was a selfish idiot that thought that the game of life was about accumulating more things. You play that game then you retire because you’re exhausted. It was the carrot at the end of the road and Millennials reel again. I’ve seen how unhappy my family is. I see what work did because people chose the wrong work. They chose work that wasn’t fulfilling enough. I have fulfilling work, but it doesn’t mean I will show up every day and I go, “It is amazing. I love editing. Let me do this video on no sleep.” It’s not a blissful state at all times, but I already won by choosing the right work. I’m willing to deal with those things because it’s part of the process and I’m enjoying the journey.

That’s the win in life. How can you find a journey that you enjoy, that you’re not trying to escape from, retire from, and get to a different place? It’s a hard thing to do because we’re not trained to do it. We’re trained to almost do the opposite, where we get accolades and awards for doing the opposite a lot of times. I could teach all there is about the concepts of money. I’ve exhausted that inside and out. If people can go to my YouTube channel, there are tons of extraordinarily practical videos of how to start, where to plug leaks, where to improve your finances without having a budget or cut back or give up things that you want. For whatever reason, the mood I’m in and the questions you’re asking, I like getting to the philosophical construct. This is what I’ll say if you ask me another question, hard work with the wrong philosophy or the wrong perspective still equals a miserable life. It still equals potential bankruptcy. It still equals the loss of the things that are most important. We’ve come to that because we haven’t been shown a different way.

I’m thinking back to the jobs I’ve had that I didn’t like, but they allowed me to have a life with my children or do certain things. Sometimes you have to take one for the team to have a job that affords you to be able to do things you like even if you don’t love the job necessarily. Is there a change in your life when you don’t have children and you have more options? How do you look at it that way?

[bctt tweet=”Hard work with the wrong philosophy or wrong perspective still equals a miserable life. ” username=””]

There are always bridges. There are bridges that we drive over that aren’t the bridge that we want to stay on. Some people get stuck on that bridge. I worked at inbound telemarketing for a couple of years when I was in college. The gift that was no matter how many hours I spent doing that, it was never going to get me wealthy. I was never going to feel fulfilled. I washed cars. I cleaned the tar off cars. I waxed cars, but it taught me how to do a balance sheet and an income statement, how to have flexibility with my calendar, what a business looks like, how to deal with a client that wasn’t satisfied, and how to have great relationships that prefer how to hire employees. It was great, but I’m not doing it anymore. They are stepping stones.

The problem is when those stepping stones become stumbling blocks. Far too many people go, “This’ll be temporary.” What they mean is, “I don’t know what else I’m going to do and at least I’m doing something. I don’t want to face the pain of finding what I want because it’s difficult. I have to admit that I don’t have it all figured out because I don’t know what the future is like. I’m already suffering. Let me numb out and accept what it is.” It’s fine to accept what it is in a lot of ways, not when what is, is a lie that you don’t want to be.

My wife was being interviewed for this video that we’re doing from an origin story. She said, “When we were graduating, Garrett was like, ‘There isn’t a job out there for me. I’m going to create what I want.’” My youngest son at the time was nine. When she spoke those words, that immediately when she came off-camera, he goes, “What do you mean dad couldn’t find the job that he wanted so he created it?” She goes, “He’s an entrepreneur. That’s what he did.” Not everybody is built to be an entrepreneur, but as an entrepreneur, we have a deep responsibility to create a vision that is compelling and inspiring enough that people that do have to do crappy work. Stop holding onto things that artificial intelligence can handle our technology because we think that those are important jobs for people. What’s important is vision. The world has been stuck and not creating a vision. When you create a compelling vision, something that you can’t accomplish on your own, other people get to be part of something exciting, valuable, enticing or use their skills.

Sometimes entrepreneurs too come to, “This is profitable.” They settle as well and then they feel superior to the employees. They wouldn’t exist without the employees and employers. The employees resent the entrepreneur because they are trying to get a retirement plan and that’s not inspiring to show up to every day. Everybody is trading time for money. They are trying to get by. I had partners die at age 35. Getting by is crap. What about my clients? His wife got killed in Seattle on the freeway. She’s gone. She was in her 40s, a lovely woman. We are blessed each day. If we’re not going to face the pain that we’re hiding from ourselves, if we’re not going to confront the inadequacies that we think that we have, then we’re going to continue in a predictable way. Pain is like a puppet master. We know exactly where people are going to go. It’s predictable. If they don’t confront it, we can’t go below it, around it, above it, you’ve got to go through it. On the other side, it’s rewarding.

As you’re saying that, to feel rewarding, I’ve worked with people who have taken a lot of jobs where you can work virtually because that’s something that they value highly. They work for companies and leaders who treat them without respect, but they go, “At least I can work out of my home. Money is not that important. It’s hard to find other jobs where I can do this.” What advice do you give people when it’s time to cut bait?

It’s simple and hard at the same time. You’ve got to love yourself and until then, people will still mistreat you.

There is much confusion with what jobs we would love to do. I always had the golden handcuffs when I was younger. I thought that people would tell you, “This job you can’t beat. You have the greatest job in the world. You get a company car. You get this and that.” I didn’t love the job. It didn’t fit my needs. It’s hard for people while they’re in it. Once you get out and you look back and you go, “Why did I do that?” It sometimes takes time to look back to see what it is. Sometimes you feel like you’ve wasted time and how do you stop wasting that time? It’s a tough situation, but what you’re talking about is creating wealth. When we talk about creating wealth, you’re not saying to become Oprah’s wealthy type of thing. What do you mean when you say create wealth?

Creating wealth comes in five tracks. Money is one of those tracks, let’s make no mistake. It’s easy when you have money to say, “Money is not going to buy happiness, but lack of money is awful.” You can be happy without it, but it is awful. Lack of money is the reason my great grandfather left his wife while she was pregnant to get on a boat and come to America, not speaking English, to work in a coal mine. He wanted to remove the shackles of poverty and at the same time, he embraced the shock of scarcity because that is a painful seven-year separation. When you see your daughter for the first time, she’s seven years old. I can’t even fathom that. When I’m gone for a week, I’m missing my family badly that I’m a little baby. It’s insane. If you think about what we’ve accepted as this is how it is, we’re doing the wrong hard work. The hardest work is thinking about who you are, what you want, what’s most fulfilling, and there are many blocks to it. That was my conversation with my wife. She is letting me work with her to help her unveil her purpose. I’ve got some great tools and we were talking about it. It was a deep, interesting conversation.

What questions do you ask to unveil your purpose?

It’s this whole notion, the reason why it’s hard for people to unveil their purposes, they’re stuck in the two paradigms. One paradigm is what I would call playing not to lose. They’re holding onto the past, protecting what they have. They don’t like to change. The other one is playing to win. It is another form of scarcity, which is all about take and try to do better, bigger, more, and go faster. It’s all this unfillable void of living only in the future. Neither of them knows how to live in the present because playing not to lose stuck in the past and playing to win is stuck in the future, which leaves no room for enjoyment. It blocks vision. The biggest reason why people struggle with vision is that they think that they have to know how to accomplish their vision.

They think they have to have the resources to have that vision. They think they have to have the talent for that vision. I could keep saying all the reasons, but all it takes is being bold enough to speak something that you are enticed by, that you are excited by. That’s beyond your existing bandwidth. If it’s in your bandwidth, it’s not a vision at all. It’s a goal. Where people get genius is they start coming up with the excuses, reasons, obstacles, liabilities, why this vision can’t come to be, “I have a dream one night. I have this dream and it’s me directing a Broadway play, but when I wake up, I realize I’m directing myself. That it’s not exactly a Broadway play because there was only one person in it. It’s a one-man show.”

I was like, “Interesting, it’s a one-man show. I don’t act. I’m not an actor.” I say, “Who’s doing a one-man show? I’m calling Bo Eason. I know him.” He’s done a fantastic one called Runt of the Litter at one of my events. I start talking to him. I’m like, “Michael Port was an actor. He’s a phenomenal coach. When he coached me one-on-one with my speaking, I’ll call him.” He was like, “I love this idea. I tell him what it is.” I was like, “I think life for me is more about art than it is entrepreneurship. It’s about the expression of that art to demonstrate freedom, to shift the context of value creation, not to give more content. People have plenty of content. The internet is filled with it.” He said, “I love it.” We started working on it. I’m working on the one-man show. I was like, “I think I should sing during it. I’m not a singer.” He was like, “Let’s test this. Garrett, you are going to sing.” I was like, “In the end, I should dance.” My nickname in high school was Cord because of my uncoordinated feet. I’m going to dance because all I’m up there to do is say that the game is not about perfection. People think it’s about perfection. No, it’s about expression.

TTL 664 | Path To Success
The world of stocks is about big corporations that you don’t necessarily agree with – how they do business and how they operate.


If this guy from a 1,000-person town that’s white and not knowing how to dance, who can sing the songs that I write myself, that hasn’t picked up a guitar for a long can go up there with full expression to demonstrate what freedom is. To give an experience that people can laugh at with the four different characters that I act to understand where you’re playing. Not to lose what you’re playing to win, where you’re stuck in one of those or you see other people in it. All of a sudden, remove the judgment, knowing that’s blocking everything. Hopefully, I can give permission for people to have whatever their vision is because of this strange vision. It’s something that I performed a few acts for my team. I’m about to do a TEDx where I will do an act, scenes 1 and 2, showing the four characters and going through this whole process. It’s exciting. It’s to express art as a way to love humanity, not for me to go out there and go, “Can this person make me money if I help them out? They don’t have a checkbook handy. They can’t give me their credit card or Venmo me. I’m not as engaged as if they were someone who wasn’t important.” What an idiot I am. I keep seeing what an idiot I’ve been in my life and it’s a gift.

Congratulations on doing the TEDx from all that. Where are you doing it? Which one?

In Queens. I did a TEDx in St. Andrews. I happened to get two offered within a short period of time. What’s funny is when I went to do the St. Andrews’ one, it wasn’t as big of a crowd as I expected. I started getting into making it about me and I had written a speech. I rehearsed it like crazy. I was like, “That speech is about me getting views.” I’m looking at these people and how amazing they are. Why don’t I go up there and connect with them? I did a completely different talk and they rewarded me with a standing ovation. There was one other person there about half the people stood for, but I was the only one that everybody stood for. There was a woman who was like, “I’m writing that down.” I was like, “This feels good because they’re giving back the love that I’m giving to them, instead of me going up and trying to look cool or be cool or get views or validate my ego.” I’m on an interesting, weird journey. I feel like I can help people around money because there is much pain around it. I hope that my mission is bigger than that too.

You probably get a lot of experience. You do local stand-up comedy clubs.

I’ve done some reel clubs too, but I’ve done a lot of local ones.

I know improv helps a lot. Do you do a lot of improvs as well?

I’ve only done a little bit of improv. I have a friend, his name is Glenn Morshower. We filmed this commercial for Facebook and YouTube. He’s an actor. If anyone goes to the IMDb and looks up, Glenn Morshower, he’s been in more than about any other. He’s the busiest character actor. He was on Jimmy Kimmel’s 1 of the 4 guys that you know their shows but you don’t know his name. I took a little mini-course that he did. I’d like to do a more deep course. I did a little bit of improv in college as well. I’ll work on that. The stand-up thing, I got a manager and his name is Barry Katz. He’s managed Dave Chappelle for years and Louis CK. It was insane. He saw me during one of my best performances. The reason it was my best performance is that I wasn’t trying to make it about me. I was there to connect with the crowd.

I told them that comedy is one of those great things where we’re not worried about our past, not focused on our future, and uncertain that we’re in the moment. What makes comedy funny is the flaws. Comedy is not funny when it’s perfect. It’s funny because we’re pointing out the flaws of life, ourselves, society, and whatever. We laugh as an authentic expression. People aren’t faking it. You can’t fake funny type of thing. I love that immediate feedback and I love that connection that I can get with people. It was an amazing night. I’m loving doing stand-up comedy. I haven’t done much for the last months, but I’m going to be doing more of it.

Do you like comedy like Seinfeld where you are pointing out things to everybody like, “Why is it this way?” kind of comedy? Is that what you’re talking about?

Mine is all real stories, but my cadence is I get a laugh every ten seconds or so and applause breaks every three minutes and a bigger laugh every minute. A lot of comedians are in the longer story arc on a topic. I’m telling real stories about my kids, me, my family with a little twist, with a little bit extra funny that’s fabricated. When I try to tell observational humor, what I found is I would write these jokes down and I would watch specials and I’m like, “That’s similar to the observational joke I wrote about Lululemon or TSA.” I’m like, “There’s almost like a collective consciousness there.” What I’m sharing are real stories from my life. I was writing a joke about I decided I’m not into sports at 41 anymore. The reason is I’m likely to hurt myself and injure myself. I’m probably not going to win. I’m a little bit past my prime. It’s winners and losers. I was like, “The reason I worked out is for the most important sport in the world, sex. If you do it right, both parties win.” It’s the initial piece of a joke there, but there’s some real truth in my head to that. I was like, “That was my favorite sport by far. I tell my wife that all the time.”

Is she laughing as much?

She laughed, but sometimes she’s like, “I don’t know if that joke is quite funny.” My comedy makes her nervous sometimes because she’s like, “Can we keep that one to the family? I know it’s funny, but can that one stay here instead of onstage?” I’m like, “That’s cool, “ but she’s been laughing hysterically at my stand-up sets, which is awesome because sometimes she gets to hear the jokes before they’re funny. I’ll test it on her and she’s like, “I don’t know if that one is ready yet. You might want to go back to the drawing board.” She’s authentic about it and I appreciate that.

[bctt tweet=”We have to redefine and recontextualize what retirement is. ” username=””]

Do you have a fear of flopping at all? Do you have fear when you’re up on the stage?

Onstage, not at all, but before the stage, definitely. The first time I did stand-up is an open mic, six of those people I knew showed up. The reason they showed up is like, “I don’t want to back out. I would invite people that are local.” They showed up. My friends were phenomenal and I was nervous. I peed three times before I went up there. I was like, “I can’t back out.” I was stressed. I don’t remember being that stressed, but it felt amazing while I was on stage. It was a little bit more robotic than I am now because it was joke-to-joke. It was preplanned versus with the crowd, but it was good enough that a comedian came up to me and he goes, “You should open mic for us.” I was like, “I’m in.” When I did it at a business event out in Genius Network of Joe Polish, I got up and did stand-up at the annual event. I was nervous because it is a business conference. They’re not expecting a comedy. It’s a harder venue, but it went fine. It went well. The only time I’ve flopped in comedy is to flop off stage. I don’t feel like I need to put the crowd through the pain. I’ve already tested these things out to a large degree.

I had a set in Vegas that didn’t go amazing. There was some drunk woman there and I didn’t manage the crowd that way. That was distracting. The jokes didn’t hit and it threw my timing off. I listened to it later. It was still good. We still got plenty of laughs compared to what I could’ve done. I didn’t adjust. I went preplanned. I didn’t stay with the crowd. It’s learning those lessons. I’ve only had one that was an open mic and I decided to tell a story. I got some laughs, but it wasn’t bad. People weren’t in pain. I’ve been that person in pain in the crowd. You’re like, “Please leave the stage. Why are you still going?” If I ever get this bad and off one night, I exit early. They don’t know. They didn’t know that I was supposed to be ten minutes and I walked off in two minutes. I did them and me a favor. I’ll go back and work on it.

You came out with What Would the Rockefellers Do? That’s not that long ago. You’re talking about wealth. All the things that you write about and then you’re a comedian at the same time. Are you going to start being a comedian that talks about wealth? Are you going to get out of wealth?

I’m not leaving wealth. Comedy is a hobby. Comedy, doing stand-up, that’s for the stand-up’s sake as a hobby. It doesn’t move the needle. We’ve got plenty of comedians out there that are hysterical. I’m not going to add to the world by doing that, but for people to be able to be entertained first and then deal with their money, nobody’s doing that. That’s the gift. That’s what I’m bringing. It’s been fun for me.

Most of your jokes are wealth-based.

No, they’re family-based. It relates to everybody. Not all my jokes will be able to be in my speech. I lead with humor a lot of times in my speeches. I had Keith Yackey introduce me to this. He does a lot of stand-up. He’s a business guy and I spoke at his event, Amplify. This is how I eventually jumped into stand-up. He introduced me, “Our next speaker is effing hilarious. He’s one of the funniest people I know.” I was like, “What? I’m about to give a 40-minute financial talk.” I got up there and I did 3 to 4 minutes of financial jokes. They were mostly self-deprecating. I was like, “Keith, that was the second-worst bio introduction I’ve ever had. The one person that kept calling my book Killing Sacred Crows. That was worse though.” It went into, “Was it scarecrows or scared crows? Either way, it doesn’t make sense to me.”

People were laughing. I called my buddy who’s a comedian, Marcus, he was a runner up on Last Comic Standing and I said, “I want to do some stand-up, will you come work on a set with me?” We spent two hours together and he goes, “I think you’re ready.” I did the set and it went well. We started meeting a couple of times a month. I like to test my jokes with him. I like to have him tell me, “Go back to the drawing board there, find a tag for that.” He helped me with that. I had twenty years of the stage before and that helped as well. This one-man show integrates comedy. It begins with entertainment because the one-man show is massively about finance without anyone feeling like it is. It’s here for a contextual shift, not for a bombardment of content.

That contextual shift moves from selfishness to value creation moves from a miser to a mindful manager. It’s exciting because it can have a much greater reach and a much more lasting impact. I’m not telling them something, they’re experiencing it. I then take them through a short exercise where they figure out what their block is and what’s holding them back. It’s insane what it’s doing and I’m testing it. I’ve had to bring crowds back because of this conversation that comes up once they have the epiphany and the shift. How egotistical this might sound, but I’m not this person. I’m looking at Shakespeare. He gave a gift of love to humanity where we could learn through poetic shows, but there were lessons in them. There was real humanity in them many times.

When you’re talking about what holds people back, that ties into the research I do for curiosity. I found what holds people back from being curious. What do you find holds people back when you do those exercises?

I think survival holds them back. They’re in survival mode and doing the best they can with where they’re at. Their fear of making mistakes and what other people will think about them as the next strongest thing on them. They want to take care of their family and put food on the table, so to speak, which is easy to do that in America but to check the list of what it means to be successful from a societal standpoint. That fear, that scarcity is a liar that creates unintentional selfishness and it leads to survival. Therefore, they’re not willing to dream because that’s scary. What if it doesn’t work out? What will people think of them? Who will be threatened by that, that will no longer be their friend or say something negative about them? It’s all this being caught up in the external world of what other people think. A lot of those people worry about what they think. That might be family and friends, but the rest of them. We think they’re thinking about us and they’re not. They’re too busy thinking about them. Whatever feelings they have about us, it’s only because we’ve shined something they didn’t deal with on their own.

I’m doing this one-man show and I’m acting in front of my team, which some are on Zoom and some are in person. I didn’t give the context because we didn’t have a reader or we didn’t have the slides. I could see that there are moments that people are a little bit uncomfortable, but I went through the thing to the other side and one of our coaches, I could tell it completely shifted his mind. He kept going, “How did you that? Where did you come up with that?” He was grappling with it. Because when I’m an actor doing these characters, people don’t have to take responsibility at the moment. They can look at it and say, “I know someone that’s like that.” Eventually, they can then go, “This is where I’m at when I’m at my worst.” They don’t have to say it out loud. They get to feel it for a minute. They get to see that all those characteristics in the wrong paradigm that lead to misery, are the same characteristics in the right paradigm that lead to what they want. It’s not that they have to become a different person, they have to shift the paradigm to one that limits their self-expression due to survival, to one that expands their freedom and value creation because it gives them permission to thrive.

TTL 664 | Path To Success
Path To Success: When we try to forfeit our responsibilities and our freedoms because we think someone else cares more about our money than us, we’ve already lost.


That’s something that from the time we’re kids, we have incidences that have us believe that we can’t do it, that we’re not worthy. There’s something bad or wrong or different or that we could harm others. What would someone think or what if we fail? There is much insecurity that comes. We don’t resolve those childhood issues. I got hit by a car when I was three. What did that tell me? If I’m not perfect, I hurt people because I saw my dad come in his coal mining outfit to the hospital with dust all over his face. I saw my mom bawl her eyes out from there to the hospital. When I was five years old, I was molested by two older boys. I never wanted to talk about that. I want to hide that. By hiding that, what does that make me do? “I’m not going to show who I am. I’m never going to be self-expressed because I don’t want to have people think differently of me or say something about me.” How many people have gone through that stuff and we’re hiding it? We’re pretending it doesn’t exist and it’s keeping us from who we are. Are you deceiving me? I’m going to dance, but that’s an ultimate form of self-expression. The song that I’m singing, I wrote.

Not only am I singing the song, but I also wrote the song. I hope that it comes out in one of the papers where they critique my abilities, where they say, “I don’t know about the talent,” because if they do, they miss the entire purpose of the show and it doesn’t matter. When you are a kid, you dance, you sing, you do stuff. You’re not worried about how you sound because you’re expressing love and freedom. It’s time to get back to that. That’s what humanity needs. That’s going to heal the planet more than anything is if we can get to that expression. Whatever small drop I can do in the ocean of that, I’m winning because I get to play that game. I’m winning because this has opened me up to love more than ever before. The human beings, particularly men that have said, “I love you or much love, buddy,” that I said, “I love you.” I can feel what that’s doing for them to get permission to love themselves or know that I’m there for them. The letters that I’m writing to people, this is the work that we forget to do because we get caught up in society or because we’re embarrassed about it.

I realize there’s nothing anyone in my family can do to embarrass me. I get these things I can do to embarrass them, but sometimes that embarrassment is the thing that we hold most precious and that we talk about and laugh about later. I have a friend who died, Sean Stephenson. He always said, “What’s funny about this?” This dude was three feet tall, with osteogenesis imperfecta. That’s coming to my head multiple times, what’s funny about this? Comedy is healing. It is such a gift. It’s fun, but it’s healing because it allows us to look at something that we’re scared to look at. There’s some deflection in that too, but there’s also healing if you’re willing to go through that. Who knew I would talk about all this stuff? I don’t think I’ve ever talked about any of this on a show, but here you go.

You are the first person I asked a lot of crazy questions and you know all of the things you talked about, what hold people back are the things tied closely to my research and curiosity. What holds people back are fears and all the things we tell ourselves and our family and all those things that you mentioned of our childhood tied into exactly what I researched. You and I’d have plenty to chat about, but we ran out of time. We never did get to go to these Seven Foundations.

People can go to my YouTube channel, Garrett.Live on the internet browser or look me up on YouTube. There are five videos a week coming out and they’re not about this stuff. If I can to include this, the biggest gift that I’ve been given in life is I got to experience unconditional love. I have this neighbor, I’m looking at her obituary card hanging on my wall. Her name is Anna May Web. She was always fascinated with me and laughing at me and always like, “Let me talk and play trucks in her front room.” She was great to my grandfather and me. Before I had any evidence that I was going to be anything or do anything, before I was still pooping in diapers and all that kinds of stuff, he had an irrational belief in me. Irrationally like, “There’s something in me, I’m going to be great. I am great and then unconditional love.”

If you can have those combinations of unconditional love and irrational belief from someone in your life, it is magical. I think about where I can be the person that has irrational belief before there’s already evidence of success materially or in the world or acknowledgment where I can love on and invest in someone with time. My grandpa took me on TV calls as he would be a TV repairman when he wasn’t in the coal mine. I’d go to the shop and watch him do that. We’d drive in the rain and he would pretend that his dog was driving and he’d be driving with his knees. Those have an imprint on me for the rest of my life to feel loved.

I’ve had conversations with my kids where I said, “I love you no matter what. There’s nothing you could do in this world that would make me love you any different, any less. I could be disappointed, sad, frustrated or angry because of the actions you take, but you don’t have to earn my love.” They still are having a hard time understanding that they still believe they’ve got to earn it. They had it because they’re part of the story. They’re part of love. I think that we need more of that than we need to get another strategy for a 401(k) because that’s easy. I can help with the money stuff. It’s easy. It’s easier than we think because people have tried to complicate it, but it’s not as complicated as we think.

A lot of people here could use help with all of the things that you talked about. This has been a fascinating show and you are fun to chat with. I’ll have to catch one of your stand-up routines. I have been to Joe Polish’s event, but I missed it. Hopefully, I’ll catch one of those next events that you do. I can’t wait to hear you sing and see you dance. Thank you so much for being on the show. Is there some link or something you want to share so people could find you? We mentioned you’re on YouTube, anywhere else you want them to check?

If they want to get one of my books at no charge, I’ll give them two of my books. They can download Killing Sacred Cows and What Would the Rockefellers Do? at There are cashflow guides in there. Since I didn’t give out a lot on this, I want to give those gifts. Obviously, you’ll be subscribed to our list and we email about seven times a month. Every seventh email, we offer to hire us or buy something from us. You’re on that for seven months. If you don’t do anything, then there are not many emails that come your way. You give me your information, we can build a bridge of a relationship. You get to download some great things. If they’re valuable to you, you’ll know how to work with us. If they’re valuable in content, then great. We only have a certain capacity anyway, but I do want to build a relationship with people.

I never get to hear that level of honesty. I appreciate that, Garrett. This was fun. Thank you for being on the show.

Thank you for having me and thanks for creating the space for me to share this. You’re an amazing listener and I’m an amazing interrupter, so I appreciate you letting me go off there.

It was great and I thoroughly enjoyed it.

I’d like to thank Garrett for being my guest. You can get anything you need to know about Cracking the Curiosity Code or the Curiosity Code Index on the site at and at I hope you enjoyed this show and you join us for the next episode of Take The Lead Radio.

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About Garrett Gunderson

TTL 64 | Path To SuccessGarrett Gunderson is called a “financial genius” in entrepreneurial circles, but he wasn’t born with a silver spoon. In fact, Garrett’s blue-collar roots are what make him so passionate about helping entrepreneurs build Economic Independence. Garrett is the author of the New York Times bestseller Killing Sacred Cows: Overcoming the Financial Myths That Are Destroying Your Property. His most recent book is What Would the Rockefellers Do?: How the Wealthy Get and Stay That Way, and How You Can Too.


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