129: From Financial Advisor to Stand-Up Comedian with Garrett Gunderson

The Business of Meetings – Episode 129: From Financial Advisor to Stand-Up Comedian with Garrett Gunderson



We are delighted to have Garrett Gunderson joining us today to talk about his transition from being a financial advisor to becoming a stand-up comedian and doing a tour on stages across the US!

In this episode, you will hear Garrett talk about his journey and the bright future he is building for himself.

We hope you enjoy today’s inspiring conversation with Garrett Gunderson!


A modern-day “renaissance man”, well, maybe.

An Inc 500 founder of a financial firm and amateur barista.

A rookie fly fisherman and Wall Street Journal #1 Bestseller.

A public speaker who’s delivered hundreds of keynotes, and a mediocre guitar player at home.

A bow hunter, Traeger grill semi-pro, former cross-fitter (emphasis on the former), and a whisky sommelier, which is real, and just as douchy as it sounds.

But maybe the best way to know me is from a few notes my wife wrote:

  • A man who can only drink tequila under supervision.
  • A man who will stop at nothing to provide his wife food if she gets HANGRY-self-preservation really.
  • A dad who was totally cool with letting his sons go anywhere with him, in any costume they may have on! (Yeah, a client offered my kids $100 to knock on every door in the neighborhood with the three of us sporting Spider-man costumes saying “the neighborhood is safe”. My costume was too small, and more Moose Knuckle Man than Spider-man, but hey, that $100 spent the same.)
  • A man who can’t fix a toilet, but can help you become financially independent so you can hire someone else to do it for you.
  • A man who supports his wife’s meditation, even if she is just sleeping.
  • A brother who bailed his sister out of jail, while almost going to jail himself in the process.
  • A father who loves and adores his sons for exactly who they are.
  • A son that loves his parents with all his heart.
  • A man loyal to his family and friends, but most of all his values.


Garrett thinks comedy was his first love. He came from a family that was Catholic on one side and Mormon on the other, with love and laughter as their universal language.

Garrett’s journey

Garrett got involved in financial services when he was nineteen years old. In 2000, when the markets started dropping, he had the time to go places and meet people who were decades ahead of him in the financial game. So he spent 26 months interviewing people in various areas of finance.

Scaling his business

From 2000 to 2006, Garrett scaled his business by partnering with three other people. Learning from each other, positively challenging one another, and creating a bigger vision together helped them grow the business. Sadly, two of his three partners died in a plane crash in 2006.

Working harder

Garrett tried to make up for the loss of two of his partners by working harder. However, that negatively impacted his family life. So he had to let go of certain things and realize that he was not responsible for everyone. Then he created a firm, brought in financial people, and wrote a book.


He made many mistakes along the way. He made most mistakes because he was not clear about his life, so he let opportunities distract and derail him.

Four areas of guaranteed efficiency

After doing all the interviews, Garrett concluded that although there are no financial guarantees when investing money, there are four areas where you are sure to be efficient with money and get a return on it.

Those areas are:

  1. Saving on taxes
  2. Saving on interest
  3. Removing all non-performing fees from your investments
  4. Removing all duplicate covers and improper structures from your insurance

Writing books

Garrett hired a ghostwriter to write his first book because he thought having a book would make him seem cooler than he was.

He has two books coming out next year. He did a lot of writing for one of them and loved the whole process! The other one he co-authored with someone else.

The future of finance

Garrett hopes that his new book helps to make the future of finance, business, and government about connection and compassion rather than competition and destruction.

Quality of life

Garrett believes that if people can enjoy their lives and make their quality of life a priority, money will become a by-product of a life well-lived rather than an excuse against it.

Confusing love and money

Garrett believes that people have been misguided to confuse love and money. So they chase money to validate something they have not accepted in themselves.


Competition will appear to be the norm until people learn to love themselves and create a life of value creation where they have a sense of purpose and are sure of their place in the world.


Collaboration is much more fun than competition. Collaboration requires trust, and trust begins with ourselves. We need to trust ourselves to invest fully in who we are and deliver value consistently.

A different conversation 

Garrett wants to encourage people to have a different conversation about money and help them understand where there might be limitations in their goals.


Garrett feels that there are some positive aspects to school, but there is also rigidity that might not persevere in today’s world.


Debt is a trap. Garrett is writing a comedic book about debt called Life After Debt. It covers student debt, loans, and how people finance their future.

Becoming a comedian

As a kid, Garrett loved telling jokes! In 2005, he was at a formal dinner in Costa Rica, drank too much tequila, and ended up at the mic telling bad jokes. Then, in 2017, after returning from a summer in Italy, he felt relaxed and kept making his wife laugh. He also told some jokes at his next financial presentation and made the crowd laugh, so he felt ready to start telling jokes on stage. Then, a comedian friend helped him write some jokes and allowed him to start opening for him at his shows, and someone discovered him. Garrett filmed a comedy special in 2021 that will air at the end of 2022.

Transitioning to comedy

Garrett treats comedy as a profession. He received training from friends, professional coaches, and speaker-training programs. When made the transition to comedy, he felt he already had stage presence. He continues to refine and improve his presentation.

His tour

In 2021, Garrett did a tour of 15 or more cities across America.

Garrett’s goal

Garrett would like to use performance and entertainment to educate people. He would like to plant a seed of hope, feel connected, and help people to be more expressed. He wants to reach a billion people, inspire them, and touch their hearts with his work.


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Connect with Garrett Gunderson

On his website

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Eric Rozenberg

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