Side Hustle Your Way to Success with Chris Guillebeau

PT and Chris GuillebeauChris Guillebeau is the bestselling author of the books The $100 Startup, The Happiness of Pursuit, and The Art of Non-Conformity.

Chris is also the founder and host of Side Hustle School, a daily podcast with more than 2 million downloads per month. Chris just released a new book based on this topic called Side Hustle (what else?) which you can purchase on Amazon today.

During a lifetime of self-employment and side hustling, Chris visited every country in the world (193 in total) before his 35th birthday.

So let’s dig in. Let’s meet today’s Master of Money.

Listen to the Episode with Chris Guillebeau

I hope you enjoyed that. A big thank you to Chris for giving us the gold today.

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Unlocking Opportunities

Being intentional and understanding priorities has always been important for Chris. Throughout much of his adult life, he’s focused on his goals and what finances were required to make those goals happen. He’s made decisions that would unlock those opportunities for himself. He wanted to visit every country in the world and chose to really invest in that and not have a mortgage or own a car at that time to make that goal a reality.

You might not have grand plans like visiting every country but you might want more for yourself. You might not hate your job but you just know that there’s something better out there. Chris says it’s important to pay attention to those feelings and experiment. You don’t have to know everything in the beginning. Chris didn’t know all along what he wanted to do. He figured it out through experimenting.

Bad at Geometry, Good at Accounting

Chris has always like budgeting and saving. He was terrible at math and couldn’t understand geometry, but it all clicked when it came to accounting and bookkeeping. In 1995, when Chris was 19, he took some student loans and used them to day trade in the computer lab of his university. This is not a recommendation but he did it! None of it really paid off but he enjoyed the process. While others were writing their term papers, he was day trading.

Early on, Chris’s dad created a structure in his life by giving him an allowance for chores he did. The more chores he did, the more money he had the opportunity to make.

From College to Side Hustle to a Master’s Degree

It was right out of college that Chris began his entrepreneurial endeavors. He realized he wasn’t good at working for other people, even though he really liked to work. He knew he had to find a way to provide for himself so he began various side hustles. That lasted for about a decade. He started out with selling online auctions. He and his wife lived in West Africa for four years and were aid workers there. They weren’t getting rich but it was sustainable. Chris related his money to happiness; not in a “the more money I have, the happier I will be” way, but more so, what was the base level that they needed?

He focused on the work they were doing in Africa and then came back and got his Master’s degree and then eventually started his writing project.

Cruises and Retirement

When his tenth anniversary was coming up, he wanted to go on a cruise with his wife. The whole trip was about $3,000, so he saved $300 a month and that was super motivating. He liked seeing the money accruing. It was the same with retirement savings. He began with a Roth IRA and currently has a SEP IRA.

Web Design, SEO, and Affiliate Marketing

Chris has never been fully employed by anyone other than himself. He’s side hustled through learning about web design, SEO, affiliate marketing, Google Adwords. He was never amazing at any of it, but he was good at figuring out how to take advantage of new things until they were optimized and taken over by professionals.

A Legal Procrastinator

Chris has a CPA to do his taxes because he hates it and is not good at it. It takes him hours and hours. He just found out a few years ago about filing an extension and wishes he hadn’t because now he procrastinates on something that already stresses him out. Legally, he has four or five different business structures, and he runs his event which he treats as a non-profit, so it’s very complicated.

For someone who is very detailed oriented and analytic, it might sound like no big deal. It’s harder for Chris and just not something he likes handling.

Chris heard about Quickbooks and how it can be connected to a bank account and everything can flow easily and simply that way. Well, he’s now been paying for Quickbooks for 2 years and hasn’t set it up yet. He needs to hire someone for that, too!

Banking and Investing

Chris uses Chase for his banking services and Vanguard for all his investing. He doesn’t pay much attention to Vanguard, it’s all on index funds. He has about 50% stocks and 50% bonds. It’s a little more conservative than some people recommend, but as an entrepreneur, he feels like since he’s taking a certain amount of risk in his career; most of his reward will come through his investments.

Most of his goals relate to what he wants to do with his books or his career in some way. He doesn’t have a specific big financial goal because he loves working and doesn’t plan to stop. He hopes he never has to stop doing what he’s doing.

Side Hustle School

Side Hustle School is directed at people who have day jobs and want to make extra income. Chris feels like those types of people are under-served. They receive messages like “you should quit your job” and some of them just can’t do that. This project provides a counter message to that. The point is to create a new source of income, security, stability, and confidence. All benefits and no risk.

Is there a recipe for side hustle success? Well, the five steps are:

  • Learn to create ideas
  • Understand which of those ideas are best
  • Getting things ready to launch
  • Launching those ideas into the world
  • Regroup and refine

Everything Chris does is designed to be very practical and helpful. And with the economy leaning toward the side hustle being necessary, it’s good to have that security. Whatever financial goal you have, you can apply that extra income too.

You can go to the Side Hustle School website to learn more about the book, listen to the podcast, and learn about Chris’ upcoming events.

Show Notes

Time Stamp:

  • 01:55 – Giving up a mortgage and a car to see the world
  • 04:14 – Day trading in the computer lab at the age of 19
  • 07:26 – How being a bad employee led to a Master’s degree
  • 08:45 – Watching the money accrue
  • 09:53 – Not amazing at side hustles but just good enough
  • 13:20 – Taking investment risks as an entrepreneur
  • 15:52 – You don’t have to quit your day job

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This show is part of the FinCon Podcast Network and was produced by Steve Stewart.

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