Talk Money to Me: Chris Guillebeau’s Side Hustle Strategy

Chris Guillebeau isn’t one to follow convention.

Guillebeau, the author of the best-selling book $100 Startup took on countless gigs in order to reach his goal of visiting every country in the world by age 35.

His new daily podcast is all about the side hustle—something you do for love because it has the potential to make you money while you’re doing something else. (A book on the same subject is out in September.)

While Guillebeau says that he has a pretty typical approach to investing today, that wasn’t always the case.

We asked for his best tips on how to put your money to work while forging your own path.

Pay to play

“I’m a big believer in having a ‘slush fund’—a separate account that’s either for fun or for something that you’re saving toward,” he says.

“I’m a big believer in having a ‘slush fund’

That’s especially important if you have a passion but not necessarily a high income—as was the case when Chris was doing a lot of traveling.

“At the end of the year, when I’m doing my finances and figuring out what to contribute to my SEP IRA, I also set aside money for next year’s travel,” he says. “When you have a project that’s not a huge money-maker, it helps to have the money, going into it.”  

Invest in your education

Chris taught himself about investing back in college—not in a class, but in the school computer lab, day trading with the cash he received from a student loan.

“I don’t know if I ever made a lot of money, but I didn’t lose a lot of money,” he says. He guesses that he broke about even with the $15,000 he was working with throughout the year.

“I was hardly an expert, but I read everything I could—the library got the Wall Street Journal and Barron’s,” he says. “I walked away feeling like I had this unique experience that could help me later.”

Retire like Chris Guillebeau

Chris now contributes annually to a Simplified Employee Pension Individual Retirement Fund (or the much simpler-to-say “SEP-IRA”).

It’s a relatively common choice for people who are self-employed or who own their own businesses (in other words, people who can’t benefit from a company’s 401(k)), in part because you can contribute more to a SEP-IRA than you can to a traditional or Roth IRA.

Chris’s account is invested mostly in index funds—usually in a standard split of 60 percent stocks and 40 percent bonds.

“That’s pretty basic,” he says, “but it’s good advice for most people.”