Side Hustle School

Entrepreneur Chris Guillebeau’s Formula for Creating a Side Hustle in 27 Days

Author, speaker and entrepreneur Chris Guillebeau is best known for his renowned books, “The $100 Startup” and “The Art of Non-Conformity.” He is also an expert travel hacker, and host of the annual World Domination Summit in Portland, Oregon. In 2017, he embarked on a new project, Side Hustle School. His latest book, “Side Hustle: From Idea to Income in 27 Days,” is available now.

Side Hustle School is a daily podcast, traveling workshop series and the previously mentioned upcoming book designed to help entrepreneurs learn how to create a new source of income, all while keeping their day jobs.

StartupNation talked with Guillebeau to learn why you need a side hustle, how to use Side Hustle School to launch your project and more. The following conversation has been edited for clarity.

StartupNation: Who is Side Hustle School for?

Guillebeau: Side Hustle School is for everyone who wants to create a new source of income without quitting their job. It is not necessarily for people who are already full time entrepreneurs, people already self-employed or people who are 100 percent sure that’s what they want to do.

In the past, I’ve done a lot of work for entrepreneurs and aspirational entrepreneurs, but I really felt that there was this huge market of people who didn’t want to jump off the cliff and take a big risk. They love the idea of having some additional source of income, but I really felt that no one was serving that market. My whole focus is to speak to those people and to provide something a little bit different from the traditional startup advice or the traditional entrepreneurial advice.

StartupNation: Why was it important for you to create Side Hustle School?

Guillebeau: Side hustles are something that I’m somewhat of an authority in, and are something that people really want. Last year, for example, I had a book that came out and I did a 30-city tour. On that tour, I would talk for half an hour and give a speech. I would talk about side hustles for maybe two minutes of that 30 minutes, and literally 50 percent of the questions afterward everywhere I went would be about side hustles. I knew there was this growing interest in side hustles, and it’s partly because of an imperative. It’s probably because people realize, ‘Okay, the world has changed and there’s no job security, and even if I do want a traditional career, there’s not necessarily this long-term career security, so I need to make my own.’

There’s a lot of opportunity. There is a lot of possibility, and I have seen over and over how empowering it can be for someone to start that hustle for the first time.

I even feel that way myself. I especially see that with people who are doing it for the first time. It just brings this new element of ownership to them, and pride and confidence.

Chris Guillebeau
(Chris Guillebeau)

StartupNation: When starting out, how can someone create both a successful and profitable side hustle, while also eliminating fear of the unknown? 

Guillebeau: Right from the beginning, let’s just remove fear because that fear is attached to risk or it’s attached to something you haven’t done before. With the kind of side hustle that I am talking about, I’m not talking about the gig economy. I’m not talking about being a driver for Uber or Lyft. I’m talking about something where you’re actually creating an asset for yourself and creating something that can grow. I’m talking about doing it in a way that doesn’t cost a lot of money and doesn’t take a lot of time. So if it doesn’t work, the worst thing about it is that it doesn’t work, and you learn from that and you go on.

Now as for the part about you have ideas but you don’t know how to take action on them, that is exactly what I’m trying to address with the Side Hustle School show, and there is a whole arch to it, with a different story every day.

I’m building a narrative structure where we show people how to find good ideas. Ideas are everywhere, but how do you know which ideas are most profitable? That’s the second part. The third part is the ingredients or fundamentals of ‘How do we take that idea and put it into action?’ It kind of unfolds along the way.

Related: Unlocking the Secrets of the $100 Startup with Chris Guillebeau

StartupNation: Side Hustle School encourages daily activity while keeping your day job. How can people remain productive, motivated and dedicated to their side hustles day to day?

Guillebeau: I think it’s really important when you’re picking that idea in the first place to pick something that you’re actually excited about. Often, what you do for your side hustle is a little bit different than what you do for your job day job, or it uses a different part of your brain. If you’re in front of a computer all the time, maybe it’s not something in front of the computer, or it’s a different kind of work.

I think it’s really important to not choose something just because you think it’s going to be profitable. Profit is very important, of course, but it’s important that you do something you actually look forward to and it’s not a chore. You know yourself best, you know what you’re excited about and what you’re interested in.

The essential challenge of figuring out what is the best hustle for you is finding what is the intersection between what you like to do, what you’re excited or passionate about, and what also has value to others.

What can be profitable? The search for that is probably 70 percent of the work.

StartupNation: How do you hope that the daily Side Hustle School podcast will inspire entrepreneurs to spring into action in order to make their dreams a reality?

Guillebeau: The podcast is definitely the whole foundation of Side Hustle School. This year, I am 100 percent focused on this project to the exclusion of everything else, and that’s unusual for me. I’m starting with the podcast, but then next month I am beginning a workshop series.

I’m just doing four cities next month, but my goal is to take it all across North America. In that workshop series, it’s a two-and-a-half-hour intensive session where I am teaching this process.

People come with ideas and leave with everything they need to start that hustle within 27 days.

This fall, I have a book coming out also called “Side Hustle,” and I tell some of the stories that are on the show but then also share this specific method and step-by-step formula.

StartupNation: What can attendees expect at your live Side Hustle School workshops that they might not get from your podcast or blog content?

Guillebeau: It’s hands on, I’ll be there the whole time, it’s small and it’s intensive. I do big book tours, and there are usually a couple hundred people at each event, which is great. The workshop is going to be small and intimate, so everybody will have a chance to ask questions. The main difference is that on the podcast, it’s five to 10 minutes long every day and I definitely want it to be valuable. That’s important to me, that people can listen to the show and actually truly feel like they’re being helped through it.

If you come to the workshop, I’m teaching a process for two-and-a-half hours, so it’s quite different. I’m not just telling stories, I’m talking about things like, ‘How do you find ideas?’ ‘How do we actually put together a website?’

It’s hard to answer those questions in six to 10 minutes every day, so my goal is that people who are really excited or really want to commit come to the workshop.

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StartupNation: Anything else you would like hustlers to know?

Guillebeau: I’m just so excited to be doing this. I’m very happy that people are responding well to it. I do believe that this is an underserved market, and a lot of the traditional advice about startups doesn’t necessarily apply to people looking to start a side hustle. I’m hoping that Side Hustle School is a breath of fresh air for all of those people.

Learn more about Side Hustle School, and follow Chris on Twitter, Facebook and Instagram.

“Side Hustle: From Idea to Income in 27 Days” is available now at fine booksellers and can be purchased via

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