Chris is The New York Times bestselling author of  “The $100 Startup,” “The Happiness of Pursuit,” and “The Art of Non-Conformity.” He is also the founder and host of Side Hustle School, a daily podcast with more than 2 million downloads per month.


I was fortunate enough to speak with Chris Guillebeau just hours before the ninth stop of his 100-city book tour in Atlanta.  

We’d caught up just two days before to coordinate a time for an interview, and at that time he was across the water in London – you guessed it, on yet another tour stop for his latest book, “Side Hustle: From Idea to Income in 27 Days.”

 You start to get the sense that he’s been doing this for a while. In fact, it’s been his entire life.

Here on our blog we often highlight the stories of successful freelancers and side hustlers, and there isn’t anyone who embodies that definition more than Chris himself.

Fun fact: Chris even worked as an aid volunteer for four years in West Africa and supported himself by freelancing at night. It’s true determination that allows him to tell these kinds of stories, but his way of life also breeds an expert perspective for turning an idea into a business, managing your time and passion, and the know-how to make a living from your side hustle.

What has some of the early reception been from your latest book, “Side Hustle: From Idea to Income in 27 Days”?

Chris: I’ve just finished stop number nine, so I’ve got 91 more [cities] to go, but I actually began this kind of touring eight years ago when I started writing books and connecting with my community.

On that very first tour, I went to all 50 states, and it was just a great experience because I got to meet lots of different folks who are doing awesome stuff. I love New York. I love San Francisco. I live in Portland, but it was also great to go to middle America and meet regular people who might feel a little bit disconnected.

“I created this method that people can follow without taking on a risk in order to create that freedom project for themselves.”

I believe in this project, and I want to take the message out to folks. Being a side hustler, at least the way I’m trying to conceive of it in the book, it’s not about having a startup, it’s not about having a big company. It’s not even about being a “entrepreneur.” I’m really careful about not using that word too much because a lot of people are intimidated by it, or they actually love their job.

They’re happy working for the right company or organization, but they want to create more freedom for themselves and have options and security. So that’s what the SIDE HUSTLE book and process is about: helping people go from idea to income in 27 days.

I created this method that people can follow without taking on a risk in order to create that freedom project for themselves. And every night, I’m talking about this in a different city.

Could you explain the distinction between entrepreneur, freelancer, and side hustler? Also, why you think it’s important?

Chris: Yeah. I think the distinction is threefold. Everybody knows what an entrepreneur is, that’s essentially the Silicon Valley Model of raising money and having employees.

For a long time, there’s been a lot of entrepreneurial books and resources that are essentially telling people, “This is what you should be doing. And if you don’t actually want to quit your job and be an entrepreneur, then something’s wrong with you.” You know? Like you should feel ashamed or something.

At the same time, right now there’s this increasing emphasis on that so-called gig economy. If you’re driving for Uber or doing something similar, ultimately it’s just another part-time job because they control everything about how you do it, they cap your income, and so on.

They control all the competition, and if they don’t like you, they can kick you off the platform.

So I’m trying to actually help people do this third way – which I’m calling the side hustle. I know ‘side hustle’ is a term that people use in different ways, but the way that I’m trying to use it, I’m speaking about creating an asset for yourself. It’s about being able to make something that has the potential to earn money for you, and to work for you. So obviously, creating an online course, using Skillshare or another platform, is a great example of that. I’m trying to nudge people towards this kind of focus.

Something, in particular, you’ve mentioned before is about turning skills into a product. What are the necessary steps to make that happen?

Chris: I would say the first thing is to look at the skills you already have, and uncover what you’re good at. Maybe you went to school to learn a certain skill, or you acquired experience in some area at your day job. Maybe it’s just something people ask you about because they know you’re passionate about this hobby or pastime.

Looking to those skills is more important than trying to acquire a bunch of new skills. I feel like people are always saying things like:

“Oh, I should make an app, because I hear people talk about making apps.” Then I ask them, “Do you know how to make an app? Are you a web developer?”

If so, that’s a great idea. If not, then there’s probably something else you should be doing.

So look at the skills you already have. Then, the second thing is to learn where good side hustle ideas come from.

This is a skill of its own, and it’s actually not that hard to acquire. If you can learn this skill – which is basically about being curious and understanding the power of observation — this can serve you well for the rest of your life, no matter what you end up doing.

So then, it’s just what you said. Try to help people go from idea to offer.

Oftentimes when people do this for the first time they’re like, “I’ve got this business idea.” Everybody in the world has a business idea. But people don’t buy ideas. If you think about it from the perspective of being a consumer, you don’t go to the store and buy an idea.

You go and you buy a product, or you buy a service. That’s it.

I want to help people think less about ideas and more about offers. What are you going to sell? What are people going to purchase? What do they get for their money? How will they give you money? This is what the 27-day process in the book will show you.

I also want to help people who are busy, don’t have a ton of free time, and can’t invest 20 hours a week in something that doesn’t work.

But if they could invest maybe 20 to 30 minutes a day on something that they believe in, would they do it? I think a lot of people will.

How were you able to start your side hustle? What was the first indicator that you could turn a skill of yours into a product or service? What was that first step?

Chris: Well, I guess for me, I’ve never actually been in the corporate world, so I’m not necessarily like all the people I’m trying to serve with this project.

“For me, it’s been a 20-year side hustling journey of not having a job, but having a series of little projects.”

When I was pretty young, I realized I need to make something for myself because I’m basically unemployable.

And so I learned how to sell things on eBay, and then I learned how to do some simple web design. And I learned how Google AdSense and stuff works, and eventually, I made online courses.

For me, it’s been a 20-year side hustling journey of not having a job, but having a series of little projects.

Each one of my side hustles added up to be what I needed to live off of. I had a project to go to every country in the world and I was able to fund that through side hustling. I was an aid worker for four years in Africa and paid my way for that through freelancing at night.

So I’ve just kind of learned by doing.

What’s a story of something that’s come about from the tour so far?

Chris: Great question. My whole focus is trying to help people not just be inspired, but actually do something. That’s really important to me. So I have this whole tagline on the side hustle school that reads, “Inspiration is good, but action is better.”

For me, it’s been really great. The book has been out for just a few weeks, but I’m already getting emails from people who are actually launching new courses, and have gone on to start their project.

There was somebody at the New York event, just a week ago, who came to the event and she actually signed her first client that night at the event before we left. That was great! She hadn’t even fully developed her project. She had this idea, and she was halfway along, but she had a confidence issue. So we talked it out in front of the whole audience.

And then later, I got an email that said she was in the book signing line and met somebody who is now her client. That for me is really, really exciting. I want to hear more stories like that.

If you could choose one lesson across your entire book catalog, what would it be?

Chris: I like what we talked about in terms of going from idea to offer.

I think that’s really important, and I spend quite a lot of time looking at that, and helping people see how you actually create offers. I tell them that the offer includes three different components. It includes a promise, a pitch, and a price.

A promise is a benefit. How is this going to change your life? How’s it really going to make your life better? I always encourage people to think in terms of those emotional needs.


If I signed up for a course on Skillshare, I’m going to learn about, I don’t know, android basket weaving or something. But what’s that really going to do for me?

Well, hopefully, I’m actually going to feel better about myself. I’m going to feel better about myself, I’m going to have more confidence and security, I’m going to be able to use that skill in a way that’s going to advance my life.

So if you start thinking in terms of a promise of benefit, your marketing just becomes much more powerful.

The second part is the pitch. You’ve got the promise, and the pitch is whatever you can do to tell a great story. I’m always encouraging people to think about why they started their project. Was it just to make money? Or was there something else to it?

There’s nothing wrong with just making money, but most people have some deeper kind of need that they’re trying to meet with their goal. So what is that? Of all the different things you could’ve done, why did you choose this one? This is your story, so don’t be afraid to share it. I think that’s important.

And then, the price, of course. Before you go too far into the process, really be thinking about what you’re going to charge and how you’re going to reach people who are willing to pay for it.

Why do you think the idea of a ‘side hustle’ has become so prominent now? Is it a relatively new trend, or has it always been this relevant?

“My parents were like, “What are you doing in the basement on the computer all the time?””

Chris: People have always been doing things like this, maybe in different ways.

I think it’s more relevant now because of two things; one is negative and one is positive. The negative is that people are feeling a lot of uncertainty and anxiety.

Even though some of the economic numbers are good, people still don’t trust the system. They don’t believe that they can go work for a company and that their employer will provide everything they need forever.

There is this sense that I have to create something for myself, even if I love my job, because nobody’s going to  care about my well-being as much as I do. Even if you work for a good company, you have no idea what’s going to happen. That company could change, or whatever.

As for the positive, I think there’s just never been so many opportunities, and it has never been so simple.

It is somewhat easy to get started with many of these things. Technology is mainstream now. eCommerce is mainstream. My grandma has a PayPal account… she’s in a nursing home, but apparently still shopping online!  When I started doing this 20 years ago, people thought it was weird. My parents were like, “What are you doing in the basement on the computer all the time?”

Now, you walk into Starbucks or any other place, and a dozen people are starting their little consulting business or sending out invoices and stuff as they sip their coffee. It’s much more accepted now, and that’s great.

Chris continues to lead a life of passion, encouraging others to work towards turning an idea into an asset, not just a part-time job. His new book, Side Hustle: From Idea to Income in 27 Days, is now available everywhere!

Written by:

Dennis Williams