Book Review: Side Hustle

Chris Guillebeau, author of Side Hustle, is a really interesting guy. He’s never had a traditional job. What has he done instead? Well, for one thing he’s traveled to all 193 countries in the world. He’s made a living with various projects which now include books and a podcast. Essentially he’s been a lifelong side hustler.

His book Side Hustle comes with a lofty promise in the title: From idea to income in 27 days. Can you start successfully making money on the side in less than a month? Let’s dive in

Big Ideas I Love From Side Hustle

Here are some of my favorite insights and observations from the book.

Income = Options = Freedom

Why should you start a side hustle in the first place? The biggest reason is because extra income gives you extra options. And having more options means that you have more freedom.

The more money you can make on the side, the less dependent you are on your employer.

It’s possible that you want your side hustle to eventually replace your 9-5 income. Or maybe you love your day job and just want the joy of starting something yourself. Whatever the case, having the ability to make money on your own means that you aren’t completely devastated if you lose your job or your company folds.

The Willingness to Act

What’s the most important quality that makes for a good side hustler? The willingness to act.

This one is hard, but it’s important. If you’re too afraid to take the next step until you’re sure it’s going to be perfect, you’ll never get anywhere. The only way forward is to start before you’re ready and to iterate, improve, and improvise as you go.

Think of it like a big experiment. This isn’t your first product, it’s an experiment. This isn’t your first sales pitch, it’s an experiment. You’re just getting feedback. The only feedback that matters: Direct feedback from the marketplace.

This mindset is critical for the ability to successfully execute a side hustle. If you aren’t willing to start before you’re ready, you’ll never start, because you’ll never be ready.

Embrace Your Limitations

You have plenty of excuses. I get it. You don’t have money. You don’t have time.


You heard me: Good.

As Chris points out, if you had money, you’d spend it. If you had time, you’d waste it. Your limitations force you to do the best you can with what you have.

Speaking from my own experience, I didn’t find time to write this blog, I made time. Instead of getting up at 8am to get ready for work, I get up at 6 to write the blog.

In self help circles, it’s very much in vogue to make fun of the “get up early” approach. But the approach works. So you can either look cool in front of the self-help crowd by deriding my approach or you can actually do something.

Testing Ideas

In order to test ideas, remember that the goal is to “start a project that makes money in a short period of time.”

  • If you can’t envision the next steps, reject the idea
  • If you don’t see a way to get paid, reject the idea
  • If you’ll need three years to get up and running, reject the idea.

You should be able to explain your idea in one or two sentences. These sentences should cover what you will do, what the benefit will be to the customer, and how you’ll get paid.

Crafting an Offer

To make money, you need to make sales. To make sales, you need an offer.

According to Chris, you need to have three elements to have a good offer:

  • The Promise
  • The Pitch
  • The Price

The promise is where you tell the customer how you will change or impact their life (Chris’s promise in the subtitle of the books is that you’ll start making profit in 27 days).

The pitch tells them why they should buy. Or even better, why they should buy now.

The price obviously says how much it costs, but it also tells them how to buy. It’s a call to action (e.g. “sign up now by clicking this button”).

Chris says that “guitar lessons” is not an offer, but “Learn guitar basics quickly (and have fun doing it) from a veteran instructor with twenty years of performance experience. To sign up for hour- long lessons at $ 50 a lesson, call 555- Hot- Tunes now.” is.

Tell Your Story

Humans love a good underdog story. Fortunately for all aspiring side hustlers, you are a huge underdog. Let people know about it.

What inspired you to get into business? How humble were your means? How humble are your means? Don’t hide this information put it out there. It becomes part of the offer. People aren’t just buying your product or service, they’re supporting someone who is working hard to make their dream a reality.

You’re a person, not a corporation. Let everyone know who you are.

Obstacles vs. Details

Lot’s of people fail to get started because they are scared of “obstacles” like taxes and business licenses.

According to Chris, these aren’t obstacles, they’re details. Figure them out when you get there. Do a Google search. Schedule a 30 minute session with an accountant.

Everything will be okay. You’ve handles plenty of stuff like this before. It’s not fun, but it’s doable. And it’s certainly not worth worrying about ahead of time,

Here’s my favorite quote along these lines:

After I wrote The $ 100 Startup, I went out on the road and did an extensive book tour. Along the way I was a guest on many different radio and TV shows, where people were invited to call in and ask questions about the nuts and bolts of bootstrapping a business. To my surprise, a great number of the questions from listeners and viewers related to taxes, business licenses, and minor administrative functions. Why was I surprised? Well, because in many cases, these questions were from people who had no idea what their business was actually going to do or how it would make money. Asking, “Is this a feasible and profitable idea?” is a much more important question than “Which bookkeeping software should I use?” Logistical questions like these are all “figureoutable,” but without a plan for generating income, you don’t have a hustle.

Side Hustle (Kindle Edition) pg. 101

Pricing a Product

Pricing isn’t a perfect science and you’ll need to do some experimenting. But you can start with cost-plus pricing. Basically, just figure out how much it costs to sell one unit and then add the amount of profit that you’d like to make on each one.

Pricing a Service

Figure out how much time goes into providing the service (both billable and non-billable hours) and set an hourly rate.

This rate should be above what you make at your job (after all, you are giving up your free time to provide it).

“When in doubt…start!”

We’ve already hit on this idea, but it’s so important that we’re coming back to it.

Don’t know what price to charge? Pick one and change it later if you need to. Aren’t sure what makes a good sales pitch? Make one and learn from your mistakes later.

As they say: “Done is better than perfect.”

Launch in Beta

I’ll just let Chris share this one:

LAUNCH IN BETA What if you aren’t ready to launch? Well, you’re hardly ever fully ready… so here’s a trick. Go ahead and publish your offer, but add the label “beta” to it. You could also call it “early version” or any other phrase that sounds good. Doing so will allow you to continue working on it while also getting real feedback, and hopefully some sales as well. You can remain in this “already launched but not quite ready” phase for as long as you’d like. Gmail was in beta for over five years while it had more than 300 million users. This became a bit of a joke in tech circles— how can a service with 300 million customers claim to be in development?— but the point is that there is no rule that says your beta phase, preview mode, or “coming soon” status has to end at a certain point. If it helps you feel better to clarify that everything isn’t perfect yet, do so.

Side Hustle (Kindle Edition) pg. 153

Lead With Benefits

Features are about what a product or service does. Benefits are about what a product or service does for the customer.

What problem does it solve? How does it make them feel?

Ultimately, customers only care about features if they support benefits. Lead with the benefits, then support them with the features.

Final Thoughts

Chris really went all-in on this side hustle stuff. Not only has he lived it out and written a book about it, he also has a daily podcast called Side Hustle School where he breaks down stories of successful hustlers. If you’re into podcasts, be sure to check it out.

If you want to read the book, you can get it on Amazon or try the audiobook on Audible.

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