The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future

By Chris Guillebeau


Chris Guillebeau has visited every country in the world without ever holding a full-time job. That’s an amazing fact, but what’s even more impressive is that he isn’t the focus of The $100 Startup. Guillebeau received stories from over 1,500 people who successfully run their own businesses. The case studies in the book are presented as a sort of instruction manual for would-be entrepreneurs. Clear, concise, and full of actionable advice; everything I hope for when I open a new book.

I never planned to be an entrepreneur; I just didn’t want to work for someone else.

There’s no rehab program for being addicted to freedom. Once you’ve seen what it’s like on the other side, good luck trying to follow someone else’s rules ever again.

Perhaps most important, the vital career question of what is risky and what is safe has changed permanently. The old choice was to work at a job or take a big risk going out on your own. The new reality is that working at a job may be the far riskier choice. Instead, take the safe road and go out on your own.

Make no mistake: The blueprint does not tell you how to do less work; it tells you how to do better work.

Microbusinesses—businesses typically run by only one person—have been around since the beginning of commerce.

It’s not an elitist club; it’s a middle-class, leaderless movement.

In sharing how different people have set themselves free from corporate misery, the challenge is to acknowledge their courage without exaggerating their skills. Most of them aren’t geniuses or natural-born entrepreneurs; they are ordinary people who made a few key decisions that changed their lives.

To succeed in a business project, especially one you’re excited about, it helps to think carefully about all the skills you have that could be helpful to others and particularly about the combination of those skills.

Passion or skill + usefulness = success

There’s no failproof method; in fact, failure is often the best teacher.

To start a business, you need three things: a product or service, a group of people willing to pay for it, and a way to get paid. Everything else is completely optional.

The hard way to start a business is to fumble along, uncertain whether your big idea will resonate with customers. The easy way is to find out what people want and then find a way to give it to them.

Many business owners talk about their work in terms of the features it offers, but it’s much more powerful to talk about the benefits customers receive. A feature is descriptive; a benefit is emotional.

In deciding what to sell, the best approach is to sell what people buy—in other words, think more about what people really want than about what you think they need.

“If passion drives you, let reason hold the reins.”

Only when passion merges with a skill that other people value can you truly follow your passion to the bank.

When considering an opportunity, ask: “Where is the business model?”

Since the work part is what sustains everything else, it’s better to focus on it from the beginning. After all, the best thing about a location-independent business is possibility.

Even entrepreneurs like Brandon Pearce who have carefully built a high-income, hands-free business that allows them to work minimal hours do that only after the business has been established.

This is another sign of a good business opportunity: when lots of people are interested in something but have a hard time implementing it in their daily lives.

As you focus on getting to know “your people,” keep this important principle in mind: Most of us like to buy, but we don’t like to be sold.

When you’re brainstorming different ideas and aren’t sure which one is best, one of the most effective ways to figure it out is simply to ask your prospects, your current customers (if you have them), or anyone you think might be a good fit for your idea.

Sometimes, deciding not to pursue a promising project or deliberately turning away business is one of the most powerful things you can do.

Yes, you want to focus on meeting people’s needs and going above and beyond them whenever you can, but any single customer does not always know what’s best for your whole business.

Creating a “possibilities list” helps you retain ideas for when you have more time to implement them.

Putting something off doesn’t mean you’ll never do it, but prioritization will help you get started on what makes the most impact.

In the battle between planning and action, action wins.

A marketable idea doesn’t have to be a big, groundbreaking idea; it just has to provide a solution to a problem or be useful enough that other people are willing to pay for it.

If you were looking for your own product online but didn’t know it existed, what keywords would you search for?

It’s easier to sell to someone who knows they have a problem and are convinced they need a solution than it is to persuade someone that they have a problem that needs solving.

Having something that removes pain may be more effective than realizing a desire.

KEEP COSTS LOW. By investing sweat equity instead of money in your project, you’ll avoid going into debt and minimize the impact of failure if it doesn’t work out.

The first time you make a sale in a new business, no matter the amount, it’s a very big deal.

Competition from other businesses is a problem for another day; the greater problem you face is inertia.

Just as what we want and what we say we want aren’t always the same thing, the way we place a value on something isn’t always rational.

As you craft the offer, think about the objections … and then flip them around in your favor.

Generally, you should offer an incredible guarantee or no guarantee at all. A weak guarantee, or one that is unclear, can work against your credibility instead of helping it.

The difference between a good offer and a great offer is urgency (also known as timeliness): Why should people act now? Offer reassurance and acknowledgment immediately after someone buys something or hires you. Then find a small but meaningful way to go above and beyond their expectations.

A good marketer doesn’t rest on her laurels after a launch, because she knows she can probably increase the results significantly with little effort.

If you admit to a flaw, weakness, or limitation in your product, this will probably help instead of harm you.

If you’re getting positive feedback from people who don’t buy your product but want to support you in other ways, you’re on the right track.

It’s much easier to sell to an existing customer than to a new one, so work hard to overdeliver and plan ahead for the next project.

Getting the message out about your business is like writing a book: Before you do anything else, think about what you have to say.

The more you focus your business on providing a valuable service and helping people, the more your business will grow.

Another way to practice strategic giving is to deliberately not take advantage of every opportunity to increase income.

What if you deliberately said yes to every request unless you had a good reason not to?

The most powerful channel for getting the word out usually starts with people you already know.

Many aspiring business owners make two common, related mistakes: thinking too much about where to get money to start their project and thinking too little about where the business income will come from.

Spend only on things that have a direct relationship to sales.

Almost none of the people I met with talked about thriving in their new businesses because they always offered the lowest price.

Notice the important distinction that naturally happens when you offer a choice: Instead of asking them whether they’d like to buy your widget, you’re asking which widget they would like to buy.

Why is getting paid over and over such a big deal? First, because it can bring in a lot of money, and second, because it’s reliable income that isn’t dependent on external factors.

To gain more of each customer’s budget, you first have to zealously treat every customer as a “best” customer, no matter which ones actually end up becoming the proverbial “customer for life.”

Experimenting with price is one of the easiest ways to create higher profits (and sustainability) in a business.

It may be more important to pay close attention to where customers come from than to what you can do to convert them once they arrive.

Your customers want to hear from you. They have given you money in exchange for something they value. Make it easy for them to do so again and again.

Shine a spotlight on your best customers; let them tell their own stories about how they’ve been helped through your business. It helps to provide a variety of stories, as people will relate to different perspectives and backgrounds. This provides “social proof” that your product or service works for all kinds of people.


If you have a product business, ask yourself this question: “My product is x … how can I teach customers about y?”

To get an unfair advantage, provide remarkable service.

You can grow a business one of two ways: horizontally, by going wide and creating different products to apply to different people, or vertically, by going deep and creating more levels of engagement with customers.

Many of the problems people experience with outsourcing (on both sides) can be avoided by having a clear understanding of the responsibilities that a contractor or assistant will have.

If you have a range of projects, products, or activities, it’s almost always better to devote your efforts to the strong performers than to try and pull up the weak ones. Most people do the opposite, but if your goal is for everything to be average, that’s the best you’ll ever get.

Entrepreneurs are not necessarily risk takers; it’s just that they define risk and security differently from the way other people do.

“All the bad days have two things in common: You know the right thing to do, but you let somebody talk you out of doing it.”

Unfortunately, although hiring people can sometimes help a business grow, it always creates much higher costs and fixed obligations.

When you’re operating the business, you spend time putting out fires and keeping everything running as it should. Working on the business requires a higher-level approach.

CUSTOMER COMMUNICATION. This involves not just dealing with emails or general inquiries, but initiating communication through newsletters and updates. A key rule for all these activities is to initiate, not respond.

The most important step in creating an independent identity for the business is to create a product or service with the potential to scale.

You don’t need anyone to give you permission to pursue a dream.

Holly Minch mentioned the Goldilocks principle: the idea that success is found within certain margins and not at the extremes.

“I used to be afraid to fail. I wanted concrete numbers telling me that we weren’t going to lose before I took the leap. But if nobody was going to die, even in the absolute worst-case scenario, then what the hell was I so afraid of? I’ve never looked back.”

“The greatest benefit has been going to bed just as excited as if not more excited than when I woke up. I get to work day in, day out on something that fully engages me and elicits not just my passions but the passion of tons of other people, too.”


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