The $100 Startup

"It's not an elitist club; it's a middle-class leaderless movement."

- The $100 Startup, page 8

How are people like Gary Leff, travel hacker and consultant, earning a yearly five-figure sum part-time, just by helping clients land cheap dream itineraries? Or what about Brett Kelly, author of the Evernote Essentials guide, who had earned a six-figure sum from his eBook, only to later land an official role at the actual Evernote company?

While reading into Chris Guillebeau’s new book, The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future, I realized that lots of these unconventional successes weren’t just lucky exceptions: they were just ordinary people who wanted a happier lifestyle while still providing value to others.

If you’re familiar with Chris’s original book, The Art of Non-Conformity, then you already know the mindset behind freedom and career independence. The $100 Startup is an actionable manifesto on the solopreneur and microbusiness movement which ties everything together so that you can turn your passion or skills into something people would deeply want and pay for.

But this isn’t just based on one person’s experience: The business advice is based off of Chris’s multiyear study of other successful renegades worldwide. When starting out, many of them found themselves in desperate situations before finally taking creative actions to design their livelihoods. It took some business savvy to execute their ideas, but the traditional way of starting a business didn’t apply: it didn’t require an MBA, extraneous schooling, venture capital, or even a detailed plan.

Let’s explore the relevant Insights which make up the crux of the $100 startup model.

The Big Idea

The Big Idea: The biggest takeaway from the book

The Core Formula

"Only when passion merges with a skill that other people value can you truly follow your passion to the bank."
- The $100 Startup, page 51

Passion is part of the microbusiness formula. But the formula itself is really no secret. Basically: Follow your passion, but follow it with good business sense. Turn your passion, or your skills, into a business model. Chris also states it point blank that if you’ve got people interested in what you do, but nothing to sell, then it’s not a business.

It’s worth noting that not every passion or skillset may be desirable by itself. This is where Chris reminds us about convergence, where your passion, or skill set, intersects with what other people will find useful. If you can find ways to “package” your passion or repertoire into a product or service that an audience would find useful (i.e. solves their problem), then your opportunities become evident.

Passion or Skill + Usefulness = Success



It doesn’t get any simpler than that.

If you’re starting out, ask yourself what you’re good at. What combination of skills can be converged with your audience? When you’ve defined that, you can continue figuring out the right audience and the right business model.

Insight #1

An actionable way to implement the Big Idea into your life

The Truth Behind Great Ideas

"What do people really, really want? At the end of the day, they want to be happy, and businesses that help their customers be happy are well-positioned to succeed."
- The $100 Startup, page 39

Inspiration from great ideas can come from anywhere. They may involve a hidden problem like an inefficiency in the market, or an opportunity seized from an emerging technology.

One inspiring case study is Brett Kelly’s Evernote Essentials guide. Before it was released, there just wasn’t a single guide that clearly detailed how to use Evernote to its full potential. At least for the English market. Brett was already a power user, and knowing the feeling of not having an explicit guide, he simply fulfilled that need for everyone else. The rest is history.

Finding the right audience or target market entails something different, too.

To find convergence between what we’re passionate about with what’s actually useful to others, Guillebeau notes that we should aim for a deeper understanding of our audiences. But it won’t have anything to do with traditional categories like age, gender or income.

Instead, get back to what matters most: the people you will serve. Use the new demographics (or psychographics) to better understand who your target market may be. These traits include: interests, values, beliefs, skills, and even their passions.

This is important because you’ll also gain insight into what really matters to them. Finally, you’ll land a better chance at what a problem looks like to them — through their eyes and through their perspective. The more clarity you obtain here, the more you can design your product or service to be unique and useful, rather than another uninspiring “me-too”.

Some good kick off questions that could lead you to inspiring ideas: What do young artists feel when using someone else’s product? What do users feel the most when using a particular web app for the first time? What pains busy professionals the most when it comes to learning something new?  What do these people want more of, and less of?

Insight #2

An actionable way to implement the Big Idea into your life

A Bias Towards Action

"There's nothing wrong with planning. But you can spend a lifetime making a plan that never turns into action. In the battle between planning and action, action wins."
- The $100 Startup, page 95

Why is it that some people fail to get what they want, no matter how riled up one may be about freedom and independence? Guillebeau says that sometimes some people just want “the fun and sun” without the work in creating. Creating always entails doing.

There’s also the danger with over planning. Here’s a brilliant question that Chris presents: How do you know an idea is even marketable unless you bring it out there in the first place?

We live in a time when information can be accessed anywhere and instantly. Many business functions can be automated through the cloud. Microbusinesses can cost almost nothing to start, most times only costing a few hundred dollars. Ideas can be rapidly tested, launched, marketed, and scaled. If something goes awry, you can cut something out with minimal blowback.

But without action – actually creating something and testing your market idea – your dream is just wishful thinking. Your plan is just a theory.

What’s being proposed is to maintain a bias towards action. Chris also calls this “planning as you go.”

What entails planning as you go? It means to simply getting started now: Once you’ve figured out what convergence means for you, find out the minimum viable product that it would take to launch. That way you can quickly test your market idea and swiftly adapt. You’ll also keep startup costs low, save money, and even heartache if things don’t turn out as expected. In a sense, you’re also “learning as you go.”

Here are some other helpful tips that signify a bias towards action:

Limit your business mission to 140 characters: You should be able to state in one sentence who you help and what the core benefit is. The length helps you state your purpose with clarity, and helps you avoid corporate-speak.

Keep any starting business plan to one-page max: There’s a template on Again, it helps narrow the details to the bare essentials like who you will serve, how’ll you do it, and what the elements of success will look like for you.

Achieve that first sale: The initial feedback is also the most potent and gives you immediate clues on next actions.


As far as the rest of the strategies and tactics in this toolbox, there’s plenty more to read and absorb. There’s a healthy balance here between inspiration and actionable business advice. Follow up those dreams and theories with your actions.

Action eventually multiplies. Even setbacks can add to your momentum. This last piece of wisdom from Fredrich Engels couldn’t be more fitting: “An ounce of action is worth a ton of theory.”

Start right now, create momentum, and build that legacy.

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Bryann Alexandros

ABOUT Bryann Alexandros

I help nonprofits and changemaking organizations become adaptive problem-solvers in the 21st century. My approach includes design thinking, applied creativity, process design, and helping senior leaders apply it to strategy and large-scale social challenges...
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