The Rise of the Roaming Entrepreneur - UNEXPECTED ENTREPRENEURS - The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future - Chris Guillebeau

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future - Chris Guillebeau (2012)


Chapter 4. The Rise of the Roaming Entrepreneur


“A desk is a dangerous place
from which to view the world.”


Packing a carry-on bag with running shoes and two changes of clothes, I head out into the world via a short connection from Portland to Vancouver International Airport. Later that evening, the twelve-hour Cathay Pacific flight to Hong Kong gives me two hours to watch a movie, six hours to sleep, and four hours to write emails.

Arriving in Asia, I clear immigration (no bags to claim), check my wallet to see if I still have local currency from the last trip here, and settle into a concourse chair before jumping on the train into the city. I flip open the laptop, connect to “HKG-Free-WiFi,” and log onto the world. Whoosh … out go all the emails I wrote on the plane, and in come 150 more that arrived during the night.

I check in with Reese, my designer, about a project we’ve been working on. I answer customer support requests—a page on our site is down, someone needs a login, and so on—and write a quick update to customers. I review reader comments from my latest blog post and quickly check my daily list of email signups, the only metric I monitor on a frequent basis. (If all’s going well with new subscribers, everything else should be OK.)

I often stay in guest houses and hostels, but later tonight I have a conference call scheduled for the bleary hour of 2 a.m.—it’s daytime in North America—so I head to the Conrad Hotel. Fortunately, I slept enough on the plane that I’m good to go after a shower, so I set up shop in my “office” for the next two days. A few hours later, the host on the call is saying “good afternoon” to everyone, and I try to refrain from mentioning the local time while looking out at the Hong Kong skyline.

On this trip I’m headed on to Vietnam and Laos, but I could be going anywhere. After I adjust to the time difference over the next couple of days, I settle into a routine of morning work and afternoon exploration. At least one week a month, I live in this dream world of travel, work, and frequent coffee breaks. The business is structured around my life, not the other way around.

I know what some people think: It sounds like a fantasy. Well … it really is happening, on a broad scale, for thousands of people all over the world. My example is just one of many; let’s hear about a few others.

Case Study 1: The Music Teacher

In 2009, Brandon Pearce was living in Utah and working as a successful piano teacher, meaning that he got by and paid the rent while doing something he enjoyed. But Brandon was also intensely curious, and wanted to combine an interest in technology with his passion for music education. As he thought about colleagues he knew, he found the convergence point between his skill and what they needed.

“Music teachers don’t want to deal with business administration; they want to teach music,” he said. “But in the typical music teacher’s workday, they have to spend much of their time dealing with administrative tasks.” Scheduling, rescheduling, sending reminders—in addition to time, all these things take up a lot of attention and distract from teaching. Furthermore, many music teachers aren’t making all the money they should, since payments are sometimes overlooked and students fail to show up.

Brandon didn’t intend to create a business at first; he just wanted to solve what he called the “disorganized music teacher problem” for himself. The answer was Music Teacher’s Helper, an interface that Brandon created for personal use before turning it into a one-stop platform for music teachers of all kinds. The teachers could create their own websites (without having any technical skills) and handle all aspects of scheduling and billing, thus enabling them to focus on the actual teaching they enjoyed.

Was this a market in search of a solution? Yes, and the market was substantial. Was Brandon giving them the fish? Yes, and because music teachers are often on a low budget, Brandon made sure to highlight the fact that paying for Music Teacher’s Helper might actually save them money over time, but to ensure the business’s profitability, he didn’t skimp on the price. The service is available in several different versions, including a free version for limited use and going up to a $588-a-year version depending on the number of students.*

Three years later, Brandon’s life is quite different. Instead of living in Utah, he now wakes up in sunny Escazú, Costa Rica, where he lives with his wife and three young daughters. He has ten employees living in different places around the world. He carefully tracks his time and estimates that he spends eight to fifteen hours a week directly related to the business. The rest of his time is spent with his family and on various side projects that he pursues for fun.

Brandon and his family used to live in Utah and now they live in Costa Rica, but that’s not the whole story; the whole story is that they could live anywhere they want. When they needed to do a visa run, they went over to Guatemala for eight days, and since Brandon and his wife are “unschooling” their children and can easily take them anywhere, there’s no telling where they’ll end up next. (A tentative plan involves moving to Asia.)

Oh, and one more thing: Music Teacher’s Helper is currently on track to earn at least $360,000 a year. Because his customers commit for the long term and pay monthly, it’s unlikely that this number will ever go down. Instead, it will continue to increase as more and more music teachers join the ranks.

Case Study 2:
The Accidental Worldwide Photographer

Originally from Michigan, Kyle Hepp is an “accidental” entrepreneur in the literal sense. Having relocated to Chile with her husband, Seba, Kyle made ends meet by working on side projects for AOL while she looked for a job in her planned field of sports management. The South American lifestyle was great, but Seba’s job as a construction engineer was far from secure, and the company started to go under. One Friday afternoon, he received notice that his salary was being cut 20 percent. He declined to sign a new contract and was immediately let go.

Two days after learning of the layoff, Kyle was out jogging when tragedy struck in the form of a pickup truck that ran into her at a crowded intersection, sending her flying a hundred feet from the point of impact. Her injuries weren’t life-threatening or permanent, but as you’d expect, Kyle was badly hurt. After a week in the hospital, she spent several more weeks at home, unable to walk and with so many bruises that she couldn’t even type—thus ending the side gig with AOL, which was done on a contract basis. “Between my husband’s layoff and getting run over by the car,” Kyle told me with a straight face, “it was kind of a bad weekend.”

Kyle and Seba had been married for nearly three years at that point and hadn’t ever had a real honeymoon, so they decided they might as well take vacation time while they could. Instead of looking for work, they booked flights to Italy and spent several weeks seeing Europe for the first time. Before the accident, Kyle had been dabbling in wedding photography. She had never really tried to make a career of it, but before flying out she updated her website and announced that she was accepting new bookings. A request came in right away, giving Kyle confidence that she might be able to make some kind of career out of it.

When they returned to Chile, Kyle and Seba decided to try photography full-time, “at least until the bookings stopped coming and the money ran out.” To their surprise, request after request arrived in Kyle’s inbox, and the schedule quickly filled up. Two years later, they were making $90,000 a year and were fully booked another year in advance.

They now work all over the world, doing weddings in Argentina, Spain, England, and the United States. You might wonder what the big deal is with Kyle’s work—since there is no shortage of other good photographers available locally, why do clients fly her from country to country? Kyle says that her clients are usually well traveled themselves, and aren’t afraid of hiring someone from afar. “They know that the world is a small place,” she says, “and they like our work because we build relationships over time.”

Case Study 3: The Spreadsheet King

A description of Bernard Vukas’s work space is typical of roaming entrepreneurs: “I work from anywhere, anytime. Time zone and location are irrelevant. All my property fits in a single backpack, including the laptop,” he told me in an email from a beach in Koh Tao, Thailand, where he was living on an indefinite basis. Bernard is from Croatia, which has nice beaches of its own, but he wanted to see more of the world.

Bernard helps companies that use Microsoft Office applications to process large amounts of data, creating or modifying extensions that make the data easier to manage. Bernard started by pricing at a decent wage by Croatian standards but much lower than what North American companies were used to paying. This strategy worked well in helping him establish a client base and a good reputation, but the best business decision came when he tripled his rates for new clients.

One day, Bernard made $720 on a big project. Reflecting on the amount’s significance, he wrote: “Many people on a minimum salary in Croatia are getting this amount in one month. People who get double that amount are considered well paid. To have it all come in on a single day is unheard of.” Bernard might return to his country of origin at some point, but it was hard to imagine him ever returning to another way of life.

A Brief Primer for Location Independence

It’s usually easier to operate a business while roaming the world than it is to start one. Be sure to spend plenty of time getting set up before you hit the road.

With a U.S. or Canadian passport, you can stay for up to ninety days in many different countries around the world. In some of them, you can do a “visa run” across the border after the time is up and then return for another extended stay.

You can learn about the visas required for different countries by visiting or, a commercial service I use for my own visa applications. Other companies offer the same assistance, and you don’t need to use a service to apply for visas if you’re not traveling that frequently.

As much as possible, keep your work “in the cloud” by using online services such as Google Docs and Dropbox. This way, you can access it from anywhere and don’t have to worry as much about keeping your data with you.

Change your password frequently, and don’t use the name of your cat as the password (not that I learned this through experience or anything …).

Stay for free with helpful hosts through, or at low cost from individual landlords at

You can start from anywhere, but as a general recommendation, Latin America and Southeast Asia are two of the easiest and most hospitable regions to begin your nomadic adventures.

Some places are more tech-friendly than others. To be aware of what to expect before visiting a new country, study up by reading the forums at or

As you roam, maintain a balance between adventure and work. Remember that most people work regular jobs and travel only once in a while, so be sure to take advantage of sightseeing and experiencing the local culture. But similarly, don’t feel bad about needing to devote more hours to work whenever needed. It’s OK; the work allows you to travel.

Digital nomads and roaming entrepreneurs come in all packages, and it’s hard to get away from their infectious stories. As I interviewed business owners and put the word out for more submissions, I kept hearing story after story that sounded like those of Brandon, Kyle, and Bernard. I’d continue to cast the net for more traditional businesses, but I kept thinking: This is a great business model. Why would you want to do anything else?

In these examples, Brandon is a music teacher, Kyle is a photographer, and Bernard is a developer. The list could go on: Cherie Ve Ard, whom we’ll meet in Chapter 13, is a health-care consultant, and Brandy Agerbeck, whose story is in Chapter 7, is a graphic facilitator. Because of the nature of their work, many of the businesses in the other case studies are technically location independent even if they currently have a fixed address. There is more than one road to the road, in other words, but one business model is especially useful for location independence: the business of information publishing. Since this model is both common and highly profitable, let’s look at it in some detail.

Become Your Own Publisher

As the founder of 800-CEO-READ, a leading retailer of business books, Jack Covert is a veteran of both traditional publishing and self-publishing. I asked Jack what has changed about the publishing world in recent years. “Everything’s changed,” he said. “We’ve always seen authors self-publish their works, but never to such a wide extent. What’s different is the quality of the work. These days, a number of self-published works have at least as good a quality as do books from big publishers. The playing field has been greatly leveled, and continues to be.”

The other thing that’s different, Jack told me, is that most authors chose self-publishing in the past because they couldn’t get a traditional publisher to purchase their work. Today, some authors are deliberately choosing to distribute their work directly, even turning down significant offers in favor of going it alone.

But hey, who needs books? You don’t need to be an author or even think of yourself as a writer to take advantage of this changing world. Digital publishing tends to fit into at least a few categories: one-off products, fixed-period courses, and recurring subscriptions.

Jen Lemen and Andrea Scher, two friends who had attended a retreat together, had an idea to start an online course for women. They called it Mondo Beyondo, and created a community model for participants to post their life lists, goals, and ideas. On the other side of the Atlantic, former journalist Susannah Conway was independently setting up a similar project called Unravelling. Thousands of participants later, both projects have long waiting lists for future sessions, and both produce six-figure annual incomes. Part of the beauty of this model is that it grows predominantly by referral. As students finish the four- or five-week courses, many of them tell their friends, who then sign up for the next session.

A few people have created true scale in their online publishing efforts. In Melbourne, Australia, Darren Rowse created a popular photography forum that attracted more than 300,000 subscribers in less than three years. He also founded ProBlogger, a hub for new digital publishers seeking to learn the ropes. In Texas, Brian Clark runs a company that provides online services, including website themes and marketing advice. Many customers arrive from Brian’s writing on and related sites. The business employs a dozen people and earns more than $5 million a year, in large part thanks to reliance on recurring subscriptions. (We’ll discuss subscriptions and hear more from Brian in Chapter 10.)

A cynic might wonder, Is there really so much market space for all of these projects? Long story short, the answer is yes. These examples aren’t highly unusual, and I had to decline many additional stories because this book is not strictly about information publishing. Some parts of information publishing are still in a Wild West stage, but this strong business model is here to stay.

Like everything else under the sun, this “new” business isn’t entirely new. As Jack from 800-CEO-READ mentioned, some independent publishers have always known that it’s often better to sell direct. What’s changed is the speed, quality, and potential to reach a much broader audience. That’s what these roaming publishers are doing—and a guy in Fullerton, California, provides a typical example.

The $120,000 E-Book

Brett Kelly, a self-described “professional geek” who worked as a software developer, had a busy job and a stressful home life. As a result of $15,000 of credit card debt and the high cost of Southern California living, Brett and his wife, Joana, worked opposite schedules to make ends meet. “I’d get home and trade off with a high-five to Joana as she went to work at a restaurant,” he told me as we sat at a taco stand in Los Angeles. “The last few months, we were both tired all the time, the kids were unhappy, and the overall situation wasn’t good.”

For years, Brett had watched from the sidelines as friends and colleagues started profitable projects and either quit their jobs or established an additional income stream. Finally, he had an idea of his own: As a power user of Evernote, the free note-keeping software, Brett noticed that there was no detailed user manual for people to get the most out of the service.§

Brett spent months carefully documenting every tip and trick he could find about Evernote, compiling everything with detailed screenshots and tutorials into a big PDF file. “I obsessed over this thing,” he said, “and I wanted to make sure I got everything exactly right.” When he sent me a draft of what would become Evernote Essentials, I was impressed. Many e-book writers pad their products with superfluous copy, big fonts, and wide margins. Brett’s was the opposite: The finished product weighed in at more than ninety pages of solid content. Nevertheless, solid content isn’t everything; you also have to sell something that people are willing to spend money on. Would they?

Right before the guide went on sale, Brett made a deal with Joana: If he sold at least $10,000 worth of copies, she would quit her job waiting tables at the restaurant and stay at home with their two kids full-time. Brett estimated that it would take months, if not longer, to reach the $10k goal … but just eleven days after Evernote Essentials went on sale, the PayPal account tipped into five figures. (Being the geek that he was, Brett promptly took a screenshot on his iPhone and made it his wallpaper.) Less than twenty-four hours later, Joana put in her two-week notice at the restaurant. Aside from brief breaks when the kids were born, this would be the first time she didn’t work in their seven years of parenthood.

Months later, sales of Evernote Essentials continued to bring in at least $300 a day, projecting annual revenue of more than $120,000 for something that was essentially a side project. Interestingly, if the project had been produced as a print book from a traditional publisher, those numbers could be considered a failure—author royalties would have brought Brett only around $18 a day. But since Brett was the sole owner and delivery was digital, the $300 that arrived in his PayPal account every day was almost entirely profit.

In an odd twist, the executives who developed Evernote got word of the guide and sent Brett a note that they wanted to talk. Brett was worried they were upset about him making money from their free product, but the opposite was true: The CEO loved it and wanted to hire him. Brett left the boring full-time job and took on a new role at Evernote, with the understanding that he could continue to sell the guide and retain all profits while working at home for the company. Sweet! Here’s how Brett describes the end results:

The unreal success of this project has not only freed our family from a decade of debt and financial instability but has also given us the freedom to pursue the kind of life we want. Since I now work from home and Joana is a stay-at-home mom, we spend far more time with our kids than most people could hope for. There are times when I still can’t believe it’s actually happened, and I couldn’t be more thankful.

Brett’s project had all the predictors of success we’ve considered thus far: It began with something he was both passionate about and skilled in, and then he forged his knowledge into a useful package that could be acquired instantly by users. If you wanted to learn about Evernote but didn’t want to spend the time surfing around, a $25 investment could solve the problem. The choice of price was also perfect: Brett could have priced much lower, as some digital publishers do, but he chose to take a stand and provide a clear value proposition to his potential customers.

Become Your Own Publisher

Follow these steps to enter the information publishing business. Each step can be made more complicated, but they all relate to this basic outline.

1. Find a topic that people will pay to learn about. It helps if you are an expert in the topic, but if not, that’s what research is for.

2. Capture the information in one of three ways:

a. Write it down.

b. Record audio or video.

c. Produce some combination of a and b.

3. Combine your materials into a product: an e-book or digital package that can be downloaded by buyers.

4. Create an offer. What exactly are you selling, and why should people take action on it? Learn more about offers in Chapter 7.

5. Decide on a fair, value-based price for your offer. For pricing guidelines, see Chapters 10 and 11.

6. Find a way to get paid. is the most ubiquitous method, with the ability to accept payment from users in more than 180 countries. Other options are available if you want more flexibility.*

7. Publish the offer and get the word out. For an overview of hustling, see Chapter 9.

8. Cash in and head to the beach! (This step may require further effort.)

*You can find a review of several different payment options in the online resources at

Alas, like any trend or business model, not every story of independent publishing is a success. Many aspiring publishers operate on an “if you build it, they will come” model. Later in the book, we’ll rename it the “if you build it, they might come” model—sometimes it works, but many times it doesn’t, and there’s no guarantee of instant riches. For every online course that becomes a Mondo Beyondo-size success, many others flounder on with five participants. For every $120,000 e-book like Brett’s, many others sell two copies (one to the writer’s grandmother and one to a friend of the family) before fizzling out.

Some of the failures relate to unrealistic expectations. Put simply, some people want the sun and the fun (or the $300 a day) without the work. Partly as a result of the allure of working from anywhere, many aspiring entrepreneurs focus much more on the “anywhere” part than they do the “work” part. 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. The fact that you can head off to Argentina or Thailand on a whim doesn’t necessarily mean that you actually will.

The classic image of a roaming entrepreneur usually involves a guy or girl sitting on the beach in a swimsuit, drink nearby, with a laptop propped up against the backdrop of a sunset. My limited attempts at replicating such a scene usually involve worrying about the laptop (Will it get stolen? Will I get sand in the keyboard?) and straining to see the screen against the glare of the sun. Furthermore, most beaches in tropical locales do not provide WiFi access, and for that matter, plenty of other places don’t either—so if you’re going to operate your business on the road, you’ll need to learn to think about your business as much as you think about being on the road.

It’s just like following your passion to the bank: Some people prefer to keep their passion on the side, and some people prefer not to mix their vacations with their work. 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. In the beginning, there’s usually a fair amount of fumbling and a large number of hours spent working on projects that may or may not succeed.

But hey, that’s enough of a reality check. There’s no doubt that thousands of people have established successful businesses on this model, especially over the last decade. Why not follow in their path, charting your own course along the way?

When I last talked with Brandon, he was still doing extremely well (up to $30,000 a month in our most recent conversation). He was now branching out into new areas in Costa Rica and beyond, even thinking about buying shares in a local farm. Perhaps the farm won’t be as profitable as the online project, but that’s OK—month after month, the income from the music software will continue to roll in. Brandon and his family have established complete freedom and the ability to make a new life wherever it leads them. Every day is an adventure.


Roaming entrepreneurs are everywhere these days. Many of them are quietly building significant (six figures or higher) businesses while living in paradise.

Just as not every passion leads to a good business model, a lot of people pursue the nomadic lifestyle for the wrong reasons. The best question to answer is: What do you want to do?

There are many roads to location independence, but the business of information publishing is especially profitable. (And there’s more than one path to information publishing; it isn’t just about e-books.)

Everything relates to the lessons that began in Chapter 1: Find the convergence between what you love and what other people are willing to buy, remember that you’re probably good at more than one thing, and combine passion and usefulness to build a real business—no matter where you end up living.

*The specific pricing model that Brandon chose for his business is an important factor in its profitability. We’ll look at pricing and how it relates to overall income in Chapters 10 and 11.

Bernard, the “Spreadsheet King,” is a different guy from Purna, “Mr. Spreadsheet.” Lesson: At least in the world of spreadsheets, there’s always room for one more.

One frequently cited example is Barry Eisler, who turned down a $500,000 offer for one of his books. However, he has a sizable following and an established track record that new authors lack.

§Technically, there was no English-language manual; more than a dozen books or guides on Evernote already existed in Japan. This suggested the strong marketability of the project and revealed a gap in the English-language marketplace that Brett was able to fill.