From The $100 Startup · Part I, Chapter 4

The Rise of the Roaming Entrepreneur

"A desk is a dangerous place from which to view the world."
— John le Carré

A typical day at the office (Hong Kong edition)

Carry-on bag with running shoes and two changes of clothes, short connection from Portland to Vancouver, twelve-hour Cathay Pacific flight to Hong Kong. Two hours for a movie, six for sleep, four for email. Arrive in Asia, clear immigration (no bags to claim), settle into a concourse chair, open the laptop, connect to HKG-Free-WiFi. Whoosh — out go all the emails I wrote on the plane, and in come 150 more that came in overnight.

I check in with my designer Reese about a project. Answer customer support requests — a page is down, someone needs a login. Write a quick update to customers. Check the one metric I monitor daily: new email subscribers. If that's healthy, the rest usually is.

Tonight I have a 2:00 a.m. conference call — daytime in North America — so I head to the Conrad Hotel rather than my usual guesthouse. The host on the call says "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 to Vietnam and Laos. 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.

It sounds like a fantasy. It isn't — it's happening on a broad scale, with thousands of people around the world. My example is just one. Let me introduce a few others.

Case study 1: Brandon Pearce, $360K from Costa Rica

In 2009, Brandon Pearce was living in Utah and working as a piano teacher. Getting by. Paying the rent. Doing something he enjoyed. But he was also intensely curious and wanted to combine his interest in technology with his interest in music education. As he thought about the colleagues he knew, he found the convergence point.

"Music teachers don't want to deal with business administration," he told me. "They want to teach music. But in the typical music teacher's workday, they have to spend much of their time dealing with admin tasks." Scheduling, rescheduling, sending payment reminders — time-consuming, attention-eating, and a constant source of money leaking out the side because of missed sessions and forgotten invoices.

Brandon didn't set out to build a business. He built a tool to solve his own problem and called it Music Teacher's Helper. Other music teachers wanted in. He turned it into a one-stop platform — scheduling, billing, a no-tech-skills-required website builder, all of it. He didn't undercut his price: the product has a free tier and a top tier that runs $588 a year per teacher, with several options in between.

Three years later, his life looks different. He lives in Escazú, Costa Rica with his wife and three daughters. He has ten employees in different time zones. He tracks his time and spends 8–15 hours a week directly on the business. The rest goes to family and to side projects he runs for fun.

The family lives in Costa Rica now. But that's not the whole story. The whole story is they could live anywhere. A visa run to Guatemala — eight days. Unschooling the children means they can pick up and go. A tentative future plan involves moving to Asia.

One more number: Music Teacher's Helper is on track to clear at least $360,000 a year. Because customers pay monthly and stay for years, that number doesn't go down. It goes up.

Case study 2: Kyle Hepp, weddings from anywhere

Originally from Michigan, Kyle Hepp moved to Chile with her husband Seba. She worked side projects for AOL while looking for a job in sports management. Seba's construction job was shaky and the company started to fold. One Friday afternoon, his salary was cut 20%. He declined the new contract and was let go.

Two days later, Kyle was out jogging when a pickup truck hit her at a crowded intersection and sent her flying a hundred feet. She survived, but was hurt badly enough that she spent a week in the hospital and several more weeks unable to walk or type — which ended the AOL gig too. "Between my husband's layoff and getting run over by the car," she told me with a straight face, "it was kind of a bad weekend."

Since they were both unemployed anyway, they took the honeymoon they'd never had — a few weeks in Italy. Before flying out, Kyle updated her old wedding-photography website and announced she was open for bookings. A request came in right away.

Back in Chile, they decided to try photography full-time "at least until the bookings stopped coming and the money ran out." The bookings didn't stop. Within two years they were making $90,000 a year and were fully booked another year in advance, doing weddings in Argentina, Spain, England, and the United States.

Why do clients fly her in when there's no shortage of good local photographers? "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: Bernard Vukas, $720 in one day

Bernard Vukas is from Croatia. He helps companies that process large amounts of data through Microsoft Office — building or modifying extensions that make the work easier. He told me about his workspace in an email from a beach in Koh Tao, Thailand, where he was living indefinitely: "I work from anywhere, anytime. Time zone and location are irrelevant. All my property fits in a single backpack, including the laptop."

Bernard started with rates that were decent by Croatian standards but much lower than North American firms were used to paying. That established his client base. The best decision he made was tripling his rates for new clients.

One day, he made $720 on a single project. He wrote later: "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."

Croatia has nice beaches of its own. Bernard wanted to see more of the world. His work doesn't require him to be in any particular place, so he isn't.

A brief primer on location independence

Become your own publisher

Many roaming entrepreneurs are publishers — they sell what they know as digital products. Information publishing is one of the most common and most profitable models for a location-independent business, so let me spend a few hundred words on it.

Jack Cover runs 800-CEO-Read, a leading retailer of business books. I asked him what's changed about publishing in recent years. "Everything's changed," he said. The big change isn't the existence of self-publishing — it's the quality. "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."

You don't need to be an author, or even think of yourself as a writer, to take advantage of this. Digital publishing usually fits into three buckets: one-off products, fixed-period courses, and recurring subscriptions.

Jen Lemen and Andrea Scher had an idea for an online course for women, called Mondo Beyondo. Susannah Conway built a similar one called Unravelling. Both produce six-figure annual incomes. Both grow primarily by referral — students finish the four- or five-week courses and tell their friends, who sign up for the next session.

At larger scale, Brian Clark runs a company in Texas that earns more than five million dollars a year, employing a dozen people. A big chunk of the revenue comes from recurring subscriptions to website themes and marketing services. Many customers arrive through his writing on Copyblogger.com.

Is there enough market for all of this? Long answer: yes. I had to decline many information-publishing stories because this isn't a book strictly about it. The model is here to stay.

The $120,000 ebook

Brett Kelly is a self-described professional geek who worked as a software developer in Fullerton, California. Busy job, stressful home life. $15,000 of credit-card debt. Brett and his wife Joana worked opposite schedules to make rent. "I'd get home and trade off with a high-five to Joana as she went to work at a restaurant," he told me over tacos in LA. "The last few months, we were both tired all the time, the kids were unhappy, and the overall situation wasn't good."

Brett had watched friends and colleagues launch profitable side projects for years. Finally he had an idea of his own: he was a power user of Evernote, the free note-keeping software, and there was no comprehensive user manual. He spent months documenting every tip and trick with detailed screenshots and tutorials. The finished PDF, Evernote Essentials, came in at over 90 pages of solid content with no padding.

Before launch, Brett made a deal with Joana: if he sold $10,000 worth of copies, she would quit the restaurant job and stay home with the kids full-time. Brett estimated it would take months.

Eleven days after Evernote Essentials went on sale, the PayPal account tipped into five figures. Joana put in her two-weeks notice the next day.

Months later, sales continued at $300+ a day — an annualized $120,000 — for what was essentially a side project. If the same content had been a print book through a traditional publisher, the author royalties would have been roughly $18 a day. Brett owned it, delivery was digital, and almost the entire $300 was profit.

In an odd twist, Evernote's executives got wind of the guide and contacted him. He thought he was in trouble for selling something based on their free product. The opposite: the CEO loved it and hired him. Brett works at Evernote now, retains all profits from the guide, and works from home.

The 8-step publisher framework

Eight steps to enter the information-publishing business. Each can be made more complicated, but they all map onto this outline.

The reality check

Not every roaming-entrepreneur story is a Brett Kelly story. Many aspiring publishers operate on an "if you build it, they will come" model — and many of them learn the hard way that the better version is "if you build it, they might come." For every Mondo Beyondo, there are many courses that finish with five participants. For every $120,000 ebook, many sell two copies and fade.

Most failures trace back to focusing on the "anywhere" part more than the "work" part. The classic image of the roaming entrepreneur is someone on a beach with a laptop, drink nearby, sunset in the background. My limited attempts at this involve worrying about getting sand in the keyboard and straining to see the screen against the glare. Most beaches don't have WiFi. Plenty of other places don't either. If you're going to run a business on the road, the discipline has to come from you, not the location.

The honest version of Brandon Pearce's story is that the high-income, low-hours version only exists because he put in the time when nobody was watching. In the early years there was a fair amount of fumbling and a large number of hours spent on things that may or may not have worked. The freedom on the other side is real. So was the work to get there.

Key takeaways

• Roaming entrepreneurs are everywhere. Many are quietly building six-figure businesses while living in paradise. The category is real.
• Not every nomadic dream is well-aimed. A lot of people pursue the lifestyle for the wrong reasons. The better question: what do you want to do?
• Information publishing is a strong location-independent model. Ebooks, courses, subscriptions. Make it once, sell it many times.
• The fundamentals don't change. Convergence, skill transformation, and the magic formula from Chapter 1 still apply — no matter where you end up living.

Where this fits in the book

"The Rise of the Roaming Entrepreneur" sits at Chapter 4, in the second half of Part I. It introduces two threads — location independence and information publishing — that recur throughout the rest of the book. Brandon Pearce, Kyle Hepp, and Brett Kelly all appear again in later chapters; the publisher framework above is the spine of much of Part II.

The chapter sits between Chapter 3 (Follow Your Passion... Maybe) and Chapter 5 (The New Demographics), and closes the run of "who these people are" chapters before Part II shifts into "how to do what they did."

Frequently asked questions

What is a roaming entrepreneur?

Someone who runs a business that doesn't require them to be in any particular place. Their workspace fits in a backpack. The business is structured around their life, not the other way around.

How do you start a location-independent business?

Start it before you hit the road. Operating an existing business while roaming is much easier than starting one in motion. Pick a model that doesn't depend on physical location, keep your work in the cloud, establish reliable income, then go.

What is the information-publishing business model?

Selling what you know in digital form — ebooks, courses, fixed-period programs, recurring subscriptions, or a mix. Brett Kelly built a $120,000-a-year business from a single PDF about Evernote. The model scales because delivery is digital and you create the product once.

Can anyone become an information publisher?

Almost. You don't need to be an author. Eight steps: find a topic, capture the info, package it, make an offer, price fairly, set up payment, publish, refine. The hard part is shipping something imperfect rather than waiting for it to be perfect.

Where does this fit in The $100 Startup?

Chapter 4, in Part I (Unexpected Entrepreneurs). It introduces location-independent business and the information-publishing model — two threads that recur throughout Parts II and III.