Nomad Capitalist Chapter 2: How to Go Where You Are Treated Best Without Becoming a Goat Herder

“Do I have to become a goat herder?”

That is how Henderson opens this chapter. His old college buddy Bryan asks this question while driving him from the Cape Town airport. Bryan has been watching Henderson post Facebook updates from El Salvador, Albania, Singapore. And he wants in. But he also has three kids, a wife, and an IT business with sixteen employees in South Africa.

Fair question, right? When someone tells you about this nomad lifestyle, the first thing your brain does is picture some guy milking goats on a mountain. Or living in a hut somewhere. That is not what this is about.

The Three Mistakes Almost Everyone Makes

Henderson breaks down Bryan’s situation into three problems. And honestly, these are the same three mistakes I see smart people make all the time.

Mistake one: working backwards. Bryan was trying to calculate the exact income he needed before he could “be free.” He figured $50,000 a year and he would be good. But he forgot about taxes. If he left South Africa, he could potentially pay zero income tax. That is an extra $10,000 right there. He was so busy building spreadsheets that he missed the obvious math.

Mistake two: ignoring what you can do right now. Bryan did not need to leave South Africa to start. He could set up a foreign company, open foreign bank accounts, keep his money in dollars instead of the unstable South African rand. All of this from his desk in Cape Town.

Mistake three: believing you are stuck. Bryan had sixteen employees. He thought he could never leave them. Henderson asked a simple question: what is the point of having sixteen employees if not one of them can manage things while you are away? Bryan was like a horse tied to a cheap plastic chair. He could run anytime. He just did not know it.

I have seen this pattern a lot in IT. People think they cannot go remote because “the team needs me.” Then the pandemic happened and suddenly everyone worked from home for two years. Turns out the team was fine.

The Ancient Greek Trick That Actually Works

Here is where Henderson brings in Stoic philosophy. I did not expect that from a book about offshore banking, but it works.

The idea is simple. It comes from Zeno of Citium, third century BC. The Stoics said you should imagine the worst-case scenario before doing anything. They called it negative visualization. What is the absolute worst that could happen?

Let us say you move some money from your bank in New York to a bank in Singapore. Worst case? The Singapore bank fails and you lose that money. That would be terrible. But you did not put all your money there, so you survive.

Now flip it around. What if you keep all your money in New York? Worst case? Another 2008 happens. Hundreds of US banks went under in that recession. Zero banks in Singapore did. So the risk of doing nothing is actually higher than the risk of diversifying.

This is the part of the chapter that hit me the hardest. We always think the safe option is doing what we already do. But Henderson makes a good argument that keeping everything in one country, one bank, one currency is actually the riskier move.

A Swiss bank account is just a bank account in Switzerland. Millions of Swiss people use them every day. Nobody panics about it. But somehow when an American opens one, people think something shady is going on.

Run Toward Something, Not Away From Something

Henderson makes an important distinction here. This is not about being angry at your government. It is not about hiding money or doing anything illegal.

He says there is a whole industry of shady guys with pen names selling “anonymous Vanuatu companies with bearer shares.” That is not what this is about.

Going where you are treated best means finding countries that genuinely want your business and treat it well. It means running toward better options, not running away from bad ones. The money you already paid in taxes is gone. No point in being angry about it. Focus on what you can change going forward.

I appreciate this because a lot of content in this space is just people complaining about taxes. Henderson says stop complaining and go fix it.

The Forty-Year Plan

This is my favorite part of the chapter. Henderson tells the story of a client named Mark. Multi-million-dollar business, late thirties, two kids. Mark was not looking for quick wins. He was looking at emerging markets the way Warren Buffett looks at undervalued stocks.

Mark was getting citizenship in a former Soviet country that nobody has heard of. His logic? “Imagine this place becomes the next Singapore.”

And Henderson backs this up with history. Singapore fifty years ago was a tiny breakaway city-state with no natural resources. Race riots in Kuala Lumpur pushed them to independence. Most people would have written them off. Today it is one of the richest countries on Earth.

Ireland was similar. Henderson’s taxi driver in Dublin grew up walking to school barefoot. His grandchildren now have jobs at Facebook and Google. If someone had gotten Irish citizenship forty years ago for cheap, their family would be sitting on one of the most valuable passports in the world today.

The window closes though. Singapore stopped easy immigration in 2013. Ireland closed its entrepreneur residency program to everyone except the next Instagram. You cannot get in after the party starts.

This hit home for me. Growing up in the former Soviet Union, I watched countries transform in one generation. Some went from nothing to thriving economies. Others went backwards. The difference was usually policy, not geography. Countries that made themselves attractive to business and talent grew. Those that did not, stagnated.

Diversification Is the Real Strategy

Henderson uses the story of a business partner who had everything in the United States. Banks, aircraft leasing, the works. Then 2008 happened. All gone. Fifty years of building, wiped out because everything was in one basket.

If that partner had diversified internationally, the damage would have been smaller. Asian companies were buying more planes than ever during that period. But he did not look outside his own country.

Then there is Cyprus. In 2013, the European Union decided to “bail in” Cypriot banks by taking depositor money above 100,000 euros. Just took it. If you had all your money there, you lost everything above that limit. If you had 10% of your money there, it hurt but you survived.

Henderson’s point is simple. Do not put all your eggs in one basket. And “one basket” does not just mean one stock or one industry. It means one country.

The Opportunity Is Now

Henderson ends the chapter by talking about how accessible all of this has become. Second passports used to be only for the yacht and private jet crowd. Now regular people can get them. Offshore banking used to require a Swiss banker driving to your house in a Mercedes. Now you can open an account with $100.

He talks about “Digital Nomad 2.0” which is businesses that are not just location independent but government independent. They do not rely on any single country’s rules or tax policies.

Estonia went from boiling stones for dinner under Soviet rule to inventing Skype in one generation. That kind of transformation is happening all over the world right now. Henderson says the smart move is to diversify across countries the same way you would diversify an investment portfolio.

Key Takeaway

The chapter boils down to this: you are probably not as stuck as you think. The fears holding you back are mostly in your head. Use Stoic negative visualization to honestly compare the risk of doing something new versus the risk of doing nothing. Then start small. You do not have to move to Panama tomorrow. But you can open a foreign bank account this month.

And think long term. The forty-year plan is not about tying up your money for forty years. It is about taking small bets on the future of different countries. Some will pay off big. Some will not. But having options is always better than having none.

Henderson’s friend Bryan did not need to become a goat herder. He just needed to stop building spreadsheets and start taking action.

Book: Nomad Capitalist by Andrew Henderson | ISBN: 9798461831486

Previous: Chapter 1 - Five Magic Words Next: Chapter 3 - The Location Independent Lifestyle

Part of the Nomad Capitalist series