Building a Business in Your Boxers
Everything I learned about making money on the internet without a commute, a boss, or real pants. From first client to consistent revenue in Mexico.
Client pipelines, revenue math, and the honest truth about working for yourself. These dispatches cover everything from finding your first client to building a sustainable business — without an office, a commute, or a performance review.
All DispatchesThe first real money I made on my own was forty-seven dollars. A consulting template I built on a Sunday afternoon, sold through a payment link I shared in two forums and forgot about. Three days later, someone in Minneapolis bought it. I have never been more proud of forty-seven dollars in my life.
This page is the honest guide to building income that doesn't require a commute, a boss, or the specific kind of death that comes from sitting in a conference room while someone reads bullet points off a slide you can already see.
Let me be direct: "passive income" is a phrase invented by people selling courses about passive income. Working for yourself is work. It's often more work than a regular job, at least at first. The difference isn't the effort — it's the ownership.
When I invoiced my first client two hundred dollars for a forty-five-minute strategy call, the amount didn't matter. What mattered is that nobody scheduled it for me, nobody took a percentage, and nobody sent a follow-up Slack message asking me to "document the takeaways in Confluence." I saw a need, offered a solution, got paid, and moved on.
That's a fundamentally different relationship with work. It's not easier. It's yours.
After two years of building income on my own, from a rooftop in San Miguel de Allende, I've found three models that produce real, recurring money without requiring venture capital, a large team, or pants:
If you spent years building expertise in a corporate role, congratulations — you have a skill set that companies will pay hourly rates for. The same strategic planning I used to do for a salary, I now do for clients at rates that would've made my HR department uncomfortable.
The key insight: companies don't hire consultants because they lack smart people. They hire consultants because they need an outsider who can say the uncomfortable thing without worrying about the next performance review.
Getting started:
Templates, frameworks, guides, tools — anything you can build once and sell repeatedly. My forty-seven-dollar template was the first. It's not a fortune, but it scales without requiring more of my time.
The math is simple: if 200 people buy a $47 product, that's $9,400. Build four products, and you have a small business that runs while you're at the market buying avocados.
What works:
This site is itself a revenue experiment. Not through ads — there are no ads and never will be. Not through affiliate links — same policy. The revenue comes from building an audience that trusts you enough to buy your products and services when you offer them.
The newsletter, The Dispatch, is the core of this. Every week, it reaches people who opted in because they wanted honest information about the topics I write about. Some percentage of those readers will eventually want a deeper engagement — a consulting call, a template, a guide. The content is the top of the funnel, but it's also the product. Both things are true.
Practically speaking, running a business from San Miguel de Allende requires three things:
Tax-wise: if you're a U.S. citizen, you owe U.S. taxes regardless of where you live. The Foreign Earned Income Exclusion (FEIE) can shelter the first ~$120,000 of earned income from U.S. federal tax. Mexico taxes residents on worldwide income, but the temporary resident visa has nuances — consult a cross-border tax professional. I use one. It costs $800/year. It's the best money I spend.
The first month feels like freedom. The second month feels like unemployment. By the third month, if you haven't built some structure, you'll be watching Netflix at 2 PM and calling it "ideation."
The loneliness is real. Not the social kind — you can solve that with a coffee shop and a few expat friends. The professional kind. Nobody is going to review your work and tell you it's good. Nobody is going to set quarterly goals that give your week structure. Nobody is going to promote you. The feedback loop that corporate provides — even when it's annoying — disappears completely.
You'll need to build your own. Mine looks like this: ship something every week, review revenue monthly, and keep a list of what I said no to. That last one matters. When you work for yourself, the biggest risk isn't saying yes to the wrong thing — it's saying yes to everything and ending up with a worse version of the job you left.
If you can't walk away from income entirely — or don't want to — this pillar is for you. You don't need to be a tech person. You need a skill that other people will pay for, a tolerance for uncertainty, and the willingness to invoice someone without apologizing for the amount.
The dispatches below are the real version. First clients, first failures, revenue math, and the specific kind of satisfaction that comes from making money that nobody approved, scheduled, or measured against a KPI.
Everything I learned about making money on the internet without a commute, a boss, or real pants. From first client to consistent revenue in Mexico.
Everyone tells you to 'start freelancing.' Nobody tells you where the first five clients come from or why the sixth one almost made you quit.