They said I was a trust fund baby… here’s the truth

Anytime someone retires young, people love to say the same thing: “Must be nice. Trust fund baby.”

I get why that assumption exists. Early retirement can look like this magical, mysterious thing that only happens for people with rich parents, fancy degrees, or wild luck.

But the truth is usually a lot messier. In this case, it started with a four-year-old kid in a broken home, an ugly divorce, and a whole lot of hunger—literal and financial.

In this article, I want to walk you through that journey, not because the details of one person’s life are the blueprint, but because the principles underneath it absolutely are. You can use them whether you’re aiming for full early retirement or just more freedom and stability than you grew up with.

Growing up hungry (in more ways than one)

The story doesn’t begin with privilege. It starts with a messy divorce when he was four. His mom got custody despite being unstable and often absent. He and his brother saw their dad once a week for a couple of hours and every other weekend.

Dinner was not a given. Some nights, no one came home. No food, no structure, no supervision. He jokes that he was raised on “hose water and neglect,” but underneath the joke is a kid who learned two things very early:

1) No one is coming to rescue you financially.
2) If you want something different, you’re going to have to build it yourself.

The first side hustle: $5, pizza, and Pokemon

By age 10, he was already knocking on doors, mowing lawns, and pulling weeds in the summer heat. One day, while playing foursquare in a Domino’s parking lot, the manager came out with an offer: hand out flyers around the neighborhood and earn a $5 bill plus a medium pizza.

Child labor laws were looser, and for two kids on bikes with empty stomachs, that was a dream deal. But here’s where the story takes a personal-finance turn: he didn’t just see $5 as spending money. Even at 10, he was asking, “How do I make this money grow?”

Every Tuesday, after getting paid, he’d walk into a local card shop and buy two packs of original Pokémon cards. He saved the rare holographic cards and sold them through the local newspaper classifieds.

One Christmas season, a grandmother called, listing out all the cards her grandkids wanted. He had almost all of them. By the end of the call, he’d turned about $60 worth of cards into $400 in cash.

That was his first real lesson in return on investment: turn $5 into $50, then into $400. It wasn’t a spreadsheet or a finance textbook. It was cardboard, scarcity, and a hungry kid figuring out margins.

Early money lessons (before any formal education)

There was no college savings account waiting. No one was opening a brokerage for him at 18. What he did have were these early, powerful lessons:

1. Money can work harder than you can. A stack of flyers pays once. A rare card can pay many times over if you buy and sell wisely.

2. Opportunity hides in everyday life. A pizza shop manager, a local card store, a newspaper ad—none of that looks like the stock market. But it’s the same muscle: spotting value and acting on it.

3. Curiosity is an asset. He didn’t just take the $5 and buy candy. He experimented. That curiosity later became the fuel for learning about investing, dividends, and financial independence.

From delinquent teen to overworked employee

His home life didn’t magically improve. He got kicked out of Catholic school in first grade. By high school, he was getting into trouble, unsupervised, and eventually kicked out of his main high school and sent to an alternative school for kids on the edge.

At 15, he moved in with his dad and got two jobs: one at a movie theater and one at a sports store. Minimum wage at the time was about $6.60 an hour. He dressed up in a ridiculous shark costume to promote a kids’ movie in front of the theater—one of the most embarrassing days of his life.

That moment burned something in: “I never want to be this powerless over my time and dignity again.” Not that all jobs are demeaning—they aren’t. But being stuck in a job you hate with no way out can be.

So he worked. A lot. Concessions, ushering, retail. No one was paying for college, so he didn’t go. That meant no student loans—but it also meant no obvious “professional” path. Just a kid with a rough past, a strong work ethic, and a growing sense that he wanted something very different from a lifetime of clocking in.

Illness, rock bottom, and a forced reset

By 25, after a decade of working, things took a sharp turn. He was diagnosed with a tick-borne illness and got very sick—down to 138 pounds, walking with a cane, and fighting for his life. Work stopped. Income dropped. The relationship with his then-wife suffered under the strain.

Chinese medicine, acupuncture, physical therapy, and a supportive dad and spouse helped him slowly recover. But financially and emotionally, he was starting from almost zero again.

Here’s the key piece: instead of deciding “this is proof I’ll never get ahead,” he drew a different conclusion. If life can change this fast, he didn’t want to wait until 65 to start living it. When doctors warn you your heart might not last as long as you thought, traditional retirement timelines stop feeling comforting.

Falling in love with a new life (and walking away from the old one)

After getting healthier, he and his wife took a trip to Puerto Vallarta, Mexico. He’d been to Mexico once before as a struggling teenager and hadn’t loved it. This time, it was different. He fell in love—with the food, the culture, the cost of living, and the possibility of building a different kind of life.

He wanted to move, maybe start a business, and eventually start a family. His wife didn’t share those dreams, and she didn’t want kids. So they divorced. He moved to Mexico alone, taught, volunteered, and worked with kids. It wasn’t glamorous, but it was aligned with what mattered to him.

Then the pandemic hit while he was back visiting his dad. Suddenly he was stuck in the U.S.—and staring at a very specific question: how do I create enough income and investments to retire in Mexico and live on my own terms?

Three intense years of delivering food and investing every spare dollar

During the pandemic, a few types of work were clearly “essential.” One of them: delivering food. So he signed up for Uber Eats, DoorDash, Grubhub, and spent every spare hour driving around affluent suburbs, dropping off takeout on doorsteps.

He ended up earning close to $200,000 delivering food over a few years. But the real magic wasn’t the gross income—it was what he did (and didn’t do) with it:

He didn’t:

• Blow it at bars or on expensive nights out (they were closed anyway).
• Upgrade his lifestyle every time he had a good week.
• Assume the money would keep flowing forever.

He did:

• Live cheaply with his dad while working insane hours.
• Read investing books at night instead of scrolling or streaming endlessly.
• Build an actual investment plan focused on dividend-paying stocks and productive assets.

Books like Pat Dorsey’s Five Rules for Successful Stock Investing, plus classics by Warren Buffett and Peter Lynch, shaped his approach. Instead of chasing hot tips, he focused on owning pieces of real businesses that generated cash.

Over roughly three years, he turned a grueling delivery schedule into a growing portfolio. That portfolio became the foundation for his early retirement and his ability to live abroad on his own terms.

If you’re curious how this kind of long grind can translate into freedom, I break down the tradeoffs and reality of it in more detail in this article on what financial freedom actually looks like.

The quiet power of not having certain expenses

There’s an uncomfortable but important part of this story: what he didn’t have.

• He didn’t have student loans. No degree also meant no debt payments eating up his 20s and 30s. That doesn’t mean college is bad—it means debt is powerful, and not having it gave him a head start on investing.

• He didn’t have kids (at least not yet). That’s a painful tradeoff for him; he wanted a family. But it also meant his monthly expenses were lower and his timeline to retirement could be shorter.

• He didn’t have a high-status job. No fancy title, no corporate ladder. That can hurt the ego—but it also made it easier to walk away and reinvent himself.

We often talk about financial independence as if it’s only about how much you earn. But it’s just as much about what you’re willing to not spend on, or delay, or give up.

That’s not to say everyone should skip college or kids. It’s to say: your path will come with tradeoffs. Be honest about them. Name them. Choose them on purpose instead of drifting into them.

Investing like an owner, not a gambler

When the delivery money started coming in, he didn’t YOLO into meme stocks or crypto. He treated investing like owning a business, not buying lottery tickets.

Key principles he followed:

1. Buy productive assets. He focused on dividend-paying stocks and companies with real earnings and durable advantages—not just hype.

2. Learn before you leap. He read, highlighted, took notes, and built a written plan. Books from long-term investors helped him avoid common traps like chasing past performance or panicking in volatility.

3. Stay consistent. Instead of trying to time the market perfectly, he kept investing as he earned—letting time and compounding do the heavy lifting.

If you prefer a simpler, more hands-off version of this approach, you might like this guide on retiring rich with mutual funds. The big idea is similar: own diversified, productive assets; stay patient; and let compounding work.

Why struggle can be a financial advantage (if you use it)

None of this is a “just work harder” fairy tale. There was real pain along the way: neglect, illness, divorce, loneliness, and the ongoing ache of not having the family he imagined.

But he did something powerful with that struggle: he let it sharpen his priorities instead of numbing them.

• Growing up hungry made him obsessed with never being that vulnerable again.
• Embarrassing jobs made him determined to build income streams he controlled.
• A scary health diagnosis pushed him to value time and freedom over status.

Struggle doesn’t automatically turn into success. But it can become fuel—if you pair it with learning, a plan, and consistent action.

The real reasons he could retire at 34

So, was it a trust fund? No.

Here’s what actually added up to early retirement:

• A brutal but clarifying childhood that made him fiercely motivated to create a different life.
• Early work ethic starting at age 10, followed by multiple jobs as a teen.
• A decade of normal jobs and living without the safety net of a degree or inheritance.
• A health crisis that made him unwilling to wait for a traditional retirement age.
• A clear vision of living abroad (in Mexico and beyond) with lower costs and more freedom.
• Three intense years of side hustling (food delivery) during the pandemic, earning nearly $200,000.
• Disciplined investing in dividend-paying, productive assets instead of lifestyle inflation.
• Big tradeoffs—no kids (for now), no college debt, no luxury lifestyle while he was building.

When you stack all of that, the outcome looks less like magic and more like a long, deliberate series of choices.

What you can take from this for your own life

Your story is different. Your responsibilities, income, health, and starting point are your own. But there are some universal takeaways you can use, no matter where you’re beginning:

1. Use what you have, where you are. He used a pizza shop, Pokémon cards, food delivery apps, and library-style learning. You might have a different mix—skills, a stable job, a spare room to rent, or a hobby you can monetize.

2. Don’t underestimate “boring” work. Food delivery isn’t glamorous. Neither is retail or cleaning or warehouse work. But if you pair any of those with low expenses and thoughtful investing, they can move the needle more than you think.

3. Invest in your brain. Books, podcasts, and patient learning about money and investing can do more for you than any single hot stock pick.

4. Be honest about tradeoffs. Early retirement isn’t free. It often comes at the cost of other dreams, at least for a while. Decide what matters most and what you’re willing to delay or downsize.

5. Let hardship clarify, not crush. Illness, divorce, job loss, or a rough childhood can become the reason you give up—or the reason you refuse to. The facts are the same; the meaning you assign is different.

Finding your own “why” (your ikigai)

One of my favorite Japanese concepts is ikigai: your reason for getting up in the morning. It sits at the intersection of what you love, what you’re good at, what the world needs, and what you can be paid for.

For him, that ikigai eventually became a mix of travel, food, meaningful connections, and sharing his journey so others could see what’s possible without a trust fund, a perfect resume, or a smooth past.

Your ikigai might look completely different. Maybe it’s raising kids in a stable home you never had. Maybe it’s doing work you care about without worrying if the lights will stay on. Maybe it’s retiring at 54 instead of 34—and that’s more than enough.

The point isn’t to copy someone else’s life. It’s to look clearly at your own, decide what you want, and then use every tool you have—your work, your spending choices, your investments, your side hustles, your grit—to move toward it.

Final thoughts

Early retirement in this story didn’t come from a trust fund, an inheritance, or a secret shortcut. It came from a long string of small, often painful decisions: to work, to save, to learn, to invest, to sacrifice, and to keep going when it would’ve been easier to quit.

You don’t need anyone’s permission to start shaping your own version of financial freedom. You just need to be honest about where you are, clear about where you want to go, and willing to take the next small, unglamorous step in front of you.

And if you’re in the thick of your own struggle right now, feeling like everyone else must have some hidden advantage you don’t: you’re not alone, and you’re not stuck. Your story is still being written.