How I Made My First Million (And the Mistakes That Almost Cost Me Everything)

What I got right, what I got wrong, and how to build wealth without losing it all.

A letter from the bank almost wiped me out.

Two loans. One million dollars. Thirty days to pay. And nowhere near that much cash in the bank.

It was 2008, the economy was collapsing, and everything I had spent a decade building was suddenly at risk.

Photo by Christopher Burns on Unsplash

But to understand how I ended up here, and how I survived it, you have to rewind.

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Framing Houses To Build Capital

Fresh out of college in the late 1990s, my brother and I started at the very bottom of the construction world. For the first few years, our “building company” was the two of us framing houses for another builder.

Most framing crews had eight guys. We had two. But we had something that mattered more than headcount. We had grit, and we were willing to outwork and outthink everyone.

We were paid by the job, not by the hour. I would always find another house nearby that was being framed and use it as my benchmark. If their eight-man crew could frame it in a certain amount of time, my mindset was simple: two of us should beat them.

We framed from sunrise to sunset. I ran the numbers and realized we were effectively making $50 to $75 an hour each in late 90s dollars. That was real money for two young guys with no connections and no capital.

And I did not spend it. I lived incredibly lean. Cheap rent. No fancy toys. Bought cars that had hit a plateau in their depreciation. Every dollar had a job: build a future.

I knew that anything I saved could be reinvested in myself and my business, and would later multiply. So while most people in their early twenties were buying fancy cars, I was saving cash and investing.

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The First Spec Home And The First Million Steps

After a year or two of framing, we had saved enough to build our first spec home.

A spec home is a house a builder constructs without a buyer in place. You take the risk in exchange for the potential reward. We reduced the risk by doing as much of the work as we could ourselves, which kept the build cost low.

The bank was willing to lend us the money, after much begging, because we had real skin in the game. Our savings were in the project. The loan amount compared to the finished home value was very low, so the bank’s risk was lower.

We built it fast. It sold right away. It was a win. But the biggest payoff was not the profit; it was what happened next. A woman saw that home and said, “I love this. Will you build one for me?”

That was our first custom home client.

With a custom home, the client buys the lot and either brings cash or gets their own construction loan. The builder earns a profit on building the home for the contract price. It is far less risky than a spec project because you are not carrying the land and construction financing yourself.

That first custom build changed the trajectory of our business. It gave us stability, not just upside.

This is a theme that you will see repeated throughout my story. Big wins are great; repeatable wins are better.

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The Information Edge: Becoming “The Chapel Hill Real Estate Experts”

Around the same time, I decided to get my real estate license. I did not become an agent because I dreamed of putting my face on a billboard. I wanted information.

This was 1997. There was no Zillow, no Realtor.com. If you wanted to know what a property sold for, you drove to the Register of Deeds and flipped through giant Grantor and Grantee books. Or you became a Realtor and got access to the MLS.

So I joined the association, bought a modem, and literally dialed in. The high-pitched screech of that connection meant access to something incredibly valuable: data.

I could now see lot prices, home prices, and trends across neighborhoods. And once I could see the numbers, the opportunities jumped out.

There might be a neighborhood where lots were selling for $50,000 and finished homes were going for $500,000. Then a nearby neighborhood where similar lots were $100,000, but the finished homes were only selling for $450,000.

Why would anyone pay double for a lot that would produce a home worth less when it was finished?

Two reasons:

1. Lack of access to information.

2. Lack of financial intelligence.

I wanted neither of those to be my problem.

So instead of hanging my license with another company, I started my own. I called it “Carolina Brokers Realty.” I created my own logo. Filed my own paperwork. Did my own taxes. My philosophy was simple: pay no one unless absolutely necessary.

My scarcity mindset helped me keep overhead low and margins high. But it also kept growth small. At the time, I did not understand that trade-off.

At night, after full days framing homes on the jobsite, I taught myself how to build a basic website. It was one page with a simple headline: “The Chapel Hill Real Estate Experts.” I was not an expert yet, but I was willing to become one.

I remember the first call I ever got from that website. I rushed home from framing, took a quick shower, and showed them homes. They ended up buying a house for $250,000. My buyer agent commission was 2.5 percent, or $6,250.

I bought a laptop for about $1,000 and saved the rest. That pattern repeated for years. Earn. Invest. Repeat.

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Three Jobs, One Goal: Become A Millionaire

By my mid-twenties, I was wearing three hats.

Builder. Real estate broker. And mortgage broker.

Why would I add a third job when the first two were already growing? The answer was simple: I was motivated by money, and I wasn’t afraid to work. Back then, my mindset was that if there was money to be made, I would find the time to make it. Free time felt optional. Opportunity did not.

What I didn’t understand yet was the real cost of that choice. Every time you say yes to one thing, you are saying no to something else. You are trading your time, and remember time is your most valuable asset.

Becoming a mortgage broker was my first and only time working for someone else. I did it part-time, maybe 10 to 20 hours a week, yet consistently ranked as one of the top producers in the company. Numbers came naturally to me, and I liked helping people solve financial problems. And the commission income was strong.

But I knew it was still a job. It relied on me as the talent. Long term, I didn’t want to depend on a job. I wanted to grow companies and investments that could make money even when I was not grinding every hour.

So I treated the mortgage income as fuel. It gave me additional capital to reinvest into real estate and the construction business.

I was single and had no kids. My philosophy was simple: I can work as much as I want. If I was not out with friends, I was working. Nights, weekends, whatever it took.

By 2003, at age 27, I had a net worth of one million dollars. Much of this money was tied up in assets that were not quickly or easily accessible. And I did not feel or act like a millionaire. I was working all the time, keeping costs low, and carrying a lot of the load myself.

Looking back, I did a few things very right:

• I lived below my means.

• ‘I reinvested aggressively.

• I studied money and markets.

• I kept my word with clients and banks.

But I also made some big mistakes.

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The Mistakes That Slowed Me Down

If I could go back and talk to my twenty-something self, I would tell him two things.

First: learn from people who are already where you want to go.

I was stubborn. I thought I could figure everything out myself. So I made every mistake firsthand. I would fail, get frustrated, and then let that fuel me to do better next time.

That mindset built resilience, but it was slow. I could have shortened the learning curve dramatically by working under someone great for a few years. I should have learned from the best. Start from their ceiling instead of your own floor.

Second: raise capital and share the pie.

My scarcity mindset said, “Why would I give up ownership to an investor?” So I tried to do everything with my own money.

It worked, but it capped growth. I ended up owning 100% of a smaller pie instead of a smaller percentage of a much larger pie.

Eventually, many years later, I shifted into more of an abundance mindset. I’ve brought in partners, shared deals, and realized something important: your net worth grows a lot faster when you stop insisting on owning every slice. Only then did my net worth start to grow exponentially.

Those were the strategic mistakes. Then there were some big external shocks.

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The Letter From The Bank

In 2008, I opened a letter from the bank that nearly erased ten years of work. We had a spec home under construction and a lot ready for the next one. Same bank as always. Same construction loans we had renewed year after year. I expected another routine extension.

Instead, the letter said this: Your notes are due in full in 30 days. Total owed: roughly one million dollars. Total cash in the bank: nowhere close.

It was the start of the Great Recession. Banks were tightening overnight. No other bank was going to refinance a new builder, which meant the message was clear: pay up or face foreclosure.

That was the moment I learned the difference between being a millionaire on paper versus actually having a million dollars in liquidity. My net worth was strong on paper, but paper wealth does not protect you when the bank wants cash.

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Walk away, or get resourceful? I chose resourceful.

I had never missed a payment. My credit was perfect. But none of that mattered in a collapsing market. The bank was calling in every construction loan they could.

Defaulting was not an option for me. When I sign my name on a loan, that is my word. And my word matters more than any single deal.

So I humbled myself and picked up the phone. I called the few people I knew who had both the means and the trust in me to help.

One previous client stepped in. He wrote the check, paid off the loans, and essentially became the new bank. It was one of the biggest reliefs of my life at the time. In that moment, the pressure that had been crushing my chest for days finally loosened. His trust bought us time, and time is everything in a crisis. If we had not paid off the now due note, we would have lost both properties. The bank would have foreclosed, ten years of work could have vanished, and my entire trajectory might have looked different.

Instead, we finished the projects, sold both at a profit, and lived to fight another day. Not the home run we hoped for, but far from the disaster it could have been.

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Lessons From the First Million

Looking back, a few lessons stand out.

Learn from others. For too long, I tried to figure everything out myself. It worked, but slowly. Learning from people who have already achieved what you want accelerates everything.

Plan for the unexpected. Crises are rare, but they do happen. The Great Recession, COVID, interest rate spikes, material shortages: each one taught me to build buffers and prepare for volatility.

Use financial intelligence. Information is leverage. Knowing your numbers, understanding loans, tracking net worth, and studying market patterns gives you an edge.

Choose abundance over scarcity. I held onto everything early on, afraid to share the pie. In reality, more capital and more great people would have created a much larger pie.

Protect your word. Money comes and goes, but trust compounds. In tough times, your reputation is worth more than any balance sheet.

These lessons didn’t just help me survive the downturns. They shaped how I build, invest, and think about wealth today.

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Your Turn + Start Bold

If the unexpected hit tomorrow, how prepared would you be?

Most financial stress does not come from million-dollar problems. It comes from real life: a medical bill, a job shift, a car repair, or a parent who suddenly needs help.

Preparation is not about fear. It is about confidence.

Start with one small action this week:

• Get clear on your numbers. List your debts, who holds them, and the basic terms. Awareness is the first step toward control.

• Build your buffer. Set aside a little money consistently. Even a small weekly amount creates protection over time.

• Strengthen your financial habits. And if you want practical places to begin, revisit the list of 16 Strategies for Growing Your Financial Wealth. Even one idea from that list can strengthen your foundation.

What is one step you can take this week to make yourself more prepared for an unexpected financial crisis?

Share it in the comments. I would love to hear it.

P.S. The habits you build before a storm are the ones that protect you during it. Start one today.

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Why We Build Wealth

At BOLD Wealth, we believe financial intelligence is critical, but money is still not the goal.

We build financial wealth not for status or scorekeeping, but to use it as a tool to fuel the areas of life that matter most. Family. Health. Growth. Generosity. Joy.

That is what it means to build BOLD Wealth: a life that is rich in money and meaning.

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