Your Next Bold Investment Starts Today
How to Know When to Bet Big, When to Walk Away, and How to Build Wealth That Lasts
When I was fourteen, I made the first bold investment decision of my life. I did not call it that at the time. I was just a kid who saved every dollar from mowing lawns, read every finance book I could find, and studied the stock pages like other kids studied baseball cards.
One small-cap stock caught my attention. I bought it. A few months later, the company was acquired, and my few hundred dollars turned into a few thousand.
It wasn’t genius. It wasn’t luck alone either. It was preparation meeting opportunity.
That tiny gain did something much bigger than grow my savings. It taught me that smart decisions, made early and consistently, create outsized results. It taught me that ‘bold’ does not mean reckless; it means intentional.
And what did I do with that windfall? A few thousand dollars felt like a fortune back then. I didn’t spend it. I didn’t upgrade anything in my life. I re-invested it. Again and again. The start of a lifelong habit that has made me truly wealthy today.
Decades later, that same principle shaped one of the best financial decisions of my life.
It started with a deal nobody wanted.
The Deal Nobody Wanted, and Why We Bought It Anyway
Twelve years ago, we bought a self-storage facility that nobody else wanted.
It had gone into foreclosure. Units sat empty. The books were a disaster. Lease agreements were scribbled by hand and stuffed into banker’s boxes like forgotten receipts.
Systems were outdated, operations were sloppy, and occupancy was stuck at forty percent. At that level, the property wasn’t bringing in enough money to cover its bills. No bank wanted to finance it. To most investors, it looked like a headache. Maybe even a warning sign.
But we knew that area extremely well, as it is right in our backyard. We knew it was great location. I had driven past that facility hundreds of times because we live nearby and do most of my real estate work in the same area. There was nothing wrong with the location. There was nothing wrong with the asset.
The bones were good. The leadership wasn’t. And that is where opportunity lives.
We wanted to buy it, but because the banks wouldn’t lend on it because it was losing money, we had to get creative. So we did something most people overlook. We turned to someone who trusted us: a past client whose custom home we had built years earlier. They believed in us enough to step in as a private lender. With financing secured, we bought the facility and went to work.
We upgraded the facility. Modernized the systems. Cleaned the books. Rebranded it so the community actually knew it existed. Most importantly, we began managing it the way a real business should be managed: with clarity, consistency, and accountability.
Progress was slow at first. Then momentum kicked in. Occupancy climbed from forty percent to nearly ninety percent. Cash flow surged. A distressed property turned into a strong, predictable income stream.
We never planned to sell, but a buyer eventually came with the right number. Because we weren’t desperate to exit, we held the leverage in the negotiations. After just four years, we sold for nearly three times what we paid.
And because we bought with leverage, the returns were extraordinary. For the finance nerds: the IRR was 74 percent per year for 4.5 years.
It felt like hitting the lottery. So what did we do with the windfall?
We didn’t buy a fancy car. We reinvested the money. That habit started when I was fourteen, and it hasn’t changed.
We rolled the profits into multiple 1031 exchanges, one of the best tools in real estate. You reinvest gains without paying taxes along the way, which lets your money compound faster. Thinking about tax strategies is one way that the rich get richer.
That single deal became the seed for two income-producing properties and two development parcels. Over 12 years, a $75,000 investment has grown into more than $7 million in assets. And those properties generate hundreds of thousands of dollars in passive income. Passive income is the best kind of income, the income that shows up while you sleep.
If you are reading this, I know a few things about you: You want the most out of this life. You care about the people around you. You are tired of sitting on the sidelines. You are tired of living the same life over and over. You want to change your money story so you can change your life story. You are ready to own your financial life, you are ready to make a bold investment.
Let’s do it!
A bold investment follows one simple rule:
It must be big enough to matter, smart enough to protect the downside, and aligned enough to support the life you want.
Those three filters, impact, protection, and alignment, guide every major financial decision I make. And they apply far beyond money.
Let’s walk through each one.
1. Big Enough to Move the Needle
A bold investment creates meaningful change. It shifts your trajectory, not just your mood.
That storage deal did exactly that. It expanded what was possible for our family, our businesses, and our future. It funded additional properties. It accelerated our passive income. It opened doors that would have taken decades to reach otherwise.
But you don’t need a real estate deal to make a bold investment. This is you getting off the sidelines and taking action.
For you, your next step might be:
Pay an extra $100 this month on your high-interest debt
Increase your 401(k) contribution
Learn about finances - you are already doing it by reading this!
Buy your first rental property
Start a small business on the side
A bold investment is something you will look back on in five years and say, “That decision changed my trajectory.”
2. Smart Enough to Protect the Downside
Before we bought that storage facility, I ran every worst-case scenario I could think of. What if occupancy didn’t budge? What if expenses climbed? What if the market softened?
If the answer to “Can I live with the downside?” had been no, I would have walked away.
Bold isn’t a blind leap. Bold is a calculated step taken with your eyes wide open.
This principle applies everywhere:
If you change careers, build savings first.
If you buy a rental property, make sure you can cover the mortgage during vacancies.
If you invest in stocks, understand your time horizon so you don’t panic when the market dips. The rich buy, not sell, on dips.
Protecting the downside keeps you in the game long enough for compounding to work in your favor.
3. Aligned with Your Values
This is the most important filter of all. A bold investment should move you closer to the life you want, not further from it. If a deal would make me more money but pull me further from my family, my health, or my purpose, it fails the test.
Because wealth without alignment becomes weight. Money that contradicts your values always feels heavy. This goes straight back to my post on knowing your values. When you are clear on what matters most, the right decisions become obvious. The wrong ones fall away.
So before every major investment, I stop and ask myself one question:
If this works, will it help me live the life I want to live?
If the answer is yes, I move forward. If not, I walk away without hesitation, no matter the potential return. That clarity took years to learn. When I was younger, I said yes to almost every opportunity. My filter was simple: “Will this make me more money?” And most of the time, the answer was yes. What I didn’t consider was the cost. The time. The stress. The way certain opportunities would pull me away from the people and priorities that mattered most.
With hindsight, I would say no to many of the things I said yes to back then. Not because they were bad investments, but because they pulled me out of alignment. That’s the real lesson: A good investment grows your financial wealth. A bold investment grows your life.
Investments Beyond Money
Not every investment shows up in a spreadsheet. Or you may be very content with your current financial situation. Some of the most transformative investments happen in the areas we tend to overlook: relationships, health, personal growth, and the way we spend our days.
A positive next step in your relationships might be choosing presence over distraction. It might look like slowing down enough to sit with your kids, taking your spouse to dinner without your phone, or keeping a friendship alive when life gets busy.
Small choices. Big dividends.
An investment in your health could be waking up early to move your body, saying no to one more drink, or scheduling the doctor’s appointment you’ve avoided. It doesn’t feel dramatic in the moment, but it compounds into decades of energy and clarity.
An investment in your growth might be reading ten minutes a day, working with a coach, setting a boundary that protects your sanity, or saying yes to something that stretches you.
These decisions follow the same rule as money: They compound. Remember, Money & Life Compounds.
A bold investment in your marriage pays dividends for a lifetime.
A bold investment in your health gives you the capacity to enjoy what you’ve built.
A bold investment in your growth multiplies your impact on the people you love.
When you start living this way, your life becomes a portfolio of bold decisions: some financial, some personal, all aligned with what matters most.
What Bold Is And What It Isn’t
Would you like to know what I’ve learned after decades of building, investing, winning, losing, and learning?
Most people don’t fail because the opportunity was bad. They fail because they misjudge the risk, ignore the fundamentals, or say yes to something that isn’t aligned.
Here are the mistakes I’ve seen, and made myself:
People chase shiny objects instead of solid fundamentals. They forget to evaluate the downside. They delegate their due diligence to someone else. They let ego make the decision instead of values. They invest money but ignore the cost in time, relationships, and health.
The real difference between Bold and reckless isn’t the size of the move. It’s the clarity behind it.
The Bigger Picture
When you look at life through this lens, everything changes.
The Wheel of Life shows us that true wealth requires balance.
Time & Money reminds us that the purpose of money is to buy back your time, not burn it.
Put those lessons together and a bigger truth emerges: Bold investing is not just about money. It is about alignment. Alignment with your values. Alignment with your purpose. Alignment with the life you’re trying to build.
Money can help you build that life. But money alone will never define it.
Take Action
Think about one decision you’re considering right now: financial or personal.
Run it through the Bold Filter:
Is it big enough to matter? Is it smart enough to protect the downside? Is it aligned with your values?
If the answer is yes, take one small step toward it this week. If the answer is no, walk away with confidence.
Start Bold (Simple First Steps):
Write down one opportunity you’re evaluating.
List the upside and the downside - on paper.
Ask yourself: Will this help me live the life I want to live?
Bold decision-making is a muscle. The more you use it, the stronger it gets.
Ask Me Anything
If this brought something to mind or stirred a question for you, I’d love to hear it. I’m starting a video AMA here on Substack where I answer your questions about wealth, decision-making, and building a life that actually lasts. Leave your questions in the comments, and I’ll cover them in an upcoming AMA.
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Really fantastic material Chris, well done! BOLDly going where no one has gone before!!
Another great read. These articles on a weekly basis are EVERYTHING for an inspiring investor like myself working on making BOLD investments!