Evolving Beyond Safety

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Every investor starts somewhere.

Lately, I’ve been reflecting on how my own philosophy has evolved — and I thought it might be worth sharing.

Some of what I’ll say may not resonate with you, and that’s okay. This isn’t meant to be a yardstick for success, but a reminder that your approach will (and should) evolve as you do.

1. The Starting Point: Playing It Safe

I grew up in a family that believed in safety.

If we had extra money, it went straight into CDs — guaranteed, FDIC-insured returns. And back then, that actually worked.

When I was a kid, interest rates were around 8%, which was amazing. You could park your money, let someone else use it, and get paid handsomely for the privilege.

But as rates fell, the math stopped making sense. Once inflation was factored in, CDs became a guaranteed way to lose purchasing power.

That left a question hanging in the air: If not CDs, then what?

For my dad, the answer definitely wasn’t the stock market. He called it gambling — a casino for people who thought they were smarter than they were.

Instead, he put everything into farmland.

His father was a farmer, and he sold farm equipment for a living, so it made sense — it was what he understood.

And to be fair, there’s timeless logic in that. We’re not making more land, and people will always need to eat.

When he passed and I inherited his estate, I saw the wisdom in what he’d built — a tangible, productive asset that generated real value. But I also saw its limits.

Prices had risen so much that buying new farmland barely penciled out. The yields were too low to justify further investment.

It made sense to hold what I inherited — but not to double down. Owning more would’ve just overexposed me to the same market.

That’s when I realized something fundamental about investing:

And that realization pushed me to look beyond what I grew up knowing.

2. The Awakening: Discovering the Market

When I got to grad school, I knew I needed to start investing for myself.

Like most people, I started by reading everything I could. And all roads seemed to lead to the same advice:

It made sense on paper — the S&P 500 had averaged about 10% annualized returns over 40 years. And in many ways, it’s a brilliant structure.

You’re effectively buying into a self-selecting portfolio of America’s largest and most successful companies. If one falters or goes bankrupt, it’s automatically removed and replaced by a stronger performer. Over time, that means the index quietly prunes the losers and keeps the winners.

It’s capitalism on autopilot — and it’s worked incredibly well.

But that’s not to say it’s perfect.

A handful of mega-cap companies dominate the index. So “diversification” isn’t really diversification.

Furthermore, money is flooding into these funds automatically through automatic 401(k) contributions and dollar-cost averaging, meaning investors are regularly buying shares at any price.

It felt… detached. The average investor had no idea what they actually owned — and that’s often a recipe for disaster.

And if my dad taught me anything, it’s that you should understand the thing you’re investing in.

That belief became the foundation for everything I’ve done since.

3. The Experiment: Learning to See Value

In order to get more hands-on with investing, I started studying Warren Buffett and stumbled onto the concept of value investing — and it instantly clicked.

The idea was simple but profound:

You estimate what a business is truly worth based on its financials and earning power, then wait patiently for the market to offer it to you at a discount.

That framework resonated with how I already thought. It was rational. It was measurable. It wasn’t gambling — it was analysis.

So I began reading 10-Ks like novels. I’d buy a little when something looked promising — just enough to give myself skin in the game and force deeper research.

If I kept digging and still liked what I saw, I’d buy more.

And then something interesting happened.

• A few picks lost money.

• Most made some.

• But a few crushed it.

When I added it all up, my portfolio averaged 25% annual returns over five years — roughly a 3× gain in total.

I’d found a process — a way to allocate capital rationally, grounded in fundamentals.

So the sky’s the limit, right? Well not exactly…

4. The Reflection: Beyond Stocks

There are plenty of people who would kill to triple their money in five years. But for me, that success came with a deeper question: How do I scale this responsibly?

Beating the market once was thrilling. It made me feel sharp, in control — like I’d cracked the code. But that’s not how compounding works. One good run doesn’t prove you’re skilled; it proves you might have gotten it right once.

Don’t get me wrong, I think 5 years is impressive. But could I do it for another 5 years? 10? 20?

The real challenge wasn’t doing it again — it was doing it sustainably. I didn’t just want bigger returns. I wanted durability — a system that could keep winning long after the excitement faded.

This made me think of Ray Dalio, who promotes the idea to own assets with uncorrelated returns.

What he means is that no matter how good any single investment looks, there will always be periods when it underperforms — sometimes for reasons completely outside your control.

By holding assets that behave differently under different economic conditions, you smooth out the ride. When one zigs, the other zags. It’s less about maximizing returns in any one year and more about ensuring your wealth keeps compounding steadily through all market cycles.

Every new investment should compound my wealth without compounding my risk.

Neat, huh?

5. The Current Philosophy: Compounding with Intention

Today, my investing philosophy is simple:

• Own productive assets that create value — whether that’s farmland, real estate, businesses, or stocks.

• Reinvest intelligently, not automatically.

• Diversify thoughtfully, not for the sake of it.

• Balance concentration with conviction — enough exposure to win, but not enough to blow up.

In short:

That’s the real game.

💡 The Takeaway

Your investing philosophy should evolve as you do.

At first, you just want to make your money grow.

Eventually, you want your money to grow without needing you.

That’s where true compounding begins.

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