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Why Thinking Like a Business Owner Leads to Smarter Investing

Phil Town
Phil Town

What If You Could Only Own One Company?

I want to challenge the way you think about investing. What if you could only own one company for the rest of your life? That single mental model has had a profound impact on how I evaluate businesses. It pushes me to dig deeper, to get more serious, and to invest with more conviction.

In Rule #1 investing, we don’t buy stocks. We buy businesses. And if you wouldn’t be thrilled to own the entire company, why would you even own a single share?


Think Like a Business Owner, Not a Stock Picker

When we think of ourselves as stock investors, it’s easy to fall into the trap of treating the stock market like a casino. But when you think like a business owner, the game changes entirely.

Instead of asking, “Will this stock go up next quarter?” you ask, “Is this a business I’d want to own for the next 10 years or more?” That’s the Rule #1 mindset.

This perspective leads to more:

  • Patience – because you’re focused on long-term value.

  • Rigor – because you want to deeply understand what you own.

  • Discipline – because you’re not chasing the next shiny object.

Buffett’s 20 Punch Card

Warren Buffett once said that if you were only allowed to make 20 investments in your entire life, you'd be a better investor. Why? Because you'd think harder and demand a greater margin of safety with each decision.

But I like to make it even more extreme: What if you could only own one company? That forces you to elevate your standards and dig even deeper.

If you were going to own just one company, would it be this one? That’s the level of seriousness we need as investors.



A Real-Life Example: Evaluating a Small Envelope Company

Let me take you behind the scenes of a real investing scenario I had been exploring: a small, under-the-radar company in the envelope and packaging industry. This isn’t some flashy tech stock. It’s envelopes—and yet, it might represent the exact kind of investment we seek in Rule #1.

This company is so small that I could probably buy the whole thing, which makes it a useful mental exercise. Here’s how I approached it.

Step 1: Seek Expert Guidance with SCORE

One of the first things I did was reach out to SCORE, a free resource that pairs entrepreneurs with retired business executives. I asked them to connect me with someone familiar with the envelope or packaging industry. Even though this isn’t a startup, they were incredibly helpful.

This is a reminder: Never underestimate the value of expert insight—especially in industries you know little about.

Step 2: Deep Dive into 10-Ks Over Time

Next, I pulled the company’s 2014 and 2023 10-K reports and reviewed them side-by-side.

What I was looking for:

  • How the business model evolved over time

  • Whether management followed through on long-term strategies

  • Signs of durable growth or looming challenges

What I Found:

  • In 2014, the business was almost entirely envelopes. Now, a significant share of revenue comes from packaging.

  • Management clearly saw the envelope market declining and made a long-term strategic shift.

  • They’ve been rolling up other companies and expanding their footprint in packaging.

  • But… the company is now recording large write-downs in goodwill and intangible assets.

That last point is critical. These write-downs raise serious questions:

  • Are the acquisitions underperforming?

  • Is management overpaying for growth?

  • Or is this standard depreciation of intangible assets?

This is where investing gets real. You’ve got to dig deep and understand why those financials look the way they do. It’s not enough to see a growing revenue line—you have to understand the quality and sustainability of that growth.

They’ve been telling shareholders where they’re going for a decade. I’m barely impressed—but they’re deliberate.


Passion vs. Profit: What Really Matters?

A common question I hear is: Should I only invest in companies I’m passionate about?

My take: You don’t need to love the product. You need to love the business.

Most of the world’s wealthiest people didn’t follow their passions. They built wealth through difficult, often boring industries—think industrial shipping, insurance, mining, or packaging. What they did have was a deep understanding and strategic vision.

When I evaluate a company, I ask:

  • Do I understand how this business makes money?

  • Can I see where this business will be in 10 years?

  • Is this a business I’d be proud to own?

  • Does it align with my values?

You might not dream of envelopes. But if the company meets all four of the Rule #1 criteria—meaning it has:

  • Meaning (it aligns with your values)

  • Moat (a durable competitive advantage)

  • Management (trustworthy and talented leaders)

  • Margin of Safety (you’re buying it below its value)

… then it might be a better investment than the flashy tech stock everyone’s chasing.


The Four M's For Successful Investing

How to invest with certainty in the right business at the right price


Lessons You Can Apply

Whether you're looking at a massive blue-chip or a tiny envelope company, these lessons apply:

  1. Invest like you own the whole thing. This makes you more serious and selective.

  2. Compare past and present 10-Ks. It reveals strategic direction and management consistency.

  3. Don’t confuse passion with profit. Understand the business and invest with clarity.

  4. Ask: Would I be okay owning just this company? That question can prevent you from making mediocre decisions.


Call to Action: Ready to Dive Deeper?

If you want to learn how to think like a business owner and identify wonderful companies at wonderful prices, join me at our 3-day Rule #1 Investing Workshop.

This is where we walk through:

  • How to find companies you understand

  • How to calculate true value

  • How to recognize a margin of safety

  • And how to confidently invest like a business owner

Attend a Rule #1 Workshop

Learn how to conduct research, choose the right companies for you, and determine the best time to buy.