Simple, Not Easy: What Warren Buffett’s Letter to Bertie Teaches Us About Investing Like Owners

When people hear about Warren Buffett’s investing strategy, they often imagine it must be incredibly complex—an elite process reserved for those with MBAs and decades of Wall Street experience.

But the truth is much simpler.

The kind of investing Buffett practices—and that we teach through Rule #1—is not complicated. In fact, it’s profoundly straightforward. You’re looking to buy wonderful businesses at attractive prices. You’re investing like an owner. And you’re staying within your circle of competence.

The hard part? Doing that consistently.

Sophisticated Simplicity Is a Real Thing

Danielle and I started with a conversation about the strange paradox of simplicity in value investing. On the surface, it’s about as basic as it gets: understand the business, know what it’s worth, and buy it with a margin of safety.

But doing that well takes real work. It’s like tailoring a perfect suit or decorating a minimalist home—it might look effortless, but it requires deep attention to detail and mastery of fundamentals.

“Sophisticated simplicity is one of the hardest things to achieve.” – Danielle Town

Investing the Rule #1 way demands a kind of focus and humility that many people skip in favor of chasing fast results. But here’s the good news: you don’t need to be an expert to get started.

Could You Run a Rental Property?

One of the most important principles in Rule #1 investing is this: only invest in businesses you understand. But what does that really mean?

Here’s the analogy I use: ask yourself if you could own and operate a rental house in your neighborhood. Could you figure out the taxes, upkeep, tenant selection, and rent pricing? Could you manage the basics?

If your answer is yes—then you already have the capability to understand a business. Because when you boil it down, investing is just owning a piece of a company. It’s not about watching stock tickers or predicting market moves—it’s about understanding how that business works and why it will continue to thrive.

And if you don’t feel confident yet? That’s okay. Keep learning. Read. Ask questions. That’s what this journey is all about.

Guardrails Aren’t Limitations—They’re Freedom

We often talk about Rule #1’s "four Ms"—Meaning, Moat, Management, and Margin of Safety. These aren’t just filters; they’re guardrails. They keep you focused on companies that meet your standards, so you don’t get distracted by hype or media noise.

When you’re learning to drive, guardrails on a mountain road don’t restrict you—they keep you safe while you improve. Same goes for investing.

And even when you’ve been at it for years (like I have), sticking to those guardrails is how you avoid painful mistakes.

Even Simple Things Benefit From Coaching

I’ve been snowboarding for over two decades. And yet, every time I get back on the mountain, I hire a coach. Why? Because no matter how long you’ve been at something, there are always ways to improve. There are always blind spots.

The same goes for investing.

Buffett had mentors. So did I. And I still believe in the power of learning from others. Whether it’s a podcast, a class, or a trusted advisor, getting outside perspective can sharpen your thinking in ways you can’t do alone.

What Buffett’s Letter to Bertie Reminds Us

In Warren Buffett's 2013 annual letter, he did something remarkable: he wrote the letter as if he were speaking directly to his sister, Bertie. She’s not a CPA. She’s not a hedge fund manager. But she’s smart, sensible, and informed. She reads four business publications daily. She asks tough questions.

“She knows who is ‘selling’ and who can be trusted. In short, she is nobody’s fool.” – Warren Buffett

That description struck a chord with us. Bertie represents the kind of investor Rule #1 is built for. Someone who may not be a financial expert, but who’s willing to read, think independently, and trust their own common sense.

Buffett’s point? If you're intelligent and curious, you can understand business and make smart investment decisions. You don’t have to be a professional. You just have to care enough to learn.

Media Is a Distraction—Not a Strategy

Danielle and I have both done our fair share of interviews on financial news shows. And let me tell you, those four-minute segments you see on TV? They take hours of preparation. Between travel, makeup, production, and scripting, it’s a major production just to say a few words.

So when you see someone from a hedge fund sitting in a chair on a cable show telling you to buy a stock, ask yourself: Why are they there?

The reality is, many so-called pundits are simply “talking their book.” They’re pumping up stocks they already own in hopes of driving prices higher. And if you’re not aware of those incentives, you’re going to get played.

Buffett knows this. That’s why he praised Bertie for her healthy skepticism. She doesn’t trust everything she hears, and neither should you.

It’s Okay That It’s Not Easy—That’s What Makes It Worth Doing

If this process feels challenging at times, don’t worry. It’s supposed to be. Anything worth mastering takes time and repetition. You’re not trying to predict the next hot stock. You’re building a lifelong habit of smart decision-making.

And when you hit a wall? That’s when you lean on your tools, your community, your education—and yes, your coach.

Because even simple things benefit from structure. Even good investors need reminders. And even Warren Buffett writes his letters with someone specific in mind—someone like Bertie. Someone like you.

Ready to Invest Like an Owner?

If this blog resonated with you—if you’re the kind of person who wants to invest with confidence, understand businesses deeply, and think like Warren Buffett—then our 3-Day Rule #1 Investing Workshop is your next step.

This workshop is designed for people who are ready to take investing seriously. Whether you're new to the stock market or looking to sharpen your strategy, you’ll learn exactly how to:

• Identify businesses that you truly understand

• Evaluate their financials and determine intrinsic value

• Know when to buy with a margin of safety

• Avoid hype, noise, and risky speculation

This is not a lecture—it’s a hands-on, highly interactive experience that will give you the tools and clarity to start investing the Rule #1 way.

Join us at the next live workshop and learn to invest like an owner.