Part 1: Are You Actually the CEO… or Just Playing One?

You don’t need a corner office or a fancy title to be a CEO.

If you’re running a business…

Managing a team…

Building a family…

Or just trying to take full ownership of your life—

You are the CEO. The question is:

Are you operating like one?

That’s what this series is all about.

It’s not just about “being in charge.” It’s about leveling up how you think, lead, and execute—so you can drive real results, not just stay busy.

And in this first module, we’re going to challenge the foundation of how you even define success in that role.

Let’s get into it.

🧭 A Personal Backstory to Set the Stage

Every year, our family goes through a powerful annual tradition we call the Reflections & Embarking process.

It’s 22 questions looking back over the past year. Then 18 more looking ahead to the next.

The goal?

To zoom out, reflect deeply, and then hit the ground running in December—already clear on our direction for the following year.

But during one round of reflections in 2021, something different happened.

We each found ourselves circling the same theme from different angles:

“How do I become a better CEO?”

Josh was already stepping more fully into his own CEO role.

I was feeling the pull to upgrade how I operate and lead.

And Dave—well, he’d worn the CEO title for years, but he too saw room for evolution.

So we decided: let’s study this. Let’s go deep. Let’s figure out what really separates average operators from elite ones—and how to apply that to not just business, but life.

This module—and this series—is the result of that journey.

🔑 Everyone’s a CEO (Whether They Realize It or Not)

Most of our Insiders are business owners. Entrepreneurs. Decision-makers.

You may not have “CEO” on your business card, but let’s be honest—you’re the one calling the shots.

And even if you’re not actively running a company, let me challenge you:

You are the CEO of your own life.

You’re the one coordinating operations. Handling finance. Making strategic decisions. Trying to move the needle while keeping the damn thing from catching fire.

You’re not just wearing one hat—you’re running an entire org chart.

And for many of you? You’re also a co-CEO in your family.

You’ve merged your life with someone else’s. Now you’re not just steering your own ship—you’re co-captaining an entire fleet.

That comes with real complexity. Real leadership challenges. Real consequences for how you show up.

But here’s the key takeaway:

Whether it’s your company, your household, or your own personal growth—you are the CEO.

So the question becomes: How well are you performing in that role?

🔍 The First Big Question: How Good of a CEO Are You, Really?

I asked this during the live session, and I’ll ask it again here:

If you had to rate yourself as a CEO—how would you score?

Are you just adequate? Above average? Are you absolutely crushing it?

Now—pause.

Don’t just rush to an answer. Instead, reflect on why you feel compelled to rate yourself a certain way.

Because the way you respond tells us something powerful.

Let’s bring in Warren Buffett for a second.

If you asked Warren, “How would you rate yourself as a CEO?”, you know what he’d probably say?

“That’s a crap question. Ask me a better one.”

Why?

Because any answer to that question—on any scale—is meaningless without clarity on what you’re measuring, how you’re measuring it, and why it matters.

Uncle Warren knows something most people don’t:

Better questions lead to better thinking. And better thinking leads to better outcomes.

So let’s take a page from his playbook.

🔁 Replace the Rating with a Real Question

Instead of “How good am I as a CEO?”, ask this:

“What are the few essential things that top-tier CEOs do better than anyone else—things that create the most value for their customers, their teams, and themselves…

…and how can I model those behaviors to improve how I operate as the CEO of my own life?”

Now that’s a question worth answering.

And over the next five modules, that’s exactly what we’re going to unpack.

But let’s start here.

📊 What the Research Says About Great CEOs

Two major sources give us a powerful window into how elite CEOs operate:

🔹 Harvard Business Review’s “CEO Genome Project”

A 10-year study identifying four things the best CEOs do better than their peers:

1. Decide with speed and conviction
2. Engage for impact
3. Adapt proactively
4. Deliver consistently

🔹 McKinsey & Co.’s CEO Research

Thousands of C-suite clients later, here’s what McKinsey found great CEOs do:

• Set a bold direction
• Align the organization
• Mobilize leaders
• Engage the board
• Connect with stakeholders
• Stay personally effective

Useful? Yes.

Memorable? Not really.

So let’s distill it into something simpler—and sharper.

The CEO’s Real Job: Think. Lead. Execute.

At the end of the day, elite CEOs excel at three things:

1. They think clearly.They ask better questions. Challenge assumptions. Zoom out before zooming in.
2. They lead intentionally.They communicate vision, mobilize people, and create alignment.
3. They execute consistently.They deliver. Iterate. Ship. They don’t stay stuck in analysis paralysis.

If you want to level up as a CEO—in any area of your life—these are the three muscles to develop.

And if that sounds overly simple?

Good. That’s the point.

🧠 What Comes Next

This was the setup. The foundation.

The rest of this series will go deeper into the specific mental models and frameworks we’ve studied and practiced in our own family office and businesses to upgrade how we think, lead, and execute.

Next up in Part 2?

Model the Masters: How Elite CEOs Actually Think

We’ll show you how to shortcut years of hard lessons by studying the right people—not the influencers, not the consensus crowd, but the outliers who consistently win.

You’ll learn:

• Why “best practices” are often a trap
• How to tell if you’re modeling the wrong people
• What Charlie Munger meant by a “latticework of mental models” (and how to build your own)

Until then—start thinking about thinking. Where, for example, would you place yourself on the diagram below? (This isn’t a trick question, btw).

Give it some thought, and I’ll see you in the next installment.