You Might Be Building Your Empire In Your Underwear

"Missing pants" — When truth-telling is more important than appearances.

Hey friend,

You need to hear about my great-grandfather Papa Joe and a most embarrassing (yet brilliant) moment in his life.

And it speaks to why you may want to seriously consider being a member of our next Breakthrough group in January.

Picture this: Papa Joe built and lost TWO financial empires. We’re talking massive success followed by crushing losses in the depressions of the 1880s and 1930s.

But here’s where it gets good...

One day, he burst into the dining room where his wife was hosting her church ladies’ Bible study.

“I’ve got an idea!” he announces.

The room erupts in laughter. 😂

Confused, he demands, “What’s wrong with my idea?”

His wife calmly replies: “Joe, you don’t have any pants on.”

Without missing a beat, he declares: “What are pants compared to a great idea?”

I. Can’t. Even. 🤦‍♀️

But here’s what this story teaches me about leadership...

The Truth Nobody Tells You About Success

The more successful we become, the fewer people feel safe telling us the truth.

Think about it.

Who’s going to tell the empire-builder that their foundation is cracking?

Who’s brave enough to interrupt the visionary mid-idea?

Nobody. That’s who.

And that’s exactly how businesses fail.

The Shocking Reality Check 📊

Ready for this?

70% of businesses fail to transition to the second generation.

Not because of market forces. Not because of competition.

Because leaders can’t hear the warnings that matter.

When your team stops speaking up, it may not be respect—it may be resignation.

(Ouch, right?)

Here’s What Actually Works

After years of watching leaders crash and burn, I’ve discovered what separates those who thrive from those who merely survive:

1. Intentional vulnerability

Admitting you need input (even when it’s uncomfortable)

2. Structured feedback

Creating formal processes where truth-telling is expected

3. Celebrating challenge

Actually rewarding people who disagree with you

4. Peer accountability

Surrounding yourself with equals, not just employees

Because here’s the thing...

Your greatest legacy isn’t what you build alone—it’s what continues to thrive without you.

Your Turn 🎯

I’m curious...

Who in your organization has permission to tell you about your “missing pants”?

Hit reply and tell me. I read every email.

Because if you can’t name at least three people who would interrupt your biggest idea to point out what you’re missing...

You might be building your empire in your underwear.

Harry

P.S. Our next Breakthrough group starts in January. Spaces are limited, hit reply and get on the waiting list.