ISSUE #018 | THE LEADERSHIP CONTRARIAN

Kathryn and I were invited into an upper-division university class last week to talk about marketing and leadership. We spent time talking about principles - things that don't change, even when everything around them does. In a world where people chase tactics and trends, it was refreshing to stay grounded in what actually lasts.

The conversations were good and the questions were thoughtful, but one question at the end stuck with me.

A student asked, "How have you and your wife been able to work together for 23 years?"

 ISSUE #017| THE LEADERSHIP CONTRARIAN

Last week I spent two days in Cambridge with a small group of experienced business leaders brought together by my friend, Ryan Levesque.

We weren’t there casually. This was a mastermind - an intentional space where each of us came prepared to put our business on the table. One at a time, we each had about 30 minutes in what’s called a “hot seat.”

 ISSUE #016| THE LEADERSHIP CONTRARIAN

I remember listening for my dad’s footsteps when he came home. Not because I knew I’d done something wrong… but because I didn’t know what version of him was walking through the door.

Some days were fine. Some days weren’t. And you could feel the difference before a word was ever spoken. Your body would tighten. Your guard would go up. You’d brace for what might happen next.

But that wasn’t my only experience growing up.

When I spent time with my grandparents, it was completely different

 ISSUE #015| THE LEADERSHIP CONTRARIAN

Over the last 35 years, I’ve had a front-row seat to something I can’t ignore.

I’ve seen leaders get the help they needed and navigate challenges they didn’t think they could overcome.

And I’ve seen leaders just as capable stay stuck in the same patterns for years.

Same level of effort. Same level of intelligence. Very different outcomes.

 ISSUE #014| THE LEADERSHIP CONTRARIAN

When gold is pulled from the ground, it doesn’t look valuable. It’s mixed with dirt, rock, and impurities.

So what do they do?

They apply heat. Not a little heat - extreme heat. Volcanic, dragon-breath kind of heat.

And something interesting happens when the temperature rises.

ISSUE #013| THE LEADERSHIP CONTRARIAN

Last week,I wrote about something deeply personal: why we build our businesses in the first place.

So that when life happens, we have the freedom to respond like humans.

To show up.
To be present.
To do what actually matters.

If you read that, you know it wasn’t just about business.

It was about life.

This week is different.

ISSUE #012| THE LEADERSHIP CONTRARIAN

As I write this, I’m sitting in a small Airbnb in San Francisco.

Not because I’m on vacation.

I’m here because my sister has brain cancer.

Last week she began a six-week protocol of daily radiation treatments here in the city. It’s all still very new for our family, and we’re learning the rhythm of this journey one day at a time.

ISSUE #011| THE LEADERSHIP CONTRARIAN

I believe thriving should be normal in business.

But there’s a problem.

We’ve normalized “average”.

And in the process, we’ve watered down the very idea of thriving.

For decades, most of our systems - education, management, leadership development - have aimed at a simple goal: move people up to average.

If someone struggles, we help them reach the middle of the bell curve.

And if someone rises far above it, we treat them as the exception. Something unusual. Something rare.

"Good for you," we say. "You’re one of the special ones."

But average was never meant to be the goal.

ISSUE #010| THE LEADERSHIP CONTRARIAN

What Are You Actually Building Your Business For?

What’s the end goal?
And how will you know when you’ve reached the elusive finish line called “enough”?

Before we go any further, hear this:

I want the best for you. I want you to build a successful business and live a deeply satisfying life. I want you, when you’re old, to be able to say:

I lived well. I loved my family well. I built something meaningful. And the people who mattered most were still there at the end.

ISSUE #009 | THE LEADERSHIP CONTRARIAN

Hire Slow. Manage Less.

Most managing problems are hiring problems in disguise.

Not all of them.

But most of them.

When leaders tell me they’re exhausted from micromanaging…
When they say they don’t trust their team to follow through…
When they’re stuck dealing with the same performance issues over and over again…

I almost always ask the same question: