ISSUE #021 | THE LEADERSHIP CONTRARIAN

Why the expectation that sounds like a high standard is actually setting your organization up to fail.

A few weeks ago I was at my favorite Starbucks - the one between my house and the office, managed by a friend of mine I've known for the better part of twenty years. She introduced me to a new team member who had just transferred in. Already trained. Already experienced. She had worked at four or five other Starbucks locations and knew every part of the job.

I ran into that same barista again this week and asked how it was going.

ISSUE #020 | THE LEADERSHIP CONTRARIAN

The Post-Trust Era: Why the Leaders Who Already Value Trust Have to Go to the Next Level

One of my entrepreneurial friends, who has been running a successful company for over 30 years, said something to me recently that stopped me cold:

"It's just harder to make a buck these days," he said. "Our company's doing well, but you just have to work so much harder to make a dollar."

The look on his face told the rest of the story - a quiet exhaustion, and something just beneath it that felt like discouragement. He wasn't complaining. He was just being honest about something real.

I knew exactly what he was talking about.

ISSUE #019 | THE LEADERSHIP CONTRARIAN

Welcome back.

Do you ever feel like what people call random isn’t really random… and that history seems to repeat itself—but we don’t quite see the pattern while we’re in it?

There’s a pattern in history that shows up every 80 to 100 years, and it has a lot to say about what’s happening in our world right now.

And it’s not theoretical. It’s history, and it can help your leadership and your business right away.

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.