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Why Some Partnerships Last And Others Slowly Fall Apart

April 25, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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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?"

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The Right Room & the Power of Proximity

April 18, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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 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.”

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Are You Aware of the Stress You’re Carrying & What It’s Doing to Your Leadership?

April 11, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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 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

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Why Coaching Accelerates What Hard Work Alone Cannot

April 4, 2026 / by Michael Redman

posted in The Leadership Contrarian Newsletter

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 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.

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