Leadership Writing and Conversations for Startup CEOs
I write and talk about what I've learned from 30 years of building and coaching. Direct. Tactical. Real.
Latest Posts
Read all on SubstackShould you rethink everything?
Why you should question...everything.
Read moreYou Need to Try Claude Code
... or why "I'm not technical" is no longer an excuse.
Read moreIt’s January and You Still Don’t Have a Plan?
You don't need a consultant. You need the right questions. A simple framework for founders stuck on strategy.
Read moreWhat Founders Get Wrong About Traction
Founders chase "traction" but don't know what it means. This breaks it down into 5 clear rungs of evidence that...
Read moreClarity is a Two-Way Street
You think you're being clear. Your team thinks they're hearing you. You're both wrong. Why clarity breaks down in both...
Read moreHow to Stop Reacting and Start Responding
or… why you shouldn't reply "F YOU!"
Read moreRecent Writing on Substack
When the playbook stops working, throw it out. How to know when it's time.
You can love the work and still walk away. Knowing when matters.
A conversation about crisis leadership and staying steady when it matters most.
Nick Francis on the decision that saved Help Scout and what it cost him.
What happens after you sell your company and lose your identity.
Turning a crisis into an opportunity when the market punches you in the face.
What it's like to become CEO on the worst possible day.
Why commitment to a single path beats hedging every time.
Making the leap from operator to advisor and what changes.
When the problem won't go away, how you deal with it defines you.
Critical Moments
Conversations with leaders about one specific moment in their career that changed everything. I talk with founders, CEOs, and leaders about the decisions that defined them; the hard calls, the lessons, the things they wish they knew.
Recent episodes
What Liana Douillet Guzmán Couldn't Unsee
When SVB collapsed, Folx Health's CEO faced a crisis that revealed deeper business truths.
Jacob Ross on Trusting Yourself and Building the Business You Can See
PebblePost's CEO on strategic pivots and the gap between good and great opportunities.
Sue Heilbronner on Losing a Role, Choosing Herself, and Selling Without Selling
After being told "I've lost confidence in you," she built a coaching practice her way.
Chris Grosso on Leading an IRL Business Through Covid
Intersection's CEO navigates 75% revenue collapse and wartime leadership decisions.
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