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.
All Posts
Read all postsThe CEO Loneliness Problem
The CEO role is structurally isolating. Here’s why it happens, and what actually helps.
Read moreCulture Doesn’t Just Happen. You Must Build It.
Most founders think culture takes care of itself. It doesn’t. Here’s how to build company culture intentionally as a startup CEO.
Read moreThe Friday Update Template Every CEO Should Steal
A practical CEO weekly update template with real examples, the full structure, and how to make it a leadership habit.
Read moreShould 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 actually matter.
Read moreClarity is a Two-Way Street
You think you’re being clear. Your team thinks they’re hearing you. You’re both wrong.
Read moreHow to Stop Reacting and Start Responding
or... why you shouldn’t reply "F YOU!"
Read moreConsensus Kills
Who owns this decision? If the answer is "we both do," you’ve got a problem.
Read moreThe Case for Daily Stand-Ups (Yes, I Mean You)
Most meetings suck. This one doesn’t. Fifteen minutes a day.
Read moreClarity First
If your team doesn’t know exactly what success looks like, that’s not their fault. It is your fault.
Read moreYou Fucked Up, Now What?
A simple framework to fix when you mess up.
Read moreThe Dangers of Autopilot
Every day I drive past a deli with the same sign. Don’t be that deli.
Read moreHow to Make Your To Do List
The Now, Next, Later, Always framework for CEOs who are overwhelmed.
Read moreMore! Faster! Now! Forever?
The Relentless CEO in the Age of AI
Read moreWhy You Should Send Friday Updates
The One CEO Habit That Builds Trust Every Week
Read moreHow to Have Hard Conversations
Most leaders avoid them. Here’s how to stop.
Read moreBrad Feld’s Give First and the Long Game of Generosity
What a book about venture capital taught me about coaching.
Read moreSaaS Math Doesn’t Work in an AI World
The metrics we’ve relied on are changing. Fast.
Read moreWhen CEOs Should Be Involved
The hardest judgment call in leadership.
Read moreWhat Do You Need From Me?
Clarity, Focus, and Urgency — the three things every CEO owes their team.
Read moreTapas for One
On loneliness, boundaries, and the parts of the CEO job nobody talks about.
Read moreYou Don’t Have to Pretend to Be "The CEO"
What happens when you stop performing the role and start living it.
Read moreWhen Losing Your Voice Leads to Finding It
A critical moment about identity, authority, and what it means to lead.
Read moreGetting Back to It
How to restart after a setback, a break, or a loss.
Read moreDouble Opt In Warm Intro
The right way to make introductions — and why most people get it wrong.
Read moreFree Workshop: Prompt Engineering for Humans
What I learned from teaching non-technical people to use AI.
Read moreHow to Interview a CFO
The questions that actually matter when hiring your first finance leader.
Read morePrompt Engineering for People
How to get better answers from the humans you work with.
Read moreBuild It. Nail It. Scale It.
The three phases every startup goes through — and what changes at each one.
Read moreBuild the Model. Do the Work. Know the Business.
Why the CEO needs to understand the numbers at a bone-deep level.
Read moreFind Your Simple Math
Every great company can explain its business in one equation.
Read moreHow to Interview a CTO
The questions that actually matter when hiring your first technical leader.
Read moreHow to Interview a Product Leader
What separates great product leaders from the rest.
Read moreHow to Write a Job Description for a Senior Role
Why most JDs fail — and how to write one that attracts the right people.
Read moreSet Goals You Can Fail At
The only goals worth setting are the ones that scare you a little.
Read moreWhat It Really Takes to Bet the Company
On big decisions, strategic pivots, and having the courage to go all in.
Read moreWelcome to How to CEO
Why I’m writing this newsletter and who it’s for.
Read moreYour Career Is Not a Suicide Pact
On leaving jobs that are killing you, and the courage it takes.
Read moreFear Lives in the Unknown. Replace It with Facts.
The antidote to anxiety is information.
Read moreWhen You’re No Longer Who You Were
On identity shifts, role transitions, and the grief of leaving a job you loved.
Read moreShitty First Drafts: The Secret to Getting Unstuck
Anne Lamott was right. The only way out is through.
Read moreTrust Your Spidey Sense
On gut instinct, pattern recognition, and why your body knows before your brain does.
Read moreHow to Create Real Urgency Without Causing Panic
The difference between urgency and anxiety — and why it matters.
Read moreRepeat. It’s the CEO’s Job. Repeat.
Why you have to say the same things over and over — and how to do it without driving everyone crazy.
Read more3 is My Magic Number
Why the rule of three is the most powerful tool in leadership communication.
Read moreThe Power of Mentalization in Leadership
What happens when you learn to see the world through someone else’s eyes.
Read moreWinning Isn’t The Goal in Cofounder Negotiations
On co-founder dynamics, disagreement, and the difference between winning and getting it right.
Read moreKicking the Can: The Cost of Avoiding Hard Decisions
The longer you wait, the more it costs you.
Read moreIt’s the Feelings, Stupid!
What leaders get wrong about motivation, culture, and why people do what they do.
Read moreFrom Gut Punch to Exit
A critical moment about resilience, leadership under pressure, and finding the path forward.
Read moreThe Truth About the Best Talent
What separates good from great — and what it actually takes to build a great team.
Read moreYou Suck AND You Rock!
On holding both truths at once — and why the best leaders do.
Read moreHappiness is a Well-Fed CEO
On taking care of yourself as a prerequisite to taking care of your company.
Read moreWhy Your First Move in a Crisis Should Be Calm
The counterintuitive truth about crisis leadership.
Read moreBurn the Boats: Why You Need to Go All In
On commitment, half-measures, and what it actually means to be all in.
Read moreTake That Call
On saying yes to the unexpected conversation that changes everything.
Read moreEmbrace Resilience
On bouncing back, building toughness, and why resilience is a leadership skill.
Read moreHow to Fail: A Masterclass
Everything I’ve learned from my biggest mistakes.
Read moreRelationships Matter
On the long game of investing in people before you need anything from them.
Read moreWouldn’t It Be Great if…
On wishful thinking, strategy, and why hoping is not a plan.
Read moreRealTalk™: The Gift of Honest Communication
Why the kindest thing you can do for someone is tell them the truth.
Read moreRituals: One Way to Find Balance
The practices that keep me grounded when everything else is chaos.
Read moreHow Can I Help?
The three most important words a leader can say.
Read more5 Slides to Clarity: Simplify Complex Business Challenges
A framework for turning complicated problems into clear decisions.
Read more
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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