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Matt Munson

2x (exited) founder turned CEO coach | Helping 20 leaders at a time feel less alone on the journey. | Writing candidly about the hard stuff.

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Latest posts

What I Was Surprised to Lose When I Sold My Company

A few weeks after selling my company, I walked into our empty office and was surprised by the grief that met me there. I had spent years believing we were building a product and a business. Only at the end did I understand how much we had also been building a place to belong.

Stop Fundraising and start "Checking the Market"

How a simple mindset shift changed the way I think about fundraising.

The Value of Preserving Optionality

The founders who keep the most options available often end up with the strongest negotiating position. A few thoughts on fundraising, cash flow, exits, and preserving optionality.

Why So Many Founders Feel Lonely (And What to Do About It)

The highest-leverage investment most founders keep delaying.

Why Many Founders Keep Bending (And How to Stand Up Straight)

Many founders learned early that staying safe meant bending to everyone else’s needs. Here’s why standing up straight changes everything.

It’s ok.

The things that are feeling hard about being you today? It's ok.

Why Founders Obsessively Check Revenue (And What It’s Really About)

A CEO coaching perspective on anxiety, safety, and the deeper reason so many founders constantly refresh dashboards, email, and metrics.

When do founders get to feel safe?

Many founders secretly believe the next milestone will finally bring peace. What if the feeling you’re looking for was never going to come from the company at all?

Learning to Begin from Being

A reflection on self-worth, identity, and the shift from striving to being. How my own inner work is changing the way I lead, coach, love, and live.

Startups Are Full of Surprises

Why resilience and rapid experimentation matter so much in startups.

Honoring the Endings We Fear Most

What happens when you choose the ending you fear most? A reflection on grief, truth, and the unexpected grace that follows when we act from deep conviction.

Sanity Notes #041: The Most Important Voice in the Room

A simple daily practice to actually hear your inner voice.

When white-knuckling your way forward stops working.

Many founders succeed by pushing through pain. But the same survival strategy that built the company can quietly destroy the person leading it.

A Love Letter to Anyone Navigating Loss

I have found myself in many conversations about loss recently. This is an open letter to anyone navigating loss. You are not alone.

Is Executive Coaching Worth It? A Data-Backed Look for CEOs.

Discover whether executive coaching is worth it for CEOs. Explore data-backed ROI, leadership outcomes, and how the right coach transforms clarity and performance.