Executive Coaching for Startup Founders

Founding a company changes as the company changes.

At first, you’re doing almost everything yourself. You’re talking to customers, shaping the product, recruiting the first team, pitching investors, fixing whatever broke overnight, and making dozens of decisions nobody else can make.

Then, if things work, your job starts becoming something entirely different.

You hire leaders. You have a board. Decisions travel farther before they come back to you. The people who helped you get here aren’t necessarily the people you need next. You need to delegate things you still care deeply about. And somehow you’re supposed to make that transition while continuing to build the company.

I’ve lived this.

I co-founded Reaction Commerce and served as its CEO from zero to acquisition. We raised venture capital, built a distributed team and open-source community, changed strategy more than once, hired executives, made mistakes, worked with a board, and eventually sold the company to Mailchimp.

Today I coach founders navigating many of the same questions.

What founders bring to coaching

There isn’t one founder problem, but there are patterns I see again and again:

Am I working on the right thing?
Should we keep going or change direction?
When do I stop doing this myself?
Who should my first executives be?
How do I hold someone accountable without taking their job back?
I have too many direct reports. What should the organization look like?
My co-founder and I aren’t aligned.
My board wants one thing and I want another.
Someone who was perfect for the company two years ago isn’t working now.
I can’t tell whether I’m burned out or whether I don’t want to do this anymore.
The company needs a different CEO than it needed at the beginning. Can I become that person?

These questions look organizational from the outside. Often they’re also deeply personal.

From founder to CEO

One of the strangest parts of building a company is continually becoming qualified for a job you’ve never done before.

The skills that make someone an exceptional founder—urgency, conviction, involvement in everything, willingness to break things—can eventually collide with the skills required to lead a growing organization.

The goal isn’t to stop being a founder. It’s to become more intentional about when your founder instincts are helping the company and when they’re getting in its way.

That’s work I particularly enjoy.

How I coach founders

I’m not there to run your company for you or give you a founder playbook.

I ask questions, challenge assumptions, notice patterns, share relevant experience when it’s useful, and help turn ambiguity into something you can examine.

Sometimes we leave a session with a decision. Sometimes with a difficult conversation you need to have. Sometimes with an experiment. Occasionally the most useful outcome is realizing that the problem you arrived with isn’t actually the problem.

My job isn’t to make you more like some imaginary ideal CEO.

It’s to help you become more intentional about the founder and leader you want to be.

Work with me

I work with founders from early-stage and zero-to-one companies through venture-backed growth, acquisition, and the transition into larger organizations.

If you’re wondering whether we’d work well together, start with a free introductory conversation.

Schedule a free introduction, or read more about how coaching works.