Allie Stark on becoming a relaxed founder who still gets what she wants

I don’t know about you guys but 2026 for me is certainly earning it’s title as year of the fire horse. I truly feel like I’ve been riding a fire breathing horse bareback at full speed. I’m just here holding onto the mane for dear life and he’s burning down what use to be. If you feel the same way, then this episode is for you.

Last week I sat down with Allie Stark and it ended up being one of the most useful, fun, and fulfilling conversations I’ve had in a good minute. Allie coaches ambitious women through big chapters of growth and change, and she put articulate language on the experience of change. The way of being that got you here isn't going to get you there, and the in-between, the part where the old self is leaving and the new one hasn't shown up yet, is messy in ways nobody really warns you about. For some of us, it’s dramatic, for others it’s not, but I think it’s universal for everyone, especially us founders.

We cover a lot in this episode. The feminine economy, and what it looks like to build a business on generosity and reciprocity instead of grinding. The kind of leader who can actually change you. Why entrepreneurship is essentially identity work in disguise. And the single most concrete exercise to do during times of change. I did it over the weekend.

But the part of this conversation that genuinely changed how I'm thinking about my life right now was when I told Allie my deepest fear: what if I work so hard but I don’t get what I want. She didn't hand me a pep talk. She asked the question back at me sideways: what if you could be more playful and still get what you want? I've been thinking about that in every single instance of my life since. For anyone who runs on hustle and worries it might not actually work, that question is the whole episode.

For the early-stage founders listening, especially the women: we are in a wildly transformative cultural moment, and if the old way of doing things doesn't fit anymore, then this episode is exactly what you need. Allie hands you a softer way of asking the question, and a few real ways of meeting yourself in the middle.

Mentioned by Allie:

1. The Awakened Brain
2. The feminine economy - sisters

Connect with Allie:

Check out Noria: my learning & development platform for a new era of living & leading

ASW

Connect with Maddie:

Dive into ⁠The Well on Substack⁠! Buy me a matcha!

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