Strategic planning for independent entrepreneurs

The problem

28.1 million independent entrepreneurs make decisions every day without a strategic foundation. Most planning tools hand you someone else’s playbook — telling you what to do without ever asking who you are.

The result: burnout, drift, and the quiet question every misaligned founder eventually asks — how did I get here?

The solution

Pyramid doesn’t apply frameworks to you. Through AI-guided conversation, it surfaces the values already driving your decisions — then closes the gap between those values and how you actually operate. Not a template. A container for what’s already there.

How it works

Pyramid begins where every business should: with Values, then Purpose. From there, the Chamber becomes your ongoing strategic planning space. Visioning arrives in V2, planned for 2027 — because in this work, you don’t imagine where you’re going until you know where you stand.

Pyramid is built on Claude by Anthropic.

The founder

Pyramid encodes 14 years of methodology from Holly Howard, who has guided 1,000+ entrepreneurs through her consulting practice Ask Holly How. She has taught entrepreneurship at RISD and Pratt Institute, and for the Berklee College of Music Alumni Association. What used to require years of one-on-one work is now available to anyone.