The Story Behind Jolly Roger
A platform built for those who refuse to accept easy answers. For the ones who know that real growth requires confronting uncomfortable truths—about the world and about themselves.
Why This Exists
Jolly Roger started from a simple observation: most people are trapped in mental prisons of their own making. Not because they're stupid, but because the human mind is wired to seek comfort, belonging, and certainty—even at the cost of truth.
We pick teams, we defend positions, we build identities around beliefs that we never examined. And when reality conflicts with our worldview, we don't update our map—we deny the territory.
This platform exists for the small percentage who want something different. Who are willing to do the uncomfortable work of questioning everything. Who understand that evolution isn't just nice to have—it's survival.
The name comes from the pirate flag—a symbol of those who operated outside conventional rules. Not criminals, but people who refused to accept arbitrary limitations on how they could think and live.
To help people see reality more clearly and act on it more courageously.
Everything we create—every podcast, essay, workshop, and conversation—serves this single purpose. Not to tell you what to think, but to help you think better.
Truth Over Tribe
We prioritize what's real over what's comfortable. Loyalty to truth means being willing to question everything—including our own beliefs.
Evolve or Die
Adaptation isn't optional. The world changes, and those who cling to outdated maps will be left behind. Growth requires letting go.
Questions Over Answers
The quality of your questions determines the quality of your life. We cultivate curiosity and resist the false comfort of certainty.
Radical Honesty
We say what we mean and mean what we say. Uncomfortable truths serve growth; comfortable lies serve stagnation.
The Seed
Beggan my roofing business from the ground up.
Going Public
My business had grown to be the biggest roofing contractor in West Texas.
New Beginnings
Created the inner circle—a private community for those committed to doing the real work of evolution.
Speaking Circuit
Began keynoting at major conferences. Message resonated with leaders tired of surface-level thinking.
Scaling Impact
Crossed 1 million podcast downloads. Launched workshops and executive coaching programs.
The Platform
Expanded into a full platform—podcast, writings, events, and community all under one roof.