Meet O'Rourke — Artist-Turned-Advisor. Systems Thinker. Old-School Southern Rebel.
My path to financial education isn’t your typical one. I come from the worlds of color theory, alternative music/opera, and California art schools. Yet, somehow, I kept getting hired to manage other people’s budgets, books, and businesses. Turns out, I’m good at making numbers make sense — and even better at helping others take action on them.
I make a living offering practical CFO advising for small business owners who create with their hands and hearts — artists, designers, healers, stylists, tradespeople, builders…you get the idea.
But I don’t stop there. I believe financial freedom is both a spiritual and political act. This belief runs deep in my blood: my earliest known ancestor, Shandy Wesley Jones, was a freed slave who became an abolitionist. He used his business as a path to freedom — buying enslaved people in order to free them.
While I’ve never faced anything close to that level of hardship, I am deeply aware that many people today are still trapped in forms of modern-day oppression, some subtle, some overt. Authoritarianism takes many shapes, and while the tactics may look similar — manipulation, control, division — the systems today are not the same as those that enslaved millions. Our current battles may not involve literal chains, but they still involve systems of power that seek to control freedom of thought, action, and opportunity.
I wake up each day thinking about what freedom means in this context. For me, it’s about freedom of time, freedom of mind, and the kind of growing prosperity that will allow me to always own my creativity. That’s the kind of financial freedom I believe everyone deserves, and it’s what I’m working toward — both for myself and for the people I serve.
Why freedom of mind?
After leaving high-control groups, I’m acutely aware of how dogma and hierarchical thinking can trap us — including when it comes to money. That’s why I teach financial strategies free from shame, manipulation, or the false promises that many “gurus” use to control people.
I’ve served as Chief of Staff for nonprofits, managed estates for multigenerational families, trained school principals to manage multi-million-dollar budgets, and coached entrepreneurs to turn their big visions into profitable realities. I was also a million-dollar-per-year retail salesperson — and those numbers could have been higher, but I spent much of my time talking customers out of using financing and credit cards.
