💥 About Gwynne

I’m Gwynne Rukenbrod Smith, and I’ve worn a lot of hats: nonprofit exec, arts leader, business coach, curator, board chair, and now unapologetic financial rebel. I’ve led multimillion-dollar organizations, built national entrepreneurship programs, and coached hundreds of badass founders and creatives to turn their vision into sustainable, scalable reality.

But long before all that, I was just a punk kid in the ‘80s, boots on, middle finger up, and a fire in my chest that said there’s got to be a better way. That fire? Still burning.

Punk taught me to question everything. To never blindly follow. To call out the system when it’s broken and build something better when no one else will. That same rebel spirit drives everything I do at Boss Grrrl Financial. I’m not here to fit in. I’m here to shake things up and help others do the same with their businesses, their money, and their mindset.

With decades of experience in leadership, fundraising, strategy, and financial planning, I founded Boss Grrrl Financial to do things differently. To cut through the jargon. To stop the gatekeeping. And to help entrepreneurs, especially those from creative and underestimated communities, get clear, get confident, and get paid.

I bring all of me into this work: the strategist, the maker, the truth-teller, the rebel, the mentor. And I’m not afraid to say what others won’t—because playing nice doesn’t build powerful businesses. But clarity, strategy, and fierce support? That absolutely does.

Here’s the truth: even with an MBA, years of nonprofit leadership, and all the credentials, I still struggled with money. Not the math. Not the spreadsheets. The feelings. The fear. The shame. The “ick” of talking about money, especially as a woman, especially in the nonprofit world.

As an Executive Director, I had to push through all that. Fundraising. Budgeting. Payroll. I had to learn how to stop avoiding, start leading, and own my financial power. It wasn’t easy, but it changed everything.

And I see it every damn day in the small business owners I coach. Brilliant people held back by fear, confusion, or silence around money. It’s not their fault. Our society sets us up for this with no financial education in school, no space to examine our money stories, and no support to rewrite them.

Well, f*ck that. It’s time we take our power back.
It’s time we talk about money. Learn how it works.
Unlearn what’s holding us back. And build businesses that don’t just survive, but thrive.

That’s what Boss Grrrl Financial is here for.