What I Learned Teaching Finance in a Homeless Shelter

For five years, I sat across from people who’d lost everything – and learned exactly why it happened.

For five years I taught “Finance w/ Hillary,” a weekly financial literacy class in a local Cincinnati men’s homeless shelter. Men from every background imaginable: former athletes, CEOs, blue-collar professionals, individuals in recovery, men who couldn’t read or write as well as men who had master’s degrees all sat in my class together. This class enabled men to develop a solid financial foundation while giving them an opportunity to put these concepts into action before they transitioned back into everyday life. The class had to be taught in a way that met each man where he was, while simultaneously teaching to the group as a whole.

While at the shelter, I learned firsthand what happens when people don’t have the financial foundation they need to be successful. It saddened me to hear the stories that put the athletes in the shelter and after lengthy conversations we agreed with my class that the situation could have been prevented.

The pattern was always the same: they knew what they were supposed to do with money. They could explain budgets, debt, savings. But when it came to actually managing their money, something broke down. They didn’t understand why they kept making the same mistakes.

As a consultant, it was heartbreaking to listen to countless entrepreneurs tell me they lost everything because they dismissed themselves and their financial abilities by saying ‘I just wasn’t a money person’ and placed all money decisions in someone else’s hands. They handed over complete control to advisors, accountants, even business partners – people they trusted. And when those people failed them (or worse, stole from them), they had no foundation to even recognize what was happening.

And separate from finances, I’ve watched athletic dreams end suddenly with injury, both personally as a mom and professionally.

This is what I bring to every client I work with: the pattern recognition that comes from witnessing financial failure up close, and the foundation-building that prevents it. Whether you’re a college athlete with a sudden NIL deal, a TAP student learning to manage money for the first time, or an entrepreneur building a business – the foundation comes first.