“I’ve been poor before. That doesn’t bother me.” – Cathy Maday Cathy didn’t grow up around startup jargon or leadership books. She grew up on the Bad River Indian Reservation in northern Wisconsin. Work wasn’t a phase. It was how you made things possible. You did chores, took odd jobs, & learned early that no one was coming to rescue you. There was freedom in that. By 12, Cathy was holding her first paper paycheck. She hasn’t stopped working since — not always because she had to, but because work meant agency. Motion. A steady sense of “I can handle what’s next.” That assurance followed her from childhood into college, into technology, & into corporate environments where she saw it clearly: systems weren’t failing. The people inside them were carrying too much, alone. Eventually, Cathy did what entrepreneurs do. She chose the harder path & built the solution — Wingspan — from the same instinct that had always guided her: if you want options, you create them. This episode isn’t about hustle or reinvention. It’s about knowing when the instincts that made you strong are asking for something completely new. To learn more, connect with her at WingspanPerformance.com. Entrepreneurship isn’t about escaping where you come from. It’s about carrying what made you — and knowing what to set down. As Wendell Berry wrote, “It may be that when we no longer know what to do, we have come to our real work.”

“I closed the biggest deal of my life playing Candy Crush on my phone over Zoom… I could do this in my sleep at this point.” — Lauren Goodell One moment, Lauren Goodell was operating at the highest level — thriving in corporate tech, leading the room, closing deals most people never touch. And then, something became clear. The work wasn’t hard anymore. The risk was gone. The challenge had faded. What once demanded everything she had now required very little. In that moment, her future shifted. Not because she failed — but because she succeeded. And she knew that mastery without growth is just another form of standing still. So, she walked away. What followed wasn’t instant clarity. It was friction. Failure. Momentum earned the hard way. Today, Lauren is building technology that handles the prep work she got bored of — so people can focus on the conversations that actually matter. That moment — the quiet realization — is where her story really begins. Connect with her on LinkedIn & learn more at getZinnia.ai Success doesn’t always signal arrival. Sometimes, it’s the cue to begin again. Anaïs Nin said it best: “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.”