Anything But Typical

Gary Frey & Ben McDonald

Gary Frey & Ben McDonald host round table conversations discussing entrepreneurship, leadership, and success on your own terms.

  1. 1D AGO

    162: Behavioral Performance In Business with Cathy Maday

    “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.”

    1h 15m
  2. 12/02/2025

    157: Solving The Ugly Problems Nobody Wants with Kenneth Lopez

    “I like to solve problems, & I never give up.” – Martin Kenneth Lopez Most founders talk tough. Kenneth grew up in a place that required it. Lima, Peru — beautiful on the surface, unforgiving underneath. Corruption. Precarity. An environment built to break entrepreneurs. There’s no help desk in a place like that. You either solve problems… or you get swallowed. That wiring became his operating system. So, when he launched his first company in his early 20s, he didn’t seek the easy path — he sought a bigger arena. “Forget local,” he said. “I’m building for the U.S.” No connections. No warm introductions. Just hunger, a laptop, & LinkedIn. And his pitch wasn’t polite — it was legendary: “Give me the project nobody wants. The ugly, neglected, impossible one. If I don’t deliver, you don’t pay me.” All the risk on him. All the upside for them. That’s how a kid from Lima ended up solving Perl script nightmares for Bank of America… & earning a reputation as the one-man A-team you call when everyone else slinks away. Today at Equals 11, the stakes are higher — Salesforce chaos, global teams, stalled initiatives — but Kenneth’s ethos hasn’t budged: Run toward the hard. De-risk it for the client. Solve — don’t whine. If you’re the kind of person who gets stronger when the work gets messy, this episode is for you. Connect with him through Equals 11. Kenneth doesn’t quote Churchill — he proves him right: “Difficulties mastered are opportunities won.”

    52 min
5
out of 5
21 Ratings

About

Gary Frey & Ben McDonald host round table conversations discussing entrepreneurship, leadership, and success on your own terms.