155: Helping CEOs Move Beyond Hurdles to Scale with Shay Prosser

“Entrepreneurship is scary as well as compelling in a weird way.” – Shay Prosser That’s the quiet admission of someone who’s lived the tension of building something that matters—between fear & purpose, risk & reward—and kept moving anyway. Shay started in chaos: a newborn on the floor, the economy unraveling, & a business idea that couldn’t wait for permission. It wasn’t perfect timing; it was purpose knocking early. When her one-to-one financial coaching couldn’t reach enough people, she rebuilt the model—bringing financial education into workplaces & later onto military bases with the USO. That pivot became her pattern: find the gap, build the bridge. So when business owners began coming to her not just for answers but for direction, she created spaces to think differently—to set bold goals, make smart moves, & scale with clarity, courage, & connection. Today, she helps business owners do what she’s always done—move forward, even when the path isn’t clear. Not with ten-year dreams, but ninety-day wins. Progress, not perfection. Because growth doesn’t come from having it all together—it comes from showing up anyway. To learn more, connect with her through North 12 Partners or Birthing of Giants. Shay reminds us what Amelia Earhart said best: “The most effective way to do it is to do it.”