First Check Calls Game

Most people think they’re not qualified to make investment decisions. Cheryl Kellond thinks that’s exactly the problem. A 3x founder, 3x Ironman, 4x mom, and CEO of PlayMoney, Cheryl is on a mission to open up early-stage investing to the people who actually understand the problems worth solving. In this episode, she challenges the outdated model of capital allocation and makes the case that the real barrier isn’t money, expertise, or access. It’s a system built for a world that no longer exists.

At its core, this is a conversation about decision-making as a skill. Cheryl breaks down why small checks, consistent reps, and learning by doing matter more than waiting until you’re “ready.” She and Mack get into the math behind portfolio building, the reality that losses come before wins, and why the only thing that actually predicts success is how many decisions you make. If you’ve been sitting on the sidelines, consider this your push: first check calls game.