Leadership isn’t a playbook—it’s more like improv… but with real consequences. Jeff Reid learned that the hard way when he became a manager at 25 with zero roadmap and a team suddenly depending on him. Turns out, you don’t need all the answers—you just need the guts to bet on people, face uncomfortable truths, and figure it out as you go.

In this episode, Jeff shares what leadership actually looks like behind the scenes: navigating the chaos of the dot-com boom, making tough calls (including firing people), and realizing—sometimes too late—when it’s time to step in. We talk about missed signals, course corrections, and why “hoping it works out” is not a strategy.

We also get into what does work: balancing empathy with accountability, giving people not just space but fuel to grow, and having the conversations you’d really rather avoid. Because those? They’re usually the ones that matter most.

Bottom line: leadership is messy, humbling, and occasionally painful—but also where the real growth happens. So if you’ve ever wondered whether you’re doing it “right”… you’re not alone. And more importantly, it’s going to be okay.