Behind the Scenes of the 2025 Macy’s Day Parade - Logistics, Life Lessons & Doing What You’re Afraid To Do

Bill kicks off this episode by admitting he’s feeling overwhelmed—and sharing a relatable moment from the shower that many of us have absolutely been guilty of.

Then he welcomes a very special guest: Alex, a former intern from his morning radio days who has since become a television producer and a member of the Macy’s Day Parade team. Thanks to her, Bill and his son were granted rare, up-close access to all 18 balloons in the 2025 Macy’s Day Parade just one day before step-off.

Bill dives deep with Alex about what it really takes to pull off one of the most iconic live events in the world. From months of planning and tight coordination to street closures, utility teams, safety crews, balloon handlers, and NBC’s broadcast partnership—Alex breaks down the intricate logistics that make the parade run with precision year after year. You’ll even hear surprising bits of parade history as it approaches its 100th anniversary in 2026.

The conversation then shifts from giant balloons to giant life choices. Bill and Alex open up about pursuing opportunities even when you don’t know how you’re going to pull them off—taking inspiration from director James Cameron, whose CBS Sunday Morning interview Bill recently watched. They explore what it means to build something meaningful from where you are, whether it’s Alex’s next big career move or Bill’s journey through graduate school and growing a podcast company.

Bill gets personal, reflecting on the emotional weight he’s been carrying—from the passing of his father to the end of a long-term relationship and a newer one that fizzled out. He talks about the patterns he’s noticing in himself, the tendency to avoid feelings, and how “fun” can sometimes leave an unexpected emptiness.

Together, Bill and Alex dig into what real success requires. As Alex says, getting “beat up” by a job or a project can actually become your greatest teacher—and often leads you exactly where you want to go.

It’s an honest, insightful, and inspiring conversation between two people who are doing what they’ve always wanted to do, and doing it no matter what.

Enjoy.

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