S02 E06: Andrew Tidwell, CHRO of Wineshipping

Meet Andrew Tidwell

Andrew Tidwell has never followed the traditional HR playbook. With a background in labor negotiations, international chaos, and what he calls “solving difficult people problems,” Andrew built a career by saying yes to the messy stuff—and figuring it out mid-flight. Today, he’s CHRO at WineShipping, where he’s helped transform a fast-scaling logistics company into a culture-first, award-winning workplace.

But ask him how he got there, and he’ll tell you: It wasn’t by being the smartest guy in the room. It was by being the most useful.

In this episode of Real Leadership, Andrew shares the moments that shaped his leadership style—from giving away a beat-up Jeep to settle a dispute in Mexico to building HR teams that operators actually trust.

In this episode, we cover:

• The myth of “don’t bring me problems” — and what to say instead
• The overlooked leadership skill that builds trust instantly
• Why HR needs to stop being “nice” and start being necessary
• How to coach when you’re the boss (and everyone’s guarded)
• The power of ownership—and how it rewires an entire company culture

Subscribe to Real Leadership on YouTube to keep up with the new episodes

Interested in being in Real Leadership? Join the conversation

Follow Real Leadership on LinkedIn

Listen on Apple Podcasts and Spotify

Follow Real Leadership on Instagram