2 days ago

Andrew Tidwell, CHRO of Wineshipping

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

Time Stamps

06:53 – The Mexico City Jeep story: creative problem-solving in action
 11:42 – HR as a driver, not a speed bump
 14:20 – Speaking finance: how HR wins credibility in the boardroom
 16:30 – The coaching haiku that changed Andrew’s leadership
 21:22 – “It’s not your sandbox—it’s our sandbox”: the case for ownership
 26:15 – What AI and robotics can’t replace in warehouse work
 32:17 – Habits that help HR leaders scale with the business
 34:54 – The problem with passing the message up the chain
 36:26 – Who WineShipping is hiring—and what kind of talent fits

Show Notes

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