EPISODE · Nov 15, 2025 · 9 MIN
When Culture was the Moat: The Rise and Drift of Southwest Airlines
from Insights · host Keith Dorson
For nearly 45 years, Southwest Airlines defied gravity — not just in the skies but in business. Herb Kelleher built an airline where culture was the moat and people came first. After his passing, that magic began to fade. In this episode, Keith Dorson unpacks how a founder’s philosophy created decades of success — and what every entrepreneur, leader, and small business owner can learn about building a system and a culture that lasts.
What this episode covers
For nearly 45 years, Southwest Airlines defied gravity — not just in the skies but in business. Herb Kelleher built an airline where culture was the moat and people came first. After his passing, that magic began to fade. In this episode, Keith Dorson unpacks how a founder’s philosophy created decades of success — and what every entrepreneur, leader, and small business owner can learn about building a system and a culture that lasts.
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When Culture was the Moat: The Rise and Drift of Southwest Airlines
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