How this Paratrooper Scaled a $90 Million Business

The High Achieving Female Podcast · Mar 19, 2026 · 1m

From jumping out of planes as an Army paratrooper to leading a $90 million business empire. Meet Deidre Windsor, our Season 8 finale guest! Deidre is the CEO of The Windsor Group and her story is a masterclass in the "Why not me?" mindset. After 22 years in the military, Deidre faced the "identity crisis" of transitioning to civilian life—but she didn't just survive; she thrived. In this episode, Deidre drops gems on: 🎖️ The Paratrooper Mindset: How military discipline builds 9-figure success. 📈 Scaling Fast: How she went from a $100k startup to nearly $90M in cumulative revenue. 👯‍♀️…