Ep. 158 From Apache Pilot to AI Founder: Lindsey Chrismon on Leadership, Risk, and Entrepreneurship

In this episode of TheMilVet Podcast, host Beau Higgins sits down with Lindsey Chrismon, co-founder and CEO of Oply, former U.S. Army aviation officer, AH-64 Apache pilot, and the first woman in U.S. Army history to fly the AH-6 Little Bird in the 160th Special Operations Aviation Regiment (Airborne). A graduate of the United States Military Academy at West Point and Harvard Business School, Lindsey shares her journey from an 11-year-old determined to attend West Point to becoming a venture-backed tech founder building in the AI space.

Lindsey reflects on the mentors who shaped her leadership style, the intensity of serving in the 160th SOAR, and the pivotal decision to transition from a high-performing military career into entrepreneurship. She speaks candidly about betting on herself, walking away from traditional post-MBA paths like consulting, and committing fully to building something from the ground up.

Throughout the conversation, Lindsey breaks down how she and her husband scaled their first company before launching Oply—an AI-powered home intelligence platform designed to help homeowners proactively manage, maintain, and protect their most valuable asset.

Listeners will gain insight into:

• What it takes to become a “first” in elite military organizations
 • The power of mentorship in accelerating performance and confidence
 • Making the stay-or-go decision at a critical military career inflection point
 • Why committing fully—without a backup plan—matters in entrepreneurship
 • The realities of raising venture capital and keeping a clean cap table
 • How failure as a founder can increase long-term earning potential
 • Building AI responsibly while navigating evolving policy and regulation
 • Translating special operations leadership into startup execution

Lindsey also discusses the importance of embracing risk, overcoming fear of failure, and staying mission-focused during uncertainty—whether in combat aviation or venture-backed startups. Her story is a testament to disciplined ambition, bold decision-making, and the belief that service is a foundation—not a ceiling.

Whether you’re considering entrepreneurship, navigating transition, or leading in high-stakes environments, this episode delivers practical insight and inspiration for veterans ready to build what’s next.

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#Veterans #Leadership #MilitaryTransition #Entrepreneurship #AI #WomenInDefense #SpecialOperations #StartupLife #Resilience #TheMilVetPodcast

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