In this episode of the Milpreneur Podcast, host Ryan Van Ornum sits down with Lindsey Chrismon, a powerhouse veteran entrepreneur with a resume that reads like fiction. From being the First Captain at West Point and the first female AH-6 Little Bird pilot in the 160th SOAR to graduating from Harvard Business School, Lindsey is now tackling her biggest challenge yet: the tech startup world. She is the co-founder of Oply, an AI-driven PropTech company designed to revolutionize how homeowners manage maintenance.

Lindsey opens up about the massive transitions in her life, moving from the cockpit of elite helicopters to the classrooms of HBS, and dealing with the imposter syndrome that came with it. She shares her brutally honest take on resilience, explaining why "success" is just the result of refusing to quit after failing 100 times. The conversation dives deep into her leadership philosophy—specifically the "Buy Cleats" mentality—and how she is applying military precision to scale Oply into the ultimate home management system.

In this episode, you will learn:

• The 3 non-negotiable leadership principles Lindsey learned from her military commanders.

• How to leverage the "Buy Cleats" mindset to show up prepared for any business challenge.

• Strategies for overcoming imposter syndrome when entering high-performance environments like HBS.

• How Oply is using AI to predict maintenance needs and automate home service bookings.

• Why resilience and the willingness to fail are the most critical traits for a startup founder.

About Lindsey Chrismon:

Lindsey Chrismon is a West Point graduate, former 160th SOAR helicopter pilot, and Harvard Business School alumna. She is the co-founder of Oply, a company dedicated to simplifying homeownership through intelligent, AI-powered home management and service automation.

Connect with Lindsey Chrismon & Cynergists:

Oply Website: http://oply.app

Sponsor: The sponsor is Cynergists: http://www.cynergists.com

If you enjoyed Lindsey's journey from the cockpit to the boardroom, be sure to subscribe, leave a review, and check out Oply to streamline your home maintenance today!

#Milpreneur #VeteranBusiness #Oply #PropTech #WomenInTech #LittleBirdPilot #WestPoint #HarvardBusinessSchool #Entrepreneurship #leadership

Chapters:

00:00 - Introduction & Sponsor

00:55 - West Point, Track & Field, and First Captain

01:55 - Aviation Career: From Apaches to the 160th SOAR (Little Birds)

03:15 - Transitioning to Harvard Business School & Imposter Syndrome

04:41 - The Role of Failure in Building Resilience

07:05 - The 3 Principles of Leadership: Be a Good Dude, Figure it Out, Buy Cleats

09:47 - The Origin of Oply: Solving the Homeowner's Nightmare

11:00 - How Oply Uses AI to Automate Home Maintenance

14:05 - The Vision: Becoming the "Instacart" for Home Services

15:43 - Rapid Fire: Podcasts, Superpowers, and Cheat Meals

17:28 - Closing & Call to Action