#35 - Lindsey Christmon - The First Woman In U.S. Army History To Pilot The AH-6M Little Bird

Lindsey Chrismon is a U.S. Army veteran, pioneering aviator, Harvard Business School graduate, and tech entrepreneur known for breaking barriers and pursuing relentless excellence.Born in Montville, New Jersey, into a non-military family, Chrismon grew up as a self-described "tomboy," building tree forts, riding bikes, and excelling in sports from a young age. She competed in soccer, basketball, track, and even played drumline in her high school marching band. Entering West Point in 2010, Chrismon endured the grueling Cadet Basic Training ("Beast"), where blistered feet and self-doubt tested her resolve, but she persevered. As a cadet, she balanced rigorous academics, military training, and athletics, captaining the women's track team in events like the 400-meter hurdles, pentathlon, and heptathlon. She led the Black Knights to their first victory over Navy in track since 2007. Her leadership culminated in 2013–2014 when she was selected as First Captain of the Corps of Cadets—the highest cadet rank, responsible for leading all 4,400 cadets—making her only the fourth woman in West Point's history to hold this position and ranking her No. 1 in her class.Graduating in 2014 with a bachelor's degree in American Government and Politics, Chrismon commissioned as an Army Aviation officer. Her first assignment was flying the AH-64 Apache attack helicopter with the 3-6 Cavalry Regiment at Fort Bliss, Texas, where she served as a platoon leader for four years. Seeking greater challenges, she applied to the elite 160th Special Operations Aviation Regiment (SOAR), known as the "Night Stalkers." After a rigorous assessment in 2018, she became the first woman in U.S. Army history to pilot the AH-6M Little Bird—a lightweight, highly maneuverable attack and assault helicopter used in high-stakes special operations. She flew missions requiring precision low-altitude flying, stealth, and multitasking, earning respect through her skill and leadership. Chrismon served nearly a decade in the Army, transitioning out in fall 2023.While at West Point, Chrismon met fellow cadet Gabe Chrismon (Class of 2014), a former Infantry officer; the couple later married and became business partners. Post-military, Chrismon pursued her long-held goal of attending Harvard Business School—she had written in her West Point yearbook a decade earlier that she wanted an HBS MBA. Accepted into the Class of 2025, she graduated in May 2025 with her MBA, focusing on entrepreneurship and technology. During her time at HBS, she co-founded Oply, an AI-powered home management platform that helps homeowners predict, manage, and automate maintenance to protect and increase property value. As co-founder and CEO, Chrismon leads the Nashville-based, venture-backed startup alongside her husband Gabe (COO). Drawing from their military discipline and prior experience in home services, Oply applies proactive principles—similar to aircraft maintenance—to revolutionize homeownership for busy families. Chrismon is also a Veteran Fellow (2025–2026) at the Hoover Institution, advocating for responsible AI governance.Please leave us a review on Apple/Spotify Podcasts:Apple - https://podcasts.apple.com/us/podcast/the-kagan-dunlap-show/id1734065968Spotify - https://open.spotify.com/show/4CoB0WzZTGwZHj7LJIZDTI?si=3f85eb09f07249e7Kagan Dunlap Show Links:Website - https://kagandunlapshow.com/X - https://x.com/KaganDunlapShowInstagram - https://www.instagram.com/kagandunlapshow/TikTok - https://www.tiktok.com/@kagan.dunlap.show?lang=enFacebook - https://www.facebook.com/profile.php?id=61583743284059Lindsey Chrismon Links:Instagram - https://www.instagram.com/lindsey.chrismon/?hl=enFacebook - https://www.facebook.com/lindsey.danilackLinkedIn - https://www.linkedin.com/in/lindsey-danilack-chrismon/X - https://x.com/lindseychrismon