MILCOM Founders Podcast – Episode 56: First Female Little Bird Pilot to AI-Powered Homeownership with Lindsey Chrismon
Join host Rod Loges and guest Lindsey Chrismon as she traces a path from a childhood picnic at West Point to co-founding Oply, a venture-backed AI-powered home management platform built to give homeowners the kind of proactive guidance their cars already give them. Lindsey became the first and only woman in US Army history to fly the AH-6 Little Bird with the 160th Special Operations Aviation Regiment, flew Apaches at Fort Bliss before that, and served as West Point’s fourth female First Captain. She and her husband Gabe launched Oply out of Harvard’s Innovation Lab after Gabe’s restoration company revealed how many catastrophic home losses could have been prevented with basic, timely information.
In this episode:
- How an 11-year-old Lindsey attended a family picnic on West Point’s grounds and decided on the spot that it was the only school she would apply to
- What Branch Night looks like at West Point, how aviation slots are distributed based on order of merit, and the relief of opening an envelope with the right answer inside
- Flying the AH-64 Apache for three years at Fort Bliss before assessing for the 160th, and why the shift to training on the Lakota helicopter is creating real challenges for candidates who want to fly the Little Bird today
- Why leadership matters more in the civilian world than in the military, because the people following you can simply quit
- How Gabe’s water, fire, and mold restoration work revealed that roughly half of catastrophic home incidents could have been prevented if homeowners had known what to do and when
- The car dashboard analogy that drives Oply’s product logic and what a home-specific maintenance platform actually does
- Testing marketing messages for free through organic social media before spending money, and how millions of monthly views helped identify a winning content strategy to put budget behind
- Oply’s two-pronged go-to-market approach, direct to homeowners and through realtors, builders, inspectors, and mortgage companies
- Raising a $1.2 million pre-seed round led by Hivers and Strivers, and how a mentor’s dinner party led to a pitch in front of 13 Harvard deans and Bill Ackman, who invested
- The three things Lindsey’s mentor Reza Satchu says founders must demonstrate when fundraising: authenticity, inevitability, and momentum
- Why pitching investors whose thesis does not match your sector is a guaranteed no, and how recognizing that earlier would have saved significant time
- The current focus on improving 60 to 90 day user retention, and why a leaky funnel at that stage makes every marketing dollar spent on acquisition nearly worthless
- How Lindsey and Gabe keep work and marriage separate by using Slack for business and texting for personal communication
- Cooper’s difficult first 15 days in the NICU after inhaling meconium at birth, and how faith carried the family through that uncertainty
- The veteran-specific resources Lindsey recommends, including Warrior Rising, Hivers and Strivers, and the West Point Entrepreneurship Roadshow, which is open to all veteran founders
Key takeaways:
- “The Mom Test” principle applies: talk to as many homeowners, customers, or users as possible before you build. People who love you will tell you your idea is great, and that tells you nothing.
- Organic content is a free testing environment. Find what works before you spend money scaling it.
- Matching your pitch to an investor’s actual thesis is not optional. If their portfolio does not include your sector, no amount of polish will close the deal.
- You cannot fail if you do not quit, but that only holds if you are honest about what the data is telling you along the way.
- Retention is where growth strategies either prove out or fall apart. Acquiring users who do not come back is just an expensive way to empty a bucket.
- If you are not the kind of person who can find something worth showing up for in the hard middle of building a company, the outcome you are aiming for will not be enough to keep you moving toward it.
- The veteran network is not just a nice-to-have. It can be the lead investor in your pre-seed round, the room where you meet your biggest check writer, and the community that keeps you from feeling like you are building alone.
- When co-founders are also spouses, keeping work disagreements data-driven and free of spousal emotion is not a soft skill. It is an operational necessity.
Guest: Lindsey Chrismon, Co-Founder and CEO of Oply, West Point graduate and the Academy’s fourth female First Captain, Army Apache pilot, and the first and only woman in US Army history to fly the AH-6 Little Bird with the 160th Special Operations Aviation Regiment. MBA from Harvard Business School, where she launched Oply out of the Harvard Innovation Lab. Named to the Inc. Female Founders 500.
- LinkedIn: https://www.linkedin.com/in/lindsey-danilack-chrismon/
- Website: https://www.oply.app/
Lindsey Chrismon is the co-founder and CEO of Oply, a venture-backed AI-powered home management platform built to take the guesswork out of homeownership. Through a proactive, recommendation-driven model, Oply helps US homeowners stay ahead of maintenance and decisions rather than scrambling to react to them. She leads the company alongside her husband and co-founder, Gabe Chrismon, who serves as COO.
Before founding Oply, Lindsey graduated from West Point, where she served as the Academy’s fourth female First Captain, its highest-ranking cadet position. She went on to become the first and only woman in US Army history to fly the AH-6 Little Bird with the 160th Special Operations Aviation Regiment, one of the most demanding assignments in Army aviation. She earned her MBA from Harvard Business School, where she launched Oply out of Harvard’s Innovation Lab. Her work as a founder has been recognized on the Inc. Female Founders 500, and she is a frequent speaker at events including AHEAD’s Women in Tech conference and the West Point Athena Summit.
Looking ahead: Oply is focused on strengthening 60 to 90 day user retention while expanding its B2B2C partnerships with realtors, builders, inspection companies, and mortgage companies to reach homeowners at key moments in the ownership cycle.
The MilCom Founders Podcast champions and celebrates military community business founders. Each episode brings practical insights from successful veteran entrepreneurs.
Sponsored by One Degree Financial www.onedegreefinancial.com
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