TL;DR
Oply CEO Lindsey Chrismon was featured in the August 2026 edition of the Empower newsletter, a publication for entrepreneurs and business operators. She shared the full arc of how Oply came to exist, her path from West Point to special operations aviation to Harvard Business School, the investors who believed early, and what she is most focused on right now as Oply scales.
Read the full Empower feature here: Four Numbers to Put Your Strategic Planning on Track — Edition 069
The path that made Oply inevitable
Lindsey Chrismon did not build Oply by accident. Every part of her background was load-bearing.
West Point taught her to lead under pressure and trust her own judgment when the stakes are high. Then came the 160th Special Operations Aviation Regiment — the Night Stalkers — flying Little Birds in one of the most demanding aviation units in the world.
"Flying Little Birds with the 160th SOAR taught me that the people who get things done are the ones willing to do the hard thing first and figure it out as they go," Chrismon told Empower.
After her service, she went to Harvard Business School, where the frameworks caught up to the instincts she had already built. Then came the Harvard Innovation Lab, where Oply was launched.
"By the time we launched out of the i-lab, building Oply did not feel like a leap. It felt like the natural next mission."
The through-line was not always obvious in the moment. But looking back, it is unmistakable. A leader forged by West Point and the 160th SOAR, shaped by her husband Gabe's operational background in home restoration and a lived understanding of where the home services industry was broken, equipped with the tools from Harvard to translate all of it into a company. Oply did not emerge from a market gap analysis. It emerged from an accumulation of experience that made the problem impossible to ignore.
The investors who believed early
When you start a company, Chrismon noted, you brace for doors closing. What surprised her was which doors opened.
"We have Bill Ackman on our cap table, who is famously selective about where he puts his name and his capital. The Kraft Family, the owners of the New England Patriots, also believed in us early. These are not investors who write checks lightly, and having both on the same cap table still feels surreal some days."
She has also had the chance to pitch Kevin O'Leary, and Reese Witherspoon has personally mentored her through some of the most pivotal moments of building Oply.
These are not names that appear on cap tables by accident. They appear when the founder is credible, the problem is real, and the execution is showing up.
The scaling challenge Oply is inside right now
Chrismon did not offer a polished version of where things stand. She offered the honest one.
"We are actually right in the middle of our first real scaling challenge. We spent the early days proving that homeowners genuinely want what we are building, and the organic traction we saw earlier this year told us the product was resonating. The challenge now is moving from organic momentum to a real growth engine, and doing it fast."
Several things are converging at once. Oply just hired its first Lead of Consumer Growth. Late-stage conversations are underway with a major warranty company whose incentives align closely with Oply's, which would unlock distribution at a scale that is difficult to replicate. And the team is getting the operational foundation in place ahead of a Series A.
"The way we are overcoming it is the way we have overcome everything so far: hire people who are better than us in their lane, make sharp decisions with the information we have, and stay close to the customer so we never lose the thread of why we exist."
The next chapter, as she frames it, is about scaling without losing the soul of what made the early product work.
What she would tell herself at the start
The Empower interview asked Chrismon what advice she would give herself if she were starting over. Her answer was direct.
"Be bold. Get rid of the impostor syndrome early because it will cost you more time and more opportunities than any actual mistake ever will. Trust your judgment. Your gut is usually right, and the moments I have second-guessed mine are almost always the moments I wish I had moved faster."
On hiring: "Do not get seduced by shiny resumes. The pedigree on paper rarely correlates with the grit you actually need in a startup. The best people I have hired are the ones who run toward hard problems, not the ones with the most impressive logos behind them."
And the line every founder hears but almost no one actually follows: "Hire slow, fire fast. The cost of holding on to the wrong person is always higher than the discomfort of making the change. Protect the team you are building, because in the early days, the team is the company."
What Oply is built for
Oply is an AI-powered home maintenance platform that takes the guesswork out of home maintenance — helping homeowners track their home's history, set recurring maintenance reminders, save trusted service professionals, and build a digital maintenance record that compounds in value over time.
The home is the only major asset that comes with no operating manual. Oply is the platform that gives it one.
As Lindsey put it to the Empower community: "I want the good feedback and the bad feedback, especially the bad. Every honest piece of input makes the product sharper and gets us closer to the home management experience homeowners actually deserve."
One ask
Lindsey made a direct ask to the Empower community: download Oply, try it, and if you love it, leave a five-star review in the app store. Then share it with a neighbor, a family member, the friend who is always texting about a contractor they cannot get to call them back.
We second that ask.
Download Oply from the App Store or Google Play. Give it your house. Tell us what you think.
