WASHINGTON — During one sweltering summer in upstate New York, Lindsey Danilack sat back in her barracks room, weary from a day of drills and cadences. She had spent hours carrying a 50-pound ruck in her first march.
In the opening days of the U.S. Military Academy’s “beast” or Cadet Basic Training, she pulled up the pant leg of her camouflage trousers and removed her boots to find her feet covered in blisters. Danilack, who had just begun her initiation into West Point in the summer of 2010, started to doubt herself.
“My feet were so ripped up.” said Danilack, now Lindsey Chrismon. “I was bleeding through my shoes.”
An accomplished track athlete who had competed in the Junior Olympics, she had never endured something as demanding as the six-week basic training, which prepares cadets for four years of military school. “I didn't understand where we were going or why we were marching in a line,” she said.
West Point was the only college she applied to, and she’d wanted to attend since age 11 years old, and although she privately questioned her decision at that moment, she remained committed to graduating, she said.
Even when the odds seemingly stacked against her, Chrismon welcomed challenges.
“She was the plebe that would stay up all night and clean her room and dust in between the floor cracks,” said fellow West Point alum and husband Gabe Chrismon. “Just her attention to detail is off the charts.”
Lindsey Chrismon’s reaction: try harder than everyone else. That attitude eventually propelled Chrismon to heights she could not imagine. Not only did Chrismon pass basic training, she quickly mastered balancing athletics and military duties during her plebe year at the academy. But she first had to overcome self-doubt.
“I would think to myself, wow, everyone else is so much better than me,” she said. “Everybody has done so much more. I'm a nobody here.”
Chrismon had gradually built herself into a leader her entire life.
At an institution that has bred some of the nation’s top decision makers, Chrismon stood out among her peers.
She captained West Point’s women’s track team, competing in the 400-meter hurdles, the pentathlon and the heptathlon. She helped lead the Black Knights to their first win over Navy since 2007.
Finally, Chrismon’s drive eventually led her to becoming the fourth woman to serve as First Captain of West Point’s Corps of Cadets for the 2013-2014 academic year, ranking at the top of her class. Thereafter, during her 10 years in the Army, she became an accomplished pilot in the AH-64 Apache and the first and only woman ever to pilot the AH-6 Little Bird for the 160th Special Operations Aviation Regiment. Eventually, her drive took her to the campus of Harvard University, where she launched a venture backed AI tech company, Oply.
In May, Chrismon graduated as part of Harvard Business School’s 2025 class. Earning a degree from an Ivy League school typified the career of Chrismon, who never shied from taking the toughest route to achieve her goals.
“I would say that she is driven to a challenge,” said Army Chief Warrant Officer 3 Steve Scott a fellow pilot at the 160th SOAR. “If there’s no challenge involved, she’s probably not going to be interested.”
Chrismon admitted she had struggled with self-worth her entire life. But that stems from the near impossible standards she set for herself.
A childhood pact
During one July day in upstate New York, 11-year-old Chrismon, her parents and brothers travelled to the USMA campus for a picnic. They sat at Trophy Point, a popular tourist spot nestled between West Point’s rolling hills. On one end, onlookers can gaze upon the entire USMA campus and in the other: a picturesque view overlooking the winding Hudson River.
There, enamored by the military display of new cadets performing combatives, Chrismon decided her future. “I just fell in love with the atmosphere,” she said.
The middle schooler surprised her parents when she told them she wanted to attend West Point. Born into a non-military family, she had always focused on schoolwork and enjoyed studying. But most of her family never considered joining the military.
Chrismon said she grew up a “tomboy,” spending her springs and summers riding her bike through Montville, a New Jersey suburb of 22,000, about 30 miles west of New York City. She, her brothers, and her best friends would build tree forts in a patch of woods near her family’s suburban two-story home.
Chrismon had always been headstrong, first dabbling in youth sports at age 5 and competed in soccer, basketball and track in high school. She enjoyed playing on the drumline for her high school marching band. But she remained focused on the U.S. Military Academy throughout her high school years. She did not apply to any other college besides West Point.
In the fall of 2009, Chrismon received her LOA as a recruit for the West Point track and field team.
Although Chrismon suffered from what she called “imposter’s syndrome” at West Point, Gabe, her now husband, saw something different.
“Chrismon’s a natural leader,” said Gabe, Gabe said Chrismon continuously pushes herself to higher standards., while feeling unworthy internally.
At one point during her four years at the Academy, she said she learned to step back and pace herself. Her roommate and Gabe helped her realize she didn’t have to be the best at everything to succeed at West Point.
Chrismon said that this built her self-confidence.
Gabe met Chrismon on the campus. He invited her to attend one of his rugby games and the pair hit it off and began dating during their junior year.
Heading into her senior year, Chrismon didn’t plan on applying for a senior leadership position. She wanted to focus on academics, being the captain of the women’s track team, and her Army career, but her Tactical NCO convinced her to apply otherwise. This landed Chrismon in the most prestigious summer leadership position as the “King of Beast,” where she then led the 1,000 incoming New Cadets of the Class of 2017.
A milestone reached
The summer before their senior years at the Academy, after Chrismon had completed her leadership detail at Beast training, Gabe and Lindsey took a road trip through one of North Carolina’s desolate country roads during a visit to Gabe’s home state.
Chrismon’s cell phone rang. She heard the voice of West Point Commandant, then- Brig. Gen. Richard Clarke. After speaking with Clarke for a few minutes, she grabbed the steering wheel and let out celebratory yell, causing Gabe’s vehicle to veer to side of the road.
Clarke informed Chrismon that West Point had named Chrismon as its First Captain for the 2013-2014 academic year, the fourth woman in West Point history to ever hold this title.
“Congratulations,” Gabe said to his now wife with smirk. “But you almost killed us.”
Her husband said Chrismon has a distinct sincere approach to rallying others to her cause or her side. She maintains eye contact and speaks to every person the same way whether a four-star general or a neighbor down the street.
As First Captain, she once again privately struggled with the challenge, but soon learned that maintaining good relationships with fellow cadets led to success. She leaned on the knowledge she learned on dividing roles and responsibilities during her summer as “king” or leader of beast training.
“There's no guidelines for being the first captain,” she said. “You just kind of have to go with the flow and figure it out as you go.
“It's all about peer leadership, right? Because ... you have to be the face of the entire Corps of Cadets as the First Captain, but you're still the same as every other cadet in your class.”
“So, there's this fine line, this fine balance that you have to find as the First Captain that allows you to maintain your friendships and your relationships but also be a force of nature for the entire Corps.”
In May 2014, more than 1,000 cadets poured into West Point’s Michie Stadium for their graduation and commencement.
Just before she performed the traditional dismissal of the Class of 2014 as First Captain, she extended her white gloved hand to greet President Obama who gave the commencement address.
Joining the Army’s best
Moving from one milestone to the next characterized Chrismon’s decade in the Army. In her first assignment at Fort Bliss Texas, Chrismon flew possibly the U.S. military’s most lethal attack helicopter, the AH-64 Apache. She had circled aviation as her only career choice early in her years at West Point.
“I remember looking out the window of my barracks at West Point and I saw an Apache come and land,” she said. “I went out and I just looked at that beast of an aircraft and I was like, holy … that's what I want to do in the Army.”
After four years flying the Apache, Chrismon wanted to take on an assignment that would test her abilities further.
She had always admired the capabilities of the AH-6 Little Bird and the difficult stealth operations the Army uses the aircraft for in the 160th Special Operations Aviation Regiment.
No woman had ever successfully assessed to fly the AH-6 Little Bird, so attempting to do so and failing could hurt her career.
The doubt and challenge only fueled her ambitions, but, overall, it was not about the challenge, it was about the mission set. Chrismon wanted to continue to serve her country in the most elite helicopter force on the planet.
She applied for a slot to assess as an AH-6 Little Bird pilot. Engineers designed the AH-6, a light attack helicopter to deliver precision fire support during special operations missions.
Little Bird pilots are comprised of some of the most elite, experienced rotary wing aviators in the Army.
Qualifying to fly the air frame posed a difficult hurdle for even veteran pilots.
Chrismon said when loaded with rockets, minigun ammo, and fuel, the airframe can be challenging to maneuver requiring the pilot to multitask on a graduate level.
“There's no hydraulics and it's very power limited,” she said. “So, your power margin is very, very slim … you're flying in a very aggressive profile where you're aiming the aircraft at the target. This aircraft doesn't have articulating pylons like the Apache does; everything is fixed.”
Chrismon said the aircraft requires pilots to manually maneuver into a unique attack profile while simultaneously firing to engage targets. Little Bird missions also demand flying at extremely low altitudes, even on the darkest nights, requiring precision, speed, and total focus to execute complex attacks.
After a demanding, week-long assessment, and months of OGP training, Chrismon became the first female in Army history to fly the AH-6 Little Bird and quickly earned the respect of veteran pilots in the 160th.
As a new member of the 160th Special Operations Aviation Regiment, she moved to Fort Campbell, Kentucky which sits on the Kentucky-Tennessee state line, 60 miles north of Nashville.
“She came through with flying colors and then really hit the ground running,” Scott said. “I'm not going to mince words, but it's not unique to males or females coming through … Some pilots are just stronger.”
She had a talent for selling ideas to others, as a cadet and Soldier. Scott recalled how during one training exercise, Chrismon’s assault force coordinated an attack with a simulated ground force. Scott said Chrismon convinced the ground force to successfully try a specific maneuver to test the capabilities of the aircraft.
“She has a very, very strange ability to get people on her side, you know?” Gabe said. “I don't really know how else to put that, and I think she does it from just being the hardest working person in the room.”
“She's usually the most knowledgeable person in the room. If she's not, she's the most humble person in the room. She's always willing to take criticism. She's always willing to learn from other people.”
Her husband, Gabe, had completed a nine-month deployment in Afghanistan as a Platoon Leader working alongside the Afghan Army.
He enjoyed most being in the trenches with fellow Soldiers. He knew as he rose through the ranks he would be taking jobs of higher responsibility, and less hours in the field. So, he left active duty to start his first business in the home services industry.
“We sacrificed a ton,” Gabe said. “You know, we were on one salary. And we were making less money than we had ever made together, her being on active duty and me starting a business. But that was something she did for me so I could start the business.” Three years later, Chrismon also decided to separate from the Army.
Again, she challenged herself -- she applied to seven schools (Chicago Booth, Kellogg, the Massachusetts Institute of Technology, Yale, Wharton, Columbia, and Harvard) and, earned acceptance into all seven. Chrismon had one target school on her radar and that was Harvard.
That renowned Ivy League school which graduated eight U.S. presidents, Nobel prize winners and leading scientists throughout history. The oldest academic institution in the United States, lined with 19th century buildings of crimson brick, and bountiful gardens.
She received her acceptance letter from Harvard to matriculate in the fall of 2023.
Chrismon admitted the atmosphere and resumes of her peers intimidated her. Harvard marked the first time she had attended a solely academic institution since high school.
“Coming into this new environment, I'm a bit older than everybody else and I have very little business background,” she said.
“So, my background was very different than my investment banker or consultant classmates. And so of course I felt intimidated by the … intellectual aperture of my classmates. But I fully recognized that the value that I brought to Harvard was very, very different and important.”
During her first semester, her and Gabe sold the Nashville-based restoration company and started a tech company, Oply. Oply uses AI to manage your home. Chrismon believes that soon, AI agents will monitor all aspects of a home (from the lifespan of the major systems, to the risks associated with deferred maintenance, to simple reminders on what and when to do something) allowing the homeowner to be the decision maker. They have built that future.
The Chrismons and their team designed Oply to make owning a home as simple as ordering an Uber ride, all while protecting homeowners’ most valuable assets. The Chrismon’s raised two rounds of funding led by Boston Seed and Hivers and Strivers, to make Oply a venture-backed business. They also secured additional investment from well-known investors such as Bill Ackman and the Kraft family.
Two years later, Chrismon graduated with second-year honors at one of the nation’s top academic institutions.
She split time running Oply long distance, travelling from Boston to her business in Nashville. As a track athlete, Chrismon distanced herself from the rest of the pack, outpacing the next runner by wide distance. Like she did on the running track, Chrismon stood out at every level in her military career and at the Ivy League School.
Now as a 33-year-old CEO of the venture backed tech startup Oply, Chrismon continues to serve her country, this time, in slightly different capacity – protecting fellow homeowners from the stresses of managing their homes.
In her 2025 dossier as a member of the HBS Class of 2025, Chrismon wrote “I refuse to live an uninteresting life; I will always seek adventure and challenges.”
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