When Envoy First Officer Alex Shupe welcomed passengers aboard his flight from La Crosse, Wisconsin (LSE) to Chicago, Illinois (ORD), it wasn’t just another day in the right seat—it was a full-circle moment decades in the making. Sitting in first class was his 88-year-old grandmother, Frances Dahlke, preparing for her very first flight. Before departure, Alex made a heartwarming pre-flight announcement, recognizing Frances along with his parents and brother who were all on board for this unforgettable experience — bringing three generations together in flight.
The heartwarming story captured national attention and was featured on ABC World News with David Muir, where viewers across the country shared in the emotional milestone: a farm-raised grandmother experiencing the wonder of flight for the first time, guided by the very grandson she had cheered on every step of the way.
A Family That Helped Him Soar
Aviation may be Alex’s career, but family has always been his foundation, and their support has never been in short supply. Alex’s mother, Merri, and grandmother Frances are both retired school teachers, instilling in him the value of discipline and lifelong learning. His father Doug, works in the marine business—an influence that led Alex to earn his Coast Guard Merchant Mariner License.
“My whole family has always been supportive of my aviation journey,” Alex says.
That support was especially meaningful from his grandmother. Grandma Frances never missed a milestone. Each new license and rating Alex earned came with a handwritten card in the mail and phone calls reminding him that he would achieve his goals. Those simple gestures became fuel during long study nights and demanding training flights.
So having her onboard with him at the controls was more than symbolic. It was deeply personal.
The Spark That Started It All
Interestingly, Alex didn’t always know he wanted to fly. Growing up, his family didn’t travel by air often. A trip to Disney World at age six was the extent of his early flying experiences. It wasn’t until he was 12 years old, on a family vacation to California, that something clicked.
The California trip sparked more than just Alex’s interest, it also rekindled something in his father. Doug had taken flight lessons in the 1980s but never fully pursued the dream. Now seeing his son’s fascination, he found ways to nurture it. Doug introduced him to Young Eagles flights through the local Experimental Aircraft Association (EAA) chapter, where Alex went on multiple free introductory flights with friends and siblings. Those experiences transformed his curiosity into commitment. In many ways, Alex is living out a goal his father once imagined. While Alex’s passion for flight became his own, Doug found fulfillment in a different way: watching his son soar.
A Steady Climb to the Flight Deck
Alex began formal training in 2018 at the La Crosse Colgan Air FBO, earning his private pilot license a year later. In the fall of 2019 he enrolled at the University of Dubuque in Iowa, where he continued building ratings under instructors who emphasized mastery—not just meeting check ride minimums.
Eventually, Alex became a flight instructor at the university, building flight time while mentoring the next generation of pilots. He credits that period as foundational to becoming a professional aviator.
Envoy Air had always been the goal. From the moment he learned about the Cadet Program at the University of Dubuque, he set his sights on joining.
“Envoy has been the only regional I wanted to work for,” said Alex. “The Cadet Program provided me with support and a direct path to the flight deck.”
Another reason Envoy stood out? The Chicago O’Hare (ORD) base.
“I wanted to be based in ORD because I knew they flew into LSE,” Alex said. “I knew I wanted to make this special family flight possible one day.”
From No Electricity to 30,000 Feet
Grandma Frances grew up on a farm without plumbing or electricity. Air travel wasn’t just a luxury, it was unimaginable. Yet there she was, at 88 years old, seated in first class, glowing with pride as her grandson helped guide the aircraft through the sky.
“She was just beside herself with joy the whole flight,” Alex recalls. “Having her and the rest of my family on board meant so much to me.”
She appreciated every detail—the professionalism of the crew, the hospitality onboard, and the experience at the LSE station. But more than anything, she appreciated the moment with her grandson.
The Art of Flying
For Alex, being an airline pilot isn’t just about schedules and destinations—it’s about the craft. He appreciates the flexibility the career demands and even welcomes the challenges when operations don’t go perfectly. While watching the world drift by from 30,000 feet has its moments, it’s the hands-on art of flying that he enjoys most.
“Being an airline pilot means you have to be very flexible and often times that is what I like most about the job,” said Alex. “It’s nice when things go smoothly, but you enjoy the challenge when things don’t.”
Advice for the Next Generation
Alex’s advice for other aspiring pilots? Trust the process.
“Don’t burn yourself out trying to rush through the training,” Alex advises. “you have a whole career to enjoy it.”
For Alex that patient approach paid off in ways no flight manual could have predicted–getting to welcome his 88-year-old grandma about her first flight, with him at the controls.