Second Life: The Sixty-Year Startup of Kenai Aviation

The Kenai Aviation purchase agreement basically consisted of the small airline’s good reputation and one six-seater, single-engine aircraft.

“It was a big deal to us, to be able to save that local business and carry on its legacy,” Jacob says. “It really was a startup because it had gone down to almost nothing, and we’ve built it back up again. It’s like, yes, we’re a sixty-plus-year-old business, but we’re also kind of a new business. It’s a little of both.”

Flexible Schedules

The Caldwells went to work realizing their dream of providing scheduled community air service, by Alaskans for Alaskans, with the addition of a nine-passenger, twin turboprop airplane in March 2020, with the intent of a second to follow. The same month, the COVID-19 pandemic shut down travel.

“It was really an up and down adventure getting through 2020 and the COVID era. We buy big expensive business stuff and then get handed that,” says Jacob. The Caldwells pivoted from scheduled commuter service to on-demand charters, primarily serving the commercial fishing industry. Having limped through the pandemic, the company added three nine-seat Tecnam P2012 Travellers within the next three years and returned to the original business model.

In addition to providing a scheduled community service so anyone can get to town whenever needed, a small airline also needs to support industry and businesses by providing charters.

One example that stands out for Joel is the day Kenai Aviation got a call from a commercial fishing company with a boat idled for maintenance in Saint Paul in the Pribilof Islands, with a price tag of $15,000 a day. The needed part was in Sand Point, almost 400 air miles away—and almost 500 miles from Kenai. The phone call came in: “Is there any way you can pick up this part and get it to us? And oh, by the way, we need it by the end of the day.”

“Because we had that ability to be flexible, my son called me at home on a Sunday, and we made it happen,” Joel recalls. “With scheduled service, that means the person who bags your groceries at Safeway needs to fly up to Anchorage for a doctor’s appointment or whatever else, but they’re not the kind of people who will ever be able to afford a charter. Both are needed, so we focus on making sure we stay strong on both sides.”

Survival of the Fittest

The commuter airline market is often red in tooth and claw. The Kenai Peninsula has been especially competitive in the last few years.

Grant Aviation and Ravn Alaska were already serving the Kenai Municipal Airport when Kenai Aviation began flights between Kenai and Anchorage in 2022. Seeing Homer was only served by Ravn Alaska, the Caldwells added that destination to their schedule. Then Aleutian Airways started up and, in 2023, began service to Homer with fifty-passenger airliners in competition with Ravn’s thirty-seaters, ushering in a contentious airfare war. Kenai Aviation pulled out of Homer to concentrate on daily flights to Anchorage. Then, in a surprise move, Ravn announced in November 2023 it was pulling out of Kenai.

It was a windfall for Kenai Aviation. “We went from, literally in about two to three weeks, hauling about 600 passengers a month in the Kenai–Anchorage market to 3,700,” says Joel. “It forced us to accelerate and add a lot more flights and a lot more staffing and infrastructure. It was a lot of growth really quick and a lot of overhead, so now we’re just having to grow markets to increase revenue to be able to cover that overhead.”

Opportunities continued to surface. In addition to regular flights and charters in and out of Homer, Kenai Aviation began two flights a day between Anchorage and the Western Alaska village of Unalakleet at the end of April, following Ravn’s announcement to pull out of that market. The airline also recently received the contract for scheduled service between Anchorage and Seward that started May 1, a service long in coming.

A Family Affair

On the Kenai Aviation website, Joel’s biography tells all about his days flying humanitarian aid workers in the Russian Far East and rural Alaska villages and his current gig as captain on Alaska Airlines’ Boeing 737s. But it doesn’t say anything about the three-year-old boy who flew toy cars with his older brothers.

“My brothers would be upset because they would be building these little road systems on the carpet and I would fly mine,” Joel recalls. “They would say, ‘You can’t do that,’ and I said, ‘Mine can fly.’”

At the age of 16, with a $50 birthday check in hand, Joel drove his Pinto to a little airport in northern Wisconsin to find a flight instructor. It took most of the day, but he finally found an old guy working on an airplane and asked if anyone could give him a flight lesson. When asked if he had any money, he proudly produced the birthday check and asked if that was sufficient. “It is today,” said the old guy. “He got up, cleaned his hands off. We walked out and got into a 1956 Tri-Pacer, and I took my first flight lesson. It went from there,” Joel relates. Whenever his tip jar from waiting tables in the summer collected enough for another lesson, he drove his Pinto back to the little airport.

Son of a preacher, Joel began going on mission trips to Paraguay while still in high school, and he became captivated by a pilot who routinely landed his Cessna 206 on a little strip in the middle of the village to deliver supplies.

That was Joel’s introduction to the concept of a missionary pilot. After graduation, he did just that, but first he had to get his aviation mechanic’s license.

“They expect you to be dropped in the jungle somewhere while flying and maintaining your own airplane and taking care of people,” he adds.

At the age of 24, he moved his young family to Alaska in 1997 and began his aid worker flights out of the Kenai airport.

The rest is Caldwell family aviation history. Jacob, age 30, started working in the commercial aviation industry alongside his father when he was 15. His brother Caleb helped start Kenai Aviation’s flight school in response to a nationwide pilot shortage. He is now a first officer for Delta Airlines and a C-17 pilot in the Alaska Air National Guard. Younger sister Tacy joined the business as resource manager last year. And Joel and his wife Karin, who is a flight attendant for Alaska Airlines, continue to subsidize the growth of their airline whenever needed and apply what they learn from Alaska Airlines at their smaller company.

Unique Team

Joel credits their airline’s success to the diversity of its more than fifty employees.

“We’ve pulled together a team with so many different backgrounds,” he says. “We have professionals that come from small on-demand operations. We have leadership in our team from major airlines. We have leadership who come from military aviation.”

But Joel gives most of the credit to Evan Veal, Kenai Aviation’s director of operations. “He’s our secret sauce behind the scenes.” Joel says the head of an airline is, in an official sense, the director of operations, responsible for overall operational control of all flights as well as safety and compliance of the airline as the primary liaison with the FAA and other government entities.

Veal worked for the original founder of Kenai Aviation from 2009 to 2017 and returned to the airline last year to “work with the Caldwells’ newly expanded operations, helping to ensure the highest level of travel safety to our community as we continue to improve and expand our services,” says Veal.

“I’ve known Joel for most of my aviation career—I’ve even hired him as a pilot in the past—and I share his vision for serving the Kenai Peninsula and beyond,” Veal adds.

“Our goal above all is to do it safely,” Veal says, regarding Kenai Aviation’s operation. “With these attitudes and initiatives, we’ve positioned ourselves for unlimited growth and expansion without compromising safety.”