From curbside pickup to comfy fashions, the coronavirus pandemic has prompted many new trends. But ‘working from anywhere’? Its roots predate the arrival of COVID-19 by decades. My brother David and I know, because Tradewind Aviation helped get working from anywhere off the ground.

Dial back to 2001 and the start of Tradewind Aviation. At the time, people of means were already using private aviation to fly between vacation homes and offices. But to our eyes, they were not getting the value that we believed the industry could provide.

Then came 9/11. In the stressful weeks and months that followed, the simple act of flying commercial changed radically. As major airlines limited flights, the newly created Transportation Security Administration turned accessing a seat on a plane into a major hassle by rummaging through carry-on baggage at security checkpoints; calling for “female/male assists” when metals ticked off magnetometers; and confiscating nail files, toothpicks, and other everyday items that could potentially be considered dangerous.

With our company only months old, we saw an opportunity to build on our lifelong passions for entrepreneurship and transform private aviation by creating a new, more efficient operation to meet an existing demand. Tradewind Aviation was born out of solving a problem for people who had to go through a lot of rigmarole just to get to their vacation homes.

Among the issues we identified was the poor value proposition of commercial aviation for travelers on relatively short flights. For many of them, the process of getting from primary home to vacation home was rife with inconveniences, including a long drive to a major airport, a lengthy pre-departure and security check ritual, tight seating in a crowded cabin, and then another long drive upon arrival. That process is why commercial service to less-trafficked destinations tend to fluctuate seasonally: Major carriers are hamstrung by the traditional airline system, and passengers must settle for what they get.

But a private operator can avoid all that, creating a more efficient and convenient travel experience. Among readily available comforts that we knew Tradewind Aviation could provide were departures from smaller airports, access to private aviation (FBO) terminals and lounges – and best of all, no TSA security checkpoints required.

There were other options available from private aviation operators when we launched our first shuttle route from New York to Nantucket, but not many: Mostly small planes that were not well maintained, with infrequent service and inconsistent quality. So we built Tradewind Aviation around the modern turboprop concept, growing a fleet of Pilatus PC-12s that provide the safety and efficiency of a private jet with much better economics for short- and medium-range flights.

With lower operating costs, Tradewind was able to offer private charter flights and shared charter seats for about a quarter of the price of other private aviation options, expanding our client base to a larger audience. This created a new market, making it feasible for people to travel back and forth between weekend homes and the office without having to invest a ton of time or money – and enjoy the experience.

With the success of our private charter flights throughout the Northeast and New York to Nantucket schedule route, we began adding scheduled flights to more regional destinations: First Martha’s Vineyard, and in 2016 we launched operations in the Caribbean between San Juan and St. Barths, Anguilla, Nevis, Antigua, and St. Thomas. Later we launched service to Boston and Stowe, Vermont from New York and our newest route to Newport, Rhode Island will launch in the summer of 2021.

Spurred by the pandemic, ‘working from anywhere’ is now more popular and feasible than ever. Policies vary by industry, of course, but in general employers are accepting of people working from home to protect themselves, their families, and staff. Meanwhile, people are reconsidering where to lay down roots and raise families, heightening the appeal of areas beyond easy commutes.

Despite the trend growing from the pandemic, we do not think the demand will disappear on the other side. While the initial rush to private aviation during the pandemic revolved around health and safety, we and other operators have seen a flood of new clients come into the fold for other reasons. Essentially, when people realize the efficiencies we offer and that the cost of private aviation meets their budgets, they’re going to stick with it – especially as things like weddings, dinner parties, and face-to-face board meetings that have been on hold for so long become feasible again. 

Meantime, with the private aviation model we created, Tradewind can now fly people pretty much anywhere via charter, with more than 5,000 local airports accessible by our fleet. As more people across the country discover the appeals of ‘working from anywhere,’ we’re looking to expand.