Private flight is a luxury limited to the über-rich or über-obssessed. Unless you have the financial resources or connections to obtain a plane, a pilot, pay fuel costs, insurance, maintenance, and hangar fees, you will be stuck flying commercial, with all the wonders of torture that TSA and the airlines can muster.

As someone who has flown both private aviation and commercial – the choice isn’t even comparable. It’s literally the difference between being on the Veranda Deck of the Titanic, with tea and crumpets and a quartet, versus being not in steerage, but the coal room shoveling in sweltering 120 degree heat. So I completely understand the allure of some to this idea of bliss of command, chartering aircraft and hopping on board. Even the cramped quarters of a Piper Archer or a Cessna 172 are preferable to the routine one has to endure at any airport and the wasted time of a 30 minute ride on a turboprop really requiring five hours of the day going through security, waiting for transport, and retrieving one’s baggage before moving onward to one’s destination.

Commercial air travel is largely a monopoly, observers note, and so there has been this constant wonder of – well, if Uber and Lyft could break the back of the monopolies of the taxi/hack bureaucracy – why can’t we have an “Uber” for flying?

The answer is, we can, but not without a rethinking air travel generally, changing a fair amount of the law, and suddenly dramatically increasing the supply of aircraft and pilots.

The first step, however, is we have to revisit the FAA “ban” on the innovation ideas generally and put American ingenuity to work on the problem.

The Magic of Uber

I resisted using Uber until my last trip to Atlanta for the MRO America’s conference. About three weeks before, I had used cabs entirely shuttling myself around Ft. Lauderdale at PB Expo. It was an awful experience. Cabbies would take forever to come – I’d see 20 Uber/Lyft drivers come and go in the time my cab would show. Sometimes the cabs wouldn’t come at all – and I’d have to call twice.

So after that experience, I decided – ok, let’s see if I don’t get murdered in an Uber. Desperation is perhaps a bad motivator for adoption, but alas, such was my case.

It was a pleasant experience. The guy was nice. The car was clean. He showed up at my hotel so fast, that I realized if I called for an Uber I better be standing where I expected to be picked up.

It was awesome. I used 20 drivers in the four days of the conference. It was quick, easy, cheap, and on demand.

So I get the idea of people wanting aviation to be like that. I really do.

Devolution versus Evolution

But consider why Uber works. Essentially there’s all this “surplus” supply of people who could drive around in cars. There are all these people who need to get someplace. So Uber and Lyft market make and connect the supply to the demand. Genius right?

Yeah, it is. But it’s also made possible by the fact there are hundreds of millions of cars and drivers who are licensed to drive. And a fair number of the Uber drivers – that’s essentially now their profession (from talking with them). Most of my Uber drivers in Atlanta were former cab drivers. So you have millions of drivers devolved from the bureaucracy that used to be the hack bureau system. They devolved an existing network of supply.

None of that applies easily for aviation. To be equivalent, it would like a Captain for Southwest Airlines deciding to take that 737 out on his own, and say to people, “OK! Who wants to go to Vegas!” That’s not how airlines, charters, and even private aircraft is structured organizationally. To make an “uber of the skies” aviation would have to EVOLVE not devolve.

It’s not impossible, but, we kind of shut down the whole endeavor before it got a chance to get off the ground.

In hindsight, that was a mistake, but it’s a correctable one.

How the FAA killed Uber of the skies

A company called Flytenow was designed to connect pilots and passengers in a way that Uber tried to connect drivers and riders. The company’s founders, Alan Guichard and Matt Voska, developed an online platform to match individual pilots with passengers willing to share the expenses of flying. (See this interview with Flytenow’s founders to learn more – it’s a great podcast.) While Flytenow was in operation, people could fly in private planes and ferry passengers on a cost-reimbursement basis. Everyone seemed to be a winner.

Here’s where you cue the “dum dum DUUUUUM” music – the FAA.

Unlike Uber or Lyft, the emerging apps like Flytenow intended to do nothing more than the bulletin boards in general aviation airports: connect private pilots and passengers for the purposes of sharing the cost of a flight. Unlike with the ride-sharing services, no one was earning a profit—that, people feared, would violate the FAA’s rules.

But despite attempting to avoid the profit motive, the apps did resemble ride-sharing services and caught the attention of the FAA. Pilots and passengers had individual profiles, and a ratings system provided feedback for other users. The entire point was to essentially market make people finding flights. Although in theory, the private pilots didn’t take just anyone, this was considerably difficult to demonstrate in fact. If pilots took anyone where they wanted to go, even on a cost sharing basis, would that run afoul of federal law. Companies like Flytenow argued it didn’t.

The FAA wasn’t convinced.

Holding out for Uber planes?

The FAA determined that pilots who partnered with Flytenow are “common carriers,” even though the pilots could not make a profit from passengers — they could only defray a proportional amount of flight expenses.

Common-carrier designation subjects pilots to the highest level of safety, training, and maintenance regulations, including expensive licensing fees and heightened liability insurance, inspections, and certifications. This jump in regulatory oversight made it impossible for most private pilots to comply. Flytenow, and all others like them, were effectively closed by the FAA’s regulatory determination.

Flytenow sued the FAA, and in 2015, the DC Court of Appeals, ruled against Flytenow, holding in part:

The FAA’s distinction between pilots offering expense-sharing services on line to a wide audience and those offering expense-sharing services to a limited group is justified: holding out to the public creates the risk that unsuspecting passengers, under the impression that the service and its pilots lawfully offer common carriage, will contract with pilots who in fact lack the experience and credentials of commercial pilots. Regulators have good reasons to distinguish between pilots who are licensed to offer services to the public and those who are not, as other courts have recognized.

This effectively killed any chance for anyone to make an “Uber of the Skies.” Flytenow attempted to appeal to the Supreme Court of the United States, but it declined to hear the case – making the DC Court’s holding the final opinion on the matter.

Common Carrier?

In a 2017 paper for the Mercatus Center, Christopher Koopma blamed the FAA’s ban on the fact that Congress failed to clearly define what constitutes a “common carrier.” Without any definition in federal statute, the agency was left to make its own determination, which it did in 1986 by creating a four-part test.

That test requires:

(1) a holding out of a willingness to (2) transport persons or property (3) from place to place (4) for compensation. This “holding out” which makes a person a common carrier can be done in many ways and it does not matter how it is done.

This test makes it nearly impossible to make an “uber of the skies” since the “holding out” provision of the law is the core of how these market making services work – whether its Uber, Lfyt, AirBnB, or whatever.

Before flight sharing apps like FlyteNow launched, developers approached the FAA to receive permission that they weren’t running afoul of the law. Acting on their own authority, the FAA used their own common carrier test, ruled the apps to be effectively the same as a commercial airline, and “imposed a significant limitation on the right of private pilots to engage in cost-sharing to which they would otherwise be entitled,” wrote Koopman.

While I think we all agree safety is a paramount concern, the reality is the FAA acted hastily to shut down flight-sharing because of concerns that hadn’t yet materialized. When the four part test was made in 1986, the availability of air travel helped fuel the economy. Thirty plus years later, the lack of available air travel, and the pressure that smaller urban areas are under, makes the case to revisit this standard.

Long Term, something will have to emerge

While “Uber of the Skies” is grounded in the US, something is going to have to change because of the challenges of the pilot shortage, the challenges faced by regional service, and how aviation is changing.

First, people are getting fed up with the constant unbundling and reduction of basic service of the carriers. While this unbundling has saved the legacy carriers from their constant “boom bust” bankruptcy whiplash, it’s created a building backlash against the “feeing frenzy” that has been unleashed against the travelling public. To make matters worse, smaller urban and regional areas are being squeezed out entirely, with services no longer provided by airlines.

Point to Point Specialization?

Our agency has been approached almost monthly since we started by at least one company attempting to offer a specialized charter between two airports. In some cases, the company owns the underlying planes and they’re operating as either a part 91 or 135 charter. In other cases, they’re actually brokers for underlying 135 charters – they’re the middle man.

They all attempt to solve the same problem – time wasted.

The reason why the rich own airplanes, is that it saves time, and time is money. Being able to pick up and go anywhere as fast as your plane can carry you is a key element of the wealthy’s ability to manage their money. Rich people buy time. Poor people sell time.

These charters attempt to bring some of that value to those who couldn’t afford to have their own airplane. We had one person approach us attempting to connect two cities that were only about 90 minutes a part by direct route. However, because of the lack of pilots in regional air system, that flight now took five hours, as you had to fly to other destinations, wait, then fly to other destinations, wait, then fly to your actual destination.

Will Uber Flight Charters work?

Do I think these “airlines” are going to be successful? Maybe.

Most of these companies that approach us are rather specific in attracting a clientele that is below that of who could afford their own G550, but considerably above the general flying public in how they value their time (and subsequently their money, most of these tickets contemplated by the companies who approach us are north of $1500 each way). These companies are usually using Bombardier, Gulfstream, and Embraer aircraft, all of which probably can deliver a profit per mile that is high enough to offset what are some pretty substantial costs in light of the FAA’s determination and the fact that these companies are acting as air charter services (thus complying with the heightened regulatory requirements).

But the challenge they’re all trying to solve is – there’s some group of people who need to get A to B – and they’re not being met in that need by United, Delta, American, or Southwest. There aren’t a lot of these opportunities at the moment, but that will change as the long term funding for airports, and the pilot shortage, drives many of these communities to figure out solutions to keeping themselves connected to major metropolitan areas.

This type of innovation is much more likely to solve the problem of “uber of the skies” in having access to flights. Uber and Lyft are working on “air taxis,” but those taxis are at best going to be confined to site to site transport in major metropolitan areas at under five thousand feet and about 60-70 kts. Whether that idea will be successful remains to be seen, especially given the fact that technology has been around for about 80 years – namely, the helicopter.

Global Pressures could force regulatory relaxation

There’s also the global scale of this issue. While the FAA decided “No soup for you,” the British aviation regulators haven’t been so stringent when it comes to flight sharing.

Wingly connects private pilots with members of the public so they can share the cost of a flight, and has been variously dubbed “the Uber of the skies” and “the Airbnb of aviation”. Most of the pilots fly small single-engine piston planes with between two and six seats. The company focuses on sightseeing trips and excursions, although it does have some degree of service to those attempting to use it to commute from A to B.

As other countries have invested in drones, flying taxis, flight-sharing, the US Congress hasn’t been completely immune to the idea. The Aviation Empowerment Act, a bill introduced in May of last year by Sen. Mike Lee (R-Utah), maintains the current prohibition on private pilots making a profit off flights offered via flight-sharing apps, but it would otherwise allow for the creation of digital billboards advertising trips. It would effectively create a system in the US similar to what the British are allowing with companies like Wingly.

Conclusions – Can we build Uber of the Skies?

If we could figure out a way to do it, flight-sharing unlocks 200,000 licensed general aviation aircraft across the country and opens routes to and from the 1,904 local and basic airports that serve all states and regions. This makes flying far more feasible and affordable for a far larger swath of the population, opening up new opportunities for work or travel.

While I don’t think all 200,000 pilots will suddenly become “Uber Flyers,” some percentage will.

Overall, revisiting flight-sharing will help build more pilots (which everyone needs), and force a focus on pilot safety (which while good, is nowhere near the level of control or safety found in part 121 operations).

More importantly, if America took legislative action to define the “rules of the road” for the FAA, it would allow entrepreneurs to figure out a way to hit that sweet spot and connect municipalities that are likely facing an end of service as the major carriers and regional airlines struggle with profitability in a cost-competitive environment.


  1. Innovation doesn’t only exist in grey markets.

    Only as long as the general public would be willing to accept the same risk as riding the same distance on a motorcycle, then this makes sense.

    (The safety statistics for flying under part 91 are terrible, and are about the same as motorcycles.)

    I took a deep dive into the topic here:

    We built FlyOtto to match travelers with pilots and planes, on-demand. But we did it within the intent and the letter of the law.

    • Thanks Rod. I read your piece just now.

      I think the stuff you’re trying to do with FlyOtto… and others that are trying to essentially build networks with Part 135 carriers… will move forward regardless of what the FAA does regarding the “common carrier” standard. I agree that the Part 91 record is awful… and general aviation overall is also pretty sketchy when you compare it to 121 operations. That’s why I think if we’re going to do this… then the FAA and Congress are going to need to promulgate some degree of standards about how planes are going to be made safe and inspected properly. I personally would never just jump on a private plane unless I had full confidence in the pilot and knew how the plane was maintained…

      … but that’s just me.

      PS – Always thought I wanted a motorcycle… then I rode one… as so scared out of my mind… never got that itch again. LOL! 😀

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