California’s silver surfer: Jason Middleton, Silver Air Private Jets

When he is not running Silver Air or flying, Middleton is often in search of the perfect wave.

What do elite-level triathlon athletes and business aviation have in common? Jason Middleton, CEO and founder of Silver Air Private Jets is one answer, although he didn’t know it himself until late in his racing career. 

“I didn’t grow up passionate about aviation, I was an athlete,” Middleton told us. “I did my first triathlon at 11, joined the US National Team at 14, and turned professional at 17. After high school, I chose not to attend college and instead pursued racing full-time.”

Then began a sustained racing career that Middleton enjoyed up until his late 20s when “the world got faster and I didn’t”, he quipped. After briefly flirting with the idea of working for one his sponsors, such as Trek or Reebok, Middleton, on the advice of a pilot and friend, took a “discovery flight” at Santa Monica Airport, California in 1999.

“I fell in love immediately,” he recalled. “I was about 27 and hadn’t even realised aviation could be a career path for me.”

He committed fully. Earned his ratings, qualified as a flight instructor and began instructing while he finished his racing career. 

“After retiring from racing, I joined SkyWest Airlines, aiming ultimately to fly for Hawaiian Airlines. But 9/11 happened. My training date was cancelled, and I was told not to expect a call back,” he said.

Between surf days (Middleton’s other sporting passion), he soon found work flying cargo in California for a company that also had a corporate aviation division — operating King Airs and light jets. “I didn’t even know what corporate aviation was, but once I saw it, I loved it,” he said. “Different destinations every day, flying business leaders and occasionally celebrities.”

From there he earned his Gulfstream G550 type rating and progressed into management roles. Middleton managed aircraft for the Wrigley family in Santa Barbara and later served as chief pilot for another owner. 

“Sitting between owners and management companies gave me a unique perspective,” he explained. “I saw practices that lacked transparency — revenue not properly accounted for, unclear charter allocations — and began forming strong views about how a management company should operate.”

Around 2006-2007, employing foresight few others applied, Middleton advised an owner he worked for to sell his aircraft before the market shifted. Having sold the plane within a week for more than he paid, Middleton was effectively out of a job, but “with some capital” thanks to a generous bonus from his former employer. 

Silver Air is born

“My friend James Maxwell and I decided to start a company,” he said. “We bought a small Citation jet and a charter certificate out of Fresno [Texas]. Our original model was similar to what JetSuite later became — light jets, point-to-point pricing in the western US, efficient and affordable.”

There is a “growing disconnect” between charter broker and operators, said Middleton.

Before long, the looming collapse Middleton had warned of, reared its head. Money became incredibly tight — Middleton’s house was in foreclosure and he was struggling to put food on the table. “That period forced us to learn our business in detail: maintenance, fuel buying, operational efficiencies,” he said.

Unable to buy more aircraft, Middleton moved into aircraft management, bringing the lessons learnt from early in his corporate aviation career with him. “From the beginning our foundation was to save owners money, drive more revenue per hour and operate with full transparency,” he said. Middleton and Maxwell chose not to build vertically integrated businesses — no MRO, FBO, or catering arm. “Our belief is specialisation. We aim to be the best, not the biggest,” he noted.

Today, Silver Air operates roughly 30–35 aircraft worldwide, ranging from a Pilatus PC-12 to a Boeing Business Jet. It’s also one of a handful of companies to hold both IS-BAO Stage 3 and Wyvern Wingman Pro ratings. “That performance foundation remains unchanged since 2009,” added Middleton.

Fleet demand

Offsetting ownership costs through charter revenue is central to the Silver Air model. The company has around 25 aircraft or 70% of the total fleet on its charter certificate. 

“Many companies specialise in specific aircraft categories, but we aim to serve clients across the full spectrum,” he said.

When adding aircraft to the fleet, Middleton looks for three things. “First, the owner must be quality-focused—committed to proper investment in pilots and maintenance and aligned with our operational approach,” he explained. “Second, the aircraft must be high quality, well maintained, and present well. Third, as a charter-focused company, we prioritise owners who want their aircraft chartered as part of their ownership model. Revenue offset through charter is central to how we operate, and it’s an area where we excel.”

Middleton said demand fluctuates regionally and seasonally, although light jets remain consistently busy covering West Coast hops or trips between the US northeast and Florida.  

Super midsize aircraft, such as the Challenger 300 series, Citation X, Sovereign and G200, see “particularly strong” demand due to domestic range and cabin comfort at lower cost than heavy jets, said Middleton.

Meanwhile, ultra-long-range aircraft see seasonal spikes, especially in summer for Europe and long-haul destinations like Asia, he said.

A shifting industry, especially post-Covid

“Put jumping in at the deep end in aviation terms” into Google and growing an infant charter business through the 2008 crash is all but the dictionary definition. Coming through that adventure and the 2010s to be faced with the pandemic, Middleton has had his share of navigating storms. 

In that time he said he has seen a shifting industry, which is now open to more people than ever before. The biggest shift of all is the “growing disconnect” between charter brokers and operators, he said.

“There are brokers today with very limited aviation knowledge buying and selling air transportation to the public,” he explained. “Many focus primarily on price, not operational excellence or safety differentiation. Technology platforms have made it easy to send quote requests to 30 operators and select the lowest price, which has compressed margins across the industry.”

Compressed margins affect profitability — and that can impact safety investment, he continued. “Robust safety programmes, dispatch teams, international handling and proper operational infrastructure cost money. If operators are working on extremely thin margins, something has to give,” he said.

There’s also the issue of accountability, according to Middleton. “Operators carry regulatory exposure — certificate risk, fines, enforcement actions. Brokers carry virtually none,” he said. “That imbalance is a structural problem.”

“I believe there needs to be regulatory oversight in the charter broker space. Accountability is fundamental,” he added.

Flight Club’s brokerage model

One antidote Middleton has personally established is Flight Club. Which, contrary to the popular 1999 film Fight Club, stresses “education” as its first rule.  

According to Middleton, he created Flight Club to bring operational discipline to charter brokerage. 

“Flight Club operates under our certificate, this means we’re a direct operator, not just a broker with a phone and a contact list,” he explained. “If it’s not our aircraft, it’s a thoroughly vetted partner that meets our criteria.”

Instead of offering jet cards, which Middleton believes can incentivise brokers to maximise margin by sourcing the cheapest aircraft available, Flight Club uses an operating deposit model.

“When a client wants to fly, our team sources four or five aircraft that meet their specific criteria, presents transparent details on the aircraft and operator, and discusses pricing openly,” said Middleton. Once the client selects an aircraft, they fly without wiring funds each time or handling ad hoc charter logistics. Silver Air sends a single invoice afterwards. 

“Education is foundational for us—we want clients to understand what they’re buying, and I often join Zoom calls personally to ensure that,” he explained. “Flight Club was built on service, safety, expertise and client education. If we lose business because we’re not the cheapest option, that’s fine. Clients who value this approach appreciate it.” 

Since launching Flight Club from zero, Silver Air is on track to exceed $100m in annual revenue under the brand in 2026.

Flight Club podcast 

Middleton has also launched a podcast by the same name. Designed as “a celebration of the vibrant tapestry of personalities that make aviation truly remarkable”,  the podcast welcomes figures from across aviation and beyond from pilots to entrepreneurs, and even rockstars. Guests so far have included Top Gun stunt pilot Kevin LaRosa II, Cyrus Sygari, co-founder of UP Partners, and business aviation legend Clay Lacy. 

Covid, a ‘defining moment’ 

The Covid pandemic was a “defining moment” for Silver Air Private Jets. When flights stopped in early 2020, company leadership made the decision to not lay off staff. “Despite near-zero revenue for months, we retained all pilots and support teams,” said Middleton. In fact, the company hired around 30 people during the lockdown.

“That decision reinforced our culture and sent a strong message internally and externally. It strengthened loyalty and positioned us well when demand returned,” he said. 

“Six years later, the company is significantly stronger,” Middleton added. “Our leadership team meets weekly — 13 people in the room — and we work through issues collaboratively. That culture was reinforced during Covid.”

Lessons from the flight deck

Perhaps it was down to muscle memory from his days as a competitive athlete or maybe his love of flying (likely a marriage of both), but, after years focused on executive leadership, Middleton returned to flying in 2023.

He regained his ratings in the Gulfstream G550 and initially stepped into the second-in-command role. 

“It was eye-opening. I saw firsthand how systems were functioning at the product level — crew logistics, SMS [safety management system] processes, hotel bookings, FRAT [flight risk assessment tool] usage,” he said. “It revealed inefficiencies that weren’t visible from the CEO seat.”

Not long after, Silver Air’s director of operations was forced to leave the company following a family emergency. Instead of advertising for new hires, Middleton stepped into the role. 

From his new vantage point “in the field”, Middleton oversaw a rewrite of the ground operations manual, implementation of new training programmes, introduction of new software systems, updates to hazmat manuals and improvements to evaluation processes.

“Change is necessary for improvement. But change must include training and evaluation — many organisations miss the evaluation phase,” he said. “That experience reinforced the value of leadership staying close to operations.”

Leadership outlook 

Despite his hands-on management style creating “real improvements” to Silver Air’s day-to-day operations, Middleton is clear that “if one day I’m not the right CEO, that’s fine. I’ll go fly or surf”.

Many aviation companies are founder-led and pilot-led, he noted. “That has strengths but can limit professional management maturity. As the industry evolves, professionally managed structures may become more common,” he said. “I’m open to that evolution.”

The biggest opportunity ahead for Middleton is “reclaiming control” of the customer relationship for operators. “Brokers have largely taken over the charter customer,” he explained. “Operators need stronger direct engagement and potentially regulatory reform to ensure accountability in the brokerage space.”

Middleton believes more operator control would mean better financial health, stronger safety investment, more pilot compensation stability and higher standards overall. 

Although he has less time to get in the water than he did back in his triathlon days, the “discipline” and “mindset” from endurance athletics still shape how Middleton leads, with emphasis on “resilience, consistency and long-term focus”.

That said, if there is  a good swell running off the Channel Islands of California you may still catch him trying to find the perfect wave.