Man explains how he became a Gulfstream private jet pilot at just 21 years old

This 21-year-old became a Gulfstream pilot, but it nearly didn’t happen.

Before his 22nd birthday, Owen was flying a Gulfstream G4 – a $40 million private jet known for whisking billionaires across continents in complete luxury.

But how did he get there? It’s a story that almost didn’t take off. 

It meant risking every dollar he had, and for a while, nothing was guaranteed.

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Flying jets at 21 sounds glamorous but the grind is real.

Before he got in the cockpit, Owen came up through the old-school ranks – grinding in turboprops and piston planes, with about 2,000 hours under his belt.

Then a friend told him about a new charter company out of Phoenix flying Gulfstream G4s.

There was a catch: they weren’t hiring full-time. Only independent contractors.

That meant if Owen wanted the job, he’d need to pay for his own type rating – a certification that costs tens of thousands of dollars.

So he did it. He dropped $25,000 of his own money – nearly everything he had – to get certified on the G4.

And for a month, they didn’t even call him.

Fresh out of training with a shiny new type rating, Owen waited. And waited.

Nothing. No flights. No schedule. Just silence.

Then one day at the airport, he spotted a familiar G4. The crew was closing it up, getting ready to head out.

On a whim, he walked up and introduced himself, asking if they needed contract help.

Turned out they did.

That chance encounter landed Owen a second gig, and it ended up being his real break.

With just 25 hours in type, he became the third pilot for that crew. 

He ended up flying with them more than the company he originally trained for, and he finally got the experience he needed, mentored by two seasoned captains.

The stars aligned but Owen is the first to admit it was a risky bet.

“What I did, I highly do not recommend,” he says. “Luckily, it just happened to work out.”

Owen’s co-pilot on this flight? Brad. Also 21 when he first sat in the right seat of a jet – a Citation Sovereign.

Brad’s path was totally different. 

He was a university flight instructor, helping out with a course that happened to give him extra multi-engine time.

That led to friendships with the right people and, eventually, a tip-off about a scholarship for type ratings.

There were four scholarships. Only six people applied. Brad got one.

A month later, he had a CJ type rating and spotted a job posting for a Citation Sovereign. He applied, despite being way under the listed flight hours.

Two days later, he was on a “prove-it” flight in a CJ. He nailed it and got the job.

Aviation careers rarely follow a straight line.

Today, both Owen and Brad are flying jets, logging hours, and building careers most people can only dream of, but they didn’t follow a playbook.

Both agree it’s about timing and being ready to work hard.

So, what’s the takeaway?

Owen’s story is in the hustle: many of us could use the reminder that taking big risks doesn’t always work unless you’re willing to knock on doors and grind through the quiet days.

For young pilots, it’s proof that the sky isn’t the limit,  but it definitely makes you work for it.

You can follow Owen’s adventures over on his YouTube channel, Fly With Owen, or watch his video here:

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