This Pilot Influencer Invites You To Join The Smile High Club

Not every popular social media personality is an “influencer,” but Will Dryden, the pilot, certainly is. Unlike others who promote products, Will promotes something far more universal—smiles. Through his content, he inspires an appreciation for life, lived to its fullest.

Will’s social media following spans thousands of fans worldwide, from his home in the Americas to Europe and Asia. On his platforms, followers of Will Dryden The Pilot enjoy videos where he flies his personal jet, a Cirrus Vision Jet, from his home base near San Diego, California, to destinations like the golf haven of Coachella Valley.

What makes his videos particularly captivating is the way Will shares the cockpit experience. He frequently invites non-pilots to sit up front, giving them — and his viewers — a firsthand taste of what it’s like to command a jet. 

Will inherently has a habit of greeting everyone at airports with a smile. “It confuses people,” he laughs. “People become disconnected from the world they live in. When I get out of the plane on the ramp, I just start smiling to engage people.” This simple act embodies Will’s mission to bring positivity to every interaction.

To understand Will’s sunny demeanour, we must delve into his past — a journey that shaped the man he is today.

From Flying School to Personal Freedom

Until a few years ago, Will owned a thriving multi-location flight school, running it for 12 years.

“Most people in aviation are successful but don’t enjoy life,” Will reflects. “Although I had built a successful business, it was a 24/7 endeavour, especially when planes broke down.” Ultimately, he decided to sell the business and, for five years, he stopped flying altogether. “My best friend thought I was a fool. He says, ‘You got me into flying, and now you’re not even flying yourself.’”

A series of personal losses brought clarity to Will’s life. “Sadly, my family lost five members in four years,” he shares. “I looked in the mirror and said, ‘Yeah, I can have fun flying.’ So, I bought a jet.”

To keep his new Cirrus Vision Jet strictly for pleasure, Will chose to let his flight instructor certification expire.

For Will, selecting the Cirrus Vision Jet was an easy decision. “Its best feature is its simplicity. You don’t need to be an astronaut flying the Space Shuttle,” he quips.

Having used Cirrus SR aircraft at his flight school, transitioning to the Vision Jet felt seamless. “The SR22 to the VJ is essentially flying the same airplane, just at different speeds,” he explains.

Will also emphasises the Cirrus Vision Jet’s safety features, which make it perfect for such trips. “It has CAPS (Cirrus Airframe Parachute System),” he says. “And the Vision Jet already offers Garmin Autoland, so if I couldn’t continue as captain, a passenger could activate Autoland. The system would find the nearest airport, communicate with air traffic control, and land the plane—keeping everyone informed and confident.”

A New Challenge: Golf

Will’s determination has always been a defining trait. A former college baseball player, he likens himself to Rudy, the underdog protagonist of the 1993 film about a dreamer who beats the odds to play for Notre Dame. “I worked my butt off to make the team,” he recalls.

Now in his 40s, Will is channelling that same grit into a new pursuit: becoming a professional golfer. “I thought to myself, when was I happiest in life? It was when I was competing. So, last year, I decided to try it. I lowered my handicap to 6.8 in my first year and a half. I’m giving myself another year and a half to succeed,” he sahres.

To boost his chances, Will enlisted Alex Riggs, the same coach who works with NBA superstar Steph Curry. Not surprisingly, Will has already featured Riggs in one of his flying videos.

⁠“Nothing is possible without my wife, Kathy,” says Will.  “How many wives in the world tell a husband it is okay to try and become a professional golfer at 44?  She is my biggest fan…I’m the luckiest guy in the planet to have her!”

As he works toward his golf goals, Will has also created a new social media persona: Will Dryden The Golfer. “I want to be like Happy Gilmore,” he says. “I’m starting at the bottom in terms of capability and social following. From there, I’ll improve my scoring and grow my audience,” he says.

It’s working, notes Will.  In fact, his favourite brand of golf equipment and apparel, PXG, is now supporting him in his endeavour.

Epic Adventures

Beyond his golfing ambitions, Will continues to chronicle epic flying adventures. One highlight was ferrying a Vision Jet from Switzerland to the United States, an experience he captured in a series of YouTube videos.

The journey showcased his skills, from navigating challenging weather to landing in remote locales where locals carry rifles for bear protection.

Looking ahead, Will plans a two-week trip to South America in late 2025. “I’ll play golf in every country I visit,” he shares. “I’m looking for a couple of people to join — folks who love sharing smiles and ideally have their own social media following so we can collaborate.”

As the famous orphan Annie sings, “You’re never fully dressed without a smile.” For Will Dryden, that smile is his superpower — and he’s sharing it with the world, one flight and one fairway at a time.