From First Jump to DZO: Tim Allen’s Story

Table Of Contents

• An Unlikely Beginning
• The Day Everything Changed
• The Making Of A Dropzone: WNY Skydiving
• A Little Better Every Day: Philosophy In Action
• Skydiving As Service
• Deep Roots & Personal Milestones
• Words To Jump By
• WNY Skydiving: Today & Tomorrow

Key Takeaways
What began as a single jump in Cancun became a lifelong calling for Tim Allen. From teacher-in-training to Dropzone Owner, Tim built WNY Skydiving into a thriving community defined by safety, mentorship, and heart. His philosophy—“a little better every day”—shapes everything from student training to the welcoming spirit that fills the hangar. More than a skydiving center, WNY is a place where people push limits, find connection, and discover what they’re capable of.

WNY Skydiving is more than just a place to jump. It’s a community, a training ground, and for many of us, a second home. Since 2009, our dropzone has grown from a small, single-plane operation into a full-service skydiving center located on a private airport, powered by a passionate team and a welcoming environment for tandem students, people learning to skydive, and licensed jumpers alike.

At the heart of it all is Tim Allen – our founder, dropzone owner (DZO), and the reason WNY Skydiving exists. With more than 11,000 jumps, Tim holds nearly every rating in the book: coach, tandem instructor, AFF instructor, tandem instructor examiner, coach instructor examiner, rigger, and pilot. If you’ve spent any time at our DZ, you’ve likely crossed paths with him, whether in the sky or behind the scenes helping others reach their next goal.

Tim’s deep respect for our sport and commitment to advancing it the right way influence every part of our operation, from the way we greet new jumpers to the energy in the hangar on a busy weekend.

This is the story of how it all began, and the man behind it.

An Unlikely Beginning

Tim’s path to skydiving wasn’t linear. In fact, it started a long way from Western New York. Born in Niagara Falls and raised primarily in Luxembourg, Tim’s early years followed his father’s international career with a mid-sized air tool company.

He resettled in the US in time for college, where he pursued degrees in communication and math education with the aim of becoming a high school math teacher. But when the 2008 recession hit and job prospects disappeared, that door abruptly closed … just as a new one unexpectedly opened.

On a trip to Cancun, Mexico, Tim booked a tandem skydive. Out of all the typical distractions of college spring break, it was skydiving that pulled at him. It’s the singular decision that kicked off a chain of events that would lead to a very different future.

The Day Everything Changed

Tim made his first jump on March 7, 2001, just outside Cancun. What began as a one-time thrill quickly became something much more. That first taste of freefall stuck with him and by the time he was back home, he was committed to doing it again as soon as the snow melted. Tim shared: 

“At that time in my life, skydiving only had two markers in my mind. Point Break, of course, and a memory from Kitzbühel, Austria. I’d see people floating down the mountain near the ski school hill – literally propelling themselves into the mountain air above the Alps. They looked like they were flying; maybe skydiving. Ironically enough, years later I realized there was actually a dropzone there in the summer. At the time, it just seemed wild, maybe even impossible. But the image stuck.”

Finally, in May, all systems were a go … but on the way to the dropzone Tim crashed his car into a mail truck. Most people would interpret this sort of incident as a sign to turn around. Tim? He called a tow truck, rented a car, and kept on driving. He made his second jump that same day.

At the time, skydiving was a personal pursuit for Tim; something exciting and freeing in a way nothing else had been. He didn’t immediately dive into the industry. He spent time working for his Dad’s company, traveling internationally for trade shows. On the weekends, he jumped for fun and picked up part-time work at a local club dropzone, just enough to keep himself in the air.

But as time went on, that part-time gig started turning into something bigger. 

The Making of a Dropzone: WNY Skydiving

Stepping back, Tim realized he had everything he needed to make a bold move. He’d earned his ratings, bought a Cessna 182 (affectionately known as 85D), and was just one tandem rig away from opening a dropzone of his own. So, with a little push from his wife Kristin and a lot of guts, that’s exactly what he did.

Tim purchased Pine Hill Airport in Albion, New York, and laid the foundation for a new kind of dropzone. In 2009, WNY Skydiving was born.

The goal in that first year was modest: 75 tandem skydives. But by the end of the season, WNY had already doubled that number. What started as a dream quickly began to attract a loyal following of skydivers from across the region. Many of the jumpers who helped Tim get off the ground in those early days are still jumping here today.

A Little Better Every Day: Philosophy in Action

From the beginning, WNY Skydiving has been about progress – growing slowly, steadily, and deliberately. Rather than by a master plan, Tim has been driven by values: “My philosophy has been to do a little better every day.”

And good things have always followed.

For 16 years, this mindset has been the quiet driver behind everything we do – whether that’s refining our student program, investing in gear, improving our aircraft, or simply making sure every new jumper feels welcome the moment they walk onto the dropzone.

We’ve never chased flash or volume for the sake of it. Growth at WNY has always been intentional, and Tim has made sure we keep our focus on what matters most: prioritizing safety while creating a supportive, genuinely fun environment for everyone who jumps with us.

Over time, that steady approach has shaped a DZ culture that’s both laid-back and deeply committed. Around here, people take pride in sharing knowledge, celebrating each other’s milestones, and showing up – not just as skydivers, but as a community.

It’s this blend of professionalism and heart that makes WNY Skydiving what it is today.

Skydiving as Service

For Tim, skydiving has never just been about adrenaline: “It’s about helping people become better versions of themselves by facing fear, pushing limits, and discovering what they’re capable of. To do things they didn’t believe they could, or believed they could but didn’t know how to get there.”

He leads by example; with patience, humor, and a steady belief in human potential. Whether it’s mentoring students, organizing jumps, or supporting our staff in the day-to-day, he shows up with purpose and humility.

Some of his most memorable jumps haven’t been about altitude or complexity, but about connection. He’s taken quadriplegic students on tandem skydives. He’s coached aspiring instructors through to success. He’s shared the sky with people who never thought they’d leave the ground. These are the moments that supersede the challenges that come with business ownership.

Tim has had some phenomenal mentors along the way – Bob McEvoy, Bram Clement, Art Sherry, Sherry Butcher, Tom Noonan, and others who paved the way for him to be able to do what he does today. “My most influential supporter, however, has been my wife,” Tim shared. “Without her, I would have never started the DZ, bought my first tandem rig, bought the airport we jump on, or bought my caravan. At the time I made each of these purchases, they were all large financial, life-changing decisions that without her support and push I’m not sure I would have made.”

Deep Roots & Personal Milestones 

With a hefty log book and an impressive slew of ratings, you might think Tim’s taking some time to relax and enjoy the fruits of his labor. Not so. He’s currently working toward the few remaining ratings he hasn’t earned, always adding to his skillset with the same drive that got him here in the first place.

And yet, Tim hasn’t lost sight of why he started jumping back in 2001: it’s fun.

He still makes time for the kind of jumps that fill his cup. Some he holds dear to memory include RW jumps with friends, winter formations in Z-Hills, and destination skydives in places that carry personal significance. 

One especially meaningful moment was making a jump in Luxembourg where he’d spent much of his childhood. Another came when he returned to Playa del Carmen, where he’d made his very first jump, and got to land on the stunning white sand beach – this time as an experienced skydiver retracing his steps. And perhaps the most unforgettably gorgeous view of all: Nelson, New Zealand at a little DZ on the top of the South Island. 

Whether he’s introducing someone to freefall for the first time or linking up in a big-way formation, Tim approaches every jump with the same sense of curiosity, joy, and gratitude that hooked him back in 2001.

Words to Jump By

With more than two decades in the sport, Tim has seen skydiving from every angle: student, coach, examiner, DZO. But when it comes to guiding the next generation, his philosophy is simple. It comes straight from the chief instructor at WNYSkydiving, Bob McEvoy: “Half as cool, twice as long.” 

That mantra has stuck with Tim through the years, and it’s one he passes on often. In a sport where it’s easy to get swept up chasing the next jump number, the next discipline, or the next Instagram-worthy shot, Tim encourages newer jumpers to play the long game. Build slowly. Respect the process. Stay curious, but stay grounded.

At the same time, he knows that risk and reward often walk hand in hand. His other go-to quote was told to Tom Cruise in Risky Business: “Every now and then, say ‘What the f@%& … Make your move. Freedom brings opportunity. Opportunity makes your future.”

The key, Tim says, is to understand the weight of the decisions you make and the ripple effect they can have on your community, your crew, and your own future in the sport. Skydiving, like life, is full of contradictions. A little optimism, a little caution, and the willingness to own your choices? That’s the sweet spot.

WNY Skydiving: Today & Tomorrow

WNY Skydiving today looks very different from where it started, but the spirit behind it hasn’t changed. We’re still a tight-knit community with a reputation for doing things the right way.

We’ve built something we’re proud of here, one jump, one student, one small improvement at a time. Our private airport gives us the freedom to shape this place into exactly what we want it to be: a welcoming, laid-back, safety-forward environment where skydivers of all levels can grow and thrive.

Tim never set out to build an empire. He set out to build something meaningful. And almost two decades later, WNY Skydiving continues to reflect that original intent – to be a place where people discover what they’re capable of, find connection in the sky, and fall in love with this sport the same way he did.

The journey isn’t over. If anything, it’s just getting good. Come jump with us!