Ryan Osmond took a chance, ditched his tedious job, and followed his dreams. Now, his backyard is the REAL Watersports slick, and his day-to-day has him creating photos and videos with the best riders in the sport. Get to know this British/American media producer who is equal parts talent, dedication and hard work.

In a new feature we look at some of the personalities within our sport who have changed their lives through a love of kiteboarding.

Ryan Osmond took a chance, ditched his boring job, and followed his dreams. Now, his backyard is the REAL Watersports slick, and his day-to-day has him creating photos and videos with the best riders in the sport. Get to know this British/American media producer who is equal parts talent, humility and hard work.

Can you tell us how you went from an engineering apprentice in the UK to a globe-trotting kiteboarding instructor to a year-around employee at REAL Watersports?

I’m fortunate to have a supportive, well-travelled, American mother. She graciously spent every bit of her savings taking me to new and exciting places around the globe when I was young. I think now she feels like that backfired on her a bit because I live 4,000 miles away.

At the age of sixteen, I moved two hours away from home to work as an apprentice for a prestigious, well-known, aeronautical engineering company with the dream of having a fulfilling career as an engineer. After completing my apprenticeship, I realised a job in manufacturing engineering wasn’t all it was cracked up to be, and my life quickly became stagnant.

To spice things up a bit, I took up new hobbies like rock climbing, kayaking and scuba diving. With new sports, I ended up spending a lot of time waiting around for someone to go and do activities with me, which I didn’t take well to.

One day, out of boredom, I picked up an entry-level Sony DSLR. I quickly realised photography was something creative and interesting I could do that didn’t require relying on others. So I would spend my weekends walking through the city, taking pictures of art and scenes that piqued my interest.

Then one day it came to my attention that a colleague at the engineering company was selling some windsurfing gear for £50. I decided that windsurfing was another new hobby I could do on my own, so I bought it and, that weekend, took it back to my hometown on the coast where I had seen others sailing in the past.

After spending a crazy amount of time attempting to rig and sail this thing, which I later realised was from the 70s, two people from the windsurfing shop across the road offered some free instruction along with some user-friendly gear. Within the next hour, I was comfortably sailing back and forth. It was at this moment that I knew my life just changed forever. 

From that point on, wind sports became my obsession. Windsurfing quickly transitioned into kiteboarding and weekends spent kiting were what I lived for. Eventually, factory life became too much. I would read kiteboarding magazines and think, these people are my age and travelling the world doing what they love. Why can’t I do that?

So, I took action. I trained to become a kiteboarding instructor and quit my engineering job that summer. My colleagues and friends said I would never be lucky enough to get another job like that again. But summer soon turned to winter, and with my newfound freedom, there was no way in hell I was going to stay in the UK, so I hopped on the next flight to Miami, Florida. 

Upon arrival, I soon found Florida wasn’t all Ferraris, palm trees and beautiful women. The promise of an instructor job and place to stay turned out to be a spot on a two-seater couch in a cockroach-infested apartment that was located in the heart of Little Havana and a job shuttling people across Biscayne Bay on a leaky boat without a captain’s license. Not the Miami I was expecting!

After a few months, I landed an instructor job at REAL Watersports. It’s cool because I arrived during the Triple S Invitational and was completely awestruck. I had seen articles about this event in the magazines I had read in the factory. Now I was there, kiting amongst my idols. Imagine any other sport where you can just turn up and hang out with world champions! I don’t think there are many.

REAL Watersports became my home between March and October. I worked my way up the coaching ladder and eventually became their highest-level instructor. In 2014, after coaching for a few years, I decided to take a break to travel for a year. During this time, I focused a lot on photography and documenting my travels.

I was predominantly using my iPhone to film unique and interesting scenarios I would get into. This one time, my buddy Paul and I took a job on a commercial tuna fishing boat that broke down five days into the trip and 300 miles off the coast of Australia. I documented it all on my iPhone and put the video on YouTube. I think that’s ultimately what landed me the job I have now as REAL’s photographer and videographer.

It’s funny how things in life always have a way of working themselves out, because about five months into what I thought was going to be a year-long trip, my money started to dry up, and the constant travel between hostels was getting to me. I wanted something more stable, and more importantly, I wanted something with some longevity, a career.

It just so happened that around that time the photographer and videographer at REAL was making plans to move on and contacted me to keep an eye out for an opening. In a mad rush of excitement, I flew back from Hawaii just to show my interest in the position. I watched every tutorial on photography, videography and marketing available.

For some unknown reason, REAL decided to take a leap of faith with me and, for this, I will be forever grateful. Together we’ve done some cool things and moved in an excellent direction, and my love for my job has only grown! Stoked!

What is your position at REAL Watersports and what does your day-to-day life look like?

I’m the Photographer and Videographer at REAL Watersports. I’m responsible for producing all the eye candy you see on our website and the majority of the content on our social media. My job is super cool and allows me a ton of creative freedom. One day I’ll be in the REAL slick shooting one of our team riders and the next I could be creating a resort video.

Just the other day, I got a text from Trip Forman, Co-founder of REAL, informing me that we were going on a 36-hour road trip to NYC to film ‘The Roots’ announcing their set dates for the Wind Voyager Triple-S Invitational. And, as a side perk, we got to sit in on the Tonight Show! So it’s a pretty rad job.

Some of the other things I do are film and edit all the product reviews and plan & organise the media coverage for all our events.

When did you become interested in photography/videography and what sparked your interest?

It’s quite funny; actually, I first became interested in videography after I begged my mom for a video camera for my 11th birthday. She didn’t know it, but it was because my friends and I wanted to film our own rip-off of the show Jackass. We planned and executed all sorts of stupid stunts that mostly involved pushing each other down frighteningly steep hills in shopping carts. Thankfully, none of us had any serious injuries, but I walked away with an interest in videography.

Many of the Wind Voyager Triple S Invitational riders have likely been rolling into Hatteras, with spring SW sessions in full swing. Who is looking hot going into the Triple S? What are your predictions for the event this year? What about local OBX talent to keep an eye out for?

The talent in the Wind Voyager Triple S Invitational just keeps going through the roof. I’m in a fortunate position because I get to watch each clip when I’m logging and archiving footage in the run-up to the event.

For the men, here’s my list: Brandon Scheid is looking good this year. He always goes so huge and is consistent. Noè’s progression, precision and style will likely place him high in the rankings. And, of course, Ewan Jaspan & Sam Light are always up on the podium.

The women’s division is looking a little closer this year. Annelous Lammerts is looking good on the kickers. Julia Castro has been getting some pretty sick rail hits, so it should be interesting.

Never write off the home squad. REAL Watersports coach Jeremy Jones has been putting in a lot of hours in the park this year. Aaron Roberts is out for redemption after dropping off the rankings last year and will be one to watch as he’s hunting for a spot back in the event via the Wind Voyager Triple-S Open.

What’s your favourite Triple S moment?

After the event when I can finally get some sleep! Just kidding. I have two favourite moments.

My first is the awards party. Thanks to Wind Voyager, our title sponsor, each year the party has been getting bigger and bigger with more prize money and more insane talent. Everyone is on such a high after catching up with good friends and riding in the REAL Slider Park. Pair that with some big checks, and you’ve got one hell of a good vibe.

My second favourite moment would be the Waves Market & Deli Street party! The Red Bull DJ truck pulls up in the parking lot and supplies the tunes, and the Deli stays open late to provide all the IPA’s and drunk food anyone could ever need.

What can fans look forward to at this year’s Wind Voyager Triple S Invitational?

Fans can look forward to insane riding from the world’s top park riders and an incredible music lineup featuring: Ky-Mani Marley (Who, by-the-way, is learning to kiteboard), 2 Chainz, The Roots, and the always amazing Dubplates.

Do you prefer shooting photo or video? Why?

I feel like I go through phases of preferring one medium over the other. A lot of people don’t realise that they are two different beasts that require different planning, setup and composition.

The beautiful thing about still photo is that you can plan and execute a shot, go back and edit it and you’re done. Whereas in a video, shooting and editing are only a fraction of the project. You still need to build a collection of shots to tell a story and edit the collection together in a way that makes sense, is exciting and achieves the goal for which it was designed.

These extra steps are part of the reason I like videography because I can tell a story with words and visuals and lead a viewer down a certain path. It’s as though I can share my interpretation of something with an audience. Kind of deep, but I like being able to explain a little more via videography.

Who are your favourite riders to work with and why?

Evan Netsch is talented, approachable and doesn’t have an ego. He rides for fun and doesn’t confine himself to one specific type of riding. He’s also really easy to work with because, like a photographer, he’s dedicated in his riding to getting a great shot. We’re always bouncing ideas off each other and planning tricks around ways to get a new or unusual angle.

I also really love working with REAL coaches like Nick Baines, Jeremy Jones, Aaron Roberts and Austin Leder. These guys are continually stepping it up in the REAL Slider Park. They are always game to shoot and set up unique and exciting features for cool shots.

If you were asked to share one piece of advice for an amateur photographer looking to shoot a few good kiteboarding images, what would you say?

Get to know the nuances of the sport and find a suitable rider willing to work with you. Understanding what is considered proper technique and a well-executed manoeuvre will help you to capture more desirable shots and differentiate you from the average vacationer firing off stills from his iPhone of the guy flying through the sky without his board.

How often do you find time to ride, and what are your favourite sessions?

All the time! One of the benefits of working at the world’s largest kiteboarding resort is that I have unlimited access to every piece of gear we sell in every size. The launch site is literally outside my office, so whenever I find a moment to take a break, I’m out there in the time it takes to rig up and put on my harness.

My favourite sessions are the super windy (30mph+) days doing kiteloops in the slick with friends. We’ve also had some killer downwinders in the slick with some insane land gaps and tacks through the channels.

What shoot are you most proud of?

I’m proud of a shoot I did last year with Evan Netsch. I had seen GoPro footage of him doing a strapless, front roll over a 12ft pier and thought it would make a cool sunset shot. We planned it out on a day that had the perfect forecast, brought a flash and worked until sundown to get the perfect shot. It was cool because there were a ton of tourists on the pier who ended up in the shot and you could see the wonder in their eyes each time they saw Evan fly across the sky. He must have jumped over that pier 50 times, but we got the shot!

What motivates you to create new and different content?

I’m motivated by different stories I want to tell or feelings I want to convey, along with the ever-changing space of digital media.

In the past few years, we’ve gone from low-res, clunky capture devices with almost no way for the individual to reach an audience to mega high-res consumer devices with an obsession with visual quality. Platforms like Snapchat and Instagram, with the emphasis, is on hyper-frequent entertaining short-form content, have also changed the game.

Changing how I create content is super interesting to me. I think too often in this industry we get hit with mega technical jargon and are shown unattainable riding. I want to focus on why we love kiteboarding and the feelings we receive as a by-product of that love for the sport.

What does the future hold for Ryan Osmond?

I will be here in Cape Hatteras at REAL Watersports for a while longer. Someday, I think I would like to run my own media company focused on travel and action sports. I’d love to work with a creative team similar to that at REAL. There’s nothing more refreshing than throwing around a bunch of wacky creative ideas with a team, figuring a way to execute them and seeing them come to life.

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By Lindsay McClure
Lindsay is a pro rider from Hood River in the USA, she works for IKSURFMAG as our Features Editor and is an integral part of the team. Lindsay is really into wakestyle riding and can be found in the Hood River Slider Park during the summer months, she also travels all over the world with the World Class Academy helping younger riders develop through kiteboarding!

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