Not many of us really get to live out our dream, but Ryan Derrickson of Sturgeon Bay, Wisconsin is living out two of his. Growing up, Ryan always dreamed about being a trucker, but the first time he stepped foot onto a plane, he got a new (or second) dream of being a pilot. Now, he flies a 747 cargo plane all over the world through the winter months and then trucks around in a beautiful flat top Peterbilt the rest of the year. He really is “living the dream” times two.
Ryan Derrickson (36) was born in Spring Green, Wisconsin. When growing up, his family moved around a bit, but in 1983, when Ryan was eight years old, they settled in Sturgeon Bay, WI. Living near a major highway, Ryan would sit in the front yard and watch the big trucks go by. From a very early age, he wanted to be a truck driver. Then, when Ryan was 10 years old, the family took a vacation to Disney World in Florida, and Ryan got to experience flying in an airplane. From the moment he got on the plane, he had a new dream – to be an airline pilot.
Wanting to get into aviation, Ryan knew that a good education was key so he always worked hard in school and got good grades. After graduating from high school with honors in 1993, Ryan went on to attend the University of Dubuque in Iowa, where he double-majored in Flight Operations and Aviation Management. In 1995, while in college, Ryan got his CDL and began doing some part-time driving. Throughout most of his aviation career, he has driven trucks on the side whenever possible (Ryan is not one who likes to sit still), and when he’s taken breaks from flying, he always goes trucking.
After graduating in 1997, Ryan got a job flying freight in a small twin-engine Cessna. He did this for about a year and a half and then got hired by a small local airline to fly a 19-seat turbo-prop commuter plane. A few years later he landed a great job, flying a corporate jet for a big insurance company. Two years later, the insurance company moved Ryan’s home base to Boston, expecting him to move there – to which he said, “Thanks, but no!” After that, he got a job at Wisconsin Airlines, flying a 35-passenger turbo-prop for United Express out of Chicago. Then, in April of 2001, he got his dream job.
Anyone from Wisconsin or the surrounding states is probably familiar with Midwest Airlines. For Ryan, Midwest was the company he always wanted to work for. Early in his flying career, Ryan set a goal to be flying “the big jets” by the time he was 40. Well, at just 26 years old, he reached that goal! At that point, Ryan thought he had it all figured out – he’d work at Midwest for about 40 years, make lots of money, and then retire with a nice pension. But then, the unthinkable happened – the 9/11 terrorist attacks. Two months later, Ryan was let go (those were dark times for the airline industry).
Looking to just buy a little time until Midwest called him back, Ryan took a full-time trucking job, driving for a Wisconsin-based outfit called River Valley Express. The fleet was nothing special, but owner Jim Nitzke kept all the rigs real clean and was a good guy to work for. After about a year out on the road, Ryan found himself in a relationship, and you know how that goes.
Wanting to be home more often with his new girlfriend, Ryan left River Valley Express and took a job driving a tanker for Flying J. Three times a day and five days a week, he did the exact same thing – picked up a load of fuel at the pipeline terminal and then took it to their truck stop in Black River Falls. It was nice having steady work and a set schedule, but Ryan got bored really quick. Wanting to get his aviation career back on track (and tired of waiting on Midwest) he took a job at Trans States Airlines, a regional carrier based out of St. Louis, MO.
In the summer of 2004, Ryan met Steve Guntner. Steve was a guy who did construction in the summer and drove a truck in the winter. Both Steve and Ryan loved to play golf, so they got together, and over the course of playing nine holes, they decided to form a partnership and start a trucking company under the premise that Steve would drive in the winter and Ryan would drive in the summer. While Ryan was driving, Steve would go back to construction, and while Steve was driving, Ryan would go flying. It was the perfect situation for both of them.
The two men scraped up some cash and bought a truck – a 1999 Kenworth T2000 – and a trailer – a 1996 Wabash 48’ reefer – and formed Guntner Transport LLC. It didn’t take long for Ryan to realize that he did not know much about buying a truck, as it barely made it through its maiden voyage! A few thousand dollars later, they were off and running again. Ryan ran the truck for about a month before handing over the keys to Steve. Still flying for Trans States, Ryan did all of the dispatching and load planning on his mobile phone between flights. Having only one truck, it was still not that difficult.
In the spring of 2005, Midwest Airlines finally called Ryan back. He jumped at the chance, and before he knew it he was back to flying the big boys – MD-80 jets – and still dispatching on the side. When summer hit and Steve went back to construction, it was difficult for Ryan to truck, but he did what he could, when he could (he did a lot of short hauls). After paying off that first truck, they bought a second one – a black 2003 Kenworth W900L – and hired a driver to run it. In 2006, Steve resigned from his position at the construction company and went trucking full-time, while Ryan continued to fly and dispatch.
Near the end of 2008, Midwest Airlines was bought out by a competitor and Ryan was let go – again – only this time it was for good. Ryan decided to step away from aviation and focus solely on the trucking company, which at this point had three trucks and three trailers. About that time, one of their drivers left so Ryan got in the W900L and hit the road. Ryan drove hard throughout 2009 and into 2010 and really enjoyed being an owner operator. He ran where he wanted and hauled what he wanted, always following the good-paying freight.
Running through Pennsylvania on a fairly regular basis, a flat top Peterbilt, parked in a farmer’s yard, caught Ryan’s eye one day. Over the next few weeks he passed by that rig several times before noticing that it had a “For Sale” sign in the window. On the next trip by, he stopped to look at it. The truck, which was a 1993 Peterbilt 379 Extended Hood with a 63” flat top, a 3406B Cat engine, a 270” wheelbase and an old-school 15-speed transmission, had been sitting for a while and was beginning to deteriorate, but Ryan could see that it had potential, so he bought it. After limping it home 800 miles on bad tires and with no windshield wipers, headlights or working gauges (other than a tachometer), Ryan dropped the tired truck off at Homer’s Custom Chrome in Milwaukee, WI on January 16, 2010.
Hoping to rebuild the rig and then debut it at the show in Wildwood, Florida, the goal was to finish the truck by April, but once they started tearing it apart, they found a bevy of issues that set them back several months, including serious structural and electrical problems. Once these things were fixed, the customizing could finally begin, but now the deadline was August (for the truck show in Waupun, WI). Thinking he would have a truck to drive in April, Ryan hired a driver to run his old W900L, but once the project was delayed, he found himself with nothing to do. So, he decided to hang out with Homer and the guys at the shop every day, Monday through Friday, until the project was completed – he even slept every night in the sleeper of Homer’s wrecker (our August 2009 cover feature). Over this time, Ryan forged a great friendship with Homer, and now he feels like a member of the family.
Homer Schultz and his crew (JP, Mike and Brian) worked tirelessly to build Ryan’s “classy hot rod” truck. When it was completed early in June, Ryan couldn’t wait to get it out on the road, but on that first trip, he blew a head gasket and had to sit for several days (and spend $20,000) to get it repaired. On the next trip out, rolling along at 70 mph, he blew a steer tire and put the front end down hard on the pavement. Back to Homer’s it went for repairs. This poor guy just couldn’t catch a break! When the rig finally made its debut in Waupun, it was well-received by both the crowd and the judges (Ryan walked away with three 1st place trophies that weekend).
The completed rig now features Sunburst Orange metallic paint with a black frame, a 305” wheelbase, Jones Performance front fenders, a Valley Chrome bumper with a flip-up kit and 8” Dynaflex pipes. It also has 6” cab and sleeper extensions, stainless Hogebuilt half fenders with hidden brackets and two flush deck plates (one in front of the 5th wheel and one behind it). All of the lights and horns atop the cab were removed and then a painted visor, complete with nine tiny flush-mount LED lights, was installed. All of the airline connections were moved into a recessed box on the custom tail plate, and single round headlights, on Double JJ brackets, were installed. The “Convoy Duck” hood ornament completed the truck’s exterior details. But as great as the outside of this rig is, the inside is even better.
The interior of Ryan’s truck features a unique old-school airliner theme, complete with “Fasten Seat Belt” and “No Smoking” signs on the custom overhead console that look like they were taken right out of a 1960’s jet, but they were handmade out of automobile dome lights and custom-cut vinyl. The door panels, walls and ceiling are adorned with aerodynamic-looking “swoosh” stripes, again, reminiscent of an old airliner from the 1960s. The cab has a Rosewood floor, and the plastic dash panels were replaced with painted metal plates, made by Rockwood. All of the upholstery, including leather seats with “Flight 305” embroidered on the headrests, was done by Steve at Straightline Upholstery. Back in the sleeper, Homer added a rear window, a flat-panel TV, a mini fridge (painted to match), and plenty of speakers in custom boxes for the 1,200-watt sound system. They also converted the truck’s single shifter into a 2-stick setup (the second stick controls the splitter), and used modified, chrome, exterior grab bars, topped with old-school glitter knobs, for the shifters. The entire interior, done in cream and burnt orange to match the exterior, is absolutely flawless.
A cool truck needs an equally-impressive trailer, so Ryan refurbished a 2003 Great Dane reefer he already had. The 48’ trailer has an extra wide 11’-2” spread and features polished rails and a polished front, a painted-to-match frame and Thermo King unit, oversized mud flaps and weights, and polished rear doors with painted hardware. Ryan also had Homer install a Hendrickson lift system on his front trailer axle, so he can lift it when bobtailing or hauling a light load. When hooked together, this matching truck and trailer makes a classy combination.
Shortly after the truck show in Waupun, Ryan got another flying job, and this one is even better than his “dream” job at Midwest Airlines. Ryan now flies cargo all around the world for Kalitta Air in a huge 747, which, oddly enough, has eighteen wheels, just like his truck. Last year, he parked the truck in November and went flying for nearly four months straight, racking up the overtime and filling in for everybody who wanted time off during the Holidays. In those four months, he practically earned enough to live on all year, but come March, he got out of the plane and back into the truck. Since March, he has been running all over the country, chasing the produce, going everywhere except California (his reefer is not CARB-compliant). He plans to run hard until October, and then park the truck and get back into the plane. Not a bad deal!
Ryan wanted to thank Homer Schultz and his entire crew for all of their hard work, as well as Carl Carstens at Rockwood Products. He also wanted to thank his parents, Roger & Kay, for all of their support over the years. Although they divorced when Ryan was 12 years old, he still has a great relationship with both of them.
Ryan Derrickson loves being a pilot, but he loves the freedom of the open road even more. He has found a way to live out not one but two of his dreams – and in a world that often makes it hard to dream at all, that is quite the accomplishment. It just goes to show, when the sky’s the limit, you can do anything – especially when your “other 18-wheeler” has wings!