My Career Path
I’ve been fortunate to have an amazing career, one that’s just getting started. You asked for me to share a summary of each step that led me to United Airlines, so here it is!
No two pilots share an identical career. In part, that’s because aviation is changing so quickly. For better or worse, the path I’ve experienced won’t match your journey. And there’s nothing wrong with that! I post online because I want you to learn the ins and outs of the coolest job in the world, from the mistakes I’ve made to the incredible opportunities that have changed my life.
Career Summary:
Private Pilot - HOVA Flight School, Part 61 (Richmond, Virginia)
Youtube and Social Media - Day One of Flight Training to United Airlines
Boldmethod Pilot Training - Writer, Editor, and Co-Owner
The University of North Dakota - Aerospace Degree and Flight Training, Part 141
Mokulele Airlines, Hawaii - My First Pilot Job (Cessna C-208 Caravan)
Envoy Air - First Officer (Embraer E-145)
United Airlines - First Officer (Boeing 757/767)
The Beginning
I grew up in a family with no pilots or background in aviation. Most pilots can think back to something that sparked their love for flying. For me, it was of my grandfathers. I can remember growing up building models with them, and planespotting at the airport with a handheld radio. With the support of my family, that passion grew into something very tangible.
In high school, I couldn’t quite figure out what made me stand out. I was surrounded by friends that were noticeably talented and driven; student council presidents, varsity athletic captains, and even an incredible acapella singer. When I thought about my next step and what I wanted to accomplish in my life, I thought back to my passion for aviation. Frankly, it made me a little nervous because it was so out of the box and I was about to attempt to become the only pilot in my family or school.
After some careful thinking, I finally brought the idea up to my parents. I have a vivid memory of sitting down at Starbucks with my dad and a laptop loaded with a PowerPoint presentation I made to explain the steps it would take to become a pilot. Being a business professor, I’m not surprised I was basically caught up in my own “Shark Tank” moment to get them on board. I’m so lucky to have parents that supported me from day one. Their only request was that I spent time reaching out to other pilots to learn about the job since they had no advice to offer.
Why Social Media?
With no family to offer advice about becoming a pilot, my first stop was online. I started emailing and messaging every professional pilot I could find who posted content about their career. Many of them wrote blogs about the job, and some became mentors that support me to this day (you know who you are!). The support and inspiration they offered reinforced that I was making the right decision.
At the time, in 2012, aviation and social media were nothing like they are today. I couldn’t find exactly what I was looking for… Something comprehensive and in-depth following a pilot’s career. So I decided to make that my mission, sharing my progress with all of you. From my first lesson to flying at United Airlines today, I’ve focused my energy on filming behind the scenes. On my YouTube Channel and Instagram, I’ll help you understand the ins and outs of this amazing career. I hope that my content inspires you, teaches you what to expect, and gives you the confidence to chase your dream.
Private Pilot Training (Part 61)
In 2012, I started training for my PPL just before my 16th birthday. Just North of Richmond, Virginia, you’ll find Heart of Virginia Flight Services (HOVA), my first flight school. My primary training was conducted in the Italian Light Sport Tecnam P2002 Sierra and Tecnam P92 Eaglet. Both were easy, fun, and cheap to fly! So that we can laugh about the price in a few decades, they were about $80 an hour with gas! One of the agreements I made with my parents would be to self-fund the first part of my PPL so that I had skin in the game.
I spaced out my training between my 16th and 17th birthday with lessons roughly every two weeks. To diversify my flight experience, I took a few lessons during family vacations in places like California and the Outer Banks. In the meantime, I filmed videos and wrote articles for my old blog about each step. Just after turning 17, I became a licensed pilot.
Boldmethod Pilot Training
You may know that I’ve closely worked with Boldmethod as a writer, editor, and co-owner. It’s one of the most popular flight training resources online, helping thousands of pilots reach certification. What you may not know is that I’ve been working with Aleks and Colin since high school. Just after becoming a private pilot, they saw what I was creating online and reached out with an interesting idea.
They were transitioning their consulting and software business back into general aviation, their real passion. Aleks and Colin wanted to begin creating content with someone who was about to experience each step of professional flight training. Fortunately, my love for flying and creating content fit the bill. I started freelance writing during my initial training and later became a co-owner in college, a partnership that has lasted for many years. I owe much of what I know about storytelling and creating content to Aleks and Colin.
Two Special Pilots - Rod & Haley
Aviation is often about who you know, not just what you know. The friendships you’ll make in this career are unlike any other. In 2014, I was at a family reunion in Gulf Shores, Alabama, and wanted to fly over the beach for the first time. I called a local flight school to arrange a sightseeing tour/flight lesson with my family. Rod was randomly assigned as my instructor.
Beyond being one of the most knowledgeable pilots I’ve had the privilege to fly with, Rod beamed with a love for flying. I met Haley at a group fly-in camping trip shortly after, and she’d already logged hundreds of flight hours at just a few years older than myself. Needless to say, I was impressed. Over the coming months, I visited Rod and Haley every few months. They helped me train for a tailwheel certificate, learn to fly seaplanes, fly a King Air to Nicaragua, and more importantly, shared that many of the best experiences in aviation are flown outside of airlines. Rod and Haley share a beautiful family today and years later I’m still making visits to Gulf Shores to spend time with them where we first met.
That single flight and our shared love for beautiful aircraft footage kicked off a friendship with Rod and Haley that helped start my YouTube career. Years later, we’d fly together as a flight crew for Mokulele Airlines, Hawaii.
University of North Dakota Aerospace (Part 141)
How does a kid from Virginia end up in North Dakota? After visiting, it didn’t take much convincing. My two business partners from Boldmethod, Aleks and Colin, are both UND graduates and set up a school visit during my senior year of high school. I’m not going to lie, I was a little nervous because North Dakota wasn’t exactly familiar territory. But almost instantly, I knew UND was the right place for me. The professors and students I met made me feel right at home and the training capabilities of the school were impressive. Plus, they clearly knew how to kickstart pilot careers, with more than 13,000 professional pilot graduates. Sure, it was already 30 degrees in October but I was excited to apply.
In 2015, I started my freshman year of school with a major in Commercial Aviation, which is a Bachelor of Science in Aeronautical Science. Yes, it was very cold. But I figured if my classmates from Hawaii and California could do it, so could I. Over the next 3 years, I had the time of my life. UND is a great option if you’re considering a collegiate aviation program. It has a big-school feel without being overwhelming, fierce loyalty, and a love for hockey that quickly rubbed off on me. The cost… UND is one of the most affordable college aviation programs you can find. After 12 months of living in the state, you automatically qualify for residency and instate tuition, which is a staggeringly low rate of under $10,000 per year. Of course, that’s tuition and doesn’t include flight training.
I graduated in 2018 after three years, with my ratings and CFII certificate in hand. That was possible due to a combination of AP credits and staying over summer semesters to accelerate my flight training. Today, UND Aerospace has grown to nearly 100 airplanes in Grand Forks, ND, alone. It has numerous career pathways for students with some of the best airlines in the country.
How I Reached 500 Flight Hours
Hitting 500 flight hours is one of the trickiest challenges for new pilots. It’s a threshold that makes you significantly more competitive to be hired flying for Part 135 air carriers, charter companies, and more. I had about 500 hours when I was hired by Mokulele Airlines as a First Officer, which is something I’ll talk about next.
Like many pilots, I flew anything I could find to build hours. Let’s just say I paid for a lot of avgas. Here’s a rough breakdown of what got me there:
200 Hours: Flight Training Courses (through CFII)
150 Hours: Ferry Flights, Part 91 King Air Flying, Cirrus Training (Rod & Haley, Boldmethod)
50 Hours: Shared C172 Aircraft Dry-Lease with Friends
50 Hours: EAA Young Eagles Flying
50 Hours: Fun Flights via Aircraft Rental
Did I mention building hours can be a lot of fun? The rush to build hours can feel like a lot of pressure, so make sure to slow down every now and then and just enjoy the fact that you’re now a pilot. Here’s one way we did that at the University of North Dakota…
Mokulele Airlines, Hawaii (Part 135)
Before starting my “traditional” career as an airline pilot, I wanted to experience some sort of adventure. I considered jobs like bush flying in Alaska or scenic tours over the Grand Canyon. Rod and Haley, the two friends discussed above, had just started flying as Captains for a little company in Hawaii, Mokulele Airlines. During spring break of my junior year at UND, I bought a ticket to Hawaii to visit them, meet their chief pilot, and see what I could do to fly there too.
Mokulele Airlines was an incredible way to start my career. Owned by Southern Airways Express today, it flies as a Scheduled Part 135 Air Carrier between the Hawaiian Islands in 9-passenger Cessna Grand Caravans. You’ll find a huge range of pilots at Mokulele, from 19-year-olds with a wet CPL to airline captains that retired years ago flying the 747 (there’s no mandatory retirement age at Part 135 carriers). The flying is beautiful and challenging, with up to 8 legs a day. Mokulele has all the pieces of a larger airline: gate agents, ramp agents, dispatch, strict operating policies, passengers, etc… Just on a really small scale. Couple that amazing flying with the adventure of living in Hawaii, and I was hooked.
While I had the qualifications to fly for Mokulele, I needed to finish one more year of school at UND. To be competitive for the job when I was hired, most applicants had about 500 hours (although I met a few with just 250 hours, their single-engine commercial pilot certificate, and an instrument rating). During my meeting with the chief pilot, we talked about my flight experience and goals with social media. I knew that the story of Mokulele needed to be shared with the world, and he agreed. We worked with our FAA-assigned airline inspector on procedures and restrictions for filming in a Part 135 environment.
At the time, Mokulele allowed part-time pilots to be on staff, so we worked out a plan. I would fly a summer season in Hawaii full-time before becoming a part-time pilot commuting from North Dakota to Hawaii during my senior year. Crazy, right? Commuting from North Dakota to Hawaii! Mokulele pilots have reciprocal jumpseat agreements with dozens of airlines, making it possible to fly all over the world cost-free. During my senior year, I arranged my classes in a Tuesday-Thursday block so that I could commute to Hawaii every other weekend. It was a big adventure being just 20 years old and helped me graduate with my R-ATP flight hours. I’m not sure if this same part-time opportunity exists under their new management structure.
I’ll always remember the time I spent flying for Mokulele as one of the best parts of my life. The lifelong friends I made have all moved on to their dream jobs, and I’m lucky to fly with a few of them at United Airlines today.
Envoy Air (Part 121)
To gain Part 121 airline experience in jets, the next step of my career was to start applying for regional airlines. Envoy Air was one of the first on my list. A regional airline owned and operated by American Airlines, Envoy offered the “career insurance” plan of a flowthrough to American Airlines. At the time, it was one of the only airlines offering guaranteed career progression to a major airline. Knowing that the airline industry was subject to massive downturns, this was a good opportunity. Today, most regional airlines have a career progression agreement with a major carrier.
At 21 years old, I started flying for Envoy as a LaGuardia-based Embraer 145 First Officer. After a few months, I transferred to Chicago, my final base at Envoy. At the time, the E-145 had the biggest network of any Envoy fleet. Our routes touched all four bases (LGA, ORD, DFW, MIA) and flying legs were as short as 20 minutes to as long as 3 hours.
Using the portfolio of experienced gained at Mokulele, I worked with Flight Operations and the FAA to come up with procedures for filming a comprehensive view of an airline pilot career. Thanks to their support, we were able to film some of the first footage from the flight deck of a Part 121 carrier. The videos produced remain invaluable resources to pilots entering the airline world for the first time.
During my four years at Envoy, flying shifted towards the new E-175. Our E-145 routes became shorter and shorter, so flying 5-leg days became a lot more common. I probably never would have visited some of the small cities we flew to on the E-145, and a few remain all-time favorite overnights. Due to delays from COVID-19, the first Captain-upgrade opportunity came in the fall of 2021 and I was excited to begin flying from the left seat. I had just passed my Captain LOE Checkride and was flying Captain IOE trips when the biggest step of my career arrived.
United Airlines
In February 2022, I was invited to interview with United Airlines. To date, I’ve never prepared more for a single day than that interview, and it paid off. Beginning class in March, I found out that I’d start my United career flying the Boeing 757 and 767. I’m humbled to fly this legendary plane so young and can’t wait to see what adventures are ahead. United shares my passion for supporting aspiring pilots from the very beginning of their careers, and that’s one of the reasons I’m so excited to be here.
United Airlines is growing by hundreds of airplanes, and to fill all of those flight decks we're going to need a lot of pilots. United Aviate is designed to train thousands of pilots, and open the doors of aviation to people from all backgrounds. It even has the only flight training school run by a major carrier in the USA. I’m thrilled to be a part of that mission. Simply put, being a pilot is for everyone. Diversifying the flight deck isn't just the right thing to do, it's the best way we can meet the world's demand for new pilots.
If you’ve ever dreamed of becoming a pilot, I’ve made it my mission to help you get there. Shoot me an email and let me know what I can do to help kickstart your aviation career!
