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Pilot Story: Caleb Webb

  1. Home
  2. Pilot Story: Caleb Webb
Pilot Story: Caleb Webb
Drone Ops Solution 728x90

22 January 2025

By Caleb Webb

As a young person, I really never was sure what I wanted to do as I got older. I had a lot of ideas, but as a kid with a short attention span and a variety of hobbies that I liked to do, I changed my mind quite a bit. I’ve had so many hobbies over the years, it is really not funny. From amateur radio to triathlon, I’ve been quite an active young person. Fast forward a number of years: I’m 19 years old now, and owner of a slowly growing aerial photography company in New Hampshire. But how in the world did I get into flying drones? 

I remember always liking RC vehicles, helicopters, and planes. I remember having one old RC truck that I recall having quite a bit of fun with. But I especially liked the little helicopters. The first one I can remember in the house was a little green helicopter. I was probably too little to fly it, as I have no recollection of myself flying it. I think one of my family members ended up crashing it. A few years later, I remember buying my brother a little better RC helicopter, and soon thereafter, he got me one. Mine was red with a red and blue flashing light on the front of it. It took forever to charge and had about a 5–6-minute battery life at best. I remember having a lot of enjoyment with that. 

Fast forward another few years. My brother and I were older, and one of my brother’s dreams had been to fly real airplanes. Ever since he was little, he had a love for aviation. And so, at 18, my brother began to take flying lessons. This is where I was really introduced to aviation. 

Around this same time, my brother got me a little quadcopter for Christmas (which, by the way, I still have). This was my first “drone.” It had a little camera with no gimbal on the front, and a positioning camera on the bottom. It had an app that could be connected to a phone to have a live view, and had a battery life of about 8 minutes. I remember flying it around the house. I thought it was so cool, but it was very hard to fly, as the positioning system was terrible on it, and it had a tendency to drift a lot. It was almost impossible to fly and turn the drone without hitting something. I remember the first time I flew it outside. I flew it straight up about maybe 50 feet, did a few flips, and then brought it down and landed it on the beach, where I got sand in the motors. 

Now during this time, my brother had gotten his private pilot’s license and was working towards his instrument rating. But in the meantime, one of his flight instructors recommended that he get his Part 107 drone license. For an already licensed airplane pilot, it was really easy: an open book test. I guess they figure you already know a lot of the rules of the airspace and so on. So, he got his license. I remember my dad talking with him and looking at drones and discussing with him the possibility of flying a drone for money. However, that never went anywhere. He was far more interested in manned aviation. However, it was about this time that I started looking at the Part 107 and thinking, “Hmmm...that is cool. I’d love to do that.” I also read that I only had to be 16 to get my Part 107. I decided that is what I wanted to do: start an aerial photography service. 

So, I bought the 2022 study book and 2-year practice testing software license from ASA. I was 17 at the time. I began to study it, and was quite excited. However, I started to get busy. I was working in the summer, as well as developing as a runner, so I had a lot going on. And then my senior year of high school came. I was home schooled, and had a difficult and rigid curriculum. Just as a note: I am not complaining at all; I’m actually very thankful for the above average education I received, even though it was a lot of work. But, my drone studies kind of fell apart. I would look at the book and think, “Oh, I’ll study for that.” But then I never seemed to, except for rare occasions. I kept setting goals for myself to get my Part 107 license, but it just kept getting pushed farther and farther out. 

After graduation, I kind of just decided that I was going to get my license. I started studying again. Then I remembered that I had never activated my 2-year license. So, I hopped on the computer and did so. My first practice test I took, I believe I passed (although it was close). I couldn’t believe it. I took many more over until I was constantly passing them with good grades. I then decided that I was going to get my license ASAP. I only took the practice exams for about a month before I took my actual test. I remember being nervous as the instructor got the grade for the test, for I was worried I had failed. Thankfully, my hard work had paid off, and I passed with flying colors in October 2023. I pulled out that little quadcopter and took it outside. It was a little difficult, for the wind was a little too high for it. First, it blew into the neighbor’s yard; then, it nearly blew into my dad’s truck. So, I couldn’t use it outside.

In the meantime, I had been looking at what drone to buy. I was looking at the DJI Mini 3 Pro and Mini 4 Pro, as well as the DJI Air 3. I also ran across the Autel Robotics Evo II Pro and Yuneec Typhoon H+. But my dad and I were discussing what I should get, and the conclusion we came to was to buy a cheap drone to learn on. After all, we thought, if drones are as hard to fly as that quadcopter, I don’t want to be buying a thousand dollar drone and crashing it. So, to Walmart we went. 

I am happy to say that my first drone was not I what I was originally expecting to buy. I ended up buying a DJI Mini 2 SE. I absolutely loved that drone. Very user friendly, and at the time, I thought the camera was absolutely amazing. (You really can’t complain about it for the price.) Although, within a couple of months I realized I would need a better drone for higher quality YouTube videos and so on and the work that I was hoping to soon get. I ended up buying the Autel Evo II Pro V2. It isn’t the V3, but it is still an impressive drone. 

About the time I bought the Evo II Pro, I decided to form an LLC by the name of New England Aerial Photography, LLC. Combine the old-fashioned work ethic that my dad and grandfather instilled into me with my desire to work for myself, and I was determined to make it happen. I made a website, bought business cards, went around to realtors, made cold calls, and sent out emails. Unfortunately, there was really nothing solid from anybody. I got either no response, or they just said nice things to me, probably to make me feel better since I am young. But one chimney company did take me on. I remember my first job I did for them. I charged too little, but it was perfectly okay. That was the first $100 of my business. 

I ended up buying a regular camera for real estate, but I still got nothing. However, after talking to a close friend of mine who was a realtor, he said he would use me if I invested in a software called Matterport which does virtual 3D tours. He said it would be a couple thousand-dollar investment, which I was in no shape to do that at that time, even though I was working part-time. However, something came up. I found out that far cheaper Insta360 cameras are just as capable of performing Matterport tours as the expensive Matterport brand cameras.

I ended up buying an Insta360 One RS 1 for doing Matterport, and it has more than paid for itself. Sure enough, he took me on, and it really helped out when another friend of mine, who had been doing the drone work for my realtor friend, sold me his drone which was a DJI Mavic 3 Classic that had hardly been flown with a bunch of accessories for a very good price. My realtor friend has been using me ever since. The final drone I ended up buying was the Autel Evo Lite Enterprise 640T, which came out a few months ago. 

Well, to close out, I have had my ups and downs as I develop this business. I have had many frustrations. This business is far from supportive for me. I have to work another job, but they are very flexible, and allow me to take off whenever I need to, as my business is priority to me. It takes a lot of work and sweat, but I have confidence that my hard work is going to pay off. My ultimate goal is to work full time as a drone pilot. Nothing worthwhile ever came easy to anybody, and I believe that I am no exception. As of this writing I am currently planning on getting my thermal certification within the next couple of months (March 2025), and I look forward to the doors that that will open for me. 

I am willing to travel to complete a job. My goal is to provide the best possible product for the customer, while being safe, professional, honest, and FAA compliant. I currently use SkyWatch hourly drone insurance, which covers me up to $1,000,000 in liability. 

As an end note, I hope that this story has been interesting. Maybe there are other pilots reading this that are in my shoes. If so, keep up the good work, and don’t give up. It will pay off in the end if you stick with it. If you are an experienced drone pilot reading this and see areas where I can improve, PLEASE stop reading, go to my profile, get my contact information, and tell me where I can improve. I’m always open for tips and pointers on how to do better. 

Thank you so much for taking the time to read this. Here's to safe flying and clear skies!

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