We help build the safest pilots.

It started with T-tails. As a kid, my family traveled by plane, and I can still picture the Delta flights clearly. I was fascinated by the T-tail jets, and I would spend hours comparing them to the newer fan jets, the conventional-wing airplanes that are everywhere now in the 737 and A320 families. It took me years to warm up to the fan jets. Even now, nostalgia sets in when a DC or MD T-tail goes by.

Before 9/11, my father worked in Airport Operations at Nashville’s KBNA, which meant he had connections with just about everyone who worked at that airport, and as a pre-teen I spent hours hanging around the terminal. The security people at the metal detectors knew me. The gate agents knew me. Regular crews knew me. I would be let onto airplanes and given drinks, snacks, and wings. Those moments left more of an impression than I realized at the time. Being around crews quietly settled something in me: I wanted to be in aviation. What I did not know yet was that I wanted to be a pilot, and nobody ever showed me a path. School did not present flying as an option. The paths laid out in front of me were theology, medicine, law. I fully pursued none of them.

I did start, though, the only way available to me. I was eighteen when my father connected me with the janitorial company at KBNA, and I was hired on the spot. I took it, and I liked it — not the work, but being around airplanes and people who loved them. The janitor job lasted less than six months, because it did what it was for: it put me in the building, around the people, and it led straight to my first real aviation job, customer service representative for SkyWest Airlines, the United Express carrier in Nashville. I thought I had made it. I learned everything I could from the former legacy United employees who had become SkyWest people when United pulled out of Nashville, leaving a satellite station — and that learning later accelerated everything. SkyWest moved me to San Diego, then to Birmingham. I wanted mainline. I networked, applied, flew to Chicago positive-space, aced the interview, and started at the bottom again: the KORD ticket counter. I loved it, until I didn’t. Every morning after the team huddle I watched agents head through security to work their gates, and the ticket counter stood between me and the flight crews — and the airplanes. People a few months in do not normally move from counter to gate at United; it takes months, sometimes years. I networked heavily, befriended the training team, and got my date. Gate training was a breeze — I had done the job at SkyWest and knew the legacy tools; I only had to learn the mainline procedures. I was issued my company BlackBerry, the thing gate assignments and irregular operations arrived on — and at O’Hare, irregular operations were the norm. I had made it. Or so I thought.

By then I had a family, living in Chicago on barely twenty dollars an hour. It was not enough, and that is what pulled me out of aviation and into technology. My tech career ran the same way my aviation one had, linear and fast: pay up, scope up, leadership honed and tested. Then it plateaued. In November 2023 I got the call — or rather, I saw the calendar invite first: my CTO and HR, and I knew exactly what it was before anyone spoke. I was working remotely from my home office in Lebanon, Tennessee; the family had a house in upstate New York because the job was based there, but Lebanon was home base. The call, on November 28, was cordial. I negotiated my settlement with HR, and that was it. The days that followed were the angry ones: furious, irritated, frustrated, all of it at once. Then, December 1, in the middle of the most ordinary errands imaginable — picking up a few small things at the Walgreens in Lebanon — HR called, and the money matters were finalized, my number agreed and approved. The papers came through DocuSign. By then I had crossed the street to the CVS, and I sat in the car, read the legalese, and signed my settlement on my phone. That phase of my life was officially over. What I did not expect was what the signing felt like: relief. I was free — free to decide about the upcoming vacation, free to travel, free to pursue something I did not yet know I had the option to pursue. The anger went with the signature. I have looked forward from that point and never looked back, carrying the lessons and the mistakes I will not repeat; a period of refinement, I call it. The settlement itself went into savings and helped carry the family — and, though I didn’t know it yet, it was also the first money that would get me flying.

Understand what I did not know, even then, after years working inside the airline industry. I did not know discovery flights existed. I did not know how a person becomes a pilot. I did not know there were flight schools. I assumed most pilots, if not all of them, came out of the military. I had never heard of general aviation. Every one of those things I learned only after the drone.

So: vacation. Puerto Rico, the family’s annual escape, at a moment when escape was genuinely needed. This trip was different because I brought a new toy, a 4K DJI drone, and I did it properly: researched it, registered it, earned my Part 107 certificate, half-thinking it might become an income source. It became an expensive endeavor instead. What it actually did arrived in the mail: an envelope from the FAA with a certificate card inside. My own certificate. And the card called me, Jerry, a pilot. That little Part 107 card is what opened the door to the fixed-wing pilot I am today.

January 2024: my first discovery flight, at thirty-seven years old, in a clapped-out Cessna 172. The sight of the little old airplane gave me pause — I was supposed to fly in that thing? I did my first walk-around with Vlad, probably one of the most demanding and thorough instructors I would ever fly with. Demanding. Safety first. Airspeed is life. More right rudder. Vlad shaped the pilot I became. Left seat, buckled in, run-up done, lined up on runway 15 at 20N, Kingston. I had never been in an airplane that small, never seen a runway from that angle, and the radio calls were a foreign language. Brakes off, rolling, airspeed alive, rotate — and the feeling was not joy, it was alarm. A few feet over the Kingston bridge, over the Hudson River, I was certain I should not be doing this and wanted to be back on the ground. I did not let Vlad see it. At cruise, Vlad handed me the controls. Straight and level. Climbs and descents. Then: want to try a stall? Sure, I said, having no idea what a stall was. When the nose dropped I thought we were dead. Somehow we landed. On the ground I was done — crazy, never again, not coming back. Then Vlad debriefed me, handed me my first logbook, filled out and signed, and I heard myself say I would see Vlad in February to start training. That was January 12, 2024. My second flight ever, and my first real training flight, was February 19, 2024. I never looked back. Several instructors have taught me since, each leaving things I will never forget, and the journey continues — I have since gone back to corporate technology, heading operations at an AI company, and I love flying more now than I did as a kid with my model airplanes. PilotPrep is where the decades of technology and business leadership meet that love.

Early on a foggy summer morning, flying from Morristown to Salisbury for a checkride day, I sat in the back of the airplane cramming. Another student was up front flying a practice instrument approach. Their instructor was in the right seat. I could fly the airplane. I had no doubt about the flying. What I had no clue about was the oral: the conversation waiting on the ground, the questions behind the questions, the examiner I had never met deciding whether I was a safe pilot.

That gap, between being able to fly and being able to show it, is where student pilots actually struggle. I have lived every hour of the long version since: first solo at Columbia County in May 2024, private checkride at Salisbury in June 2025, instrument checkride at Morristown in May 2026, 260 hours and counting, still training toward commercial in the margins of running businesses and a full-time job. Not a prodigy story. A working pilot’s story: early mornings, plates and weather and doubt, progress measured in tenths of hours.

The build started in early 2026, when I was head of enterprise operations for an AI consultancy. AI had made significant improvements — the vibe-coding wars were one of them — and I was about to get back to my joy: coding and building products. At first I was not very impressed with the quality of what the AI built, so I put my engineering hat on and did the work of telling it what to build for me, how to build it, how to design it, and what the behavior rules were — and I would have a nice product in very short order. The AI had taken over the job of writing code. It was not quite ready to do all things well on its own, but it had changed what one person could attempt.

I also had a successful online coffee business already running — the Coffee Bean Connoisseur — and the question formed: could AI let me actually bring to life more of the ideas I had? I had many ideas for businesses, but never the time to nurture, build, and test them. Now the build component was cared for; I just needed to sit down and think things through. Three ideas came immediately, and all three had the same theme: aviation. No surprise — aviation is a passion; I was now a pilot and a plane owner, deeply entrenched in the mission. The deeper I went, the more pilots I met, and the more I learned there are serious opportunities to help people. A significant portion of the population is afraid to fly — I had an idea for that. But my immediate focus was pilots: how to make aviation more accessible. Not diversification — access. Knowing that aviation is not some abstract dream that is unattainable. I had viewed it that way once myself; it is very attainable, if you know where to start.

I landed on helping pilots navigate the process of becoming a pilot — more specifically, the checkride. The anxiety around checkrides is hard to imagine until you have lived it, and the irony is that checkrides are a permanent part of a pilot’s life and career, so a pilot can spend a whole career in a recurring state of anxiety every time one comes around. Not every pilot, but the problem is real in the industry. The way to solve it early, I thought, starts with transparency: knowing what to expect. Cue PilotPrep. I thought it through deeply and started to build what I believed was the perfect solution for student pilots — a tool that would prepare them for the oral portion of the checkride. I did the customer and market research, and the idea held up: it’s great, do it, the market needs it.

So I built the first version. It was crude, but it worked. The mock DPE voice sounded robotic; it was, by all accounts, simply functional. Not pretty — no visual design thinking put into it at all — just a tool crudely built to test my hypothesis. It proved my point: I could do it. The first thing I did then was call a CFI friend and tell him what I had built. The friend was skeptical, but he said this was a need, and if you get it right it could be big. He was still skeptical. If you know me, skepticism is all I need to prove it can be done. Now the mission had motivation.

Then came the flatline — and in my telling it was not a market that ignored the tool; it was the builder who walked away from it. Just as a cat is distracted by shiny things, I was distracted by wanting to start developing another idea immediately, and so I did: a second full product, this one to solve pilots’ issues with finding low-hour jobs. In the United States, the FAA requires pilots to gain 1,500 flight hours, with limited exceptions, to qualify as an ATP. Jobs for Part 91 and Part 135 can be word of mouth, sporadically placed on job boards, or just seemingly non-existent. It was a mission I was proud to support, because it would soon deeply impact me: even though I have a plane, I wanted options, and a flying gig — contract or permanent — would have been that answer. I created the tool that would help me and countless other pilots. What I learned is that I had completely left the development and go-to-market efforts on PilotPrep to focus on the new idea, and it was a doozy. I quickly built out the prototype, but getting a consistent, reliable, and differentiated list of low-hour jobs proved difficult — not impossible, but difficult. I was determined to make it work. Months passed, much work was done, but no product was fully completed and launched.

I decided to take a break. I traveled; my wife and I met up with friends — and that was all it took to get me back into my treasure trove of ideas that needed to be built and made available to the public. This time the idea of helping people who are deathly afraid of flying resurfaced: they have a friend who flies, but is an anxious flier. That meeting of minds led me to go home and quickly pivot to develop this new idea, which would turn into a new app and product entirely. Now I had three ideas, three products, three brands, potentially three companies in various stages of completeness, none of which were fully launched — all of them really great, if I could get them out. The reality is, I was one man, still with a family, a full-time job, and other really important responsibilities, not to mention a pilot who needs to fly. Something had to give.

So I sat and really thought about what to do next. Of the three ideas, which had the most potential to launch quickest and allow me the time to market it and get it to maintenance and support mode with minimal effort? I decided I needed to focus on PilotPrep — of the three products, it was the closest to being market ready. The race was on. I knew what I needed to do: purchase the domain; find out how to incorporate it into a company, or fold it into an existing company; I needed a marketer (cue my wife); I needed to do more market and deeper customer research — who would I target? So many questions to answer, all while polishing the design, replacing the robotic-sounding voice, and figuring out pricing and feature gating. If anyone tells you starting a company is easy, they are lying. This was work. Even with AI, it was work: AI helped with the mundane things, but even AI needed a manager — a babysitter, even — to ensure it kept pace. To be honest, it is amazing what AI has learned from humans: it can be cranky, slow, and worst of all downright lazy at times. Alas, all was, to my standards, complete and ready to hit the market.

It was early summer that I enabled the domain, swapped the DNS entries, and set PilotPrep live into the world. For a few months I had great traction and usage of the tool; it validated that this is a tool pilots needed and would use. I had paying users. Success! But I had a nagging feeling the tool could do more. I did not know what more I wanted it to do, and I did not want to copy what others had already done; I have always wanted to build a tool that is unique and solves real problems. I knew I needed to get the tool into the hands of the very people the tool was emulating — the DPEs. So I began DPE outreach. A few responded, and provided great feedback. One DPE in particular took time and helped me answer the question of what more this tool could do.

That DPE was Ryan Davis. I share the last name, and took to calling him DPE Davis. The conversation ran a bit over thirty minutes — aviation and tech, and you could tell both of us loved to talk about both, and that we were both deeply interested in helping build the safest of pilots. I had consulted with him, and out of that conversation I decided to build out new features and train the AI differently — and the conversation answered the nagging question of what more the tool could do.

The answer clarified what the product was for. Not passing a test. Building pilots who understand the material well enough to use it on a real flight, in real weather, with real consequences. Pilots who are safe because they got past memorization. And the diagnosis underneath it was the same one a good instructor gives a stuck student: you are practicing the wrong thing. Pilot training is all about memorization — but pilots who simply memorize facts, weights, and speeds are not safe pilots. PilotPrep had been built for the last two weeks of training, the checkride crunch, asking brand-new visitors to start with the hardest, scariest part. Students do not need a simulated exam on day one. They need help with Tuesday’s lesson. The tool had the sequence backwards, the way a student who memorizes answers has the learning backward.

That is why I made a business decision that, by all accounts, seems counterintuitive for a for-profit company: the largest feature of PilotPrep would live up to the name — prepare pilots to be safe pilots — by providing free course material for the private, instrument, and commercial ratings. It even goes a step further: it helps the CFIs who are instilling safe thinking into future pilots, giving them access to create, edit, and share pre-made curriculum. Those CFIs are able to get their students on PilotPrep for free, connect with them for free, and see their progress, their weak areas, and ultimately their readiness for the checkride. PilotPrep has never been about making money; it has been about solving problems that pilots experience. Could I gate the training courses and charge for them? Absolutely. But why? It goes against the mission of building safe pilots. The reality is yes, money is needed to sustain the site — but money is not the mission. Safety is.

So PilotPrep became what its name always said: preparation, for the whole journey. Free training for every lesson an instructor assigns, teach it, train it out loud, and only then prove it in the oral. A CFI in your pocket for the nights your CFI is not with you. Built and refined in consultation with a working DPE. Still built by a pilot who is, himself, still training.