How Dan George built a 10,000+ student flight school with Teachable

Dan George was a professional pilot and flight instructor who hit a wall.

He taught ground school theory to aspiring aviators one-on-one and in small classroom settings. 

His work covered regulations, weather theory, aircraft systems, and more. Everything pilots need on the ground to be able to fly planes safely.

There was just one problem. The aviation industry was starved for more quality training, but Dan could only reach local students who showed up in person.

At any given time, he had maybe a few dozen students. Dan needed a more scalable model to be able to reach and impact the aviation industry with his expertise.

That's not a business model you can use to serve an entire industry.

Related: How to make money selling courses right now

Dan’s Teachable journey at a glance

The turning point

Dan created his first course on Teachable in 2019, but he didn't push it seriously for almost two years. It existed more as a side project than a real business.

The pandemic changed everything. With commercial flying disrupted and more time on his hands, Dan decided to get serious about online education in 2021.

"You could almost argue that that's when the business started was 2021, even though the relationship with Teachable has gone back to 2019." -Dan George, Founder and CEO at FlightInsight

Dan chose Teachable because he needed something simple that would let him focus on teaching rather than technology. He'd seen other successful creators on the platform and noticed they all followed a similar playbook: build your audience first, then convert that trust into course sales.

"The first thing that I learned about Teachable creators who have had success is that we all kind of have the same model. You build up your following and then you leverage that to start bringing people into a course." -Dan George, Founder and CEO at FlightInsight

Dan's secret sauce to success on Teachable

Dan didn't reinvent online education. He just did the fundamentals really well. His approach was methodical: Build trust first, deliver real value, and never stop showing up. 

While other creators chased quick wins, Dan played the long game. Here's how he turned consistent effort into a business that serves thousands of pilots worldwide.

Strategy 1: Build your audience before selling anything

Dan spent six months in 2021 creating valuable YouTube content without promoting his courses at all. He established a rigid publishing schedule that he's maintained for four straight years.

Twice a week, every Tuesday and Friday, without fail.

"It's been the same cadence for four years now. Twice a week, Tuesdays and Fridays." -Dan George, Founder and CEO at FlightInsight

His content strategy was simple: teach what pilots actually need to know. He covered instrument approaches, aircraft setup procedures, and regulatory updates. Real instructional content that people were already searching for.

The key was consistency over perfection. Dan didn't try to go viral or chase trending topics. He focused on being genuinely useful to his specific audience before asking them to buy anything.

"It was just a matter of just doing it, right? Just commit to two videos a week, make it very formulaic, get good at what you do and sort of stay in that box." -Dan George, Founder and CEO at FlightInsight

Take action: Pick a content schedule you can maintain for years, not months. Dan's success came from showing up consistently with valuable content before asking for anything in return.

Strategy 2: Use your teaching expertise to create standout content

Dan had a big advantage: he knew exactly what pilots needed to learn because aviation training requirements are standardized by the FAA. But he put his own spin on the material to make it actually stick.

He developed two main content approaches that set him apart from existing training materials. First was what he calls "advanced whiteboard" - taking dry regulatory charts and bringing them to life with animations.

"We'll take like a figure on a publication like a chart and we'll impose it onto either another chart or onto something that's situational in an aircraft to say okay this is where this is coming from so that the user can track where a principle comes from point to point to point." -Dan George, Founder and CEO at FlightInsight

His second approach used flight simulator footage to create controlled learning environments. Instead of filming in actual aircraft with all the distractions, he could control every variable in the simulator.

"Rather than actually showing people what it looks like in an aircraft and having to film in an aircraft and deal with all the distractions that that does, we control the environment by being in the simulator. You can control the weather, you can control the position, everything about the aircraft." -Dan George, Founder and CEO at FlightInsight

Take action: If you're teaching standardized material, find ways to make it more visual and connected. Show how different concepts link together rather than teaching them in isolation.

Strategy 3: Go deeper than your competition

Dan's biggest frustration with existing aviation training materials became his competitive advantage: they didn't go deep enough.

"It just didn't go in depth enough." -Dan George, Founder and CEO at FlightInsight

His paid courses go significantly deeper than his free content, providing comprehensive training that prepares students for real-world flying situations, not just passing tests.

When he launched his third course, something important happened that validated his approach: massive repeat business.

"One of the first sort of great little pieces of data that we got when we launched our third course was that we got so much repeat business. There are ways you can optimize that with lifetime value by giving people upgrade offers to get all our courses and things like that." -Dan George, Founder and CEO at FlightInsight

Students who completed one course immediately enrolled in the next level, creating a natural progression path through different aviation ratings.

Take action: Don't just create courses that check boxes. Go deeper than your competitors to create genuine expertise and transformation in your students.

Strategy 4: Choose courses over coaching for real scale

Dan considered offering one-on-one coaching but made a deliberate choice to focus on self-paced courses instead.

"I've toyed with doing coaching. I just don't know that it scales like a course scales." -Dan George, Founder and CEO at FlightInsight

His courses work around the clock without him being present. Students from different time zones can learn whenever they want. Adding more students doesn't automatically mean more work for Dan.

This decision freed him from the time-for-money trap that had limited his in-person instruction business.

Take action: If you want true scale, design your courses to work without your constant involvement. Include everything students need to succeed independently.

Strategy 5: Let organic content do your marketing

Dan tested paid advertising but quickly discovered it wasn't worth the effort in his specialized market.

"We turn on ads and they kind of run, maybe they break even, maybe they're a little bit profitable, but you realize that organic is your main bread." -Dan George, Founder and CEO at FlightInsight

This makes perfect sense for aviation. Pilots research thoroughly before investing in training. They trust instructors they've followed over time much more than random advertisements.

Dan's organic approach had an unexpected bonus: it attracted flight schools who wanted to partner with him. His social media presence became a powerful business development tool.

Take action: In specialized markets, consistent valuable content often beats paid advertising. Focus on building genuine trust and authority in your field.

Dan's results on Teachable

Dan's transformation shows what happens when you combine deep subject matter expertise with the right online education platform and consistent execution.

Starting with just a few dozen local students, he now serves over 10,000 pilots worldwide through eight Teachable courses. His four main ground school courses cover private, instrument, commercial, and flight instructor ratings, each priced at $229 for lifetime access.

"We have eight courses. There are four what is called ground schools. So that would be private, instrument, commercial and flight instructor. Those are $229 each for lifetime access." -Dan George, Founder and CEO at FlightInsight

The smaller ancillary courses cover specific skills like radio communications, landing techniques, and advanced avionics, ranging from $129 to $197.

His growth is particularly impressive considering aviation's limited market size. With only 400,000 pilots in the United States, Dan's school now serves a significant portion of the entire industry.

Expert corner: How Dan thinks as an educator

Dan's systematic teaching approach helps pilots understand not just the "what" but the "why" behind aviation procedures. His visual methods make complex concepts finally click for students who struggled with traditional textbook-based instruction.

The ripple effect extends throughout the aviation industry. Better-prepared pilots mean safer flights, more efficient training programs, and higher success rates on official FAA examinations.

His courses particularly help international students who struggle with American aviation procedures and FAA regulations, providing clear explanations that bridge language and cultural gaps.

Looking ahead

Dan's main focus is what he calls growing his "funnel" - continuing to build his audience and convert that trust into course enrollments.

"That's basically what my job is now is to just kind of try to make that funnel bigger." -Dan George, Founder and CEO at FlightInsight

As the aviation industry evolves, Dan sees opportunities to create courses on emerging topics while maintaining the depth and quality that built his reputation.

What to do next

Check out Flight Insight's aviation ground school courses on Teachable. Dan's systematic approach is helping create safer, more competent pilots worldwide.

Try Teachable yourself: Ready to scale your expertise like Dan? Start your free Teachable trial today and join the creators who use Teachable to build successful online education businesses.