Six months ago I launched a platform I had developed to deliver free online training on computing and security fundamentals. As of today, Roppers Academy has 400 registered students and is averaging 40 new users a week (Detailed post on metrics is in progress).

During the last six months, I have done just about everything wrong in terms of running a startup I can imagine, but this story does not start six months ago. Instead, this story starts back in 2015, because I spent four years making the single worst decision anyone can make when doing anything… waiting for the product to be perfect.

It began back in college, where I was assigned to be the training officer for my school’s competitive cyber security team. I was faced with a challenge: How do you train a large number of newcomers without taking up all of the time of the more advanced members?

Boat School Cyber Security Team, Cyber Defense Exercise 2015

To do that, I decided that the team needed a curriculum that placed a new student on railroad tracks, gave them exactly what they needed to learn and how to learn it, and then the only thing the teachers would have to provide would be answering questions.

Easier said than done.

I started with the simple part, creating the list of topics that I wanted students to learn. Then I went and looked for the best resources on the subjects. Then I found more things that I wanted to teach. This cycle lasted for two years.

Hindsight 1: There is infinite information on the internet, and new stuff is being created every day. Trying to be on the cutting edge and reading every article/list/resource that comes out is not making you or your material better, you are procrastinating. Worry about incremental progress once you have Pareto principle’d everything on your to do list.

By the end of my time at school, I was sort of happy with the curriculum and was ready to get it to students. At this time it was sitting in a GitHub repo, mostly ready to go. After research into which platform I should use, I decided on using the Moodle LMS because it was open source and infinitely customizable.

Hindsight 2: Part 1: I could have had all of the material I made ready to go on a platform like Teachable in under a day. I did not need the control I believed I needed, and should have gotten my material out and to students as soon as possible.

With all the work left to do on making the Moodle platform suit my needs, life got in the way and I spent the next two years driving boats in San Diego. I used some of my free time to work on the project and fiddle around with content, but for the most part I was occupied.

Just about as good as it gets.

Finally I came back from my second deployment (Round 2: Ballistic Boogaloo) and started making the moves I needed to get this done.

I finally went and built the Moodle server. Personalizing and adding the courses took a long time, mostly because I kept trying to modify the curriculum on the fly, again the curse of never being done.

I also went and wrote a bunch of custom code to make the site do what I wanted it to do. Moodle, while an awesome platform, is not optimized for conversion of inbound traffic, so I put a ton of work into making that flow.

Hindsight 2: Part 2: This is the only part of my entire journey so far I am glad I did the way that I did. The control and insight I have over my student’s experiences are second to none. Preferably I would have started on Teachable and moved here once I had the time to do custom dev. If you are interested in owning your education platform, click here for more information.

Additionally, I didn’t like the way that the Moodle application looked, and didn’t want to change the core code too much, so I decided I needed to make a website to point at it.

Hindsight 3: I wasted, and continue to waste a ridiculous amount of time on this damn static website. I should have gone with a sitebuilder like Wix or Squarespace from day one. The site in its current state is not professional or well designed, and figuring out front end dev has been hell. I am writing my blog post in HTML right now like some sort of animal, and next I will have to make a design decision on how to implement blog posts to the site. This is the definition of sunk cost fallacy, and I don’t expect to ever come up with a better idea.

Even with 150% of an actual product finished, I still hadn’t launched. At this point I felt very confident that I had the best course on the internet for teaching computing and security fundamentals, but I still did not have a single person registered. I had been working on this for about 7 months, and the material itself for 4+ years.

Completely unrelated to all this, I finally had an opportunity to transfer out of the boat driving side of the navy and into the Navy’s Cyber Warfare Engineer community, a highly technical developer program. I needed to spend the next few months preparing for the interview because I hadn’t done anything technical in years (don’t tell them), and if I didn’t launch the site right away, it was never going to happen.

So on Nov. 6th, not a day I chose for any real reason, I went and launched to my Twitter audience of 150 people I didn’t know and one Slack I participated in.

Hindsight 5: I barely used my Twitter before this (I still don’t, which will be a topic in a post about marketing) and I didn’t have a mailing list to email out to. If fact, I only created a mailing list the day after I launched. This is my first blog post ever. I am still learning my lesson on this, every day. If I had a mailing list and twitter followers growing for the last three years, I would have significantly more reach than now.

You might have noticed that I didn’t mention payment or pricing at any point, and I honestly really didn’t think about it at all. The course was always meant to be free, because I am cursed with the belief that information should be free and shared openly, especially foundational knowledge like this.

Hindsight 6: As much fun as it has been building this as community service, maintaining and operating it has not been easy going. I need to be making some sort of money to keep myself motivated to keep working on this, and should have added an option to pay, or at least donate, early in the game. I have a good job so money isn’t a priority, but it matters more for maintaining my motivation and keeping me focused on this project. I finally added a payment option last week for purchasing an instructor led course, but the main offerings will always be free.

So now for a wrap up of the first four years of the existence of this project, let’s go over where I went wrong again.

I spent too much time getting the material perfect, despite it being a finished course about a year in.

I didn’t believe any existing solution was good enough to host my vision, so I delayed making the material available anywhere for two years because of the work I still “needed” to do.

I did all the front end development for my website myself, despite having zero ability or design sense.

I launched to an audience of less than 300 people, of whom nobody cared about me or had any reason to listen.

I wanted to give the courses away for free, but didn’t realize that in order to have the motivation to maintain and improve the site, I would need to start making money once the initial fun was over. With a few different decisions I could have been hosting a course on a Teachable site, accepting payments, and growing my mailing list by the end of 2017. Instead… launch day finally arrived November 6, 2019.

Coming Soon: