Post-Mortem: Terrain

Knowing the map isn't knowing the terrain

Dec 05, 2024

For anyone new, Terrain was the edtech startup that we launched during the pandemic. It’ll always hold a special place in my heart as one of the most meaningful projects I’ve ever worked on. Especially now that it’s found a new home.

TL:DR on Terrain

Terrain was an online learning platform targeting entrepreneurs, primarily digital service providers earning less than $50,000 a year who were looking to start or scale their online business. Our value prop was high quality, bite-sized courses that you’d actually finish. The industry average is only 10% of people complete online courses, our average was 67%.

The Origin of Terrain

First things first, the thing you've got to know about Terrain is that it stemmed from a problem that we were seeing in the industry. With The Scribesmith, we were working with a lot of people in the online creator space who were developing these online courses.

I had a team at this point, so I was buying courses for the team, and I was taking courses myself to grow. What we were realising was that most courses were crap.

Identifying the Problem

We took a first-principles approach and tried to identify what the problem was, what was wrong, and really tried to understand how we got to a situation where only one in ten people were actually completing these online courses.

We started by signing up and using other platforms on the market. We tried the self-hosted courses found on independent platforms—the ones with no quality control that merely sell you internet real estate to set up shop on.

Then there was the marketplace model, where courses are hosted on platforms like Udemy and Domestika. We used these platforms, conducted tons of user interviews, and read an array of journal articles (I'm going to link some of them at the end of this article). We set out to understand where the problem really was and started prototyping solutions.

Key Discoveries

What we discovered was that the problem was multifaceted.

Quality Control Problems

There was a massive quality control problem because there were no real barriers to entry for teaching. Anybody and everybody could sign up for one of these platforms, create a course, and market the hell out of it. They could even hire very good marketers (like our team) to sell these courses for them.

The issue? A large chunk of these courses weren’t actually teaching people anything. Sometimes, the testimonials were for other products, or were outdated, or for one-on-one services but were being portrayed as linked to the courses. There was a lot of bait and switch happening, and a lot of these courses were just superficial, repurposing other people’s content.

The most popular courses didn’t necessarily belong to the best experts in their field. It was a popularity contest—the most popular courses were the ones taught by the most famous person and the ones with the biggest marketing budget.

Misleading Practices

Another thing we saw was that a lot of people were using non-disparagement clauses. People could have negative experiences with these courses but couldn’t talk about them publicly. It was a deeply, deeply broken industry.

User Interface Challenges

The user interfaces themselves were flawed. Attention spans are declining (as you probably know or have experienced yourself). The average person doesn’t have the time to sit through boring monologues or hour-long videos. People need quick, concise, applicable content.

Rethinking Video Courses

One of the things we frequently questioned was whether video courses were the right medium at all. Personally, I don’t enjoy video courses. For most people, they seem to be the most effective way to learn, but they don’t work for everyone.

To address this, we tried to balance our offering by including full transcripts and additional resources with our courses. This allowed people to consume the material in different ways, catering to various learning styles. We also incorporated features like discussion groups to accommodate the needs of different types of learners.

Questioning Metrics: Completion Rates vs Knowledge Retention

Another question we kept revisiting was whether course completion rates were truly meaningful metrics. While they were still a big part of our marketing and something we tracked closely, I’ve always felt that knowledge retention is a more important measure of success.

The challenge was that we never really found an effective way to measure retention without building a testing mechanism, which we didn’t want to do. It was particularly tricky in a business context. How do you objectively test the kind of skills we were teaching?

For example, you could test someone’s knowledge of email marketing tactics, but is it valuable to objectively measure their copywriting skills? A test might not capture the nuances of effective learning or skill development in areas like business and communication.

If I were building Terrain now, given how far AI has come, I’d probably include a testing mechanism powered by bots. These bots could evaluate a learner’s understanding of the material using the rubrics we created. They could also assess how much people were actually learning, providing a more accurate measure of retention and application.

Such an approach would allow us to track learning outcomes in a more meaningful way, without burdening the learner with traditional assessments. It would also provide course creators and learners with actionable insights into the effectiveness of their learning journey.

The Philosophy

The name Terrain comes from one of my favourite concepts by Polish-American scientist and philosopher Alfred Korzybski, “The map is not the territory.”

The map–territory relation is about the difference between an object and the representation of that object—like a map versus the actual geographical territory it’s supposed to represent. Mistaking the map for the territory is a classic logical fallacy. It happens when someone confuses the meaning of a term with the actual thing it’s describing.

Korzybski’s point was simple: an abstraction or reaction to something isn’t the thing itself. Yet, people constantly mix up their mental models of reality with reality itself.

When it comes to online learning, so many courses on the market were excessively prescriptive: they laid it out step by step, “do exactly what I did and you’ll get results like me”, or “if I can do it, you can too” and I saw those as a by-product of that same fallacy. In my opinion, it was far more valuable to teach people to think about business and marketing critically than give them a set of steps to follow which only work ceteris paribus.

Learning Like Lego

I’ve also always been personally inspired by the concept of Lego. To me, learning shouldn’t feel like a chore. Learning is play—it’s intellectual curiosity, engagement, and the ability to expand your horizons. The saddest thing a person can lack is intellectual curiosity.

This philosophy shaped Terrain's core values. Learning on Terrain was bite-sized, modular, and compounding, in the sense that it built on itself—just like Lego.

All courses had a modular structure:

Every course was broken down into modules
Every module into lessons
Every lesson was a maximum of 10 minutes long, and came with some tangible steps people could implement in their business.

The Triple Win Philosophy

We wanted Terrain to deliver a triple win:

For learners – They gained actionable insights and knowledge to grow their businesses.
For course creators – They reached the right audience and had infrastructure support to deliver high-quality content.
For the planet – We incorporated sustainability by planting a tree for every course completed.

And a win for us, naturally.

Building Terrain

Asynchronous Learning

While everyone else was moving towards cohort-based courses, we chose asynchronous learning. It allowed people to learn on their own schedule, making it more flexible. This was a mistake. COVID was a time when people were lonely, and the structure and connection of cohort-based courses gave people the opportunity to connect better.

Gamification and TerrainCoin

Gamification was central to Terrain. We incorporated it in several ways:

Learners earned badges for achievements.
We had leaderboards and crypto integrations.

We created TerrainCoin, which learners earned based on points for positive behaviour. The value of TerrainCoin was tied to a percentage of our monthly revenue, which was divided based on the community's points. TerrainCoin was paid out in Ethereum.

Unique Features

Note-taking integration: The platform featured a video player on the left and a note taker on the right, so users didn’t have to switch tabs. Notes could be exported to Terrain’s notebook, Google Docs, or Notion, or synced with tools like Trello or Asana.
Smart transcripts: Text displayed on the screen as the video played (similar to the feature YouTube added last year).
Google Chrome extension: This allowed users to pull YouTube videos into Terrain’s interface to keep everything in one place.
Dark mode: A simple but well-loved feature.
E-reader functionality: Users could read ebooks and take notes directly on Terrain.

Metaverse Community

We even experimented with a Metaverse community. We built a Hogwarts-inspired world for our users to use for events, to take courses, attend talks, host book club meetings, and more.

Business Model

We initially allowed one-off course purchases, where creators submitted their courses to Terrain. We later switched to a subscription model and began producing courses in-house.

However, the production was labour-intensive because AI tools weren’t as advanced then as they are today. This made creating high-quality courses much harder and more expensive.

Reflections and Lessons Learned

Product Strengths

I’m proud of what we built. It was an intellectually meaningful project, and we provided scholarships, built a community, and created something special. The team upskilled rapidly—our designer was originally a social media manager, and everyone learned new skills to make Terrain possible.

We built fast and iterated faster, relying on data from user behaviour rather than opinions from interviews. While unconventional, it allowed us to create and improve quickly.

Product Weaknesses

Community: We didn’t invest enough in community-building, which requires a full-time manager. As the founder, I wore too many hats. I was deeply involved in every aspect, from product development to marketing, which limited my ability to focus on specific areas like community-building.
Community management, in particular, requires dedicated effort. It’s not something you can do halfway, and I didn’t have the bandwidth to commit fully to it.
Design: While functional, the design could have been slicker. I often prioritised functionality over form.
Timing: AI advancements today would have made production much easier.

One of the challenges I faced as a founder was my tendency to lean too heavily on my core competencies. Looking back, I wish I had invested more energy into areas that I wasn’t necessarily excited about working on—particularly design.

People are visual creatures, and while you can have really interesting ideas or content, if it doesn’t look polished, people won’t take it seriously. If I were to do it all again, I would invest heavily in design from the outset.

Bootstrapping and Team Size

The decision to bootstrap the business came equally from two places: not knowing how to raise funds and a reluctance to give up control and divert my attention from building and running the product toward raising funds. I’m not sure how well-founded those fears were or whether I’d approach things differently now, but having more funding would certainly have helped.

For one, we could have afforded a bigger team. At the time, we were setting incredibly ambitious goals, but there simply weren’t enough hands to execute everything. Everyone, including me, was stretched thin.

Pushing Every Hour to the Limit

I was also operating under the belief that if I had 24 hours in a day, every single one of those hours had to be purpose driven. While this mindset allowed us to achieve an incredible amount in a short time, it was absolutely exhausting. I’ve spoken about this before, but it’s worth reiterating.

Learning and Agility

Despite the challenges, we learned so much. Building Terrain often felt like building at the speed of thought. I vividly remember times when we’d give demos to potential customers, and they’d suggest a feature or improvement. Before the call ended, I’d have built the feature and presented it to them.

That level of agility we had was honestly pretty extraordinary and set us apart. However, the downside of such agility is that we ended up being a bit like a squirrel with ADHD—a very competent squirrel, but still easily pulled in too many directions.

It’s ironic when I think about it: We built Terrain to be this distraction-free, focused space for learning. And yet, as the founder, I often struggled with staying focused myself.

As they say, hindsight is 20/20. While there are many things I’d do differently—invest in design, avoid overcommitting, hiring a little differently, and consider raising funds—I still marvel at what we accomplished. We learned, we built, and we adapted at a speed I’ll always be proud of.

Thinking in Public

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