After years of focusing solely on my main business Midstay, I recently started exploring some side projects again. Partly to hedge my current business, but also to test new ideas, tools, and services within the AI space.
But this time I am determined not to repeat my previous mistakes.
I have started on and built projects in the past where I was hopeful it could turn into something, but I was focusing on the wrong things, and they never got off the ground. Since my first project in 2018, I’ve gone from a “build it and they will come” mindset to a far more nuanced approach — one that prioritizes marketing and sales just as much as the product itself. From having 95% focus on building on my first project, I now don’t even want to think about building until I have obtained some kind of decent confidence in an idea.
The secret sauce for a bootstrapper and solopreneur is cheap validation, and having monetization and organic growth from the beginning. Even if I understood the importance of it, I still found it very hard to understand how to do this, probably because I’ve lacked even the most basic marketing and sales mindset.
In my previous attempt at launching a solo project, I knew these things, I tried to embrace them, but in the end I failed miserably at achieving even one of the three above-mentioned ingredien. This project was called Upmysurf, and was intended to be a marketplace for independent surf coaches, guides and photographers. There’s not really any good place to find vetted professionals in that space, so it seemed like a good idea, but there were so many reasons why this turned into a horrible experience for me. Why?
- I failed the initial validation: I started by trying to launch a simple landing page, and collecting some early interest and leads. This is well and good, but I didn’t really do any good keyword research, so I wasn’t able to drive any meaningful traffic to it. I tried running ads, but barely got any signups. And I gave up there.
- I built without validation: Instead of iterating on the initial validation until I was happy, I decided that I needed a product to “truly” assess the interest. In fact I was just trying to convince myself that it was ok to do what I was comfortable doing. I didn’t understand marketing, and I it was too uncomfortable for me to spend more time there. I thought I could instead launch an MVP quite fast, but as always, it took a lot more than expected.
- It was the wrong type of product: Since this was a marketplace, I knew that the chicken and egg problem would require a lot of early marketing, traffic and interest to have any chance of getting this thing off the ground. I kept building it and attempting to lay some weak-ass marketing plans as I went, but since this was still a side project, it became too overwhelming and I eventually ended up with a severe burnout and shut the whole thing down. I’ll probably expand more on that topic in a later blog post.
The experience really deterred me, and I haven’t launched any side projects since then, as I still haven’t had an answer for most of my failures. However, after seeing this video about the potential of web directories, I took the invitation down the rabbit hole, and I think I have found some answers.
If you don’t know exactly what a web directory is, it is basically a curated database of valuable data that people can visit to find information about a topic. They can be as basic as Craigslist, without other features than an index page and individual listing pages, or more advanced like IMDB or even turn into something more than that. The approach John Rush is talking about in the video made something click inside me, and I’ve decided it’s something I have to try. He lays it down in the following main steps
- Find your niche/directory topic through keyword research. Validate that you can compete on SEO from the beginning.
- Set up a basic directory without any sophisticated features. Just make sure the data is good enough.
- Leave it for 3 months, and come back to see the results.
- Only if you see enough interest, expand on the directory features and monetization routes.
So why did I find this approach so appealing? Well, first of all, you are starting with validation as your first step. You’re not even considering any topics that are too competitive or where there just isn’t enough public interest. Secondly, you don’t spend a lot of time building features no-one will use. Thirdly, if it succeeds to gain significant traffic, you now have a plethora of routes you can take.
It’s a lot more interesting building when you already have users and interest, and you can also start collecting feedback from the very beginning; only building out features that will actually be useful to your audience. All of these points are important, but it’s the last that gets me really excited. If you just want some steady, low-effort income, you can keep optimizing your data, SEO, ads/affiliate links, and leave it at that.
Or you can leverage this traffic to go big. Since you already have an audience, you can channel these users into a Saas or other products related to the topic. With Saas, marketing can be your biggest challenge, and here you’d already have a head start and minimize your risk to launch a new product. Another route to take is to develop your directory to its max potential. You can e.g. create a community and get high user engagement, which could really allow your profits to take off. The best part is that this can develop completely organically!
Lately, I’ve been deep in research — exploring different directories, assessing potential downsides as AI becomes more dominant, and digging into data collection strategies. However, I’ve also been scouting for the right niche to start with, and I think I’ve found one. I’ll share more on that in a future post.