The advice might seem dated these days, but I think the stair step approach to bootstrapping is evergreen:
It’s much easier to sell an add-on to an existing ecosystem like a WordPress plugin, a Shopify app, a Heroku add-on – they’re usually small things to build, relatively inexpensive for customers to purchase, and you have built in discovery through the plugin repository or app store. Other examples include Magento or Drupal add-ons, a Photoshop plugin, a WordPress theme, or an ebook or course.
These are all great examples for how to obviate marketing as a huge concern for a first product, but they also share a certain sense of finality that a full-fledged SaaS rarely does. Once you've built the thing and added it to the marketing channel of choice, it is done (modulo minor going concerns like changes to the underlying ecosystem, version updates, et cetera.) It is very hard to spend too much tinkering around the margins on a fifty page book or a Shopify <> Helpscout connector, and that inability is a feature that gently nudges you onto greener pastures.
This is a circuitous path to my suggestion of a new genre of entry-level product for the prospective bootstrapper, which I will call the data product. Here are some examples:
- A beautiful and meticulous dossier for various iOS devices and their screen sizes
- A dense tabular UI to poke around various AWS instance prices
- An even denser tabular UI to poke around SSD prices
These projects have many merits: they are small in scope, require few engineering decisions that could cause an otherwise well-intentioned engineer to bikeshed, easily marketable, and lend themselves to expansion into adjacent products.
