The first thing I would say is that shareware (in the classic definition) is not really a thing anymore, but “try before you buy” software (which is really the evolution of shareware) is very much alive and well.
The second thing I would say is that most people would be surprised by how much some of these companies sell. Certainly not everyone does well, but we see small companies selling tens or hundreds of thousands (USD equivalent) per month. Some reach seven figures a month.
I can’t think of a single company that I’ve worked with that had VC-style funding. Most are bootstrapped with a small minority getting small “friends and family” investments.
It is still possible to make a lot of money with try-before-you-buy software. A few tips:
Don’t underprice. If you can provide enough value that they’ll pay something you’ve got more room in your price than you might think.
Feature limitations work better than time limitations.
75% of you sales come within one day of the trial download, and of those, 75% come within the first two hours. It’s important that the product conveys why and how to buy.
Don’t forget about other markets. In the early days most sales came from the US. These days, the US represents about half. When you get traction, consider translating your product and don’t forget to offer your product for sale using multiple currencies and payment methods. Third-party e-commerce platforms make this easy. They’ll also take care of a lot of the regulatory burden for you (taxes, export controls, fraud & chargebacks, etc.).
If your product is targeted at large companies, offer premium support for a fee. Something as simple as a “response by email within one business day” SLA can be enough.
SEO matters a lot in helping people find your product. High quality content about the problem your product solves helps a lot. In the early days find where people who need your solution are talking about their problem. Be transparent, offer genuine, non-spammy help as a solution expert and people will allow you to talk about your product. This can help a lot as you get established.
If someone will donate, they’ll buy. You’ll feel more benevolent asking for donations but you’ll make a lot more money if you sell the product. We’ve seen both models. It’s not even close.
If your product is not targeted to a highly-technical audience, open source might sound cool but means nothing to them. They won’t buy more because it’s open source.
I could go on and on. I’ve said enough but there is still plenty of opportunity here. It takes time - be patient. Most of the successful companies I know started as a side gig.