They were also incentivised to stuff as many new features into their products in order to make them look like they were worth upgrading.

Look at how bad Adobe Acrobat got before they even started thinking about subscriptions.

If you have a product and a team working on it, it’s tempting to just keep adding things to the product. You can’t just sit around fixing bugs, they say. When that is precisely what customers would want. Can’t make upsells though and when you’re a business that kind of thing really matters… nobody from within can see that the ship is so heavy it can’t stay afloat anymore. Until it’s sunk.