A valuable lesson I learned from @dhh was: never put your customer back in a buying position[^1]. For example, if you discontinue your legacy[^2] 1.0 product, and force them to switch to your shiny/better/faster 2.0 product, when 1.0 was working just fine for them, you are forcing them back into a buying position. And this time, they might choose your competitor.
Chrome was way ahead, but by overreaching against ad-blockers, they forced their users back in a buying position, and this time Firefox had gotten way better. Unless Google messed with the status quo, their users would never consider switching. The only thing pushing me toward Fastmail is that Google keeps messing with Gmail/Inbox.
This death-cycle seems to be unavoidable for MBA-types who inherit working products, and I bet you could build a business around this idea, or at least design a consistent enterprise takeover strategy.
Chrome was way ahead, but by overreaching against ad-blockers, they forced their users back in a buying position, and this time Firefox had gotten way better. Unless Google messed with the status quo, their users would never consider switching. The only thing pushing me toward Fastmail is that Google keeps messing with Gmail/Inbox.
This death-cycle seems to be unavoidable for MBA-types who inherit working products, and I bet you could build a business around this idea, or at least design a consistent enterprise takeover strategy.
[^1]: https://www.youtube.com/watch?v=CJkiCpPeYuI [^2]: Legacy = any code you can't (safely) change.