Hi Chipp, yes you've definitely got it figured out!
One thing that's really problematic about the "must pile on features for this release" type approach is that the existing user base just has no idea how bad things have gotten, they have a high tolerance for the clutter because they're like the frog who is getting boiled very slowly and doesn't notice it. They've built up a tolerance for the problems because they've been along for the ride for quite a while and are able to tune out added things that they don't care about just as long as the stuff that they have been using for the past 15 years still operates the same. But at that point if someone new comes along they get walloped by the full accumulation all in one single dose and it's a very different experience.
Another thing that happens quite easily is that if many people are working on a product it's very natural for each person to want to "make their mark on it" in some visible way because that's just naturally how it seems like they're contributing and doing a good job. It's a lot easier to keep this kind of accumulation in control when there's only one person working on it. There's a lot less meetings and arguments too... ;)
This type of thing just happens so automatically that I really try to keep actively on guard against it. But also just having one person working on it helps keep it in check a lot with a forced rate limiter.
- Michael
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