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The hint is in his complaints: he probably lobbied Cisco for budget to have a Big Rewrite and they said no. So he upped sticks and did it elsewhere.

Are you proud of your code from 20 years ago? He probably wasn’t either.

Once Cisco bought, it sounds like a lot of control was removed from his hands? New company (Cisco) didn't want to invest in what they thought was a mature product that serviced the market well enough?

How many enterprise web tech products from 1997 do you think survive today with a healthy architecture and usable design?

Plus that whole "I told Cisco leadership, but they didn't listen" surely was not the first time it ever happened.

I'm sorry you were downvoted for an interesting remark. It resonates with me that sometimes you are stuck within a structure that was created by you and need to completely change environment to be able to achieve new goals. Quite interesting point here.