I feel like boasting about something you did 20 years ago is kind of cringe. I think you've had enough time throughout those years to receive the fruits of your labour for it. Now it just feels like he's milking it?

He doesn't seem to have a lot of stories to tell about his time at Microsoft, but the few he does have were pretty interesting to hear. I think he got used to the dopamine rush of internet praise, ran out of interesting things to say, and kind of pivoted. I would've done the same.

It's not like he needs to peddle merch or anything, I doubt he needs the income. His whole channel seems to just be a hobby and talking about old MS stories attracts Youtuber viewers en masse.

I think there are quite a few more interesting stories he could tell from his more recent time as a malware/scareware developer, but the internet probably won't be quite as appreciative of them as his Task Manager story.