Sounds like a case of tunnel vision rather than "copywriting is bullshit".
Dan Kennedy's Marketing Triangle:
______Message______
Market_______Media
Send the right message to the right market using the right media
In this case, it was the WRONG message to CEOs using Email (or right message to wrong market - either way there was a mismatch there).
Sounds like he copied out a lot of Gary Halbert Ads by hand but didn't keep in mind many of them were newspaper ads targeting broad audiences via print.
Over excited to finally release built up knowledge and get some action... resulted in loss of common sense and a premature ending.
edit: ugly triangle..
THIS.
Copywriting isn't about using "dear friend" or copying tactics you saw someone in the past use, it's about writing a message to a person. No good copywriter would have written a letter like your friend did. Unfortunately reading and copying copy doesn't make you a copywriter
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