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I believe it was PC Plus Magazine that was the first to go ahead and mount a free disk on the cover. But very shortly afterwards Europress (who I was working for at the time) knew they would also have to offer free disks to stay competitive with their title Personal Computing with the Amstrad and IBM Compatible PCs - yeah, they had a knack with magazine titles!
This one was a cock-up in my opinion because the title was originally Personal Computing with the Amstrad or as we called it PC Amstrad. Europress had banked on the Amstrad name for a number of different titles and chose to use it for the launch of their new PC magazine. Personally I think they were short-sighted and didn't realise that the IBM compatible was going to be the next big thing (and as it turned out almost the only one apart from good old, Apple hanging in there). I think that if asked I'd have probably recommended the name PC Computing (I don't think that name had been taken in the UK, although there was PC/Computing in the US).
But I digress. As I was saying, Europress pulled me off editorial roles and got me to work full steam on sourcing good products for cover disks. So I was thrown it at the deep end, and just got on the phone for about two weeks calling every company in the industry. Pretty soon, though, demos were coming in along with great shareware and public domain programs and I was starting to build up a stack of good software. Of course, once the disks became regular, we started getting reader submissions too, which helped a lot.
The more disks I produced, the more promotions I had to make to help pay for the cost of them, and so that's how my dual roles of Cover Disk Editor and Promotions Coordinator jobs started. I became quite good at it too, making deals worth anything up to £75,000 (although not that large for Europress), and with discs I had authored on anything up to eight magazines at a time on the bookstands.
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