this post was submitted on 28 Aug 2024
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That pin can be found for $30 or $35 on on ebay here and here, where it is described as being from the 80s and as an "employee pin".
I was thinking that this might have been something aimed specifically at technology buyers in US schools in the 80s or 90s, to whom Apple offered substantial institutional discounts in a (relatively successful) effort to dominate that sector. However searching the phrase "does more costs less" i found this TV spot advertising the Quadra 605 which at $1000 was the cheapest computer Apple sold when it was introduced in October 1993 (and allegedly cheaper than something else they refer to as "PC Leading Brand" ๐). That system was sold under the LC and Performa brands up to 1996, but it was only sold as a Quadra until October 1994, so, to answer OP's question: that slogan was in use at least sometime in that year.