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What was your gateway product to open source?
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Gaim.
GIMP and Mozilla Browser were a couple of my early ones as a Windows user, but I probably saw those as worse, or at least less polished, versions of other software. Gaim (later Pidgin) was the one that first made an impression on me.
AIM was important software — it basically was social media to me at the time — and I'd stumbled into using third-party add-ons (for example, DeadAIM) for the official AIM client to add extra features and block the in-app ad banner. But it was always a cat-and-mouse game where AOL would try to block add-ons and the developers would have to work around that.
Gaim was refreshingly immune to all that stuff... it simply didn't support ads, and all its advanced features were built-in. That it supported other messaging protocols was a nice surprise too, and to this day has soured me on siloed, proprietary messaging apps. The GTK UI also looked and felt a little exotic on Windows XP.
When I finally moved to Ubuntu, having apps like Gaim, Firefox and GIMP ready to go made things pretty comfy.