Create downloadable Desktop Player for instant listening
Something I remember using from the early '00s, not just with Live365 but also at the long-defunct Spinner.com - a small player interface that you could download and park on your desktop, similar to the Widgets but without needing to code your own website and manually embed in the code. You just downloaded and hit Play. The Live365 player had an impressive menu of skins and a search feature where you could see all other Live365 stations that played a particular song, etc. - cool but not essential. They basically destroyed the design' s retro visual appeal (shortly before the BK) by trying to make it look like a faddish "i"-something, but it still worked.
Just being able to play Live365 from a direct desktop player without navigating to the website itself meant instant listening, therefore more listening. It was also far less cumbersome when listening at work when you've got a ton of other windows open.