If you just never play to win, like me, doing badly will not affect your enjoyment at all. Every round is a new chance to introduce the host to something they may never have even heard of, I think that's a great concept in itself.
Well, "playing to win" and "quitting like a baby when you don't" aren't the same things. I play to win (even if it doesn't seem like it) but I also have a different pool of music to pull from. The people running the roulettes around here - for the most part - seem to like a certain genre that I am just not versed in. So I opt for an alternate strategy that sometimes works (Kattleox) and most often doesn't, i.e. taking things we already THINK we know, and re-purposing them. I am seriously considering submitting my future offerings scrubbed of band and album information (and I am seriously considering having an "anonymous" round when I have my next roulette). There's a bias here against things that "sell" for some reason, and I don't really understand it. For me, I think it's part of - not all, but part of - the magic when an artist can write something with the best of intentions, and have that work emotionally touch millions of people.
Lethean did the anonymous thing earlier, and it really didn't make much difference. As I've said, I'm randomly and blindly playing my first 2-3 listens so I'm (for the most part) completely oblivious to what I'm listening to. There are exceptions - like when I got Alice Cooper and Heart... kinda hard not to know which ones those were. Even the title doesn't often give me a clue, because my first listen I'm usually multi-tasking, so I often times don't even pay much attention to the lyrics.
This round for example... even though Evermind gave a bit of details in his description (female, symphonic), TAC's song was also female/symphonic... so I didn't know which song was which. At least 1/2 of what I listen to the first couple times, I literally have no idea which song it is, or who submitted it - which is helping me remove any unintended or subconscious bias.
I believe I'm allowing the music to stand on its merits on by itself.