We just got this board too and it also won't sync. We never got it to sync even did it once. When you press the power button on the board, it just does a quick green light and goes off.
1. push the button on the connector
2. hold the button on the skateboard for 3-5 seconds and the little lights should start blinking
3. let them blink for a second and then push the(xbox button),if it doesn't go to player 1 or 2 right away just keep pushing it till it does
well freind im new and mine wont either so delete the saved data ,get new batteriess,and follow the long but simple instructions tony gives you.after this the game will be a breeze i promise.
ok buddy change batteries press the little button on the board and xbox 360 console hold them both aproximetly 10-15 seconds until they connect, (note u will need an instruction manual)freind this happened to me as well><)