Thanks for using the Reckon Community. I have some general ideas that may help, give these a try.
Reboot your PC, then while holding Ctrl and Shift down double click on the QuickBooks 08/09 icon and continue holding Ctrl and Shift until the program opens. If it doesnt open after 30 seconds let go of Ctrl and Shift and try the next step.
If using Windows 7 or 8 - Right click on the QuickBooks 2008/09 icon and choose Properties > Compatability > tick Run this program in compatability mode for > select XP Service Pack 3 > tick Run this program as Administrator > Apply > OK > Try to start the program again.
You might like to consider upgrading the most current version as the 2008/09 version is no longer supported by Reckon Technical Support. Once upgraded to the current version you will be able to get more detailed, in-depth, one on one support.