So, I was over at PortableApps.com browsing their forums and BLATANTLY stole this from them.
And I love it! Granted, it will try to execute the same app each time you plug in any USB Drive, but since I only frequently swap out one drive, this works like a charm!
I use autoplay handlers built into windows xp to autostart Pstart on plugin of the USB. It can be modified to autostart any program and is just a few registry entries.
Basically, you create a new autoplay option in the registry, which you then choose under the autoplay options in the drive properties window. Then you choose your new option and tell it to always use it and from that time on you only have to plug in the drive and it will autostart that program. Below is instructions on how this can be done. I have copied it from the txt file I keep them in to this post:
---------------------------------------------------------------------------------------------------------------------------
-------------------------------------------USB Autoplay Handler------------------------------------------------------------
---------------------------------------------------------------------------------------------------------------------------
*****What is USB Autoplay Handler?*****
This is a way to create a autoplay handler for USB devices within Windows XP. It allows the user to create an autoplay
option for any program residing on a USB Device or other removable drive. I have included the instructions and necessary
registry entries below. Enjoy!
*****Some Problems to Consider, Nothing to Bad though

*****
So far I have tried this on a number of Windows XP Machines and it works everytime. However, The following needs to be
considered:
1. You do need to have Administrator rights to import the entries to the registry, but After that though it will work
without admin rights.
2. The path the executable will have to be change before you enter it into the registry on a new machine, as the drive
will change. (NOTE: If any one can find an enviromental variable to allow windows to always find the USB Drive,
it would then not need to be changed. I am still looking into it)
3. You must have Autorun enable on the PC for this to work.
Other than the above I see no other problems.
*****Instructions for changing it for any system*****
Below is the registry file you need to create. (Just copy the code in between the Start and End lines)
To make it work for your system and program, follow the below steps:
1. In the second key, change the "Action" Setting, where it says "USB Portable Apps List" to the an action name
such as "Open Firefox".
2. Change the "Provider" Entry to the manufacturer of the program, such as "Firefox Browser".
3. In the third Key, change the "PStart (ISO)" to "(ProviderEntry) ISO", Place what you put in the provider above
in place of the (ProviderEntry). Make sure you put a space and ISO after the entry.
4. In the last key place the path to the executable of the program you want to start.
5. Save the file as a .reg file, and then double click on it to import it to your registry.
6. Plug in your USB drive and then go to "My Computer > USB Drive > Properties" then goto the the "AutoPlay" properties page
click the drop down list and select "Mixed Content" you should see your new entry there.
7. Check the "Select Action to perform" circle and then choose your entry. Choose "Apply" and then "OK" to close.
8. Now log of and back on. This will reload the registry with your new changes.
9. Unplug and then replug in your USB and the program should autostart.
10. Finished!!
:::::::::::::::::::::::::::::::::::::::::::::::::::::::::::::::Start Registry file::::::::::::::::::::::::::::::::::::::::::
Windows Registry Editor Version 5.00
[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Explorer\AutoplayHandlers\EventHandlers\MixedContentOnArrival]
"USBStart"=""
[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Explorer\AutoplayHandlers\EventHandlers\ShowPicturesOnArrival]
"USBStart"=""
[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Explorer\AutoplayHandlers\EventHandlers\PlayMusicFilesOnArrival]
"USBStart"=""
[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Explorer\AutoplayHandlers\Handlers\USBStart]
"Action"="USB Portable App List Start"
"DefaultIcon"=hex(2):25,00,53,00,79,00,73,00,74,00,65,00,6d,00,52,00,6f,00,6f,\
00,74,00,25,00,5c,00,73,00,79,00,73,00,74,00,65,00,6d,00,33,00,32,00,5c,00,\
53,00,48,00,45,00,4c,00,4c,00,33,00,32,00,2e,00,64,00,6c,00,6c,00,2c,00,2d,\
00,38,00,00,00
"InvokeProgID"="USBStart"
"InvokeVerb"="open"
"Provider"="PStart"
[HKEY_CLASSES_ROOT\USBStart]
@="PStart (ISO)"
[HKEY_CLASSES_ROOT\USBStart\DefaultIcon]
@="F:\\Apps\\PStart\\pstart.exe,1"
[HKEY_CLASSES_ROOT\USBStart\shell]
[HKEY_CLASSES_ROOT\USBStart\shell\open]
[HKEY_CLASSES_ROOT\USBStart\shell\open\command]
@="F:\\Apps\\PStart\\pstart.exe"
::::::::::::::::::::::::::::::::::::::::::::::::::::::::::::::::End of Registry File::::::::::::::::::::::::::::::::::::::::
****Final Thoughts****
It is possible to change the icon of the autoplay handler by changing the "DefaultIcon" entry in the second Key. I have it
set to use the USB icon in the Shell32 file in the windows folder, as 99% change it will be on any Windows XP system. If you
want to use another Icon, then chance the entry to a path to the icon. Just make sure you change that path as you would the
path the the executable on a new machine.
****************************************************************************************************************************
Created By Deuce199
Using Windows XP Professional
Tested on Windows XP Professional Systems
December 15, 2005
Any questions just ask.
Deuce