Rolling On The Floor Laughing initially - Hob's going to head up admiral's first fleet! (8)
I believe the answer is:
flotilla
'fleet' is the definition.
(I've seen this before)
'rolling on the floor laughing initially hob's going' is the wordplay.
'rolling' is an anagram indicator.
'initially' indicates taking the first letters.
'hob's going' becomes 'illa' (I can't explain this - if you can you should give a lot more credence to this answer).
The first letters of 'on the floor laughing' is 'otfl'.
'otfl' anagrammed gives 'flot'.
'flot'+'illa'='FLOTILLA'
'to head up admiral's first' is the link.
I am not very happy about this link. Some or all of it may be part of another bit of the clue.
Can you help me to learn more?
(Other definitions for flotilla that I've seen before include "set of boats" , "Fleet of small vessels" , "number of small ships" , "Group of boats or small warships" , "number of boats" .)