Windy type is feeling glum after bad start ending in bankruptcy (5)
I believe the answer is:
blowy
'windy' is the definition.
(synonyms)
'glum after bad start ending in bankruptcy' is the wordplay.
'glum' becomes 'low' (I can't justify this - if you can you should give a lot more credence to this answer).
'after' means one lot of letters go next to another.
'start' suggests taking the first letters.
'ending in' says to take the final letters.
The initial letter of 'bad' is 'b'.
The last letter of 'bankruptcy' is 'y'.
'low' put after 'b' is 'blow'.
'blow'+'y'='BLOWY'
'type is feeling' 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?
(Another definition for blowy that I've seen is " Windy".)