The most common and most likely answer to this crossword clue is the 3 plus 2 plus 6 letter word OUT OF POCKET
I've seen this crossword clue in The Daily Telegraph
O
U
T
O
F
P
O
C
K
E
T
Buddy explains!
The straight part
We know that "Having lost money" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case having lost money = out of pocket.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.
What does OUT OF POCKET mean?
OUT OF POCKET adjective- Of or pertaining to the spending of cash rather than using credit.
- Lacking funds, or suffering a financial loss; broke.
- (of a person) Not available; unable to be reached.