For someone who is said to have experience as a scout, he really took pretty bad decisions.
Holding that amount of money alone and not assuming that something could go astray, even if he believes the request came from the guild master, is just dumb.
The first thing he should have done after leaving the city was to go
Rambo Goblin Mode and go through the wilderness, always looking for places to hide and waiting to check if there's someone on his trail.
But, 'nah'!: "Let's use the main road. I'm just an inconspicuous man traveling alone. What could possibly go wrong?"
10 minutes later.
"Whooops!"