NM seems to be zeroing in on something but I'll toss out an educated guess of a leak on the suction side of the system.
I reckon at rest air is getting and letting the fuel drain back to the tank. The first start just runs out what in the fuel filter
and HP side.
I would try 2 things.
1 - Do what you normally do. Pull the fuel line from the bottom of the silver can. If no fuel drains out the fuel is draining out of the system at rest.
2 - Stop the fuel cock if you don't already. This would stop a drain back to the tank. Try a start the next day.
I would first make sure the Racor
is assembled securely and correctly. In fact I would remove the bowl, check the seal and reinstall. I always put a little vaseline on low pressure joints.