I would imagine it is hard to start because of an ignition issue. If that is the case, once you are choking, cranking, pumping, etc, and you are not getting enough spark, weak spark, or a spark at the wrong time, then that fuel is seeping right past the rings - once the piston gets to the top of the compression stroke especially because the compression will push it past the rings (gasoline is obviously thinner in viscosity than oil).
Dry Lakes Racer is right about the drainage. These carbs tend to drain out when SITTING for any period of time. My take is today's fuel that has a chemical content/makeup that lets it seep past the old power valves pretty easily. I know I have had that problem in the past.
"I know a lot of you all mentioned the dizzy and adjusting the timing. I plan on it just haven't gotten the chance yet." - you really need to do this here.
Daniel JessupLancaster, California
aka "The Hot Rod Reverend" 
check out the 1955 Ford Fairlane build at www.hotrodreverend.com