Jared,
I have a 35T that does the same except when it sit for more than one day. I pour a little gas down the carb so it will start. I am guessing the carb bowl runs dry and needs a little prime to start for the first time. Starts fine the rest of the day.

I agree with Bill. The fuel bowls are empty because todays gas boils off at a lower temperature. You can alleviate the problem by adding an electric fuel pump near the gas tank and only use it to prime the carburetor before starting. I use the one below on a toggle switch for my 53 Super Wasp. A couple seconds is all it takes to prime the carbs.

https://www.summitracing.com/parts/mrg-12s/overview/

Jared, do a little more diagnosing. As they have pointed out, just pour a little fuel down the throat of the carb before cranking it over. if that works and it fires right up, then repair as needed. If that does work, inspect the fuel lines very closely. It would almost have to have a leak somewhere allowing the line to empty itself?. If that doesn't correct the concern, then check the distributor. I have found ,because of the location of the dist., moisture is allowed to form inside the base, causing the advance counter-weights to stick. When the engine was running last, the natural heat from the engine allowed the weights to be somewhat free,but sticking, but once it was shut off, they could still be stuck in the advance position, not allowing it to come back to base timing. The same goes for the points, the pivot post also gets real sticky, and does not allow the points to open and close, but after cranking it over, like you described, finally lets them open and close, then makes spark,fires up?. These tips are things I have experienced that drove me crazier than I already am! Hope this helps,

Doug, thank you....I wonder if it could be related to the dist. It's beginning to drive me crazy too! It acts like no gas, but on a couple of occasions over the past year, I poured a little gas in the carb and it didn't make any difference. I always hate to pull a distributor, but maybe I should, and this winter I can clean it up good and maybe replace some internal parts if necessary.

After you DO get it started, and you run it for awhile and shut it off, does it start right up again? Or does it grind and grind once again?

And, let's say, an hour after you shut it off, does it spring to life again? Or, is it the old grind?

Jon, after it has been running, it will start right up again....including up to several hours afterwards. Once cold (after sitting overnight or longer) it fails to start. After several attempts (and a battery recharge) it will eventually start, but I have yet to determine the reason it will not start, nor the reason it eventually does start up. Yesterday I installed a see through gas filter just before the fuel pump, let it sit overnight, and the line is holding gas (filter is full of gas).

Guess.... carb is not keeping fuel in the fuel bowl. Then the fuel pump is taking a long time to bring fuel to refill the carb. Check the fuel pump to assure it is adequately pumping as well as assure the carb needle and seat are properly holding fuel in the fuel bowl

I haven't delved into this yet, but I have noticed that the outside of the carb body appears damp lately....perhaps this is a clue to the problem?

Jared,

I don't use my '35 very much, so my float chamber has leaked out, and the gas in the tank has had a chance to get old. Some years ago I installed a tee fitting near the carburetor. Attached to this is a hose that goes to an electric fuel pump, and the electric fuel pump is connected to a one gallon container of gas. I fill this with fresh gas and briefly use the electric fuel pump to fill the float chamber. This way the empty float chamber gets filled with fresh gas. The car starts right away.

Per

Per, thank you! I like the idea and may use it. It reminds me of an old farm tractor I restored which has a 'reserve tank'. The same principle: use the gasoline in the 'reserve' tank to start the tractor, then switch over to a lesser fuel (kerosene) in the main tank.