Of course losing all of it wouldnt be preferred lol but risk/reward is a thing. I'm not talking about a large percentage of my disposable funds. I've enjoyed some blackjack in the past and it doesnt look like I'll be going to vegas soon, reallocate that budget with a touch more educated guess vs luckRoll the dice and take a chance then. I would guess that you would be at about 50/50, a gamble. T, AAL, INTC, XOM, BP, AAPL..... Take a pick, for whatever your reason is... So you are in a position to lose it all in the course of learning? My hat's off to you Sir!
In my opinion, you should be looking at a timeframe of 5 years or more with much pain possible in those 5 years.
In my personal opinion, with your stated knowledge of the stock market and personal finance, you should be looking at broad market funds as offered by Fidelity or Vanguard.