A term me and couple gaming friends used a lot playing a Battle royale game we used to play a lot in university. Risking it all in that game was a high risk, high reward type of strategy which usually resulted in a lot of deaths but the wins were usually sweet and over time we get better. but that's a game, in real life risking it all (or going all in with a plan) is really high risk and you only have one life. failure can result in massive monetary loss or even worst death but on the opposite if it works that success can set your life up for ever. 

my opinion is to learn as much as you can before you try a high risk project, but after while if you want it enough you have to take the leap or you may live the regret of not ever trying.