Once you’ve read Art of War by Sun Tzu, the biography of Cyrus the Great, or any of the wisdom of Charlie Munger & Warren Buffett, you will quickly realise that the secret to winning is “not losing”.
These guys all ensured that whatever they do, they can’t be killed if it doesn’t work out (financially or physically).
Another thing you’ll discover is that every single great success story was predicated on a massive win early on, from which the compounding effect of small subsequent wins resulted in the world’s greatest empire (or balance sheet).
Massive wins don’t come without massive risks. The moral of the story is that as long as you have nothing, take big risks. Once your ship comes in, stop taking big risks and start taking small risks.