I have explained many times that I am, by Profession, a Gambler — not some jock-sniffing nerd or a hired human squawk-box with the brain of a one-cell animal. No. That would be your average career sportswriter — and, more specifically, a full-time Baseball writer.

This poor gambler isn’t even a noun. He is kind of an adverb.

Gambling is only the resource of those who do not know what to do with themselves

As entrepreneurs, we make bets everyday. We are gamblers — gambling our hard-earned money on labor, inventory, rent, marketing, etc., all with the hopes of a higher pay out. Oftentimes, we lose. But, sometimes, we win and win BIG. However, there is a difference between gambling in business and gambling in a casino. In a casino, the odds are stacked against you. With skill, you can improve them, but never beat them. In contrast, in business, you can improve your skills to shift the odds in your favor. Simply stated, with enough skill, you can become the house.

I used to be a heavy gambler. But now I just make mental bets. That's how I lost my mind.

Gamble everything for love, if you are a true human being. If not, leave this gathering. Half-heartedness doesn’t reach into majesty.

I was, in life, to be a gambler, a risk taker, a swashbuckler, a knight. I accepted, then and there, my place in this world. I was a fighter of windmills. I was a chaser of whales.

If you gamble long enough, you'll always lose — the gambler is always ruined.

Yes, I can understand that a man might go to gambling table - when he sees that all that lies between himself and death is his last crown

This was my first lesson about gambling: if you see somebody winning all the time, he isn't gambling, he's cheating. Later on in life, if I were continuously losing in any gambling situation, I would watch very closely.

Dangers have their appeal because in danger your day-to-day, ordinary consciousness cannot function. Danger goes deep. Your mind is not needed; you become a no-mind. You are! You are conscious, but there is no thinking. That moment becomes meditative. Really, in gambling, gamblers are seeking a meditative state of mind. In danger – in a fight, in a duel, in wars – man has always been seeking meditative states.

It is my experience that bold decisions give the best promise of success. But one must differentiate between [strategic] and tactical boldness and a military gamble. A bold operation is one in which success is not a certainty but which in case of failure leaves one with sufficient forces in hand to cope with whatever situation may arise. A gamble, on the other hand, is an operation which can lead either to victory or to the complete destruction of one's force. Situations can arise where even gamble may be justified - as, for instance, when in the normal course of events defeat is merely a matter of time, when the gaining of time is therefore pointless and the only chance lies in an operation of great risk.

a decision without an alternative is a desperate gambler’s throw,

A given man lives a life free from boredom by gambling a small sum every day. Give him every morning the money he might win that day, but on condition that he does not gamble, and you will make him unhappy.