Learn more. When an entrepreneur invests her own money in her business, she gambles on its success. "He took a gamble and quit his job to start his own business. To take a risk with the hope of gaining an advantage or a reward, often in the form of money. Mark won half a million dollars gambling on horses. When you gamble, you take a risky chance on something. the president's risky gamble in calling a referendum. to wager or risk (money or something else of value): to gamble one's freedom. Dec 12, 2025 · Gambling is the betting or staking of something of value, with consciousness of risk and hope of gain, on the outcome of a game, a contest, or an uncertain event whose result may be determined by chance or accident or have an unexpected result by reason of the bettor’s miscalculation. Define gamble.