To wager or stake something (money, life, reputation) on an outcome; to gamble or take a risk on something.
彼は全財産をレースに賭けてしまった。
He staked his entire fortune on the race.
未来の成功に賭けて会社を辞めた。
He quit his job to gamble on future success.
そういう賭けはリスクが大きいから気を付けて。
Be careful; that kind of bet carries big risks.