1. To bet or risk everything one has on some wager or venture. Tech companies seem to be betting their shirts on virtual reality being the future of the industry, but there are plenty who think that's a foolish stance to take. Anyone with a gambling addiction knows the feeling of betting your shirt on a hand of cards, feeling sure it will pay off big time, only to lose everything.

2. By extension, to be absolutely certain that something will happen. I would hope that the industry is moving towards a more customer-friendly position, but I wouldn't bet my shirt on it.