After Free Flow Wine’s business model stopped working, it reinvented itself. When it ran up against a Prohibition-era regulation, it convinced Florida to rewrite the law.

“Crushing it” doesn’t have the same meaning for entrepreneurs in Silicon Valley as it does in California’s wine country 100 miles to the north. In one of the world’s oldest businesses, innovation carries a stigma—considering how long it took folks to come round to the screw cap. “We’re surrounded by tech companies,” says Jordan Kivelstadt, the 32-year-old cofounder and CEO of Free Flow Wines. But the grape trampling racket? “Nothing is so unbelievably resistant to change.” So he and cofounder Dan Donahoe, 45, have learned to dip and drop with the best of them in tech land.

Free Flow is in the wine-on-tap business, though it doesn’t make, deliver or serve the stuff. Instead, it provides the means to get wine to thousands of restaurants around the country, suctioning up the product from vineyards on four continents into 5.16-gallon stainless steel kegs. It partners with distributors in nearly every state to ship 6,000 kegs a month to the likes of the Ritz Carlton on one end and P.F. Chang’s on the other. For this service, Free Flow expects to lose $1 million on revenue of $3 million this year. It’s an asset-heavy volume game: The company has to buy 2,000-4,000 kegs every month to meet demand. Still, it hopes for operating profits in a few months.