Dakota Shy began with Todd Newman leaving Minot, North Dakota with $1,500 and an Amtrak ticket, landing a job at St. Helena's Martini House and eventually working his way from cellar rat to running national sales at Revana Family Vineyard. There he met Tom Garrett, then assistant winemaker under Heidi Barrett, whose great-grandmother had bought Oakville land in the early 1950s that was part of the original To Kalon Vineyard — fruit Garrett still bottles under the Detert label. The two launched their own brand with the 2012 vintage; the name pairs "Dakota" for work ethic with "Shy" for the doubt of a small-town kid in the middle of Napa. In 2014 they bought a rare valley-floor parcel at the base of Pritchard Hill off the Silverado Trail. The flagship Napa Valley Cabernet has twice made Wine Spectator's Top 100.