168: Drew Bledsoe, from Pro Football to Wine Estates


Upon his retirement from the NFL in 2007, Drew Bledsoe “doubled back” to his hometown of Walla Walla, Washington to realize a long held dream. Drew and his Wife, Maura, purchased a piece of property on the southern edge of the Walla Walla Valley AVA and subsequently launched Doubleback as an estate focused winery with the goal of crafting America’s best Cabernet Sauvignon in an elegant, true to varietal way. Drew had long been planning for this moment during his years playing football and success came immediately as the very first vintage earned a spot in Wine Spectator’s Top 100 List.

Drew hired Josh McDaniels, now CEO & Director of Winemaking, away from Figgins Family Wine Estates where he had trained for almost a decade under their longtime mentor and friend, Chris Figgins. Josh, also a Walla Walla native, has been named a “Washington Prodigy” and a “Game Changer of Washington Wine” by Wine Enthusiast Magazine. The collaboration between Drew and Josh is a competitive partnership that pushes them to continue the pursuit of perfection in Cabernet Sauvignon every day.

Doubleback remains a small, family owned winery located on the southern edge of Walla Walla in its new home that was completed in 2018. The winery has four estate vineyards all located in the Walla Walla Valley and all unique to the other. Each vineyard is sustainably certified and farmed by its own incredible farming crew that is an integral part of the team. The team welcomes it’s mailing list customers by appointment only daily.

Where we are:



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Time Stamps:

  • 10:42 – When did you know you wanted to go into the wine business?
  • 13:20 – Has Walla Walla always been producing really good wines?
  • 16:30 – What kind of investment advice is given to young athletes?
  • 21:20  – Have you had other crazy investment proposals during your career?
  • 24:58 – How was the transitioning for the NFL to the Wine Estates?
  • 29:05 – How did you start with Doubleback once you retired?
  • 31:06 – Did you know the economics of the wine business?
  • 34:15 – Why do you think a lot of winery businesses fail?
  • 40:06 – What are the future plans for the estates?
  • 44:08 – Do you see this business staying in the family? 
  • 50:26 – Sam and Derek review

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