Drew Bledsoe was a star quarterback at Washington State University before he skipped his senior year to go professional. In 1993, he was the No. 1 NFL draft pick and joined the New England Patriots. After nearly eight years he was traded to the Buffalo Bills, then moved to the Dallas Cowboys, before retiring in 2007.

Post NFL, Bledsoe pursued a longtime aspiration of owning a winery, which would allow him to combine his passion for fine wine and love of the Walla Walla Valley. Drew returned to his hometown in 2007 to plant his estate vineyard, McQueen, in SeVein Vineyards of Distinction. The following year, Drew launched Doubleback, an estate-focused winery with the goal to produce ultra-premium Cabernet Sauvignon from the Walla Walla Valley.

Since the first release, the 2007 Cabernet Sauvignon, Doubleback has received numerous accolades including a spot on the Wine Spectators Top 100 List. The vision for Doubleback remains to be a premium wine experience completely focused on quality.

“The goals that I set weren’t tied to results. They were tied to personal values and ultimately those things allowed me to be successful as a football player.”

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In This Episode:

  • How his parents fueled his curiosity growing up
  • Why public speaking was the most important class he ever took
  • The moment where his mentality on going for it changed forever
  • Why a strong family structure allowed him to not be afraid of failure
  • Why football was never on the list of his top 3 goals
  • Putting an emphasis on the minutia on and off field
  • The most important interview question he asks
  • How he dealt with losing his job to Tom Brady
  • Leadership in understanding when people needed a hug vs. the whip
  • Visualization leading to confidence
  • Comparing his situation to Dak Prescott & Tony Romo
  • Embracing pressure rather than seeing it as negative



“I’ve always been really curious and if you’re curious you’re almost admitting that you don’t know everything.”

“The most important question I ever ask in an interview process is ‘what have you failed at.’ That ultimately should lead to “… and what I learned was.”

“If you’ve never failed at anything then you’ve probably never risked anything.”

“Dignity has nothing to do with how other people treat us. It has to do with how we treat ourselves.”

“Your circumstances don’t define you. You define you and you do the best you can with whatever’s presented to you.”

“As a quarterback, you always had to display an unwavering belief in what you were doing even if you didn’t actually feel it.”

“People always would try to portray pressure as a negative thing but I always looked forward to it. Put me in a pressure situation, that’s where I function best.”


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Drew Bledsoe is a former American football quarterback who played fourteen seasons in the National Football League. Bledsoe is best known as the starting quarterback for the New England Patriots from 1993 to 2001.