Drew Bledsoe

Doubleback: Building the Second Act Before the First One Ends

Drew Bledsoe was the number one overall pick in the 1993 NFL Draft and played fourteen seasons at quarterback for the Patriots, Bills, and Cowboys. He has now spent longer building a wine business than he did playing football.

While still playing, he was already planning what came next. On retiring in 2007 he returned to his hometown of Walla Walla, Washington, planted a vineyard within a mile of where he grew up, and launched Doubleback with his wife Maura the following year. The first vintage landed on Wine Spectator’s Top 100 Wines of the World.

What followed is a business story. Bledsoe recruited a twenty-six-year-old winemaker away from a rival estate, made him a partner, and eventually handed him the CEO role. He built three distinct labels at different price points, developed five estate vineyards, expanded into Oregon, and grew sales through a period when the wider wine market was contracting.

He takes audiences through why he started planning his second career during his first, what it took to learn a new industry from scratch in his mid-thirties, why hiring someone more talented than you and giving them real authority is the hardest thing a founder does, and how you grow when your category is shrinking.

Authentic Leadership

Drew Bledsoe’s journey from the NFL to entrepreneur is a story of determination, resilience, and staying true to one’s values. In this compelling talk, Bledsoe explores the principles of authentic leadership, highlighting the importance of sincerity, loyalty, and family in both personal and professional life. He shares how his experiences in football and business have taught him to invest deeply in his community and remain unwavering in the face of challenges.