This NFL Legend Has Built A Wine Empire, Calls It Fun But Not Easy

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Not every football player leaves the NFL and finds their footing in an entirely different business. In fact, many NFL players lose much of their wealth in the years after retirement. Drew Bledsoe, a number one draft pick and the former quarterback for the New England Patriots, is one who has managed to have a fantastic second act in a field that many of us dream of getting into: the wine business.

In an interview with Jason Raznick on The Raz Report podcast, Bledsoe explained that he didn’t venture into entrepreneurship until he retired but credits having good financial advisors along the way for “not letting me do anything super stupid” and saying no to him frequently. Once he retired, Bledsoe and his wife Maura decided to pursue their dream. In 2007, they returned to his hometown of Walla Walla, Washington and purchased land in the Walla Walla American Viticultural Area (AVA). They partnered with winemaker Josh McDaniels and focused on growing cabernet sauvignon. Since that initial investment, they have expanded their winery to include five estate vineyards in the Walla Walla Valley.

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After the initial success with Doubleback, the Bledsoes expanded, creating two more labels under the Bledsoe Wine Estates brand. The Bledsoe Family Winery produces accessible varietals, while the Bledsoe|McDaniels Winery was established to offer their version of the Willamette Valley’s Pinot Noir. They also expanded into homegrown Syrah, with these limited-production wines available to wine list members.

Bledsoe describes the journey to success in the wine industry as fun but challenging. “It’s been super rewarding to see something grow from a single vineyard that we planted with our hands to a company that has 70 employees and over 450 acres of vineyards,” he said.

Like any type of investment, investing in the wine business requires time and patience. “Sometimes you are talking a decade before you get to see the literal fruits of your labors,” Bledsoe added. Unlike football, where results are immediate, the wine industry requires long-term commitment and resilience.

Bledsoe sees parallels between being a quarterback and owning a business, citing skills such as planning, executing decisions, building a team, and dealing with adversity as lessons.

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In addition to his winery businesses in Washington, Bledsoe has invested in real estate in Whitefish, Montana. He describes the market as rapidly growing since he first discovered it in 1996. Speaking about his home, he said it’s one of his better investments but one that he will never realize because then he would have to sell, move, and find another house. He said he has dabbled in real estate, with some good and bad outcomes.

When it comes to investing, Bledsoe has primarily left stock investments to his financial advisors, giving him time to devote to what he knows best. Investing in wineries can be a tough business. As Bledsoe mentioned, it’s a luxury business that is very tied to the strength of the economy and the vicissitudes of Mother Nature. It also requires tremendous capital and knowledge, both of which Bledsoe has as he focuses on building a wine empire for the long haul.

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