Airing between regular episodes of the VinePair Podcast, “Next Round” explores the ideas and innovations that are helping drinks businesses adapt in a time of unprecedented change. As the coronavirus crisis continues and new challenges arise, VP Pro is in your corner, supporting the drinks community for all the rounds to come. If you have a story or perspective to share, email us at podcast@vinepair.com

In this “Next Round,” VinePair Podcast co-host Zach Geballe speaks with Will Whelan, vice president of wine at Winestyr, a Chicago-based direct-to-consumer wine club and e-commerce platform.

During the discussion, Whelan explains how Winestyr allows consumers to buy wine directly from wineries. The unique model of the platform is such that consumers can buy wines specifically from nearly 120 wineries, while Winestyr stores the wines and fulfills orders from its Illinois facility. Whelan praises the benefits of this model to smaller West Coast wine producers. By bringing small wineries together on one DTC platform, Winestyr gives these unique wines a bigger collective voice in the market.

Whelan also speaks to some of the challenges associated with facilitating DTC sales. Not only are there legal hoops to jump through from state to state, but most wine consumers aren’t used to buying wine online. Whelan compares the online wine-buying process to buying clothes online for the first time: You may not know exactly what you’re getting without having tried the product first, and that can feel risky for consumers at first.

In order to overcome this barrier, Whelan shares strategies to make online wine purchasing more comfortable and approachable, such as Winestyr’s use of email marketing to bring the stories of individual wines to life.

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