Two brothers and a high school buddy disrupt the system that leaves out the little guys.

A long-lasting friendship that started at New Trier Township High School in Northfield about 15 years ago has blossomed into a successful business relationship. Bob and John Wilson, 30 and 31, have taken many trips to various wine regions with their friend Scott Washburn, 29. Bob spent nearly four years working for a large wine distributor and saw that much of the wine sold in the traditional retail market comes from only a handful of large wine conglomerates. Seeing he couldn’t access most of the smaller wines the trio had tasted on their trips, he joined forces with his lawyer brother John and their friend Scott, a former Groupon employee, to launch in December 2012.

AN INDUSTRY ON THE BRINK gives visibility to and facilitates orders from small wineries (there over 7,000 in the U.S. alone) that lack national distribution. The team – with Bob as CEO, John as COO/general counselor and Scott as director of sales and business development – is intent on changing the way consumers discover, learn about and purchase wine. By giving access to labels that comprise the almost 80 percent of wines in the U.S. that aren’t available through the traditional retail route, Winestyr effectively helps wine enthusiasts broaden their horizons and experience more of the small batch, handcrafted wines that simply don’t get picked up by large wholesalers. They currently contract with about 60 wineries, a number they plan to grow over the coming years.

“Think of what Spotify and Pandora did for music. Uber for rides, Airbnb for travel, Netflix for movies, GrubHub for food delivery, Bonobos for men’s clothing and countless others,” says Bob. “The dynamics of the wine industry are very similar to that of the music industry circa 1999.” He was intrigued by how Napster circumvented industry gatekeepers, giving consumers unprecedented access to music and sees the wine industry heading in a similar direction.

Aside from opening up access to wine produced by smaller players, the Winestyr team also does away with the 100-point scoring system popularized by Wine Spectator. They firmly believe that the qualities that make wines more expensive are also elements that make those wines more difficult to appreciate for the uninitiated palate – qualities like oak aging, earthiness, bottle age, tannins and complexity.

In this vein, you won’t see that traditional scoring system for the wines on their site. Rather, Winestyr wine tasters rate the wines independently. Then, once a consumer purchases wine from the site and creates a profile, she or he is asked to rate the wines. The ratings are stored in individuals’ personal wine profiles and allows Winestyr to then make recommendations of ‘like’ wines that fit their taste profile. They currently make this judgment call manually but hope to have an algorithm, much like Pandora has in music, as the site matures.

The state of the wine industry today, combined with the astounding growth in e-commerce in general, provided a perfect storm of sorts for Winestyr to flourish. According to ShipCompliant – a Boulder, Colorado-based company that helps wineries comply with shipping rules – one short year after launched, wine sales shipped directly to consumers in the U.S. totaled roughly $1.46 billion…a 10 percent increase from the previous year.

Winestyr seems destined to catch some of Americans’ newfound fascination with buying wine direct from the craftsmen who produce it. It’s just a bonus that the company brings the buying process right to your fingertips. Buy your wine in a single click, find more wine you like, then enjoy the vintage in the comfort of your home. We like it.

Kristyna Archer Photograph


About Laura Levy Shatkin

Laura Levy Shatkin served for 10 years as food and wine critic for the Chicago Reader. Later, she became an Emmy-nominated executive producer for Taste, a 30-minute food and wine show on NBC-5 Chicago, which later merged into, where Ms. Levy is a partner/owner. Today, she teaches private wine classes and hosts wine parties for consumers and firms, and continues to tell the video stories of wine, girlfriends and wine travel on her TCW blog, Wine…ing Women.