All photos via Winestyr

Wine tasting has been a sophisticated semblance of fine living since the 14th century. While the art is as ancient as its production, the cultural appreciation for it has more than improved. From Napa Valley’s specialty Cabernet Sauvignon to Russian River Valley’s impeccable Pinot Noir, prepare yourselves: the best tasting wine from the most profound wineries in the country is now accessible online.

I sat down with the talented and seriously hard-working operators behind the groundbreaking concept of making extremely rare, wildly unique and incredible tasting wines available to the average consumer. From conducting years of research on the alcoholic beverage industry to tasting thousands of wines, these guys have fully immersed themselves in discovering the absolute best wines out there, and have made them available in the most authentic way.


Wilson brothers John and Bob and his lifetime friend Scott Washburn founded Winestyr on a simple notion: the best small production wines should be more accessible.

Unlike other wine sites that offer pages and pages of different wines with no explanation of what you’re getting, Winestyr has built a curated portfolio of well-made, high quality wines full of complexity and uniqueness that you won’t find anywhere else.

The traditional distribution channels of wine selling skew heavily towards large producers who work with large wholesalers; manufacturers are able to make it in the retail space of restaurants, bottle shops and liquor stores. Then you have all of these small wine producers that are trying to figure out how to get into retail, and they can’t do it.

If you are a producer of wine, (namely, a winery) you only have two options by law to sell a product. The traditional route is selling to the wholesaler, who can only sell to a retailer, who can then sell to a consumer.

What consumers don’t realize is that over 50 percent of the wines sold at retail in the United States is one of three huge conglomerate producers, meaning the “different” wines you keep buying in convenience stores really aren’t different at all.

With over 7,000 wineries in the U.S., small producers of wine have no way of getting to consumers other than people actually coming to their wineries. They’re left trying to figure out a way for the consumers to find them. This is where Winestyr comes in and facilitates their genius concept. They expertly find what they believe are the best of the best types of wine not found on store shelves, and put them on their website for customers to directly buy.

“We are an entirely unique business model,” John said, “As far as I know, there’s nobody else that does what we do.”


How Winestyr came about

While out wine tasting in Michigan near the Wilson family lake house, it occurred to Bob how terrible it was that not many people know about these amazing small wineries, and he wondered why there wasn’t a way for these fantastic wines to be on store shelves. So he, along with John and Scott, found a way.

After a brief phone call to John about the idea, Bob asked for a business template, and in the span of a few days, the concept was created.

“Bob had what I call a Jerry Maguire moment,” John said. “He hammered out a 35-page business plan in 48 hours that has remarkably changed very little since he did it, which was six years ago.”

Realizing this seemed like a great opportunity from the support of influential people in the industry and various investors, the trio told family and friends they were serious about starting the business. And after a long 10 months, they raised enough money to get started, quit their jobs and became fully dedicated to Winestyr. 

Who is it for? A premium price point for a premium product


There are types of wine consumers in extreme: one who only buys on price (they want a cheap, $6 bottle of wine) and a wine collector (someone who spends ridiculous amounts of money on wine to store for decades). Between these extremes exists the attractive proposition to court most consumers: those who shop for a $20-$50 bottle of wine. This is the fat, middle market of everyone else who wants a unique bottle of wine that they know consists of superior quality, and they know they are going to enjoy it. These are (typically) individuals who are starting to mature a little bit more, making more money and realizing it’s time to swap the not-so-great tasting wine for the better tasting, higher standard wine.

Making the comparison to the little neighborhood places on the corner that require local knowledge and experience to know about, John paints the picture of a memorable, desirable experience which parallels the representation of Winestyr. 

“We all have that place in mind that has the unbelievably unique dish, that’s totally amazing, where the wait staff is hilarious,” he says. “Is it more expensive? Not necessarily. Is it cheap? Definitely not. Are most people this day and age willing to find those enjoyable restaurants and pay a reasonable price for it? Definitely. That’s what we are for wine. We offer a fantastic value of wine that you wouldn’t otherwise find.” 

Wine tasting in Chicago

By early to mid-September, Winestyr will open their current (and insanely cool) West Loop workspace to the public by appointment only and private events as to showcase their work.

You’ll be able to come in with some friends, hear about what we do and taste our wine,” Scott remarks. “It will be a hugely classy entertainment venue that is professionally catered, and very representative of the type of quality you can expect from our service.” 

A belief in keeping up with face-to-face interaction of a new business in addition to maintaining an e-commerce presence is a large part of why the space is welcoming to customers.

I think that’s what we’re really trying to do here,” Scott said. “I think we can argue that wine might even be more important than some of this other stuff like fashion. You find something you like and something you don’t like, which should show really well for our potential market.” 


Standing out from other startups

Next to other startup founders who may have had advantages when starting out, whether financial, knowing the right industry professional or something else, Bob, John and Scott started everything from scratch, which makes their business concept even more attractive.

“There has not been a single shortcut taken with this business,” John said. “We’ve seen in the wine industry and in general a lot of companies came and went because they took shortcuts. And we didn’t. We took amazing painful steps to make sure we were doing this compliantly. And it’s been completely worth it. People realize that we are 1000 percent genuine and absolutely committed to quality.” 

Truly committed to their customers, these guys have done their homework investing a lifetime value of making their brand known and set apart from anyone else. Presenting a good product instead of reinventing the wheel has made their company exceptionally successful.

We can’t wait to see what’s in store next for this wine culture panache.