Matt Dukes | From Lawyer to Entrepreneur & Wine Aficionado

Matt Dukes left his position as a corporate lawyer to take a break, reflect, and work on a vineyard in France for a few months. The plan was always to return back to his 80-hour per week grind and move back to New York, but something about the wine industry caught Matt’s imagination. He decided to start a wine subscription box called VINEBOX (which eventually led to his second company, Usual), and took off to California instead. Here’s how Matt reinvented himself as an entrepreneur in an industry that he knew nothing about. 

Leaving Corporate Life & Reinventing His Future

Matt grew up in a small town in Florida, but moved to New York after finishing college where he practiced corporate law. Matt lasted three years before realizing he wanted to do something different. He was burnt out, wanted to change the direction of his career, and needed some time to think things over.

Matt found a volunteer position working in a vineyard with a family in Bordeaux, France. “I literally did everything, from tending vines at 5am to hand-bottling over 3,000 bottles of wine,” Matt said. “This was my first exposure to both the wine business and entrepreneurship.”

During this time, Matt really studied the production process. “I took the opportunity to learn more about the state of the wine industry itself and the gaps in the market,” Matt said. “The company I worked at was very small, so they would send wine samples to industry and trade partners instead of entire bottles. I was intrigued. How could I bring that same experience to consumers in the USA?”

Matt was so enamored with this question that his break from corporate life became permanent. Instead of going back to New York and looking for a new job like he’d planned, Matt decided to start a business.

The Beginnings of Entrepreneurship

Matt began by talking with his peers. Was the idea of selling smaller portions of wine at retail, something typically reserved for restaurants and bars, something people would actually be interested in? Turns out, it was. “I was blown away by the response!” Matt said. “Everyone was interested and actively asking to purchase if I could make it available.” Since subscription boxes were quite popular at the time, Matt decided he’d test them out, but with wine.

Instead of returning to New York, Matt moved to San Francisco to be closer to the wine industry in Napa Valley and the startup hub in Silicon Valley. Once there, he kicked off the preorder campaign for VINEBOX, the name he’d chosen for his new company. Within the first 30 days, VINEBOX sold over 1000 boxes, all without an advertising budget. Sales were made solely through word of mouth. He shipped the first boxes in January 2016, and at the same time, was accepted by the YCombinator, a prominent American seed accelerator.

What are Vinebox & Usual?

VINEBOX focuses on discovery and education. Subscribers are sent sample sizes of various wines each quarter so they can ‘try before they buy.’ “VINEBOX gave members the ability to explore the world of wine and discover taste preferences without committing to a full-sized bottle,” Matt said. “It teaches newcomers about wine through drinking it. 

Because they work with wine producers all over the world, Vinebox is an excellent source for wine aficionados as well. There are many opportunities to try out wines otherwise unavailable. “At the end of last year, we curated a vertical of Barolo, three different vintages back to back, which is a truly rare thing,” Matt said.

Usual, Matt’s second wine company, was born out of VINEBOX. Customers mentioned that they loved having a glass of wine at the end of a long day but didn’t want to open a full size bottle because it often went to waste. Matt, realizing there were no high quality, by-the-glass bottles of wine on the market, felt he may have just struck gold.

Although Matt knew the idea was a good one, he was having some trouble with logistics. How should he contain the wine? Wine oxidizes as soon as it’s exposed to air, and figuring out how to bottle it in smaller containers while ensuring no oxygen entered was no easy feat. Matt considered using cans, but found that it was difficult to compete with the overpowering taste of aluminum, not to mention the preconception of ‘cheapness’ that comes with wine in a can. After some trial and error, with the help of world-renowned industrial designer Karim Rashid, Usual ended up with the perfect solution. They decided on a compact glass bottle shaped like a laboratory flask. And with that, Usual was created as your go to 6.3 oz glass of wine at the end of a long day, no uncorking required.

Usual launched just over a year ago, and the response has been overwhelmingly positive. At first Matt considered it a fun side project, but it’s now a full blown second brand.

What Sets Vinebox & Usual Apart from Other Brands

Matt prides himself in his determination to keep the wines they produce free of artificial ingredients and added chemicals. “All of our wines are super clean,” Matt told me. “Just made from grapes, water, and sunshine. No additives of any kind.” Matt went on to explain that sugar is actually added to lots of other wines on the market..

Matt is proud that the wines he works with all have zero grams of added or residual sugar, so they’re much healthier than others on the market.

According to Usual’s website, they care a lot about how the grapes are grown, too. “Our wines are made in small, sustainably farmed batches,” it reads boldly on the front page. “The grapes are curated from the healthiest, tastiest crops each season.” It was clear from our conversation that this was of utmost importance to Matt when he was creating each brand.

Overcoming Challenges & Finding Creative Solutions

Although both Usual and VINEBOX are thriving now, Matt hasn’t gone without his fair share of obstacles. “How are we getting the best vineyards across the world to believe in a brand that doesn’t exist yet?” Matt said. “And then, how do we actually get those wines to our customers?” To solve this, Matt spent a year visiting vineyards in Europe to gather advice and support from different producers and manufacturers.

Shipping was another tough egg to crack. Since the bottles are glass, there were instances of breakage while in transit, which was a huge concern. “The truth of the matter is that customers don’t differentiate brands from shippers anymore,” Matt said. Meaning, even if it was the shipping company’s fault, buyers would blame VINEBOX or Usual. “We’ll get one star reviews because the product arrived broken, and told that we should never use that service again,” Matt says.

Luckily, Matt has been able to put an end to this for the most part. When damages do happen, Matt relies on excellent customer service and a generous replacement policy to mitigate any negative feedback.

Responding to Negative Feedback

When Matt does receive a bad review, he has a protocol to follow. “Be transparent,” he says. “There are going to be issues no matter what you do.” He actually loves one star reviews because they allow him to address any issues publicly. “People want to see authentic reviews,” he says. “Most users don’t care about 5-star reviews. They want to see what went wrong and how that relates to them.”

Although a negative review may sound disheartening, Matt is actually quite positive about it. He believes the best approach is to apologize publicly. “Most of the users come back after that and thank us for our reply,” Matt said. “Then, we offer to send a replacement shipment.” 

Users are often satisfied and ask to change, or even remove, the review. Oftentimes, that same customer will order something else, and leave amazing feedback for that. “This way,” Matt says, “We take what could have been a negative situation and use it as an opportunity to turn them into an advocate.” Even if the customer decides not to order anything else, it’s still important that they received great service. In this way, the former customer may still recommend VINEBOX or Usual to their friends.

A Big Reason Behind Matt’s Success & Using SMS for Business

One of the key secrets to Matt’s success is his willingness to interact with his customer base. Why bother guessing whether something might sell well when you can simply just ask? 

“Wine is about people and their enjoyment,” Matt said. “We are only successful because we’re asking people what they want and how we can provide that to them.”

As mentioned above, Matt puts a lot of emphasis on customer service. “A huge part of our initial investment was to ensure we responded to inquiries in a timely manner,” Matt said. “It’s a balance, how much of an investment you spend to ensure a shorter response time.” Matt is always looking to solve customer problems in the easiest way, which often means using texts to communicate.

To Matt, texting opens the door for more real and authentic conversations with the user. “It feels friendlier, which makes the discussion more honest,” Matt told me. “The customers will give you more appropriate feedback about what they actually want. For example, when we were looking to launch a new product, we went to our existing customer base and just asked them what they liked.” The responses were immediate and unanimous: sparkling wine. This allowed Vinebox to create a product they already knew would sell.

SMS makes things easier for customers as well, as they can simply send messages to ask questions about shipping, reordering, or pairing recommendations.

Matt recommends proceeding with caution, though. “With marketing, you have to be extremely careful,” Matt says. “Text is still a bit of a safe space, so if you get a blind text from a brand you haven’t engaged with, it can feel deeply invasive and more negative than positive.” So, Matt doesn’t send any advertisements unless the customer reached out first, and recommends that other brands do the same.

For other businesses looking to start using SMS as a line of communication, Matt suggests Save My Sales (or, fittingly, SMS for short).

What's Next for Vinebox & Usual

Matt has some exciting projects coming up over the course of the year. What’s he (and his customers) most excited for? “The Brut is coming back,” He said. “It’s one of the most anticipated products from our audience! We also have a couple new products coming out. I can’t say exactly what they are, but if you’re a Usual customer, they may be just what you’ve been asking for."

Matt also plans to continue improving both Vinebox and Usual, and work to spread the word on the importance of ingredients in wines. “We’re always focused on building better wines,” he said. “People are obsessed with what they’re eating and the ingredients in food and skincare, but all of this hasn’t trickled into alcoholic drinks yet. We want to make people aware of this, because a lot of people don’t even know what’s in the wines they’re drinking.”

Luckily, Matt has made it clear what’s in the wines he sources for Vinebox and Usual, or rather, what isn’t. Matt hopes clean and sustainable wines will become the new norm in the industry, and is happy to be one of the businesses spearheading it.

Ryan Chatterton Editor, Content Strategist, Digital Nomad, Coworking Influencer, Lover of Wine & Tacos