Interviewing With the Wind: South Dakota’s Largest Vineyard and Winery

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In 2014, Lisa and Jeremiah Klein established With the Wind Vineyard & Winery and the family business has grown substantially ever since. We spoke with the couple about the wine market, their experience with one of the top website builders, Squarespace, and the successes they’ve had since starting out.

After turning their energy toward planting vineyards, fermenting wines, and building facilities to host guests, the Kleins now operate across six and a half acres of active vineyards – equalling nearly 5,000 grapevines!

With a team of over 20 employees, Lisa continues to manage wholesale and on-site sales, while Jeremiah manages the winemaking and vineyard operations.

Read on to find out more about With the Wind Vineyard & Winery…

“We chose to create our own website because we needed a way to reach people online.”

A white house surrounded by land and vineyards
With the Wind Vineyard and Winery has six and a half acres of vineyards.

Joining the Wine Market

“The wine industry is a very cut-throat place, and our brand is unique to most vineyards and wineries. While we cater to all wine drinking, ranging from sweet to dry, our most popular wines are semi-sweet to sweet. Within the Midwest wine market, we are unique because we produce a line of sparkling wines. They have become our most popular wines across the board!

We did not have any financial investors [when building the business], but we did hire one employee in the very beginning. Other than a few contractors to execute some of the building processes, everything was built from the ground up financially and physically. We really did most of the plumbing, electrical, flooring, drywall, fixtures, painting, etc. It was an incredibly hard but rewarding process, and now we are so thankful as it allows us to be in the stage we are in.

Our business has truly taken off with growth in every direction.

We started with three employees including me and my husband. Now, we have grown to a team of over twenty employees spreading across every facet of the business. We are penetrating new markets in the Midwest wine industry, and we recently earned the title of South Dakota’s largest vineyard and winery!

Line up of wine bottles by With the Wind
With the Wind produces a wide variety of wine.

Running a Family Business

“While there are definitely difficulties, it has been amazing because we have gotten to be stay-at-home parents as our business is located below where we live. Our kids have learned the value of hard work because they have participated in every step of the journey with us. To give balance to work life and home life, we highly prioritize family time and getaways. Now, our daughter and son-in-law have returned to join in the family venture, and we love that this has always been a family business.”

A Passion for Work

Lisa: “I love crushing my goals every day, and I love that I am constantly learning new things while overcoming new challenges. One of the best parts about my work is building relationships with stores and customers on the daily.”

Jeremiah: “Between shipping and wine club, on-site visitors, and events, my job is so fun because there is so much variety and activity. From month to month, there are many different focuses from wine club and seasonal events to weddings during the summer, as well as vineyard requirements, and the different wines being made. Every day is so busy, challenging, and fun. Every day is very different!”

Celebrating Customers

“We have guests who have known us for years and who have built strong relationships professionally and relationally. We keep very close contact and personal relationships with almost every business we work with! This is one of our core values within our business.

Our mission is to bring people together to joyously celebrate relationships and connection! We love being a part of that and value our strong customer base immensely.”

Large crowd of people sat down within a fabric gazebo, raising glasses of wine
With the Wind holds events throughout the year to help build customer relationships.

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Things Are Really Grape: Business Successes

“From our establishment in 2014, we have always been a business built from our own immediate family. We have growth and have been very blessed with expansion capabilities to buy another eighty acres of land for vineyard, grown to sustain over twenty staff, and have recently undergone multiple vineyard, building, and product expansions.

With the Wind is currently producing about 5,000 cases per year and is set on track to increase to 10,000 cases within the next few years. Additionally, with our latest planting, we now grow almost 5,000 grapevines.

Our most recent success story is one of our favorites. This spring, with the addition of our newest vineyard, we have earned the title of South Dakota’s largest vineyard and winery! We are very proud of the work we and our team have put in.

Numerous accounts over the years have also been so fun and satisfying as we have become bestsellers in many of our stores, competing with national and worldwide brands!

It is the most amazing feeling when customers put back a national brand on the shelf after tasting our wines during in-store tastings.

One very proud moment for us was when one of our retailers ordered a sixteen-case purchase for an event back in our first year of business. We were so proud, and we framed the handwritten note order.

In the past six months, we launched our first sparkling wine, and it was ranked as the top seller at one of our retailers. It beat out international brands and was a very proud moment for us!”

Overcoming Challenges

“Truthfully, our greatest challenge has been our rural geographic area. We are located in the northeast corner of South Dakota, and it has both its strengths and weaknesses. While it is definitely rural, people are amazed at the peacefulness and the natural beauty that surrounds our area. We ship our wines all across the United States and are happy to be able to have the beauty of our area but still be able to access a customer base through shipping!”

Building a Website With Squarespace

“We chose to create our own website because we needed a way to reach people online. We originally had a website developer, but after that fell through, we needed a platform that would work for a novice to use. Squarespace’s professionalism appealed to us more than other platforms such as Wix. It had so many beautiful templates, and we have never regretted using Squarespace for a second.

We are currently on the Business plan because it is a good middle ground for us. It is cheaper than other plans but has all the features we need!

Not being an expert, there were certain things I was not aware of that we didn’t do right in the beginning. We have fixed those issues more recently and have dove into improving our SEO as well. As for managing and running events, we have found that many of our customers discover our upcoming events through the listing on our website which has been very helpful.

As we have hired marketing staff, Squarespace has seamlessly fit into our business even more. However, I would have loved to learn about SEO from Squarespace earlier in my journey. I find that part of the website builder is a little intimidating still.”

Scalability of Squarespace

“We feel we are still learning and perfecting our website. However, we are always looking for new innovations that will help us scale our business further.

Know that you will probably continue to change and improve your website, and that is okay! 

Work on taking one step at a time, and be patient with the progress. The more you work at it, the better your website will be! It’s a learning process I think we all should learn.”

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Advice From the Experts

Lisa: “I think I would tell my younger self that everything will come together as it should. I would tell her to remember that all her prior life experiences will come into play perfectly when she owns a business. I would tell her to trust the process, and enjoy the journey knowing that everything will line up for the future!”

Jeremiah: “A financial strategy I will always live by is lean startup. We established With the Wind Winery with no help from investors, so we learned to be scrappy with our finances while still working to keep consumer perceptions as high as possible. Additionally, you have to learn as you go, from your market, products, etc. Stay flexible and listen to those around you. That has been our mantra that we always tell people.”

Future Plans

“We have many upcoming goals and future plans including installing a commercial kitchen for serving food this winter, doubling our production over the next couple years, planting another eighty acres of vineyard, distributing further into the Midwest as well as nationally, and preparing ourselves for the next generation to come in. We have a lot of goals and are excited to see where the upcoming stages take us!”

Written by:
emma ryan author bio
Emma’s been a Senior Writer at Website Builder Expert since 2022, having first-hand experience with website builders, such as Wix and Shopify, through hands-on testing and research analysis. Her work and expertise have been featured in Digiday, TechRound, Industry Today, and Digital Information World. Specializing in writing about website builders, ecommerce platforms, and hosting providers, Emma stays in the loop of industry updates by attending conferences such as eCommerce Expo and managing Website Builder Expert’s news articles.

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