Harvesting Success: The Rise of With the Wind Vineyard & Winery

Harvesting Success: The Rise of With the Wind Vineyard & Winery





With the Wind Vineyard & Winery


Since 2014, Lisa Klein and Jeremiah Klein founded With the Wind Vineyard & Winery. The family business has grown significantly. 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!

Business Operations

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…

Joining the Wine Market

“The wine industry has a lot of competition, and our brand is different from most vineyards and wineries. While we cater to all wine drinkers, 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. These wines have become our most popular across the board!

Building from the Ground Up

We didn’t have any financial investors when we started the business, but we did hire a single employee at the beginning. Everything was built from scratch, both financially and physically. We did the majority of the plumbing, wiring, flooring, drywalling, fixtures, and painting. 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 grown in every direction.

We started out with three employees, including myself and my husband. Now, we have grown to a team of over twenty employees, spread across all aspects 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!

Running a Family Business

“While there have been some challenges, it’s been amazing to be able to stay at home with our children because our business is located directly below where we live.”

Our children have learned to value hard work by participating in every step of our journey. 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 enjoy achieving my goals and learning new things every day. I also love the fact that I am always overcoming challenges.”

One of the most rewarding aspects of my job is the daily interaction with customers and stores.

Jeremiah says: “My job is fun because it is so varied and active. There is a lot of variety and activity between shipping and wine clubs, on-site guests, and events.”

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 busy, challenging and fun. Every day is very different!

Celebrating Customers

We have guests that have been with us for many years and have developed strong professional and personal relationships. We maintain very close personal and professional relationships with nearly every business with which we work! This is one of the core values we hold within our company.

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

With the Wind hosts events throughout the year in order to build customer relationships.

Business Successes

From our establishment in 2014, we have always been a business built from our own immediate family. We have experienced growth and were blessed with the ability to expand. We bought another eighty-acre vineyard and have grown to support over twenty staff.

With the Wind currently produces about 5,000 cases of wine per year, and is on track to reach 10,000 cases in the next few years. Additionally, with our latest planting we have almost 5,000 grapevines.

Our most recent success 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 all the hard work that we and our team have put in.

We have had many accounts over the years that have been fun and satisfying. We have become bestsellers in our stores, competing against national and international brands!

“It was a proud moment for us to beat out international brands.”

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 happy that we framed the order.

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

Overcoming Challenges

“Our rural geographical area has been our greatest challenge.”

We are located in the northeast corner of South Dakota, and it has both its strengths and weaknesses. Although it is rural, people are amazed by the peace and natural beauty of our area. We ship our wine all over the United States. We are happy to have the beauty of the area while still being able to access a large customer base through shipping!

Building a Website with Squarespace

“We created our own website to reach out to 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 was more appealing to us than other platforms like Wix. It had so many beautiful template options, and we’ve never regretted choosing it.

We are currently on the Business plan as it is a good compromise for us. It’s cheaper than other plans, but still has all the features that we need!

As a novice, I wasn’t aware of certain things we did wrong at the beginning. We have corrected those issues and improved our SEO. As we have hired marketing personnel, Squarespace has become even more integrated into our business. However, I would have liked to learn more about SEO earlier on in my journey. I still find the website builder intimidating.

Scalability of Squarespace

We still feel that we are learning and improving our website. However, we are always on the lookout for new innovations to help us grow our business. Know that you will likely continue to improve and change your website, and that is okay! Be patient and take one step at a given time. The more you work on it, the better your website will be! It’s a learning process I think we all should learn.

With the Wind Website Gallery

Expert Advice

Lisa: “I would tell her to enjoy the journey and trust the process. Everything will work out in the end.”

Jeremiah says: “A financial philosophy I will always follow is lean startups. 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’s what 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!

Additional Resources

Topic Resource
How to Sell Wine Online Our step-by-step guide will show you how to begin selling wine online.
How to Sell Wholesale Five simple tips to get you started.
Squarespace Pricing Which Squarespace plan is right for you?


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