We recently connected with Casleah Herwaldt and have shared our conversation below.

Hi Casleah , thanks for joining us today. What’s the backstory behind how you came up with the idea for your business?

Before the pandemic, I was working in healthcare part time and was trying to break into the wine industry. I was fascinated with wine so much that in between patients, I would be reading the wine bible and working on my wine focused instagram. As my instagram grew, I started partnering with different brands to help bring awareness to my audience. I kept picking up little side hustles in wine such as hosting in home wine tasting parties. My client base grew quite large. One day, a brand I connected with on instagram let me know that he was looking for a sales person. So I started selling his wine for my private events while still working in healthcare. When the pandemic hit, I was one of the first people to jump on to zoom for virtual happy hours. I hosted one for St. Patricks Day, just days after the lock down began. I was featured in the Huffington Post for “Best Virtual Happy Hours to Attend.” As the pandemic went on, a few people asked me how they could get some wine. Remember during these times, online wine shopping wasn’t as prevalent and we were all afraid to go to the store. I said that I sell wine and could ship it to them, and in fact, we could log on to zoom and taste the wines together. My friends had such a blast at our little zoom tasting that I started offering this idea to more friends. Soon enough, I connected to a friend of a friend who was in sales for Google and her husband was in sales for Snapchat. They attended my tasting and loved it. They asked if we could create a flyer and promote it to their companies for a fun team building activity during lockdown. I quickly jumped on this opportunity. I reached out to the brand I had been selling to see if we could package the wines in 3 packs and ship them out all over the country. I ended up being so booked solid with tastings that I quit my healthcare job, started an LLC and eventually sold the brand out of wine!! The idea all stemmed back to being open to possibilities, being creative and most of all paying attention to the needs of people around you and coming up with solutions to improve other’s lives. Now, flash forward a few years, so many wineries are offering virtual tastings and there are so many small business’ built around virtual tastings that are now going back to in person tastings. This idea was easy for me to run with because wine is my passion and I love creating a fun environment where everyone feels comfortable to enjoy themselves.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My name is Casleah and I’m originally from Michigan, but live in Redondo Beach, CA now. My dad actually grew up on a vineyard so wine has always been apart of my life. It wasn’t until I had moved to Kansas City and visited a wine bar there. The sommelier walked me through the tasting notes of a Cabernet Sauvignon from Sonoma and from that moment on I was hooked. I got connected to a local wine shop that was offering events, classes and tastings. I was there so much that they offered me a job. I started working there nights and weekends while working in healthcare during the day. I began to learn about wine courses and certifications. I signed up for the Court of Master Sommeliers Introductory Course. Then I moved to California and began my in home wine tasting business. I had a brief stint of working in a restaurant as a floor sommelier. That’s a fun story of a lady I met on an airplane and hired me on the spot. I continued to wine courses and became a level 2 Certified Sommelier through the CMS. I also took Wine and Spirit Education Courses (WSET). I’m currently enrolled in their highest level, called the Diploma. Given I pass this next exam, I’ll be all done!

My business is called By The Stem, like you hold your wine glass by the stem. It was created for my virtual wine tastings and has evolved over the years. I created my own wine label called Casleah Wine made from Pinot Noir from the Petaluma, Sonoma area. I made a red and a rose wine. I also had a wine club where I send monthly wine shipments and connected with the members on zoom monthly. I currently have a full time job selling wine for Regal Wine Company so some of my business aspects have scaled back a bit. My favorite part of my business is working with brands through instagram and through my blog to help bring awareness to small production, family owned and sustainable wineries. I also love helping the general public to be more educated and confident when shopping for wine and choosing wine off of a list.

I’m most proud of how I’ve been able to follow my dreams over these last few years. Although I do miss taking care of patients sometimes. I’m so so happy in the life I’ve created through wine. Wine brings people together. I’ve always said my dream job is meeting people and introducing them to other people. Now I get to do that for a living through wine.

Have you ever had to pivot?

My business is a story of pivoting! Through pandemic things were constantly changing and we were constantly adjusting. I actually switched vendors for wine for my virtual tastings 3 times. The first two because I literally sold them out of wine.

The wine club is another great example of pivoting. It was very much a trial and error project. Although I had a group of loyal members, I realized it was going to take a lot more time and some money in order to make it super profitable. I realized I needed to prioritize other things and had to make the tough decision to end the wine club.

And even with Casleah Wine, A lot of decisions had to be made very quickly. A lot of people don’t know this, but the first batch of my rose was all labeled by hand!! Flexibility is the name of the game in entrepreneur life.

What’s a lesson you had to unlearn and what’s the backstory?

I was raised in a small town where the majority of people get married and have kids young. They buy a house, the husband works a comfortable, steady job and the wife might work, but most likely stays home with the kids. I’ve married 12 years now, and I still don’t know if kids are in our future. I needed to learn that everyone is on their own journey and that it’s okay for my journey to look different. Switching from healthcare to full time working for myself was a big step and a big risk, but it was so so worth it because I was following my passion. There were definitely times when I had no idea where my next check was going to come from. Or the demands of the customer just seemed to big to come through on. The biggest lesson for me was trusting that when I follow my passions, that is enough to make me successful. Because at the end of the day when you love what you do, it doesn’t feel like work.

Contact Info:

• Website: https://bythestem.co/
• Instagram: www.instagram.com/casleah
• Facebook: https://www.facebook.com/bythestem
• Linkedin: https://www.linkedin.com/in/casleah/

Image Credits
Chasing Creative Sylvanus Leone