Alright – so today we’ve got the honor of introducing you to Gary Saperstein. We think you’ll enjoy our conversation, we’ve shared it below.

Gary , thanks for joining us, excited to have you contributing your stories and insights. Can you talk to us about a risk you’ve taken – walk us through the story?

I would venture to say that the biggest risk I took was when I made the decision to leave the restaurant business and start my own LGBTQ+ Tour & Event Company, Out In The Vineyard.
Hospitality has been my whole life’s career starting out as a busser in college then moving on up to a server and then General Manager in restaurants. It just felt like a natural fit for me.

After 25 years in the business I was starting to lose my passion for the industry. Once you lose your passion for this type of work it is time to move on, in my mind. Fortunately at that same time I started to see an influx of LGTBQ+ Tourism in Sonoma Wine Country, where I reside along with growth in the gay population in the region. At the same time I wondered why no one was talking to our community. Hence, Out In The Vineyard was born.

I was risking everything I had known and felt comfortable with to finally strike out on my own and do something that no one else was doing. It was definitely stepping into uncharted territory.

Fortunately, due to my work in the restaurant industry I had a lot of contacts, people I had worked with for years as well as having a wonderful reputation with the public, being the face of the restaurant I was managing. Along with that it was 2008 and we were in the midst of a recession. Little did I know that these 3 factors would work in my favor.

Having the contacts opened up doors while I had a community that stood behind me and was willing to help anyway that they could. It was then I learned how important connections were along with a (good) reputation. The timing worked out as businesses also had to look outward and try to reach and market to every niche group that they could to help increase business. There I was on the sidelines saying, “Would you like the gays?” Everyone’s response to that was a resounding “yes!”

Still it was a very scary time in my life. Leaving my job and a paycheck and heading into the unknown.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I grew up in New York but made the move to Sonoma Wine Country 30 years ago in 1994. What made me a successful front of house manager in the restaurant biz was my hospitality skills. They came naturally to me and is something that I carry with me till this day.
The industry also let me be myself, a proud out Gay man. Being so fortunate I always felt the need to create community and bring people together. There is nothing I like more than community and connection and that is so what Out In The Vineyard is about; creating experiences for people that will create memories for people.

The signature event for Out In The Vineyard is Gay Wine Weekend now in it’s 13 year. It is the only 3-day lGBTQ+ Wine Festival in the world. It brings in people from all around the country (and internationally) to experience Wine Country. It is this event that I am most proud of as it has grown from literally nothing to a well-renowned event for our community. I love bringing people together year after year to not only experience Sonoma Wine Country but to make lasting friendships and even some relationships. From Winemaker Dinners, to Wine Tours, a Drag Queen Brunch and Wine Auction to the signature event of the weekend, The Twilight T-Dance, the weekend is for wine novices and connossieurs. It brings people together in one of the most iconic and beautiful settings in our country.

Can you share one of your favorite marketing or sales stories?

In 2019 I was starting a new event for Out In The Vineyard called Pink Sonoma. An all day Rosè Wine Tasting event. The event was taking place at a beautiful estate event space in Sonoma. The establishment was donating the space for the event. A few months before the event was to take place the establishment was sold. Upon hearing this news I immediately reached out to the company and was informed that everything was still a go. No issues with the new owners.
Then 3 weeks prior to the event news broke that the new owners of the establishment were anti-gay and that the owner’s wife had a lot of negative and nasty comments on her FB page. Immediately the page was taken down but the media got hold of it and the news spread far and wide. Here I was about to do a gay event at their establishment. People were reaching out to me on social media asking and telling me that I should move the event.

At first I totally agreed and started to look for a new event space. Unfortunately here in Sonoma there are not many spaces that can accommodate 300+ people. Also the space was being donated and if I had to pay for a space that would put me in the red. That part wasn’t as important to me but unfortunately in the short time frame that I had available I was not able to secure another space for the event.

I reached out to a friend who had worked in PR Crisis to get advice. That was a huge help as I was able to put out a statement to the community fully acknowleging what was going on and how I was not able to secure a new location for the event but at the same time no money was exchanging hands with the new owners, the establishment was still being donated. I let the community know that I was now going to be throwing a big old Gay party at their establishment whether they liked it or not (which they didn’t!) With that statement the community rallied around me and ticket sales went even higher. The event was a huge success and literally was the last gay event held at that location.

Any insights you can share with us about how you built up your social media presence?

I say to this very day that I built my business on social media. The year was 2008 and FB was this new technology that had just launched a few years prior. It was a great way to reach people far and wide and for very little cost. At that time they didn’t have the algorithms in place that they do now so it was easy to target your demographic.
It was amazing to see how well it worked and that people were responding to something so new and different. No one had heard of a Gay Wine Weekend but the demographic for our community is one that loves to travel, loves food and wine and likes to be with community. It was vital that we get the message out that we were offering the best of “our” Wine Country to our community and it resonated with people. Again, timing is important and social media was there when starting Out In The Vineyard and Gay Wine Weekend.

Social Media is different nowadays. They are making it more challenging to reach your audience and you have to pay more, yet still it is quite affordable. Images are so important. You want what you are going to share with people make them stop and look. I always say I want people to look at the image and say to themselves, “I want to be there!” If you can do that people will respond to your posts.

Contact Info:

• Website: https://www.outinthevineyard.com/
• Instagram: outinthevineyard
• Facebook: https://www.facebook.com/outinthevineyard
• Linkedin: https://www.linkedin.com/company/1207089/admin/dashboard/
• Youtube: https://www.youtube.com/channel/UCU86DtIyskOS3-uMZinrtXg

Image Credits

Photos by Aryk Copley Photography