A DRINK WITH SAILOR GUEVARA
By Maia Merrill Gosselin
Sometimes, all it takes is a lucky break to open the door to your career. For Sailor Guevara, that break came in the form of landing a coveted gig on a busy bar back in the 90s. At the time, it was a means to an end while in school, but Sailor had a natural aptitude for the hustle of bartending and a flair for mixing drinks. This was the era of Stoli Raz, oversized Cosmos, and Zima, but what really piqued Sailor’s interest were the “other bottles”, the ones gathering dust that no one seemed to know about, much less use. Her innate sense of curiosity led her to ask questions and begin delving into the history of spirits and cocktails. With that came a real thirst for knowledge and it wasn’t long before she realized there was a genuine opportunity to make this industry her profession.
Today, Sailor is an established spirits expert with a highly accomplished resume. Over the years, she has parlayed her varied interests into a successful career that includes mixology, consulting, distilling, and education, among other roles. She is a noted whiskey authority, influencer, and champion for women in the industry. In fact, there’s not much she hasn’t done! I had the chance to catch up with Sailor recently for a terrific conversation. We covered a range of subjects, including challenges the industry is facing, her philanthropic commitments, and the resurgence of classic cocktails (Pink Squirrel anyone?). Well-informed, dedicated, and passionate . . . when Sailor Guevara talks, people listen!
MAIA GOSSELIN From bartender to noted spirits expert, you’ve accomplished a great deal and carved out your own niche in this industry. When did it go from a job to a career?
SAILOR GUEVARA As with most stories, I began working in restaurants in high school and college for extra money. I did just about every job possible. Finally, I made my way to the coveted cocktail server spot, which was a big deal in the early 1990s because the shifts were shorter and the money was better. I was living in the Midwest at the time and bartending was very much a boys’ club, so I didn’t think I had a chance. Lucky for me, I got a shot behind the bar, much to the head bartender’s annoyance. I saw it as a pinnacle spot and respected the profession. I fell in love with mixing things together to create new flavors, learning about the products and the engagement with guests. It turns out that I had the perfect personality and drive. I was fast, had a strong work ethic and a great memory. Even after graduating college and trying out corporate life, I kept bartending and finally fought against societal pressures and my family’s expectations. I decided the bar world was where I aspired to be.
MG Where did your interest in cocktail history and lore stem from?
SG I got my start in a Mexican American chain restaurant. We were slinging terrible Margaritas, beer, and shots of whatever was in fashion. I wanted to know why we didn’t use 50% of what was on the back bar and what those dusty bottles were for. Some of my colleagues knew what they were but didn’t seem interested in the vermouth and liqueurs that we kept stocked for the off chance someone ordered a Manhattan or a Martini. I wanted to know more, so I began asking the distributor reps when they came in (this was pre-internet) and hunted down cocktail books. The European brands were great at telling their histories and stories in the print material that reps would share with me, so I became hooked and wanted to know everything about every spirit. It was an obsession for a while.
MG Consultant, advocate, podcast host, author…you wear a number of hats! How do you manage all of them and is there one in particular where you invest the majority of your time?
SG Being independent of full-time work for a brand or at a bar or restaurant, I think you have to throw yourself into many projects. I was a brand ambassador for many, many years. After 2020, I knew it was time to hang up my ambassador hat and forge out on my own. I wasn’t sure what I wanted to do and what would stick, so I threw the spaghetti against the wall, so to speak. I have a real affinity for American craft brands and I believe our craft industry is vital to the health of the American spirits industry. And I am shocked every time I hear of a new craft brand breaking ground or hitting the market.
I can’t believe sometimes that people still do it. It’s such a tough business. The spirits industry lacks parity; thus, craft brands struggle. I have spent a lot of my career advocating for the underdogs and I consult on a project basis for many emerging brands because I want to help them. I have all of this experience and knowledge, it feels good to pass it on and make running their business a little easier. So consulting has been my bread and butter for the past few years and more recently I have written for several outlets in the industry which I am enjoying immensely. I am not yet at a place where I can get opinion pieces published. That is my next dream. I have a lot of opinions. But I am enjoying writing about cocktails, sharing the stories behind spirit brands, and offering advice on creating successful distillery bar programs. It’s very rewarding.
MG You are a renowned whiskey expert. How did you become niched into the category and where did you acquire your knowledge?
SG Accident or destiny decided it. Early in my career, I focused heavily on wine. I lived in Europe for years and pursued wine education, which was an incredible experience. When I came back to the US, I had my sights set on climbing the Sommelier ladder and received some sage advice from an industry mentor. I took some time off to decide which direction I wished to go. I spent time on the bourbon trail in Kentucky and was hooked. I became the ‘whiskey lady’ in bars that I worked in and eventually shifted gears and began my career in brand work. At some point, I ended up working in distilleries and since they were small businesses, I learned so much. I could work in many jobs and gain an education in production. That was the last piece of the puzzle for me. I could convey the brand story and teach people how to smell and taste whiskey from a firsthand perspective.
MG More and more women are establishing themselves in the whiskey industry. Cheers to that! What do you attribute this to and where are you seeing the most growth?
SG It’s about time and long overdue. The lack of diversity and equity in the American spirits industry, especially whiskey, is unacceptable in 2025. So many amazing people have been tirelessly working on curing this issue, and I am proud to be one of them. At the first whiskey tasting that I hosted, I was the only woman in the room, which would be the norm for years to come. The last time I held a tasting on behalf of a brand, there were only four men in the room, and half of the audience were people of color. That is a genuine change, but we have to do better because my experience is not the norm. Let’s be honest, women have always been in the whiskey industry. Margie Samuels of Maker’s Mark, Bessie Williamson of Laphroaig, plus all the women whose names didn’t make it into the annals of history that were the backbone of whiskey brands and production. Women have never been invited to drink whiskey; women have never been the target customer. People of color faced a similar situation until recently. To ensure that we have equity in any industry, you must have women and people of color in leadership and ownership positions. We have to fight for change like this, and that’s what we have been doing for over a decade inside the craft space. And think to yourself, when was the last time you saw marketing and advertising for American whiskey that was directed at a female consumer? But in the craft space, I could fill a shelf today with female-owned/led brands with emerging POC brands right behind them.
MG There has been a lot of change in the spirits industry over the last few years . . . some good, some bad. What are some areas that are positive and where do you have concerns?
SG Adding to my answer to the former question. Women and people of color in leadership positions in bars, restaurants, and brands is the only way we will make the inroads that we need. The discussion about mental health and addiction in our industry post 2020 is important and positive, but we all know that our industry is still struggling to come back from the pandemic. Nothing is the same, which is good in some ways and bad in others. I want people to look at our industry and see a future. I think hospitality and drinks is one of the best industries in the world with the most creative and fascinating people. The question is: how do we offer young people solid education and a future with the protections and benefits that they might receive in other sectors? Unless they are corporate, very few can. I worry that we’re returning to a time when our bars and restaurants are full of people lacking industry education, ambition, and commitment. This statement isn’t to place blame. I have been a bar owner. It felt impossible to make ends meet in this economy.
MG You founded Spirit Craft Social in 2022 focusing on emerging and small spirit brands. Can you describe how you operate? Where did your commitment to this particular segment stem from?
SG What I heard most from smaller brands was that with the lack of access to distribution, small marketing budgets and being overwhelmed with operating duties, they don’t know how to leverage digital marketing and social media. Digital marketing is a necessary tool for any business that can’t afford traditional advertising and lacks market access, so I wanted to add that piece to my consulting services. I do the analysis and strategy which I love.
MG Talk about your role with Good Deeds Spirits. What are some of the charities they work with?
SG Giving back and being a positive force in my community are important to me. I spend a lot of my time on nonprofit boards and helping wherever I can. A few years ago, I became one of the first mentors for the American Craft Spirits Association STEPUP Internship program. STEPUP was launched in August 2020 to bridge the gap between an interest in and gaining skills to succeed in a segment of the alcohol beverage community. I found the experience so gratifying. My intern graduated from the program and has since become the head distiller at a very reputable distillery in the Chicago area. To continue supporting the program, I accepted the offer to become Executive Director of Good Deeds Spirits, a non-profit spirits brand, in 2022. We have just released our second product, which is a bourbon and rye blend that was blended by an all-female team. I plan to continue releasing one product a year and will donate the proceeds to various charities besides STEPUP.
MG The American Distilling Institute’s International Spirits Competition named you its Top Spirits Influencer . . . congratulations! How has this role developed for you? What exactly does an influencer do?
SG It’s odd to think of myself as an influencer. It’s such an honor to be chosen by my peers in the industry. I use my influence wherever I can to focus attention on craft brands and brands with diverse leadership. When I create a bar program or a brand asks me to develop a menu for an event, I ensure I am suggesting the brands that need the exposure with good people behind them and that make great products. I have a lot of museums and nonprofit entities from all over the country that ask me to help connect them with brands for events or put together their event bars. It’s not always easy because of the distribution issues, but I always seem to find someone I know who can call a friend and get it done. Sure, I have a lot of social media followers, but for me, that’s not what makes me an influencer. I have people subscribed to my newsletter who have been following me for over ten years and who trust me. I love sending out emails telling them about my new favorite gin or a distillery that they need to know about or a bar that is doing special things. I still host virtual events with mystery boxes of my favorite things and they continue to sell out. So to me, it’s the connections and relationships and being genuinely joyful about the products I promote and share.
MG Any fun or interesting cocktail trends you’re keeping an eye on?
SG You might have to be of a certain age, but I love seeing a return to a lot of cocktails from my lifetime that went out of fashion. Recently, a friend’s daughter was eager to tell me about this new cocktail that I needed to know about because it was amazing. She’s 24. The cocktail was an Amaretto Sour. I did my best not to laugh. I’m also loving the resurgence of Johnny Carson cocktails: the Pink Squirrel and the Grasshopper. I read somewhere that Johnny Carson loved Grasshoppers and Pink Squirrels. I don’t know if it’s true, but I love the idea. So I will forever call that decade of cream cocktails by his name.
MG Favorite destination to travel to for cocktail culture, distillery visits, or just for enjoyment?
SG I was in the Pacific Northwest for many years and I am really into what they are doing out there. Their approach to flavors and the symbiosis with local ingredients and food and drink is interesting and unique to the area.
For distillery visits, I would say go to the Southwest, New Mexico in particular. They are building an entirely fresh approach to terroir spirits and it’s really exciting.
MG And finally, as you contemplate an end-of-the-day libation . . . what’s going to be in your glass?
SG I know I should say whiskey and normally I would. But this year, I have decided that I must wage war on the disrespect for vermouth in the U.S. I thought we were on our way 8-10 years ago. I felt that finally Americans were getting it; bartenders were putting in good work. And when American vermouth began hitting the shelves, there was me in the aisles like I just scored a touchdown. Then, VINEPAIR published an article on February 6th by none other than Robert Simonson titled, “Even the Great Martini Revival Can’t Save Vermouth”. I won’t let it happen. So, I am drinking a glass of lovely vermouth, chilled and neat.
PHOTOS • DAWN VICTORIA GILMORE
