How Sailor Guevara Built a Pandemic-Proof Cocktail Experience Company | Founder, Sailor Guevara Cocktail Co

Sailor Guevara went from bartending in fine dining restaurants to becoming an award-winning brand ambassador and then reinvented her career in the middle of the pandemic. Today she runs a virtual event fulfillment company, leading immersive cocktail tastings and shipping curated kits to clients across the country. In this conversation, Sailor shares how her Greek immigrant roots and love of origin stories shaped her passion for food and drink, the life events that built her resilience, and why she believes in designing a business around your values. We talk about adapting to change, the importance of community, and how to collect the right people to fuel your success. Chapters 00:00 – Meet Sailor Guevara 03:15 – From brand ambassador to virtual events 07:10 – Creating immersive experiences in a box 10:45 – Early days in hospitality and the path to bartending 15:40 – Why origin stories matter 19:40 – Getting comfortable with failure and convictions 24:30 – Letting go of social norms and finding your own path 28:15 – The role of community in success 30:35 – Helping the next generation succeed 34:10 – Choosing where to live 38:55 – Balancing risk-taking in business and relationships 43:50 – Staying grounded while growing fast 46:50 – Where to find Sailor Guevara The Powerful Ladies podcast, hosted by business coach and strategist Kara Duffy features candid conversations with entrepreneurs, creatives, athletes, chefs, writers, scientists, and more. Every Wednesday, new episodes explore what it means to lead with purpose, create with intention, and define success on your own terms. Whether you're growing a business, changing careers, or asking bigger questions, these stories remind you: you're not alone, and you're more powerful than you think. Explore more at thepowerfulladies.com and karaduffy.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices