Today we’d like to introduce you to Courtney Blake.
Hi Courtney, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
My interest in bartending actually began years ago when I was working as a server in college. I was always fascinated by the creativity behind cocktails—the way flavors, presentation, and experience come together. Even though bartending was something I wanted to pursue, I procrastinated on taking the next step for a long time. It wasn’t until 2023 that I finally decided to invest in myself and earn my bartending certification through BYOB Cocktail Services.
That decision changed everything.
I launched Pretty Tipsy in September 2023, and within that same month, I traveled to Charlotte, NC for my very first gig. From that point forward, the momentum never slowed down. By the end of 2023, I had already secured bookings for 2024. Throughout 2024, we completed 46 events—weddings, birthday parties, open mic nights, mocktail displays, mixology classes, real estate happy hours, and more. Each event helped shape who we are and strengthened our commitment to delivering a personalized, elevated bartending experience.
As we close out 2025, weddings have become our primary niche, making up about 90% of our bookings. I truly believe that leaning into branding and understanding our unique value is what positioned Pretty Tipsy for success. I’ve always been a creative at heart, and I use that creativity to make every detail count—from aesthetic drink presentations to themed bar decor. Our name, Pretty Tipsy, reflects exactly what we stand for. We don’t just want your drinks to taste good—we want them to look good. For us, it’s all about the aesthetics, the experience, and the details, because details matter.
Pretty Tipsy has grown into something I once only imagined, and I’m grateful every day that I took that first step.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I’ve learned that having strong customer service skills allows you to navigate the chaos with grace. The business side of bartending, especially the behind-the-scenes work, has taught me so much. I learn something new at every event, and I use those lessons to plan better for the next one or update my contract to ensure full clarity and protection for both myself and the client.
I think a lot of people look at bartending as, “Oh, you’re just making drinks—how hard can it be?” But it’s far more complex than that. For weddings, for example, you’re coordinating with planners and vendors to make sure everything aligns perfectly with the timeline. There’s extensive preparation required to ensure service is smooth, efficient, and stress-free for the client.
The day of an event starts hours before I ever arrive on-site. I block out 2–3 hours just for prep: cutting fruit garnishes, proportioning juices, organizing bar tools, loading supplies, and making sure everything is ready to travel safely. This prep is what makes our setup quick and seamless—because once you start setting up at the venue, guests will naturally gravitate to the bar and want something, which can easily slow down the process.
So no, it hasn’t been a smooth road. But every challenge has helped me grow as a business owner. Mastering the details, planning ahead, and staying adaptable are the reasons Pretty Tipsy continues to thrive.
Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
Pretty Tipsy is a mobile bartending company that focuses on creating elevated, memorable beverage experiences for events of all kinds. We provide professional, insured bartending services for weddings, corporate events, private parties, mixology classes, community events, and more. Our goal is simple: to make every drink taste as good as it looks.
We specialize in signature cocktails, curated drink menus, and aesthetic bar setups that match the theme and energy of each event. We’re known for our attention to detail—custom drink stirrers, themed menus, beautifully garnished cocktails, dry ice smoke effect, and bar presentations that feel intentional and cohesive with our clients’ décor. We bring creativity, professionalism, and personality to every event.
What sets Pretty Tipsy apart is the emphasis we place on creativity and aesthetics. I’ve always had an eye for design, and I pour that into every aspect of the brand, from the cocktails to the visual presentation. We don’t just bartend—we curate an experience.
I also want to give a special thanks to my amazing friend, Maryam, who has played a huge role in shaping the aesthetic of my business. She has taught me so much, and she’s the creative vision behind my brand photoshoot. We collaborate often, and as one of the top event planners in Charlotte through her business, Masterpiece Designs, her influence has been invaluable. Without her, Pretty Tipsy wouldn’t be where it is today.
I also want to highlight Aria Womble, owner of Purple Heart Designs. She brings all of my visions to life through our acrylic bar menus and customized drink stirrers. She’s also one of my bartenders and steps in to help whenever she can. Having a solid team has been such a blessing. Pretty Tipsy is not a one-woman show—it’s a collaborative effort, and I’m forever grateful for everyone who contributes to our success.
Brand-wise, I’m most proud of how strongly our identity has developed in such a short time. Pretty Tipsy has become synonymous with quality, creativity, and a memorable experience. Nearly 90% of our bookings this year have been weddings, which speaks to the trust and reputation we’ve built in the industry.
What I want readers to know is that when you book Pretty Tipsy, you’re getting more than bartending—you’re getting an experience crafted with intention. We offer full mobile bar packages, beer and wine service, bartender-only options, mocktail displays, themed cocktails, mixology classes, and custom drink menu design. Everything we do is rooted in creativity, professionalism, and a love for making people feel celebrated. Also, we travel throughout North Carolina – let us bring the bar experience to you.
Networking and finding a mentor can have such a positive impact on one’s life and career. Any advice?
Networking is everything in this industry. When I first started Pretty Tipsy, many of my clients came from Thumbtack, but now the majority of my 2025 bookings come from referrals, repeat clients, and word of mouth. Building genuine relationships has been the foundation of my growth.
One of the biggest pieces of advice I can give is to put yourself out there. Post your content—consistently. Content truly is king. I remind myself of this often, because every time I post regularly, the inquiries start rolling in daily. People can only book what they can see, so showing your work is essential.
Mentorship has also played a huge role in my journey. I personally took a mentorship program with Jasmyne, owner of Four the Aesthetics (formerly Mixy Chix in Atlanta, GA). I learned so much from her, and even had the opportunity to shadow her while she set up for an event produced by Lance Devereux in Charlotte. That experience alone expanded my knowledge, confidence, and understanding of the industry.
I also offer mentorship opportunities myself now, because I know how important it is to have guidance when starting a mobile bartending business. Sometimes all you need is someone who’s been where you are to help you avoid mistakes, navigate challenges, and grow faster.
Another major key to networking is connecting with event planners and venue owners. Align yourself with planners who match your brand’s style and energy, and work to get on preferred vendor lists at venues. These relationships not only build credibility but also create a steady flow of consistent, high-quality referrals.
Overall, my biggest advice is to stay visible, stay connected, and stay open to learning. This industry is built on relationships—and the more you nurture them, the more your business will grow.
Contact Info:
- Website: https://bio.site/prettytipsy
- Instagram: https://www.instagram.com/pretty.tipsyco/
- Facebook: https://www.facebook.com/profile.php?id=61550979464324
