Today we’d like to introduce you to Gabby Pinkerton.
Hi Gabby, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I actually stumbled into event planning back in university when I volunteered to help put on a marketing gala. I had no idea what I was doing, but I loved every second of it… the logistics, the creativity, the way an experience comes together piece by piece.
After graduating, I moved to California and really dove in. I interned for both an event planner and a wedding planner while simultaneously working in nonprofit events for the Catalina Island Conservancy. That combination (the fast pace of weddings and the mission-driven world of nonprofits) taught me so much about organization, storytelling, and creating meaningful experiences.
Somewhere in the middle of all that, I realized weddings were the thing that lit me up most, especially outdoor weddings where you can build an experience totally from scratch. That’s what ultimately led me to launch Cause We Can Events and shape it into the full-weekend, adventure-forward planning company it is today.
And now here I am in Tennessee, still creating those immersive, unforgettable celebrations all over the US & internationally. I’ve had the pleasure to plan events in Scotland, Croatia and even South Africa!
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?
Definitely not a perfectly smooth road but I think that’s true for most entrepreneurs. Team building has been one of the biggest challenges. Finding people who not only have the skill set but also align with my values, my client experience, and the way I approach weddings takes time. And once you do find them, learning how to lead, delegate, and trust others with your “baby” is a whole journey on its own.
Relocating was another major hurdle. When my husband and I moved to Tennessee, I basically had to start my marketing from zero. New city, new vendor friends, new couples… everything had to be rebuilt from the ground up. Nashville has such a strong, talented wedding community, so earning that trust and visibility took patience and consistency.
And then there’s my personal lifelong nemesis: shiny object syndrome. I’m the queen of wanting to start a new project every two months. It’s a blessing and a curse but honestly, it’s also how my YouTube channel and co-hosted podcast came to life. I’ve learned to embrace that creative itch while also building systems (and a team!) that keep my core business grounded.
The bumps have been real, but they’ve shaped me into a better planner, leader, and creator. I wouldn’t trade them.
Appreciate you sharing that. What else should we know about what you do?
I’m a wedding planner and educator, and my work really lives at the intersection of logistics, design, and experience. Through my company, Cause We Can Events, my team and I specialize in full-weekend, outdoor weddings (the kind where you’re not just planning a single day, but creating an entire world for people to step into). Tents, private estates, national parks, remote venues… those are my happy places. I love taking a blank canvas and building something immersive, thoughtful, and deeply personal.
What I’m most known for is helping couples create weddings that feel like an adventure: curated, intentional, a little unconventional, and full of great food, music, and connection. My couples tend to be busy professionals and creatives who value experiences and want their guests to feel taken care of from the moment they arrive. That’s where we thrive.
I’m also an educator in the industry. I run a YouTube channel and podcast that help new wedding planners grow their businesses, and that’s become a huge part of my professional purpose. I’m proud of the fact that planners around the country (and honestly, around the world!) use my videos, templates, and resources to launch their careers with confidence. Mentorship is incredibly fulfilling, and it’s been an unexpected but beautiful evolution of my work.
What sets me apart is the combination of my big-picture creative vision and my obsession with detailed logistics. I can dream up an amazing, experiential weekend and also build the spreadsheets, timelines, and systems that make it all actually happen. It’s equal parts art and orchestration, and I love living in that space.
At the end of the day, I’m proud that my career has allowed me to create experiences people remember forever and support the next generation of planners who will shape the industry. It’s the best of both worlds.
Are there any books, apps, podcasts or blogs that help you do your best?
Absolutely! First, I have to give a little wink to Just Another Biz Podcast, which I co-host. We created it because we genuinely wanted a space for honest, unfiltered conversations about wedding entrepreneurship (the wins, the messiness, the experiments, and the realities of building something from scratch.) It can feel really lonely out there sometimes so we’re here to create a community for fellow wedding pros.
My all-time favorite book is Unreasonable Hospitality by Will Guidara. It completely transformed the way I think about service, guest experience, and leadership. I recommend it to literally every wedding vendor I meet.
For mindset and financial growth, I love The Old Money Podcast. It’s calm, practical, grounded advice – the kind that actually makes you want to slow down, think long-term, and make intentional choices.
And honestly, I’m always rotating resources depending on the season. Sometimes I’m deep into business books, other times I’m bingeing travel content or wellness podcasts. But those three are my go-tos that consistently make me better in life and work.
Pricing:
- Weekend Wedding Planning starts at $20,000
- Design & Management starts at $8500
- Wedding Management starts at $3750
Contact Info:
- Website: https://www.causewecanevents.com
- Instagram: https://www.instagram.com/causewecanevents/
- Youtube: https://www.youtube.com/@GabbyPinkerton
- Other: https://podcasts.apple.com/us/podcast/just-another-biz-podcast-unfiltered-business-tips-for/id1487737592
