In this episode of The Wine and Dine Me Podcast, Reagan sits down with Lynn Easton, founder of Easton Events, for a candid conversation about what actually separates “pretty” from powerful in high-stakes event work.

Lynn shares how she built a brand people recognize before they even read the caption, why language is one of a planner’s most underrated tools, and the real reason budgets must get handled early (not “once we see what things cost”). They also get into the systems behind calm execution, including the story that led Lynn to build her timeline and budget infrastructure and eventually turn it into eventPERCH.

In this episode, we cover:

• Why “ma’am” and “sir” can shrink your authority when you’re the one responsible for the call
• Branding as behavior, not visuals: what makes a brand feel consistent in the room and in the inbox
• The budgeting conversation planners avoid, and why avoiding it makes you the villain later
• What Instagram is actually good for (and what it should never replace)
• The moment a single timeline mistake changed how Lynn built her systems forever
• Why Lynn chose to share her proprietary workflow with the industry through eventPERCH
• A real take on growth: more people, better structure, and protecting the work from burnout

About Lynn Easton:
Lynn is the founder of Easton Events and Easton Education, known for producing sophisticated, high-touch celebrations with serious operational discipline behind the scenes.
Connect with Lynn:

• Easton Events on Instagram: @eastonevents
• Easton Education on Instagram: @eastoneducation
• eventPERCH: eventPERCH (event planning software built from Easton’s internal systems)

Listen & Follow

• Subscribe to our newsletter for inspiration, updates, and expert advice.
• Follow us on Instagram and TikTok for behind-the-scenes moments, trending ideas, and so much more.
• Tune in to our Wine and Dine Me Podcast on Apple Podcasts and Spotify, where we explore all things weddings, life, and business.

In this episode of The Wine and Dine Me Podcast, Reagan sits down with Calder Clark for a candid conversation about what it really takes to produce beautiful events without losing the plot. This one is equal parts creative process and hard-earned perspective. The kind you only get after years of doing the work, living through the curveballs, and learning when to hold the line.
Calder shares how she thinks about value, how she navigates client expectations (especially when the vision is larger than the budget), and why the best planners are the ones who can protect the experience while staying calm and direct. They also dig into what fuels Calder’s design process, how she stays inspired without living on social media, and why getting copied is not the crisis people make it out to be.
It’s smart, grounded, and full of the kind of real-world advice that helps you refine how you sell, design, communicate, and lead.In this episode, we cover:

• Why “value” is the real conversation, not price
• How to handle the expectation gap when budgets don’t match the vision
• Why you need the bill payer involved early (and how it changes everything)
• The difference between planning, designing, and producing - and why clients confuse it
• Boundaries that still feel high-touch and responsive
• How Calder stays inspired without chasing the scroll
• What her actual design process looks like (sources, references, and how she builds a point of view)
• Why being copied is not the threat people think it is
• When “pretty” becomes standard, and how to keep your work intentional
• The mindset shift that makes you easier to work with - and better at the job

Guest Spotlight
Calder Clark is a Charleston-based planner and designer known for her editorial eye, confident point of view, and ability to balance beauty with real-world execution. She brings a rare combination of creative clarity and business candor - the kind that elevates the final product and protects the client experience at every step.
Listen & Follow

• Subscribe to our newsletter for inspiration, updates, and expert advice.
• Follow us on Instagram and TikTok for behind-the-scenes moments, trending ideas, and so much more.
• Tune in to our Wine and Dine Me Podcast on Apple Podcasts and Spotify, where we explore all things weddings, life, and business.

In this episode of The Wine and Dine Me Podcast, Reagan sits down with Jessica Connolly, co-founder and creative director of Social Supply Design, for a wide-ranging conversation on what it actually takes to build meaningful experiences at scale.

Jessica shares her unconventional path from government work to wedding planning to running a multimillion-dollar experiential design and build studio. Together, Reagan and Jessica unpack why design without function is just decoration, how emotion and execution must work together, and what happens when creatives stop designing for Instagram and start designing for people.

This conversation goes deep into the realities of entrepreneurship, scaling a labor-intensive business, hiring with intention, and navigating creativity, leadership, and ADHD in a high-pressure industry. It’s honest, grounded, and filled with insight for anyone building something that matters.

In this episode, we cover:

• Why design without function fails the guest experience
• The difference between decoration and design that performs
• Taking real risks and going all in on your business
• How divorce, alignment, and life shifts can clarify your work
• Scaling a creative business when every project is a one-off
• Bringing production in-house to protect quality and execution
• Designing spaces around human behavior and emotional flow
• Hiring for humility, hunger, and honesty
• Why trends fade but nostalgia and intention endure
• What’s overdone in event design and what’s being overlooked

Guest Spotlight
Jessica Connolly is the co-founder and creative director of Social Supply Design, an experiential design and production studio known for immersive, interior-grade builds for events, brands, and venues nationwide. Her work sits at the intersection of architecture, emotional storytelling, and execution at scale.Connect with Jessica
Instagram: @socialsupplydesign
Website: socialsupplydesign.com
Listen & Follow

• Subscribe to our newsletter for inspiration, updates, and expert advice.
• Follow us on Instagram and TikTok for behind-the-scenes moments, trending ideas, and so much more.
• Tune in to our Wine and Dine Me Podcast on Apple Podcasts and Spotify, where we explore all things weddings, life, and business.