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
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There’s a shift happening in weddings today — one grounded in clarity, meaning, and a more discerning approach to design, storytelling, and guest experience. In this episode, Reagan sits down with Sarah Schreiber, former Associate Editorial Director of Brides and Martha Stewart Weddings, to explore the evolving expectations of modern couples and the direction our industry is undeniably moving toward.
With over a decade shaping the editorial lens of two of the most influential wedding publications, Sarah brings an invaluable perspective on trend forecasting, the rise of authenticity, the role of social content, and the realities of pricing in a culture that often misunderstands the scale of a celebration. Today, she consults with luxury creatives on brand positioning, website curation, copy, and digital strategy — work informed by thousands of weddings she has reviewed, refined, and uplifted.Together, we explore:

• Why the Pantone Color of the Year sparked industry-wide debate
• How trends actually emerge in today’s landscape
• The rise of deconstructed timelines and guest-first design
• What couples want to see from vendors before they ever inquire
• The declining influence of traditional wedding publications
• The importance of transparency in pricing and value
• How authenticity shapes both online presence and event design
• Sarah’s unexpected career pivot and what reinvention can look like

This conversation is honest, grounded, and deeply relevant for anyone navigating weddings at a high level — whether as a planner, designer, photographer, or a couple seeking a celebration rooted in intention and meaning.
Connect with Sarah:
Instagram: @sar_schreiber
TikTok: @sar_schreiberWant more behind-the-scenes stories, trends, and inspiration?

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• 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.

This week, I sat down with my dear friend and fellow creative, Candice Lorraine Soffner — a woman whose career can only be described as a smorgasbord of creative brilliance. From teaching first grade to designing interiors, producing large-scale events, and now leading her own company, Candice Lorraine LLC, Candice has done it all with an ease and authenticity that’s rare in our industry.
We talked about the real stuff — resilience, burnout, bravery, and the decision to choose yourself even when it feels terrifying. Our conversation moved between laughter and truth-telling — from stories of wrangling groomsmen like first graders to the lessons that come from divorce, reinvention, and rebuilding. What I love most about Candice is her honesty. She reminds us that resilience isn’t a trait you’re born with — it’s something you earn by standing back up.
This episode is for anyone who’s ever wondered if it’s time to start over, or if saying “yes” to something new might just lead you exactly where you’re meant to be.

What You’ll Hear in This Episode:

• How Candice’s path from teaching to event production shaped her approach to leadership
• The importance of treating people with kindness — even when the pressure is high
• Why resilience is the greatest strength in creative industries
• The courage it takes to leave a stable path in pursuit of alignment
• How honesty and integrity always reveal true character
• The freedom that comes from saying yes to the projects that truly excite you
• Why negative space — in life and design — matters

Want more behind-the-scenes stories, trends, and inspiration?

• 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.

Percentage-based pricing can feel intimidating — for planners making the switch from flat fees and for couples trying to understand what it really means for their budget. In this episode, Reagan breaks it down with clarity and candor.
She shares why percentage pricing has always been part of her business model, why it protects both clients and planners, and how it accounts for the unexpected complexities that inevitably arise during the planning process.
From real-world comparisons (think builders, painters, and mechanics) to insights on scope, upgrades, and trust, Reagan tackles the most common fears head-on:

• Does it incentivize planners to overspend?
• Does it penalize couples with sophisticated taste?
• When does a flat fee actually stem from the same math?

This is an essential listen for anyone navigating planner fees — whether you’re a couple questioning what model makes sense for your wedding, or a planner looking to confidently stand by your value.What you’ll hear in this episode:

• Why percentage-based pricing has long been a standard in event planning.
• The three factors that most influence a planner’s percentage.
• How percentage protects against scope creep and unforeseen work.
• Why comparisons to builders, painters, and mechanics matter.
• The myth of being “penalized” for expensive taste.
• How honesty, transparency, and trust shape the client–planner relationship.
  

Want more behind-the-scenes stories, trends, and inspiration?

• 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.

Bronson van Wyck has been called the wizard of hospitality — a visionary whose events have redefined what it means to gather. From his roots on a farm in Arkansas to creating some of the most memorable celebrations across the globe, Bronson’s story is one of imagination, intention, and generosity.
In this episode, we talk about the lessons he learned from his Southern upbringing, his time at the State Department in Paris, and the unforgettable moments he’s orchestrated for guests worldwide. Bronson shares why true welcome is about warmth, not wealth, the importance of surprise and pacing at any event, and why hospitality is ultimately about making people feel safe, seen, and delighted.
If you’ve ever wondered how the world’s best hosts create magic — or how small, thoughtful details can change the entire atmosphere of a party — this conversation is for you.
What you’ll hear in this episode:

• How Bronson’s childhood shaped his understanding of hospitality
• The surprising lessons he learned working under Ambassador Pamela Harriman
• Why pacing and surprise are essential to unforgettable parties
• The principle of “warmth over wealth” and what it means for hosts and guests alike
• How he uses his talent to give back through meaningful charitable work

Connect with Bronson van Wyck

• Website: Van Wyck & Van Wyck and Workshop Worldwide
• Instagram: @bronsonvanwyck 
• LinkedIn: Bronson van Wyck 

Want more behind-the-scenes stories, trends, and inspiration?

• 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.

When couples envision their wedding, they picture the flowers, the music, the guests dancing into the night—not contracts, liability clauses, or bankrupt vendors. Yet, as budgets rise and weddings rival the cost of a new home, protecting that investment becomes non-negotiable.
In this episode of The Wine and Dine Me Podcast, I sit down with John Foreman of KSA Insurance to break down what wedding and event insurance really covers, who it protects, and why it matters more than ever.
We cover:

• The difference between liability coverage and financial loss protection
• Why “meeting venue requirements” doesn’t mean you’re personally covered
• Common limitations of online policies—and when to call a trusted advisor instead
• Real stories where event insurance saved couples hundreds of thousands of dollars
• What planners need to know about professional liability and working with contractors
• The growing importance of cyber insurance in today’s world

If you’ve ever wondered whether insurance is worth it—or what kind of coverage you should actually be looking for—this conversation is the clarity you’ve been waiting for.
Want more behind-the-scenes stories, trends, and inspiration?

• 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 solo episode, I’m sharing the things I'm often tempted to bite my tongue on as a wedding planner. Consider this my unfiltered list of truths I’d tell you if I wasn’t worried about hurting your feelings.

I talk about why cocktail hours don’t need to feel like carnivals, why florists can’t (and shouldn’t) give quotes prior to contracting, and why lighting is one of the most overlooked investments that can transform your entire celebration. I also share my take on welcome gifts that miss the mark, the pressure couples feel to over-entertain their guests, and why you should trust your planner to do the job you hired them for.

These are insights pulled straight from years of producing high-touch events for discerning clients. They’re not always comfortable to hear, but they will shift the way you think about planning a wedding.
Topics I Cover:

• Why less is often more when entertaining guests
• The truth about florist quotes (and red flags to avoid)
• Lighting as the unsung hero of ambiance
• When welcome gifts fall flat (and what makes them memorable)
• Why too much signage cheapens the atmosphere
• The importance of letting your planner actually do their job
• A reality check on negotiating with vendors in high-demand markets

If you would like to talk with us about planning your next event, CLICK HERE.
Want more behind-the-scenes stories, trends, and inspiration?

• 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 Podcast⁠ and ⁠Spotify⁠, where we explore all things weddings, life, and business.

Love is emotional. Marriage is legal. Attorney Ryan Schwartz joins Reagan to discuss the questions every couple should ask before “I do.”

Most couples spend months planning the perfect wedding—but skip the conversations that could protect their future. In this candid episode, attorney Ryan Schwartz joins host Reagan to talk about the legal side of marriage, from prenups to “change of heart” clauses and why choosing who you have children with may be the most important decision of your life.

Ryan shares stories from his work in family and criminal law, explains why a prenup is really an operating agreement for your marriage, and breaks down the costly mistakes couples make when love and finances collide. Reagan adds her own perspective from years of seeing the “front end” of marriage planning—and why she believes these talks can be just as important as the seating chart.

Whether you’re engaged, remarried, or simply curious, this conversation offers a rare, practical look at the realities behind the romance.
Topics We Cover:

• Why marriage is both an emotional and legal contract
• The single most important decision you’ll ever make (and it’s not your venue)
• What a prenup really is—and isn’t
• The financial and emotional costs of divorce
• How to talk about money, assets, and values before saying “I do”
• Common legal mistakes couples make without realizing it

Guest Info:
Instagram: @myschwartzisbiggerthanyours
Website: lowcountrylawyerssc.com
Facebook: Schwartz Law Firm, LLC 

Want more behind-the-scenes stories, trends, and inspiration?

• 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, Reagan sits down with Persephone—founder of The Media Socialites and a straight-shooter when it comes to marketing in the luxury space—for a conversation that peels back the polished curtain on what really drives results. From the myth of the industry "the best of lists" to the fine line between PR and performance, they unpack what’s actually worth your time and money—and what’s just noise.
Persephone shares how she scaled her agency from solo founder to a 50-person team, why she built her business during maternity leave, and how she’s helping brands rethink ROI in a world that’s obsessed with optics. Together, they explore the deeper questions: Are you marketing to clients or colleagues? What does true discretion look like online? And how do you lead with authenticity without diluting your brand?
Whether you’re a planner, creative, or founder in the luxury space, this episode challenges you to stop copying the playbook and start defining success on your own terms.
Topics We Cover:

• Marketing vs. PR (and why the difference matters more than ever)
• Vanity metrics and the illusion of being “seen”
• How to set boundaries without making it a headline
• Transparency as the new luxury
• What real clients are actually paying attention to

Guest Info:

• Follow Persephone in Instagram at @persephonesays and @themediasocialites
• Learn more about The Media Socialites at  themediasocialites.com.
  

Want more behind-the-scenes stories, trends, and inspiration?

• ⁠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 honest and insightful conversation, Reagan sits down with longtime friend and fellow planner Tara Skinner to explore the nuanced realities of building—and sustaining—a planning business with integrity. Together, they unpack what experience really looks like in an industry that often rewards surface-level polish over operational depth.
They talk candidly about vendor loyalty, pricing structures, client education, and the tricky terrain of team building as your business scales. From flat fees to percentage-based models, from early missteps to multi-million-dollar productions, Tara shares the moments that shaped her sixteen-year career—and the lessons that continue to guide her growth.
At its core, this episode is about navigating evolution with grace: growing your team, maintaining standards, and preserving relationships, even when hard conversations are required. For planners, creatives, and clients alike, it’s a compelling look behind the curtain.
Want more behind-the-scenes stories, trends, and inspiration?

• 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 in Apple Podcast and Spotify, where we explore all things weddings, life, and business.