Wine and Dine Me
The Wine and Dine Me podcast is brought to you by Reagan Prechter, owner of Reagan Events, a luxury event planning and design firm based in Charleston, South Carolina. With more than 15 years of experience executing even...
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Est. listeners per new episode within ~30 days
900 to 8.1K🎙 Monthly cadence·72 episodes·Last published 1mo ago - Monthly Reach
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1K to 9K🇺🇸100% - Active Followers
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400 to 3.6K
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| Date | Episode | Description | Length | ||||||
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| 9/22/26 | The Psychology of the Velvet Rope: Attracting Fewer, Bigger, Better Clients with Rachael Johanson | What changes when you stop trying to book more clients and start building a business designed to attract the right ones?In this episode of The Wine and Dine Me Podcast, Reagan sits down with strategist Rachael Johanson to talk about moving from what Rachael calls the “penny market” into the “silver dollar market” - fewer clients, larger projects, stronger positioning, and far more intention behind how a founder is seen.Rachael works exclusively with female entrepreneurs who want to move into the top of their market. Together, she and Reagan unpack why the marketing tactics that helped build your business may not be the ones that take it to the next level, and why positioning has to come before almost everything else.They get into the psychology of the “velvet rope,” the value of niching down, using press as a pricing tool, building strategic referral relationships, and why relationships still outperform most marketing tactics.The conversation also gets personal. Reagan and Rachael talk about women underpricing themselves, why founders should still be taking their own connection calls, how headshots and team positioning can quietly undermine authority, and why building a bigger business does not necessarily have to mean giving more of your life away.Topics We CoverThe difference between the “penny market” and “silver dollar market”Why strategies that worked while building your business may stop working at the next levelHow to identify a niche using your existing clients and past workThe psychology behind Rachael’s “velvet rope” positioningWhy fewer inquiries can actually signal stronger positioningPositioning, press, paid speaking, and strategic partnershipsWhy Rachael views press as a pricing tool rather than a vanity metricWhy relationships can produce a stronger return than traditional marketingSelling to clients for whom budget is not the primary concernWhy founders should personally take high-level client callsTurning a “sales call” into a connection callWhy women often struggle to price their expertise confidentlyHow personal style, headshots, and website hierarchy influence positioningWhy your existing portfolio may contain work you are overlookingBuilding a selective business while still protecting family lifeGuest InfoRachael Johanson is a strategist who works exclusively with women building sophisticated service businesses and personal brands. Her work focuses on positioning, sales psychology, visibility, partnerships, and helping founders become more selective about the clients and opportunities they pursue.Rather than simply generating more inquiries, Rachael helps women create businesses where the right clients arrive already understanding why they are the person for the job.Connect with Rachael:Website: Rachael JohansonInstagram: @rachaeljohanson_Listen & FollowFor more candid conversations about hospitality, sophisticated events, leadership, business, and the standards behind unforgettable experiences, follow The Wine and Dine Me Podcast.Subscribe to our newsletter for inspiration, updates, and expert perspective.Follow Reagan Events on Instagram and TikTok for behind-the-scenes moments, event insight, and conversations from the podcast.Listen to The Wine and Dine Me Podcast on Apple Podcasts, Spotify, and Youtube.Hosted by Reagan Prechter, founder and creative director of Reagan Events. | 52m 37s | ||||||
| 9/14/26 | Scaling Without Sacrificing the Standard with Jordan Kahn | What happens when a creative business grows from one performer to 25 weddings every weekend without losing control of the experience?Jordan Kahn, founder of Jordan Kahn Music Company, joins Reagan for a candid conversation about scaling, standards, hospitality, and the systems required to deliver consistently at a national level.Jordan started working in events at just 12 years old, DJing parties to raise money for the Make-A-Wish Foundation. What began as an early love of music and full dance floors eventually grew into a company with teams across the country, multiple entertainment brands, and an infrastructure designed to remove as many variables as possible from the wedding day.But Jordan is clear: talent alone is not enough.He and Reagan talk about why professionalism is non-negotiable, how clear expectations make delegation possible, why he believes in hiring slowly and acting quickly when someone no longer fits the standard, and how his team approaches everything from volume control and equipment to travel logistics and communication with planners.They also get into the business behind the business. Jordan explains how studying the inquiries his company was turning away revealed an entirely new market, why accessibility does not have to mean compromising quality, and how carefully structured pricing helped the company scale while protecting the value of its bands.Then the conversation becomes personal.After spending most of his life performing at other people’s weddings, Jordan recently experienced one from the other side as the groom. He shares how that changed his perspective, why the emotional weight of the day surprised him, and how the experience strengthened his mission to give other couples the same feeling he experienced at his own wedding.It is a conversation about music, yes. But even more, it is about leadership, relationships, standards, and remembering who the work is ultimately for.Topics We CoverStarting in the events industry at 12 years oldScaling without sacrificing qualityCreating standards before expanding a teamWhy talent without professionalism is not enoughReading the room through music, tempo, and volumeBuilding operational systems that make planners’ jobs easierDelegating without micromanagingHiring slowly and setting clear expectationsFinding growth opportunities inside your own CRMServing different price points without compromising the productGenuine relationships vs. transactional networkingWhat becoming a groom taught Jordan about weddingsWhy the couple always has to remain at the centerGuest Info:Jordan Kahn is the founder of Jordan Kahn Music Company, a national private entertainment company providing live music for weddings and events across the United States.Jordan began working in the event industry at 12 years old and went on to study at Berklee College of Music before building his career as both a performer and entrepreneur. Today, his company operates teams across major markets throughout the country and performs approximately 25 weddings on an average weekend.His approach combines performance with detailed operational systems, from music programming and sound control to travel logistics, equipment standards, team training, and planner communication.At the center of it all is one principle: the people working the event are there for the couple and their guests.For more honest conversations about hospitality, sophisticated events, leadership, business, and the standards behind unforgettable experiences, follow The Wine and Dine Me Podcast on Spotify, Apple Podcasts, and YouTube.Hosted by Reagan Prechter, founder and creative director of Reagan Events.Listen to The Wine and Dine Me Podcast | 43m 49s | ||||||
| 8/14/26 | Why Relationships Still Matter More Than Recognition with Alison Hotchkiss | After nearly 25 years in the events industry, Alison Hotchkiss has learned that longevity has far less to do with recognition than it does with relationships, resilience, and the willingness to evolve.Reagan and Alison get candid about building businesses before Instagram, leading teams through inevitable change, collaborating without ego, and knowing when to stop doing everything yourself. They also discuss why beautiful work is no longer enough - the clearest point of difference is how well clients, guests, vendors, and employees feel cared for.In This EpisodeReagan and Alison discuss:Building a destination event company before Instagram and online vendor directoriesWhy access to endless inspiration may be weakening originalityThe truth behind industry lists, visibility, and overnight successMaintaining relationships with clients beyond a single eventBuilding a company that is larger than its founderAccepting that talented employees will eventually leaveHiring the right mix of employees, freelancers, and creative partnersCollaborating with designers and production companies without egoInvesting thoughtfully in mentorship, education, and industry relationshipsWhy guest experience remains the strongest point of differentiationAbout Alison HotchkissAlison Hotchkiss is the founder of Alison Events, a destination event planning and production company with nearly 25 years of experience creating celebrations around the world. She is also the author of three books and a mentor to emerging event professionals.Listen & FollowSubscribe 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. | 53m 37s | ||||||
| 6/4/26 | The Missing Layer in High-Touch Events: Concierge Event Medicine with EventDox | In this episode of The Wine and Dine Me Podcast, Reagan sits down with Caroline Brown and Julie Livingston, co-founders of EventDox, a concierge event medicine service designed for elevated weddings, private events, and high-touch celebrations where discretion and preparedness matter.Julie, a seasoned wedding photographer, first noticed the gap after years of seeing guests, family members, brides, and grooms become sick or injured during events, sometimes leading to ambulances, missed moments, or family members stepping away to manage the situation. That experience sparked the question: why isn’t there a better way to handle medical needs without disrupting the event?Caroline brings a background in healthcare, concierge medicine, and relationship-driven business, helping shape EventDox into what they describe as a hospitality company that does medicine, not the other way around. Their providers dress in event attire, blend into the environment, and understand the expectations of sophisticated private events.The conversation explores the difference between traditional EMT coverage and concierge event medicine, including why nurse practitioners, physician assistants, and physicians can offer a broader scope of care on site. Caroline and Julie explain what they bring to an event, from prescription medications and IVs to AEDs, EpiPens, Narcan, and wellness lounge support.They also discuss the liability planners and hosts may not realize they are carrying, from handing out Advil to hiring a nurse friend or relying on a doctor who happens to be attending as a guest. EventDox operates as a medical practice with licensed providers, clinical oversight, and malpractice insurance, filling the space between a small injury and a full emergency response.The episode also moves into a more personal conversation about reinvention, resilience, motherhood, postpartum anxiety, difficult life chapters, and what it means to build something meaningful while still being human. Caroline and Julie share how their own hard seasons shaped the way they show up as business owners and as women leading a new company.In this episode, we talk about:What concierge event medicine actually meansWhy medical support is becoming a thoughtful layer of event hospitalityThe difference between EventDox and traditional EMT coverageHow medical care can be integrated discreetly into weddings and private eventsThe liability planners, venues, and hosts may not realize they are carryingWhy relying on a guest who happens to be a doctor is not the same as having medical coverageWellness lounges, IV support, and on-site medical care for guests and event teamsBuilding a business from lived experience and industry needMotherhood, resilience, postpartum anxiety, and asking for helpWhy preparedness should feel like care, not fearGuest InformationGuests: Caroline Brown and Julie LivingstonCompany: EventDoxEmail: [email protected]: @eventdoxListen & FollowSubscribe 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. | 34m 33s | ||||||
| 5/28/26 | Bryan Rafanelli on Building Clients for Life | In this episode of The Wine and Dine Me Podcast, Reagan sits down with Bryan Rafanelli for a conversation about the kind of event work that lasts beyond a single night.Bryan shares how he thinks about client relationships, not as one-time projects, but as long-term partnerships built through trust, care, and future-minded service. From wedding planning and private celebrations to corporate and nonprofit events, he talks about why the strongest businesses are built by staying close to clients, understanding who is in the room, and creating moments that feel personal without being performative.Reagan and Bryan also talk about high-touch guest service, the pressure to stay relevant, why event innovation cannot only be visual, and how planners can advocate for the right decisions when the integrity of the guest experience is at stake. The conversation moves from business strategy to hospitality philosophy, with Bryan offering a generous, candid look at what has shaped his career after decades in the event industry.They also discuss: Why a wedding can be the beginning of a lifelong client relationship How to make sure guests know who produced the event without awkward self-promotion The role of trust when discussing budgets, investments, and last-minute decisions Why planners should understand the character of the guest list How to approach VIPs with confidence and humanity Why diversifying your client portfolio can create a stronger business The difference between staying visible and staying truly relevant Why guest experience is still the real measure of a memorable eventConnect with Anja Winikka:Instagram: @rafanellieventsWebsite: rafanellievents.comListen & FollowSubscribe 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. | 42m 04s | ||||||
| 5/21/26 | Visibility Is Not Influence: Anja Winikka on Trust, Taste, and the Rooms That Matter | In this episode of The Wine and Dine Me Podcast, Reagan sits down with Anja Winikka, founder and CEO of Freeda, a private membership network for leaders in the global events industry.Anja has seen the wedding and event industry from nearly every angle. She spent more than a decade at The Knot, helped shape modern wedding media, co-founded Maroo, and now leads Freeda, where creative founders gather in curated peer groups for honest conversations, trusted relationships, and the kind of support that rarely happens in public.This conversation looks at the difference between visibility and true influence, why follower count is no longer the strongest signal of credibility, and why discerning clients are paying closer attention to trust, referrals, and the rooms people are actually in.Reagan and Anja also talk about the loneliness that can come with building a successful creative business, the pressure to appear booked and thriving, and what longevity really requires behind the scenes: emotional intelligence, operational maturity, financial clarity, boundaries, and relationships that can sustain you through different seasons of business and life.This episode is for creative founders, planners, designers, photographers, and hospitality professionals who are asking bigger questions about growth, visibility, trust, and what kind of business they actually want to build.Listen to the full episode for a candid conversation on influence, private networks, mature business ownership, and why the right room can change everything.In This EpisodeReagan and Anja discuss: The shift from media-driven visibility to trust-based influence Why follower count does not equal credibility How high-end clients evaluate trust differently now What creative founders are craving behind the scenes Why Freeda was created for more honest peer conversations The difference between networking and belonging What longevity really looks like in the wedding and event industry Why emotional intelligence and operational maturity matter more than ever How the right relationships can shape both your business and your lifeConnect with Anja Winikka:Instagram: @joinfreedaWebsite: https://www.joinfreeda.com/Listen & FollowSubscribe 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. | 32m 35s | ||||||
| 5/14/26 | From Influence to Trust: How Creative Entrepreneurs Build Brands That Last with Lauren Taylor | What matters more now: being followed, or being found?In this episode of The Wine and Dine Me Podcast, Reagan sits down with Lauren Taylor, founder of LeFleur Society, a high-touch agency representing creators, celebrities, public figures, and entrepreneurs. Lauren’s path started in law, but her work now sits at the intersection of legal protection, brand strategy, creator representation, and business growth.Together, Reagan and Lauren talk about what it really takes to build a brand that lasts. Not just one that looks good online, but one built with clarity, protection, credibility, and trust.They dig into why follower count is losing its power, why authenticity has become harder to fake, and why creative entrepreneurs need to think more like business owners. Lauren also shares what brands are looking for now, how searchability and SEO are changing the way people discover businesses, and why the strongest founders are not waiting for the perfect moment to begin.In This EpisodeReagan and Lauren discuss: Why follower count is becoming less important than credibility How creative entrepreneurs can better understand their own value What authenticity actually means now How sophisticated brands can show more realness without losing polish Why personal brand and business brand need to grow together The difference between viral content and lasting brand trust Why SEO, searchability, and platform strategy matter more than ever What creators may be giving away without realizing it Why entrepreneurs are beginning to replace traditional influencers How to build a brand ecosystem that extends beyond one platform Why imperfect timing is often the moment to moveConnect with Lauren Taylor:Instagram: @lefleursociety / @laurentaylorattorneyWebsite: https://www.lefleursociety.com/Listen & FollowSubscribe 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. | 41m 42s | ||||||
| 3/6/26 | Obsessive Hospitality and Zero-Management Photography with Alex Schon | In this episode of The Wine and Dine Me Podcast, Reagan sits down with photographer and licensed sommelier Alex Schon to talk about what “exceptional” really looks like when the weekend is high-stakes and the margin for error is basically nonexistent. They get into the difference between a vendor who creates pretty work and a partner who protects the entire experience. The throughline is simple: the best people on your team add calm, not questions.Alex shares how an aerospace engineering background wired him to think in systems, contingencies, and cause-and-effect. One small delay doesn’t stay small. It cascades. That’s why his standard is “zero management.” He shows up already briefed, already prepared, already watching the room, already solving what most people don’t notice until it’s too late.They also talk about the “one-inch rule” and why tiny details matter more than anyone wants to admit. Because photography is the permanent record. It becomes the proof of the weekend. One crooked chair or messy corner in a frame can quietly undermine the credibility of a multi-layered production. Not because clients are picky, but because the images are forever.Along the way, Reagan and Alex get candid about trust, pricing, and the post-COVID market. Alex makes a point every vendor needs to hear: pricing isn’t just math. It’s integrity. If you feel opportunistic or inconsistent, the people who refer you will notice first.In this episode, we cover: What “zero management” actually means on a wedding weekend Why obsessive hospitality is the real flex, not performative service How an engineering brain changes the way you plan and shoot The one-inch rule and how small details can weaken the entire story Why photography is the final filter, not the main character How to build calm through preparation, not personality Pricing, trust, and why the market always corrects inflated value The difference between anxiety and care, and why clients feel it Alex’s sommelier lens on guiding experiences without showing off His closing line that says everything: if you’re a project, you’re not a partnerKey moments (timestamps) 00:00 Intro and why this conversation matters for planners and vendor teams 03:40 Alex’s background and how engineering shaped his planning brain 08:55 What “zero management” looks like in real time 13:20 Obsessive hospitality and the Mary Poppins bag mentality 18:45 The cascade effect: how one delay becomes the whole day 24:10 The one-inch rule and why details affect credibility in photos 31:30 Photography as the permanent record: proof, not performance 38:05 Pricing, integrity, and what breaks trust fastest 46:15 Sommelier mindset and guiding people through experience 52:30 Closing takeaway: partnership over performanceConnect with Alex: Instagram: @alexschonWebsite: www.alexschon.comListen & FollowSubscribe 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. | 1h 11m 30s | ||||||
| 2/20/26 | Discretion, Directness, and High-Stakes Events with Laura Somma | In this episode of The Wine and Dine Me Podcast, Reagan sits down with her Italy-based partner, Laura Somma, to talk about what “high-touch” really looks like when the guest list includes celebrities, royals, and families who do not tolerate chaos. They start with the practical magic of a cross-time-zone partnership, then trace Laura’s path from studying German literature to building a career defined by precision, discretion, and calm execution. Laura shares the behind-the-scenes stories that shaped her standards, including producing a paparazzi-proof private island birthday for Naomi Campbell in Positano and how a chance conversation in Doha led to working inside the orbit of the royal family of Qatar. Along the way, she makes a point planners need to hear: the most powerful thing you can bring into a room full of “yes people” is a steady voice that tells the truth. They also dig into what sophisticated clients actually crave when they can already access everything: authenticity, simplicity, and experiences rooted in place. Laura explains why she builds a “bridge” in design across cultures, why a local performance is often the most unforgettable anchor of a destination celebration, and how The Wedding Prive was created to solve the real complexity of multi-destination weddings with senior planners leading each chapter. In this episode, we cover:Why a US + Italy planning partnership eliminates lag, follow-ups, and lost daysHow German literature (and German work habits) shaped Laura’s planning brainThe first wedding she ever produced, and why she asked two questions firstWhat discretion looks like when paparazzi are actively trying to get inThe real reason top-tier clients choose “simple” food and simple momentsHow to read a culture fast (and why you should stop relying on other people’s opinions)Laura’s non-negotiable for guest experience: a performance that belongs to the placeWhat The Wedding Prive is, and why multi-destination weddings are the next frontierLaura’s closing advice to planners: trust your gut and lead the conversation Key moments (timestamps)00:52 Laura’s background and why Reagan trusts her as an Italy partner04:24 German literature, Goethe, and the pivot into events10:35 Her first wedding came from a corporate guest, and she never “sold” planning14:55 The private island birthday story and what discretion actually requires20:07 The Doha connection that opened the door to royal work29:36 How Laura learns a new culture: sit, watch, listen, decide for yourself33:58 Her guest-experience non-negotiable: local performance over predictable extras36:24 The Wedding Prive and the operational reality of multi-destination weddings48:52 Final advice: trust your gut, stop people-pleasing, lead the roomConnect with Laura:Instagram: @theweddingprive, @ellesseventsEmail: [email protected]: The Wedding PriveListen & FollowSubscribe 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. | 52m 37s | ||||||
| 2/3/26 | Own Your Power: Authority, Calm, and the Systems That Let You Lead at the Highest Level with Lynn Easton | 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 callBranding as behavior, not visuals: what makes a brand feel consistent in the room and in the inboxThe budgeting conversation planners avoid, and why avoiding it makes you the villain laterWhat Instagram is actually good for (and what it should never replace)The moment a single timeline mistake changed how Lynn built her systems foreverWhy 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 burnoutAbout 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 & FollowSubscribe 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. | 1h 06m 27s | ||||||
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| 1/23/26 | Clear Is Kind: Budgets, Boundaries, and Better Planning with Calder Clark | 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 priceHow to handle the expectation gap when budgets don’t match the visionWhy you need the bill payer involved early (and how it changes everything)The difference between planning, designing, and producing - and why clients confuse itBoundaries that still feel high-touch and responsiveHow Calder stays inspired without chasing the scrollWhat 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 isWhen “pretty” becomes standard, and how to keep your work intentionalThe mindset shift that makes you easier to work with - and better at the jobGuest SpotlightCalder 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 & FollowSubscribe 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. | 1h 03m 53s | ||||||
| 12/29/25 | All In or Nothing: The Reality of Scaling a Creative Business with Jessica Connolly of Social Supply Design | 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 experienceThe difference between decoration and design that performsTaking real risks and going all in on your businessHow divorce, alignment, and life shifts can clarify your workScaling a creative business when every project is a one-offBringing production in-house to protect quality and executionDesigning spaces around human behavior and emotional flowHiring for humility, hunger, and honestyWhy trends fade but nostalgia and intention endureWhat’s overdone in event design and what’s being overlookedGuest SpotlightJessica 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 JessicaInstagram: @socialsupplydesignWebsite: socialsupplydesign.comListen & FollowSubscribe 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. | 1h 01m 07s | ||||||
| 12/12/25 | The Future of Weddings: Trends, Truth, and Transparency with Sarah Schreiber | 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 debateHow trends actually emerge in today’s landscapeThe rise of deconstructed timelines and guest-first designWhat couples want to see from vendors before they ever inquireThe declining influence of traditional wedding publicationsThe importance of transparency in pricing and valueHow authenticity shapes both online presence and event designSarah’s unexpected career pivot and what reinvention can look likeThis 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_schreiberTikTok: @sar_schreiberWant 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. | 47m 02s | ||||||
| 10/9/25 | When Grace Meets Grit: A Conversation on Resilience and Renewal | 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 leadershipThe importance of treating people with kindness — even when the pressure is highWhy resilience is the greatest strength in creative industriesThe courage it takes to leave a stable path in pursuit of alignmentHow honesty and integrity always reveal true characterThe freedom that comes from saying yes to the projects that truly excite youWhy negative space — in life and design — mattersWant 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. | 49m 13s | ||||||
| 10/3/25 | Demystifying Percentage Pricing: A Planner’s Perspective | 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. | 16m 17s | ||||||
| 9/26/25 | Warmth Over Wealth: Bronson van Wyck on the True Meaning of Hospitality | 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 hospitalityThe surprising lessons he learned working under Ambassador Pamela HarrimanWhy pacing and surprise are essential to unforgettable partiesThe principle of “warmth over wealth” and what it means for hosts and guests alikeHow he uses his talent to give back through meaningful charitable workConnect with Bronson van WyckWebsite: Van Wyck & Van Wyck and Workshop WorldwideInstagram: @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. | 28m 12s | ||||||
| 9/17/25 | Event Insurance Details Every Couple (and Planner) Should Know | 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 protectionWhy “meeting venue requirements” doesn’t mean you’re personally coveredCommon limitations of online policies—and when to call a trusted advisor insteadReal stories where event insurance saved couples hundreds of thousands of dollarsWhat planners need to know about professional liability and working with contractorsThe growing importance of cyber insurance in today’s worldIf 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. | 25m 08s | ||||||
| 8/27/25 | Hot Takes from a Planner: What I’d Tell You If Feelings Weren’t a Factor | 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 guestsThe truth about florist quotes (and red flags to avoid)Lighting as the unsung hero of ambianceWhen welcome gifts fall flat (and what makes them memorable)Why too much signage cheapens the atmosphereThe importance of letting your planner actually do their jobA reality check on negotiating with vendors in high-demand marketsIf 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. | 14m 25s | ||||||
| 8/15/25 | Love, Law, and Hard Truths: What Couples Need to Know Before Marriage | 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 contractThe single most important decision you’ll ever make (and it’s not your venue)What a prenup really is—and isn’tThe financial and emotional costs of divorceHow to talk about money, assets, and values before saying “I do”Common legal mistakes couples make without realizing itGuest Info:Instagram: @myschwartzisbiggerthanyoursWebsite: lowcountrylawyerssc.comFacebook: 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. | 30m 16s | ||||||
| 8/8/25 | Data-Driven Marketing, Social Media Icks, and the Myth of the “The Lists” with Persephone | 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 headlineTransparency as the new luxuryWhat real clients are actually paying attention toGuest Info:Follow Persephone in Instagram at @persephonesays and @themediasocialitesLearn 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. | 42m 22s | ||||||
| 7/31/25 | Graceful Growth & Hard Conversations: Inside the Planning 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. | 49m 48s | ||||||
| 5/7/25 | Wedding Panner Wellness Check: Weathering the Storm When it Rains | In this solo episode, Reagan hits record from her car during a stressful, rain-filled wedding week in Charleston. As the rainy weekend looms, Reagan offers a powerful reflection on what it really means to lead under pressure—especially when the weather doesn't cooperate.Reagan speaks directly to fellow planners and vendors staring down a weekend of rain plans, vendor pivots, and client disappointment. She shares real stories from past events where Plan D became the best plan of all and reminds us that the true value of a planner often reveals itself when things go wrong.With grace and clarity, she covers:How to lead your team and clients with calm confidenceWhy client communication during weather disruptions should focus on ownership, not controlThe emotional nuance of delivering hard news with compassion (and boundaries)How your vendor relationships become the lifeline in high-stakes scenariosWhat couples should know when their planner insists on a preferred vendorFor anyone in the thick of planning—especially during stormy seasons—this is a reminder of your impact, your preparedness, and your ability to turn chaos into celebration.Mentioned in this episode:How to structure rain plans with clear optionsThe importance of vendor trust and collaborationPast event stories where the backup plan stole the showWant 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. | 9m 11s | ||||||
| 4/25/25 | No More Loose Ends: Legal Essentials for Event Planners & Creative Business Owners with Magi Fisher | On this episode of The Wine and Dine Me Podcast, I’m joined by someone whose dual talents are as rare as they are vital: Magi Fisher. Equal parts luxury wedding photographer and licensed attorney, Magi has carved out a niche as the go-to resource for creatives who want to safeguard their business while building a brand worth celebrating.We explore the often-overlooked legal layers of running a creative business—topics like contracts that actually protect you, what most vendors miss about NDAs, how to responsibly grow your team, and why “clear is kind” isn’t just a leadership mantra but a legal one too.Whether you’re a seasoned planner or just starting out, Magi delivers clear, candid insight on the safeguards that turn small businesses into thriving empires. She breaks down everything from trademarking your business name to managing intellectual property with grace—and shows us why a well-written contract is the best investment you’ll ever make.What You’ll Learn:Why creatives often avoid legal protection—and the real cost of waiting too longHow to approach NDAs without fear (and even how to negotiate them)The legal traps that derail growing teams—and how to avoid themHow to set expectations with clients and contractors through clean communicationThe top protections every event professional should have in place right nowThis episode is a must-listen for anyone who wants to build a business that’s as protected as it is profitable.🔗 Links Mentioned Explore Magi's contract templates: The Artist LawyerConnect with Magi on Instagram: @magifisherWant 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. | 34m 47s | ||||||
| 4/1/25 | KT Merry on Grit, Business Clarity, and Showing Up for the Long Game | From wrangling horses on a cattle ranch to building a globally recognized brand, KT’s path is defined by grit, resilience, and a fierce loyalty to her vision.We talk about betting on yourself before anyone else does, the mindset required to build a sustainable creative business, and the power of honoring the season you're in—personally and professionally. KT also opens up about her spiritual journey, how she balances constant travel with wellness, and why she believes structure is essential to support the artist.This conversation is an invitation to dig deeper—not just into your business strategy, but into your purpose, your boundaries, and your long game.What We Cover:KT’s unexpected path from cattle rancher to luxury photographerThe moment she walked away from a secure income to bet on herselfWhy business clarity matters just as much as creative talentThe power of structure in supporting artistic freedomHow KT stays grounded while living life on the roadNavigating seasons in business and learning when to push vs. pauseBuilding a creative life anchored in spiritual practiceThe importance of loyalty to yourself—especially when it’s inconvenientActionable advice for creatives seeking clarity, alignment, and longevityLinks & Resources:Instagram: @ktmerry and @ktmerryeducationWeb: ktmerry.comWant 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. | 43m 42s | ||||||
| 3/26/25 | Fluidity Over Formula: How Joel & Justyna Capture the Soul of a Wedding | In this episode, I’m joined by husband-and-wife photography duo, Joel & Justyna—artists known not only for their striking images but for their quiet, poetic approach. From fashion runways in Paris to editorial sets photographing dignitaries like HRH Queen Elizabeth II in Canada, their journey to wedding photography is anything but traditional. Together, they’ve built a career rooted in empathy, restraint, and the ability to read the rhythm of a wedding day like a seasoned musician.We talk about the chemistry that comes from photographing as a couple, how their rebrand reflects the imperfections they intentionally preserve, and the beauty of stepping back to truly let moments unfold. Their philosophy is rooted in nuance—tuning into energy, anticipating the unexpected, and capturing weddings not as productions, but as living, breathing memories.You’ll hear:Why they describe themselves as “composers of memories”How fashion influences their work—but never dictates itTheir perspective on quality over quantity and the power of saying noWhat it's like mentoring new photographers in today’s wedding landscapeHot takes on boutonnières, shrinking wedding parties, and texting clients after hoursSubscribe 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.Whether you're a photographer, planner, or someone who appreciates thoughtful storytelling—this episode is an invitation to see weddings (and the work we do) through a slower, more intimate lens.Links + ResourcesFollow Joel & Justyna: www.joelandjustyna.comInstagram: @joelandjustynaWant 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. | 45m 42s | ||||||
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