Wine and Dine Me

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 Cover

• The difference between the “penny market” and “silver dollar market”
• Why strategies that worked while building your business may stop working at the next level
• How to identify a niche using your existing clients and past work
• The psychology behind Rachael’s “velvet rope” positioning
• Why fewer inquiries can actually signal stronger positioning
• Positioning, press, paid speaking, and strategic partnerships
• Why Rachael views press as a pricing tool rather than a vanity metric
• Why relationships can produce a stronger return than traditional marketing
• Selling to clients for whom budget is not the primary concern
• Why founders should personally take high-level client calls
• Turning a “sales call” into a connection call
• Why women often struggle to price their expertise confidently
• How personal style, headshots, and website hierarchy influence positioning
• Why your existing portfolio may contain work you are overlooking
• Building a selective business while still protecting family life

Guest Info

Rachael 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 Johanson
Instagram: @rachaeljohanson_

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For more candid conversations about hospitality, sophisticated events, leadership, business, and the standards behind unforgettable experiences, follow The Wine and Dine Me Podcast.

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Hosted by Reagan Prechter, founder and creative director of Reagan Events.

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 Cover

• Starting in the events industry at 12 years old
• Scaling without sacrificing quality
• Creating standards before expanding a team
• Why talent without professionalism is not enough
• Reading the room through music, tempo, and volume
• Building operational systems that make planners’ jobs easier
• Delegating without micromanaging
• Hiring slowly and setting clear expectations
• Finding growth opportunities inside your own CRM
• Serving different price points without compromising the product
• Genuine relationships vs. transactional networking
• What becoming a groom taught Jordan about weddings
• Why the couple always has to remain at the center

Guest 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

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 Episode

Reagan and Alison discuss:

• Building a destination event company before Instagram and online vendor directories
• Why access to endless inspiration may be weakening originality
• The truth behind industry lists, visibility, and overnight success
• Maintaining relationships with clients beyond a single event
• Building a company that is larger than its founder
• Accepting that talented employees will eventually leave
• Hiring the right mix of employees, freelancers, and creative partners
• Collaborating with designers and production companies without ego
• Investing thoughtfully in mentorship, education, and industry relationships
• Why guest experience remains the strongest point of differentiation

About 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 & 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 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 means
• Why medical support is becoming a thoughtful layer of event hospitality
• The difference between EventDox and traditional EMT coverage
• How medical care can be integrated discreetly into weddings and private events
• The liability planners, venues, and hosts may not realize they are carrying
• Why relying on a guest who happens to be a doctor is not the same as having medical coverage
• Wellness lounges, IV support, and on-site medical care for guests and event teams
• Building a business from lived experience and industry need
• Motherhood, resilience, postpartum anxiety, and asking for help
• Why preparedness should feel like care, not fear

Guest Information

Guests: Caroline Brown and Julie Livingston
Company: EventDox
Email: [email protected]
Instagram: @eventdox

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 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 event

Connect with Anja Winikka:
Instagram: @rafanellievents
Website:  rafanellievents.comListen & 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 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 life

Connect with Anja Winikka:
Instagram: @joinfreeda
Website: https://www.joinfreeda.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.

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 Episode
Reagan 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 move

Connect with Lauren Taylor:
Instagram: @lefleursociety / @laurentaylorattorney
Website: https://www.lefleursociety.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.

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 partner

Key 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: @alexschon
Website: www.alexschon.comListen & 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 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 days
• How German literature (and German work habits) shaped Laura’s planning brain
• The first wedding she ever produced, and why she asked two questions first
• What discretion looks like when paparazzi are actively trying to get in
• The real reason top-tier clients choose “simple” food and simple moments
• How 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 place
• What The Wedding Prive is, and why multi-destination weddings are the next frontier
• Laura’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 partner
• 04:24 German literature, Goethe, and the pivot into events
• 10:35 Her first wedding came from a corporate guest, and she never “sold” planning
• 14:55 The private island birthday story and what discretion actually requires
• 20:07 The Doha connection that opened the door to royal work
• 29:36 How Laura learns a new culture: sit, watch, listen, decide for yourself
• 33:58 Her guest-experience non-negotiable: local performance over predictable extras
• 36:24 The Wedding Prive and the operational reality of multi-destination weddings
• 48:52 Final advice: trust your gut, stop people-pleasing, lead the room

Connect with Laura:

• Instagram: @theweddingprive, @ellessevents
• Email: [email protected]
• Website: The Wedding Prive

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 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.