Wine and Dine Me Podcast

This is a home to episodes of The Wine and Dine Me Podcast - Reagan’s candid take on hospitality, sophisticated events, leadership, and the standards behind unforgettable experiences. Through conversations with planners, photographers, designers, hospitality leaders, and other creative operators, the podcast offers an honest look at what actually makes something exceptional.

Expect behind-the-scenes perspective, thoughtful conversation, and content rooted in taste, service, and substance.

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Reagan Kerr 9/21/26 Reagan Kerr 9/21/26

Rachael Johanson

What changes when your business no longer needs more clients, but the right clients? Rachael Johanson joins The Wine and Dine Me Podcast to discuss positioning, pricing, sales psychology, personal branding, and her “velvet rope” approach to attracting fewer, bigger, better opportunities.

Reagan Kerr 9/1/26 Reagan Kerr 9/1/26

Jordan kahn

Jordan Kahn, founder of Jordan Kahn Music Company, joins Reagan on The Wine and Dine Me Podcast to talk about scaling a creative business without sacrificing quality, building clear standards, creating stronger industry relationships, and why hospitality should remain at the center of every wedding experience.

Reagan Kerr 8/14/26 Reagan Kerr 8/14/26

Alison Hotchkiss

After nearly 25 years in the events industry, Alison Hotchkiss has learned that longevity has far less to do with recognition than with relationships, consistency, adaptability, and how people feel working with you. Reagan sits down with the founder of Alison Events to talk candidly about leadership, building a strong team, collaboration, guest experience, and what it really takes to build a creative business that lasts.

Reagan Kerr 6/1/26 Reagan Kerr 6/1/26

Julie Livingston & Caroline Brown

In this episode of The Wine and Dine Me Podcast, Reagan sits down with EventDox co-founders Caroline Brown and Julie Livingston to discuss concierge event medicine, guest safety, planner liability, and the quiet layer of care that protects high-touch weddings and private events before a medical moment ever disrupts the celebration.

Reagan Kerr 5/14/26 Reagan Kerr 5/14/26

Anja Winikka

Reagan sits down with Anja Winikka, founder of Freeda Network, for a candid conversation about visibility, influence, founder loneliness, and why trusted rooms matter more than ever for creative business owners building at a high level