Unreasonable Hospitality: How to Make Every Guest Feel Like the Only One

Have you ever left a place and told everyone you know about it? Chances are, it wasn’t just the food or the product. It was how they made you feel. That feeling has a name: unreasonable hospitality. Lately, I’ve become a little obsessed with it.

In this October bonus episode of the Never Stop Dreaming Biggie podcast, I’m sharing what I’m learning and the stories that shaped me. I’m also sharing how we’re building it into the Holmestead from day one.

What is unreasonable hospitality?

The term comes from Will Guidara’s book, Unreasonable Hospitality. This year, he also released a field guide with Simon Sinek. The field guide turns the book into hands-on homework for your business. My friend Kat Warner is at their conference in New York right now, and honestly, I’m jealous.

The big idea is simple. Service is what you give people. Hospitality is how you make them feel.

When we serve someone, we’re usually doing something they paid for. Hospitality takes it a step further. It’s the extra touch, the experience, and the way you make someone feel seen. Plus, it looks different for every person.

Write your own unreasonable hospitality definition

The first exercise in the field guide asks you to define hospitality in your own words. Here’s mine:

Hospitality is the way someone feels the moment you meet them. It’s making them feel like they’re the only person that matters, and taking care of them from the moment they arrive until they leave.

People forget what you said. However, they never forget how you made them feel.

For example, you can get a burger anywhere. Still, you’ll drive across town for the place that makes you feel special. That’s even more true when you travel. You want places that stand out, do something different, and give you a story to tell your friends.

Personally, I try to look people in the eye and give them my full attention. I’m not perfect at it, especially with my phone in my hand. In fact, I’ve been called out for multitasking on calls. So I’m working on it, because the people in front of me deserve that time.

Unreasonable hospitality stories I’ll never forget

Next, the field guide asks you to write down your own hospitality stories. I started a section for them in our Holmestead master plan notebook. Here are a few favorites.

The French Laundry

Years ago, a friend gave me her reservation at Thomas Keller’s French Laundry in California. Yes, it was expensive. But the experience started long before we sat down.

They reached out ahead of time to ask about allergies and whether we were celebrating anything. They knew where we were staying and left a note there. Then, during dinner, they took us back into the kitchen. Afterward, they followed up to ask what we loved. Every detail felt intentional.

A white jean jacket from Fox

In high school, I loved 90210. My boyfriend kept saying it wouldn’t last a season. So I wrote to our local Fox station and begged them to keep it.

A few weeks later, a big box showed up. Inside was a thank-you letter from the general manager and a white jean jacket with 90210 on the back. I wore it constantly. That one small gesture taught me how much it matters when you go out of your way for someone.

Black Octopus in Park Circle

Missy, the owner of Black Octopus, kept inviting me to her new store whenever I saw her around Park Circle. There was never any pressure. She simply made me want to come.

When I finally stopped by, Missy wasn’t there, but her team was wonderful. We swapped stories, and as I left, they handed me a little bag of candy. It was small, but it sealed the deal. I went home and posted about it, and now I tell everyone to go.

A birthday at Bourbon & Beyond

On Brian’s birthday, we were camping at Bourbon & Beyond. I didn’t have much to decorate with, so I went to the camp store at 7:30 in the morning. A sweet employee offered to drive to Dollar Tree for me. I told her that wasn’t necessary.

Then, she told me to bring Brian back that afternoon. When we walked in, the team cheered for the birthday boy. She handed him a bag full of goodies, including a birthday pin and a giant hat. They even sang to him. Nobody required them to do any of it. That’s unreasonable hospitality.

Find your hospitality superpowers

Another exercise asks you to name what makes you unique. Mine include being organized, reading a room quickly, and bringing diverse groups of people together. I also love connecting people who can help each other grow.

Brian’s superpowers are completely different from mine. That’s a good thing. At the Holmestead Hideaway, we’ll balance each other out.

So, what are yours? Write them down and build your guest experience around them.

Unreasonable hospitality starts with your team

We often think customers come first. But if your staff isn’t happy, your customers won’t be either.

The field guide encourages you to discover your team’s strengths and ask better questions. For instance, during interviews, try asking:

• What was the first concert you ever went to?
• What would people be surprised to learn you excel at?
• What was your last vacation?
• What’s your favorite Girl Scout cookie?

Questions like these reveal who someone really is.

How we’re building unreasonable hospitality into the Holmestead

The way you do one thing is the way you do everything. That’s why we’re planning every touch at the Holmestead with care.

For instance, we want fun drinks with playful details, like a mermaid tail straw or a whale garnish as a nod to Bequia. We also plan to recreate favorite things we’ve found around the world, each with a sign sharing its story.

Birthdays will be a big deal, too. And yes, if you turn 50 with us, you’ll wear our family’s famous boob hat. Brian’s late father, Ron, started that tradition, and we’re carrying it on.

Most importantly, the retreat side of the Holmestead is about renewal for your mind, body, and spirit. It goes back to my first trip to the islands at 13, when I found clarity and healing. Every dollar will go to charity through the Homestead Angels nonprofit.

How you can be part of it

We need to raise more than $5 million to purchase the property and open by December 23, 2027. If you’d like to experience unreasonable hospitality like no other, consider becoming a Homestead Angel.

Even if you can’t give, you can still help. Share this post, tell a friend, and pray with us. The more people who know our dream, the more it will happen.

And tell me about your dreams, too. We’d love to support you.

https://theholmesteadhideaway.com/holmestead-angels

Listen to the full episode

Catch Episode 85 of Never Stop Dreaming Biggie wherever you get your podcasts, or watch on YouTube. Then grab Will Guidara’s book and field guide, and start writing your own hospitality stories.

Next month, we’re recording from Bequia while staying at the property we hope to buy. November is all about gratitude, so stay tuned.

Have a story about unreasonable hospitality? Email me at angel@sipindipity.com. I’d love to hear it.