It’s 10 a.m. on Saturday April 14, 2024, and a new part of my wife, Lisa Grassi Blais, and my lives in Abruzzo, Italy is set to begin.

In about five hours, we will welcome our first guests to our second all-inclusive vacation location, The Baron’s Estate, in our adopted town of Torre de’Passeri. We’ve taken the place from rundown and somewhat neglected to something beautiful in four months, which is now officially a record here in “I’ll get to it later” southern Italy.

We are proud of what we’ve achieved, and so are the people who helped get us here. The contractors, the cleaners, the groundskeepers, our staff, I could see satisfaction behind their faces this morning as we put last-minute touches into place.

As our groundskeeper Angelo took the plastic off the last lounge chair by the pool, he stood back and took in the beauty he helped create, closed his eyes, took a deep breath, and smiled.

“E fatto,” he said. It’s done.

Well, not quite. Our contractor is still installing a piece to the hot water system to boost capacity. The wifi guy is sitting at a computer dicking around with codes and names. The house staff are running about doing the things I never think about: flowers, soapy things, and I think doilies.

The Baron’s Estate is miles ahead of where we were when we opened our first location in Torre de’Passeri, about 150 kilometers east of Rome in the Pescara River Valley. On May 1, 2016, we had the basics, but some of it was really basic.

In contrast, the Baron’s Estate looks like it walked out of a movie set. In fact, as I write this a pro photo shoot of the place is underway. (We’ll be posting the photos next week on our website and social media.)

Lisa and I are miles ahead of where we were almost eight years ago too. After about 2500 guests at the Villa and hundreds of great reviews, we know people like our packages. We know the food is good, the tours are cool, and, more importantly, our staff is absolutely fantastic with the right blend of professionalism, exuberance, empathy, and dedication.

I know these things empirically. These are facts.

Still, it’s a big undertaking, and my old friend anxiety has paid me a visit in the last few days.

It’s not as bad as it was in 2016. Instead of sleepless nights, I wake up worrying about something dumb (it’s always something dumb), but I calm down quickly and get back to sleep instead of lying awake for hours catastrophizing like an idiot.

I’ve worked hard at not always being on the lookout for approaching disaster, which was my nature state for decades. I’m usually good at it. But as we sprinted to the finish line of the Estate, I got run down.

It’s there in my stomach. A slight nausea crossed with a sinking feeling.

“Who are you to be doing this?”

“What if people don’t come?”

“What if it’s not a financial success?”

“Maybe people won’t like it?”

The doubt.

Just writing those sentences flipped my guts a bit, and I needed a deep breath. I know the answers to these questions.

Why not me? Why not us? We’ve already done this once.

We already have 200 Estate bookings this year and more than 100 for 2025.

We are already at break even in our first year.

We’ve had 100 guests who stayed at the villa look at the Estate, and they all think it’s awesome.

You got this Jake.

It’s now 1:30 p.m. and our head guide Luca Santovito just texted saying he will arrive with the first guests in a about 45 minutes.

He’s early. It’s time to flip the switch from getting the place ready to operations.

Left to Right - Eva, Daria, the most handsome man to ever walk the earth, Tiziana, Nunzia, Mirela and Eleanora.

Our house manager Eva is inspecting the rooms and fussing over flower arrangements.

Our team is strong. We have a tireless house crew. At 2 p.m., we pose for a victory photo.

We have great guides. We have great food. We have great tours.

Hell, we have a masseur set up permanently in a wicked-cool gazebo in the Estate’s botanical garden.

Steady as she goes Rupert. Just do what you’ve always done.

Work hard. Work smart. Be yourself.

You got this.

Now, let’s go.

It’s now 3:30 p.m., and the first guest arrived an hour ago. They got out of the vans and marveled at the Estate. I did the orientation to a chorus of wows and compliments.

The guests are on the terrace now enjoying drinks and snacks.

My stomach is settling.

Breath comes easy.

At 6 p.m., I do a tour orientation for 16 people at the villa. They are happy and love the tour plan. At 7 p.m., I do the same for 13 people at the Estate. They are already having a ball. (It helps that house wine and local beer are included in our packages.)

At 8 p.m. I eat at the Estate. The guests love the meal and are effusive about the place. At 10 p.m. on my way home, I drop by the Villa. There are five guests in the living room. They loved the meal. They love the Villa.

I leave for home. Have a glass of wine and speak to Lisa for a few minutes. I’m asleep seconds after I hit the pillow.

I got this.

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