This is a long email, but wanted to share some background on a project we’ve been working on. You’re getting this because one of us knows you and we thought you’d be interested in following along or you can unsubscribe below.

TL/DR: We’re working on finding, acquiring, renovating and launching a boutique farm stay resort in Italy and are starting this newsletter to share the journey.

For the past decade or so, Dan and I have brainstormed about what it takes to create the worlds best guest experience. We spend hours discussing the minutia of things that go right and wrong when we stay at a hotel or resort or vacation rental. Why is this a thing for us? We don’t really know, but we love talking about it. We work in software not hospitality so what gives us the right to pass harsh judgement on a bathroom with an overly complicated shower? We’re middle aged white men so we’re experts on all things.

We’ve brainstormed many different ideas. A fitness bootcamp or maybe a cooking school or summer camp for adults. Over time our idea evolved to a mini resort set on a farm offering local experiences. We like the idea of casual luxury and creating a place that feels like you are staying with friends or family (the ones you like).

This business is different from a software startup. We had to shift our mindset from tech startup to real estate and hospitality. We want to create a place where we can spend extended time over the coming years. We want to create a place that draws from the best of our favorite hotels, resorts and guest houses we’ve visited. We don’t want to run it day to day, so it needs needs to be big enough to support a management team but small enough that it doesn’t feel like a big brand hotel.

The objective isn’t to make a massive profit, rather it’s to lose as little money as possible and hopefully break even someday. Our priority is hiring and investing in a local team and building a place that creates memorable experiences for our families, friends and guests. We want to create the best guest experience. It’s not a particularly wise investment as these types of properties and projects are illiquid and can take years or decades to sell. But the idea keeps drawing us in.

As many of you know, Dan likes to cook and that could be helpful to our project. Here he is looking condescendingly down on at our instructor at cooking classes imagining how he could do it better.

Since Dan didn’t have any true hospitality experience he decided to marry Roxanne who does and would give us credibility in case we we decided to actually attempt a hospitality project.

I grew up on a farm, so maybe subconsciously that was pushing me toward making a risky and ill advised investment decision of buying a fixer farm thousands of miles away. Margo didn’t specifically say no, which is kind of like a yes. So we started looking.

Our first thought was Spain. Our kids speak Spanish. Roxanne speaks Spanish. Dan and I could probably learn Spanish. We found a real estate agent and started looking online and properties in the Costa Brava / Girona area. We weren’t finding anything that caught our eye.

Then last August, I went to back to Italy with Olin and my friend Michael. We traveled to Montepulciano where our friends Bobby and Megan lived while we lived in the Netherlands in 2016-2018. Bobby loved the local wine so much he started a side business importing wine from small winery’s called Strade Bianche Wines but that’s a whole other story. His partner Andrea is Italian, lives in Montepulciano and has become a friend.

We arrived during the Bravìo delle Botti, a week long celebration that ends with teams from each neighborhood racing a wine barrel up through the city to the main square at the top, passing out, and then being carried off in an ambulance from exhaustion and the heat. It’s taken very seriously. It’s a perfect week to visit the city as it’s a homecoming and reunion for locals that have moved away. Everyone comes back to town and each evening the eight Contrade (neighborhoods) throw a street party with food, BBQ, wine and on some nights, a discotech.

Our friend Andrea was incredibly welcoming and invited us to join the dinners, took us to his favorite wine bars and to dinner at his fathers place, Ristorante La Briciola. We felt welcomed and experienced the type of hospitality that we want to create for others - the feeling of traveling with a local, a friend and with a bit of an insider perspective.

While were in Montepulciano, Andrea connected me with his friend Marta who showed me several local agriturismos that were for sale. There are over 18,000 in Italy and they are everywhere. An agriturismo is a rural accommodation that blends the charm of traditional farming with the hospitality industry. These establishments, often working farms, offer lodging and meals to guests, providing an experience of rural Italian life. Guests can stay in a rustic stone farmhouse, enjoy homemade meals prepared with fresh, local ingredients, and even participate in farm activities like harvesting vegetables, feeding animals, or wine tasting.

Italy established the concept of agriturismos in the 1980s to support the agricultural sector and preserve rural communities. The government recognized the need to diversify farmers' income sources, especially during times when agricultural profits were low. By opening their farms to tourists, farmers could generate additional revenue, ensuring the sustainability of their agricultural practices. This initiative also aimed to promote rural development by drawing tourists to less-visited areas, stimulating economies and helping to prevent rural depopulation.

Montepulciano, famous for it’s wine, is in the middle of Tuscany, which is a much larger and geologically diverse area that I had envisioned. One of the key aspects that make Tuscany special is its commitment to maintaining the traditional look and feel of its towns and countryside. These regulations limit new construction and enforce strict guidelines on renovations, ensuring that any new buildings or modifications blend seamlessly with the historical and architectural style of the region. This includes the use of traditional materials like stone and terracotta, as well as architectural features such as red-tiled roofs and wooden shutters.

The Italian government implemented these restrictions to safeguard the character of Tuscany's landscape. For example, in the Chianti region, regulations prevent the construction of large industrial buildings and ensure that any new development respects the traditional rural environment. This helps preserve the iconic rolling hills, vineyards, and olive groves that are synonymous with Tuscany.

We fell in love with the area as most people do, and decided to focus our search here, even though it seemed cliche. While we didn’t find the perfect property on the trip, it did convince me that we should focus on Italy for our hospitality experiment.

On our last day when were back in Florence, Andrea introduced us to his friend (also named) Andrea who is a hospitality consultant and has been advising us on the project. He is an all around great guy who also competes in the brutal calcio storico which is a mix of martial arts, rugby and football.

On our final night, Andrea found us a table at at Buca Mario for a farewell steak and gnocchi dinner (restaurants always seem to keep an extra table for friends). Bistecca alla fiorentina is a specialty of the area, it’s only cooked one way, rare, and is exceptionally good. After a great trip, meals, wine and conversations with new friends we were sold on Italy as the perfect spot for our hospitality experiment.

When we got back, Dan and I debriefed and made a list of all the things we wanted in a property and started wondering if we could really make this happen.

Things we wanted:

Unfortunately there is no MLS or Zillow in Italy and searching for real estate in Italy feels like a wild goose chase. Agents often have only one listing and in Italy, the agent represents both the seller and potential buyers. We searched through a labyrinth of outdated online listings that never share the address (we found hack and more on that later). We’d think we found the perfect property, only to discover it was sold three years ago. Photos are blurry or artistic shots of a single rustic window, leaving us guessing if the house even has walls. And when we finally connect with an agent, they would send us something completely different—a "charming fixer-upper" that's actually a crumbling ruin. It's a twisted treasure hunt. This is worthy of it’s own lengthy post at some point but we did eventually find some helpful real estate agents and Marta was a great help with our search in Montepulciano.

I made a few return trips to look at more properties and we narrowed our search down to three finalists. We both have a lot of wild ideas that go nowhere, but this one is starting to feel real.

Next up we’ll share the finalists.

eric, margo, dan & roxanne