top of page

Dario Castagno: a Category of 1, and the 14 Year Sales Cycle

Me with Dario Castagno, Tuscan author and tour guide

I'm always looking for great marketing and sales application stories, and I just lived one out this past week, the story of the Dario Castango, Tuscan author and tour guide, and the account of my 14 year sales cycle with him. When Dario learned I was a marketing and sales consultant, he said "that's one thing I haven't been very good at." Personally, I think Dario is selling himself short; we can find good examples of a lot of fundamental principles in how his business had developed over time, and I shall pull these out as we go. But let's start from the beginning.

In 2005, my wife and I visited Tuscany for an anniversary trip. We visited a monastery (that shall remain nameless for reasons I shall reveal in a moment) and picked up a copy of a book in the gift shop called "Too Much Tuscan Sun, Confessions of a Chianti Tour Guide". We didn't read it until we got home, but were in stitches over the hilarious anecdotes, but also enchanted by the book's sense of place and author Dario Castagno's love of the sites he shared with his visitors. We said to ourselves, "next time we go back, we'll have to look up this Dario fellow and take a tour." This book turned out to be one Dario's key marketing resources, and it set in motion a pipeline of clients that continues to this day.

Principle: Define your target market and go where they are. As a tour guide, leaving books at a place where people who might be interested in tours are likely to go makes perfect sense.

Years come and go. I've been back to Italy more than once for business and pleasure, but never to Tuscany. The book has been loaned out on occasion to other people who have visited or intend to visit Italy, and always returned to its place on the shelf. I'd always been interested in a tour with Dario, I was just not in a position to buy.

Principle: There's a big difference in audience between "not interested, ever", and "not interested now". The dreaded "no decision" deal killer in sales sometimes is simply a "not interested now"- knowing the difference can help us determine which clients to keep re-engaging for when the time is right.

Then, in 2019 my daughter signs up for a college semester abroad in Florence, and we start planning a long-awaited return to Tuscany. My first email was to Dario. I explained how we had his book from all those years ago and asked if he was still doing tours. " Ciao...yep, I'm still conducting tours!" was the reply. "Book us for the Fattoria Tregole visit" was my answer. Fourteen years after I had bought the book, the book finally "sold" a tour booking for Dario. But there's more to the story than that.

Prior to the visit, my wife mentioned our upcoming tour to one of her clients. Turns out this client not only knew of Dario, she had taken tours and had many of his books that he had written since the first one. She enthusiastically recounted her experiences, including driving to Cleveland to see him on a book tour. While we didn't need any encouragement that our upcoming tour was a good idea, the reinforcement from someone we knew further increased our anticipation for the tour. The majority of Dario's clients have come through a word of mouth network of recommendations from family, friends, friends of friends and so on.

Principle: Social proof says that we put more stock in recommendations from people we know than any other kind of evidence that something is worthwhile.

On the visit, between our tour of some Eutruscan tombs that Dario and his friends had discovered as teenagers, a tour of the 1000 year old Tregole wine cellar, and a beautiful Tuscan lunch, we discovered some interesting details about what had happened between 2005 and today.

The first is that all those initial self-published books that Dario had left in gift shops for marketing purposes around Tuscany turned out to be pretty much just for marketing purposes, because in the end, he often wasn't able to collect on the promised 50/50 split of the sales. "The monks were the worst," Dario said. "They never paid my invoice for any of them." Dario hadn't gotten one euro cent from that initial book I'd bought. As Chris Voss says in Never Split The Difference, reciprocity is a powerful norm across human cultures- when one party gives, the other feels obliged to return. Certainly Dario hadn't intended to invoke this response by telling this story, he was just talking about how the book came to be where we'd bought it in the first place, but it did make me immediately decide to buy three books from him this time instead of one.

Principle: In negotiations, calculated escalations or unrelated surprise offers can trigger a reaction of reciprocity in the other party.

The second is that due in part to the increasing popularity of visits to Chianti, and wine tours in particular, a category which Dario had more or less created-- "the tax authorities didn't even have a classification for my business when I started it," he told us-- the authorities decided to pass laws to regulate who was "allowed" to be a tour guide, complete with examinations and licenses.

Dario notes in the forward to his third book: "I refused to solicit permission to practice a profession I had, in Chianti, practically invented. And considering my appetite for [guiding minibus tours] had waned while my literary career waxed, I decided to give way to a new generation."

But of course this story is about us taking a tour with Dario, so what is he now, exactly? He's a category of one: The ex-tour operator, author, conversational tour guide, and as he puts it, the kind of person that strange stuff always seems to happen to, which provides an endless source of interesting anecdotes. The reason Dario is in a category of one among tour guides is that he himself is part of the product. It's not a wine cellar tour. It's Dario doing a tour that happens to have wine.

Principle: Differentiation comes when you define yourself as a category where you are the only thing in it.

The final principle for marketing and sales is that sometimes our efforts can take time to mature. The rush for immediate ROI tends to be focused on the people who are ready to buy now, and often overlooks those who are truly interested but just not ready yet. In the case of my interest in Dario's product that wait time was 14 years.

So, after all that time, was it worth it? Absolutely. As expected, it was like no other private tour we had ever booked, it seemed more like catching up with and old friend you hadn't seen in years. And that was part of the charm. A category of one. Thanks Dario. Catch up with you next time we're in Tuscany.


Here are a selection of Dario's books available from Amazon (and yes, he gets paid if you buy the kindle edition).



*As of April 2022, Pardot has been renamed Marketing Cloud Account Engagement, as part of Salesforce's effort to organize all the marketing products under the same platform umbrella. "MCAE" is simply the same Pardot we know and love under a new name. The product is temporarily being referred to as "Marketing Cloud Account Engagement powered by Pardot."   

Did you find this article useful?  Buy me a coffee. 🙂

Want more tips? Subscribe and be the first to know of new coffee-worthy content.

Thanks for Subscribing!

Need some help?

Consultations offered on a pay-as-you-go basis by the hour.  Buy hours below and I will schedule a session at your convenience.

bottom of page