Sean Finelli is the founder and lead director for The Roman Guy, an Italian tour company based in Rome. MiLLENNiAL caught up with Sean to learn why he traded his career as a Wall Street broker for a life as a tour guide in Italy.

What inspired the move from a life in finance to now living in Italy running a tour company?

Dr. Seuss.  I hate to admit it, but I did well during the housing crisis. I could have stayed on Wall Street and became a top 1%er, but I left and moved to Italy because I was tired of waiting.

Dr. Seuss wrote a book called “Oh the Places You’ll Go” and there is a spread dedicated to “the waiting place”. He speaks about waiting for the train to come, the rain to go, a string of pearls or a pair of pants. We all wait, but he points out that you should enjoy every moment instead of being complacent and waiting for your next thing. Wasting away in a job you don’t like, so you can afford your next vacation or wristwatch.

At the time I wasn’t enjoying my life in Finance.  I was just waiting for paychecks to buy pants and pearls. I think more adults should listen when they read Dr. Seuss to their kids. The world could use more listeners.

This spread in Dr. Seuss’s book really hit home. So I just left.

At the time, I was working on Wall Street while I was in school, part time trying to finish my BA. As I approached graduation I got a few job offers and didn’t think long about my next move. I packed my VW on the way to my last exam and I was gone before I got the results. I was ready to move on in life and do something more meaningful, something of my own. Something that would help my future family avoid the waiting place. That’s why I left. I didn’t want to wait and I didn’t want anyone connected to me to have to wait either.

I started a tour company by accident.

I love learning, and history is of huge interest to me. When I arrived in Italy, I jumped right in and started soaking it up. Reconnecting with relatives, learning the language, spending a lot of my time getting lost in Italian history books. I soon began working as a tour guide and felt a natural fit with my connection to Italy and my love for storytelling and customer service.

While on this journey, I noticed that most companies weren’t providing customers with the experience they were looking for. I was on a quest at the time, and feeling bold, so I started approaching people on the street and offering my services.

From there, one thing led to another, and before long I had the name “The Roman Guy”. It wasn’t a company at first, it was me taking the leap, but it became that soon after. I invested a lot of time and energy into it – promoting the brand however I could afford to, but eventually it became too big for one person.

So, I found another like-minded guy who was looking to create something of his own too, and things took off. It was a lot of hard work, but along with my business partner Brandon Shaw, we’ve been able to create one of the leading tour operators and Italy travel companies in Rome, gaining great recognition in the travel industry, from the likes of Lonely Planet, Forbes Travel Guide and more. We were even included in Entrepreneur Magazine’s 360 list in 2016.

It’s incredible what you can achieve with a strong dose of tenacity. By keeping at it and trying everything you can think of to reach your goals, you achieve almost anything.

“Think left and think right and think low and think high. Oh, the thinks you can think up if only you try!”

― Dr. Seuss

Millennial Magazine - Profile-Sean-Finelli

How are The Roman Guy tours different from other tours offered in the area?

I often ask myself that same question. You have to continuously question yourself and your products. Look for reinforcement from your market and dodge complacency like the plague.

Our unique business ingredients are a mix of value, immersion, passion and service. We are a passionate team, on a mission to provide our customers with the most unique Italian experiences, immersing them in the culture of Italy, and doing it with topnotch customer service.

When it comes to our tours and experiences, first and foremost, we always look for unique selling propositions. Something that can differentiate our products from the broader market, satisfy the needs of customers, and offer opportunities for press.

If you think tourism nowadays, you think of “skipping the lines”. We understood a while back, that this had to be a given for us – any local fool could find a way around lines and try to sell it, so we always look to take it a step further for our tours.

The Colosseum Dungeons tour is a great example.

Beyond skipping the lines, we’ve also managed to structure a deal with the Colosseum so we can go to restricted areas below the building. They actually open a gate locked with chains for our group to pass into an area completely restricted from other visitors. We also walk out onto the Arena Floor where the gladiators once fought, along with other restricted areas.

We work to do this on all tours – offering more than the normal.

We have always thought the USP is the most important thing, but we’ve maintained the highest level of customers service regardless of how much a customer spends. Customer service is right up there with our USP for each tour, and it is a big part of what drives our business and keeps us open.

I ask every person I hire “Who pays your salary?”. They understand very quickly that customers pay our salaries and they should be treated as the boss. Without people purchasing our tours and services we are all out of jobs.

Tied in with that, I think our website has a great user experience. All the info you need is accessible and there are NO hidden fees. This is very important, as the experience we give customers online is an extension of the service we give offline. It’s a 360 degree approach, aiming to make it easy and pleasurable to customers at every point of interaction.

Apart from that, we’re a fun and friendly bunch of people. This comes through in our tours, in the way we interact with clients. We’re very personable and want customers to relax straight away and to enjoy themselves.

Explain some of the challenges and rewards of being an expat in Italy and what it is like to run a business there.

When I didn’t speak the language it was difficult. Difficult is actually an understatement. But learning the language and assimilating to the local culture has been a defining feature in my life. I am an Italian citizen (on top of American), but never actually promoted that until I felt like one. That took years.

Local politics have also been very challenging. We were running these environmentally friendly tours on electric golf carts. These amazing 7-passenger vehicles could manoeuvre all over the side-streets, perfect for Rome. We had all the licensing to do it, customers loved it, and most importantly, it stopped 500kg of Co2 from entering the local environment each year – but they shut us down anyway.

We were so confused as to why, but one thing most expats in Italy will tell you, is that you can’t ask why here. Nothing would get done if you didn’t just accept it and find another way forward. I normally don’t like taking no for an answer, but you’ll waste time trying to get answers here. It’s better to pivot, change strategy and move on.

I guess challenges only make you stronger, and that facing situations like this regularly, train you to find solutions for anything.

What type of traveler is ideal for The Roman Guy tours?

This is a tough question, as there are many different types of travelers we cater to. I really don’t like to bundle people up into demographics. However, if a traveler wants to experience Italy in an immersive way, avoid the crowds, have lots of fun, and be treated like a VIP even if they only have $100 or less to make it happen – then we’re your guy.

If terms of our offering, we offer two product categories, Trip Planning and Small Group Tours.

Trip Planning is our more comprehensive service for people who have a healthy budget to travel on. This is a comprehensive service that takes the guesswork out of travel. We charge a planning fee and you get a local expert. It allows travelers to focus on their jobs and personal lives, instead of trying to filter through all the online noise and information to plan their trips. We enjoy planning it all, and have never had anything but a great review.

Our minimum budget is about $8k for two people for an 8 to 10 day trip. That doesn’t include airfare or meals.

Currently, millennials don’t use this Trip Planning service much, as most of them haven’t traveled enough to know how tough it can be to plan a trip. Give it another 5 to 10 years and we’ll get that demographic.

A majority of our business is made up of Small Group Tours. Experiences under one hundred dollars that have USPs. We currently run them in Rome, Florence and Venice.

Two of our most popular being our VIP Colosseum Dungeons Tour and our VIP Privileged Entrance Vatican & Sistine Chapel Tour. We also run a lot of food tours, something we’re expanding in 2017. These types of experiences sell to everyone and anyone traveling to Italy that speaks English. You get to skip the lines, gain access to restricted areas and more, all for a great price.

Besides our Small Group Tours and Trip Planning, we also have Private Tours, Shore Excursions, Day Trips, Combo Deals and lots more.

What new tours will you be offering in 2017?

We’re constantly looking at new experiences we can share with clients, and have lots happening in 2017. The industry is maturing and we’re working hard at keeping up and forging forward.

In 2017 we’ve been working on expanding our product mix in ways that make it more accessible to a wider market. There is lots of new this year.

Our “Gladiator Experience” Colosseum Arena Floor Tour makes the coolest of the restricted areas accessible to millennials, boomers and families, at a great price. Standing on the Arena Floor is something special, and a cool spot for those Instagram snaps.

Our Colosseum and Vatican Express Tours make the experiences accessible to those who don’t have much time or who just want to focus on the highlights in the shorter period.

Our Electric E-Bike Tour allows travelers to see Rome in a totally different way, and it’s eco-friendly.

We’ve even created a selection of Family-Friendly Kids Tours, that make visiting places like the Colosseum and Vatican an interactive super fun experience for the little guys.

One of our latest additions, that I’m really excited about, is our Cicchetti Food tour in Venice. The Venetians are known for their fried seafood. They serve them at these bars where you grab a glass of wine and you buy different types of finger foods. Total street food. Most have an outdoor bar to lean up against and enjoy your wine and treats.   We’re going to explore the inner reaches of Venice and open up places that people simply wouldn’t find on their own.

We’re also focusing on inexpensive experiences. $39 will get you a 1-hour boat ride through Venice with Prosecco to toast to. 6 to 8 people max in a boat, but if you are one person you can still join and it’s only $39.

We’ve got a ton of other cool things happening. Not to mention, there is talk that an office is opening up in Paris.

To learn more about Sean Finelli or to book a trip with The Roman Guy, visit …