How Sean Finelli gave Wall Street up for Rome and built his own tour business from scratch

In this candid and in-depth episode of Tourpreneur, I chat with Sean Finelli, CEO of The Tour Guy. 

Sean Finelli walked away from a lucrative analyst job on Wall Street to move to Rome. He worked numerous bar and restaurant jobs to pay his way and then found himself selling tours on the streets of Rome. 

This is when his life changed.

Sean worked his way up from selling tours for others outside the Colosseum to building his own successful tour business. Sean reveals he suffers from dyslexia but also shares how he has turned it into an advantage.

March’s Daily Brief and the Tourpreneur Podcast is kindly sponsored by Checkfront, the booking platform trusted by over 5000 tour and activity operators around the world. You can start your own free 21-day trial over at

You Can’t Take the Financial Analyst Out of the Financial Analyst.

Sean Finelli was fed up at the Wall St bank and started crunching the numbers in his head to figure out how much money he could make on his own. 

He believed he could achieve financial independence on his own much faster and moved to Europe. 

Sean decided on Italy.

His original plan was to live in Rome for a year or two, learn the language, and find niche jobs.

“One day I walked up to the Coliseum, and I saw all these people selling tours and the long lines which accompanied tours. So I started selling tours on the street in front of the Colosseum.”

Sean Finelli

“When people walk into a store, they usually think about how this store smells nice, or are interested in the cool products on the shelf. I look around at the average purchase price of products, how many people walk through the door and start calculating. That’s how my mind works.” Steve is an analyst at heart and started to compute store size, rent and other quantitative factors.

“I just start calculating, thinking how much profit that store can make and how many stores you need to build to make a living or start a company.” He’s been this way for as long as he can remember.

So when Sean decided to land in Rome, his mind went into calculation mode. He looked around and realized a large amount of opportunity. He remembers his first impression of Rome being disorganized and the many complaints about inefficiencies. Steve saw tourism and travel opportunities and the ability to make an income.

Sean’s most profound value is to live an interesting and cool life filled with memories. “The most interesting and most memorable memories are the ones that happen on vacation.” 

He remembers standing in front of the Grand Canyon for the first time as a child with his dad. “When you travel to new places, you remember them.”

In this episode of the Tourpreneur Podcast, we’ll talk about his company’s values, his streamline work processes, and how he runs his tour businesses.


The Tour Guy on the Web

The Tour Guy on Instagram

Headout: Discover Attractions