Why No Algorithm Can Replace Local Knowledge ValiantCEO interviews our founder, Jesse Andrews, on leading a travel company through the rise of artificial intelligence.
Technology can plan a route in seconds. It cannot tell you which trattoria a family has loved for three generations. That balance is at the heart of this conversation.
Our Founder, Interviewed by ValiantCEO
A conversation about leading a travel company through the rise of artificial intelligence.
ValiantCEO, a magazine that profiles business leaders and the companies they build, sat down with Jesse Andrews for its interview series on AI leadership. The interview was conducted by Jerome Knyszewski and published in August 2025.
It covers how AI is changing travel, where it helps, where it falls short, and why Jesse believes handcrafted trips built on real relationships matter more now than ever.
Jesse Andrews, founder of Italy Vacation Specialists
Our Belief
A machine can suggest a restaurant. Only a person can tell you why it matters.
From a 5,000 Euro Grant to a Travel Company
Jesse was 23 and barely spoke Italian when she asked a mayor in Calabria to fund a website.
She had come to Praia a Mare to teach English, and wanted the world to know about the town. The mayor said yes. Word spread to other towns across the South, and along the way she built ItalianVisits, one of the early blogs about Italy, which grew into Italy Vacation Specialists.
Today we run our own fleet of vehicles and work with local guides, chefs, historians and artisans in every region. Our guests range from honeymooners to multi-generational families and corporate groups.
A street market in Sardinia
What We BelievE
Technology can help us work faster. It cannot replace someone who has actually been there.
What AI Can Do, and What It Cannot
A useful tool for the work behind the scenes, never a substitute for someone who has been there.
Jesse is candid in the interview. She has spent more than two decades writing thousands of articles about Italy, and that work can now be copied by a machine in seconds. She also finds that AI content is often generic and cannot tell a tourist trap from a hidden gem.
For Jesse, the answer is not to avoid technology but to keep people at the center of it. In the interview she describes AI as a useful assistant for the work behind the scenes, and a poor substitute for the judgment of someone who knows the place. A suggestion from a machine is only a starting point. What makes it worth recommending is the local knowledge of the people who check it, question it and know when something is better left out.
Every itinerary is reviewed by a person who knows the place
In Her Words
“Don't start with the technology, start with your values and your vision.”
Smarter Planning, Same Human Touch
Jesse expects AI to reshape travel within five years, and human connection to matter more because of it.
She sees plans that adjust in real time for weather and crowds, smoother logistics and greener routing. What will not change is the reason people travel: the stories, the people and the moments nobody could have predicted.
That is the balance we believe in. Technology can help behind the scenes, but the journey itself should be designed by people who know Italy.
The best moments in Italy still happen face to face