If you looked at my CV, you would probably assume it belonged to several different people. I started out as a competitive soccer player. I trained as an electrical engineer. I then spent fifteen years playing poker professionally. Poker led me into investing, investing sharpened how I think about risk and systems, and eventually I found myself back on the pitch again, this time as a coach.
Those paths might seem disconnected. In reality, they all trained me to see structure, inefficiency, and leverage. Which is exactly why I ended up in Italy.
Living here has forced me to rethink what opportunity actually looks like, and what kinds of businesses make sense in Italy as opposed to everywhere else.
Shortly after arriving, I founded The Bridge to Italy, a business focused on the legal and logistical work required to obtain the Italian investor visa. We guide clients through the front end of the process, from structuring the investment and coordinating with attorneys and banks to managing documentation, compliance, and timelines. The business exists because I went through the process myself and quickly realized how fragmented and opaque it can be without experienced guidance.
After about half a year on the ground, one thing has become clear. Italy is full of opportunity, but it hides in plain sight. The best ideas here are not flashy. They do not scale overnight. They work because they solve real problems that Italians and foreigners alike quietly struggle with every day.
Below are three areas where I believe entrepreneurs can build durable, meaningful businesses in Italy.
Activity based English programs for children and adolescents
Italy has a well known generational gap when it comes to English proficiency. Many highly educated adults speak little English, or speak it with discomfort. Parents understand that this puts their children at a disadvantage in an increasingly global world.
At the same time, children are already exhausted by formal education. Asking them to attend traditional English classes after a full school day is a hard sell.
The solution is not better textbooks. It is context.
When English is embedded into activities children already enjoy, learning happens naturally. Sports, theater, coding, cooking, robotics. English becomes the working language rather than the subject.
I am personally building a soccer based English program, but the model extends far beyond football. Italy is deeply oriented around group activities and shared experiences. Programs that respect that cultural reality see strong demand and high retention.
The upside is recurring participation and long term trust with families. The risk is execution. Instructor quality is everything, and reputation travels fast. This is a hands on business, but when done properly, it is resilient.
Bureaucracy and life administration as a service
Italian bureaucracy is not inefficient by accident. It is the product of layered systems, local autonomy, and decades of incremental rules. For locals, this is normal. For outsiders and time constrained professionals, it is overwhelming.
Simple tasks often involve multiple offices, conflicting information, outdated digital tools, and mandatory in person appointments. People do not want help filling out forms. They want the problem resolved.
A service that takes full ownership of administrative tasks creates immediate value. Utility activation, residency registration, healthcare enrollment, fines, address changes, school paperwork. The emotional relief alone is significant.
The upside is consistent demand and strong referrals. The challenge lies in complexity. Every comune operates differently, processes change without notice, and solutions require local knowledge. Businesses that succeed here are built on relationships and reliability, not automation alone.
Succession and modernization of family owned businesses
Italy is filled with profitable small and mid sized businesses facing an uncertain future.
Many are run by founders or owners in their sixties and seventies. Digital presence is minimal or nonexistent. Processes live in the owner’s head. Succession plans are unclear, and younger generations often live abroad or pursue different careers.
This creates opportunity for entrepreneurs who are patient and culturally aware.
Modernizing operations, professionalizing processes, improving storytelling, and supporting generational transitions can preserve real value while creating sustainable businesses. This is not about flipping companies. It is about continuity and respect.
The upside is access to real assets with existing cash flow. The risk is trust. Relationships take time to build, and progress must be gradual.
Stepping back, Italy is not an easy place to build, and it is full of inefficiencies. But that is precisely why opportunity exists here. For entrepreneurs willing to observe carefully, move patiently, and work within the grain of the culture rather than against it, Italy rewards depth over speed and substance over spectacle. In bocca al lupo to all of you!




