Leaving Boston for Milan: Lessons from My 20-Year Journey

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Successful entrepreneurship and innovation require a deep understanding of target customers’ needs, wants, and goals. Traditionally, gaining these insights has been time-consuming and resource-intensive, but the emergence of artificial intelligence is changing the game. By leveraging AI tools, entrepreneurs can now analyze customer data at scale, extract valuable insights, and make data-driven decisions.

I’m an entrepreneurship professor at Babson College, where I teach future-focused courses on AI and entrepreneurship and lead our AI lab. While some in business believe AI is overhyped, the unfolding AI age will be a revolution for entrepreneurs — and my students — aiming to explore, understand, and seize business opportunities.

AI can accelerate human creativity and inquisitiveness, helping entrepreneurs unearth insights about what customers want and value. My research, industry work, and teaching at the nexus of AI and innovation show that AI capabilities will only grow in importance. Here’s why.

Tapping into AI’s Superpowers to Scale Insights

One of AI’s superpowers is synthesizing vast amounts of data and empathizing with customers more deeply — quickly.

Tools like Otter.ai can transcribe focus group sessions or customer interviews within seconds, allowing entrepreneurs to rapidly identify unmet needs, pain points, and value-creators. Sentiment analysis APIs like those offered by Microsoft Azure can detect emotional cues and tones in customer conversations that humans might miss. By aggregating these data over time, entrepreneurs can get a deeper understanding of how customers feel about their brand, product, or service. That’s insight at scale.

AI also can help entrepreneurs tap into the voice of the customer at scale. Customer feedback from various sources such as social media, product reviews, and customer support tickets can be automatically collected and analyzed using tools like MeaningCloud. By setting up automated workflows using platforms like Zapier, entrepreneurs can streamline the process of gathering and analyzing customer feedback, enabling them to identify recurring issues and opportunities for improvement and innovation.

AI also can assist in rapidly iterating on value propositions, such as for a website or important presentations to customers. Tools like Claude can help entrepreneurs quickly generate variations of their messaging based on customer feedback. These variations can then be fed into platforms like Copy.ai to create compelling product descriptions that resonate with a target audience. By continuously refining their messaging based on customer input, entrepreneurs can arrive at a winning value proposition much more efficiently.

Customizing the Customer Experience

Real-world examples demonstrate the power of AI in understanding and engaging customers. One of my top undergraduate students at Babson, Chloe Samaha, founded BOND, a virtual water cooler app for remote and hybrid teams. The app’s core purpose is to support culture-building, employee satisfaction, and worker retention among distributed teams.

Her company uses the latest version of OpenAI’s ChatGPT to generate personalized, culture-specific daily questions — answered by all — that drive engagement and retention among employees. By analyzing engagement data, BOND continuously refines its AI model to deliver engaging content tailored to each company. Without ChatGPT, this level of customization would be impossible at scale. The results speak for themselves: BOND has facilitated over 20 million moments of connection between colleagues and achieved an impressive 300% year-over-year revenue growth, highlighting AI’s potential to customize experiences that resonate with users and drive business success. BOND gets and seizes upon the insight-generation capabilities of AI.

As AI continues to evolve, its potential applications for entrepreneurship are boundless, particularly for the rapid prototyping of entrepreneurial ideas. ChaptGPT’s ever-improving ability to support text-to-code enables non-coders to prototype their software ideas simply by describing them to an AI. And those who already know how to code can now do so five to 10 times faster.

In our AI lab at Babson, we’re designing new approaches to prototyping where students can 3D print a new product concept “extracted” from a 2D text-to-image model, such as OpenAI’s Dall-E or Midjourney. Soon enough, I expect, students will only need to describe a prototype they wish to create, and AI tools will help rapidly embody those ideas in a voice-to-prototype experience.

The barriers between the digital and physical world are dissolving, and we’re entering an era of AI-augmented creativity that will both accelerate innovation and democratize entrepreneurship. I see the advances, quarter by quarter, across all areas of AI.

To stay ahead of the curve, entrepreneurs must embrace AI as a tool for understanding their customers more thoroughly. By leveraging the right AI tools and platforms, entrepreneurs can gain deep insights into customer needs, preferences, and sentiment. Armed with this knowledge, they can make data-driven decisions, iterate more quickly and ultimately build products and services that truly resonate with their customers. The future belongs to entrepreneurs who can harness the power of AI to build customer-centric businesses.


Leaving Boston for Milan: Lessons from My 20-Year Journey

From Beantown to Milan: Embracing Change and Growth

Twenty years ago, at the age of 35, I left my comfortable life in the Boston suburbs to pursue a job opportunity in Milan, Italy. My journey from Boston to Milan has been filled with challenges, growth, and invaluable lessons. Here’s what I’ve learned along the way.

Seizing Opportunities and Embracing Change

I first came to Italy through an exchange program with Bocconi University’s business school while earning my MBA. This experience, along with an internship at Pirelli, set the stage for my future in Milan. When Pirelli offered me a full-time position in marketing and communications, I didn’t hesitate. Despite knowing only a few people, I was excited about the new opportunity and eager to embrace the change.

Navigating the Complexities of Italian Bureaucracy

One of the first challenges I faced was navigating the complexities of Italian bureaucracy. Getting a tax number, an ID card, and a work permit involved numerous visits to City Hall and long waits. My advice for anyone moving to Italy is to go with the flow. The system can be frustrating and complex, but it’s important not to sweat the small stuff. Embrace the quirks and take things in stride.

Determination and Networking: Keys to Success

Five years into my Italy adventure, Pirelli sold their telecoms division, and I was laid off. With only a year left on my residence work permit, I was determined to find a new job. Networking was crucial. I reached out to former colleagues, headhunters, and business school alumni. Eventually, I secured a position with a U.S. multinational with offices in Italy. This experience taught me the importance of strategic networking and staying determined, even in the face of setbacks.

Adapting to a New Work Culture

Adapting to a new work culture was another significant challenge. One of the best things I did was to let go of the mindset, “This is how we do things.” I embraced change and learned to work differently. Whether it was using a new language or navigating corporate life, adapting to my new environment was essential. It took me about two years to feel comfortable with Italian, but the effort paid off. I learned valuable insights about my peers and the business over meals and coffee breaks, which I wouldn’t have gained with my head down at my desk.

Financial Adjustments and Planning

Moving to Italy also required financial adjustments. Beyond typical expenses like rent and utilities, I faced unexpected costs, such as getting a driver’s license, which cost me close to 700 euros. Additionally, Americans are taxed based on citizenship, not residency, so I had to report my taxes in both the U.S. and Italy. Using an accountant helped me navigate these complexities. Despite paying higher taxes in Italy, I benefited from the public healthcare system and supplementary private health insurance, which allowed me to allocate more money towards other needs and leisure activities.

Living a Fulfilled Life

Ultimately, stepping out of my comfort zone 20 years ago was one of the best decisions I made. I’ve had the opportunity to travel extensively, meet wonderful people, and build a fulfilling life and career in Milan. The experience has taught me the importance of embracing change, staying determined, and adapting to new environments.

Key Takeaways for Aspiring Expats

  • Go with the Flow: Embrace the complexities of the local bureaucracy and don’t sweat the small stuff.
  • Be Determined: Network strategically and stay persistent, even in the face of setbacks.
  • Adapt to New Cultures: Let go of old mindsets and embrace the new work culture and environment.
  • Plan Financially: Be prepared for unexpected expenses and plan your finances accordingly.
  • Seek Fulfillment: Step out of your comfort zone to find opportunities for growth and fulfillment.

Moving from Boston to Milan has been an incredible journey, filled with lessons and growth. For anyone considering a similar move, I hope my experiences provide valuable insights and inspiration. Embrace the adventure and the opportunities that come with it, and you’ll find a fulfilling and rewarding life abroad.


Learn more:

  1. Otter.ai
  2. Microsoft Azure
  3. MeaningCloud
  4. Zapier
  5. Copy.ai

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