La Bocca Ristorante & Vineria is a well-known Italian restaurant in White Plains. Now owned jointly by financial consultant and entrepreneur, Alessandro Crocco, and his wife, AnnaMaria – who recently bought the restaurant from her father, founder Tony Spiritos – La Bocca features an intimate dining room, private event space and a selective calendar of culinary and cultural programming.
Recently, the Westfair Business Journal spoke with Alessandro to discover how he balances his various activities – and if he has any tips on how to run a family business (without coming to blows):
Alessandro, AnnaMaria is from a restaurant background, but did you yourself have experience in hospitality before you both met?
“Yes, hospitality has been part of my life for as long as I can remember. I had the unfair advantage of growing up with a mother who was an exceptional chef. She taught me early that food is not just nourishment; it’s culture, care and identity. Later, I studied food and beverage management at Cornell, which gave me a strong operational foundation – costing, service standards, systems and what it takes to build something that’s both excellent and sustainable. By the time AnnaMaria and I met, I already had meaningful exposure to restaurant operations and the discipline behind running a real hospitality business.”
The two of you are the new owners of La Bocca. How has that altered the financial structure or your independence?
“In many ways, this is a renewal. I stepped away from the restaurant’s day-to-day operations in 2019, and I’ve recently come back fully engaged alongside AnnaMaria. The purchase from her father formalizes a transition that’s both financial and personal. It gives us a clearer ownership structure, the ability to invest confidently and the independence to shape the next era of La Bocca Ristorante & Vineria with intention.”
In simple terms, what are the benefits – or pitfalls – of buying an ongoing business from a parent or family member?
“The biggest benefit is continuity, protecting a legacy that already has trust in the community. You inherit more than a business; you inherit relationships, reputation and a culture, and that can be a powerful foundation to build on. The pitfalls are often emotional and operational.”
You have several other business interests and enterprises on the go locally. Can you share what some of those are?
“Yes, beyond La Bocca, I’m an investor and operator across a few different industries. Some people would call it being a serial entrepreneur, but I try to keep everything connected by one guiding idea: Success isn’t measured only in dollars, but in freedom, purpose and the ability to build things that matter. Since 2019, I’ve been very involved in the financial world. I’m also the founder and CEO of the Hortus Foundation, where I lead major cultural heritage initiatives, including a multiyear restoration campaign supported by international donors and institutional partners.
On the for-profit side, I invest in and build ventures focused on cross-border growth between Italy and the United States. And I’m active in the wine industry through my importing platform, VentunoVino, where we serve customers across more than 17 states.”
How have you renovated the restaurant and event space and how do you gauge return on investment (ROI)?
“We renovated with two goals – improve the guest experience and strengthen the business model. We upgraded key areas of the dining room, improved ambiance and comfort and elevated the private events space so it’s truly functional for corporate dinners, celebrations and curated experiences. ROI isn’t only about spending to grow in today’s market. Some upgrades are also about protecting your position, staying relevant and meeting guest expectations.”
It’s restaurant lore that establishments only make “real” money over the sale of wine and liquor. Does this still hold true, and how do you address declining alcohol consumption?
“Wine and beverage still matter a lot to restaurant economics, especially when thoughtfully curated and paired with food. That said, consumer behavior is changing. People are more health-conscious, drinking less and choosing quality over quantity. Our response is to make the beverage program more intentional and more accessible – more by-the-glass options that feel exciting but approachable, curated pairings and flights and a focus on value and storytelling regions, producers and styles. We also host monthly wine dinners that spotlight different regions of Italy, while also celebrating some of the greatest American wines.”
Please tell us about La Bocca’s new Italy Unboxed initiative. What is it exactly?
“Italy Unboxed is a culinary and cultural initiative designed to “unbox” the real Italy, beyond clichés. It’s about immersive experiences through food, wine and storytelling: curated tastings, regional menus, collaborations and events that connect guests to Italy’s true diversity and traditions. It’s one of the projects I’m most excited about, because it combines education, hospitality and culture in a way that feels authentic and joyful.”
La Bocca emphasizes “authentic Italian cuisine,” but Italy has 20 regions. What does authentic really mean?
“Authentic doesn’t mean one fixed style; it means truthful to origins. Italy is not one cuisine; it’s many. Authentic means respecting ingredients, technique, balance and the spirit of regional cooking, while also understanding where you are and who you are serving. (But), of course, you’ll see a special emphasis on Calabria, my home region, through dishes like fusilli calabresi or cozze alla calabrese, often featuring spicy ’nduja and other ingredients that bring that Southern Italian character to life.”
Lastly, are there any plans afoot for other La Bocca restaurants, or are you content right now?
“Right now, our focus is to build La Bocca into the strongest version of itself, especially after the renovations and ownership transition. We’re investing in consistency, service, private events and unique experiences like Italy Unboxed. That said, I’m entrepreneurial by nature. If expansion makes sense, it would be done thoughtfully and without compromising quality. The priority is to protect the standard and the culture of what we’ve built, because that’s what makes it special.”
