A closed door that threw a career wide open

Arianna Alessi is Managing Director of Red Circle Investments, CEO of Brave Wine, and Vice President of the OTB Foundation, the charitable arm of the OTB Group. But behind those titles is the story of someone who found the courage to forge a career for herself, after she was denied a position in the family business. “I was born in Bassano del Grappa into an entrepreneurial family of goldsmiths,” she says. “After graduating in Economics and Business Law from Bocconi University, the first granddaughter to do so, I couldn’t wait to make my contribution to the company, but unfortunately I hit a wall. My grandfather and my uncles (but not my father), with their patriarchal mentality, decided to entrust the fate of the company only to the sons and grandsons.”

That door was closed; she needed to go elsewhere to find work. So Alessi joined an investment bank in Milan, working on M&As and immediately diving into international finance. “One closed door allowed me to become the professional I am today, with a wide range of skills in both the corporate and legal fields, having also worked in prestigious international law firms. Today I can say that not joining the family business was a very lucky thing for me!”

Breaking into the world of finance brought new challenges. “I remember being the only woman on the M&A team and often finding myself alone during coffee breaks. There were all men with a great passion for soccer, specifically for Inter Milan. I found the key to bridging the distance: to becoming an Inter fan. The rest was all about the preparation and expertise I acquired over time,” she adds.

During those years, Alessi worked on important mergers and acquisitions and specialized in economic and financial consultancy, first in another firm and then on her own.

Her personal and professional lives intertwined when she met Renzo Rosso, founder of Diesel and chairman of the OTB fashion group, who later became her husband and the father of her baby girl.

Since 2018, she has served as Managing Director of Red Circle Investments, Rosso’s private investment company, which focuses on various high-tech sectors. “We invest in companies that aim for innovation and sustainability, such as the food industry B Corps Cortilia and Planet Farms. We choose companies whose values and vision we share,” she says. Red Circle Investments has around thirty direct and indirect shareholdings and participation in funds. “Our way of doing things is to influence the future,” she adds.

But Alessi’s range of action goes beyond the for-profit sector. She works in tandem in the non-profit sector with her OTB Foundation. As she tells is: “It was Renzo who asked me to take the reins of the Foundation, which today implements and supports social development projects in critical areas, from Ukraine to Africa. The Foundation is active in four main areas: children and youth, women’s empowerment, integration, and emergencies. I had never worked in the third sector before, but I tried to bring my financial expertise to this new world.” Each project presented to the Foundation is evaluated quantitatively and qualitatively, as if it were an investment opportunity in a for-profit company. The idea is to have an impact on people’s lives, but also to create sustainable, enduring initiatives.

Gender equality is also a key issue for the OTB Group. “Among other things, the OTB Foundation supports women’s empowerment projects, including one that provides scholarships to prestigious universities for deserving girls with financial difficulties. In selecting beneficiaries, we look for a strong motivation to make a difference in society, whether in public administration or in business management. Knowing that we are helping even one person a day makes our world a better place.”