July 17, 1948 – November 2, 2022

Alan E. Lewis

Social entrepreneur, business builder, and lifelong advocate for changing people’s lives.

Alan Lewis traveling abroad
Alan E. Lewis grew up in some of Boston’s toughest neighborhoods, moving fourteen times before the age of seven. He understood early how uneven life’s playing field could be, and learned just as quickly how to break the rules, challenge convention, and take roads others wouldn’t.

Those experiences shaped the instincts of an entrepreneur and the convictions of someone who would become an unwavering champion for the underdog. The same qualities that would later define the companies, communities, and causes he built.
In 1983, he founded Kensington Investment Company as the home for the Lewis Family's real estate, investments, and philanthropic work, built around a single idea: capital and conviction are most powerful when aligned.

Two years later, he and Harriet bought a defunct travel company called Grand Circle and turned it into an $800 million global enterprise operating in 85 countries. To Alan, none of it was just "the business." As his children Edward and Charlotte put it: he was in the business of changing people's lives.
“Go to action, make mistakes, learn, iterate, go to action again.” 
ALAN E. LEWIS

“Get comfortable being uncomfortable.” 

Kensington, New Hampshire remained Alan’s true north throughout his life — the place where his maternal family had roots dating back to the 1600s, and where he spent the summers of his childhood. Years later, he and Harriet returned to build Alnoba : a 600-acre landscape of trails, sculpture, conservation land, gathering spaces, and leadership experiences designed to inspire reflection, courage, and human connection.

More than a retreat center, Alnoba became a physical expression of the values that shaped Alan’s life and work: leadership, stewardship, curiosity, community, and the belief that people are capable of far more than they imagine.Since 1981, the family’s philanthropic work has supported organizations across more than 70 countries through initiatives focused on leadership development, environmental stewardship, youth empowerment, education, and humanitarian aid.

Today, those efforts continue through the Lewis Family Foundation, the Grand Circle Foundation, Pinnacle Leadership and Team Development, and the Farm at Eastman’s Corner.

Alan Lewis hiking outdoors
The Lewis family, 2019

“Strong leaders make stronger communities.”

Alan believed leadership wasn’t a title. It was a practice — available to anyone willing to take responsibility, step forward, and do the work. Strong leaders, he often said, were the single greatest force for change in any company or community.

In 1993, he founded Pinnacle Leadership and Team Development, which has since trained nonprofit and business leaders from more than 60 countries. He didn’t teach leadership from theory. He taught from lived experience; leading companies through the Gulf War, September 11th, the 2008 financial crisis, and the COVID-19 pandemic. Those lessons later informed his book, Leading Through Turbulence, and the principles he became known for during moments of uncertainty: tell the truth, move quickly, empower leaders, and keep going.

In 2018, Alan and Harriet launched the Alnoba Leadership Awards to honor individuals advancing environmental and social justice through courageous action and meaningful impact. Following Alan’s passing, the organization renamed its highest honor the Alan E. Lewis Moral Courage in Leadership Award.

Above all else, Alan was devoted to his family, to Harriet, to their children Edward and Charlotte, and to his granddaughters. The values he built KIC around, courage, stewardship, generosity, leadership, and belief in human potential, continue to shape the company today.

The Story of Alan E. Lewis
“You can dream and you can dare.”

Fearless, unconventional, demanding, and deeply generous, Alan E. Lewis built companies, communities, and leadership movements around a simple belief: people are capable of far more than they think. This documentary explores the philosophy, intensity, and humanity behind the man who challenged others to dream bigger, move faster, and lead courageously.