Chapter One — Beginnings
Fueled by water, paint, and the open road.
"Maximize what you have."
Gregory got in the water at five. He picked up a paintbrush at six. Neither has let him go since — and he has never wanted them to. Swimming and painting are not chapters in his biography. They are the constants that have run beneath every other chapter: the Paralympic pool, the studio in China, the residency in the Maldives, the canvas propped against a wall in a Moroccan Riad.
At age one, living in Jerusalem, Gregory contracted polio. He has never walked. He ambulates with his arms — and those arms have taken him to over sixty countries, up mountain trails, across marathon courses on crutches, through IronMan finish lines, and into the studios of Chinese masters in Taiwan. The condition was never the point. The movement always was.
His first job, at fifteen, was making milkshakes at McDonald's in Holland, where his family lived while his father worked at the US Embassy there. It was not an auspicious beginning. It was a perfectly fine one.
That absence of a ceiling — never being told what he couldn't do — may be the most significant factor in everything that followed. It is the thing Gregory now most wants parents of children with disabilities to hear: the story you tell a child about what is possible for them becomes the story they live.
What shaped Gregory was not adversity — it was curiosity. The kind fed by open water and open roads. Traveling made the world his subject matter — not as a tourist passing through, but as someone searching: for sanctuaries, for ancient sacred sites and geological wonders, for the places where human wisdom seems to have settled quietly into the landscape itself.
Over sixty countries and several decades, he found them. What he absorbed along the way — in temple complexes at first light, on mountain trails, in communities that live close to the land and close to the bone — became the raw material for both his paintings and his keynotes. Not his own story as the subject. The world as the lens.
Chapter Two — The Athlete
Three Games. Five Medals. Five World Records.
"One step at a time is the only method that has ever moved anyone from where they are to where they want to be."
3
Paralympic Games
5
Medals: 2 Gold · 2 Silver · 1 Bronze
5
World Records in Swimming
16 hrs
Honolulu Marathon on crutches, 1984
5
Ironman events
Gregory competed at the highest level of Paralympic sport across three Games. He returned with two gold medals, two silver, and one bronze — and set five world records in swimming. He carried the experience of elite competition into every room he has spoken in since. The physical discipline was total. The mental discipline was harder to describe — and more transferable.
In 1984, he completed the Honolulu Full Marathon on crutches in sixteen hours — coming in dead last. Between 2006 and 2012 he competed in four Half-IronMan triathlons in Singapore and one full IronMan in Korea — swimming, cycling on a handcycle, and crossing the finish line in a wheelchair.
What the athletic career gave Gregory was not trophies. It gave him a precise understanding of the relationship between commitment and result — the knowledge that consistent forward motion, without certainty of outcome, is the only reliable strategy for covering impossible distances.
That understanding is now the backbone of every keynote he delivers.
USA Paralympic Relay Team · Atlanta 1996
With President Bill Clinton · The White House · 2000
Chapter Three — Going East
Taiwan. China. Tibet. Nepal. India. Pakistan.
"Going without knowing all the answers."
At 24, Gregory slipped into the fabric of Asia — moving to Taiwan with no contract, no plan, and no guarantee of income. What he had was a decision: he would study Chinese painting and calligraphy from the ground up, learning from local masters. He studied the language alongside the art — brushwork, ink, the carving of stone chops, the mounting of Chinese scroll paintings, Chinese art history at the Palace Museum and the discipline of a tradition that had been refining itself for over five thousand years.
He stayed long enough to be changed by it. His visual language, the one that would eventually appear in boardroom-scale commissions for the IOC and multi-national corporations, was formed in that period — in Taiwan, in those studios, with those teachers.
The sixteen-month solo overland journey — China, Tibet, Nepal, India, Pakistan — was not a gap year. It was a graduate education in the one subject no university teaches: how to keep moving when you are alone and do not know where you should go next. The conditions were not comfortable. The logistics, for a person who ambulates by arm power alone, were formidable. The rewards were unrepeatable.
In 1991, at 33, he joined the ten-person film crew of the Return of Marco Polo — what followed was a year sailing from Tahiti to China, making two dozen television documentaries for the series The Return of Marco Polo, arriving eventually in Hong Kong where Gregory left the ship. It was not the obvious next step. That was the point.
Jade Mountain, Taiwan · 1987 · 4,000 metres
Chapter Four — The Pivot
Hong Kong, a KFC sponsorship, and a Barcelona swimming pool
"After two jobs and full-time swim training, one job felt almost leisurely."
By early 1992, Gregory was in Hong Kong — working two full-time jobs simultaneously and training alone for the Barcelona Paralympic Games, covering costs with no institutional support and no certainty of selection. Just the pool, the work, and the discipline.
KFC, then part of PepsiCo Restaurants International, came in as a sponsor. Gregory went to Barcelona, competed, and returned to Hong Kong with a silver and a bronze medal. KFC offered him a job. He took it. After two jobs and full-time swim training, one job felt almost leisurely. After winning at the Paralympics, it was also at this time that Gregory began his career as a keynote speaker.
He stayed with KFC for exactly five years — long enough to learn what the pool and the studio never taught him: how organizations think, what keeps people stuck, and what actually moves them. He absorbed commercial logic from the inside. It would serve him on every stage he ever stood on.
In 1997, the Asian Economic Crisis swept through the region. Gregory, at 40, was let go. He calls it the best thing that ever happened to him. Five years of corporate life had given him the fluency to walk into any boardroom as an equal. But it had kept him one step away from the work he'd been building toward since those childhood sketches of comic book characters and his first figure drawing class at Franklin & Marshall College. Now there was nothing else to prove. It was time to embrace the artist who'd been playing second fiddle for too long.
At 40, with no salary and no safety net, he began again. One step at a time.
