Chapter One — Beginnings
Fueled by water, paint, and the open road.
"Maximize what you have."
He got in the water at five. He picked up a paintbrush at six. Sixty countries later, Gregory still swims and paints.
At one year old, three months after moving to Jerusalem, Gregory contracted polio. He has never walked without leg braces and crutches — so his arms have carried him up mountain trails, through IronMan finish lines, across marathon courses and into studios where Chinese painting masters work the way they have for a thousand years. The disability is a fact but has never been the center of gravity. Instead, it served as a catalyst.
No one handed him a ceiling. That absence — not being told what wasn't possible — is the single most significant factor in everything that followed. The stories we hear about what is possible becomes the story we live. He knows this firsthand.
Chapter Two — The Athlete
Three Games. Five Medals. Five World Records.
Gregory competed at three Paralympic Games and came home with five medals — two gold and a silver from Atlanta 1996, a silver and bronze from Barcelona 1992. During his 27-year swimming career he set five world records. On the way to those medals he trained alone in Hong Kong, working two full-time jobs, with no institutional support and no certainty of selection. Just the pool, the alarm clock, and the decision to show up.
The athlete in him is not a chapter that closed — it is the frame through which he understands commitment, output, and what happens when the outcome is uncertain. In 1984, he finished the Honolulu Marathon in sixteen hours, dead last. Between 2006 and 2012, he completed four Half-IronMan triathlons and one full IronMan. These are not credentials. They are evidence of a discipline — the one that now runs beneath every keynote or workshop he delivers.
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 moved to Taiwan after declining an offer to work for the Peace Corps in Morocco. He studied Chinese painting and calligraphy with local masters and learned Mandarin. The bold, gestural visual language that would later appear in boardroom-scale commissions for the IOC and the LA28 Olympic Committee was formed in those studios — in Taipei, not in any formal art academy.
Before any of that, he had made a 16-month solo overland journey through China, Tibet, Nepal, India, and Pakistan — with a backpack and on crutches, without an itinerary or reservation. He has spent a lot of his life going before he knew exactly where he was going. It has served him well.
Jade Mountain, Taiwan · 1987 · 4,000 metres
PepsiCo Restaurants International HQ, Hong Kong 1994
Chapter Four — The Pivot
Hong Kong, a KFC sponsorship, and a Barcelona swimming pool
By 1992, Gregory was in Hong Kong — training for the Barcelona Paralympic Games while working two full-time jobs with no sponsor and no safety net. KFC came in. He went to Barcelona, won a silver and a bronze, and came home to a job offer with the Colonel. He took it. After two jobs and full-time swim training, one job felt almost leisurely.
He stayed five years. What the pool and the studio hadn't taught him, corporate life did. He transitioned from backpack to business class and learned how organizations and executives think. Then in 1998, the Asian Economic Crisis hit. At 40, he was out of a job. He calls it the best bad thing that ever happened to him.
Five years inside a global brand had given him the fluency to craft his stories and workshops around the needs of different audiences. Now at 40, he returned to the work he'd been building toward since his first figure drawing classes at university.
