In 1996, at around 18–19 years of age, Jack first encountered Grandmaster Wan Kam Leung at the Ving Tsun Athletic Association in Prince Edward, Hong Kong. At the time, Grandmaster Wan was in his early fifties, while Jack was a young martial artist in his competitive prime—having achieved success in Karate tournaments and trained extensively in Jook Lum Southern Praying Mantis. Like many young practitioners at that stage, he carried a strong sense of confidence in his ability and understanding of martial arts.

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During their first interaction and training exchange, Jack was immediately introduced to a level of skill that challenged his assumptions about martial ability. Despite the significant age difference, and despite Jack’s youth, strength, and competitive background, he found himself effortlessly controlled and unbalanced through simple, direct movements. What appeared subtle and relaxed from Grandmaster Wan was, in practice, completely overwhelming in structure, timing, and precision.

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This experience left a lasting impression on him. It became a defining moment in his martial arts journey—shifting his understanding from strength-based expression to the principles of structure, economy of motion, and efficiency under pressure. It marked the beginning of his commitment to studying Wing Chun under Grandmaster Wan Kam Leung.

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During his early Wing Chun development, Jack continued training both Karate and Wing Chun simultaneously. During this period, he participated in a sparring session against his Karate Sensei's son—a grown, physically strong and well-built black belt adult, and one of the more experienced fighters in the club. At the time, Jack was still a young adult with only a short period of Wing Chun training behind him.

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Despite the clear physical disadvantage, Jack was able to apply the principles he had begun learning in Wing Chun, redirecting force and controlling the exchange more efficiently than expected. This experience further reinforced his growing understanding that effective self-defence is not determined by size or strength, but by structure, timing, and the ability to remain composed under pressure, developed through consistent sensitivity training such as Chi Sau (sticky hands).
 

Shortly after this period, he made the decision to fully dedicate himself to Kung Fu, recognising that true self-defence lies in the ability to remain functional against stronger opponents. For him, the essence of martial arts became simple: the ability to go home safely, and to protect and care for those he is responsible for.
 

He continued his training directly under Grandmaster Wan Kam Leung in Hong Kong, progressing through the system and completing the Wooden Dummy level before relocating to Australia for further studies.

Despite the distance, he maintained a close relationship with his Sifu and regularly travelled between Australia and Hong Kong for continued training at the Jordan school.

While studying in Australia, Jack faced a practical challenge—he was unable to find a similar Wing Chun lineage school in Queensland that aligned with his training path. During this period, due to academic, work, and life commitments, he temporarily stepped away from formal training. When he later explained this situation to his Sifu, he expected disappointment.
 

Instead, his Sifu encouraged him to continue training in martial arts in whatever form was available, even if it was not Wing Chun. He advised Jack to explore other systems, remain active, and broaden his understanding rather than remain inactive waiting for the “perfect” training environment. This perspective deeply influenced Jack, revealing the open-mindedness and depth of his Sifu’s teaching philosophy, and further shaping his respect for the principles behind the art rather than attachment to form alone.

“A martial artist should never rest his training. One should always keep the Kung Fu spirit alive.”
 

Inspired by these words, Jack resumed training—expanding his experience into Chow Gar Tong Long (Southern Praying Mantis) and other lineages to broaden his understanding of Kung Fu principles.

In 2008, he developed an interest in strength and conditioning for combat and began training in Muay Thai and Krabi Krabong, travelling regularly to Thailand over several years to deepen his skills.