Chan Wa Soon was Yip Man's first teacher. Unfortunately Chan Wa Soon died at a young age and Yip Man did not finish his instruction. As a young man, Yip Man studied English at the St. Steven's Catholic School in Hong Kong. It was during this time that Yip Man met Leung Bik who was the son of Leung Jon. Yip Man challenged Leung Bik and was beaten. When Yip Man found out who Leung Bik was, Yip Man asked to become one of Leung Bik's students. Leung Bik, being a small man, did not use muscles. His style was not as hard as that of Chan Wa Soon. Yip Man was able to learn both the hard and soft elements. (Another story from this time tells how Leung Bik's daughter-in-law was able to defeat Yip Man with her skill in Wing Chun kicking. From that time Yip Man never said he was number one in Wing Chun as long as the others were alive).

After Yip Man's schooling in Hong Kong, he went back to China, his home town, worked as a policeman and trained cops in China. While working as a policeman, Yip Man killed someone in the line of duty. Fearing reprisals from the Communist government, he had to escape China and lost all his possessions. When he got to Hong Kong he only had his skills in Wing Chun with which to make a living.
In Hong Kong Yip Man met his old time best friend Chung Choui (Go Dai Chung). Go Dai Chung was a Hung Sang Choy Lay Fut teacher and taught through the Chinese Restaurant Association - East and West. Teaching at both locales was too much for Go Dai Chung and he gave one to Yip Man which is located at Dai Lum Gai in Kowloon, Hong Kong so he could teach Wing Chun to make his living.
Leung Sheung was a bookkeeper for the Chinese Restaurant Association and an assistant teacher to Go Dai Chung. Leung Sheung challenged Yip Man and was defeated. Leung Sheung thereupon became Yip Man's first student. Other early students included Lau Ming, Lau Kau and Lee Yu. Yip Man is known as the person who brought Wing Chun out of China and into Hong Kong, however, there were certain types of students that Yip Man would not teach. Yip Man felt that relatives would not show him the respect that he deserved. Even though Wing Chun was developed by two women, Yip Man felt that having women in a gung-fu school would be too disruptive.