In about 1896 he arrived at Fremantle, Western Australia where he worked for a tinsmith.
He developed an interest in labour issues with a strong belief in nationalist policies as well as becoming a prominent advocate against conscription.
At 6 feet 4 inches (1.93 m) he was confident and charismatic and developed strong debating skills.
He was secretary of the Western Australian Football League from 1905 to 1914 and in 1905 established the Young Australia Football League.
The same year together with Lionel Boas, the YAFL was renamed to become the Young Australia League which aimed to promote healthy outdoor activities for Western Australian youth, particularly boys.
The organisation flourished for many years and expanded to other states.
Simons was referred to by YAL members as "Boss Simons".
He was secretary of the Western Australian State School Teachers Union until 1917 and was State president of the Australian Natives' Association in 1910-11.
He was secretary of the Western Australian Trotting Association in 1913-14, later being made a life member.