He was described as generous, hospitable, a 'big man with a ponderous overhang of waistfront, a trim, grey beard, the curling moustachios of a cuirassier, and brown, kindly eyes gleaming through his spectacles'.
The family emigrated to Australia in 1854 or 1855, drawn by the potential for riches from the Victorian goldrush, but Macleod's father died a year later.
Anderson's heavy drinking and the family's parlous financial state forced Macleod to find work at the age of 12.
His studies led to the production of a number of paintings and stained glass designs, and by the age of 17 Macleod was earning enough from commissions to purchase a home for his mother, away from her husband.
Months after The Bulletin was launched, he and another artist, Samuel Begg, purchased a third share of the magazine, but relinquished it when the founders, J. F. Archibald and John Haynes were more financially secure.
When he was approaching the end of this work, J. F. Archibald, who had been impressed by his business methods when a contributor to the Bulletin, asked him to join the staff.
In 1901, known as 'Mr Bulletin McLeod', he was the toastmaster at the send-off dinner at the Hotel Australia to Scottish Border poet and Australian bush balladeer Will H. Ogilvie (1869–1963).