Over the years, Whitehead was able to keep the interest of several young assistants who worked for no remuneration because they were fascinated by his projects. Pruckner, Harworthy, Bert and Andy Papp and Louis Lazay were a few of the young boys who put up with Whitehead's eccentric but creative ways. The longest standing assistant was Junius Harworth. All of the assistants contacted years after the fact claimed that they learned much from Whitehead that helped them to obtain good employment as adults. Junius Harworth went on to become a foreman at the Packard Company Motor Plant. Without the help of these interested boys and their efforts to keep up and get along with the tempermental inventor, Whitehead would never have been able to complete his historic projects.
In addition to the boys who helped to make his dream a reality, Whitehead also had help from other influential people.
Over a period of the years between 1901 and 1903, his younger brother John Whitehead joined him and provided both physical and financial assistance. Unfortunately, a falling out between them terminated their working relationship and John moved with his family to Eagle Bay, BC becoming one of the first families in that region to homestead.
Another notable assistant came in the form of Stanley Beach, son of the editor of Scientific American and himself the aviation editor of his father's magazine, giving both advice and financial assistance, though the level is unknown.
In addition to these sources of fund, Whitehead used some of the traditional methods of raising money such as taking contracts for work that he would never complete on time (or at all). He had poor financial skills and kept no proper books. He would construct engines or motors for others with no knowledge as to whether he had actually made money or lost by the end of the project.
Stella Randolph writes about one of Whitehead's disappointed customers, a balloonist named Captain H.E. Honeywell who stated,
"I gave him (Whitehead) an order for two light specially constructed motors for aeronautical purposes according to his ads and claims. After months of waiting and much corresponding, also many checks on account, finally made a trip to Bridgeport, Connecticut, to find them abandoned under his work bench; he could not make them work."
Other investors complained about sinking money into projects where no profits were realized. Whitehead never patented any of his projects (due to significant lack of funds and organization) and so could never realize them to any commercial potential.
Many accounts of Whitehead pose him as putting every last cent into his inventions. What money he earned from his variety of jobs or contracts went straight into his dreams.