He went on to establish the Portland Belt Line Company, which lobbied city officials to extend the cable car system to St. Johns, Oregon.

When he turned 18, McKenna had enough formal and informal education to ascertain a job at a rural Ohio public school.

[1] From there, McKenna was self-taught, taking odd jobs on farms and railroads until at 18 he was hired to educate at a public school in Ohio.

[1] McKenna served as the board's first chairman and in his first annual address, laid out a plan to attract manufacturing plants to the city.

[3] McKenna advocated for public control of the cable car, saying the city should construct the line and either contract the operation out or run it themselves.

[3] In 1903, McKenna secured a double-track electric streetcar line to the peninsula with the Portland Railway Company.

[4] In 1889, McKenna moved to Portland, Oregon, and invested in a large amount of land, the majority of which was in the University Park neighborhood.

His first newspaper advertisement appeared in 1890 where he was noted as the manager of the Conservative Real Estate & Trust Company.

[8] In 1910, McKenna purchased 1,280 acres of land for US$12,800 in a rural area near Chitwood, Oregon, where he established a ranch.

[14] Early in his land development career, McKenna devoted portions of his advertising to his personal opinions on politics and civic matters.

His first opinion was published in his ad which appeared in the edition of April 2, 1893, of The Oregonian which stated his opposition to a miller regulation bill.

[17] An early example of this was when McKenna worked for Dr. C. C. Stratton, then-president of Portland University, who advocated for Oregon to have an open immigration stance.