From age 23 to 25 there are records of him sailing as an able-bodied seaman on multiple trips between Saint John and Liverpool and London.

Thompson, Idaho, Daisy Ainsworth[3], Rainier[4], and Emma Hayward..[5] Captain Holland's half-brother, Phillip, was with him in Oregon and also involved in shipping.

Unfortunately, he was mortally injured in a collision between the steam launch Mikado and an Oregon and California Railroad ferry on October 26, 1886.

In December 1889 he employed a gang of men to remove stumps and level the site on Shilshole Avenue before ship building could begin.

[5] His Ballard ship yard also repaired vessels including Henry Bailey,[12] Josephine,[13] Fanny Lake,[14] Wasco,[15] Mabel,[16] Detroit,[17] and State of Washington.

Holland, sailed north on July 6, 1892 on Alice Blanchard, with a crew of builders from his shipyard, parts for the new steamer, and Portus B. Weare, an executive of the company for whom the ship was named.