Career
After the war, he worked as an agent for the Buckeye Oil Company in Ohio from January to July 1865, purchasing equipment and contracting laborers to work in the oil fields. In October 1865, he and friends paid $30,000 for five thousand acres (20 km²) of cotton-farming land in Georgia. This failed philanthropic adventure left him more than $10,000 in debt. Reluctantly at first, out of desperation, he started on January 1, 1868, as a clerk and later became a junior partner in his father’s business, Lee, Higginson & Co., which at the time was a modest brokerage. His father had been a junior partner until 1858 and worked until his death in 1889 at age 85. This brokerage and banking company eventually became very profitable. Henry Lee Higginson was eventually a senior partner.
In 1913, he offered this assessment of changes in business over the course of his career: "There has been a steady improvement in the management of the Stock Exchange since I came down to the financial district. The methods in use to-day are very much better than they were many years ago. Men dealing with the Exchange are better protected." He allowed that there were still "rascals" and "a good many men who still need watching," but "not so many as there have been in years past."
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