He had five brothers; James (1765–1819), George (1766–1838), Edward (1768–1852), Francis William (Frank) (1774–1865), Charles John (1779–1852), and two younger sisters, Cassandra and Jane.

His female cousins admired his flattery and he grew to be his father's favourite son, who was also adored by younger sister Jane.

His father recognised his scholarly abilities and made sure that he and his older brother, James, were privately tutored; they took lessons in Greek and Latin.

Henry spent an important amount of time with both Eliza and his brother James, during which they grew, both socially and personally, through theatre.

While they did not participate directly being too young to act, Henry's sisters Jane and Cassandra were often observers and helpers with the theatrical activities.

[7] Shortly after resigning from the militia, during the period of time that the Treaty of Amiens was in effect, Henry and his wife returned to France in an attempt to reclaim Eliza's assets.

He stayed at John's College in pursuit of an MA, working as an Assistant Logic Reader and teaching undergraduates, until 1793 when war broke out between England and France.

In 1795, during his time as paymaster, Henry had the opportunity to serve under the order of Lieutenant Cornwallis in protecting Ireland from the French for seven months.

Here, Henry made several connections with other rich and powerful figures whose influence contributed to his interest in pursuing a banking career.

[19] During his time as the Oxfords’ paymaster, Henry had earned the respect of his colonel, William Gore-Langton, who, in 1801, enabled Austen to begin his career as a financial agent by providing him with work for the Oxfordshire Regiment.

As an agent, Austen primarily worked as a middleman between the government agency responsible for releasing military wages and the regiment's paymaster.

However, there were several other ways Austen made profits: He collected the pay per company of a fictitious "warrant man," he worked as some officers’ private banker, as a half-pay agent, and participated in some buying and selling of commissions.

[21] The peace following the Treaty of Amiens in March 1802 made it difficult for Austen to continue profiting as much as he had previously from military finance.

Thus, he and his wife Eliza travelled to France, where they shipped wine to well-off acquaintances back in England as an expensive commodity.

James was the brother of John Henry Tilson, a Lieutenant-Colonel of the Oxfordshire Regiment, and had also previously been a partner in the Dorset & Co. Bank of New Bond Street.

[25] Austen, Maunde & Tilson lasted until its bankruptcy in 1816, which came about due to several overlapping causes, including Henry's ill health, some poor choices of investment, the general depression following the war, and the closing of many country banks.

Henry was known to gossip to his upper-class circle of friends and acquaintances about her novels in order to promote them and help her rise to fame.