Business and Civic Affairs
In 1592, Leonard expanded his business interests by becoming a member of the Levant Company. In 1594, he was one of fourteen members of the Merchant Taylors Company who each pledged money to support an indigent widow through one of the company's charitable schemes.
He entered local government, as an alderman, in 1594, and was also one of the city's sheriffs for 1595-96.
In September 1599, he and 124 other merchants formed 'The Governor and Merchants of the City of London Trading to the East Indies', otherwise known as the East India Company. It was chartered on 31 December 1600. While membership was open to the public (known as 'the generality'), executive control was restricted to the merchant élite, and Leonard was not only one of the original 'committees' (i.e. directors) but also joint treasurer from 1600 until 1602.
The EIC's first two trading expeditions to India were profitable and earned investors a healthy return, as well as supplying the merchants with imported merchandise to re-sell at profit. Leonard invested £1000 – the largest individual stake – in the first voyage.
Leonard was knighted by King James I on 26 July 1603. He was one of 906 men knighted by the new king during the first four months of his reign.
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