At first an assistant to his father, he studied law and soon achieved a reputation by the brilliance of his mind and the magnetism of his personality.

As presiding Judge at Hillsborough he had come into conflict with the violent element among the Regulators, who had driven him from the court and burned his house and barns.

For some time prior to his elevation to the bench, he had been engaged in land speculations.

One of Boone's biographers suggests that Boone may have been secretly acting as Henderson's agent during his first lonely explorations of Kentucky.

However this may be, it does not appear that Boone and his Yadkin neighbors were acting with Henderson when in September, 1773, they made their first attempt to enter Kentucky as settlers.
Richard Henderson had known Daniel Boone on the Yadkin; and it was Boone's detailed reports of the marvelous richness and beauty of Kentucky which had inspired him to formulate his gigantic scheme and had enabled him also to win to his support several men of prominence in the Back Country.