In 1764, Henry Skaggs led his first expedition through the Cumberland Gap, a mountain pass at the junction of Kentucky, Tennessee and Virginia. These early trips westward attracted the interest of famed explorer Daniel Boone. Boone used his existing relationship with North Carolina land speculator Richard Henderson to recruit Skaggs as an agent for Henderson's land company, Richard Henderson and Company. In 1765, Skaggs explored the lower Cumberland River region (upper Middle Tennessee) as an agent of Henderson and established his station near the present day Goodlettsville, Tennessee.