Despite slavery-era statutes that outlawed black literacy, he learned to read and write as a child with the help of Sampson, his father. When slavery ended, Love's parents stayed on the Love plantation as sharecroppers, attempting to raise tobacco and corn on about 20 acres, but Sampson died shortly after the second crop was planted. Afterward, Nat took a second job working on a local farm to help make ends meet. At about this time, he was noted as having a gift for breaking horses. After some time of working extra odd jobs in the area, he won a horse in a raffle on two occasions, which he then sold back to the owner for $50 each time. He used the money to leave town, and at the age of 16, headed to the Western United States.
After driving a herd of cattle to the rail head in Deadwood, Dakota Territory, he claimed to have entered a rodeo on the 4th of July in 1876, enticed by the $200 prize money. The only difficulty with this story is that Deadwood newspapers, which covered every event of the Fourth of July celebrations, make no mention of a rodeo that day. He claimed to have won the rope, throw, tie, bridle, saddle, and bronco riding contests. It was at this rodeo that he claims friends and fans gave him the nickname "Deadwood Dick," a reference to a literary character created by Edward Lytton Wheeler, a dime novelist of the day.
Love left the cowboy life before he married a woman named Alice in 1889 and settled down. They lived in Denver, Colorado initially. He took a job in 1890 as a Pullman porter, which involved overseeing sleeping cars on the Denver and Rio Grande Railroad. While working for the railroad, he and his family resided in several western states, before finally moving to southern California.
"Mounted on my horse my ... lariat near my hand, and my trusty guns in my belt ... I felt like I could defy the world."
In October 1877, Nat Love wrote that he was captured by a band of Pima Indians while rounding up stray cattle near the Gila River in Arizona. Although he claimed to have received over 14 bullet wounds in his career (with "several" received in his fight with the Native Americans while trying to avoid capture), Love wrote that his life was spared because the Indians respected his heritage, a large portion of the band themselves being of mixed blood. He almost married the chief's daughter. The band of Native Americans nursed him back to health, wishing to adopt him into the tribe. Eventually, Love writes, he stole a pony and escaped into West Texas.