Tommy Caldwell began climbing at a young age, under the tutelage of his father. He grew up in Loveland, Colorado, but often visited Yosemite National Park in California to climb. This place would become even more special to him as he advanced in his career. At age 16, he entered his first international competition as an unknown amateur, and won. This marked the beginning of his career and was only the first of his many accomplishments to come.

As an up-and-coming star in the climbing world, Tommy was invited to participate in a unique climbing trip to Kyrgystan. There, he, along with three other climbers in his group were held hostage by rebels for six days. He speaks about this situation as one of the most life-changing experiences he has ever had.

Not too long after his return from his time in Krygystan he faced yet another challenge. In 2001, he accidentally sawed off most of his left index finger, and the doctors were unable to successfully reattach it to the point where it was functioning. However, instead of ending his career, it pushed him to learn to climb in a different way. He continued on to make some of the hardest climbs in history.