In September 2004, Our Hearts to Your Soles was founded by Matthew Conti, a high school student at the time, with the help of his father Dr. Stephen Conti, an orthopaedic surgeon in Pittsburgh, PA. After volunteering for the summer at a local hospital and seeing the problems that can be caused by improper footwear, Matt decided to start a non-profit organization that provides free medical foot screening examinations and shoes to the less fortunate people of the metropolitan Pittsburgh area. Because other programs provided clothing but not shoes to the homeless population, he saw a great need for their organization.

On February 24, 2006, Our Hearts to Your Soles launched its first event and was able to shoe approximately fifty homeless men at the Light of Life Ministries in the City of Pittsburgh. Those fifty men said that we made their night, and each thanked us with a "God Bless You." Some walked in wearing a size 9 but needed a size 12 shoe. Blisters and callouses covered their feet. We learned that a kind word and a simple pair of shoes can go a long way.

In 2007, Our Hearts to Your Soles took its cause nationally, and the entire Conti family including Chris and Laura joined in. The organization's outreach was expanded to include an event the week before Thanksgiving, which involved 35 sites in as many states. To accomplish this we partnered with Red Wing Shoes, who continues to provide thousands of pairs of shoes to Our Hearts to Your Soles each year.