The Giving Keys was founded by Caitlin Crosby in 2009. Crosby was a singer and entertainer and always had a heart for supporting women who dealt with body image issues. She originally started an organization called Love Your Flawz with Brie Larson. This organization consisted of people taking pictures with a hand written sign that embraced their flaws. Later in 2009, Crosby was inspired by a key that was given to her at a hotel. She wore the key around her neck as a way to remember it and wrote “Love Your Flawz” on it. Crosby then made multiple keys that had inspirational words and sayings on them and began to sell them. The keys symbolized how everyone is unique and flawed, but still play a major role in society. Crosby originally sold the keys at her concerts, telling her fans to “pay it forward”. The keys began to outsell her own albums, but she knew something about the keys was missing. This is when she had the idea to employ homeless people as key engravers. In 2010, Caitlin Crosby renamed the brand The Giving Keys and started a website for people to place orders on and easily buy the product. In 2011, Crosby partnered with Path to find employees for her business.

Caitlin Crosby constantly shifted her entrepreneurial goals. Originally, she was an entertainer, then the founder of Love Your Flawz, and finally she was the owner of The Giving Keys. Crosby always pivoted her ideas until she found the perfect cause for her to support. She always had a heart for giving back, but her focus for that shifted over time. She began supporting women who deal with image issues and ended by employing homeless people. The heart of her cause never changed, despite finding more factors to focus on. The keys still share the same message as Love Your Flawz, but she found another cause she could support at the same time. Crosby’s entrepreneurial spirit was focused on pivoting until the perfect idea was created. Now, through The Giving Keys, 144,719 hours of work has been created for people transitioning out of homelessness.