Caitlin Crosby and The Giving Keys

“It’s our duty as humans to keep an eye out for each other and take care of each other when we’re weak and broken,” Caitlin Crosby says as she sits across from me in The Giving Keys office and workshop in Downtown Los Angeles. A musician, actress and entrepreneur, Caitlin lives by this idea in all her work; in fact, it’s the driving force behind it.

“The Giving Keys didn’t stem from a business plan, it stemmed from, I believe, just genuine compassion for people,” she tells me. The story is unique, because when Caitlin set out to help people, she took her time until it was right. She had been promoting the message of her website,, in her tour merch, and went into a locksmith’s one day to have the phrase engraved on a key that was around her neck. Eventually she got engraving tools, started selling similar keys at shows, and people couldn’t get enough of them. Instead of just turning this into a profitable business, Caitlin thought she could the keys could be a project that could help people, but didn’t quite know what it was yet.

One day she came across a homeless couple on the street, and wanting to help, she took them out for dinner. When the girl, Sarah, said that she made jewelry to sell on the street, things just came together for Caitlin. She asked the couple to be her business partners, got tools and materials and The Giving Keys was in business, soon selling at stores like Fred Segal. While the business blossomed, partnering with organizations like The United Way and Chrysalis and hiring homeless people to make keys, it became a vehicle for employees to transition out of homelessness.

The idea behind the keys is simple: each has a word engraved on it, such as “hope” or “strength”. They are meant to be paid forward, so that keys pass from person to person, wherever their message is needed. More inspiring, however, is the idea that lives are being changed for the better with each key, by the act of making them, and thus every aspect of the process is a form of paying it forward. Caitlin says, “Eleven or twelve people who are trying to transition out of homelessness are employees, and then so far five of them have gotten off the street from engraving the keys and are working in our office, doing production work.”

The Giving Keys is not a non-profit, however. As Caitlin told me, “Non-profits are great, but I didn’t just want to give handouts and not solve the foundational, fundamental issues. I wanted to create jobs, which create hope in these people’s lives.” As I watch her interact with the staff around the office, it is immediately clear that she takes a deep personal interest in everyone there. It is inherently part of her personality to care about every person she comes across. “I really believe in second and third and fourth chances,” she says, “and a lot of times it’s impossible, literally impossible, for some of these people to get jobs elsewhere because of their past… I think there’s a lot of gold inside of these people and they just need somebody to come along and encourage them and give them hope because there’s real gold in them. But if they’re sleeping on the streets and getting passed by every day with their dignity feeling challenged or degraded, I think it’s hard. I think that gold just gets covered up and wasted and it breaks my heart.”

What is unique about Caitlin is not only her passion and personal investment in working to improve the lives of others, but her business savvy and entrepreneurial spirit. She didn’t feel right about selling the keys to raise money and donate it to a cause, and even though it took six months, she waited until the idea that was right formed in her head. In an incredibly short amount of time she’s not only helped a lot of people – both in providing opportunities and giving a positive message – but has established a space for people in need to find much-needed and life altering help. She has founded an entire community based around compassion and made it profitable.

Women Working to Do Good is a series that Hello Giggles and the White House have been collaborating on. We will bring you stories of women in communities across the United States who we think are stars in their own right. Whether they are young entrepreneurs, active community organizers, or making a difference in a single life or community, we think these women are amazing and want to share their stories with you! Each story will also be featured on the White House blog, and we are working together to bring more strong female role models to the forefront.

Photo by Julia Gazdag