3 Powerful Lessons for Aspiring Social Entrepreneurs

Interview with Caitlin Crosby

Episode Description

Imagine you see a homeless couple on the side of the road holding a sign that says “Ugly, Broke, and Hungry.”

You stop to hear their story and take them out to dinner.

And before the last course is served, you’ve invited them to be your business partners.

That’s the story of Caitlin Crosby, the founder and creative visionary behind the company The Giving Keys.

The Giving Keys employs people who are trying to transition out of homelessness to engrave keys with different inspiring words. You buy a key and wear it for awhile, and then you look for your chance to pass it on and pay it forward to somebody you feel needs the message on that key more than you do.

Grab a box of tissues and check out this video to meet the people they serve:

Caitlin’s story is remarkable for so many reasons, not the least of which is that she never set out to be a social entrepreneur. She’s a musical artist and actress. But her company is thriving and making a real impact in Los Angeles, so I invited her to join me on the Building a StoryBrand podcast to help us understand what has powered her success.

If you’re a creative person or visionary running a business or believe in the power of entrepreneurship to make a difference in the causes we care about, don’t miss this inspiring interview.


Understand Your Own Strengths

Tell me if this sounds familiar. Your vision as an entrepreneur has finally turned into a reality. It’s working, and you’re plugging away every day. Your organization is scaling up quickly, and you’re doing whatever you have to do to keep up. One day, you realize you’re miserable and operating completely outside of your skill set and natural gifting.

How do you get your sanity back and find your sweet spot again?

I asked Caitlin about this, because she’s an artist and creative who found herself knee-deep in Excel spreadsheets trying to run a business. For her, bringing on the right people made all the difference. A business consultant helped her see this, saying, “Instead of you talking to every single person and managing all of the issues, have one person on the team who can filter all of those things and you can just talk to them.”

That person, Brit, grew into the role of President, managing the day-to-day aspects of the business and giving Caitlin the space to recharge creatively and lead the company through her charisma and ideas.

It’s a lot like the visionary-operator relationship that David McKeown discusses in this podcast episode, where we talk about the hires you need to scale a business successfully.

Keep the Cause First

The whole concept of social entrepreneurship has gained a ton of traction in the last decade, with names like TOMS Shoes and Seventh Generation leading the way.

As a result, a lot of business see it as a trend to latch on to. They might give a percentage of proceeds toward this or that or partner with a local nonprofit. And that’s not at all a bad thing.

But as Caitlin points out, what’s made The Giving Keys so successful is the authenticity of the mission, and that’s critical to successful social entrepreneurship.

“It has to come from caring about the cause first,” Caitlin says. “People are trying to become social entrepreneurs, but they’re kind of doing it backwards and I think that [customers] can smell that it’s not real and authentic when you’re just trying to make a buck or make a new trendy thing.”

When Caitlin took that homeless couple out to dinner, it wasn’t because she was trying to find a great marketing angle for her company. She cared about filling their bellies and hearing their stories. That kind of authenticity is irresistible. It makes people want to come alongside your cause and be a part of it.

Remember the “Why” of What You’re Doing

Whether you’re a social entrepreneur or a traditional one, you’ll face this struggle if you haven’t already.

As you scale up, it’s easy to lose sight of what drives you. Your business can eclipse your mission, or your family, or your health. I asked Caitlin how she keeps the “why” in what she’s doing.

“I think this is such a good question for anything that you do in life,” she replied. “Sometimes you just get to feeling numb. It’s so hard sometimes when you find success that it really is not the thing that’s going to bring you happiness and fulfillment.”

For Caitlin, that numbness can come when she spends too much time in the management and nitty-gritty details of the business. For her to stay energized, she has to stay connected to the authentic human stories of the people she works with. It’s how it all started, after all.

“I just spend that time with those individuals where it’s just about that human connection,” she says. “That is the thing that just keeps me going 100 percent. If I didn’t have that, I couldn’t keep doing what I’m doing at all.”

For you, it may be a completely different source of renewal. But staying close to what inspires you will give you the energy and creativity to dig into every other part of your business.

No matter your role as a leader, Caitlin’s story is such a powerful reminder of how much impact our work can have on the world. We’ve got to lean into the stories of others and “keep our antennas up,” as Ernie Johnson would say, for how we can serve those around us.

What keeps you connected to the “why” of leading or running your business? Leave a comment and share.

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Executive producer: Tim Schurrer
Additional production and editing: Chad Snavely

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