Leadership Breakfast with Lain Shakespeare

On Tuesday, August 30, the Center for Civic Innovation hosted Lain Shakespeare for a Leadership Breakfast, our monthly event series humanizing Atlanta leadership. Lain is one of the most community-oriented ATLiens we know.

Coming from a family with deep Atlanta connections, Lain grew up in Decatur. With family members including Joel Chandler Harris, noted folklorist behind the collection of Uncle Remus stories, and Julian LaRose Harris, journalist, Lain spent his formative years here in Atlanta, but wanted to see something different as an adult. He moved away for college, but after spending a few years in cold northern winters, came back to Atlanta, determined to know his home city better.

When he came back to Atlanta shortly after college, he didn’t know what he wanted to do. He hadn’t had a singular life goal. One thing he quickly learned, though, was that the Wren’s Nest, his family legacy, was in dire need of help. So at 23, Lain took the reins and became the Executive Director of the Wren’s Nest.

This historical house museum and literary center in Atlanta’s West End was in such dire straits at the time that, on Lain’s second day, Georgia Power came by to turn the power off. Blessed with the gift of gab like many of his ancestors, Lain talked his way into a little more time to pay that bill and to build a sustainable future for the Wren’s Nest.

This period at the Wren’s Nest was staff-driven because many other stakeholders hadn’t figured out how to get involved yet. “They handed me the keys to the car, but I didn’t have my license yet, or even my permit!” Lain reflected. He mentioned that, while inexperience is often seen as a detriment, he believes his worked to his - and his organization’s - advantage. Because he didn’t know differently, he wasn’t scared to jump right in and try a new idea. For example, he began the Wren’s Nest individual donor list by going through his high school yearbooks. 

In addition to the financial struggles, there were cultural challenges he had to address. He found himself at the helm of running an institution in the heart of one of Atlanta’s historically black neighborhoods preserving the work of a white man from the South in the 1880s who had preserved African American folk art. Lain described his great great grandfather’s role in this preservation work as important for African American communities, but really done “for white audiences.”

If you’re saying you’re an organization preserving African American folklore, you can’t be an exclusive organization.
— Lain Shakespeare

Continuing to change the culture of the Wren’s Nest into one that interacted with the surrounding community in a more authentic, respectful way was a significant part of Lain’s mission. He never shies away from unpacking a complicated situation and loves the idea of the beginner’s mind, using that newness to plow forward where other people might have gotten too jaded to move forward with the work.

I always like to lead with who you are, not what you know, because, when you lead with what you know, it’s automatically a condescending conversation.
— Lain Shakespeare

TED talks on his mind, facilitator Rohit Malhotra, Executive Director of the Center for Civic Innovation, brought up Chimamanda Adichie’s TED talk, “The Power of a Single Story”, asking if it was a paradigm that spoke to Lain in his work at the Wren’s Nest or currently in his role at Mailchimp. Lain said yes, the power of stories was so important to them that they instituted classes working with kids who lived near the Wren’s Nest in the West End to do exactly that, capture the power of single stories. 

Narrative is everything.
— Lain Shakespeare

On his journey to Mailchimp, Lain mentioned that he always knew his time at the Wren’s Nest would be limited. He wanted to make sure they didn’t slip into being a personality-driven organization, dependent on one person’s leadership, instead of community-driven. So after five years at its helm, he left the Wren’s Nest.

He still didn’t have one set life plan for himself, but had always enjoyed online projects and one day found himself chatting with a friend working at Mailchimp. His friend was tasked with hiring a nonprofit liaison and encouraging Lain to apply. Lain came on board as Mailchimp’s nonprofit liaison and was lucky enough to have a solid year to learn about corporations, Mailchimp’s products, and his own work style, something he didn’t have a lot of time for in his previous position. His first position at Mailchimp was to advocate for nonprofits as Mailchimp developed and improved their products; he was a brand manager. He also mentioned that being in LEAD Atlanta during this transitional time provided a lot of support and helped him bridge corporate and civic connections.

Lain’s transition to his current role at Mailchimp was somewhat serendipitous. One day, Mailchimp’s CEO Ben Chestnut called Lain into his office. He was frustrated with the way the tech world was tossing around the word “community.” He charged Lain with coming up with a definition of “community” that Mailchimp would use to guide their philanthropic efforts. They came up with a vision to:

  • Help stop cycles of poverty,

  • Support artistic excellence, and

  • Encourage more considerate urbanism (making Atlanta work for people first, not cars).

These foci are what guide Mailchimp’s community involvement and philanthropy today.

One of the Mailchimp projects Lain is proudest of is bike self-repair stands. A Mailchimp executive had seen examples of these very accessible repair stands in train stations in European cities and asked Lain if they were something Atlanta might like. Lain knew they could be useful here. Mailchimp could have afforded to buy bike repair stands; they could have been a gift to the city. But Lain didn’t want to bring that kind of mindset to Mailchimp’s community work or this project. The Atlanta Bicycle Coalition (ABC) was already looking at installing these repair stands. ABC ran a crowdfunding campaign to fund seven “fix it” stands. They were successful, and Mailchimp matched every dollar they raised. Lain is most proud of this project because of how the community drove the project.

Want to know more about Mailchimp’s community work? Check out their investor report