Bailey Richardson: Building Communities that Get Together and Stay Together

Bailey Richardson grew up with a foundational belief “that you can make any future you want.” This “naive optimism,” as she calls it, led her to the startup world, where, in her early 20s, she became one of the first dozen employees at Instagram and worked closely with Prokit co-founder, David Swain.
After leaving Instagram, Bailey started People & Company with Kai Elmer Sotto and Kevin Huynh to “help people bring their people together.” It would be challenging to find someone who thinks more about the meaning of community and the magic that goes into building it than Bailey and her co-founders. They’ve interviewed thousands of community organizers, advised startups and leading brands, and written the community-building playbook, Get Together.
We’re all pros at something. Bailey is a pro at community. Her insights won’t disappoint. Here’s the community kit.
Listen to our podcast with Bailey Richardson on The Common Threads: Apple Podcasts | Google Podcasts | Spotify.
Listen to the Podcast
David Swain, Prokit: What did you have for breakfast?
Bailey Richardson: I was away surfing in North Carolina and South Carolina for the last few weeks, and when I came home, I found out that my refrigerator had broken, which is a disgusting experience. Because I can’t keep anything in the house, I need to go out more than I normally would. This morning, I got coffee and a power berry smoothie from Food U Desire, a great bodega on Smith Street in Boerum Hill, Brooklyn.
What was your childhood like and were there indications you would become the community builder you are today?
Two words stick out when I remember who I was at 11 or 12: competitive and optimistic. Both traits were passed down to me from my mom and dad. I’ve always been competitive with myself. I played every sport growing up. Sports make me happy. I played basketball, volleyball, and softball. My dad was a semi-professional barefoot waterskier growing up, so I water skied.  My uncle surfed Mavericks, so I surfed. My mom was a competitive swimmer, so I swam. One of my uncles was a collegiate football player, and my dad’s identical twin was an Olympic bobsledder, so sports are big in my family. Sports was an outlet for my ambition and a way to push myself. I was also really driven in school. I’ve had to dial it back as I age and want to be a more chill, happy person.
Then there’s the optimistic side. I grew up in the Bay Area, near San Jose and Santa Cruz. My dad is an optimistic engineer. He believes we’re going to solve all the problems the world has and that you can figure out anyt...