Bailey Richardson: Building Communities that Get Together and Stay Together

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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 ThreadsApple Podcasts | Google Podcasts | Spotify.


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 anything you want to do. I think some of that comes from his ability to build anything he wants. He can completely rebuild cars, set up solar panels, build me anything I want. He has this optimism about realizing things that are unrealized. My mom was one of the first female pilots for United Airlines. She started by loading luggage at San Jose airport, and she worked her way up to be a pilot and a captain. There’s something I’ve absorbed from my parents’ belief that you can make any future you want, despite adversity. 

I think some of that naive optimism led me to want to work in startups. I wanted my hands close to the biggest challenges and the biggest problems, and didn’t want to work my way up gradually at a company. The Bay Area itself has this optimism around creating a new website, a new project, or a new tool and being able to quickly affect the world with it. So I think those two childhood characteristics really led me down the path I went down. 

How to Build a Community

At 25-years-old, you were explaining the power of the Instagram community to the biggest newsrooms and organizations in the world. Talk about what the word community means to you. 

Since I left Instagram, I’ve interviewed hundreds of communities, from run clubs in New York City to a cloud appreciation society to Twitch streamers followed by big communities. During all those conversations, I noticed that for people over the age of, say 50, or people who don’t work in technology, the word “community” means their town or their neighborhood. It’s very physically correlated. Part of the reason why we need a definition of community today is that the internet has changed who we can meet and connect with on such a foundational, powerful level. The word “community” is changing. 

Bailey Richardson of People & Company speaking at a conference

I like to break down the components of a true community. A community is a group of people who keep coming together over something that they care about. There are three components to that, the first one being the group of people.

There was a trend that may still exist where businesses in particular use the word community for an audience or an entire user base. It’s sort of an euphemism, a language bend trick. When we work with companies or with individuals, we try to get them to be much more specific on their who. Who is in their community? Community is not a generic euphemism. It’s a label for a specific group of people who are passionate and active in a cause and a purpose

The second component is that people need to keep coming together. In tech language, that means they’re retained. I would see people throw a one-off marketing event and call it a community event, but they weren’t seeing the same folks continually show up for each other. It’s okay if you have an audience, and it’s okay if you have a marketing event, but a community is a different thing. It’s a group of people who show up for each other over and over again. 

The final component is the thing that the people care about. There needs to be a passion point, some connective tissue that activates all of these people to want to connect with each other. It could be skill development, emotional support, accountability, or fun. That’s where some of the magic shows up. Every community has a slightly different expression of exactly what brings them together, and depending on what that thread is, the shape of the community will be different. Those are the three key components of what we define as a community versus another kind of group. 

The biggest thing we have learned, and I do feel like this was at the center of the way we worked at Instagram with our early users, is that you build a community with people, not for them. It’s a progressive act of collaboration. As an original host, or as a founder, you host the first party, make the website, or do the first posts on a slack group. Then your job is to bring as many people as possible into co-ownership of that space, to give away roles and responsibilities, and to do more together than you could alone by building with others. I find that that orientation, at least in businesses, is a bit foreign to people. There’s a lot of history of businesses seeking control of the quality of their product, control of their brand.

I was so young at Instagram, and didn’t know any different. We saw these passionate users who were raising their hand to help us translate the app, to host Insta meets, and who were doing an incredibly thoughtful job with their content. I felt like we could just break our company and our brand into little pieces, pass it around, and let users speak for us. We let the passionate people in the community organize for us, instead of us talking at people as a monolithic brand. I loved working that way. The reason that I, along with Kevin and Kai, run People & Company is because I prefer to work more collaboratively. Maybe it comes from my experience on teams, but I prefer empowering people over trying to control, or funnel, them. I love collaborating with passionate people. It makes me feel alive and that that was something I wanted to learn more about and do more of after I left Instagram.

Traditionally, a company wants to control the message. Instagram basically flipped that upside down. Their mindset was data-informed, not data driven. Talk about how that worked for the company. 

First, I want to say that Josh Riedel, the first employee hired at Instagram, led the community team, and much of what happened at Instagram started with his and Kevin’s vision. We hired Pamela Chen, an amazing National Geographic journalist, to take over editorial as we were leaving, and she shared this quote that really stuck with me: “Not everything that counts can be counted, and not everything that can be counted, counts.” There are things that are valuable to invest in that you cannot measure effectively, and not all of your data is actually insightful. I think it’s a balancing act. 

Bailey Richardson and Josh Riedel at Instagram
Bailey and Josh Riedel with a special friend

For core vision and innovation, data isn’t the right information for all companies. For iteration, and improvements, data is extremely valuable. Data tells you the what; it doesn’t tell you the why. Instagram was good at having principled points of view about things that were outside of the purview of data and more about human psychology. 

People called Instagram’s launch the most successful launch of any product in the history of Silicon Valley. I haven’t lived long enough or paid close enough attention to say if that’s true or false, but immediately people were using the product when it went public. Some of that has to do with the way that Kevin and Mike did early outreach, and some of it has to do with their thoughtfulness of creating a foundation of users on the platform. 

Our job as a community team was to educate new users. The product grew before it was fully-baked. It was extremely simple in the beginning, and we had all sorts of people joining. When you’re a new user, you don’t know what to do. You have to be taught what to do. We didn’t have an unlimited staff of engineers to make the perfect onboarding flow, or perfect recommendations for who to follow. Instagram was so new, if you signed up somewhere like Korea, maybe none of your friends would be on it. Our job as a team was to educate new users and existing users about what was possible on Instagram and what you could do to contribute in a meaningful, well-received way. 

In 2010 in the U.S., what existed online socially for people was Twitter and Facebook. There was no sense of artistry or creativity on those platforms. Flickr had existed before, but it had already slowed down. In terms of the quality and perspective of the photos, the content on Instagram was better. On Facebook, people were posting pictures of their friends before they went out to a college party. On Instagram, you could see someone’s favorite place to eat or an incredible place they’d taken a hike. There was fresh, different content. 

Our job was to show new users the other people on the platform that they could learn from, people who could inspire them to understand how to get value out of this platform and how to participate in it. With any creative endeavor, humans look at something someone has done, and they remix it and make it their own. That’s how we grow, learn, and expand ourselves creatively. 

If I may share one thing from what we knew at Instagram in the early days, it’s this: If you’re starting a digital space, role model the behavior that you want to see there. Role model with good content from existing users, so that when people show up, they can learn from that and replicate it. That isn’t necessarily something that data is going to tell you to do, but it’s a key insight. It’s one that was absolutely a differentiating factor for Instagram.

It’s easy to look at any company today and forget the steps that it took to get there. What are the mistakes people make when starting to focus on building a community? 

I think about it like this: what it takes to build a boat is different than what it takes to sail the ship. Knowing what phase of a business you’re in and what your most important investments are at that moment is, in many ways, the great skills of a leader. I have my own critiques of Facebook, but I do think that Mark Zuckerberg is one of the best leaders I’ve seen in terms of getting a company to adjust to the phase of the world that it’s in and to shift to the current demands. 

Two types of people come to People & Company. We see big companies making a new innovative investment, either to supercharge a group of extremely passionate customers or to open a new investment, like a new program or a new digital space. We also get a lot of founders.

I find almost universally that people want to talk about the version of their business that is five years down the line. They want to think on a strategic level of a mature business. They almost disbelieve that you have to do step one to get the momentum going for a community, which can be on a really small scale. 

For example, Weight Watchers is one of my favorite stories of a company. They’re huge. Before COVID, they were having 30,000 in-person meetings a week around the world. It all started with one meeting led by Jean Nidetch, a housewife from Queens who had figured out a diet that worked for her from the New York State diet department. She had a secret meeting with six other people in her apartment. That first step of coalition building eventually led to the company going public and global within a few years. So sometimes it starts with literally six people in a room, a Medium post, or a bunch of emails.

I interviewed a seasoned founder, Courtland Allen, for our podcast, Get Together. What struck me about him was his capacity to understand what needs to happen at what phase of a business. He knows when to do high-touch things and when it makes sense to stop doing them. He went through Y Combinator and realized after founding a venture-backed company that he didn’t want to do that again –he wanted to be independent. Courtland started to look for inspiration from other independent founders, people who hadn’t taken on VC money, and he couldn’t find any stories about them. He decided to build a company for people who are independent entrepreneurs in the process of trying to figure out how to be an independent entrepreneur. There was a gap that people need more guidance and more support. 

Bailey Richardson and her co-hosts for the Get Together podcast

To get this product started, Courtland explained to me that he researched 150 different independent entrepreneurs. He spent three days without sleeping, finding this list of names, and writing them extremely personal, thoughtful emails. His emails recognized them personally and asked them to contribute to the community by being interviewed. Now there are 60,000 different independent entrepreneurs in this forum. Once he got the machine going, Courtland automated a lot of it and built systems and processes that allowed many of the high-touch elements to be low-touch. But he says in those early days, there’s no cheat code for personal outreach. There’s no cheat code for building momentum. 

Spending three days of our lives writing 150 emails, or hosting a meetup for 25 people, doesn’t seem worth the investment compared to where we’re trying to be in five years, but if you skip step one, you can’t get to step five. You have to do it. It’s hard when you’re a founder who has worked at a big multinational company because the numbers look so different when you’re starting from scratch. Laura Nestler, of Duolingo and Yelp, says that community building is like the inversion of the marketing funnel. I believe that. Instead of starting with a ton of people and moving them through a funnel, you start with a small number of passionate people and you build out from there.

Whether you’re an early-stage founder or an established company, giving ownership to the people in the community is hard. What’s the best approach to recognizing who the right people are? 

There are three steps: pinpointing, vetting and supercharging. First, you pinpoint your hand raisers, the most passionate people. You want people who are genuine and qualified. Depending on what you want their help with, whether it’s opening a chapter community or being someone you feature on your blog, you want to make sure that they are passionate about the purpose that your community is pushing forward. 

That is how we chose who to feature on the Instagram blog. We would see if people were just trying to get more followers or if they were truly passionate about meeting new people and connecting with other human beings. I would crawl through Instagram and look for interesting photographers. I would check if they had replied to people who left comments on their photos before I would feature them. 

The next step is vetting. You want to make sure the people are qualified. We spoke to a woman who started Queer Soup Night, for example. It’s a very simple format. A queer cook creates a soup and throws a party with suggested donations. All the money gets funneled to a local activism group. They were only in New York for a long time. When they started opening up new chapters, they realized that they needed chapter leads with experience in cooking, as well as chapter leads who had experience with putting on parties. Those were the two qualifications. You need people with the combination of passion and qualifications. 

From there, you try to supercharge the efforts that they’re working towards. Let’s go back to Queer Soup Night. The people who are opening up chapters might need help marketing their events or hosting the events. The job of the original leader in New York has now transformed into figuring out different assets and tools that she can offer to her chapter leads.  

Another example of supercharging your leaders is creating an ambassador role. This works for an organization, not a chapter. We had “suggested users” at Instagram. eBay also created an ambassador role in the early days. They took community members who were successful at selling, and they would supercharge those people by giving them the opportunity to share their knowledge. Some sellers would have podcasts or be featured at meetups. You need to think about how you can amplify the work that these passionate people do and make it easier for them to do the challenging parts. Then their core work can be even more impactful. 

If you can do that in a structure that’s scalable, you can reach many more people than you could as a small startup team. Instagram in the early days was 12, mostly all white, under the age of 30, people in San Francisco. We knew we needed leaders in other countries where people were using Instagram and where people had interests that we didn’t have. For example, there’s a level of authenticity that someone in Japan who’s really into coffee could have when speaking to other people in Japan who are into coffee than we could never have. It can be a really powerful strategy to scale energy and scale momentum. If instead of doing it all yourself, you say, “How can I work with people to do this for even more people?”

Choosing the Right Community-Building Tools

There are so many avenues to start creating a community – email, Facebook groups, in-person gatherings, when possible. If you don’t have your own platform, where do you put your focus? What tools work best?

Identifying passionate people is definitely a big challenge of community building. I realized it was easier for me at Instagram because we owned the platform. It can be hard to do this work if you don’t have data signals built into your software that allow you to identify who is engaged and coming back again and again. 

We had to get scrappy at Instagram in the early days. I would use API partners at the time, like gramfeed, to crawl through Instagram users. When we were going to launch in Korea, I knew that there would be growth in Korea. I spent hours trying to find people who were already on Instagram in Korea who we could feature as suggested users for new Korean language users to see when they sign up. It was pretty scrappy — I went to other platforms and places where our community spent their time and looked for passionate people. 

The reality is that often there’s not just one platform for any community. Notion, for example, has a bunch of people who are super passionate about their product. They run a very small Slack group for a vetted set of ambassadors. The community also started their own Facebook pages and their own Reddit pages and all of these different platforms. I think it takes some amount of creativity and scrappiness to just dig in and find passionate people.

Have you found that people generally have more success by making a single bet at the beginning, like starting one Facebook group or focusing on a Slack channel. Or is it better to try a bunch of things and see what works? 

I think people get really overwhelmed by the number of places that you communicate with them. If you’re a small company who’s firing signals off in ten different spaces, you’re probably stretched too thin to do anything really well. I think having a focused place to speak to a small community is an act of generosity and a guarantee that there will be some level of quality there.  I encourage people to cut away the places that they don’t need, depending on what your community cares about. For example, the Prokit community is mostly outdoors, running through beautiful spaces. Twitter might not be that important, but the community is sharing Strava and Instagram, so focus on those two. If you try to do everything, none of it will be that good, and you may not be able to build bonds between the members of the community because they’ll be scattered all over. 

There might be people out there who think this is baloney. They tried 10 different places and one of them caught steam. With everything, you need to navigate a combination of your best strategic approach and how many resources you have. If you’re trying to build a watering hole for community members to talk to each other, focus on a smaller number of people, make sure they know each other and that they can get the party started. It’s like having a party in one room versus having 10 rooms for the same party with three people in each room. It’s important to have a focused space where you can communicate with your community members. I prefer this strategy because I saw it work really well. 

It takes a lot of courage to do fewer things better. 

I’ve heard about strategies used to find what you say no to. Kevin Systrom, who started Instagram, would always say this quote that I think is attributed to Mark Twain: “I would have written you a shorter letter, but I didn’t have the time.” It all points in the same direction. The things you choose to cut may be some of the most powerful decisions you make, especially when you’re a small company with limited resources. You can only do so many things well. Are you making the right bets around where you put your time and focus? 

In general, people who were attracted to Instagram in the early days appreciated the thoughtfulness of the design. It was really simple, and it worked really well. It was in our brand to not spam people or over-communicate with them. I think what unlocked some of the passion for the product was the thoughtfulness with which we treated our users in communication and in the product design. Keeping things simple was in line with who we were and who the early users were that we wanted to bring in. 

When it comes to ambassadors helping to build a company or companies looking to build an ambassador program, where can it go wrong? Where can it go right?

I’ve done some work with Nike and Hurley around this, and I’ve also researched Lululemon’s approach. I’ve never been a sponsored athlete or an ambassador myself, so I want to acknowledge that there’s a lot of complexity that each athlete has with a brand. That said, I often see missed opportunities in terms of recognizing and supercharging athletes’ passion points.

Here’s an example of doing it well. At Hurley, I worked with the head of influencer marketing on their surf clubs. They invest in people learning how to surf in local communities. Hurley has a big roster of different athletes at different levels, but there was this one guy who clearly stood out. His name is Brett Simpson, and he used to be on the WSL. He’s really engaged in his community of Huntington Beach and is passionate about other people surfing. In response to this, Hurley rolled out a core program. Every Friday morning, Brett Simpson and some of the Hurley guys would throw a morning dawn patrol surf for the local Huntington Beach surf kids.

I thought that was one of the coolest community building investments that they did in my time with them. It was born out of the fact that they knew that Brett was truly passionate about his community and wanted to teach kids. They created this shared activity for people that was pretty simple in format. 

Bailey Richardson getting barreled surfing
Bailey in the barrel. 🏄🏽‍♀️

There’s a lot of value in an athlete creating a shared activity. Is there something that you and the people who care about your sport can come together to do, in-person or virtually? Instead of just posting on Instagram and having these asynchronous relationships with people, a shared activity allows you to bring your whole community together around a focus moment. I think that is really powerful. 

There’s a lot of people with big audiences out there today, but not a lot of people who are really connected to their audience or have a super-engaged audience. If an athlete can figure out a way to bring a community together, connect them to each other, and have a more engaged following than other people, that can be a real competitive advantage. Brett Simpson is not a super well-known person in the surf world, but because he was passionate, wanted to give back, and showed up for the shared activity, he got an outsized investment and an outsize platform with Hurley. 

Making sure that your sponsors know what your passion points are is key. For example, Questlove is a musician, but he loves food and has all these food partnerships. Is there some dimension of your personality or your passion points that you’re willing to get people together over? Brands really do like that specificity, and it’s a way for you to go a little deeper with your audience.

The Courage to Start and the Work to Keep it Going

This all points back to the people in the community putting themselves out there. On Prokit, Laura King (@laura) wrote an article about pregnancy and the athlete. Now there is a community of pregnant athletes who know and help each other. Someone can post something they care about that might help others, and the community starts from that act.

The thing that everybody says scares them the most when they’re starting a community from scratch is the idea that people aren’t going to show up. I remember we did some research on run clubs, and I asked this guy from Chicago what would keep him from starting a club. He said he would be worried that he would plan a run and no one would show up. But then he said that he likes running anyway, so if no one showed up, he’d still do the run and be happy. 

I think it’s good to start from a personal place, where you have enthusiasm and energy. You want to start a community around something that you want to keep doing or keep posting about, like Brett Simpson hosting his Friday morning surf club. Host the first couple of gatherings and then think about empowering other people to do it. That’s the switch that I think people should take. Go somewhere personal, do something you actually care about, and then think about how you can enable other passionate people to take the reins from you.

For people who already have a community and are struggling to keep it going, especially now when everyone has Zoom fatigue and there’s limited real-life interaction, what are creative ways to keep it going?

The number one thing I want to acknowledge is that this sucks. I love playing basketball, but I can’t play basketball with my communities anymore. There are some people that just prefer to do things in life in real life with other people. A lot of athletes are probably in that category. There’s no hack that can make the world what it was in January, and it sucks. 

What can we do now? When we do a workshop with clients who are starting a community, we have them answer three questions: Who are you bringing together? Why will they come together? What will they do together? These are deceptively simple questions, but getting answers that resonate and having cognitive clarity about those three questions is how to get a community going. Right now, I think a lot of people need to revisit the question of why. Why does their community come together? 

I play soccer here in New York with a team called Dike Soccer. I’m a queer woman, so I feel like I get to say that word. The group is gay women and non-identifying people who come together and play soccer. The why for the group was accountability for working out, or playing soccer, to do a hobby. They took the essence of coming together for fun and also for emotional support in the queer community, and they said, “How can we do that?” In today’s world, they’ve gotten creative with their activities. They’ve established a mutual aid network within the soccer team, so that sense of queer support continues. They brought on a player who was a licensed therapist to offer free therapy to people in the community. My favorite thing that they did was pet parades on zoom — it really tapped into the emotional support and joy that the team offers people. 

I think for some communities, the why has shifted. People who used to come together to skill develop around cooking, or around their ability to give public speeches, or around their timed miles, can’t get together anymore. Maybe some of that has shifted, given the state of the world and people’s emotional state. It’s your job to know why your people are coming together and to know if there’s anything you can do to serve that.  

One of my favorite shifts comes from an organization called GirlTrek. GirlTrek was started by two young Black women, both public school teachers. They knew that the public health numbers for Black women, children and adults, are some of the worst of any demographic in the country. They decided to do something about it at a local level, and took the girls in their classes for a walk three times a week for 30 minutes, per the CDC recommendation. Then they asked the girls’ moms to join them. People were so inspired by this giant group of Black women walking through the streets of Baltimore that they raised their hands to open up other chapters. Now there are thousands of GirlTrek chapter leads. They would walk all in different cities and towns every Saturday morning and then come together once a year to walk historical parts of civil rights history, like the walk from Montgomery to Selma and the Underground Railroad. 

Obviously, it’s not a great idea to have groups of people walking together now. So the founders created a podcast where they interview historic Black women, like Angela Davis, or tell stories of women like Harriet Tubman. People who are part of GirlTrek listen to the podcast. I’ve listened to it, and it’s pretty fun because the women are walking as they’re recording the podcast. So it kind of recreates, through digital tools, the same experience of unity, a sense of collectiveness with other Black women and exercise. I really appreciate that. They took their fundamental why and shifted to make it work during the pandemic.

Much of the outdoor industry is lacking diversity. Many companies are taking a deep look at their communities and seeing that they are missing people who should be represented. How do you take steps to bring new people in?

In researching communities, one thing that really stood out to me is that people join a community both for the thing that community does and the people they see doing that thing. For example, I joined a specific basketball team in New York because I wanted to play basketball with other women, and also because based on their photos on Instagram, they looked like people I might want to be friends with, a lot of artsy people playing basketball. 

I interviewed a group called The Dinner Party, which started as one dinner party between a group of friends who all realized they had lost a parent or a sibling way too young in life. They started out doing a single table and now there are 2,000 tables around the country. These tables meet every couple of months, and people talk about their current experience of grief. The headquarters team sifts through applications of people who want one of those tables in their lives and hand curates the tables. They choose 10 people and put them together. They told me that one thing they realized was if they put only one person of color at a table of all white people, the likelihood of that person coming back was extremely low. It was similar for people in non-traditional gender identities, and I’m sure other more marginalized groups. 

If you’re just starting a community and you want it to be diverse, as soon as possible think about how you can choose leaders who don’t look like you, and also, make that very clear. I have seen community leaders say very explicitly, we are a Black Lives Matter community and if you are not on board with that, it’s cool, but you don’t need to be here. I think it is important to clearly communicate who is welcome and what the rules are through a demonstration of who is in your community.

If you’re realizing that your community is very white, or very homogenous in some way, you could start by figuring out if there is a way that you could support other racial groups. Could you offer some kind of resource, audience, or support to a group that’s already in that space? For example, there’s a lot of different groups, like Black Girls RUN! or Black Girls Surf, that are popping up in traditionally white sports. I would see if there is a way your community could support them, spotlight them, or possibly collaborate with them. Supercharge them, build relationships, and demonstrate what you care about.

Where can people find you?

Weirdly, I deleted my Instagram account in this moment of “I’m ready to graduate, I spent enough time on this platform.” I didn’t stop spending time online though, I just put more time into Twitter.

You can find me @baileyelaine on Twitter. Also, I have a public website, Bailey E Richardson, and my work website, People & Company. And on Prokit @bailey.

Bailey’s book Get Together and her podcast, also called Get Together.

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