The Future of Hybrid Digital Communities

Digital Citizen

On this special Philly Tech Week episode of the Digital Citizen podcast, Fastmail COO Helen Horstmann-Allen speaks with Alex Hillman, Will Toms, and Michelle Freeman, three of the savviest digital citizens in Philadelphia about community building offline and online.

Michelle is the Founder of Witty Gritty, a civic-focused marketing events engagement company based in Philadelphia, and Amplify Philly, an initiative co-run with REC Philly aiming to amplify the intersection of business, tech, art, and more. Will is the Co-Founder of REC, a company that works to get independent creatives paid for doing what they love. Alex co-founded Indy Hall, Philadelphia’s first coworking community, which has been gathering people since 2006.

▶️ Guest Interview - Alex Hillman, Will Toms, and Michelle Freeman

🗣️ Discussion Points

  • Alex explains that the difference between community building on and offline is that offline community building gives you many things for free, such as serendipity. Natural and organic conversation is one of the things that makes a community so special, which is very difficult to build online. Online, you have to be specific and intentional in building community.
  • In our hybrid world, being online serves as an enhancement for in-person experiences. It allows people to keep in touch between meetings through tools like email and Slack and make connections with people they can later connect with in-person.
  • Our guests are all three extremely proud of their home city of Philadelphia. What makes the city so special is that the city has more creative talent than any other city per capita, even though they don’t have the entertainment infrastructure of New York or LA. REC Philly highlights the resources Philadelphia has to leverage to entice creatives to stay rather than relocate to another city.
  • The first thing people can do to become better digital citizens is shift their identity online from building an audience to building a community. As a community builder, your role is to create a space for people to connect with others.

⭐️ Takeaways

  • It is important to add value to the spaces you inhabit, whether they are on or offline.
  • Simplicity makes participation accessible. Something as easy as encouraging people to participate in thematic name tags (or screen names on Zoom) can spark meaningful conversations.
  • When it comes to community building, “Onboarding is forever.” Be intentional about the type of community you want to build and start laying that groundwork early on to help foster its growth.

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Helen Horstmann-Allen: Welcome back to The Digital Citizen Podcast. I’m Helen Horstmann-Allen, the COO of Fastmail, the email provider of choice for savvy digital citizens everywhere. I’m so excited to be filling in for Rik today to help bring you new special Philly Tech Week bonus episode of our show. Here with me today is Fastmail’s content marketing at coordinator, and the producer of our show, Haley Hnatuk.

Haley Hnatuk: Hi, I’m Haley. This is our first live recorded podcast episode ever, and because of that, we’ve decided to bring you an extra-long episode so you don’t miss out on any of our amazing guest responses. Today we’ll talk to three of the savviest digital citizens in Philadelphia about community building on and offline. They’re experts in building and growing hybrid communities and bringing people together no matter where they are. Helen, please tell me a little bit about Alex Hillman, Will Toms, and Michelle Freeman, our guests.

Helen Horstmann-Allen: Alex Hillman is the founder of Indy Hall, one of the world’s oldest, fully independent co-working communities, where our panel was hosted. He’s also the co-founder of the 10,000 Independence Project, which seeks to help 10,000 people become sustainably self-employed in the Philadelphia area in the next 10 years. Our other two panelists are also involved with this project. They are Michelle Freeman, a lifelong Philadelphia resident, and the founder and CEO of Witty Gritty, a civic-focused marketing events engagement company based here in Philadelphia; and Will Toms, co-founder of REC Philly, which stands for Resources for Every Creator, a Philly company working to help get creatives paid to do more of what they love.

Haley Hnatuk: That sounds like an incredible lineup. How did this panel happen?

Helen Horstmann-Allen: Philly Tech Week is a yearly event in Philadelphia, led by, a news organization that serves a community of tech professionals. Fastmail helped sponsor the event this year, and we also led this panel. Haley, can you tell us a little bit more about what went into planning the event?

Haley Hnatuk: When we were planning this event, we knew we wanted to do something that aligned with our values. As a staff, we often think about Fastmail as human-to-human email, so we wanted to do a Philly Tech Week panel that highlighted how to build connections with the people around you. Helen, what are some of the things you talked about with our panelists?

Helen Horstmann-Allen: So, we talked about the similarities and differences of building a strong community both on and offline. We dove into hyper-local community building, and how to enhance engagement locally around your digital projects. And, like with Rik, please stick around to the end of the episode, and we’ll give you some of our takeaways, which are things you can actually do to become a better digital citizen. You can also find them on our website at So, at Fastmail, when we talk about digital citizenship, it’s really around how do we bring the best of ourselves to our online lives as well as our offline ones. Alex, thank you for hosting us in this beautiful space. What do you think the differences are between community building on and offline?

Alex Hillman: So, I think offline community building gives you a bunch of things for free. The biggest one of them is also, I think, the hardest to create online, and that is serendipity. And the experiences of community, when people talk about what community feels like, and you kind of reverse engineer that to what moments make that feeling happen, it’s usually conversations you didn’t know you were going to have. It’s overhearing a conversation you didn’t intend to be a part of, and things like that. And it’s not that you can’t do those things online. You absolutely can. But as we’ve learned over the last few years, it’s different, and in some ways it’s a heck of a lot harder. So, I think the biggest difference is, online you have to be 10 if not 100 times more intentional about designing the experiences because you don’t get the free elements that the real world gives us just by simply being in a place.

Helen Horstmann-Allen: I’m actually going to jump to Michelle because I think you create so many events, and when we talk about being intentional about creating that, what are the things that you look to build in? Like, what opportunities does hybrid programming create, and how do you pull in this really intentional element for serendipity?

Michelle Freeman: That is pulling back from the notion that clients we work with need events or marketing, or sort of prescribing ahead of time what they need, instead looking through everything through an engagement lens. So, really letting us go to clients and partners and say, “What message are you trying to get out? What people are you trying to engage?” And then looking at our toolbox to figure out what things make the most sense for their engagement needs. So then, what that does is it allows us to really look at and assess the purpose for different types of gatherings, or at least the initial idea of that, and thinking about things that might serve better in a virtual space, given that it might be winter out, or the time of year, or also like things that are more about content-specific, heavy things versus networking. So, figuring out which things feel like they belong and fit better in a virtual space. And then making the in-person opportunities count, right? Make them count even more, but then make them feel like they count more because you’re building up and using the online space to build that momentum and anticipation for people.

Helen Horstmann-Allen: So, Will, REC Philly is a community of creators, so you’re really looking at this almost two levels. Right? What have you learned about engaging with your community of creators, but also helping them engage with their audiences online?

Will Toms: I think something weird happens when you get on the internet, where all of a sudden you think you have to be a whole different person than you actually are. And you have to remember that, like, that’s not true. If you take a step back, there is a lot that we can learn about how to engage online from how we engage in real life. Right? So, the idea, for example, a lot of our community members are like, “Man, I really want to grow my audience, but I don’t know how to do it.” It’s like, “Well, in real life, if you want to go make friends, how do you do it?” You go to the places, right, where you know the types of people you want to be friends with are hanging out based off interests, and then you stick around and kind of like first overhear what conversations are being had, like Alex was alluding to. And then when it’s the right moment, you don’t just talk about yourself, but you add value to the conversations that are already happening. It’s go to the places where they already are, add value before you ask for anything. Right? And I think sometimes we forget. But I think a lot of it just comes back to how do we do it in real life, and let’s show up that way online, and just respect that it’s the same, not you have to just put on this, like, avatar of, like, online Will.

Helen Horstmann-Allen: All right. So, you’ve told us we got to get online. What do you know now about engagement that you wish you knew starting out?

Will Toms: The first one I would say, and this is, again, something we talk about with our members at REC all the time, document more than you create. A lot of times what gets in the way of us showing up authentically on the internet is, we know that we got to create content, right? Everyone’s like, “Content is king,” or whatever that means. But when we go on Instagram, we get that analysis paralysis because we’re like, “What do I post?” Because I can post anything. And what I’ve noticed is, the post that I spend the most time architecting and thinking that I have to literally create and make perfect, the commercial of a post, those are not the things that work best. It’s really the moments that I’m actually not intending to create something special, but I’m literally just documenting what I’m already doing. Right? So, I could go in front of a backdrop and say, let me just drop gems to the audience, right, or I could say, let me just turn my camera on and let people see that I’m having a conversation with other community leaders right now about this, and let them just see a peak into my world. And I think that will just help a lot of folks, especially as they know that they need to create content because that is a bit of the currency that builds community, showing up, showing people who you are.

Helen Horstmann-Allen: Alex, a tip you want to share?

Alex Hillman: I think it’s, sort of a complement to that, which is, don’t try to mimic or copy offline experiences online. I think about an offline event or experience, and, I mean, we saw a ton of this during the pandemic. People are trying to turn happy hours into Zoom happy hours. And there’s a reason it doesn’t feel right because it’s not right. Like, that’s not how we interact with each other, and it’s exacerbated by the fact that we’re using the same grid of faces to have important business meetings, and I’m supposed to socialize in the same thing? And, like, there’s no context switching. So, if you try and take a thing that worked before and just do it online, it probably won’t work. But if you take that thing and go, “Well, what made that work? What made that special? What made people want to do that?” And then, is there a thing that the internet lets us do easier or better or differently? Kind of really redesign it for the tool or the moment, whatever it is. But just like carbon-copying offline events online essentially never works. But the hard part, the real work is like, why do people show up in the first place? Why do they leave with a memory? And when you can find those little granules of something, that’s the opportunity to go, “Well, how could we create that moment again using this new set of tools?”

Helen Horstmann-Allen: Michelle, you’re in a tough spot now.

Michelle Freeman: I know. I mean, the word enhancement comes to mind, so it’s almost like, when possible, to Alex’s point earlier, you know, meeting in person creates this different type of experience and these different serendipitous moments. And I look and think about sort of online engagement plays into the in-person engagement, and how being online really serves as a potential enhancement to whatever the in-person experience might be. That’s kind of what it feels like. The other thing, too, that might feel like that comes to mind is, there’s this interesting moment, too, when we couldn’t meet in person, a lot of people called me and they were like, “What do I do?” And a lot of head scratching around, “Well, how are we going to do community engagement if we can’t meet?” And I was like, well, actually, if you think about it, the way to connect with people… to Will, your point, just kind of being in the moment or trying to connect with people as you would in real life… would be to pick up the phone or text message or, say, you know, knock on somebody’s door and have a conversation with them. So, even using technology as a way of an online tool, yeah. And just thinking about how we don’t have to always over-complicate or over-prescribe things, and it can really just go back to the most basic way of connecting with people. Which I think, you know again, we can get caught up in signing up for all these accounts and creating all this content, but we should remember, at the end of the day, like, just people talking to people, and how can we keep that authentic, which is harder to do online, I think, when you’re thinking about the translation from off to on.

Will Toms: Can I add one more thing to that?

Helen Horstmann-Allen: Yeah.

Will Toms: I think also what’s really helpful for people to remember, it’s easiest to show up online and to attract your tribe if you are clear about who you are and what you represent, right? I think sometimes a lot of folks get online, and then they get stuck when they’re trying to, like, post something or build audience because they haven’t really distilled, what is that thing that I want to build the community around? What is that shared interest? What is that commonality? What is that belief? What is that value set? And I think if you really can distill that… And that’s hard work to say, “Hey, I do all of these things. I care about all of these things.” How do you bring it all down to a sentence? And if you can get that into a clear mantra or an idea, it makes it so much simpler when you get ready to post, because you know what you want to say, and you know who you want to say it to.

Alex Hillman: And I’ll build on that as well. I think a lot of times, especially when we go online, we start thinking… We get into promotion mode. That’s come up as a theme here. And when I think about community-building stuff, an internal mantra that we’ve had is invitations instead of promotions.

Will Toms: Love that.

Alex Hillman: Right? And so, you can think of community building as simple as, “I’m going to go do this thing. Anybody want to go do it with me?” It doesn’t need to be more complicated than that.

Will Toms: Gold.

Alex Hillman: And the beauty is, you can do that online or offline. “Hey, I’m going to go watch… I need to watch a bunch of YouTube videos to do research on a thing. Anyone else interested in this? Let’s open up a Zoom or a Discord channel and watch them together, and have a little back channel in the text.” That’s where you’re thinking about how do I do a thing I was going to do anyway with one other person? If you can do that, you’re building community. Two people, even better. Three people, even better. So, I think it’s so easy to overcomplicate what community is, and I’m not here to, like, debate the definition so much as like what is the element of experience? It’s, “I’m doing a thing with another person.” It doesn’t need to be more than that.

Helen Horstmann-Allen: Amazing. All right. Well, as anybody here who knows me knows I am a super proud Philadelphian. I love the city of Philadelphia. All three of you have been incredibly successful at building a strong local audience in a really unique, special thing that I am so proud to have as part of our city. What is Philly to you? Why was it important for you to start here?

Will Toms: I am extremely proud and blessed to be from Philadelphia, especially to be building the business that I’m building because I know that Philadelphia has more creative talent than any other city per capita, especially in the music and art space. So I felt like Philly was the perfect breeding ground for what we’re building, which really is like infrastructure for creative entrepreneurs because we are that city that has a tremendous amount of creative talent, but we aren’t the industry infrastructure that folks think of when they think of entertainment like New York and LA. So that gave us a really amazing opportunity to say, “Why did a lot of our favorite artists think that they needed to go to New York or LA to be successful?” Let’s take a look at what that perception was, and then let’s say, “Wait, Philly has resources, right? Philly has a lot of amazing folks. Philly has this, this and that.” So we had an opportunity to say, “No, no, no, we can build that here.” And then the other amazing thing about Philadelphia is folks are not afraid to tell you when they love you, and they’re not afraid to tell you when you’re dropping the ball. So I think it builds a set of resilience.

Alex Hillman: It’s so important.

Will Toms: Right? And that’s good feedback.

Alex Hillman: People here are so real, and take that for what you want, but that is such a undervalued resource compared to other cities.

Will Toms: Yep. I feel like if we can, for lack of the better term, but if we can make it here in Philadelphia, we can make it anywhere because Philadelphians are going to tell us when we’re not doing it right. And that’s a blessing actually.

Michelle Freeman: I think we do have that energy. Exactly. I, too, am from Philadelphia and I started as a teenager being a show promoter, giving out flyers on the street and just wanting to, like, experience everything and party and all these things, and at an early age also got very civically involved. So I think once that started to grow and I was able to make more observations and reflections out of that, I realized how committed I am and interested I am in community building and community engagement, and that takes a long time to plant those seeds and have those roots grow. So it just came to me at one point where you have the itch, “Well, what if I moved to San Francisco? That would be cool. Right?” I mean, I kept getting pulled back to Philly, realizing how much it meant to me to be able to continue to, like, nurture and participate in the communities I am a part of and I’ve helped grow here.

Alex Hillman: Well, unlike these two, I moved to Philadelphia from the far away lands of the Lehigh Valley, Pennsylvania, which, dear listeners, is a mere hour and a half north.

Michelle Freeman: Welcome, Alex.

Alex Hillman: But I moved to Philadelphia to go to Drexel University for two reasons. One was the co-op program, two was sidewalks. I grew up in a place where you had to drive everywhere, and I wanted to go to school somewhere where I could walk to things. And so I left school to go out on my own, start my first business as a freelance web developer, and quickly built my network everywhere but Philadelphia. I had an online network in San Francisco, New York, Chicago. I’ve got clients and collaborators. It’s all online. And the thing I do have in common with these two is thinking maybe I have to leave. It was a failed attempt to move to the Bay Area for the dream Silicon Valley startup job that made me step back and go, “Why was I leaving in the first place? This city rules.” If I could find my people, if I could find folks who, like me, want to make things, put them on the internet, have some sort of sense of control and independence over their work, where they work, how they work, who they work with. If I find a handful of them, I never have to leave. And 21, almost 22 years later, yeah, a very place-based business.

Will Toms: With a few more than a handful of community members.

Alex Hillman: That’s right.

Helen Horstmann-Allen: Well, Alex, I would love to hear more about how being in Philadelphia has grown you into 10k Independents.

Alex Hillman: What is 10k Independents? The 10k Independents project started as a reaction to the Amazon HQ2 project, which was this evil genius move when Amazon pitted a bunch of cities across the country against each other to convince them that they were the best city for Amazon to build its headquarters. What frustrated me was watching people do back flips for this giant corporation on a promise of 50,000 jobs, which let’s be clear, 50,000 jobs for the city, thumbs up. Good thing. One company creating 50,000 jobs is about the worst way to do it. But instead of complaining, I said, “What could we do differently?” And thought about what my friends do, thought about our approach of like building small things that add up to big things and came up with the math, because I am a nerd, that if we help 10,000 people become sustainably self-employed, right, get people who’ve started something on the side to the point where they can quit the job and not only is it paying their bills, but is as good or better than they would get from a full-time job doing the same thing that, A, we’d have 10,000 people have creating self-employment because 1099s are real jobs, too. But then some percentage of those people would also go on to say, “You know what? The only thing keeping me from helping more people is the hours in the day.” And now that my oxygen mask is on and I can take care of myself, my family, and my community, I think I want to hire my first person. I have this firm deep belief, and I’ve had good bosses and bad bosses, and a lot of times the big difference is that person’s motivation to bring a person on the team. Is it because I need to solve a problem or because I have an opportunity that I want to share with another person? And I think if you put your oxygen mask on first as a business owner, you’re going to approach your first hire in a distinctly different way. So the 10k Independents project is sort of the intersection of the last decade and a half of Indy Hall as well as the other business that I run is an online education business helping people who’ve generally jumped into freelancing or some sort of creative services to build product-based businesses. I’ve seen all the kinds of things that people do right and do wrong, and it’s not that I have all the answers. It’s that I know that Philadelphia’s got people who can do it. More people can do it than do. And that if we do what we do best, which is bringing communities together, lifting each other up, sharing resources, we’ll see more of those successes and they’ll compound over time to the point where we’ll not just create 50,000 jobs. Our conservative projections over the 10-year period look more like 87,000 jobs. Ultimately, this is my love song to Philadelphia in a lot of ways, the next 10 years of my life. It’s a Philadelphia goal. By sharing that goal, that’s how we all come together. I think if there’s anything we’ve learned over the last few years is a shared goal is the most powerful tool to bring people together.

Helen Horstmann-Allen: So Michelle, Witty Gritty organizes lots of hybrid events for lots of people, and we’ve talked about how online community is different than an in-person community. But how do hybrid events and hybrid conferences benefit Philadelphia?

Michelle Freeman: I think it does two things, and I think part of it will depend on your intention to gather people, right? But there is something really amazing and beautiful that has been happening, I think, with hybrid events and the ability to be able to connect with a larger audience, different communities outside of geographic boundaries, right? So really thinking about how you can connect and grow audience nationally and globally, and thinking about your twins in other places and other cities and how you can link up with them. There’s a lot of power in that, and I think it needs to be intentional, so it’s not just like a, “We hope people come from all over and we don’t really have a shared goal or shared purpose.” I was the former chapter host for Creative Mornings, a monthly lecture series that has global chapters all over. We had to switch a lot our programming for over a year to virtual. But then what happened was we were able to easily connect in real time with all these other chapters. So we were already part of a global community, but we were not necessarily connecting in real time with our talks. We were able to experience each other’s programs after the fact, which is great, but this did something else. It sort of did this other sort of… It sort of revealed itself this piece that probably was a possibility of being there, but we just didn’t realize it. Being able to, kind of again, connect with your twins or like counterparts in other places has been really interesting to see. I also think what that does for Philly is put a really great lens on Philly. Any opportunity we’re able to show and tell people who we are, I think the better, because I do think we’re still a city from a perception standpoint where go to things like South by Southwest or other conferences and things, and often what I find is people have a lack of information about Philadelphia. And because of that, they sort of forget that we’re here or they have the sort of, like, top five things they think about. I see that as an opportunity just kind of moving forward that we have the opportunity to fill in those blanks for people and not so much have to completely change or course correct a perception, but I do think these opportunities for hybrid help us kind of create more of a cycle of eyeballs on Philly.

Helen Horstmann-Allen: So Will, you’re going to have a big opportunity to go out to Philly’s obvious twin, Miami. How has your experience there differed?

Will Toms: That’s a great question. It’s different in a number of ways. The first way, I’ll just say it’s been really fun to build a similar thing, but do it with intention of being responsive to the community that already exists there, right? Knowing that Miami culturally is different in a bunch of different ways. For example, in Philadelphia, we’ve got 10,000 square feet and we’ve got four recording studios and a couple visual labs. But in Miami, we know that visual art is a bit more prominent than music making is in Philadelphia, right? So having different utilities in the space and amenities to service that audience. There’s a different flash to a Miamian than a Philadelphian. It’s like you just got to be utility driven in Philly, because we’re like, “Give us the thing, keep the frills.” But in Miami, they’re like, “No, no, no. What’s the hospitality looking like though?” So we have to adhere to that. So I’d say that’s how we’ve been thinking about how do we make sure that this is something that still represents the brand? But the product and the services are meant to serve the people, so we have to be listening enough to be adjustable to what’s there. And I think that’s what any good community builder does. They listen, right, more than anything. One of the things that we knew right away was like, we’re not going to Miami and being like, “We are the creative guys here. We’re going to solve all your problems.” Not at all. It was just really about going there to learn what was happening and then saying, “Oh, wait, there’s a lot of amazing community leaders that are already here that are already doing this work, that are already waving the flag for independent creators.” How do we approach them, build meaningful relationships and say, “Hey, we have a model that’s working in Philadelphia. Let’s partner up to bring this to your folks in the way that they need it.”

Will Toms: So it’s really been about identifying the right folks, giving them the model, filling in our gaps, and then getting out of the way where we don’t need to be. Honestly, some of my favorite events happening at REC right now are not produced by REC. They’re led by our members. And when we see that, now we’re taking the positioning of let’s just pour gasoline on what they need. For example, we have a member, his name’s Luis Marrero. He has a poetry open mic called Voices In Power. He had already been throwing poetry open mics for a decade before he became a REC member, but he was only doing them in Philadelphia. He sold out every open mic for almost two years while he was coming to REC. But we just gave him what we could add, which was, “Yo, let us operate your backend right? Let’s do the logistics for you so you can do what you do best.” And that allowed him to not only do amazing experiences at rec for our community and beyond, but now he’s in five cities around the country, and he just did his first one in London, right? And that’s what we’re all about. It’s like, how do we be the infrastructure for what you need so you can do what you do best, which is usually create, right? And the more exciting parts of creativity.

Helen Horstmann-Allen: Will always has an amazing inspirational story. We’re like, “Oh my God, I’m going to cry.” But there are challenges too, right? Like Alex, Indy Hall had to pivot hard during COVID to become mostly online. What did you have to implement to bring your in-person culture online? And what didn’t work, I guess, too?

Alex Hillman: Couple things come to mind. The first, I would put into it had nothing to do with tools or events or experiences. It was like 99% of the work was acknowledging the moment and letting our community know like, yo, we’re still here for you. None of us know what’s going on, but at least we’re in this together. And in that moment, it felt like in a weird way, the thing we’d been training for every minute up until that point, which is like, we come together the most and we have a problem to solve. Right now, we don’t even really know what the problem is yet. We just know that we’re stuck at home, and it’s scary out there. And so probably the first six weeks, a lot of it was hosting to sessions where we could get together, and whether it’s have a conversation on Zoom where we’re not talking about the pandemic, just talk about literally anything else. Or the flip side, like, hey, if you’re scared, this is an okay place to tell… These are people who you recognize and care. And we’re not here to give answers. We’re just here to listen. And I feel like that first phase of the transition was just as much for me and the team to be like, what do we do? I don’t know. We show up for the people. That’s what we’ve always done. That’s what we’re going to do now. That’s it. And the second phase was a little more… We had a really distinct advantage that Indy Hall has had an online community since day one…

Will Toms: Facts.

Alex Hillman: …since before we had a space. And so Michelle said something earlier about online community can be continuity for an offline experience. And our online community was that on steroids, where a thing people did not realize about Indy Hall prior to the pandemic, 70% of our members came to the space less than once a month.

Will Toms: Blew my mind every time I heard you say it.

Alex Hillman: And these are people who they paid for years to come to this space maybe once or twice a year, if that. And for them it was more of, I know this is where my people are. I want there to be a place I can go. I want to know it’s there when I need it. And that it is there gives me a sense of comfort. And so coming into the pandemic, I was like, well, we’re going to continue doing that. That doesn’t have to change without the space. But then also, like, we’ve been using Zoom since 2016. It’s not the flex that it sounds like, but we knew some of the tools. So it was like, okay, how do we use the tools in a more sophisticated and advanced way? It wasn’t what buttons do we press. It’s how do we facilitate the experience? And one of the moments that comes to mind for me was the realization that, it ties together a bunch of these threads, is, like, Zoom is a virtual room that you can access from anytime, anywhere. There’s no windows, no doors. You don’t know if anyone’s inside until you go in. And what’s the worst community experience you can have, to walk into an empty room and be the first one there. It’s like, how do you solve that problem? So we actually built a little bit of software that connected our always on, any member can use it Zoom room to our Discord chat, that when somebody goes into that room, automatically pops up a little message and says, “Scott’s hanging out. Would you like to go meet them? Here’s the link.” They click it, and all of a sudden you’ve got two people, three people, four people.

Will Toms: That takes you back to the AIM [AOL Instant Messenger] days of like, “Alex Hillman’s online now.”

Alex Hillman: It was very much inspired by that. And it was one of those things, the tools would not do what we needed them to do, but there was a moment that I was like, if we can recreate this moment, the idea of just opening up Discord and being like, ”Oh shoot, there’s people hanging out. I’m going to go see what they’re talking about. I hadn’t felt that in months.” And once we did that for the first time, I was like, okay, we’re just going to look for more ways to do that. And the rest of the time is building on that, building on that. And it actually got to the point after like eight or 10 months, we were like, “I think we could offer this to people, not just as a way to keep people from canceling, but we could start signing up new members again.” There’s this core of people that had only ever met online seeing each other in person for the first time. And I feel like that’s one of the kind of magical experiences that I hope everyone gets a chance to… You meet people through social media, whatever, then you finally meet them in person at a conference. And that is just, like, this kind of world tightening, beautiful moment, and I feel like we’ve been able to create a version of that extends further beyond. And now we’ve got members all over the country in multiple continents, and what’s fun is watching them go visit each other. We’ve got a member in a small town in Northeastern Canada, goes and spends a week with a member in Portland, and we see pictures in our Discord here in Philadelphia. But, like, those are the two pieces. It was like, show up for people, which we’ve always done, and then look for the things that we always did, and go, “How do we reinvent this?”

Helen Horstmann-Allen: But Alex had to build his own tools. Michelle, you do this for so many people. Are there actually any tools that you would help people recommend?

Michelle Freeman: Yeah. I mean, there are two sides of that. One, again, I think that there’s this sort of theme of like “back to basics” and keep it simple. It gets harder and harder because I think there’s also the challenge of the just, like, online adoption with certain tools and things. So I do think, OG Zoom user over here, but for everybody else who caught up kind of knows how to use it at this point, right? So a one side, there’s a lot of spaces where I think simplicity is best, so you kind of remove as many barriers for people to participate. On the other hand, I think depending on we’re working with a client, different organizations, really looking for, like, a tool that they can really invest in. Part of it is sort of… There’s never going to be a tool that does all the things that you need it to do, and you have to be willing, because it’s an online space to experiment to a certain degree, because there had been so many endless failed Slack channels I could tell you about with communities and stakeholders that said they wanted something, and they all checked the box and said they’d try it, but then the adoption of that didn’t really work. So there are all these sort of gray spaces where that piece of it becomes really complicated, and then it sort of does exactly the opposite of what you want it to do, right, in terms of engaging. So part of it I think is almost starting out simple if you don’t have something in existence already, and then trying to vet out what makes the most sense for the most people. I mean, when you’re working with people who are more in tech or in certain spaces where certain tools, Discord or Twitch or Slack are just part of the masses, then more then new people come on and it’s not as big of an adoption problem, but we see it really… It’s really difficult, especially when we talk about other kind of more residential neighborhood community groups or other people who might have different varying degrees of tech education and comfortability with tech. So that’s why sometimes, like, text message is king in a lot of ways.

Helen Horstmann-Allen: Yeah, I was going to say email is ideal for low engagement users, right? There’s a lot of platforms with high engagement audience. Great, let’s get on a Discord. Let’s get on a Slack. But some nonprofit that I work with sent me an invitation to their Slack, and I’m like, I absolutely do not want to join your Slack.

Michelle Freeman: Exactly.

Alex Hillman: It’s one of my criteria for picking community tools. Rule number one is, if there’s a tool that the majority of them already use, that’s your tool. Rule number two is, does it have good, smart email notifications that they’re in control of? Everything else is gravy.

Helen Horstmann-Allen: Also, when we talk about digital citizens and we talk about creators, right, the challenge there is real. I’m going to say to you, Will, what can all the rest of us do to be better digital citizens for creators?

Alex Hillman: Smash that like button.

Will Toms: Facts, right? Completely unshameless plug. The first thing you can do is go buy our book that is completely all about how to make money on the internet and build communities on the internet called “Uncommon Sense: Your Strategy Guide to Creative Freedom”. And you can get that at I think the first thing that folks can do to become a better digital citizen is really shift the identity of what you’re doing online from “I’m building an audience” to “I am building a community”. I know that, that may sound a little redundant, but I think you just show up on the internet completely differently when you understand that you’re looking to build community. And for me, as someone who serves creators and artists, I think of artists, or at least the best artists are the OG community builders, right? When I think of artists like Beyonce or the Grateful Dead, right, or Phish, and whatever you call the audience of people who follow them, they build these communities where it’s almost not even about the artists so much anymore. It’s about, whoa, you’re wearing a t-shirt of that obscure band I like. Now I know we have something in common. Let’s get to know each other. So I think the first thing is just know that as a community builder, your role is not always even to get people to connect with you. It’s about what can you create to get people to connect with other people. And I think once you, like, change your brain to facilitate that, it really makes it a lot easier for you to create meaningful impact for your folks. And that’s what’s going to get them to stick around. That’s what’s going to get them talking to other people about you and inviting them to join. It’s that word of, what are you doing that’s really remarkable? And Seth Godin, you know, one of my favorite marketers and community builders, he says that a lot, literally remarkable, like worth talking about. And those are usually those deep meaningful experiences that you only create when you get out of the way and let the community embrace itself.

Helen Horstmann-Allen: Michelle, you work with communities that kind of spring up for events. How do you get those attendees to really show up and engage?

Michelle Freeman: There’s a handful of things that we take into consideration. I think, you know, I think about ways to sort of do these, like, very sort of passive and light curations, sort of facilitated moments where you don’t realize that things are set up in order for you to connect with people. It sounds really simple, but we use the name tag, the function of a name tag to do a lot of that, and have found these little sort of inexpensive ways to use just even the notion of a name tag to better connect people, even as simple as putting, like, a little fill in the line prompt so that you don’t just have to connect with somebody based off of their employer or work affiliation, but instead about something about them or something more thematic. And then the other thing too is the sort of, and this is showing up more than it has in the past, but this sort of tension behind wanting to have this program and have all the people who need to speak speak versus having more open space for people to connect with one another and finding the in between spot to build a little bit of structure around that I saw in a lot of clients we worked with who are willing to try different things. And think about how we interject technology as well, right? More openness to, what does it look like if we have some type of online experience that compliments this? Or how do we document these events differently so that they can live beyond the time that they’re happening? And how do we make sure that, you know, to the point, not that we’re hoping that people post on social media for the promotion aspect, but we want them to share something meaningful about their experience in real time as they’re experiencing it. Sure, to create a little FOMO [fear of missing out] for people who didn’t come, but also to document that feeling as it’s happening.

Helen Horstmann-Allen: We’ve talked a little bit about kind of that mindset shift, right? And other than the invitation to do so, like, what do each of you think is an effective way to create that shift or to set that lens? You’re coming into this space. This is how we want you to engage.

Will Toms: I like the old school way of saying it. One of the things I like about Discord, for example, when you log into a discord, usually one of the first things you see is community guidelines. This is how best members of this community show up. And it tells you directly, like, “Here’s what’s kosher here. Here’s what’s not kosher here.” Because it’s like you can’t just hope that people are going to know how to navigate your community in the best way, especially if you’re weird. And like at REC, we’re kind of weird and quirky, so it’s like we have to teach people what it means to be a part of our community. And we do that in sometimes subtle ways and sometimes more overt ways. But like, when you walk into a REC, one of the first things you’re going to see is, “Independent doesn’t mean alone”. And that kind of signals a bit about how we think about the creative industry, which is very counter to, like, the old school industry of music labels and all that stuff. For us, it’s like, no, independent doesn’t mean you’re out here by yourself and you got to shoot the video, and you got to record your song and tie your shoes real good. It’s like, no, we can do this together. The other thing, you open the door and then it says, “There was never a place for people like us, so we decided to create one.” Right? Things that thoughtfully get people thinking about our philosophy and how we see the world, but then also literally you’re going to see an email welcoming you to our community that has community guidelines. And I think it’s just so helpful sometimes to just tell people, because I like to believe that most people actually want to be a meaningful contributor to your community, you just have to teach them how to do so. And if they don’t know how, it’s not on them, it’s on you to set the culture, right? First as the leader and then as the staff and the team, and then as those top members. And then that’s also why it’s important to uplift your best community members, because they get to model what it looks like to the newer folks. So I think that’s like the best way, because really what you’re asking about is, how do you build culture? And I think that’s how it’s done.

Helen Horstmann-Allen: Although I am going to know that for both you and Alex, write it on the wall, seems to be a strategy.

Will Toms: Straight up. Right?

Alex Hillman: Constant reminders. Well, I mean, I’ll agree that onboarding is critical and it can take so many forms, both explicit and implicit. I think what people forget is that onboarding is forever. And, one of the things I’m super proud of is one of our core approaches with Indy Hall is you’re not going to make anybody do a thing they don’t want to do, as much as you can’t really make them do a thing they do want to do, you can help them do a thing they want to do. And so we’re constantly listening to things that members want to do that feel in line with the community values. And we use that as a conversation, be like, that sounds awesome and here’s why. So that’s an opportunity to like, if they haven’t made the connection of why we’re excited about it, we tell them explicitly. And then we go, and this is your playbook, is how can I help you do it? Right? Helping people see someone like themselves do a thing like what they want to do visibly is, in my experience, the most valuable inspiration you can provide to somebody to be like, “Oh, they can do it? I can do it.”

Will Toms: Because it’s incredibly hard to be what you can’t see, right? And that’s why representation matters, and that’s why stories are important. Like, folks have to be able to see the success in someone like them well before they actually can muster the belief to do it themselves.

Alex Hillman: And when we’re doing onboarding, whether it’s online or off, it’s not, here’s the desks, here’s the kitchen, here’s the conference room. It’s, “Here are the kinds of things people do in this. Which ones are you most interested in?” So we’re constantly kind of serving, “What are you here for?” And then we make it our job to help them see the clearest line or lines, because there’s more than one right way to do it, and there’s more than one right speed and timeline to do it on. It doesn’t need to be right away. Some people take like, I’ve seen people take years before they show up, not like show up in the room, but like show up themselves, ready to do a thing. And if you meet them in that moment then, I find they’re blown away that you even noticed. And so like, yeah, all the energy gets put on the very beginning. And the very beginning the first impression is important, but I think the follow through is where the magic happens.

Helen Horstmann-Allen: We always like to close by asking our guests to reflect on something concrete we can all do to improve our lives online. I just want to run down the line and get a quick answer from each of you. We’ll start with you, Michelle. What’s something you do or wish you did more often, that helps you lead a richer, healthier life online?

Michelle Freeman: I wish I didn’t mindlessly open up Instagram and start scrolling. I think to the point that Will made earlier about showing up online the way that you would in person or how you connect with people, I think that I want to be more mindful and intentional in my app use, and maybe supply that thought. If I’m going to open this up, how am I going to meaningfully engage with somebody, whether it’s answering a DM directly, or engaging on a interesting post or giving somebody a shout-out and taking the actual time to ingest whatever I’m looking at.

Will Toms: I’ll say mine. But just to piggyback off what you’re saying, like that’s such a good… it’s such a good way. I want to just give everyone permission to just think about the internet, just like you think of the real world, right? And even that goes into like, I don’t go to the hospital for the same reason I go to church, right? So I shouldn’t be doing the things on Instagram that I do on YouTube. Also, like, when I thought of you talking about getting on Instagram and aimlessly scrolling, what I do that I hate is sometimes I’ll go on Instagram, scroll a little bit, and then I’ll go on Twitter and then scroll a little bit, and then I’ll go on another app, and then I’ll, before I know it, I’m just opening Instagram again. Has anyone ever done that? Right? But it’s like, in real world, I wouldn’t just go to different people’s houses without saying anything to them, right? And just leave and then go somewhere else. So I think it’s just helpful to think about these things almost as like real places in the real world. And that’ll just help you set the guideline. The real thing I want to say about creating a better relationship to the digital is, get off it sometimes. Right? I’m learning even more about just like, yo, I need a couple of days every quarter to not look at any screens. And usually when I come out of those moments, like I actually just did last week when I was in the jungles of Puerto Rico. When I get to come back to the platforms, I have so much more that I want to share and contribute. Sometimes I think it’s just stimuli fatigue, right? That really gets us in a tough head space and a mental health space even. So, remind yourself that you can have a different relationship to the tool by just putting it down sometimes too.

Alex Hillman: The algorithms make it hard. But maybe again, maybe this is just me being old school, but like, if someone’s making you feel bad, unfollow them. Like I follow people because they bring me something. Value, humor, joy, weirdness, inspiration. The internet is full of so many amazing things, and so many horrible things. And no place on earth have those two things, being pixels away from each other so often. And like, the thing we forget is that we have the power to unfollow or mute or block, and it doesn’t need to be personal. Like, I unfollow people who I love in person, because I cannot stand the way they interact with the internet, and that… I’m not here to change what they’re doing, I would like them to change for their health. But for me, I’m getting nothing, and I want to go on the internet and have a good time. And you can, the algorithms make it hard, and more and more algorithms make it harder. But I don’t know, find your weird, fun, joyful, curious corner of the internet, and, like, spend more time there when you feel that urge to pick a fight or pop popcorn, watch some other people fight. Realize that that’s them siphoning, not just money, but emotional goodness from you. And you can choose. You don’t have to leave the platform in order to leave that experience, and sometimes that’s hard to remember. But, I still believe, because I grew up on the internet, like internet communities have always been a part of my life. The idea of leaving a place, because some people showed up, doesn’t sit right with me. I’m just going to go to the other side of the room, hang out with my friends, and have a louder, more fun, joyful conversation, and invite everybody else over to our conversation. Because odds are, if you feel that way, you’re not the only one.

Helen Horstmann-Allen: We hope that this episode has left you feeling inspired to build community around your own projects, both on and offline. I love Philly Tech Week, and we’ve participated in it, both on and offline. And this year we’re back to fully in person, and it’s been terrific to get to engage with people out in the real world, out in the sunshine, out in conference rooms, and around tables, and looking out over the skyline.

Haley Hnatuk: I had a great time tabling at NET/WORK. It was so nice to chat with many of the 400 attendees about Fastmail, our values, our podcast, and our job openings. If anyone listening to this podcast thinks that they would be a good fit for the Fastmail team, you can check out our job openings by going to

Helen Horstmann-Allen: It’s a great reminder that no matter how much time we spend online, we are also always part of our local communities, our online communities, our communities of interest. And, I think this was a really important episode that really ties a lot of that stuff together. So let’s talk a little bit more about the event we hosted. Haley, what do you think the key takeaways of conversation today were?

Haley Hnatuk: Well, as Will said, it’s important to add value to the spaces you inhabit, whether they’re on or offline. In online spaces, this could be as easy as sharing an event that you think that people you are connected with might enjoy attending, or commenting on somebody’s LinkedIn post. As Michelle said, in the event planning world, simplicity makes participation accessible. So, something as easy as encouraging people to participate in thematic name tags, or if you are online, thematic zoom screen names, can spark meaningful conversation. And finally, as Alex said, when it comes to community building, onboarding is forever. So, be intentional about the type of community you want to build and start laying that groundwork early on to help foster its growth.

Helen Horstmann-Allen: We hope you can take these actionable steps towards better digital citizenship. See you next season for more conversations about how to live your best digital life.

Haley Hnatuk: Thank you for listening to Digital Citizen. Digital Citizen is produced by Fastmail, the EMO provider of choice for savvy digital citizens everywhere. Our show is produced by me, Haley Hnatuk. This episode of Digital Citizen was hosted by Fastmail COO, Helen Horstmann-Allen. Special thanks to the incredible team of people behind Fastmail, and the team of people from REC Philly, who helped us capture the incredible outdoor audio of this panel. You can subscribe to our show on any of your favorite podcast players. For a free one-month trial of Fastmail, you can go to And for more episodes, transcripts, and my takeaways or Rik’s takeaways, you can go to