Episode 6

Published on:

2nd Oct 2023

Fostering Genuine Connections for a Thriving Community with Emily Thompson

We're thrilled to welcome a true powerhouse of online community building, Emily Thompson, onto Make it Kickass. As the co-founder and host of Being Boss and the CEO of Almanac Supply Company, Emily has mastered the art of taking online connections into the tangible world. Join us as we journey with Emily, from her first real-world vacation with her audience in New Orleans to the wealth of lessons learned from hosting events.

Guest Bio

Emily Thompson is the co-founder and host of Being Boss, a resource, community, and podcast for creative entrepreneurs with over 12 million downloads, and founder and CEO of Almanac Supply Co., a retail brand that makes and curates products that help people connect with nature. For over a decade Emily has worked closely with creatives to help them make money doing work they love, with a focus on building online business models and growing creative businesses. She’s also the co-author of Being Boss: Take Control of Your Work and Live Life on Your Own Terms.

Find Being Boss wherever you listen to podcasts.

Key Topics and Takeaways

0:12:08 - Lessons Learned From Hosting Events

The ups and downs of hosting events and how they can help you understand the impact of your content and business.

0:17:42 - The difference between an audience and a community

We discuss Emily's definition of a community and how to build a sustainable, real community.

0:21:50 - When and how to us in-person events vs. online events

Emily underscores the value of both online and offline interactions, highlighting their unique strengths and how they can complement each other in building meaningful relationships and communities.

Want to dive deeper? Take our free 30 minute training, Community Event Mastery. Access it here.

Additional Resources

Next episode: Cultivating Communities that Work

This podcast uses the following third-party services for analysis:

Chartable - https://chartable.com/privacy

Welcome to Make it Kick Ass, where we help leaders of growing communities bring their people together with purpose and lasting impact. Join us as we explore how to make events engaging, exciting, energizing and profitable so that you can build a healthy, sustainable community. I'm Isaac Watson, founder and lead strategist at Kick Ass Conferences.


And I'm Nessa Jimenez, operations Manager, at Kick Ass Conferences.


Now let's make it kick ass together. Hey everyone, welcome back to today's episode of Make it Kick Ass. We are so excited to have Emily Thompson joining us today. Emily Thompson is the co-founder and host of being Boss, a resource community and podcast for creative entrepreneurs. The podcast has over 12 million downloads. Maybe even more now, you never know. They just keep going. But on top of that, she's the founder and CEO of Almanac Supply Company, a retail brand in Chattanooga, tennessee Chattanooga, tennessee, I don't know how to say it properly with a Southern accent but a retail brand that makes and curates products that help people connect with nature. I met Emily at Podcast Movement in Las Vegas earlier this year after I was a long time listener of the podcast and happened to grab her with a question after a session, and we became fast friends. Emily, welcome to Make it Kick Ass. We're happy to have you here.


Thank you for having me and Isaac and Nessa. I am very excited about this chat and, speaking of chat, it is Chattanooga. We do say the T's, which is always a funny thing hearing people say Chattanooga without saying the T's. We say them. So good job the first time.


All right, thanks. Obviously, I've never been there, nor am I from there.


No, we do say things quite slowly here, but I'm very excited about this chat for sure. Awesome.


Well, what we want to start with is, well, your community being boss, you've took that community from being online and you brought it into the real world by hosting in-person events, so we want to know a little bit more about how that came about and what that process is like for you.


Yeah, I mean we started okay, I'm going to say we a lot, and I say this because whenever I started being boss, I started it with a co-host, so it was me and myself, kathleen, so it is a very real we and not a weird we, whatever I say that. So we started being boss in 2015 as a way to just share our experiences of being online creative business owners with the world, because we found our own conversations that we'd been having for years together to be so helpful. We had met in the blogging world back when blogging was a big thing. We met in comments and just sort of hit up a nice little friendship where we were meeting on Skype back in the day at least once a month or so to sort of talk about business together between the two of us. And we decided to start the podcast as a way to sort of share those conversations with others, because we thought that if we were finding them useful, then other people would find them useful as well. And we started this in a time when no one was talking to creative entrepreneurs. There were not business blogs that were really creating this sort of environment, especially of content, where they're sharing how to get clients and grow your brand and even, to some level, do social media marketing. We were very early in that space, and so we started this show as a way to share those conversations and hoping that our people and by our people I mean I was running a web design agency where I was working with creative entrepreneurs, and she was partnering with her sister on a branding agency where they were doing branding for creative entrepreneurs so we were already working with our people and we wanted to give them just a little bit of extra support, a little bit of extra insight and like just this feeling of you're not in this alone, which is something that creative entrepreneurs or online entrepreneurs, small business owners feel often.

And so we started the show in:

And Kathleen and I had this idea that we wanted to do a vacation, the two of us who wanted to travel together. We were living in different states at the time and it only been together in person a couple of times. We wanted to get together, do something together, and we're like what would it look like if we were just to, you know, invite our audience to come on this quote unquote vacation with us? And this was a couple months after starting the podcast, maybe four or five months. We hosted the vacation about 10 months after starting the show and that's really where it all started. So it was really from a place of we want to meet the people that we already have been building relationships with. They were our clients. We would love the opportunity to meet the kinds of people who are engaging in our podcast content, so people who are on Instagram or Twitter or in our newsletter, who are listening to the show and sending us feedback and it looks like us going on vacation together.

We went to New Orleans and it was a great time. So it was a very natural evolution of we're online, we should go offline. It was a very fast evolution. It happened over the course of just a couple of months and this wasn't in the time where that was the tactic right, like no one was telling us that the next step of this thing is to take it offline or to do this next thing. We were just sort of trusting our gut and doing the thing and we did it and it began what really was the beginning of the business model. That was being boss. Because being boss started as just a passion project that the two of us were doing as sort of a marketing arm for individual sort of creative agencies, and at that point being boss started making its own money for real and it turned into a company where a portion of its revenue every year was events where we were getting our audience together, building this community in these sort of real life settings, and we loved it. We absolutely loved doing it.


That's amazing, especially since at the time you were doing that like you're right, like now I think there's more of a tactic. Like I know there are podcasters that do tours, right, and they sell tickets to their tours. There's even like podcast groups that they do cruises and stuff, like that's the thing now, but at the time you're doing that like it really was, like nobody was doing that. That's amazing.


Yeah, no one. I mean, sophie, people had a podcast. At that point it was 2015. This is the time when everyone was listening to serial and invisibility. Like that was that era of podcasts, right, like that's the only podcast really anyone knew up and but everyone was listening to them. So it was that era and at the time we were also the only two. We were only like podcast. That was to women in business in the top charts. Like it was like some very early days of podcasting and so, yeah, it was before anyone was doing those sorts of things.

We were doing live podcasts. We did a live podcast at that first vacation. We were probably some of the first people who were doing that. So we just very intuitively ended up doing this thing. That has become the tactic for growing an audience. I don't think we, like you know, intentionally like pave the way or anything, but there is something to be said about this process for doing it. If we were doing it without thinking about the strategy of it and now everyone recognizes that that's the strategy of it I think that's that's some powerful stuff and I'm glad that we were able to do it in the time that we did it with the people that we were doing. Doing it with, I did some of the best things I've ever done in business, for sure.


And what about like? Can you tell me about the first, those first people that participated in those first events Like why? Because, obviously, like, you decided to give it a shot but not knowing, like, are people going to show up. So those people that did like, how did they receive that? What was the kind of feedback you were getting from them?


Oh, they loved it, they loved it, we loved it and it was. It was some of those clients that we had known for years and had just never had the opportunity to meet in person. So there was like a core group of those folks. But there were also people that we had never met before, we had never like talked to, they had never really replied. They just wanted to come meet up with people who were like minded.

I think I think the, the small creed of business sort of audience or market, is sort of primed for that kind of interaction. They are working alone, they're, you know, tired by themselves and just want to go have fun with people who get them right. And so we were working in an audience that was already primed for that kind of thing and they just showed up ready to sort of meet each other and engage and talk about business, because they couldn't talk about business with their partners or their friends. I remember one boss in particular from that trip had just had her second or third baby. This was her first trip and she spent her whole time other than like the, the organized things like in her room. Sleeping, like that was like her getaway for herself. That was a business write off and I loved that for her.


Right, so a lot of people right.


A lot of people came with sort of their own agendas like that, but really they were there to to meet each other. Many of them had been friends on Instagram, like they had met in our comments or whatever, and they were sort of building their own little relationships. And so there were like these pockets of people, too, who were coming to meet each other, like they had all signed up together to come to this thing together to finally meet in person, you know for themselves, for the first time as a part also of this larger group. So they were just our people. They were like us in so many ways and they just wanted to get out from behind the screen and get together and talk about business and have fun in a place that was inspiring and folks really loved it. Many of them came back to vacations again and again We've had we have a couple of people who have been to every single event we've ever hosted.

Like there are. There's that core group of people as well. When you really get to doing it and you really tap into what it is that people really want out of these kinds of things, they'll go anywhere, you ask.


Yeah. So I'm curious having started doing events very organically, right and kind of stemming from this isolated, creative business owner mindset and wanting to collect people together, you host this first vacation. What were the big Uh, what were the big lessons you learned? Like there was clearly little to no strategy involved other than we're going on a vacation. Do y'all want to come? How did that? What did you learn from that and how did that inform the other events that you hosted or what you did with the podcast going forward?


Sure learned so many things in that first event. That first event was a, you know I'm going to call it like a two day situation. I think there was an evening cocktail hour. I'm trying to remember exactly what that first one was. There was an evening cocktail hour first night. I think we bought everyone two drinks or something like that. That one also might have been Dutch, I know. Later we ended up doing drink tickets. We did an open bar once. Never do. That was a lesson learned Right there. Let me tell you, do not recommend Was some like lonely need to get out more online business. That was a hoot. So we did a cocktail hour first night.

Next day, I believe was a live podcast recording in like a quote unquote masterclass where we just sort of guided them through some sort of exercise. We did dinner, I think, that night, and by that I think we just organized sort of I think it was like 10 top tables at a couple of restaurants. We did it in New Orleans. So we got in touch with a couple of restaurants and did 10 tops in those and I think everyone went Dutch for that, if I'm not mistaken. But maybe actually we did pay for that. I don't remember, and then we did a ghost tour. So we arranged a ghost tour in the city and going somewhere like New Orleans, that one was really big for us. We learned very much. So a city like that sells itself and a lot of ways like people just want to go and they'll kind of take any excuse they can to get there. We also learned some lessons in that. In itself it's called the big easy for a reason. It's not a very easy place to host events for sure.

Yes, we had really big problems with the hotel for that, and we had bosses because we call her audience bosses. We had bosses come to check in and the hotel had given their rooms away oh my God, because the saints were staying that night and they needed the rooms, which was quite a hot mess. So we had bosses sleeping on the couches of other bosses rooms that first night, which was just like a wild and incredibly angering situation, but also kind of literally nothing we could have done about it. So learned a lesson not to work with that hotel chain ever again. Right, so like fun little things like that we also. We learned in that first one as well. We had intentionally gone.

What's it called Like content light, like we really or programming light. We wanted to feel like a vacation, wanted people to have plenty of time to wander the city and do their own things, but bosses really wanted more and they really wanted some facilitated conversation time. A lot of online business owners are introverts I thought it was just me, but apparently it was a little more rampant that I thought and so they needed a little bit more help, sort of finding their people and getting conversations struck, which, and all of those things took us into the next couple of vacations that we did. We ended up doing more facilitated round table discussions. We did similar dinners, because everyone really loved that. We kept the live podcast recording.

We made it very intentional to do more like culture, culture related things when we were all getting together, no matter where we were, because that was really important to me but also to the attendees.

So there was lots of things that we learned along the way and in terms of you know how that really played into the podcast. I honestly don't think that there was anything that really changed in how it was we were podcasting. It really just continued. It helped us find more meaning and really understand the impact that we were having in the show. So not so much changing the strategy, but was just like a fire under our asses to keep doing it. Because when you are podcasting, you're also sitting here alone, maybe with a co-host or a guest right, not really understanding the impact that you're having, until you're sitting in a room with bosses or sitting at a table or your audience they're my bosses, it's your audience. When you're sitting at a table with your audience, having those conversations or listening to them talk to each other or whatever it may be. That's the moment when you understand your impact and it fuels you to keep doing the thing.


I think that's really key is like the events really do give you the ability to validate what the rest of the content that you're putting out there, or the business there or the community that you're building it.

In a lot of ways, especially with the vacations where you had a fairly small group of these people gathered together they serve kind of as a focus group right, like not not in a very structured way, but like you can Really pull a lot of anecdotal, qualitative information about what their needs are, what their goals are and how you can better serve those in the future. I think that's great. I want to shift gears a little bit. When you and I first met earlier this year, we bonded over how we actually define community, and community is a major focus of this season of the podcast. So I'd love to just hear for you I mean, we we Are have kind of gone on this tirade about you know your community is is not an audience, a community, something different? What? What does true community mean to you in the context of what you built with being boss and what you see other people building in a in a more Sustainable way?


Yeah or real, just real way, right? Yes, we bonded specifically over. I think we had both been in a couple of sessions where we had heard people talking about quote-unquote Community and aspects of what they're really talking about with their audience, right?

Like, if you are a podcaster or or anything, if you are putting out any kind of content into the you know Internets, then you are talking to an audience is a one-way street and that is, that is your audience. That's not your community. Community is where you are fostering Connections between them, not just them with you or you with them. Right, it's like it's actually, I guess that is kind of a two-way street. Community becomes like a infinite way street. Who are we? Where it's completely open for everyone to connect with each other? And I think, or that misdefinition is, I think, one of the most toxic things of the internet. That's a lie. There are so many more toxic things, but in our space, that not recognizing what true community is, I think does a disservice to all kinds of things that we're trying to do, and so for me, it really is about opening the doors and allowing people to connect with each other and Me not being the gatekeeper to their connections, right? So you know, if you have, if you have a patreon or if you are just you know, and even to some extent, in Instagram comments or like, wherever it is that you're sort of Facilitating quote-unquote community online. That's really just you engaging with your audience in vice versa, and, sure, maybe they're connecting and maybe they're going into, you know, dms on their own or whatever and that community sort of happening. That's happening outside of what you're doing. You're not really fostering that. That's how Instagram is fostering that, right. But whenever you do something like Open up a genuine community space online or do events like this, we are getting everyone together and you're giving them free time to connect with each other. You're not standing on the stage just talking at them the entire time, right, but you're facilitating these, these moments where they can be sitting at dinner or, you know, doing a ghost tour or hanging out at a yacht, because we've done that before. Like you. You're creating these moments when you're allowing people to connect with each other. That's when you're fostering community.

And then it grows outside of yourself, and that's a point that is scary, is terrifying, actually, to think about how your community is going to grow once it sort of leaves your hand.

That's also where the magic happens, and so I think true community is organic. It's not super contrived or controlled in any way, like you can't control it. That's kind of the beauty of it, as well as the terrifying part of it, is about Opening up their connections to to talk to each other and do things together in it really to have literally nothing to do with you. It's more about the ethos that you have brought to the table right them connecting under that ethos and them going and doing whatever it is that they want to do, regardless of who you are or what you're doing, and that it goes against the ego drive of so many like online Folks who are trying to quote-unquote build community. But it is the thing you have to put behind in order to truly grow community, and it morphs and grows in a way that is both beautiful and out of your control and creates Incredible, incredible impact for them, outside of anything that you could facilitate on your own.


What I'm hearing you say with that and correct me if I'm wrong, but what I'm hearing you say with that is more like the, the, the social media and the events are are more the tools than the actual thing, right?


Absolutely like.


so then, related to that, then what, what? What does do events versus the online aspect? What do each of these allow you to do that the other doesn't like? What? What? Why? Events for some things versus Online for other things?


Yeah, oh, that's. That's a big question Really, but a good one and I think I think it's important to think about. I was reflecting on this little bit before we got on the call. I think one of the reasons why it was so easy for me to step into online is because I'm of a age where I didn't grow up on the internet in no-transcript. I think people do now. You know, I was on the internet at, you know, 14, 15, 16, but it was a very different world back then. So I remember, I remember what it's like to sort of build connections in that way and I remember, like why it's so important. But I also am very much so ingrained in the online world. I also know how that works. It was the one day, I think, all of my friends I met online, even my partner, even though we went to school together. Our first conversations happened on AOL Instant Messenger.

You know, like, oh, so like, I'm also very much so part of the online world, but so I understand the difference, though, between the two and the power of both of them. I think online, sort of you know, breaks all boundaries of geography, which is incredibly important when trying to find your people. Kathleen and I, when we started the podcast, we were living hundreds of miles apart. We could not have done it without the internet, and I'm friends with people all over the world. I have met bosses, online and offline later, who have lived all over the world.

I could never do that if I was just trying to build community in the offline space. So for me it is a great first step. It could also be a second step, but I also think it's a great first step for connecting, for getting it started and also for having a bit more quote, unquote, control and what is like parameters and structure, I guess for building the community, sharing your ethos, finding your people. I think it's a very powerful tool for that. Offline goes deeper, which is why I think it's a great second step. It could be the first step, but I think it makes a really great second step after online, because it helps you take those connections that you've made on the internet and take them incredibly deeper, right? You're doing this through shared experiences. I have special connections with people who I danced on that yacht with in Miami right, or that I stomped through the streets of New Orleans in a parade in a whole ass glitter jumpsuit right.

Like those moments are going to be carried throughout not only my life but all of our lives. We will always have those experiences together. We're gonna remember that one time that Elon took over Twitter online. Like that's not quite the same thing, right. Whenever you're sharing those online experiences or visiting places together or having those real world conversations, you can sit in people's aura right. You can hear their true inflections. You can see their 3D body in its fullness.

There is some really great things that come offline that you cannot accomplish, or it happens offline that you cannot accomplish online, and so I think pairing the two of them are incredibly important. But I also think you're really right they're just tools. They're tools that allow you to make the connections one way or the other, and it's funny. I do have a funny little story of how this even didn't even work in well. Maybe it did work in our favor in their long run. But I had a friend that I had met online. We were co-working together and for a couple of years, and we finally decided to go to a conference together and we stayed in a room together and we actually realized we didn't like each other very much.

Like once we were in the room together like oh, I have co-worked with you almost every day for like three years and now that we're in the same room together like this actually isn't vibing right and that is much less frequent, but it just sort of illustrates this difference between being offline with someone and being online with someone.

It is a different connection and I think when you can be cool in both right, when you can connect truly in both, that's when real relationships happen, and not just me with my audience, but between them as well. I have watched people get together and start start their own masterminds together that have gone on for years, Start businesses together, because I'll never forget the pair that met in the elevator at our book launch party in New York City. They emailed us a year later and they started a business together because they met in the elevator. If they had just been like passing on Instagram comments probably wouldn't have happened but, because they had that shared moment together.

in physical space, it equated to something way more real and I love that.


Do you think that it's harder to like? You know, we talk, especially in the Instagram world, about this kind of projection of perfection and you know aesthetic, whatnot. Do you think it's actually harder to project that kind of stuff in person? It's harder to be inauthentic as a human when you're in person with someone else.


Absolutely, absolutely. I'm thinking of a couple of assholes that I've met along the way that, like online cool enough. In person I could really not. With you For sure, you can absolutely polish things up, edit things up, say what you want like, and not show the sort of not show any other side that you don't want to show. But you know, if you're in person, let's see how everyone reacts whenever the hotel gives your room away.

Yeah, right, or when you're hangry because that walk went longer than everyone thought and you need to get some food, and so, yes, absolutely, you can really see a true person, so much more so in person than you can online. Hands down.


That's the whole reason that trolls exist online and don't really exist in person, right, because we see right through them. I will say that I am very glad that Nessa and I, after having worked together online only for what did we decide six years finally met in person last year, and we didn't hate each other and you're both still here, congratulations.


Thank God, imagine if, like we met, we were like oh no, I don't know about this one, it is the true test.


It is the true test and I will say I did share, like all the awful people that I've met along the way, because I have and it's funny the people that people will pay and just like worship in some spheres and in person, no, thank you. But I've also met more people who in person, really are like, are better than what they portray online, like they're truer, they're more joyful, you can really feel it in a way that you can't really feel online. So it goes both ways. It's not just you can be more awful, but you can really also be truly better in person in a way that people are missing out on if you always keep it offline.


That's true. So our bonding and opinions about community and insistence that community should be built correctly led us to actually pitch and present a session at Podcast Moving in Denver in August about how to what we call it Community 201. Beyond audience building, and I think what really stood out for me is we were prepping that session together, both in hearing you share some of the same experiences that you shared with us today, but in talking about how integral community is to the work that we do. What are some of the like biggest takeaways that came out of that process for you as you think about how other people like it's one thing to think about how your community grew organically it's a single example. What are some takeaways that you think people should have as they listen to this and as they think about how they can build their community in a more real and authentic way going forward?


Great question. The first thing that pops up is really this altruism, right Like this, really wanting to build community for them, not for you. If you build an audience, you're doing that for yourself, and I love that. Like that is the game and there's nothing wrong with that game. Go for it. But the moment your goal is to build community, you're doing it for them, not yourself, and I think that's really important to consider, and you will get benefits for sure, especially if you're doing it. Well, you know all the things, but the community is really for them, and I think that's probably a hard pill for a lot of people to swallow. But whenever Kathleen and I started it, like it really came from this altruistic place of if we've benefited so much from our own community between ourselves, and how can we replicate that for everyone else who needs it and it became this big, beautiful thing.

w if you mentioned it, but in:

I think if you do it right, I think, if you and you're bringing great people around you and I think the energy of the altruism as well, is just going to naturally attract some really great people these people will follow you anywhere and not like a weird culty way. But I also think sometimes they probably could Like I probably could have started a cult along the way. But you know there are bosses that have gone on every trip that we've ever done, like they are just down to have a good time and you know they want to meet everyone as well. But also, as I have transitioned out of being boss because I did record my last episode of being boss and it went out in June of this year as I have made that transition out like they are one I still mastermindings, so they're still like there still is a core community, but then we're also like they're following me into Almanac, they're buying crystals and candles and client gifting, like they're doing all of those things.

Because when you have a community that is so invested in like a genuine way, like these people are my friends, like I also want to make that really clear as well.

When I say quote unquote community, I mean my pals, like my friends that I have, like had dinner with and drinks when I'm traveling. These are the people that I message and you see if we can meet up, like there's lots of them and I love that. But they'll follow you also as you go through your journey as well, into the next thing, and I think like that's nurturing long term relationships that I think on some level, we've kind of forgotten how to do as people living in the modern world, especially in America. But if you do it well, these are relationships that become incredibly important to you. Most of my dearest friends are bosses that I have met along the way. One of my very best friends is someone who went on our second vacation and has been on every vacation since, and now we are literally texting Marco Poloing every single day. These are the kinds of relationships that you build, but it does come from a truly altruistic place that supports what you do, but you're also supporting them and allowing them to support each other.


Thanks for listening to this episode of Make it Kick Ass. We hope you found it entertaining and helpful. If hosting a community event is on your radar, visit GetEventLab.com to take our free 30-minute training called Community Event Mastery. That's GetEventLab.com, or use the link in the show notes. Make it Kick Ass is hosted by Isaac Watson and Nessa Jimenez. Post-production audio by Chris Nelson at Mittens Media. Our theme song is Feel it by Dojo for Crooks. Make it Kick Ass is a production of Kick Ass Conferences, an event strategy and design agency serving leaders of growing communities.

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About the Podcast

Make It Kickass
Community Event Mastery
Make It Kickass explores how leaders of growing communities can make conferences with impact, gatherings with purpose, and an attendee experience that knocks their socks off. We uncover the strategies, tactics, and tools we use every day to bring our clients’ conferences to life. If you've ever wanted to host a life-changing conference, this podcast is for you.

Find us at kickassconf.com or geteventlab.com

About your host

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Isaac Watson

Isaac Watson is the founder and Executive Producer at Kickass Conferences, an event strategy and production studio based in the Pacific Northwest. Isaac helps community leaders develop and deliver transformative events for their audiences and inspire them to build a better world.

A maker and introvert at heart, when he’s not working his magic behind the scenes in event strategy and production, he’s usually at home in Vancouver, Washington working on remodeling projects, gardening, cooking, learning to sew, and building LEGO.