Creating Connections: The Journey of Being Boss from Podcast to Community Hub
Emily Thompson, a powerhouse in the realm of creative entrepreneurship, has the hands on experience of moving her online audience into a community connected in the real world. As the co-founder and host of Being Boss, Emily spearheaded a community and podcast that boasts over 12 million downloads. With over a decade of experience, Emily has been on the forefront of empowering creatives to monetize their passions and build sustainable online business models.
In this interview, we delve into Emily's experiences and advice for creatives looking to take their online communities to the next level and foster deeper relationships. We discuss how Being Boss went from a podcast to a strong community that still lives on despite the podcast ending last year.
Tell us a little bit about the history of Being Boss.
When I started Being Boss, I started it with a co-host, so it was myself and Kathleen. We started Being Boss in 2015 as a way to share our experiences of being online creative business owners with the world. We had met in the blogging world back when blogging was a big thing. We met in the comments and struck up a nice little friendship. We were meeting on Skype at least once a month or so to talk about business together.
We decided to start the podcast as a way to share our conversations with others because we thought that if we were finding them useful, then other people would find them useful as well. We started this at a time when no one was talking to creative entrepreneurs. There were no business blogs that were creating this sort of content, where they were sharing how to get clients and grow your brand or 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 we wanted to give our people just a little bit of extra support, a little bit of extra insight, and this feeling of you're not in this alone. This is something that creative entrepreneurs, online entrepreneurs, and small business owners feel often.
How did you transition your online community into the real world? What was the process like for you as the community leader?
Kathleen and I had this idea that we wanted to do a vacation. The two of us wanted to travel together. We were living in different states at the time and we had only been together in person a couple of times. We wanted to get together and do something together, and we thought, what would it look like if we were just to invite our audience to come on this “vacation” with us?
This was a couple of 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. It was really from a place of wanting to meet the people that we already had been building relationships with. They were our clients. We loved the opportunity to meet the kinds of people who were engaging in our podcast content, such as people who were on Instagram or Twitter or on our newsletter who were listening to the show and sending us feedback and it looked like we were going on a vacation together.
We went to New Orleans and it was a great time. It was a very natural evolution from online to going offline. It was a very fast evolution. It happened over a couple of months. This wasn't at a time when that was the tactic. No one was telling us that the next step of this thing was to take it offline or to do this next thing. We were trusting our guts and doing the thing and we did it and it turned out to be the beginning of the business model. That was Being Boss.
Being Boss started as a passion project that the two of us were doing as a marketing arm for our 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 real-life settings, and we loved it. We loved doing it.
We did a live podcast on that first vacation. We were probably some of the first people to do that. we just very intuitively ended up doing this thing that has become the tactic for growing an audience. I don't think we intentionally paved the way or anything, but there is something to be said about this process. If we were doing it without thinking about the strategy of it and now everyone recognizes that that's the strategy I think that's some powerful stuff. I'm glad we were able to do it in the time that we did it with the people that we were doing it with. I did some of the best things I've ever done in business, for sure.
What were those first participants like? What motivated them to join and, how did they react to the experience?
Oh, they loved it, we loved it and 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 a core group of those folks. But there were also people that we had never met before, we had never talked to. They just wanted to meet up with like-minded people.
I think the small business audience or market is primed for that kind of interaction. They are working alone, they're tired by themselves and just want to go have fun with people who get them. We were working with an audience that was already primed for that kind of thing and they just showed up ready to meet each other and engage and talk about business. 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 outside of the organized things in her room sleeping. That was her getaway for herself. That was a business write off and I loved that for her.
A lot of people came with their own agendas like that but they were really there to meet each other. Many of them had been friends on Instagram. They had met in our comments and they were building their little relationships. There were these pockets of people who were coming to meet each other. They had all signed up together to finally meet in person for the first time as a part of this larger group. 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 loved it.
Many of them came back on vacations again and again. We've had a couple of people who have been to every single event we've ever hosted. When you really get to do it and you tap into what it is that people really want out of these kinds of things, they'll go anywhere you ask.
Given the lack of initial strategy beyond the invitation to join a vacation, how did the outcome of that first year shape your approach to future events or influence your podcast moving forward?
We learned so many things in that first event. That first event was a two-day situation. There was an evening cocktail hour. I think we bought everyone two drinks or something like that. In later years we ended up doing drink tickets. We also did an open bar once. Never do that. That was a lesson learned right there. Let me tell you, I do not recommend it.
The next day, I believe, was a live podcast recording and a type of masterclass where we guided them through some sort of exercise. We did dinner, and by that, I think we just organized 10 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 in those and I think everyone went Dutch for that, if I'm not mistaken.
Then we did a ghost tour. So we arranged a ghost tour in the city and when you’re somewhere like New Orleans, a city like that sells itself. A lot of people just want to go and they'll take any excuse they can to get there. We also learned some lessons from that. It's called the big easy for a reason. It's not a very easy place to host events for sure.
We had really big problems with the hotel and we had Bosses (because we call our audience Bosses) come to check in and the hotel had given their rooms away because the Saints were staying that night and they needed the rooms.
So we had Bosses sleeping on the couches of other Bosses' rooms that first night, which was just a wild and incredibly angering situation, but nothing we could have done about it. So I learned a lesson not to work with that hotel chain ever again.
In that first one, we had intentionally gone content light or programming light. We wanted it to feel like a vacation and wanted people to have plenty of time to wander the city and do their own things. But Bosses wanted more and they wanted some facilitated conversation time. A lot of online business owners are introverts. I thought it was just me, but it was a little more rampant than I thought.
So they needed a little bit more help, finding their people and striking up a conversation which, we took into the next couple of vacations that we did. We ended up doing more facilitated round table discussions. We did similar dinners, because everyone loved that. We kept the live podcast recording. We made it very intentional to do more cultural things when we were all getting together, no matter where we were, because that was important to me but also to the attendees.
There were lots of things that we learned along the way and in terms of the podcast, I honestly don't think that there was anything that changed in how we were podcasting. It just continued. It helped us find more meaning and understand the impact that we were having in the show. So not so much changing the strategy but was 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, not understanding the impact that you're having until you're sitting in a room with 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.
When we first met, we discussed how we define community, which is a major focus of our work this year. What does true community mean to you, especially in the context of Being Boss and in observing sustainable community-building efforts elsewhere?
If you are a podcaster or anything, if you are putting out any kind of content on the Internet, talking to an audience is a one-way street. 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. Community becomes an infinite-way street. And I think that misdefinition is one of the most toxic things on the internet. There are so many more toxic things, but in our space, not recognizing what true community is, does a disservice to all kinds of things that we're trying to do.
For me, it is about opening the doors and allowing people to connect and not being the gatekeeper to their connections. If you have a Patreon or if you are even to some extent in Instagram comments or wherever it is that you're facilitating “community” online. That's just you engaging with your audience and vice versa.
Sure, maybe they're connecting and maybe they're going into DMs on their own but that's happening outside of what you're doing. You're not really fostering that. That's how Instagram is fostering that.
Whenever you do something like open up a genuine community space online or do events where you're getting everyone together and giving them free time to connect, you're not standing on the stage just talking at them the entire time, you're facilitating these moments where they can be sitting at dinner or doing a ghost tour or hanging out at a yacht. You're creating these moments where you're allowing people to connect. That's when you're fostering a community.
And then it grows outside of yourself, and that's a scary point, it’s terrifying actually to think about how your community is going to grow once it leaves your hands.
That's also where the magic happens. True community is organic. It's not super contrived or controlled in any way, you can't control it. That's kind of the beauty of it, as well as the terrifying part of it, opening up their connections to talk to each other and do things together that have nothing to do with you.
It's more about the ethos that you have brought to the table. Connecting under that ethos and then them going and doing whatever it is that they want to do, regardless of who you are or what you're doing. That goes against the ego drive of so many online folks who are trying to “build community”. But it is the thing you have to put behind to truly grow a community, and it morphs and grows in a way that is both beautiful and out of your control and creates an incredible impact for them, outside of anything that you could facilitate on your own.
What advantages do events offer compared to the online world, and vice versa? In what ways do events excel where online platforms may fall short?
That's a big question but a good one. and I think it's important to think about it. I was reflecting on this a little bit before we got on the call. I think one of the reasons why it was so easy for me to step online is because I'm of an age where I didn't grow up on the internet in the way I think people do now.
I was on the internet at 14, maybe 15, but it was a very different world back then. I remember what it's like to build connections before the internet and I remember why it's so important. At the same time, I’m also very much so ingrained in the online world. I also know how that works. 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.
I'm very much part of the online world, but I understand the difference between the two and the power of both of them. I think online 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 it's a great first step for connecting and for getting it started. For having a bit more “control” in terms of parameters and structure for building the community, sharing your ethos, and finding your people. 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 great second step after online because it helps you take those connections that you've made on the internet and take them much deeper. You're doing this through shared experiences. I have special connections with people with whom I danced on that yacht in Miami or I stomped through the streets of New Orleans in a parade in a whole-ass glitter jumpsuit.
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 not gonna remember that one time that Elon took over Twitter. That's not quite the same thing. Whenever you're sharing those online experiences or visiting places together or having those real-world conversations, you can sit in people's aura. You can hear their true inflections. You can see their 3D body in its fullness.
Some great things happen offline that you cannot accomplish online and vice versa. Pairing the two of them is incredibly important, but they're just tools. They're tools that allow you to make the connections one way or the other.
I do have a funny little story of how this didn't work well. Maybe it did work in our favor in the long run. But I had a friend that I met online. We were co-working together for a couple of years, and we finally decided to go to a conference together and we stayed in a room together and we realized we didn't like each other very much.
Once we were in the room together like oh, I have co-worked with you almost every day for three years, and now that we're in the same room together this isn't vibing. 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 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 their own masterminds that have gone on for years, and start businesses together. 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 passing on Instagram comments this 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.
Is it harder to maintain an image, I’m thinking particularly of the Instagram “polish”, during in-person interactions compared to online. Is it harder to get away with being inauthentic when engaging face-to-face with others?
Absolutely. I'm thinking of a couple of assholes that I've met along the way that online are cool, but in person, I could not [deal with them]. For sure you can polish things up online, edit things up, say what you want, and not show any other side that you don't want to show. But if you're in person, let's see how everyone reacts whenever the hotel gives your room away or when you're hangry because that walk went longer than everyone thought and you need to get some food. So, yes, absolutely, you can really see a true person so much more so in person than you can online, hands down.
But I've also met people who in person are better than what they portray online. They're truer, they're more joyful and you can feel it in a way that you can't feel online. So it goes both ways. It's not just how you can be more awful, but you can also be truly better in person in a way that people are missing out on if you always keep that offline.
So you and I recently presented a talk at Podcast Movement in Denver called Community 201: Beyond Audience Building. What did you gain from preparing and presenting the session? How do you think it can help people in building their communities more authentically and effectively?
Great question. The first thing that pops up is altruism. Wanting to build a community for them, not for you. If you build an audience, you're doing that for yourself, and I love that. 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 important to consider.
You will get benefits for sure, especially if you're doing it well. But the community is really for them, and I think that's a hard pill for a lot of people to swallow. Whenever Kathleen and I started, it came from this altruistic place. We've benefited so much from our relationship with each other, how can we replicate that for everyone else who needs it? It became this big, beautiful thing.
I think if you do it right and you're bringing great people around you and the energy of altruism, it’s just going to naturally attract some great people. These people will follow you anywhere and not in a weird culty way. Some Bosses have gone on every trip that we've ever done, they are just down to have a good time and you know they want to meet everyone as well.
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 I still do a mastermind, so there still is a core community. But then they’re also following me into Almanac, they're buying crystals and candles and client gifting, they're doing all of those things.
Because this is a community that is so invested genuinely, these people are my friends, I also want to make that clear. When I say community, I mean my pals, my friends that I have had dinner with, and drinks with when I'm traveling. These are the people that I message and see if we can meet up. There are lots of them and I love them. But they'll follow you as you go through your journey as well, into the next thing.
That's nurturing long-term relationships and on some level, we've kind of forgotten how to do that as people living in the modern world, especially in America. 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 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.