Succeed by Serving an Audience, with Emily Thompson

The Transcript

Succeed by Serving an Audience, with Emily Thompson

Emily Thompson: I’m Emily Thompson. I’m a podcaster, a digital product maker, a business coach for creatives, a rebellious overachiever, and I’m so unemployable.

Brian Clark: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one, and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs get actionable advice and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our free Profit Pillars course, or choose to sign up for the newsletter only at no charge. Simply head over to Unemployable.com and take your business and lifestyle to the next level. That’s unemployable.com.

Emily Thompson is no stranger to the independent business life. She started off with an Etsy shop and soon began helping other business people build their own platforms with web design and coaching. Emily is the founder of Indie Shopography , a design and strategy web studio where she and her team develop websites for creative entrepreneurs who want to rock their online presence, but things have shifted in a big way since she teamed up with Kathleen Shannon of Braid Creative to start the Being Boss podcast.

Yes, it’s another podcasting success story. Being Boss resonated so strongly with the creative entrepreneurs that Emily and Kathleen aimed to help, and it seems more like a movement, and it’s led to a successful membership community and an upcoming book. Listen in to hear about the commitment and work ethic that the two have applied to the Being Boss project and why that was the key to success. You’ll also hear great advice about partnering up with someone for a project like this and the criteria for ensuring that you’re not making the wrong choice.

I’m Brian Clark, and this is Unemployable, which is brought to you by the all new Freshbooks, easy accounting software for freelancers and small businesses. Sign up for an unrestricted 30-day free trial exclusively for listeners of Unemployable by heading over to Freshbooks.com/Unemployable and entering “Unemployable” in the How Did You Hear About Us section. All right. Let’s chat with Emily. Emily, how are you doing? Thanks for being here.

Emily Thompson: I’m doing great. Thank you so much for having me. I’m excited to be here to chat with you this morning.

Brian Clark: Oh, yeah. Absolutely. Of course, I spoke to your partner in crime, Kathleen. It’s been over a year though, and then of course, I was on an early Being Boss episode. Thank you for that.

Emily Thompson: Yes. Of course.

Brian Clark: I had the greatest time talking to you two. It seems like you two are just made for conversational content if that’s a way to put it.

Emily Thompson: I think so, and I agree with you. Somehow, it works. It works out really well.

Emily’s Unemployable Journey

Brian Clark: Okay, so let’s talk a little bit about how things started off for you in this great unemployable journey of yours, and then we’ll eventually catch up to that amazing podcast that you have started and are really succeeding with, and what that really means going forward, which I think is exciting to get to, but let’s find out the backstory first.

Emily Thompson: Sure. I graduated college, and within a month, I decided I had no desire whatsoever to get a job in the field that I had just earned my degree, which was geography of all things, and so I had been doing some online business stuff. I’d been making jewelry, and selling it, and helping other makers start their Etsy shops and those sorts of things. I had just taken my Etsy shop on to its own website, and I found myself playing in the code more than I was making my product and had a couple of people come to me wanting their own websites or wanted me to make them a website like I had made for myself.

About a month after graduating, I decided, “You know what? Let’s try to be a freelance web designer and just see what happens,” and these were skills that I had picked up just by playing online over the previous, I don’t know, five to 10 years or so. Within a couple of weeks, I sold my first project, and then I sold my second project, and my third project, and my fourth project.

Before I knew it, I was a freelance web designer or developer, making more money that I probably would have as an entry-level geographer. I would have been doing like map digitizing and what our professor very lovingly called being a GIS weeny, which is not something that I wanted to do with my life, so I had fallen into becoming a freelance web designer and developer, helping makers, so people who were stationers, and jewelry makers, and photographers even start websites to grow their business presence online.

I did that for a couple of years, and I loved it a whole lot. I was really diving in to some business things, which is really exciting to me. I had actually owned a business previously, a brick and mortar, a couple of years before that, so I always had this knack for business, and I had the skillset that was web design development, and I had experience because I had been running my own online business, and it all just worked together to create my web business, which is Indie Shopography. I did that for a couple of years, helping other makers and creatives start online businesses, and it was a lot of fun, and I learned a whole lot of things.

Brian Clark: That’s interesting. You were attracted immediately to product over at Etsy, right?

Emily Thompson: Yes.

Brian Clark: A lot of people, of course, start off in some sort of client business as a freelancer, what have you, consultant, and then they’re aiming to head to product, but it sounds like the fact that you started there, you injected yourself into an ecosystem wherein you were in a position to help with services. You knew these people’s businesses inside and out, and how helpful was that?

Emily Thompson: Definitely, and like I’ve always … I’m a maker. I’ve always made things. For me, it was more natural for me to do the things that I was already doing for myself, and for friends, and friend’s birthday presents, and Christmas gifts, and those sorts of things, and turning that into a business. I had a product, and I could turn it into money basically when I discovered Etsy, and this was probably, gosh, this was probably 10 years ago.

Etsy was a different place back then, and it was all very new and exciting, and it was easier to get in with that built-in traffic because Etsy was still relatively small, but even then, within a couple of months, I realized that to really make a product business work online, you needed to have your own platform. Going through someone else’s platform, those Etsy fees start killing you. Fees in any platform you’re on like that can often make you wonder if you could do this better on your own.

Yeah. I knew these people’s businesses, which definitely gave me some really good clout in terms of knowing how it was that I was going to be able to position them online and give them the functionality in terms of the website that they needed to sell their products, and what bells and whistles they didn’t need, and what they actually did need to make it work. It was very helpful for me to do product first, and then go into a service for product-based businesses, but even as a service business, I then started attracting other service businesses who needed me to build web presences for them as well, so it began to evolve.

I stopped working so much with product businesses and started working more with service-based businesses, so other coaches, yogis, and therapists, and those sorts of just … Actually, a whole lot of interior designers at one point. I was attracting a lot of those, so I started applying my services as well to service-based business. Again, really having this knowledge of what functionality a website needs for them to actually run their business online and what’s just extra fluff that’s going to be really overwhelming to them whenever they sign in to the backend of their website.

It gave me some skills to really determine both sides of the ecommerce coin, whether it’s service-based businesses or a product, and I did websites and some sense of coaching or guidance for these creatives who are trying to build online businesses for about six years. I did lots of projects. I went from being freelance and totally just working by myself to building a small little agency. I think at its height, we probably had 15 people working either as employees. Most of them were contract, but on numerous projects.

They’re all kinds of businesses. All of them were creatives though. Creatives are my people, for sure. Not only do I love working with them, but I am one of them, so I can speak their language. I can be talking about a website in terms that someone who has no idea about websites can totally understand, which really, again, put me in this really great place to service them in a way that a lot of people really couldn’t.

Brian Clark: Yeah, and amen to the, “You need your own platform.” You know I’m down with that.

Emily Thompson: Yes.

How Emily Leveraged Opportunities

Brian Clark: That’s amazing. You also mentioned positioning, and that’s something I’ve noticed about you in the sense that you emphasized that quite a bit both for yourself, and I think we just heard some examples of how. It almost sounds like … First of all, you’re positioned towards creative. That’s your foundational, “These are the people I talk to,” but it seems that throughout your career, you rolled with things a little bit, and in doing, it made adjustments along the way that allowed you to leverage the opportunities that were coming your way. Is that fair to say?

Emily Thompson: Absolutely. The entire process of everything in my life basically. I go out with this very like test and change mindset. Like a lot of us will make these goals and determine this path, and if we don’t reach those goals, then we’re a failure, and we don’t what we’re going to do with our life, but I’ve never really seen things that way. I like to play with what’s going to happen. Because I work that way, I attract people who work that way, and so positioning in that way I think is really important because it really gets you in with the people who’s going to get what you do.

I’ve worked with accountants. I’ve done websites for accountants, and lawyers, and those sorts of things. Though I can certainly give them the product, I don’t have as much fun with it. They’re not going to get my jokes for one. I have to position myself differently for things to come across in the same way to those sorts of people.

For me, rolling with the punches and just going at this whole journey in the way that I have has attracted me or has attracted to me the kinds of people who work the same way or at least who desire to work the same way, and that is creatives or people who desire creative careers for themselves.

For me, it’s just been identifying that, that quality in myself, and then speaking it in a way that other people can see it in themselves as well, and that allows me to at least hopefully share with people this idea that business or anything, any sort of venture that you want to go after doesn’t have to be this, “Make it work or let it die,” sort of mentality. It’s just enjoy the journey and have fun with it, and creatives are those people for me. Everyone has theirs. I learned early that creatives are mine.

Brian Clark: Yes, and it’s just so important. Pick your people, and stick with them. Who cares about what everyone else thinks?

Emily Thompson: Right?

Brian Clark: They’re going to ignore you, or they may not notice you at all, or they may hate you. The response is the same. Who cares? Okay?

Emily Thompson: Definitely.

Brian Clark: You talk to your people. They love you. You love them. Wonderful. Also, I like what you said. Inside our company, we say that we do what’s indicated as … we always have a general roadmap, but you have to pay attention to what’s happening out there in reality. It’s like surfing more than it’s like following a plan.

Emily Thompson: Definitely.

Brian Clark: That’s why we’ve never had a failure, but I think a different mindset says, “Well, you said you were going to do this, but you ended up doing this,” and I’m like, “Yeah, and it worked.”

Emily Thompson: Right?

Brian Clark: Other people are like, “Well, isn’t that a failure or a pivot?” I’m like, “I don’t care what you call it. It was the right move to make.” I’m afraid some people get locked in literally, lockstep according to what they wanted to do two years ago, not realizing that the world change and even you as a person change, right?

Emily Thompson: Yeah. Exactly. You change. I think it’s when we get into this mindset that we don’t change or we shouldn’t change that things start sucking basically because you do change. You have new experiences that adjust your mindset, and if you don’t recognize that, then you’re going to get stuck, and that’s not good for anybody.

How Emily and Kathleen’s Partnership Came About

Brian Clark: Okay, so let’s talk about a moment in your life. At some point, Kathleen entered your life. How did that happen, and how did you decide to start working together?

Emily Thompson: Sure. I don’t really remember exactly how it started happening or exactly when the point was that it happened, but we found each other online. I think I found her blog. She had fantastic hair, and I think I commented probably about her hair, and it ended up turning into like a blog commenting relationship. I’m sure some of us have probably experienced those, and it turned into emails, and then it turned into Skype sessions. We started skyping every month, and we were just talking about what was going on in our businesses.

I started my web design business probably about six months before she went freelance. She left her day job to go freelance doing brand work, and so we were talking about what it was like running around creative business and client stories, which we’ll often fill conversations like that. We started talking about families like growing our family, what it was like. For me, hustling as a mom, and for her, thinking about growing a family, and so it just was this very organic relationship that started very small and grew into monthly mastermind sessions with each other as to how we were growing our life and our business.

Then, I guess about three years into it, I just had this idea one day. I’ve since read Big Magic, and I totally recognize it as a Big Magic moment where I had this idea to start a podcast. I had never listened to a podcast other than Invisibilia, which I had loved, but I wasn’t … I didn’t even listen to Serial, like I’m not a podcast listener. I never really have been, but I had this idea that I needed to start a podcast, and it needed to be with Kathleen, and it was going to be for our joint dream customer, which is creative entrepreneurs.

We’ve been working together on some web design and branding projects together, so I knew what her work ethic was like. I knew that she’d get the job done if I were to ever partner with her on something, and we started it. We started a podcast. I sent her an email. As I do, very clear bullet points, these pros and cons, and what it would look like if we did it together. She wrote back and was like, “How can I say no to an email like this?” We got on Skype, and we talked about it. We talked through lots of things.

One of her things was, “I’ll do this, but I’m not going to touch anything that has to do with technology,” and I was like, “Deal because technology is totally my strength.” I was like, “I’ll figure that out. You do the branding because I don’t want to do the branding. I’ll take care of the website.” We just started like going through roles of how we are going to start this podcast and dreaming up the positioning for it and the kind of thing we were going to talk about, and we launched it a month later.

That was a little over two years ago. We’re over a hundred episodes into it now, and it’s been quite a journey. We went from just commenting buddies to business partners over the past five years, and it’s been a whole lot of fun.

Brian Clark: People ask me all the time because I’ve … Over the last decade or so, everything I’ve built has really been built by partnerships, and they always ask, “How do you evaluate a potential partner? It’s such a serious deal.” I think you just gave a pretty good brief summary of how you do that. First of all, yes, you like Kathleen. That helps, but it wasn’t the sole criteria, and sometimes I think it is with people. You’re like, “Can I depend on her? Does she have the skillset that compliments mine?”

Then, secondly, and this is important, you had a conversation where you clearly delineated what each person would do, but more importantly, what you would not do, and that’s very similar to how Tony Clark, my first partner and now COO, that’s exactly how we did it. We liked each other, but he could do a lot of things I couldn’t do, and I could do a lot of things he couldn’t do. We evaluated it, and we made clear where the line was, and it’s been a pretty harmonious partnership for … Gosh, how long has it been now? It’s been 10 years.

Emily Thompson: Yeah. That’s basically how it works. We have those conversations with people a lot too like, “How did you guys make this work, and how do you continue to make it work?” We did start it off with some little projects beforehand like, “Can we work together? How complimentary are our skillsets? How do we talk to each other in that sort of work environment?” because we’d had plenty of like friend conversations. Whenever you take it over to business, there is a shift, and there needs to be a shift, and can you both make that shift between a friend conversation and a business conversation and back again pretty fluidly?

We did. We started with working together, had that like initial conversation. We call these hard conversations because they are hard conversations, and a lot of people struggle with having them. Kathleen and I found out pretty early on that we’re both very capable of having them with each other in ways that are very productive. Whenever you can have hard conversations with people, I think you can start businesses with them.

If you can have these conversations and not get angry or bend out of shape, but really take them for what they are, and that’s figuring out what happens next, then partnerships work really well. Even as we do it, we still have hard conversations all the time where a new role will pop up. We need to figure out who’s going to take it, or a contract is received. We had to figure out if we like the terms, and what happens if we disagree, and where do we find that middle ground, so all kinds of things.

We’re continuously having those hard conversations. We’re continuously looking at our roles and finding out who’s going to do what best and who wants to hand whatever off to someone else, or that’s where building a team comes into place. Yeah. Can you work together? Can you have those conversations, and can you keep doing it?

Brian Clark: I like that, hard conversations, because I think too many people do anything at all cost to avoid having those, and that’s the problem because things happen.

Emily Thompson: Right.

Brian Clark: Water goes under the bridge. Next thing you know, you’ve got a pair of scissors in your neck. Maybe not that, but …

Emily Thompson: I just usually end them with a drink in my hand. We have them, and then we like …

Brian Clark: Probably healthier for your incarceration status.

Emily Thompson: For sure.

The Concept Behind the Being Boss Podcast

Brian Clark: Was the podcast right from the beginning called “Being Boss?”

Emily Thompson: From the beginning that everyone saw. Yes. There was a very short moment in the very beginning of planning like really just brainstorming that we almost called it “The Emily and Kathleen Show.”

Brian Clark: Oh, wow.

Emily Thompson: I’m very glad at this point that we didn’t do that because it’s grown so much beyond us. There was that moment where it was almost called “The Emily and Kathleen Show,” but we decided to take it a little more … not really professional, but a little more beyond us because we knew that the stories we would be telling would not just be our stories, and though we do have very healthy-sized egos … Actually, that’s probably why we decided not to do it as our egos are health at least most of the time, so we decided to go with Being Boss.

Brian Clark: Okay, so an act of positioning and as a statement of meaning that is like a movement, you treated it not like a podcast, but a movement, and that’s so smart obviously and probably a testament to why it’s caught on. What was your thinking there? What did Being Boss mean to you in the sense that it was the empowering concept that you wanted to share with others?

Emily Thompson: We didn’t even really see it as a movement in the beginning. For us, it was just an alternative name in terms of us really addressing the kinds of people we would be talking to, so not just talking to each other for our own sake, The Emily and Kathleen Show, but us talking to people who were creative entrepreneurs who wanted to make their side hustle their main gig, who wanted to be their own boss.

For us, it was just us positioning to the people that we wanted to talk to. It ended up becoming a movement. Of course, like Kathleen and I are very good at dreaming. We have very great skills of making big ass goals, and sometimes they’re ridiculous, and those are always my favorite ones. I’m pretty sure there was probably a conversation in the beginning. Actually, there was.

I actually think in that first email that I sent to Kathleen, I think the subject line of it was, “This is going to make us famous,” or, “Help us take over the world,” or something like that, so there were nuggets in there that definitely I think looked forward at what it could become, but for us, it was just positioning to the people we wanted to talk to. We wanted to help the people we were already helping by building brands and websites for that we wanted to help them be their own boss, so Being Boss became the title of it, and then it became a movement.

It took off really early. Kathleen and I had committed to doing at least 10 episodes with just the two of us, so not inviting on any guests. We wanted to create that foundation, find our own voices a bit before we had someone else on, and we’d also committed to doing 15 episodes before we decided to go after sponsors because sponsorship model is something we’re both interested in.

We had never really done a model like that for anything we had ever done before, so that was going to be a fun new thing for us to try out, but we had committed to doing 15 episodes before we did that. I think we had our first interview around episode 10 or so once we had done our first 10, but we were being sought out by sponsors before we got to our 15th episode mark. Pretty early on, we hit the ground running with it, and we put everything we had at that moment into it, and the payback was totally there, and it’s just grown and grown ever since.

Brian Clark: It’s such a common statement of, I guess, despair or what have you that people are like, “Well, it’s too late to start a blog, and it’s too late to start a podcast. It’s too late for this and that.” Yet, every single year, people do it and succeed.

Emily Thompson: Yeah.

What Led to the Growth of the Being Boss Podcast

Brian Clark: What do you think really, besides just the fact that it seemed to be a concept that hit … it just resonated with the people you’re trying to reach, what do you think were the key growth catalyst that you intentionally took to make the show grow?

Emily Thompson: That’s a good question. Intentionally, not very many things. I think for us, we accidentally tapped into a couple of things. One of those was that podcast even now is still such a new medium, and I think that … like we still describe it as like the Wild, Wild West. Like working with sponsors is very new for both like the podcasters and the sponsors. We’re still all trying to figure out the terms and what things look like. Our listeners are still just like diving in. A lot of people who come to us still to this day, this is the first podcast they’ve ever listened to. We’re still having to explain to people how to listen to podcasts.

For us, one of the ways that we unintentionally grew very quickly was choosing a medium that was new, and that was getting people away from their computer. Something that we’re finding more and more often, at least with the people that we talk to, is we’re done looking at a computer screen, so getting into a medium that allowed people to download it, and then go for a walk, or go grocery shopping, or wash the dishes while they’re still consuming our content has been a way that we absolutely see as catapulting us pretty quickly.

We’re not just there when people are checking their email or whatever. We’re there with people any time of day and night, which on one hand is really creepy, but on the other hand, it’s really awesome and has been really advantageous for our growth. I think too that that initial thing for us where we were going to do 10 episodes before we had on any interviews I think was really important for us. I feel like a lot of people dive right into doing interviews, and those first ones can be so weak. Sometimes, people will get really big people in or try to for those first couple of episodes before you really know how you’re going to like asking questions or how it is that you like to format your show.

Going in with this, again, just testing change mindset of, “Let’s do 10 episodes, just the two of us. See how it goes before we invite anyone else into our space to see how we can curate this space,” I think was a really important step for us to take. We totally believe in some minimal viable product. We did not launch our podcast with all the things. We did a podcast. We did show notes on a very simple website, and that is it.

We made some social media graphics that we would push out on our own Instagram accounts, but other than that, we weren’t doing blog posts, and we weren’t doing webinars and all the things. We just did the thing, and we would focus on doing that one thing really, really well until it was time for us to add to that one thing. I think that was maybe the most intentional thing that really helped us focus in on gaining some of that initial growth was we just did the one thing as well as we possibly could.

Brian Clark: That’s an excellent point because a lot of people think it’s more about the marketing than the content, but really good content tends to spread as a function of marketing where you feel like it’s just happening, but of course, you … I did the same thing for the first 17 months of Copyblogger before we had a product or anything. To some people, I think they just look at that, and they’re like, “Oh, I’m not going to do that much work until I get the reward,” but the reward doesn’t come if you don’t do the work.

Another thing I thought was interesting is, as you mentioned earlier, a lot of us aren’t podcast listeners. We’re not audio people, but that’s not the criteria for starting a podcast. You have to have something to say and be enjoyable to listen to saying it, and you and Kathleen are clearly that.

Emily Thompson: Absolutely.

Brian Clark: Again, I had so much fun. I don’t know what number guest I was, but I thought it was early.

Emily Thompson: I think it was. I’ll have to look that up, and I love something you just said about like about the reward like you feel like you need to have the reward in order for you to keep doing it, and Kathleen and I went into this as doing it was the reward. We still say to this day, and I wonder if it’s actually true, but we would still be doing this if no one was listening because Kathleen and I have a blast doing it. If there were five people listening, and two of those are our husbands, and the other two was our moms, and then this weird fifth person, we would still be here podcasting because it’s been so much fun.

I think that is probably another intentional thing that we went at with this was we’re going to do it. We’re going to release this to our newsletter list because we each had been building lists, and they weren’t huge by any means, and we’re just going to see what happens, and we’re going to just keep seeing what happens. We didn’t sell anything for months. We didn’t launch like our signature offering or whatever for a year and a half. We didn’t go into it expecting to do any of those things.

Really, we just want to create a podcast. We wanted to make something that’s something that … It was part of that first conversation was that we’ve been working together creating these things for our clients, but we were both itching for a passion project that fulfilled a need for us to create something for ourselves, and so for us, the podcast was something we wanted to make. We just wanted to make something new that neither of us had done before, that wasn’t for anyone else really, but ourselves, and so for us, doing the thing was the reward, and it continues to be.

My favorite thing that I do every week is getting on Skype with Kathleen on Wednesdays and just talking about whatever it is that’s on our mind, that’s on the mind of our community, and cracking jokes, and being dumb, and getting our sound engineer to cut out the stupid things that we say that should not be listened to by anyone else. That’s a whole lot of fun to me, so for us, doing the thing is the reward. All the money that we get from it, and the community engagement, and the places we get to travel to, those are just many cherries on top of the great joy that comes from making the thing.

Brian Clark: Yeah. it’s the intersection of doing the thing and serving an audience that makes it all come together, but I think where we started with this is the attitude is, “This is for me to make money, and if it’s not doing that soon enough, then I’ve got to go do something else.” You’re not going to make it.

Emily Thompson: Right. No. Not very far at least. Even if you do make it, you’re not going to love it. In which case, what’s the point?

Brian Clark: Absolutely. Can you share a little bit of audience size and reach if that’s something I can ask?

Emily Thompson: Sure, I think so. I guess so. Right now, our download numbers are about … I guess they’re at about 40,000 a week if I’m not mistaken, and it fluctuates.

Brian Clark: How many episodes do you do?

Emily Thompson: I know we have over … We have about 110 …

Brian Clark: No. I mean, per week. I’m sorry.

Emily Thompson: Oh, per week. Good. I was going to say whoa. We do two episodes a week. We do a full episode on Tuesday, and then we do a minisode, which is usually between five and 15 minutes on Fridays.

Brian Clark: Excellent. That is so great. You’ve got sponsorships obviously.

Emily Thompson: Mm-hmm (affirmative).

The Fruits of the Being Boss Movement

Brian Clark: You hinted that you do have a flagship offering that you waited a while to put out there. Tell us a little bit about that, but also, I know you’re going to new and even bigger things with the whole Being Boss concept. I want to hear about that because I think that gets people excited. If they can accept that you’ve got to love the work, and you got to stick with it, and serve the audience, great. Okay, but I still think people get just a little jazzed up to hear stories like yours where they go, “And now, they own Bolivia.” Whatever the case may be, but no.

Emily Thompson: That’s the goal. That’s the goal.

Brian Clark: Tell us a little bit about what has been the fruits of the Being Boss movement now that it is such and where you’re going with it.

Emily Thompson: Sure. The sponsorships did come first. We had our first sponsor approach us just a couple weeks into the podcast, and that was Freshbooks Cloud Accounting. One of the people in their office actually started listening to our podcast.

Brian Clark: Also the sponsor of this very episode.

Emily Thompson: Oh, there we go. Plug ad here.

Brian Clark: I guess that’s my cue to talk about our sponsor Freshbooks, a great solution and a great company, but I think most importantly, a true friend of the independent business community. If you’ve been listening to Unemployable for a while, you hear all these stories about how people built businesses, and leveraged audience and virtual teams, and were just different. The problem is that in our operations day to day, we’d rely so much on software, and so little of it is actually designed with the way we operate in mind.

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Emily Thompson: Yeah. Our first sponsor was Freshbooks and again Wild, Wild West like they had started sponsoring some podcasts by that point, but like they were still very open to the conversation. At least they had like a good place to begin with us because we had no idea. We had no idea what to ask for. We actually went into the first meeting with some ridiculous asks, and they were like, “Uh, let’s just start small and see how it goes from there,” and we did. I can’t remember where we started out with them, but we continued to grow.

As our podcast grew, every quarter, we would have a meeting with them and say what our numbers like because that’s another thing that Kathleen and I concern ourselves with and me especially. I’m the metrics girl where I want to know what the download numbers are, and I’m the one who’s always asking number questions.

We’d get into these meetings with Freshbooks, and I’d want to make sure obviously that our relationship was good on both sides. We would talk about numbers, and then we would make adjustments, and things just continued to grow for us. We ended up getting our second sponsor I think maybe six months after that, and we’ve recently picked up another sponsor for our minisodes.

Freshbooks has stayed with us all the while. We’ve had some sponsors come and go like as their high and low seasons come and go, but it’s been some really fun relationships. I think that’s the thing that really helps us and really makes us feel good about sponsorship relationships because sponsorships can be … there could be gray areas where someone just gives you money, and you put their logo on something. You call it a day.

Kathleen and I never really felt super comfortable with that relationship and on those terms, but we’ve really grown to love our Freshbooks contacts. They’re friends of ours, and we chat with them via email often. We usually know when they’re on vacation or where they’re going, what they’ve been doing, and they invited us up to Toronto a couple of months ago to do an event at Freshbooks Headquarters because we just all wanted to hang out together and see what it would look like for us to do an event together.

Sponsorship relationships for us were more about just selling ad space and more about creating these really mutually beneficial relationships with companies, so that they could get their awesome products in front of our people, and our people could get access to things that would help them be more boss, which is one of those underlying rules as to whether or not we’re going to take a sponsorship.

These really were relationships that remain really important to Kathleen and I, and we cultivate those relationships, and they’ve been very beneficial for all parties involved, which I think is … It makes me feel better about going after a sponsorship model.

Plans for the Future

Brian Clark: Isn’t there, I think, a book in the works and all sorts of other neat stuff?

Emily Thompson: Yes.

Brian Clark: I had this conversation with Jon Nastor at the beginning of the year about his podcast, Hack the Entrepreneur. It was the same thing with him. He’s like, “My sponsorships basically take care of us,” and yet, that’s really just the tip of the iceberg.

Emily Thompson:Yeah. Basically, it is just the tip of the iceberg. We did start bringing in our team. In the beginning of the podcast, Kathleen and I did everything ourselves. I edited the podcast. She did the show notes. I did the website. She did the newsletters. Like we did everything between the two of us, and then as we got a sponsorship, we brought on our sound engineer. We got someone in to do some social media marketing, and it began to run the ship for us.

During that time too, Kathleen and I were still working in our individual businesses. She was still doing branding. I was still doing websites, and we found ourselves pretty overwhelmed and not really loving the client work anymore because we wanted to be hanging out with each other, and creating this podcast, and engaging with our community, which is so thriving, so we decided to launch a product.

For us, that’s the Being Boss Clubhouse, which is more of a mastermind community offering. Very unlike anything, which is our ammo is that we are going to make something unlike anything anyone has ever made before. That for us is the Being Boss Clubhouse, and that allowed both of us to step away from one-on-one work so that we could focus solely on the Being Boss brand.

I’ve also created some other digital products for Indie Shopography, my business, for fun. Just things that I’ve been wanting to get out of me anyway, but then there was the book. Kathleen and I very early on, it’s part of that like big dreaming and scheming time in the beginning, realized that it would be easy for us to create a book with Being Boss. Based on the content that we were crafting and sharing, we could already see this becoming a book, and a book is something that’s always been on mine and Kathleen’s list individually. It’s something we’ve talked about for years like, “At what point are we going to have what we need to make a book?” and it just so happened that it happened with us together.

We had a couple of book agents who reached out to us. No one really jived with us in a way that we need them to until they did, and so our book agent that we ended up working with reached out to us the end of last summer and was like, “I’m a huge fan of your work. You guys helped me leave my publishing job. I want to help you guys get a book deal,” and we were like, “Game.”

We talked to her. She was totally our people. She helped us get a book proposal together, helped us curate what the content would look like, send it off to publishers. At the end of last year, we got a book deal. This year, Kathleen and I have been taking the content that is being boss. It’s the things we’ve learned from interviewing all of the people that we’ve interviewed, including you, and from the conversations that we’ve had with each other and with our community, and we’re turning it into Being Boss the book.

Brian Clark: Sponsorships, membership site, digital products, book. You’re off to a good start.

Emily Thompson: I don’t hate it.

Brian Clark: Don’t try to get into software or web hosting, okay? I’m watching you.

Emily Thompson: Oh.

Brian Clark: I might sponsor your show. Come on. We’ll do it that way.

Emily Thompson: Right? If you’ll help us be more boss. No, I think … this is my favorite thing about being a creative, and being a maker of things, and having the brain of an entrepreneur is I can do whatever the hell I want, and I find so much freedom and happiness in that. It makes me look back to that college degree where I was going to be digitizing maps in a cubicle for five years. It makes me so happy that I chose this path instead of the other one.

Brian Clark: Absolutely, and that’s a great point to close on. Thank you so much for your time, Emily. I’ve enjoyed this conversation just as much as our last one, so hopefully, we can do more of this stuff.

Emily Thompson: I agree. This is a pleasure. Thank you so much for having me.

Brian Clark: All right, everyone. Some good solid information in there. It compliments a lot of what we’ve heard from earlier interviews this year with Jon Nastor, with Andrew Warner. If you’re thinking podcast, again, you got to think in terms of the gap in the market. What inspires people? What do they need to hear, and why do you need to be a particular leader of that thing? Then, all the good stuff happens, but don’t put the cart before the horse. Thanks for listening and keep going.