#3 Jesse Brown: Growing Canadaland Through a Deal with the Audience

In this episode, we have an amazing conversation with Jesse Brown, Publisher and host of Canadaland, an independent news site and podcast network supported mainly by its audience. Focusing on Canadian media, news, current affairs and politics, Canadaland and its six shows get over a hundred thousand downloads every week.

Show Notes

It's hard to ask for money from listeners.

Jesse Brown of Canadaland didn’t just get a few bucks, he’s built an entire podcast network that now spans 9 shows, attracts 100k+ downloads per week and attracts over $30,000/mth in member support.

From an itch that needed to be scratched and a desire to have conversations about the state of media, Jesse now leads an independent, people-powered media company at the forefront of Canadian media, news, current affairs and politics.

How did he achieve all that?

He started by asking...

Key Takeaways

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Podcast Transcript

Quick Navigation

  1. What is Canadaland?
  2. How did Canadaland get its initial guests?
  3. How did Canadaland grow?
  4. How does Canadaland maintain its relationship with its listeners?
  5. How does Canadaland's financial model determine the content it produces?
  6. Why do Canadaland supporters drift in and out of support?
  7. How does Canadaland keep in dialogue with its audience?
  8. How does Canadaland fund its investigative pieces?
  9. How does Canadaland monetize its one-off projects?
  10. How did Jesse Brown separate himself from Canadaland?
  11. Why did Canadaland accept $1M in funding from Tiny?

Jason Sew Hoy: Hey, everyone. Welcome to Supercasters. I'm Jason Sew Hoy, Co-Founder and CEO of Supercast. And on this show, we interview world-class podcasters, deconstruct their growth strategies and find out how they build sustainable independent businesses that thrive on a strong relationship with their listeners.

[00:00:44] Today, I'm super excited to be talking to someone who really epitomizes all of the things I just described. Jesse Brown is the publisher and host of Canadaland, an independent news site and podcast network funded primarily by its audience. Canadaland's primary focus is on Canadian media, news, current affairs and politics and their podcasts of which there are currently six, get over a hundred thousand downloads per week. If you want to connect with Jesse, you can find them on Twitter @JesseBrown. Hey Jesse welcome to the show.

[00:01:18] Jesse Brown: Hey, Jason. Good to be here.

[00:01:20] Jason Sew Hoy: So first of all, could you maybe kick us off by telling us a bit more about Canadaland for those that haven't heard of it?

What is Canadaland?

[00:01:27] Jesse Brown: Sure. Um, it started, I guess, uh, seven years ago or a little bit more than that when I wanted to do some kind of version of media criticism in Canada. I was inspired by everything from the Daily Show to On the Media, the NPR show, which is about the media to the late great David Carr was a media columnist in the New York Times who I admired very much. There was just like a ton of different stuff where Americans could have a conversation about their news media. And there was nothing like that in Canada. And, um, I had been a working journalist for about 15 years at that point, writing about technology all sorts of different things for, you know, I was a CBC radio host, magazine writer, just all kinds of different work, but I couldn't sell media criticism to any of my producers or editors. There was the sense that Canadians don't care.

[00:02:20] And it was one of those ideas that you get rejected and you get rejected and it just doesn't leave your head. And eventually my wife said like, you either have to just do this or shut up. Um, because you've been bothering me about this for months and, you know, it's obviously something you really want to do.

[00:02:34] And, you know, considering myself like, Oh, I'm a professional, I've done national radio shows. Like, am I really gonna launch a podcast for free? That was the biggest, I think, block for, for many months, the idea that, I would be downgrading myself to some sort of amateur level. Um, and I regret that, that held me back as long as it did.

[00:02:54] Um, Yeah. Ultimately, I took my wife's advice and I just started podcasting. And the idea of the show was really, the initial idea was really just for me to have candid conversations, the kind of conversations that journalists have with each other over drinks, after work about the story that didn't make it into the paper today or onto the broadcast today.

[00:03:13] Um, share some drinks and just sort of talk the way that, you know, the way that Mark Marron talks to comedians. I wanted to talk to journalists, but it very quickly became something more than that. Yeah, I completely underestimated, uh, how much Canadians wanted to hear about this stuff. And not only that people, started bringing me stories.

[00:03:33] There was nowhere to bring media stories and it turned out that there was a lot that was wrong with the Canadian media, everything from our biggest news anchors doing paid speaking gigs for the oil industry, and then going to work and reporting on the oil industry, to what became our biggest story, which was, the fact that John Ghomeshi, one of the star broadcasters of the CBC, the Canadian Broadcasting Corporation. I learned through a series of women who came to me to be my source that they had experienced, really serious,  violent assaults in the course of relationships with them. And so I ended up reporting that with the Toronto star, but also Canadaland and then Canadaland became a news organization, a podcast network. It's just grown and grown since then.

[00:04:24] Jason Sew Hoy: Yeah, amazing. And, you know, going back to the early days, given its stance and, and, the default position, I guess of offering critique or criticism or to call a chat around, you know, what's going on in the scene, was it, difficult to get initial guests, initial listeners?

[00:04:45] Like how did you kind of seed that whole thing going?

How did Canadaland get its initial guests?

[00:04:50] Jesse Brown: It was tremendously difficult to get people to come on the show. I had some help and I had some breaks, you know I had maintained a mailing list from people who liked my previous tech journalism. I had about a thousand names and I told them like, look when I ended my last you know, regular gig as a tech journalist, I said, look, I don't know what I'm going to do next, but if you want to know, give me your email address, I'll only use it once.

[00:05:16] One day, I'll send you an email to tell you what my next project is. That was an idea that, my friend Cory Doctorow gave me. So I had about a thousand names. I'm like maybe, maybe half of them will listen, podcasts, maybe a quarter of them. I don't know. And then for the first episode of Canadaland, I called in a favor and there's a, sort of a legendary broadcaster here in Canada named Michael Enright who used to be my boss.

[00:05:35] And he, I think at some personal risk, agreed to come and drink bourbon with me and talk shit about the Canadian media and really speak very openly and candidly. So for the first episode, it's like we realized the vision of the show right away. And then there was like a year where I almost didn't do it again.

[00:05:55] Like getting somebody to come like Canada is so small and the media is even smaller. And the idea that you would say something critical about a company. There's not that many companies. So if you say something critical and you're a journalist, or you're trying to get a TV show made, whatever you do, you're, you know, the, the thought was that you would be blacklisted. And so, you know, if you listen to the early episodes every now and then we did something good, I'm not going to put down any of my guests because everyone was very kind to come on the show at all. But a lot of them had nothing to do with the original, like I had an ex girlfriend come on and just chat with me.

[00:06:25] Like I was just like, you know, the one thing I was, I was very dedicated about was my training. As a public broadcaster was you put the show out no matter what, you know, if you say it comes out every Monday morning, it's out every Monday morning, you do your best. And maybe you're going to fall short, but like, you just need to build up that it took off, you know, it wasn't long before we were up to like five, six, seven, 10,000 listeners.

[00:06:48] And before I had any kind of financial model for it, I had a robust audience that was really engaged.

[00:06:55] Jason Sew Hoy: Right. Interesting. So, sorry, you said you did your first episode and then you didn't touch it again for a year?

[00:07:01] Jesse Brown: No, I did my first episode as what I dreamed of the show to be like my first episode was that kind of candid after work conversation. And then I did it every week. For a year, never really coming up to that vibe of the first episode. I don't want, I have to go through the archives to make sure that's totally true. There were some little breakthroughs here and there, but it was definitely, you know, establishing to this community of people in media, in Canada, that you could go on.

[00:07:30] This podcast, podcasts were pretty new in 2013. You know, like that you could do this thing and you could speak candidly and was something that took some doing, you know, like now, you know, everybody just does podcasts all the time. I think that probably when someone like Mark Marron first was asking a comedian to come onto his show.

[00:07:52] And like, I want you to talk with me about the guy who had booked at the comedy club and who was your friend and who you didn't like, you know, people probably like, why would I do that? You know, what's the point of that? Um, so, you know, in Canada, we, we tend to lag behind American trends a few years. So it certainly was an uphill battle, getting people to agree to come onto the show for those interviews. But we got there.

[00:08:13] Jason Sew Hoy: Interesting. And given, you know, there were so many new things, new format, a new audience, controversial topics. What were the things that I guess you experimented with? Is there anything about, I guess those, early days that you gravitated towards or latched onto as, yeah, this is going to help me grow my show?

How did Canadaland grow?

[00:08:38] Jesse Brown: I mean, I, you know, experiment is the right word. Um, you know, there were a series of YouTube videos that I did right off the bat. Didn't continue with that. Like, you know, a lot of people like see video, like what you graduate to from audio. But I was like, look, you know, for the same number of views as I would get listens, the amount of work to make a three minute piece of content versus like a 30 minute piece of content.

[00:09:03] Like it's incredibly time consuming to make decent video. I'm just a radio person, you know? So that was like an experiment. I definitely experimented with format in that first year. I did some short, little quick and dirty documentaries. I did a quick documentary on the early years of vice magazine.

[00:09:21] So it wasn't just interviews. There was like already kind of aspirations to doing some original reporting and some longer storytelling. Um, like I said, I played around with like, well, what if I expand it from just media people that talk to, you know, different kinds of people and. You know, trial and error just found out what made sense and what felt like a Canadaland episode and what didn't.

[00:09:41] And, you know, one thing, like this was something that was built absolutely in collaboration with its audience, because the back and forth about like, you just know immediately, if what you did, you know, you can see it in the episodes performance, you can see it in the social media commentary. You can see it in the emails that come in. You can see it if people want to come on the show. Um, so you really do know if, if people are responding to, to your work.

[00:10:05] Jason Sew Hoy: Right. Yeah. And that's something that I wanted to dig into a bit further, you know, one of the strengths of Canadaland, you know, very much is the relationship with your audience. I wanted to get your take on why that is. More specifically, what's different about your approach to cultivating that, in comparison with other media companies?

How does Canadaland maintain its relationship with its listeners?

[00:10:32] Jesse Brown: This is a really important thing for me. Yeah. It's something that I think about a lot and I know we're going to talk about the financial model and the listener support that we get. In 15 years of writing magazine articles or hosting shows on the radio, the audience was so distant and sometimes it was represented by the most extreme people in the audience, you know, who calls in to the voicemail of a CBC radio show is the person who's furiously angry. And sometimes those people weren't well. People who kinda like what you're doing, I've never written an email cause I kinda liked the radio show. I just kinda like it, you know? And then I listened to it again, you kind of like, you know, you get that, this weird warped idea in your mind that your audience is just, um, these really extreme people who either, you know, most of the time it was negative or, or in magazines, you know, you would file something.

[00:11:25] And then like two or three months later, we got published and like maybe two or three months after that, there'd be a letter in the next issue about your piece. If you were lucky, you know, really your relationship was with your commissioning editor. It was with your producer. That's the person who you had to please was whatever person in the media organization hired you and was going either hire you again or not.

[00:11:46] It's just so completely different. Um, the way that we work, the only reason I'm allowed to do this as my job is that one day after podcasting for a year and giving it away for free, I said to my audience, I love doing this. And it seems like a lot of you enjoy listening to it, but I can't do this for free, you know, I'm, I'm putting more and more resources into this.

[00:12:09] I'm actually reporting stories now. Um, and it's taking, like, I don't want to do my other freelance work and I've sort of stopped doing it, but I've got a mortgage and I had small kids at the time or one, I guess, at the, uh, no, I had, no, I had both my kids at the time. So yeah. I basically just made this appeal saying like, let's work something out.

[00:12:27] Like let's cut a deal. Like, and if I was terrified that it would be one of those crowdfunding campaigns where like, you know, you ask for a thousand bucks and you get 12 and, you know, it's that person's uncle who did it, you know, and it's very embarrassing to fail. And I was really afraid of that failure.

[00:12:41] But within hours I had my first goal of crowdfunding. So to this day, I just know that like the audience is what saved me. The audience is why this exists. Um, Other things come, you know, advertising investment, all sorts of different things can push and pull. We have staff now, and everyone says the same thing who comes to work here.

[00:13:04] They're, they've never felt more connected to the audience that they serve than, you know, in their other work, in the media than they do at Canadaland. And it's a unique thing and I feel passionate about it and I feel like there's a specific, you know, as you know, Jason, like we're just experiencing this some wider crisis in news where, where the news media is just like really collapsing and no one knows what model will save it.

[00:13:29] And I feel like there's this special thing that we've stumbled into here where when your audience pays you for news, you are aligned. The goals are aligned. We don't pay people for exclusive access to news. You know, we have a little bit of bonus content, but people told me I'm paying you, not just for podcasts that I enjoy.

[00:13:52] Or for information for me to have that other people can't, it's just the opposite. I'm paying you to break stories that then the whole country will be talking about. And if you ever put your news content behind a paywall, I'm not supporting you anymore. So, you know, I have this, like, we are in partnership with our audience in a way that I think transforms the practice of journalism itself.

[00:14:15] Jason Sew Hoy: Yeah, I love that. That's, that's a great phrase. You're in partnership with your audience and I love to explore the bit where you said everyone in your team just says that they're never felt more connected to the audience and what is going to serve them best.

[00:14:37] And the alignment of incentives. How do you think that changes the way you think about content and you know, what you do choose to cover and what you don't choose to cover and the direction that you take in your shows?

How does Canadaland's financial model determine the content it produces?

[00:14:50] Jesse Brown: My perspective on it is that it is almost completely a positive factor. I don't know that that's true everywhere. I think that, you know, it's been, it's been positive to me. Oh, You know, are you just, pandering to the political sensibilities of your audience? And, uh, I think that's a legitimate question to ask of any, like subscription-based journalism.

[00:15:14] The thing about Canadaland is that like, though I think people consider us left leaning in perspectives. We're not politically partisan for any party or ideology, we're not, we've never really backed a political candidate and our paying subscriber base. I couldn't pander to them if I wanted to.

[00:15:37] Cause I don't actually know what they think. You know, like there is no clear consensus that, you know, like right now, we're involved in a story that is, the biggest political story in Canada. And it's, it's a very negative story for Justin Trudeau. It's hilarious for me to go on Twitter and read that Canadaland is a right wing rag.

[00:15:56] That's trying to take down Justin Trudeau because most days of the last seven years. The detractors say you guys are a left wing communist. I can really honestly tell you that, like, I don't really censor myself. In order to, I can't remember ever censoring our content or feeling like, I think this is true, but our audience won't like it.

[00:16:22] There are ways in which the audience response does affect what we publish for sure. But I think they're kind of good. Um, you know, there are, there are times when we second guess ourselves about like, Is this just the kind of thing that we're interested in or is this like legitimately something the public's gonna be passionate about as well?

[00:16:42] Um, are we just sort of staring at our belly buttons too much about this one topic? Cause it's kind of a nerdy insider Canadian media sphere thing and there are bigger things to get into. Um, and then just issues of accuracy. 

[00:16:54] Like there's nobody in our paying audience...I'll put it this way that I hear the phrase: I don't like Jesse Brown or I don't agree with Jesse Brown, but I support CANADALAND anyhow, on an almost daily basis. So the deal we have is not that my job is to represent someone's ideology or to represent their political agenda. And every now and then somebody will cancel their support. Cause they don't like that.

[00:17:21] We criticized a politician a certain way or something like that. And I feel the same way. I think like, look, I'm sorry to lose you, but if your support was contingent on us not being critical to your favorite politician, you weren't supporting the project that we are trying to get people to support.

[00:17:37] You know, you had some weird idea, but what we are, and maybe it's better than this relationship and now.

[00:17:43] Jason Sew Hoy: Right. Yeah. I do think it's interesting. It just in looking back through some tweets that people have put out there, you know, declaring their support for Canadaland. Um, I noticed a few of them. Actually tell that story about how they floated out of support, you know, for, for various reasons. But you know, now that they've come back and I imagine you probably see that time and time again, that, you know, people even, you know, with their own personal support, you know, just float in and out of being a Canadaland supporter.

Why do Canadaland supporters drift in and out of support?

[00:18:11] Jesse Brown: Yeah. It's a really weird relationship that I think not just like podcasters or, or Canadaland, but just journalists have, like, our job is to tell the public the truth about things that are important.

[00:18:21] And the truth is not always something you want to hear. And so sometimes we'll tell the truth, but something that people have absolutely dying to have exposed, or to learn the truth about. And then they'll pledge their undying love for us. I became a supporter today. You're doing God's work. God bless you. And then the next day we are in their eyes putting too much attention on the wrong issue. We're making a, you know, a mountain out of a mole Hill or being unfair to somebody and they dump us. Yeah. And then sometimes they come back after that. Yeah. You know? And so there's almost like an educational process that occurs where it's just like, um, and we can be wrong too.

[00:18:57] Like, I'm not saying like, Oh, we are this plain dealer who offends everybody. Like sometimes, we can look back at our, there's different kinds of being wrong. There's factual inaccuracy, which we absolutely correct every time, time. And then there's some areas where you think like, well, our editorial focus was a little bit off on that. And the audience lets you know too.

[00:19:14] Cause sometimes you know, you'll go, you know, and get passionate about something and you'll see your, your supporter base dwindling. Though there's never been a real big boycotter exodus, even when things like, you know, Twitter's not reality and sometimes I'll be getting dragged on Twitter with hundreds of people agreeing that we've done something terrible.

[00:19:31] And then I check our crowdfunding and we're down like six people, you know? So it's like, that's interesting, but you know, I'm not going to say that I don't look at those numbers. But I don't look at them just to say, oh, we better change our message. Cause we're losing supporters. Maybe I would, if we had hundreds of people leave, but it's never happened instead I say, wow, like, um, I'm happy or I'm willing to lose supporters who are angry with us.

[00:19:57] If it's for the right reason, is this the right reason? Is everybody who's angry with us wrong? Cause sometimes they're not. Sometimes they have a reason to be wrong, angry, angry with us and we're wrong in some way. There's, there's just this like real time thermometer we have, like, we're just, we're just like, Always in dialogue with our audience, um, our paying audience and then the wider audience.

[00:20:21] And then the audience beyond that, that doesn't actually listen to our podcasts, but could get angry about something that we reveal or tweet, and we're always balancing those things and it's a very different kind of practice of journalism than I've experienced at other and other newsrooms.

[00:20:36] Jason Sew Hoy: So you mentioned Twitter a couple of times now, obviously that's a key way that you engage and just keep a temperature check on your audience. Are there other ways that, you know, you're able to keep a dialogue with them?

How does Canadaland keep in dialogue with its audience?

[00:20:51] Jesse Brown: Yeah. Right from the start I make my email address available at the end of each show. I encourage people to email me. For the first few years, I said, email me. I respond to everything that you send that became impossible at a certain point. So I said, email me, I read everything, you send, that I can do.

[00:21:06] I read everything that comes in. Sometimes I respond. Email is definitely that, you know, and then there's, you know, I dunno my, like, it's just a, it'd be good to actually see, you know, my DMs are open, so people are, you know, we still get Manila envelopes, um, dropped off at our physical office with documents that people want us to report, you know, so there's, you know, everything from our Facebook page.

[00:21:30] So keeping track of all of the different, you know, input points, we very explicitly didn't leave a comment section on our website. Like we figure, like if people want to comment, they'll find a way to comment, you know? And that was a good decision. Cause like, even without that, we still have too many.

[00:21:45] Um, but yeah, I'm constantly just cycling through them. Like I want to know what people think.

[00:21:50] Jason Sew Hoy: Yeah, that's great. Just circling back to the, the content I'm curious because Canadaland, you know, obviously has, you know, stories that break from time to time. The traditional kind of news cycle type stuff. And then, um, you also have the, the bigger pieces, you know, the, the call mules, the Thunderbay, uh, types of projects, which are a lot more involved, um, and, and are released as mini-series.

[00:22:18] Um, so I'm keen to understand how you, at a high level plan for what turns into something that's much bigger, you know? And, and how you think about funding, those types of things, you know, versus doing the day to day stuff.

How does Canadaland fund its investigative pieces?

[00:22:39] Jesse Brown: Yeah. So, you know, with podcasting, we keep a watch on the trends and we're also just podcast fans. So of course, when Serial changed everything and we saw this huge influx of new listeners who are interested in beginning, middle and end standalone series, you know, mostly true crime, but not necessarily, we really started to think about, could we make a show like that?

[00:23:05] And some of us have a background in documentary audio and I've done documentaries. It's sort of my favorite thing to do. And so we were kind of like, you know, playing with the idea that maybe we could do that too. And then, then Ryan McMahon, who one of our hosts of our show Commons who's an indigenous storyteller, comedian, I think journalists, I think, he might not be a quick to throw that around, but I consider him one. Anyhow, he brought our attention to a series of really alarming stories that have Thunder Bay, Ontario, which is the hate crime capital of Canada. It's the homicide capital of Canada. And it's a place where there's a lot of anti indigenous racism.

[00:23:43] I started working with him on, on this, but what we, what we eventually did was we have an annual crowdfunding campaign. And that's also a way that we check in with our audience and not just to say, Hey, you know, at the beginning it was, we don't want to bug you every week. So we're going to just have one month, like as if, you know, PBS or NPR would have their like pledge drive, same concept.

[00:24:03] We spend a month where we just explicitly. Ask you to support us and hit that really hard. And, um, you know, we, we will not just say, Hey, give us money. But like, here's what we'll do if you give us money. So we'll have different projects that we want people to fund. And so we had Thunder Bay. We kind of pitched, it's almost like a pitch, you know, when you're trying to get like a movie green lit or something, but it wasn't, it's just to the world, just to our listeners and to possibles of supporters.

[00:24:30] So this is what we have in mind. We described the project as best we could and said, you know, if you give us enough money, we'll go make it. And we got that money. And so we made it. Um, and it was, you know, I think it's the best thing we've done. Um, and it, and it completely brought our content to new audiences is just to, you know, it'll hit 2 million downloads this year.

[00:24:53] It brought us a huge American audience. We've never seen before. It's currently being developed for television, both as a documentary series and as a fiction series, it was just like, it's an important story. And I think we told it well, and the world really, really responded. However, I vastly under budgeted it.

[00:25:09] I never made a show like that before. And so though we got the budget that I asked for it wasn't enough money and we went into the red and maybe if the TV show actually gets made, we'll will finally cut a profit off of it. But yeah. Really changed in, in future years. Um, you know, when we set our goals, I try to set them more realistically and didn't always reach the goal.

[00:25:31] You know, for example, we wanted to make a sequel to Thunder Bay. I mean,Tthunder Bay has a huge committed audience and a lot of them give us money to get to the sequel, but not enough because I actually priced it properly. Um, and what we realized through that was that crowdfunding is powerful. It's the backbone of our business.

[00:25:49] It's really effective at funding day-to-day journalism. And that, in that same way that I'm describing, like every day we do our jobs everyday supporters come and go and, you know, but to say to people, give us money today and in eight months. We'll have this six episode series for you and actually asking for the right amount of money, at least in our experience in Canada, which is, you know, a market that's, you know, a 10th the size of America in terms of possible listenership, it doesn'twork.

[00:26:17] So the way that we are going about our mini series we've since done another one called cool mules. We did not crowdfund for colonials. We just funded it out of our general coffers. We really want to make more shows like this. And so we, we are fortunate enough that we got an investment, this year and a good portion of that investment is going to be, is getting purposed towards building a department here that is just going to be making those standalone series.

[00:26:50] And it's another experiment from us because, you know, we'll make some series, we'll pour our hearts into them. We'll tell stories that we think people should hear. And we hope that we have gotten better at selling ads and at, maybe this TV stuff will work out cause cool. Mules has also been optioned for television and we will, you know, see if making these standalone shows can be a profitable enterprise, as well as a journalistically and creatively rewarding one.

[00:27:15] Um, you know, and if so, we'll keep doing it.

[00:27:19] Jason Sew Hoy: Interesting. So, and when it comes to the financial part of that, you know, these, um, these one-offs and, making that commercially rewarding. How are you thinking about that?

How does Canadaland monetize its one-off projects?

[00:27:33] Jesse Brown: Um, I'm hoping to, you know what, when we got that big American audience for thunder Bay, we didn't make a cent off them. We didn't, we don't really have the capabilities. We have a wonderful in house sales salesperson who, um, has wonderful relationships with Canadian brands.

[00:27:47] Uh, we don't really know how to sell ads in America. We have a partner. Shipped with Midroll and they love our content. We're going to hope that we do better with our next project selling inventory to American ads through Midroll. We also are hopeful  that with Supercast, what we saw with cool mules, and this was also an experiment we had just started using super cast on our main show.

[00:28:16] And then we launched cool mules and I thought, you know what? Like. Let's try to use Supercast on this show in a way that I've seen other like, you know, Stitcher does stuff like this, where it's like, okay, this show is free. If you wait a week, you're going to get the next episode. Hope you liked episode one, but if you want the whole series right now, support us on Supercast and you'll get everything right now.

[00:28:42] And, um, Further to that. We kind of messaged, like, not only are you doing this to get all six episodes right now, but you're also funding the next big investigation we do. And I was really curious A if anyone would like our content enough to pay, to get it all right away and B, if they would stay and I got positive answers to both of those questions. Not nearly enough to fund the next investigation, but enough that it kind of makes me think that like there's something here and something like 75% of those people stayed on as supporters.

[00:29:25] So if every time we have a new investigation, We have a similar thing on Supercast. And I think we'll also give some bonus content and some followups that are exclusive to our, our paying subscribers via Supercast. I think over time we can build up a, a discreet, um, paying subscriber base specifically for those standalone shows.

[00:29:51] Eventually, our goal is that that will be one of the two or three revenue streams that allow those types of shows to be profitable.

[00:30:03] Jason Sew Hoy: Got it. That's great. So I know crowdfunding week as you mentioned is a key lever, and I think we'll save the details on that one for the AMA after the show. Um, but just in the remaining few minutes, I'm keen to explore a little bit more about the team now. I noticed that one of the goals that you had for 2020 in your transparency  report was to de-Jessefy Canadaland, which I thought it was a great goal.

[00:30:32] And I wanted to touch on this because, a lot of podcasters, as you know, also struggle with the same thing, you know, separating the brand and the eventual organization from the founder. Who's often the main personality. Um, so I wanted to pick your brain on, I guess, the steps as to how you see that unfolding.

How did Jesse Brown separate himself from Canadaland?

[00:30:55] Jesse Brown: How do you de-Jessefy is the question? Yeah. Yeah. I mean, it like. There was a fork in the road.

[00:31:01] And, um, I think that anybody who's built like a business out of their personal podcast has to decide where's this going? Am I just going to build a personal brand out of this? Um, and there's nothing wrong with that. Like I think, you know, Mark Marron, could've gone the Barstool sports way and created a net work of comedy podcasts and spin off TV shows.

[00:31:21] And instead he used it to basically, um, It's a moneymaker for him and a big one. And it also buttressed and resuscitated his career as a comedian and as an actor. So he used that for his personal brand and you know, more power to him. That was the right choice for him. I made a decision. I mean, I've been thinking about this for a while, but like all of my favorite podcast hosts are people who eventually I get sick of, you know, podcasts are about hanging out with someone and just like in real life, like eventually you've heard that person's every story and joke. You just know them, you know, up and down and, you know, it's enough already and I don't want to overstay my welcome. Um, so, and I, you know, the De-jesseficiation to answer your question is sort of a different in different places.

[00:32:04] On my podcast it means the show should be less about me and my opinions and my thoughts on things and more about the journalism and increasingly I'm handing over episodes to correspondence or, my colleague Cachuma Malevich is, hosting episodes that I'm not on at all and we're putting more money into original journalism and into correspondence. So it's already  far less centered  around me. Our chat opinion show that one can be Jessefied. That's OK. Uh, and then on our other shows in the network in the early days, which is, I think common, like any startup really, you know, I had my fingers in everything.

[00:32:45] I was involved editorially, administratively, like I was just involved in everything. And, um, when it's small enough that it's possible to say, oh, let me step in at the last minute and work on this a little bit. Um, you know, you do that, uh, when you're building and then at a certain point, your employees just like are absolutely sick of it and it's not even possible anymore.

[00:33:05] And you know what? You are at a position where you're working with experienced, competent, wonderful colleagues who do not need that level of micromanagement. I'm really lucky to work with the team that we have here. We have really incredible people, both in terms of personality, these who do not need me to be on the shows with them, for them to completely, you know, occupy that space and have just strong personal brands, for lack of a better term of their own, but also behind the scenes producers who are just, excellent.

[00:33:36] Management now who bring to the organization like newsroom experience at some wonderful organizations and, and storytelling abilities. So it's just a huge relief, you know, to, for them. And for me, um, it's not done yet, but we're in the process.

[00:33:54] Jason Sew Hoy: Yeah. And on that note of scaling the team. So you just announced a million dollars in funding from the Tiny foundation, earlier this year, which is awesome. Congratulations on that. I'm interested to know, I guess, you know, what your consideration factors were in deciding to accept that money?

Why did Canadaland accept $1M in funding from Tiny?

[00:34:20] Jesse Brown: Pretty extensive, you know, the possibility of investment or the opportunities for investment came up from time to time. And, you know I wouldn't be much of a media reporter or media critic if I were not aware of the dangers that come with money. Um, so many media organizations, that that's what kills them. You know, you get a big check. Okay. And now you've got a partner who can influence the editorial. You get a big check and now you may be making money, but now you're spending somebody else's money, and it's going to run out one day. And if all of the costs that you're now committed to, they're not going to go away. So now the clock is ticking, you know, you're, you're going to run out of runway. Um, all of these concerns, how would the paying supporters feel? Yeah. You know, why am I going to give Canadaland five bucks a month if they got a million dollars? You know, that was a big consideration.

[00:35:16] So there was just a ton of reasons why we wouldn't do it. And the thing about this opportunity was that the tiny foundation and shared those concerns and was able to allay every one of them. So it's explicit in the contract. They have no editorial influence and they don't have voting shares even. So they can't exert editorial influence through that mechanism either.

[00:35:38] I've let Andrew Wilkinson who runs Tiny know, I'd love to talk with you about business strategy any time, but we're never going to talk about our editorial content. Like I don't even, I don't, I don't even want to hear a compliment, you know, um, You know, there's no ideological bent that I'm aware of to that foundation or to what it's doing.

[00:35:57] And, um, and then to the question of us using the money in a way that could become a liability. I'm just trying to be smart about it. We're not getting a big, shiny new office. We're not drastically expanding the team. The things we are expanding on are things that I would hate to have to contract, but they're contractable, you know, we're just investing in the journalism.

[00:36:18] So we're putting a lot of money into freelancer's hands to do more original reporting for the Monday show. We're going to try, as I was explaining earlier to make more shows like Thunder Bay and then, you know, the money is going to be dispersed over three year period at the end of that time. I really do think it's it's, um, possible and even conservative we've grown every year.

[00:36:41] Anyhow, even before this investment, I have every intention of generating enough revenue that every person who joins us as a result of this investment stays with us. Um, I have every goal in mind to, you know, keep doing all the things that we're doing with this, with this investment, but I don't control the universe.

[00:37:02] Things can happen that we don't even see coming. And if we have to go back to where we were, we'll be able to, and audience will be richer for all of the journalism. We were able to conduct and report with that investment. So that's sort of how we're approaching the money side of it. And then the final thing of like, what would the audience, pull their funding once they learned of this?

[00:37:24] They didn't, they cheered us on, they were so happy. And when they found out that we are making Thunder Bay 2, the sequel that they tried to finance, but just we didn't get there. Uh, they were overjoyed. So now we just have to, you know, make good on our promise and make that show as good as the first season.

[00:37:40] Jason Sew Hoy: I love it. Okay, great. So just conscious of time here. I'm going to wrap up this main segment of  the episode  In preparation for Jesse coming on the show, we also asked our audience for some questions and got some great feedback. So to listen to Jessie's AMA you can sign up for the Supercaster premium feed, which will include insight into Canadaland's crowdfunding week, which has Jesse's mentioned generates an annual influx of new paid subscribers.

[00:38:18] To check it out, head to premium.supercast.com or click the link in the show notes, sign up for free and you'll have the premium Supercasters feed in your podcast player in just a couple of taps. It's premium.supercast.com. and it's a hundred percent free. Jesse, always pleasure speaking with you. Thank you so much for coming on the show today.

[00:38:39] Jesse Brown: It was an absolute pleasure. Thank you for your interest.

[00:38:42] Jason Sew Hoy: That's it folks hope you enjoy the episode. And if you sign up at premium.supercast.com, you'll also get the premium version of that next episode in about two weeks time. 


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