How Jesse Brown took Canadaland worldwide.

Jesse Brown’s Canadaland has been pulling back the curtain on how Canadian media works since 2013. He’s also been ahead of the podcasting curve for years, offering his fans subscriptions long before the subscription model was a proven path to revenue in podcasting. Those subscribers helped Canadaland morph into a full-fledged podcast network, providing funding for investigation-driven hits like Thunder Bay and Cool Mules that have enthralled audiences far beyond the borders of the Great White North.

Known for his candid approach to running Canadaland, Jesse spoke with Apple Podcasts to share his perspective on encouraging audiences to invest (literally) in your work, the evolution of the subscription model, and why today’s aspiring journalists shouldn’t wait for permission to start their podcast. 

Apple Podcasts: Can you explain what led to your journey into podcasting?

Jesse: When I was publishing a zine in high school, I was really interested in the DIY punk culture approach to media. But then I went and became a public broadcaster with the CBC, really trying to fit my point of view and ideas into traditional legacy media. I had an idea for a show in 2013, and the only way to do it was through podcasting, which at the time was nothing like it is now. I worried about devaluing my brand as a national radio host, but I couldn’t get this idea out of my head. Eventually, my wife said, “You either need to shut up about this idea, or just go do it.” I just wish I’d done it sooner.

AP: How did your background as a journalist translate to podcasting?

Jesse: The original mission of Canadaland was to simply do media criticism and reporting in Canada. By necessity, there’s been an element of partnership and transparency to pull back the curtain and show you how the media really works. I talk to my audience about how it’s going and let them know when we’re failing, what we missed, and what our goals are to make them feel invested in Canadaland. And they do actually invest in it. If someone is a paying supporter, they could quite literally take credit for our investigations — some of which have become major news stories — because they helped fund them.

AP: What were some of the obstacles or challenges you faced when starting with subscriptions?

Jesse: If you go back and listen to my early appeals for subscriptions, I sound very sheepish. It took me a while to realize that there’s an audience for what we’re doing, and a significant percentage of them are happy to become paying subscribers if we can just figure out how to provide maximum value.

Our approach to building out and diversifying revenue streams comes from jumping in and cleaning up the mess afterwards if we need to. We’ve been early to some trends, like launching paid subscriptions in 2014 before there was even technology that allowed you to remove ads and provide private streams.

For a while, the workarounds required to offer subscriptions absolutely created friction and limited our ability to convert listeners to subscribers. Apple’s subscription button opened up a whole new revenue stream for us. The user experience, the lack of friction, it’s just so easy.

AP: So how does that long history of developing this revenue stream affect your strategy toward Apple Podcasts Subscriptions and what you want to do with them?

Jesse: One problem in podcasting is that at some point, people started thinking this was Silicon Valley, where success means scaling 10 times or 100 times. We build our business one subscriber at a time. If we grow 10, 20, or 30 percent from the year before, that’s great. I think slow and steady wins the race.

As a podcast focused on Canada, we have a smaller potential audience for most of our shows. But we have investigative stories that just happen to take place in Canada, which have gotten millions of listeners around the world thanks to Apple’s partnership and support.

Building a subscription product specifically aimed at that massive audience for investigations that might take a whole team years to do was really important, which is why we experimented with a $1 a month price point for the Canadaland Investigates channel. In those early days, we would promote it as “hey, it’s $1, and you get to listen to everything now.” But after someone comes to the end of a story, we shift from that first value proposition to one of funding our important mission. They’re almost tipping us in exchange for bonus content and early access to new episodes. That’s actually been as successful as the subscription model for our flagship news and current affairs show. And it has allowed us the versatility to offer different audiences different products at different price points.

AP: How has the subscriptions model fit into Canadaland’s overall strategy as you grow?

Jesse: Overall, subscriptions are at least half of our revenue. I was terrified our paying subscribers would tighten their belts when the pandemic hit, but our subscription business grew because we were giving people news and connection and conversation at a time when people were really disconnected and isolated. We saw that loyalty as an obligation to provide maximum value for our listeners.

People come to podcasts in lots of different ways. When somebody finds us on Apple, we’re trying to move them into an ever more intimate and connected relationship with our brand and our content, and that just allows us to get people in the door in a way that we weren’t able to before.

AP: How do you see Canadaland helping to shape the industry for news media?

Jesse: Over the years, we’ve heard cries that there’s no way to get people to pay for news. But since 2013, we’ve found a way to keep reporting, commenting, and investigating while making money doing it. In podcasting, quality journalism makes money. That goes for both original, investigative work and daily news explanation, which is just a human being helping listeners make sense of what’s going on. It’s an incredible public service that democracy really requires, and also a very successful product. I don’t think that podcasting is necessarily the only solution to the crisis in journalism, but it’s a big ingredient, and sometimes it gets overlooked.

AP: What kind of advice do you have for someone looking to build a business off of their reporting?

Jesse: I just wish I hadn’t spent so many years waiting for somebody else to decide I’m ready to do the job that I want. Give yourself your dream job as your first job. Do what you have to do to get a paycheck, but don’t wait for anyone’s permission to cover the exact thing that you want to cover. Just jump in and start building your audience any way you can, as soon as you can. It’s the thing that a lot of hungry young journalists are most afraid to do. I think podcasting should probably be at the center of your journalistic practice. Say “I’m new to this, and it’s my beat, because I say so. I’ll probably be learning in public and making mistakes, but I’m here to fearlessly ask questions of the biggest people in that field.” Just let your curiosity guide you, and I think you’ll find that people are really open and supportive. It might take five or six years. But at the end of that five or six years, you’ll be an experienced mid-career beat reporter who has good sources and an audience. And whether you’re writing an article or trying to monetize your audience through an Apple subscription, you can take that audience with you anywhere.