May 1, 2023
#880 Terry O’Reilly’s Had It With Ads
Who started the first successful podcast network in Canada? What do 1950s TV and Radio have to do with podcasting? Jesse Brown sits down with Terry O’Reilly, host of Under the Influence, to talk about all things podcasting and advertising.
Jesse Brown
Host & Publisher
Bruce Thorson
Senior Producer
Tristan Capacchione
Audio Editor & Technical Producer

Ads are everywhere in our life and they seem to keep creeping into more and more places. Movies, games, sponsored “news” content, and of course, the digital tracking that follows your every online move to sell you something you’ve already bought. (You know, you can never have enough washing machines.)

For eighteen years, Terry O’Reilly has been studying and explaining human nature through the lens of advertising. His first show, called O’Reilly on Advertising, started on CBC in 2005 followed by The Age of Persuasion in 2006, and since 2011 it continues as both radio show and podcast, by the name Under the Influence, on his own network, Apostrophe.

Jesse sits down to talk with Terry about all things advertising, podcasting, and why some people want to touch their favourite radio show hosts.

Host: Jesse Brown

Credits: Tristan Capacchione (Audio Editor and Technical Producer), Bruce Thorson (Senior Producer), Annette Ejiofor (Managing Editor)


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Canadaland’s transcripts are edited to the best of our ability to ensure accuracy from audio to text. Please contact should you have a correction.


“Mad Men” Clip – Don Draper: Advertising is based on one thing. Happiness. And you know what happiness is? Happiness is the smell of a new car. It’s freedom from fear. It’s a billboard on the side of the road that screams with reassurance that whatever you’re doing. It’s okay.

Jesse Brown: Terry O’Reilly is probably the most famous ad guy in Canada. Which is weird because the truth is that Terry O’Reilly hasn’t actually been working in advertising for years. The guy sold his ad business in 2018, and since then he’s had the same job that I have. He’s a podcast host and he’s the publisher of a podcast network called Apostrophe. They publish a whole bunch of shows, but most prominently is Terry’s show Under the Influence. That is his hit show about marketing and advertising, currently in its 12th season. 

But he’s been at it for a lot longer than that. Before Under the Influence, he hosted five seasons of a similar show called The Age of Persuasion, and before that he had a show called O’Reilly on Advertising. He has been talking about advertising and marketing for a long time, hundreds of episodes examining every possible angle on this industry. For example, an episode called Touch the Pickle: Marketing, Gender Equality. Also, the Commercial from the Black Lagoon: Horror In Advertising. It goes on and on. 

Terry O’Reilly is just endlessly fascinated with his industry, and Canadians seem to be fascinated with it too. I mean, he reaches a million radio listeners a week. He has served 50 million podcast downloads since 2012. There is this huge appetite out there for his insider’s take on the ad business, even if he’s not really an insider anymore, On the ad business. But I don’t know. Maybe it’s not fair to say that Terry O’Reilly left advertising because there’s one product that Terry O’Reilly is still advertising the hell out of, and that product is Terry O’Reilly.

His radio show on the CBC. Works as a permanent national ad campaign for his podcast business. Somehow, this guy convinced the CBC to pay him to advertise his own podcast. And, of course, he sells ads on his podcast. And his podcast is itself a commercial for his books. And of course, he does paid speeches where he sells those books. If any of this sounds like shade, I promise you that is not where I’m coming from here. I mean, I want to know how he did it. Game recognizes game. O’Reilly is not pretending to be doing anything else. He has no pretense about what he does. He is unabashedly involved in private enterprise and somehow he has convinced the public broadcaster to fuel it. 

I have always wanted to get the story of how that came to be. I also happen to like his show. I always find it to be well made and interesting, even when its ethically agnostic attitude towards consumer culture can sometimes infuriate me. And I’m going to get to ask him about that because Terry O’Reilly joins me in a minute in our studio. Wait for it. 

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Jesse Brown: This episode is brought to you by Lillian Moon, Julie Summerfruend, Emily Niles, Allison Buchan-Terrell, Carly Behrens, Simon Peng, Kyle Baron and Brent.

Patron Supporter Brent McGarry: Hi, I’m Brent McGarry. I work in the fintech industry in Calgary. I support Canadaland because of the in-depth and captivating storytelling I experienced in Thunder Bay and Rat Fucker, for the investigative excellence done by Arshy Mann on Commons and for all the other contributors like Mattea Roach, Jonathan Goldsbie and Emile Nicolas. Thanks for all you do.

(Patron sting plays)

Jesse Brown: I want to get into a fight with you about which one of us was the first to start a podcast company in Canada, I think maybe you. 

Terry O’Reilly: You’ll win.

Jesse Brown: Was it me?

Terry O’Reilly: Yeah.

Jesse Brown: I don’t know. Because you had a company called Pirate that made your first show.

Terry O’Reilly: Yes, but Pirate was a commercial entity. In other words, our biggest clients were advertising agencies. So what Pirate did was we created radio campaigns from the ground up, and we directed the voiceover sound and music for television commercials. It was all advertising.

So when in 2005, when we pitched the show to CBC, I had studios. The audio was my skill set, so I just thought, I’m going to do it at our studios. So for the first probably until about 20-, I want to say 2011 maybe, or 2012. I did it at Pirate and then I built my own studio and did it from there.

Jesse Brown: You built Apostrophe, and you built Apostrophe as a podcast studio.

Terry O’Reilly: I started podcasting Under the Influence in 2011. I wanted to podcast earlier than that. I was ready to go probably three years earlier than that, but I kept waiting for CBC to clear music rights.

Jesse Brown: I figured out the first time we spoke. I misremembered it as when I was setting up Canadaland, but that’s not the case. It was after my first series with CBC. I had sold them on the idea for a second series, but I didn’t really trust them. And I was wondering like, do I have to go back to work there to make a CBC radio show? Is there another way to do it?

Terry O’Reilly: Right.

Jesse Brown: And I thought, well, Terry O’Reilly has a CBC radio show, but it doesn’t work at the CBC.

Terry O’Reilly: Right, Right.

Jesse Brown: And you were nice enough to speak with me and let me know that you had this Pirate Radio Company and that you had your own team of people and you independently produced this thing, and then you sold it to the CBC. And that sounded terribly complicated to me at the time. So I went back to work for the CBC.

Terry O’Reilly: You know, that part of my story is so funny because when myself and Mike Tennant, who’s another radio guy, when we pitched my radio show idea to CBC, not thinking CBC would ever buy it because why would the advertising free CBC take a show on advertising? They took it, which was shocking to us.

And then we had to figure out how to mount a national radio show. But in the negotiations, we negotiated to own the show and license it to CBC. Not that we were such savvy negotiators, Jesse. Because I thought that’s the way it’s done. It was just naivete. But now I own my show, which is fantastic, but it was not a grand plan.

Jesse Brown: I mean, it’s an incredible thing whether it happened by luck or by strategy. And I remember one of my bosses at CBC talking to me once and saying, They’ll never do that again, not with reference to you, but we were talking about Stuart McLean.

Terry O’Reilly: Right.

Jesse Brown: And I said, What? And she said, This guy negotiated ownership of his show and the intellectual property thereof, and he went to them and said, I want to have the rights to do live shows and put out CDs. And they thought, Well, no one’s ever done that. Like, you can have those rights. They’re worthless to us because they weren’t exploiting those rights. Right. And what ended up was he built and here the pun is intended a cottage industry.

Terry O’Reilly: And he was an industry.

Jesse Brown: Yeah. You make a podcast about marketing. Let’s talk about podcasts as marketing, because at that time it was a radio show, but I can’t believe that the CBC was paying him to make a show that they broadcast across the country. And then he goes from town to town doing big live shows, selling out, selling his books there.

Terry O’Reilly: CDs, everything. He took a busload of people across the country, and then he would swing through the northern states. He had an audience in the States, too.

Jesse Brown: If they had flipped it on him and said, From now on, you’ve got to pay us to keep the Vinyl cafe, it probably would have made business sense.

Terry O’Reilly: He might have done it, yeah. He might have done it. It’s sort of like the Star Wars story, isn’t it? When George Lucas nobody wanted Star Wars. Everybody knows this story. But the interesting part of that story to me is he really wanted the licensing part of the deal. He saw the future, that he could do a lot of toys and things coming out of the show. And the studio just laughed their heads off and said, Take it.

Jesse Brown: Yeah.

Terry O’Reilly: Thinking it was it was worthless.

Jesse Brown: And you have a similar thing going,

Terry O’Reilly: Yeah. 

Jesse Brown: I would take that. Like if CBC said, we’re not going to pay you a dime –we couldn’t do it with Canadaland because we covered the CBC – but we like Commons, let’s say. We’re going to air it on CBC Radio One to every community in the country that would spike our podcast downloads. They can have it for free. I probably would even pay them something for that. So you got a sweet deal. You’re like your model is the Stuart McLean model. And I don’t know, maybe there’s a couple other people who sell content to CBC that way.

Terry O’Reilly: But I don’t think there’s many though.

Jesse Brown: That’s a wonderful deal.

Terry O’Reilly: It is a wonderful deal. And as I said, just sheer serendipity, luck of not knowing any better.

Jesse Brown: Because what do you know about marketing?

Terry O’Reilly: What do I know? Exactly right.

Jesse Brown: Getting back to the content and the culture clash of your work, which I think takes an explainer and an insider explainer and a curious approach to advertising and marketing. And I don’t know, you’re on the 12th season of this series. And then there was the series – 

Terry O’Reilly: All told this is our 18th season since we started.

Jesse Brown: 18 Seasons of examining commercial culture-

Terry O’Reilly: Right. 

Jesse Brown: On the CBC.

Terry O’Reilly: On the CBC.

Jesse Brown: I once did a documentary about marketing when I worked at the CBC, and I was told like, there’s not enough of the negative effects on culture and on society. If you’re going to talk about marketing, you can’t seem this positive about marketing.

You know, I appreciate like we live in a very commercialized marketing-heavy society and, you know, I see value in having one place that considers itself a bit of a temple free from the pernicious influence of advertising and marketing, which is an interesting contrast to their podcast today, which are filled with ads. But we can leave that aside for a second. But there was a real moralizing like, you can’t even talk about this. 

Terry O’Reilly: Which is why I was very surprised they took our show.

Jesse Brown: Yeah, me too.

Terry O’Reilly: I thought going up the elevator that day, our pitch was basically this. Jesse, it was really simple. We basically said, most people hate advertising and it’s like architecture. It’s everywhere in your life. But actually, when you dig down into it, advertising is a fascinating industry because it’s the study of human nature and nobody studies human nature like the advertising industry. And I said, Mike and I are not pundits and we’re not journalists. We’re actually working admen in the trenches. We have access and we have stories, and we want to take people – we want to take average Canadians, not marketers – on a backstage cook’s tour of what really happens in the boardrooms and the recording studios. 

That was the whole pitch going up the elevator that day. Mike and I looked at each other and I thought, They’re going to say, Very interesting. Not for us, but very interesting. Maybe we could do something else down the road. That would have been a great meeting. But instead, Chris Boyce, who was in charge of radio at the time, he leaned back in his chair and said, We’ll take it. And then we had to figure out how to do it. That was 18 years ago.

Jesse Brown: It’s an interesting way of thinking about creativity and creative people because we’re obsessed with artists and writers and people who look at communication as a way of personal expression. And here you’ve got people with very similar skill sets, right in a very purpose-oriented. 

We’re trying to solve-

Terry O’Reilly: Business problems.

Jesse Brown: Solving business problems with images and feelings and emotion. And I don’t know something about taking any kind of like, moral judgment out of it allows you to, well, first understand what they’re doing. I sometimes get left with like. I admire these people like and I think a lot of people got into this. I mean, you started before Mad Men, but with Mad Men people, it became kind of like fun to think about how these people work, how-

Terry O’Reilly: Think we got a big updraft from Mad Men, believe it or not.

Jesse Brown: I believe that.

Terry O’Reilly: I think people just got into it. You’re right. You got into the whole fun of Madison Avenue and now that was there a specific but I’ll say this about that show. Matthew Weiner had somebody on that staff that had worked in the business.

Jesse Brown: Yeah.

Terry O’Reilly: That show – the dynamics of advertising, meaning the client relationships, the dynamics inside an agency, the pressures, the deadlines, getting fired by – all of that was real. So that was a real uptick for people getting interested in the industry, which helped us.

Jesse Brown: Maybe this is a little bit of a digression, but I always wonder this. When I’m listening to your show, you’re talking about the creative minds who are coming up with the campaigns.

Terry O’Reilly:

Jesse Brown:
But you’re doing that from Canada, and correct me if I’m wrong, but my understanding is that a lot of the time that creative work is done in the States, they come to Canada and then they just make a media buy.

Terry O’Reilly: Uh…. yes? There’s still a lot of highly functioning Canadian advertising agencies putting out work. The toughest thing for me in my show is finding the stories about Canadian campaigns. The US keeps everything. I can find the first radio ad done in 1923 with three clicks of a mouse. I can’t find anything in Canada. There’s no archive.

Jesse Brown: Oh.

Terry O’Reilly: It’s really frustrating for me. I mean, because I spent my career in the business. I can call up ad people and say, Tell me about that campaign you did. Or I can call up retired creative directors and say, Remember that campaign you did in 1983? Tell me that story. But it’s really frustrating for me because there’s no archive in this country, in the States, there’s the Duke archives at Duke University that are endless. And there’s all –  anyway, there’s a ton of archives there. The US has kept everything. They really bought into Marshall McLuhan’s line that advertising is the cave art of any era, and here it’s not the case. So it’s an ongoing struggle for me to find Canadian stories, which I’m always looking for.

Jesse Brown: I’ve never thought about that once. That’s so fascinating. And it’s it’s true. When you look back, you find like an old dusty magazine at somebody’s grandmother’s house or in their cottage or something. It’s the ads that tell you so much.

Terry O’Reilly: Pirate donated a portion of our archives to McMaster University. We donated 50,000 commercials, which was only probably a third of our archive.

Jesse Brown: Of what you made.

Terry O’Reilly: Of what we made. Yeah.

Jesse Brown: You made 50,000 commercials?

Terry O’Reilly: We made way more than that. That was a third of our archive was 50,000. But why McMaster was interested in it was because inside that archive was the first cellular phone advertising, there was Olympic advertising, there were federal election advertising, the first AIDS PSA. Like all of that was reflected in that archive because advertising is the great mirror of any era. Like you said, you look through your magazine, you can tell what clothes someone’s wearing, you know exactly what decade that is.

Jesse Brown: Wow. But in Canada, we’ve lost our heritage.

Terry O’Reilly: Yeah, there’s just no hunger, no desire to archive at all – yet.

Jesse Brown: I listen to your show recently and you tried to sell me weed.

Jesse Brown: Yeah.

Terry O’Reilly: No judgment. Yeah,  yup.

Jesse Brown:  I sell mattresses. I sell supplements. I once sold a monthly meat box subscription.

Terry O’Reilly: There you go.

Jesse Brown: How do you think about podcast advertising?

Terry O’Reilly: Well, we’re trying to monetize our podcast the best we can because it keeps our company healthy and it allows me to pay people what they’re worth. So it’s important to us. And I you know, I’m in the advertising business, so I’m a big fan of advertising. The interesting question about cannabis and even gambling casinos is there are new categories, right?

What we do is we take a look at everything that comes across our table and we decide whether it feels right to us. Cannabis, I don’t have a problem with it’s legal. There’s stores, there’s retailers. I don’t have a problem with it. Casino stuff is starting to come in, we’ll have to see how that goes.

Jesse Brown: That kind of talks about the comfort question and the like, is this do I want to put my name on this? What do you think about the industry that we’re kind of you know, I’ll say it, we’re pioneering the podcast industry. We were in it a long time ago, and it’s amazing to watch an industry go from nothing to a multi-billion dollar industry and to kind of try to navigate that. And it feels very new and fresh at the same time. There are strains within it which feel like it’s a return to like 1920s radio or something.

Terry O’Reilly: So true when hosts are asked to read ads, it feels like it’s the 1940 radio and that’s what everybody wants. They really don’t want a slick presentation and they’re not really looking for conceptual ideas. They really which is interesting to me because I came out of an entire career of trying to add a conceptual selling idea to an ad.

Advertisers don’t seem to want that. They’re hoping for endorsements, which I don’t really do. But what’s also interesting about podcasting I was reading this week, Jesse, I don’t know if you saw it. Podcasting is reaching 18 to 49. I think it is age-group almost on par with AM FM radio and linear TV this year. That’s huge, right? That almost makes podcasting a mass medium.

Jesse Brown: That’s incredible. And radio is something that doesn’t get talked about. As mass media. But in the early years of podcasting, it was always like, Wow, we’re 3% of radio. Like, radio has been so resilient. It’s like a tank. Just this really-

Terry O’Reilly: Cannot be killed by conventional weapons. That’s right. It really stays like it survived everything, right? It survived television and movies and the Internet and the numbers are still pretty good for radio.

Jesse Brown: You know, it’s still very much mass media and millions and millions of people. Will we kill it?

Terry O’Reilly: I love the transition from radio to podcasting personally because I could tell stories. I had no time factor. Even our podcast version of our show is usually longer than our CBC version of the show because like, I don’t have to be 27-30. So the storytelling gets better with podcasting. For me.

Jesse Brown: My first media job was as a co-op student at Q 107, and the most sort of beleaguered member of that staff was the copywriter for their ads. And it was it was so old school that you just have some hack kind of – I don’t mean to put the guy down – but he just looked like such a sad sack. You know, those radio ads, like the quality of the experience of listening to FM radio and then you get that block of ads.

And it was interesting because these days you think about the tight brand controls that companies have. And here was this guy who was just like, you know, the radio ads like, “Hey, Jan. Yes, Jim,” let’s head down to the Honda dealership. And he just had to pump these things out. And I’d get pulled into the studio because they need like four people to, like, laugh or yell at a certain point or say, one line. And the guy was just he was amazing.

Terry O’Reilly: I started that way, Jesse. So my first job was at FM 108 Radio in Burlington in 1981. It was the only 50s and 60s radio station in Canada at the time because oldies were just becoming oldies, right? I was the sole copywriter and production guy for the entire radio station. So we had about 150 ongoing retail clients at any. And it’s all local advertising, right? 

Some days I’d write 25 or 30 commercials a day. I would then need someone to voice them. So I’d stand outside the morning jock’s door at 9:00 when he finished and drag him into the studio to record. And if we needed a second voice, I would do that second voice. And if I needed a third voice, I’d record that voice to put my finger on the spindle – tape days – slow my voice down. So it sounded like just three of us in the room, like all of that. But I had to pump them out so fast. Yeah. Jesse, that’s why they don’t sound so great because the volume is crippling.

Jesse Brown: I think that’s a big factor. But to the kind of complaint, the listener complaint of just how corny they can sound, there’s a reason for that on FM radio like to try to just grab people’s attention in the first second, you know, And I was kind of given a crash course in this stuff. It’s interesting to contrast that with the podcast ad format and the kind of fork in the road, we’re at right now, because I’ll admit something here, I like reading ads. I kind of feel connected to, George Burns, like, what’s Gracie getting up to next? Well, first, a message from Lucky Strike. I love the flavour of my Lucky Strikes.

I understand that what a podcast is doing is taking a listener into to a conversation. There’s an intimacy and you’re saying, Hey, sit down with me and this other person and you get a seat on the couch while we have an interesting conversation and to have some other message come in and be like “Today”, you know, “Sunday, Sunday” is too –

Terry O’Reilly: It’s jarring.

Jesse Brown: It’s severing that. And we kind of specialize. We’re probably the only news podcaster where news personalities will read ad copy right? And that’s a bit of a killer feature of an hour. I’ll advertise for our ads. We hear from our advertisers like, Wow, your stuff converts 2 or 3 times as well as when we have our fanciest marketers put together a beautiful, polished, prerecorded with actors.

Terry O’Reilly: Yup, with trained actors, Yeah.

Jesse Brown: Because now they’re dynamically inserting ads and podcasts and we do a little bit of that for unsold inventory. And as a listener, like, it’s a very different experience.

Terry O’Reilly: You mean the run-of-schedule stuff that is pre-produced that gets dropped in? Yeah, yeah, yeah, yeah. That’s that’s an interesting notion. You know, it’s in the advertising world, you try and not sound like the station you’re on. In other words, you purposely try and leap out of the radio sounding so different from the environment you’re in.

When I talk to radio station owners and programming chiefs over there, they always told me, which is very interesting, we give preference to ads that sound like us. So we were kind of working at odds. It took me deep into my career before I realized that they actually would give preferential positioning, meaning the first ad out of the programming in a break. That’s the best place to be. Two ads that sounded most like their format. I spent my whole career trying not to do that.

Jesse Brown: You were fighting them?

Terry O’Reilly: I was fighting them.

Jesse Brown: I think that tells you something about the difference in the listening experience that radio is ambient and becomes wallpaper, and an ad needs to somehow it has to poke you in the ear and get your attention. Whereas I think a good podcast, there are some podcasts that I think kind of play the ambient thing, like a three-hour rambling. Joe Rogan thing,

Terry O’Reilly: Right?

Jesse Brown: Throw it on. Forget about it. But if you’re producing and you specialize in highly produced, scripted narrative radio, it’s the kind of radio where you want people to like if they got home and they’re still five minutes left.

Terry O’Reilly: Stay in the driveway.

Jesse Brown: That’s it. Yeah. So why break that spell when it’s time to deliver?

Terry O’Reilly: I know, I know. I even wrestle with the transition going from our show to our commercials, what that bridge should be, or should there be a bridge? I think we’re both on Acast. Acast has a little mnemonic they use when they go to. And I wonder I wonder if that should even be in there. Like I’m just constantly just thinking about that. Should we burst the bubble, as you say, or should we just transition right into the commercial so you don’t take somebody by the collar and say, we’ll be back in five minutes, you know.

Jesse Brown: We have different priorities because we as a newsroom want there to be like absolute clarity as to when you’re listening to our editorial content and when you’re listening to an ad.

Terry O’Reilly: Right.

Jesse Brown: And there are things that we’ll do that the other guys won’t do and they’ll consider it. Like the idea of, again, having a news personality read an ad is anathema. And I’ve had senior CBC colleagues tell me like, “ I’ve been at this for 35 years and I’ve never read a goddamn ad,” like a very badge of honour. Yeah, yeah. Unless we have an objection to an advertiser or unless there’s a conflict of interest, I’m into it. You know, like, I’ll give the personal endorsement if there is a personal endorsement.

Terry O’Reilly: Right.

Jesse Brown: To be made.

Terry O’Reilly: Right. I have to be careful of that. The way you have to be careful. You probably don’t take on any media advertising, right? You wouldn’t take on Global –

Jesse Brown: On the Canadaland show, we cover them. And so we. So we wouldn’t take that on that ad

Terry O’Reilly: So you wouldn’t take that ad. I have to be careful, too. With endorsements because I may be doing a story on that brand two months from now.

Jesse Brown: Right, you’ve got your lines in the sand.

Terry O’Reilly: Yeah. Because if I say something great about that brand and I’ve endorsed it two months ago, it just even though it’s legitimate and there is no funny business going on, it may not seem that way to them.

Jesse Brown: Well, you don’t want the listener wondering if you’re doing a half hour looking into Nestlé’s great campaign because they also bought a big block of ads on…

Terry O’Reilly: Right.

Jesse Brown: Yeah, so that’s that’s the same thing like I I’m for sale when it comes to ads but the listener absolutely can never wonder –

Terry O’Reilly: Right. 

Jesse Brown: – is this an ad that I’m listening to. Yeah and they can never wonder – is his coverage influenced by the ad? So that’s where we kind of set those.

Terry O’Reilly: Yup.

Jesse Brown: It feels quaint in a certain way, talking about these lines because we live in a culture where those lines –

Terry O’Reilly: Google blurred that, don’t you think? I mean, there was always church and state in my business. So, you know, you would never put an ad, or the publisher of a magazine would never put an ad, beside a story that had something to do with that advertiser. Like they would put you further into the magazine. They would never.

That was advertising from the 1920s to whenever Google showed up. And then Google makes a multibillion-dollar business of putting ads right beside content. Like it’s kind of interesting to me, like if you’re searching something from Canadian Tire, right beside it might be stories about Canadian Tire on Google, right?

Jesse Brown: That’s true. That’s interesting.

Terry O’Reilly: And that was their model.

Jesse Brown: You know, it’s also another way of thinking about conflict of interest because newspapers were protecting conflict of interest from the advertiser’s point of view. If we’re taking Canadian Tire’s money, yeah, it would not be fair to put their ad next to a story that was negative about them. Right. But we have to be able to report on them. So there was always a newsroom concern of like, you know, and sometimes they would miss it. And there’s some funny instances where you’d have like an ad for a raincoat next to, I don’t know, the raincoat factory is just burned down, Right? You know-

Terry O’Reilly: Child labour, yeah.

Jesse Brown: Yes, yeah. There we go. You got it. And for the advertiser’s sake, you would put that somewhere else, right? But I never thought about that Google, there’s no such and it’s all done algorithmically.

Terry O’Reilly: Anyway. It is. And the next story down from Canadian Tire might be a story about how someone hates Canadian Tire. Like they’ve really blurred that church-and-state thing completely made a business model of it and probably has one of the biggest businesses in the world as a result.

Jesse Brown: I wonder if it’s a question of blurring it to the point where people don’t notice or if it’s a question of like, people are smart, they’re smarter than they’re often given credit for. And it’s kind of funny to see the Nike ad next to an article that’s exposing child labour in sweatshops, and you might take a screenshot of that. And there’s an irony there.

Terry O’Reilly: Right?

Jesse Brown: But it doesn’t have the same ironic quality if you search for Nike and then there’s like sponsored links at the top for Nike, and then there’s some articles, it’s just like, that’s just what Google gave you, right? And I think that people understand that. Yeah. You know, we talk about this in our coverage of this ongoing debate about how, you know, the big tech stole the ads. They stole the ads from the news. And I’ve never been able to feel terribly injured by having the ads stolen from the news because I kind of know that the news and ads was always a bit of a tortured relationship, right? To begin with, it wasn’t the greatest way to like and advertisers never wanted to be next to real news. They never wanted to be next to war and conflict and people getting killed or like real social issues or politicians being scandalized. That was never a great place.

Terry O’Reilly: In network television, CBS, NBC, ABC, the news programs were the highest-rated programs, therefore the most desirable for advertisers, right? But ironically, yeah, you don’t want to be too near a war story yet. The most eyeballs are on that war story.

Jesse Brown: It’s a good point. And that’s the strange cognitive dissonance of having, you know, the world’s going to hell now go buy something. So this struggle to determine where lines should be and what’s fair game, some of those arguments are like settled. And it’s almost strange to tell my kids like, yeah, actually, when they first started putting ads before movies, that was a big deal and people were really upset.

Terry O’Reilly: Do you know why? I have a theory about that. There is a great unwritten contract in advertising, and that is if you’ll sit through this ad, Jesse, I will do something for you in return. So you know the ads in a magazine, pay for the editorial, the ads in a newspaper, pay for the reporters. The ads in television show pays for the production of the sitcoms. Even a bus shelter is a return because you’ve got ads in the bus shelter, but it’s keeping you out of the rain. Movie ads gave you nothing. The price of tickets didn’t come down. Yeah. They broke the unwritten contract. That’s why people were so angry at that.

Jesse Brown: I was furious. You know, not only are you not giving me something, but you’re taking something and you’re not taking just a minute. Those ad blocks became 20 minutes long-

Terry O’Reilly: I know. 

Jesse Brown: Nothing in return. And that was how I, as a struggling student at the time, justified sneaking into the movies. I was like, All right,

Terry O’Reilly: Okay, you can play that game. I’ll play this game. Yup.

Jesse Brown: We’re going to even the scales. But we used to have these debates about a million things, and it was egregious. The first time you would hear the singer-songwriter who you love, Bob Dylan’s song on an ad or an ad in a video game was a really big deal. Or when sponsored content first became a thing. Are you kidding me? This article is a paid article. It was scandalous and bit by bit we’ve eroded that outrage to the point where it would be hard to explain to a kid why we were even upset about that. Because they accept that we are in a completely commercialized world. Where what do you mean a band is trying to make money, right?

I don’t want to get all moralizing on you in the way that I was moralized when I wanted to look at marketing on a documentary. But after 18 years of really removing any kind of like judgment, right or wrong, and just trying to understand advertising and marketing, do you – Terry O’Reilly – look around the world as it is become increasingly brand focused, corporatized, commercialized and say, Enough with the goddamn ads already.

Terry O’Reilly: I do. I do feel that way. I feel that way even when I watch a hockey game. If I could wiggle my nose, I’d take all the ads off the boards. I take all the ads off the ice, leave the playing surface clean. There’s a lot of instances where I think it’s just gone too far and too much, and advertising becomes its own worst enemy. 

Even the algorithms I have always railed against, which makes me sound rather like an old ad guy. But I never liked the ad algorithms because it’s kind of like a submarine chasing you, like you don’t see it and you don’t know that it’s charting all of your online buying activity. Or if you know, you’re you’re looking at car dealership ads and you’re you’re looking for a car. And then when you go to financing, then all of a sudden you get all these offers from Ford because they’ve been waiting for that moment to send you that algorithm. I think that is terrible for advertising. 

And you’re sort of seeing it now. Apple has privacy, things kicking in now, and they’re not going to allow a lot of tracking. And I think that that was inevitable because it was terrible. It was a terrible idea. I understand why marketers loved it, why advertisers loved it because they’re getting all this free information and being able to track people in the buying process. But it gave advertising a black eye.

Jesse Brown: Are you a philosophical guy? Like there’s a whole conversation about how the culture of ultra-commercialization gets into people’s identities. And, you know, and it’s interesting Under the Influence, which it’s interesting that actually, you know, the phrase itself is about being drunk but being intoxicated. Right? But now, of course, influence has a different connotation because everyone’s an influencer or we live in the age of the influencer.

Terry O’Reilly: That’s why part of the reason why we change the name of our show. So the show was Age of Persuasion in the early days. I mean, our show started before there was an iPhone, before there was YouTube before there was Twitter. All of that didn’t exist in 2005. It was still a persuasive industry, I had to persuade you to buy something. It was let me just shovel all of this onto you as an advertiser. Then when the digital world came in, it really became a lot more subtle algorithms, influencers. So really in 2012, we changed the whole format of our show to reflect that.

Jesse Brown: Yeah, it’s a broader category and a more current one because to persuade someone, yes, it’s sales-ey, but you’re having a conversation with them and you’re making an argument. Influence is not necessarily a conversation. Influence is pervasive. And we surround you with values and images and little signals to slowly influence how you feel about things.

Terry O’Reilly: But in one way, it is a conversation because in the old days of persuasion, it was a one-way conversation. You really couldn’t talk back to an advertiser.

Jesse Brown: Right.

Terry O’Reilly: In this day and age with social media, you can talk back to an advertiser, you can get the president of a company’s attention as a 12-year-old girl on Twitter if you had the right message. So there has to be a lot more transparency now, not that there’s total transparency, but you can see someone who has a problem with a marketer, puts it out on Twitter, for example. Then we get a front-row seat to see how they react to that.

Jesse Brown: I think it’s a valid point that the people have a bit more of a voice and we’ve seen, you know, funny stories of brands that get it wrong and somebody they just become a laughing stock and people take turns dunking on them. But, you know, there’s always a period where there’s a bit of chaos and the power gets unsettled and then the Empire Strikes back and they figure out and Wendy’s gets funny and starts making fun of McDonald’s and they kind of co-opt, you know, the rebel voice. And the predominant theme is very different than like as a Gen Xer. When we used to say: Oh, that band sold out. 

And now I look at the YouTubers, who my kids are watching and it’s like everyone wants to sell. Like that’s the dream. It’s like. “wow, this guy is an influencer. All he does is he gets stuff for free. Yeah, and we don’t care that he’s getting it for free or why he’s getting it for free and oh my God, they’re paying him and. 

Well, is he only saying that because they’re paying? No. Like, the cool thing is that he’s getting paid. Right. And in a wider sense, what is like, I don’t know, Instagram culture, but everybody advertising a version of their lifestyle. So like the way in which we’ve internalized brand and-

Terry O’Reilly: Everybody is a brand.

Jesse Brown: Now, everybody is a brand that is to a certain perspective, hell.

Terry O’Reilly: (Chuckles) Well, it is if you if you’re going to buy right into it because then you have to cultivate and curate your life. Yeah, right. And there’s a lot of that going on. There’s no doubt about that. I mean, you know, we hear interviews and stories all the time about how it’s negatively affecting a lot of especially younger people, that they feel they look at those wonderful lives and think my life is nothing like that and then can suffer depression and things could get worse. So there’s a lot of downsides to it.

Jesse Brown: Do you think it’s like. We need better regulation.

Terry O’Reilly: I don’t know how you would regulate that. Like when you ask me that, what do you think when you say that? Is there a way?

Jesse Brown: Well, they’re trying. They’re trying with really broad strokes to just basically take kids off of social media, you know, And uh-

Terry O’Reilly: Good luck with that.

Jesse Brown: Yeah. Opt-outs and parents having total access to their kids account. That’s you know, is it Ohio has a has a rule now and there’s a really strong reason to be worried about that. You know, you talk about, let’s say a kid who’s come out to a community of friends as queer and their parents don’t know about it yet. And you’ve legislated that the parents have access to every one of their accounts, or you cut off somebody’s access to a community that’s actually helping them. Like there’s a very reductive view that it’s only negative and in knocking every kid off. 

And then of course, like you say, good luck, they’re going to find some other way. Yeah. So no, I tend to agree like in government doesn’t tend to be super good at this. Like, I don’t know, it’s not a topic I know a tremendous amount about. I know there are laws around disclosing sponsorship.

Terry O’Reilly: Yeah, and that is a big law. If you’re an influencer, you’re supposed to disclose that you’re being paid for that. I mean that there’s big fines in the US. I’m not sure how much it’s it’s done in Canada, but if you don’t disclose that you’re being paid or you’ve gotten product in lieu of the endorsement, it can be a big problem. Some people have been fined big amounts of money.

Jesse Brown: Yeah, so you know, there’s a place for regulation there. And then when it comes to kids, I know there’s like all kinds of little specific things. And of course, when you get to dangerous products, there’s you, right? I don’t know. I guess they can do something. I don’t want to just say forget it. But I guess I tend to feel like we have to work this out in the culture.

Terry O’Reilly: Yeah.

Jesse Brown: I know the ad industry, like every other industry where there’s been a moral panic, turns to self-regulation. To get ahead of the regulators.  So you’ve got all these ad boards and internal mechanisms, you know, but the technology has moved so much faster than people’s understanding of it or these regulatory bodies.

Terry O’Reilly: That is so true. I mean, think about all the changes that we’ve seen in just the last few years in the digital world. I go back to the era, Jesse, where my first radio job I was telling you about all the sound effects were on vinyl records. 

Like I’d have bird chirps, door barks, you know, pull them out, put them down, drop the needle, find the right doorbell ring, run into the studio, transfer it to tape. Like all of that was gone. Yeah, it’s all gone now, right? Editing with a razor blade and a wax pencil. I mean, it’s moving so fast now that you almost can’t keep up. Like, look at the TikTok thing that’s going on now with governments suspecting that TikTok is really this very sticky, addictive app to gain information.

Jesse Brown: Right, is the accusation,

Terry O’Reilly: Yeah. Is the accusation.

Jesse Brown: Yeah, that’s right. And I mean it would be fascinating to do an under the influence on this stuff but I don’t know that we can or you know. I challenge you to do so when we’re talking about things like, you know, your show is so much about getting into the creative human process of people who are, you know, artists in their way, creators, how they’re shaping these things and having fun conversations about how to reach people and looking at the market. And that is a process that is rapidly getting automated and subjected to automated AB testing where, you know, the question of should we go with this message or should we go with that message? The machine is giving us the answer. It runs both messages and it tells you which one won. And then the generation of the messages themselves is increasingly going to be automated by artificial intelligence. Right. And we’re getting to a place where how do you tell the story of an algorithm’s rapid-fire decision-making?

Terry O’Reilly: I know it’s it makes it tough on me. And where’s the creativity to like with all that automation, is there going to be creativity? Is creativity going to become a thing of the past? Is advertising not even going to want creativity anymore? Is it the math man and not the mad men anymore? Like, what’s that going to turn into?

Jesse Brown: It’s very hazy. The AI itself, I don’t think can be considered creative because it is just shuffling existing materials. Yeah, but the creation of the AI is the act of creativity, right? And the writing of the algorithm, which we increasingly talk about as if it’s just sort of like handed down from the mount. 

No, somebody actually said, this is what this line of code should do. So the focus shifts as much as we pat ourselves on the back in this conversation. It’s my fault. As pioneers of a new digital media, I kind of feel like we have something that has a lot more in common with the past than with where things are going. And everything from the host-read-ad to simply asking people to sit down with us for 20, 30, 40 minutes and listen to a conversation or a story. I love how quaint and anachronistic that is. Like, attention spans are getting divided and subdivided and subdivided.

Terry O’Reilly: In some mediums. Right.

Jesse Brown: So we’re the holdout. I can’t think of anywhere else. I know. And that’s the one thing.

Terry O’Reilly: That’s maybe I mean, movies are still two hours long.

Jesse Brown: Movies are the closest. And that’s actually the answer I get when talking about podcast advertising. I say, listen, we price our ads accordingly because where else can you get 60 seconds of a person’s time to hear about your product?

Terry O’Reilly: Totally, 60 seconds were the yachts of advertising and disappeared in the 80 seconds. Advertising went from probably two minutes back in the day being embedded in Jack Benny’s show, where he talked probably for 4 or 5 minutes down to 60 seconds, down to 30 seconds, down to 15 seconds, down to ten seconds, down to six-second YouTube ads where I never really bought that. I understand that it’s more efficient as a media buying. You can buy a lot more small chunks than big ones, But there’s no creativity. There’s no brand building in that, and it’s not enjoyable. It’s like getting a slap across the face really quickly. There’s no real creativity. There’s no interesting you know, I always say connect the dots when you have a brand that every little touch point is an opportunity. All of that goes away in that scenario, which I think is terrible.

Jesse Brown: And it’s not just advertising. The notion that you have a split second to grab somebody’s attention or else it goes somewhere else, They’re making movies that way. You know, the Marvel movie format, the pace of these things is like they’re just slapping you in the face again and again and again, and you can’t build tension. They can’t create any like the quiet moments that make the loud moments work. Right? Because it’s just it’s just pummeling you constantly, really.

Terry O’Reilly: And if you want to carbon date that that’s really as a result of MTV because all that fast-cut editing when MTV showed up I mean that totally influenced my industry. Like once we saw that you can get 30 cuts in 30 seconds, which we’d never even thought of before we started doing that. And then you can see that that ball rolling down the hill in affecting advertising and movies and television shows and Miami Vice and all of that. Right?

Jesse Brown: So I’m a cranky old man because I feel like I’ve found this little lonely island of podcasting, that it’s still this immersive, long-form experience.

Terry O’Reilly: Well, I wouldn’t call you a lonely old man. I think it is. I think it’s a wonderful thing. I think the very fact, as you said, that you can spend time with somebody. It’s a funny thing. When I would do what they called upfronts with CBC. And for those who don’t know what that is, that’s when they parade out all the hosts for all the shows in front of advertisers or in front of an audience, and they get to talk about all their shows and then the public gets to meet you. So it’ll be held in the Eaton Centre or something like that. |

I would watch people come up to the television hosts and they’d be very tentative and they would sort of back away and be afraid to talk to them. And when they came to talk to us radio hosts, they were always touching me. And I was really uncomfortable with it at first. Like it always shake hands but not let go or hold my hand and my elbow or put their arm. It was a strange thing that I was really uncomfortable with, and what I came to realize was it was that thing about audio, Jesse, that people feel connected to the hosts personally, connected to the hosts, because we spend time with them because it’s a voice in their ear. It’s not really a communal event. It’s really a one-on-one. Television has a lot of aw, but audio has this real sense of connection, and that’s why they were always touching.

Jesse Brown: You’ve heard the term Parasocial relationship. No, that’s what people have with their favourite. I have it with my favourite podcast hosts. I mean, you bring them into your home, you bring them in as you’re washing the dishes or as you’re driving in your car by yourself. It’s one on one, as you say. And it’s like a pretty regular thing, you know, It’s like once a week or something. So yeah, people feel like they know. They know you. I mean, people have been you have been in people’s homes for 18 years.

Terry O’Reilly: That’s right. That’s right. And I came to realize that it was an incredible compliment. That when people had that kind of that familiarity with you, that they could cross that line and come right into your zone. You know, and I actually got to like it after a while. I really, truly did.

Jesse Brown: Touch Terry O’Reilly.

Terry O’Reilly: (Laughing) Yeah, touch me, yeah.

Jesse Brown: Terry, this has been a lot of fun. Thank you.

Terry O’Reilly: Thanks, Jesse. That was terrific. I enjoyed i.

(Canadaland theme music starts)

Jesse Brown: That’s your Canadaland. You can email me at I read them all. We’re on Twitter at Canadaland. Our website is Our audio editor and technical producer is Tristan Capacchione. This show’s senior producer is Bruce Thorson. Welcome, Bruce. Our managing editor is Annette Ejiofor. Special thanks this week to my colleagues Dori Smith and Jessica Valentin. I’m your host, Jesse Brown. Our theme music is by so-called syndication is handled by CFUV 101.9 FM in Victoria. You can visit them online at Thank you for supporting Canadaland.

(Canadaland theme concludes)

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