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24 Sept 2025 Cheeky Pint Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies

“There's also a thing for startups where they probably shouldn't look at what established companies are doing because—like, Stripe for so long, we clung to making sure that we had code in the homepage and people are like, if you want to accept credit card payments for your website, we are the place to come.”

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recommendation
Recorded
24 Sept 2025
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Cheeky Pint

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…comes to product marketing? Actually, do you want another pint? Yeah, sure, sure, sure. See again this one, did I not let it settle for long enough? And then you have the small head? Is this settling? I think the thing that still kills me, and it's still very common, is marketers that love marketing. So rather than actually saying anything useful or specific, you'll get, like, “Forget everything about email.” You're like, okay, what am I buying? Or, like, “transformation reinvented.” And you're like, “Cool, sounds like I'm going to reinvent some transformers.” But what's actually happening here? I think there is a general still type of thing where my screensaver on my laptop is literally a typewriter where someone said, what are you actually trying to say? And I keep that there as a reminder of just nine times out of 10, the best marketing comes from just writing the thing you want to say. Because I do know how docs—do you ever get into a Google document? “Our goal is that by reading this document, the reader will know the following.” And I'm like, cool, can we just say that and say that? Why are there 2000 more words here? So I think, I guess speaking in a way that sounds great to marketers is probably the thing that kills me most because they don't market, especially in the AI era, they don't really necessarily understand the depth of what's actually happening with the AI or whatever. There's a funny stat that Ogilvy used to quote, which would say something like, of all the winners of the Cannes awards every year something like two thirds of them would lose their contract that year because the thing they won the award for, it was not actually effective in market at all. And I think there's such a repetitive pattern there where a lot of people will look at say a Stripe or a Linear and they'll be like, “All right, we should just do that.” And I think the thing that people don't get is everything means something. And this is where Eoghan, our CEO, is so differentiate. It's just like every single decision we pick here—what photo, what icon, what typeface, whatever—it all sends a message. Are we conventional or not? Are we futuristic or not? And I think whenever I see folks just copy paste somebody else's branding—and even in the sort of, oh, we will change our homework along the way—I think what they're really doing is saying, “We don't really understand what we're doing here.” That's why a classic of this is whenever an incubator spits a new batch of startups and they all basically have right-hand side screenshot, left-hand side, three bullets, sign up button, whatever—you're kind of like, okay, cool, but have you actually thought about what you're trying to say to the world? ly have right-hand side screenshot, left-hand side, three bullets, sign up button, whatever—you're kind of like, okay, cool, but have you actually thought about what you're trying to say to the world? There's also a thing for startups where they probably shouldn't look at what established companies are doing because—like, Stripe for so long, we clung to making sure that we had code in the homepage and people are like, if you want to accept credit card payments for your website, we are the place to come. And at a certain point, most of the relevant people who come to your page actually know that you could do that, you can experiment a little bit more. And you know, Salesforce doesn't have to hit CRM so hard on the homepage. After 20 years, they've earned the right to talk about Einstein a bit. Oftentimes a startup has a great idea for a great product and they pitch it, and then six months later they work on some new feature and in their heads, the new feature is the big thing that they're so impressed with, not realizing that 99.9999 of the world have not even heard about the original thing yet. But there they go destroying their original pitch by being like, “And now we've got blah, blah.” I'm like, dude, no one's even heard of the original thing yet. And here you're pitching some nuanced take on some extra feature. Speaking of David Ogilvy, you've read On Advertising, I assume. It was just, like, that's such a beautiful book where all the marketing copy in it is so good. The Rolls-Royce side of,” The only sound you'll hear at 60 miles an hour is the ticking of the clock.” But somehow that should be mandatory reading for all product marketers. Absolutely. What kind of person succeeds in product at Intercom? When we set up Intercom originally we were building one thing. Once we forked out to building many different areas—like sales, marketing, and support—I think we gave a lot of freedom to product leaders and sort of said, “Hey, you owned a sales product, you're marketing product.” And I think the folks who succeed there are like, they have to have decent taste, and I don't mean that in some lofty abstract way, but I mean they have to use good software, identify good software, ultimately know how to pick one out of the bunch in a sense, right? A very common interview question I ask people is what apps are on your phone? What's your favorite app? And you might have thought someone's like, “Oh, I never really thought about that.” And I'm like, oh, so what's your favorite song? I am sure you care about some things. Certainly if you're interviewing musicians, they should have a favorite song. I never really thought about that.” And I'm like, oh, so what's your favorite song? I am sure you care about some things. Certainly if you're interviewing musicians, they should have a favorite song. Yeah, you'd like to think that, but they also would be a favorite app too. So I think taste is a kind of prerequisite. And then I just think the confidence to pick a direction and then we say at Intercom, we often to say shipping is an act of confidence and humility. What that means is you have to be confident enough to put it alive and then humble enough to take the slap in the face when you've got it wrong. Totally. And react to that slap. Don't be like, “No, it's not me, it's the customers don't get it.” So I think we need high taste and then confidence and then ultimately understanding that in the market and recent sense, a product is a conversation with the market. Your launch is your opening bit, and then you have to basically adapt and react to what gets thrown back at you, which might drag you in different directions. And then you need to have, again, the confidence to prune certain things. And no, we're not building an attribution engine. Yes, we'll take on some feedback in the CRM side. But I think a lot of product managers who don't work out for us are a lot more spreadsheety and they won't take a bet. They won't take a gamble, they won't take a stand. They'll just be forever mired in like, “Well, the data suggests,” and they're just trying to hedge their bet, whereas it's just not the sort of company we are. I think we kind of believe in having an opinion about a space. Well, and the second part of what you're saying, if I'm hearing you right, is that good product managers actually can listen to the market. They have to be able to, yeah, And hear what—I think about this a lot in the context of tech companies where—Stripe’s first operating principle is users first. We think that actually paying attention to what users tell us—tell us in every sense, via revealed preferences in the data, via just, like, when we actually have conversations with them. We start every week with a Monday morning meeting. The first thing we do is—we actually host in Intercom—we host a customer to tell us and give us a report card. And it's not an A, it's seldom an A. They always have things they want to fix, and they're very pragmatic things that they want us to improve. There's no overcomplicating. And then when we do our weekly all hands fireside, we also bring customers to that. But I feel like there's a problem of over-complexifying things and under-talking to users in Silicon Valley where, yeah, it's a bit too much celebration of the individual kind of product vision or a bit too much, as you say, trying to data your way out of it. And if you're a product manager and you're not talking to many customers each week, something's probably wrong. I bring that up because the whole original Intercom product was a way to talk to customers. This is kind of your guys’—but would you agree that diagnosis, that a lot of tech products would be better if people simply talk to customers more?…

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