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

“I think when your AI is not tied to business impact or is debatable in quality or whatever, I think you end up with these people who are just like, oh, let's just stick a tenner on the seat and see what happens.”

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evaluation
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24 Sept 2025
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Cheeky Pint

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…ally pretty simple in the greater scheme of things. And all the stuff that we needed, you guys were ahead of us on discounts for volume, et cetera, all the sort of obvious stuff people would push for. Yeah. Is this just where pricing in this new world goes? Because obviously no one buys labor on an unlimited basis, and at least for the moment, the inputs of AI do actually scale with usage for a significant basis. And so it feels like you have to have some usage-based pricing. This is certainly the bet we are making where again, the reason that billing, the top thing they're thinking about is making billing work well in the usage-based world is it just feels like many products are becoming much more expensive to serve and therefore have to have a usage-based component. But is this permanent or I dunno, does the AI get cheap enough that maybe we go back to unlimited plans or I dunno, I dunno if unlimited plans will ever, well, I dunno. Here's how I think about it. I think ultimately all AI has two vectors, there’s how much work you are doing and how well are you doing it? Yes. And the volume of work you're doing, it's almost, well actually both of 'em are going to be proportional to how many tokens you're burning or whatever. So you're going to want to factor that in, especially if you're a consumer app as well, we're going to go nuts. So I think you have to have some, I'm not a fan of cost plus pricing, but it does place a kind of lower bound on what you can do here, which is just like, hey, unlike SaaS, you are actually sending money out the back door as well. So I think you have to have something that's proportionate to how much work you're doing. And then I think aside from that, you have to charge consistent with how much work are you displacing. I think that's where you can say, hey, for us anyway, if you take an average person who sits in a seat to do customer service, if they do, let's just say they do 20 conversations a day, that's what 400 conversations a month, when we were thinking about how we charge, we're like, hey, well if that person does 400 a month, Fin does 65% of that seat, we're still up. We're only charging, whatever, $90 for the seat. So from our point of view, it was an obvious, an easy swap. I think for a lot of businesses it might not be if your AI doesn't work or it's spurious or its value can't be articulated. Isn't it cool that you can now dynamically summarize a GitHub issue or something like that? You're like, cool, I don't know how much people will pay for that. They don't know either. Or, hey, you can now generate random graphics in your newsletter tool. You're like, okay… It's like vitamins versus painkillers, AI pricing. how much people will pay for that. They don't know either. Or, hey, you can now generate random graphics in your newsletter tool. You're like, okay… It's like vitamins versus painkillers, AI pricing. And it's specifically in this case, the painkillers are very strict, if we don't do it, a human's going to do it and we know exactly what they cost, and the vitamins don't have anything approximating that. So not only is it nice to have, it's like I don't even know what it's worth. I saw a while ago someone said when Studio Ghibli came out and everyone was using that, someone said, hey, the fiverr.com equivalent of all these things would've been trillions of dollars. You're like, right, but no one was ever going to spend that. So there's no sane way to actually talk about what actually happens here. I think it was Byrne Hobart who said that when you're tied to business outcome, that business outcome is usually done by humans. I think it's going to be really, really easy to make a business case for saying swap this over to AI. It's better, faster, cheaper. I think when your AI is not tied to business impact or is debatable in quality or whatever, I think you end up with these people who are just like, oh, let's just stick a tenner on the seat and see what happens. So it's like you can have a normal seat or an AI seat and then you're kind of like, I hope no one uses the AI too much. You're permitting yourself to build weak AI stuff if you do that because you're not pushing yourselves to say, hey, we need to articulate the value of each incremental usage here. Well, when you talk about this AI pricing dynamic, one thing that really strikes me is just how fast AI companies grow from a revenue perspective. So I just saw Mati from ElevenLabs. We actually had a great session at our customer event in London, but he tweeted that they've just passed 200 million in ARR and that's 2 years after founding it, maybe 3 years after founding. But in my day, businesses didn't do that. And it's really striking for me how somehow they seem to climb the revenue ramps much quicker. I know, I mean… You guys would Fin is another example… Yeah, for sure. We forecast like Fin will be 100 million probably early next year or whatever and back at… Yeah, from when? Starting from… I dunno, probably about two years, something like that. Yeah. So two years to 100million in ARR… When we started and probably when you guys started it was like that was the threshold to go public. Exactly. It used to take a long time to get to 100 million in ARR. It was like seven years. That's the simplest AI investing framework I've heard. I'll tell you why it's simple because you're going to make me write no checks. So I guess I'd say most of the AI companies I’ve invested in probably three or four. Three of the four I'd say. ve heard. I'll tell you why it's simple because you're going to make me write no checks. So I guess I'd say most of the AI companies I’ve invested in probably three or four. Three of the four I'd say. The only one I might quibble with there, I think, that's very good for staying out of trouble. And this is where I tend to push back when people are saying, oh, it's an AI bubble. It's like, I dunno, I think people are happy with the tokens they're buying. I think a lot of tokens are happening and just generally they seem to be delivering useful outcomes… because they're actually delivering value on the customer service side or people enjoy their Midjourney adventure, but people are getting value from the products. So it's a pushback that doesn't… I was going to push back on number four, which is positive unit margins because just aren't the underlying costs… Again, when you guys started Fin, it sounds like you were underwater… Yeah, we were losing money on it… But then just pretty quickly it right-sizes as you optimize it, and so couldn't one be too focused on the current implementation? Yeah, I mean this is a conversation we have internally with our CFO quite a bit actually because, we’re good, I can imagine it’d be the kind of thing a CFO would want to… Hey, Des, do you have five minutes? That's exactly, yeah, “quick chat.” I can't help but notice the team have done this preemptive loading or whatever. It's causing this shitload of money. So what's my counter? I guess I prefer it if the path towards profitability isn't just OpenAI is going to figure this out for me, right. An interesting way I'd say this, with Fin for example, obviously our profit goes up when we are firing less dead tokens. A dead token being we've generated an answer and it wasn't right, so we can't charge money for it. If you're, say, guessing the next line of code or tab to autocomplete the next line of code, if five of six of those is wrong, I don't know if you're ever going to get bailed out because you’re basing five-sixths of your costs is not something you can resell. So there's a questionnaire of how much of your tokens are actually generating a thing that a user wants independent of what you charge for as long as the user wants it. I think you're always in good condition, whereas if you're burning a million tokens to find one, and that one, you're never going to be able to recoup your costs or at least I'd love to see your telemetry to make sure that you actually have thought this true. I suspect you haven't. 45, that’s not bad. Yeah, I was very impressed by the multiple, clearly deliberate twenties. I mean we're definitely all different. A lot of key things we all agree on, Eoghan would be like a, first and foremost, he's a very strong CEO. He is very decisive and he is very brave, is the best way I could describe it. An interesting thing, when he returned to Intercom, one of the things he did was basically rebuild the culture, and one of the things he focused on was resilience and open-mindedness. People might be offended.…

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