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

“Everyone's happy with v2, now I think we can try to do something new for customers, like expand our share of wallet or whatever. But I think a lot of people try to solve revenue growth with, like, aimless product expansion to just try and increase the share of wallet for the people who are stuck with you, and then they convince themselves they got PMF or that they have some sort of a good product because they're kind of like foie-gras style force feeding new features down to throats of their trapped users, and they're like, “We're doing great.”

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evaluation
Recorded
24 Sept 2025
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Cheeky Pint

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…the product, the people who are managing fraud within the business or actually responsible for increasing conversion or something like that. Yeah, yeah. So, that was why we chose that. Word. Yeah, no… Yes, it is funny you say that. It feels like many tech companies over-rotate on sales feedback, which will by definition be from the marginal user and they're marginal in two senses. So you have all your existing users that—you're dancing with the girl that brung you over here—and then you have this future potential user who—firstly by virtue of the fact they're not already using you, maybe they're slightly outside your wheelhouse or the use case isn't perfect or something like that. So maybe they're not quite as good a fit as your existing customers. And then also by virtue of the fact that they have a whole existing way of doing things when they migrate over to your product, they'll do so in a bit worse shape of integration, where maybe they'll only use one of the four features, or not everyone in the org will be bought in. Versus the people who grew up on your product. And so maybe just restating what you're saying, I'm always struck by people are way too focused on, “We tried to win this big new shiny enterprise account and we didn't have feature X, and so therefore we're going to develop feature X,” as opposed to you've all these users who grew up in your products and really like it, but they wish you had fixed A, B, and C. And just the nature of the fact that sales gets more airtime than account management, essentially, means people really misprioritized where they spend that. t, but they wish you had fixed A, B, and C. And just the nature of the fact that sales gets more airtime than account management, essentially, means people really misprioritized where they spend that. And people take NRR for granted and think that net new revenue is hard. And I think one of the things that we see a lot of is in terms of working out for your current customers, we use the phrase “permission to innovate” and “permission to expand” in Intercom, which is basically you have permission to innovate when your product's pretty good. Like, let's work on v3, but is v2 in good condition? And then permission to expand is like v3 isn't actually that exciting. Everyone's happy with v2, now I think we can try to do something new for customers, like expand our share of wallet or whatever. But I think a lot of people try to solve revenue growth with, like, aimless product expansion to just try and increase the share of wallet for the people who are stuck with you, and then they convince themselves they got PMF or that they have some sort of a good product because they're kind of like foie-gras style force feeding new features down to throats of their trapped users, and they're like, “We're doing great. ” But they don't realize what they're actually doing is making their current product so messy that they're destroying the hope of future revenue. You can force your current customers into whatever upsells you have or whatever, but your product marketing along the way is getting really difficult because all these features don't make sense. And they're just like, you've tried to do this land and expanding, but you're actually just expanding and there’s no landing happening in the new product. And then you end up trying to twist yourselves in knots. And a lot of startups, Jason Lemkin said this thing: from zero to one is impossible, from one to 10 is hard, and from 10 to a hundred is inevitable. I think a lot of people, I don't think that's proven out to be true as much as it was back when he said it. I think a lot of people get stuck in some sort of glue around—somewhere around a 10 million mark—where they don't know how to get the next 10,000 logos. So they just try and milk the revenue out of the existing customers. True, just forced product adoption of new stuff. You see a lot, “Here's your copilot, I know you didn't want it, but here you go.” That type of thing. d milk the revenue out of the existing customers. True, just forced product adoption of new stuff. You see a lot, “Here's your copilot, I know you didn't want it, but here you go.” That type of thing. Des is describing here how they've transformed Intercom from a SaaS product to a frontier AI business. And to do so, they had to pivot not just the product but the monetization model as well. Because inference costs are so significant, AI-powered companies tend to charge based on usage rather than just allowing for unlimited plans. It gets complicated and really multidimensional very quickly. Now, fortunately, complicated and multidimensional is what Stripe Billing specializes in. Our usage-based billing engine can ingest up to a hundred thousand events a second—a hundred thousand events a second! So AI companies can monetize products based on real-time customer usage. We're powering consumption billing for companies like Figma, Cognition and tons of other leading AI applications. Our usage-based billing platform has grown 145% so far this year. So whether you're changing your business model like Intercom or starting a new product from scratch, your business strategy should dictate the billing system and not the other way around. For usage-based billing, check out Stripe Billing. I mean, the biggest problem, mistake is not aligning your fundraising with your TAM. I think a lot of folks, we got a little bit over-convinced during the era of cloud that every business had a right to be like a unicorn. And so there's a lot of businesses whose idea was totally fine, but actually they should have gone and basecamped it more so than they did because they've raised on the assumption there's an easy path to hundreds of millions in revenue. It should be more small, profitable, $30 billion revenue companies. Well, yeah, exactly. And I think a lot of these businesses would be great if only they didn't raise 20 and tell their investors that “you're going to easily be worth a billion” or whatever. So I think there's a genuine mismatch there where I think people have overstated how big this idea could get, as in, “Hey, I know all we do is time tracking for dentists in Delaware, but believe me, we're going to be a billion dollar company.” And you're like, okay, well one of your restrictions is going to have to break here. So that's one problem, which is more like business model and venture ambition. The other stuff I see is, it is not focusing enough on the thing the majority of your customer's value. It's easy to say—the best business in the world is one line of code that all users execute and you sell it to all users, right? They're like the sweet spot. It's hard to do in a differentiated way because obviously people learn that line of code. And I also think there's a weird celebration in the valley of Act 2. The Valley is obsessed with finding second acts that are totally unrelated to the first business, the number of people who bring up, “Oh, and we invent an AWS.” It's like, okay, you need to use a noncliche example if you’re going to make that argument.…

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