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Ian Landsman

👤 Person
190 total appearances

Appearances Over Time

Podcast Appearances

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

There's definitely been some companies that made big moves, like Klarna got a lot of press for moving almost all their support to AI. But again, that is a very particular use case where they don't have a lot of different types of questions. Basically, it's like, I want a refund. Like, how do I pay my bill? So I think a very good use case for like an AI. They had poor service ratings to begin with.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

There's definitely been some companies that made big moves, like Klarna got a lot of press for moving almost all their support to AI. But again, that is a very particular use case where they don't have a lot of different types of questions. Basically, it's like, I want a refund. Like, how do I pay my bill? So I think a very good use case for like an AI. They had poor service ratings to begin with.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

So it's like, are the AI people going to do any worse? Probably not. So, you know, you have some differences there. But yeah, who knows? So, I mean, on the one hand, it's like there are those fears of just might consolidate down to a few big AI players who do a fantastic job with it and they just gobble everything up.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

So it's like, are the AI people going to do any worse? Probably not. So, you know, you have some differences there. But yeah, who knows? So, I mean, on the one hand, it's like there are those fears of just might consolidate down to a few big AI players who do a fantastic job with it and they just gobble everything up.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Or is there going to be – is it not going to be a thing at all or more of a middle ground where since we have access to a lot of similar technology at least ostensibly, right? We can pay for open AI or whatever else. We can add those tools to – for the most part, I think there's going to be probably some things that are going to be beyond our capability. But –

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Or is there going to be – is it not going to be a thing at all or more of a middle ground where since we have access to a lot of similar technology at least ostensibly, right? We can pay for open AI or whatever else. We can add those tools to – for the most part, I think there's going to be probably some things that are going to be beyond our capability. But –

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, so I think that's definitely just a big unknown. And we haven't had that in a long time. And so to help that space, it's been pretty stable. So this is definitely a new thing that's out there. And it's like, you know, we'll see how it goes. Is it we're definitely adding AI features. And maybe that's just kind of be kind of where it ends up. But we'll see.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, so I think that's definitely just a big unknown. And we haven't had that in a long time. And so to help that space, it's been pretty stable. So this is definitely a new thing that's out there. And it's like, you know, we'll see how it goes. Is it we're definitely adding AI features. And maybe that's just kind of be kind of where it ends up. But we'll see.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, so very early on, we did kind of like your standard writing helpers. We went farther than most of the other help desk tools I've seen have gone where you can define your own prompts and tools for the agents. But still, it's ultimately more like on the writing and human creation side.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, so very early on, we did kind of like your standard writing helpers. We went farther than most of the other help desk tools I've seen have gone where you can define your own prompts and tools for the agents. But still, it's ultimately more like on the writing and human creation side.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

But from there, you know, we're working on doing things like auto triaging, where it can route inbound tickets to the right categories or right agents and things like that. So that's going to be one of the first more sort of offensive-minded, more active AI elements that we're going to be adding.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

But from there, you know, we're working on doing things like auto triaging, where it can route inbound tickets to the right categories or right agents and things like that. So that's going to be one of the first more sort of offensive-minded, more active AI elements that we're going to be adding.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

And then from there, we have some different ideas about how we might do auto-responding in a way that's maybe a little bit safer. So obviously everybody's trying to go for like the holy grail of like The AI just responds, like you give it anything and it can just respond, right?

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

And then from there, we have some different ideas about how we might do auto-responding in a way that's maybe a little bit safer. So obviously everybody's trying to go for like the holy grail of like The AI just responds, like you give it anything and it can just respond, right?

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

But, you know, maybe there's some in-between ground there where it's more of a human response, but we use the AI to maybe figure out what's the right response or some different things like that. So some stuff in R&D, some stuff very close to shipping. Yeah, so that's kind of where we're at with it.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

But, you know, maybe there's some in-between ground there where it's more of a human response, but we use the AI to maybe figure out what's the right response or some different things like that. So some stuff in R&D, some stuff very close to shipping. Yeah, so that's kind of where we're at with it.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

But there's a big sort of sea change, much like when I started the company, which is like everybody's using client server apps or just pure email. And that was like the big shift. And now it seems like there might be another big shift. I don't know if it'll be quite. It could be bigger than that. It could be less than that. I don't know. Who knows? But we'll see.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

But there's a big sort of sea change, much like when I started the company, which is like everybody's using client server apps or just pure email. And that was like the big shift. And now it seems like there might be another big shift. I don't know if it'll be quite. It could be bigger than that. It could be less than that. I don't know. Who knows? But we'll see.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, so those don't bother me at all. There's lots of help, you know. whatever, variations. But I thought the spot was kind of my unique thing. I like the spot. And Dharmesh Shah, who's the co-founder of HubSpot, was in Joel on software with us and kind of in our circles, right? And then he starts HubSpot and stole my spot. And so now it's HubSpot.

Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)

Yeah, so those don't bother me at all. There's lots of help, you know. whatever, variations. But I thought the spot was kind of my unique thing. I like the spot. And Dharmesh Shah, who's the co-founder of HubSpot, was in Joel on software with us and kind of in our circles, right? And then he starts HubSpot and stole my spot. And so now it's HubSpot.