Ian Landsman Founder of HelpSpot, a bootstrapped help desk software company he has run since 2005 with no outside funding.

“Nothing better than scrapping work. The AIs love scrapping. … How many times did that prevent me from scrapping stuff? It's like, well, I spent a month on this and like, I guess I'll just ship it because I spent a month on it. And now it's like, oh, I don't even know what happened. The AI did it. Yeah, who cares? I just trashed it.”

Mostly Technical · Laravel Ecosystem · October 2026

During the HelpSpot rebuild, Landsman converted the product's "knowledge book" feature, then scrapped it for a plain knowledge base the AI can search. With an agent doing the work, the sunk cost that used to make him ship things anyway is gone.

Mostly Technical · 2026-10-13 Listen to the episode → More from Ian Landsman → More Laravel Ecosystem quotes →

Transcript

Mostly Technical Around 58:17 into the episode

Ian Landsman

…it more heavily about like where, where does this go in this book? And like, I might have a book with a thousand pages. That's weird. Like, so it just kind of breaks down. So the books got scrapped and the books are being converted to a knowledge base, a more traditional pile of shit. Pile of crap.

Aaron Francis

Pile of crap. Put

Ian Landsman

…rebuilt. So yeah, so there's a lot of other. And I actually converted the knowledge books first. So that just got done as a conversion. But then I, because I wanted that there just in case, even though I knew I'd probably do knowledge base. Anyway, decided to do knowledge base, scrapped all that knowledge book stuff. Nothing better than scrapping work. The AI is love scrapping. Love scrapping. How many times did that prevent me from scrapping stuff? It's like, well, I spent a month on this and like, I guess I'll just ship it because I spent a month on it. And now it's like, oh, I don't even know what happened. The AI did it. Yeah, who cares? I just trashed it. I

Aaron Francis

just orbed it six hours ago. Who cares?

Ian Landsman

Exactly. It doesn't matter. So trashed all that. Have the base version, blah, blah. And all that. It's like, so it's all new UI. So again, like the AI sort of helps you, but still not, there's just a lot of stuff to do to make it work well, in my opinion. So doing all that stuff. Lots of…

Aaron Francis

When are we going to merge?

Speaker names from our own diarization · position estimated from where the line sits in the episode

More from Mostly Technical

“What I want is I don't want you to build AI into your app, I want you to make AI usable from outside your app. I want you to give me the best CLI, API, MCP in the world, and give me access to my data, and I'll take care of the rest. That's what I want as a very stupid developer.” — Aaron Francis, Mostly Technical

“You person listening should not be trying to sell developers. And they're only getting worse. They used to be terrible. … Because they would always, even in the day, be like, well, I could build this help desk. I only need like four months. … Now they're like, I could do this in an afternoon. And they really can. So you don't want them.” — Ian Landsman, Mostly Technical