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

“So many bootstrapper-type companies are scared to raise their prices on their existing customers, but you have to do that. It's just free money. And okay, if you raise your price 20% and 3% of your customers go out and vibe code their own replacement, you are still up a shit ton of money.”

Mostly Technical · Laravel Ecosystem · September 2026

“So many bootstrapper-type companies are scared to raise their prices on their existing customers, but you have to do that. It's just free money. And okay, if you raise your price 20% and 3% of your customers go out and vibe code their own replacement, you are still up a shit ton of money.” — Ian Landsman, Mostly Technical

Landsman was answering a tweet arguing this is the worst time to raise software prices. His case: inflation and big vendors like QuickBooks, Salesforce and Microsoft raising prices give cover, and the vibe-coding threat is small next to the extra revenue.

Transcript

Mostly Technical Around 1:09:41 into the episode
Ian Landsman

Oh, we're going to talk about this a little bit. This is Ian

Aaron Francis

…Jesse had a tweet about, you know, this is basically the worst time to raise your prices. You should be lowering them. Ian comes in over the top with a quote tweet, slam dunk, and says, 100% wrong. No freaking way. Raise your prices. Laura Roeder weighs in. All right. What's the story here?

Ian Landsman

I didn't technically say 100% wrong, but I do think that it is a good time to raise prices because you have a lot of cover from inflation. Everybody's raising their prices. QuickBooks has raised their prices twice this year. Salesforce just raised their prices. Microsoft just raised their price. Like lots of companies and software companies are raising their price. Mintlify apparently just raised their prices, right? Like, and we've talked about this on the show before. It's just a math problem. And so many, like so many sort of bootstrapper-type companies are scared to raise their prices on their existing customers, but you have to do that. It's like just free money. And okay, if you raise your price 20% and 3% of your customers go out and vibe code their own replacement, you are still up a shit ton of money. So that's fine. It's fine if that happens. So, and if you raise your price 20% and you lose 50% of your customers, I think there's something else going on there because very few industries are the customers that price sensitive. Obviously, exceptions, developers are…

Aaron Francis

It's a good name. But

Ian Landsman

anyway, yeah. So I don't know. I just think that there's a lot of cover for that. First of all, second of all, if you're integrating AI and you're bringing efficiencies, this is why software charges more. It's literally the reason, right? It's like, hey, if you implement our software, you are going…

Aaron Francis

I think we found, I think we've found the root of all issues.

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

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