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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.

“You have $30,000 of people in this meeting, right? To replace any product you're currently paying for as a SaaS, you're going to have many meetings. Even if every meeting costs you $2,000 or $3,000, you're at $10,000 of time before you've built anything, before you've decided who's responsible, who's going to build it, who's going to maintain it. You're at tens of thousands of dollars very quickly in any type of bigger-than-founder-led organization.”

Mostly Technical · Bootstrapped & Indie SaaS · November 2026

“You have $30,000 of people in this meeting, right? To replace any product you're currently paying for as a SaaS, you're going to have many meetings. Even if every meeting costs you $2,000 or $3,000, you're at $10,000 of time before you've built anything, before you've decided who's responsible, who's going to build it, who's going to maintain it. You're at tens of thousands of dollars very quickly in any type of bigger-than-founder-led organization.” — Ian Landsman, Mostly Technical

Context

Ian mentions a company that tracks the dollar cost of each meeting, and uses it to argue that replacing a $500-a-month SaaS tool with a homegrown one has to clear a high bar. It is his economic case against 'everyone will build their own CRM'.

Transcript

Mostly Technical Around 56:41 into the episode
Ian Landsman

…because I don't know if he wants us to share this. But we have a friend, and at their company, they track the cost of meetings, right? They do, and he occasionally posts a meeting he's in, the cost of it, and it'll be $30,000 is the cost of this one meeting. The people who are in this one estimated

Aaron Francis

by salary divided by time multiplied by number of people there. Yeah.

Ian Landsman

So, you have $30,000 of people in this meeting, right? So, my premise is that to replace any product that's currently you're paying for a SaaS, you're going to have many meetings. But even if it's not, let's say it's five meetings, you're going to have five meetings because you're a bigger business. And let's go not that extreme example. Let's go with a smaller example where every meeting costs you $2,000 or $3,000. Like, right there, you're at $10,000 of time. That's before you built anything, before you do anything, before you've decided the procedures, before you've decided who's responsible, who's going to build it, who's going to maintain it, all the stuff. Like, you're at tens of thousands of dollars very quickly in any type of bigger than founder-led organization. And so, I don't know. Like, I just think that those people are looking at the trade-offs very differently. And so, to me, that the main trade-off there is like, can I replace this CRM and get go from something that's somewhat generic, right? Just by its nature to like my own custom one. And the difference there is so valuable that it more has to more than make up for the time and cost and effort. So, like, if I just, if it costs me $20,000, $30,000 a year to replace…

Aaron Francis

I think you are old man.

Ian Landsman

Yeah.

Aaron Francis

Which, again, happy belated. But I think, one, I think you continue to believe that people are rational economic actors, which I don't think is true. I don't think as people are, but a company is. I don't think that is true. People are just companies are just people.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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