Rob Walling

I said it's like if you're built completely under WordPress and completely in it, it depends on is your switching cost low, medium, or high to rebuild it somewhere else. Like that could move that one up or down by one, but it's not going to move it to three slots, right? It's not going to suddenly become as bad as having a Shopify app where they are just known to be really aggressive with it.

So that's what I mean when I say, I think the factors are in line and I think the list is pretty tight. And again, directional correctness, such that next time someone on ex-Twitter says, everyone has platform risk, you can chime in with, well, there's different levels of it. And here are eight of them in this podcast episode. They'll obviously be listed out in the show notes.

So that's what I mean when I say, I think the factors are in line and I think the list is pretty tight. And again, directional correctness, such that next time someone on ex-Twitter says, everyone has platform risk, you can chime in with, well, there's different levels of it. And here are eight of them in this podcast episode. They'll obviously be listed out in the show notes.

And I'm certainly going to be referring back to this in the future, probably included in a book or course at some point, because I do think it's helpful for us all to have a paradigm and a framework around it. So thanks so much for listening this week and every week. It's great to have you here. This is Rob Walling signing off from episode 735.

And I'm certainly going to be referring back to this in the future, probably included in a book or course at some point, because I do think it's helpful for us all to have a paradigm and a framework around it. So thanks so much for listening this week and every week. It's great to have you here. This is Rob Walling signing off from episode 735.

Welcome to this episode of Startups for the Rest of Us. I'm Rob Walling, and this week I talk with Ian Landsman, the founder of HelpSpot. Ian has been bootstrapping for almost 20 years, and he started with on-prem software, and then after about 10 years, launched a SaaS version.

Welcome to this episode of Startups for the Rest of Us. I'm Rob Walling, and this week I talk with Ian Landsman, the founder of HelpSpot. Ian has been bootstrapping for almost 20 years, and he started with on-prem software, and then after about 10 years, launched a SaaS version.

Ian and I have known each other almost that same 20 years from back in the days of Joel on Software's Business of Software forums. And over the years, Ian has started a few of his own podcasts as well as spoken at MicroConf. I believe, I would guess it was probably around 2014 or 15. So it's a great conversation because Ian and I have history.

Ian and I have known each other almost that same 20 years from back in the days of Joel on Software's Business of Software forums. And over the years, Ian has started a few of his own podcasts as well as spoken at MicroConf. I believe, I would guess it was probably around 2014 or 15. So it's a great conversation because Ian and I have history.

I think we were able to pull out some really interesting bits about why he's bootstrapped for 20 years, why he hasn't sold and moved on to his next act, how he thinks AI is going to impact the customer service and support space. And if you stick around to the end, you'll get to hear the company name that is most often confused with HelpSpot, and it wasn't the one that I thought.

I think we were able to pull out some really interesting bits about why he's bootstrapped for 20 years, why he hasn't sold and moved on to his next act, how he thinks AI is going to impact the customer service and support space. And if you stick around to the end, you'll get to hear the company name that is most often confused with HelpSpot, and it wasn't the one that I thought.

So with that, let's dive into our conversation. Ian Lansman, welcome to the show. Thanks for having me on. It's great to be here. Cannot believe you have not been on this show.

So with that, let's dive into our conversation. Ian Lansman, welcome to the show. Thanks for having me on. It's great to be here. Cannot believe you have not been on this show.

I, uh, I'm, I'm glad you reached out. I think someone, your podcast co-host maybe mentioned it on a podcast and I use Arvid calls pod scan. And so my name popped up and I went and I'm like, wait, what? Someone wants to go outside. So I was like, yeah, dude. And I thought the same thing.

I, uh, I'm, I'm glad you reached out. I think someone, your podcast co-host maybe mentioned it on a podcast and I use Arvid calls pod scan. And so my name popped up and I went and I'm like, wait, what? Someone wants to go outside. So I was like, yeah, dude. And I thought the same thing.

I was like, I think Ian's been on it, but to give people context, like 20 year bootstrapper, I mean, really early, man. Back in the day. Remember how it was? There's going to be a lot of jokes about how back in the day there was no customer development. There was no AWS. There was no SaaS, right?

I was like, I think Ian's been on it, but to give people context, like 20 year bootstrapper, I mean, really early, man. Back in the day. Remember how it was? There's going to be a lot of jokes about how back in the day there was no customer development. There was no AWS. There was no SaaS, right?

It's hard to believe we've become the old timers. How did that happen? Oh, yeah. Big time. Just so people know, you're the founder of HelpSpot. It's at helpspot.com. Your H1 is your customer service at scale. Amplify your support with HelpSpot, the streamlined solution for scaling customer service effectively. So it's email ticketing, reporting and metrics, knowledge base, self-service.

It's hard to believe we've become the old timers. How did that happen? Oh, yeah. Big time. Just so people know, you're the founder of HelpSpot. It's at helpspot.com. Your H1 is your customer service at scale. Amplify your support with HelpSpot, the streamlined solution for scaling customer service effectively. So it's email ticketing, reporting and metrics, knowledge base, self-service.

And since you started so long ago, you were on-prem for years and then you launched a SaaS. So you have both on-prem and SaaS. And I think most folks listening know what on-prem is, but it's where they actually download your code, your source code, PHP Laravel, and they will install it on their own server. And then they, I guess, what's the benefit?