Rob Walling

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?

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?

Like why would today, I would just do the SaaS personally, but like the people who still use on-prem today, what is, why do they do that rather than pay you for the SaaS?

Like why would today, I would just do the SaaS personally, but like the people who still use on-prem today, what is, why do they do that rather than pay you for the SaaS?

Yeah, we have a few tiny seed companies and I don't know how many exactly, but when they apply, they'll often say, so we're SaaS, but we also do on-prem. Is that going to be a deal breaker? I was like, no, we funded a handful.

Yeah, we have a few tiny seed companies and I don't know how many exactly, but when they apply, they'll often say, so we're SaaS, but we also do on-prem. Is that going to be a deal breaker? I was like, no, we funded a handful.

And again, I don't know if it's five or if it's 10 out of 170, but there are, especially like you said, in finance or in certain regulated industries where you really do need or want control of that data and just want on some random spot. Yeah.

And again, I don't know if it's five or if it's 10 out of 170, but there are, especially like you said, in finance or in certain regulated industries where you really do need or want control of that data and just want on some random spot. Yeah.

And I want to be clear. I want to get back to on-prem, you know, probably halfway through the interview. What we're not saying is once, once.com, right? It's not you pay once and you run it. That's a whole different thing. I guess it's related. But to circle back to where I wanted to start is where is the business at today? Yeah.

And I want to be clear. I want to get back to on-prem, you know, probably halfway through the interview. What we're not saying is once, once.com, right? It's not you pay once and you run it. That's a whole different thing. I guess it's related. But to circle back to where I wanted to start is where is the business at today? Yeah.