Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
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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. 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.
You're like OG bootstrapper. Somebody on Twitter reached out and said I should come on here. And I was like, man, I think I've been on there. And then I surged and I was like, man, I haven't been on there. Wow, that's crazy. Yeah.
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?
We're before all that, man.
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?
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, so definitely the majority are using the SaaS version these days, but we still have new customers in the on-prem. And basically there's some advantages. Like big companies or certain specialized companies like in finance, healthcare, they have different rules potentially, laws. They're also the type of companies that still have IT departments. And so they want to be in control of their own data is usually the main reason in terms of they control the database and they're backing it up and those things. But also sometimes they're just running completely off the internet. It's like, here's our help desk. It's for maybe IT in that case. And it's literally not connected to the internet. And so it's just fully encapsulated in their network behind their firewall. And so they want to do that. And that's, it is an area I think people have like abandoned completely because that maybe is like shouldn't be totally abandoned because there are some, you know, you could charge more.
We actually charge the same price currently, but I think there's a lot of opportunities there to charge a lot more for the people who want it on-premise and things like that. So yeah, it's not that bad. If you have a modern SaaS app, it's not impossible to make an on-premise version. Like some things, like if you depend on 30 services, that's going to be hard.
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