Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Tue, 08 Oct 2024
In episode 734, Rob Walling interviews Ian Landsman, founder of HelpSpot, about his 20-year bootstrapper journey. They discuss Ian's transition from on-prem software to SaaS, the challenges and benefits of each, and the early days of building the business. They wrap up by discussing the potential impact of AI on the customer service industry. Topics we cover: 1:11 – Ian, the OG bootstrapper 2:22 – Benefits of on-prem software in 2024 5:46 – Slow, steady, profitable growth through the years 9:20 – Embracing a risky start 14:11 – Getting early awareness 18:52 – Transitioning to SaaS 26:37 – Laravel raises $57M 28:59 – AI impact on customer service Links from the Show: The SaaS Playbook TinySeed Ian Landsman (@ianlandsman) | X HelpSpot (@helpspot) | X HelpSpot Podscan Accel invests $57M into Laravel Products & Open-Source Framework Mostly Technical If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify
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.
But with a little bit of forethought, it's really not that bad.
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.
Yeah. It also gives you some advantages of like you're a tiny bootstrap company. You're not going to be able to be SOC 2 compliant, for example. And there's going to be these type of companies that are like, well, you're SOC 2. Let me talk to your security people about all this stuff. And it's just like you, right? It's you and a couple of people.
And so this gives you some outs with those big companies. It's like, hey, you know what? You can install in your own SOC 2 data center and you're already SOC 2 and you can – it's all good. And so – We'll charge you for that and everything. And those tend to be also like some of the best customers. I mean, those are the customers that stay with you for a decade. You're in there. You're on a server.
They're just not even the type of companies that are in the mindset of like, oh, somebody launched a new fancier version of this tool we use. Let's go out and find the fancy. Let's take a look at this and let's see if we can switch over. It's like they're not the culture in these companies.
It's not like that, which is great for you as the bootstrapper who isn't always moving as fast as a VC-backed company can or some big company that enters your territory It's like you got a lot of customers that are just there and they're happy with your product and they're not looking around for other solutions.
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.
Yeah, so we're profitable, doing well, a little under 2 million ARR, five employees. I think five? Yeah, five full-time employees and a couple of part-time people. So it's kind of been running. It's just going. It goes up a few percent every year, and it's fine, and we're profitable, and it's great, and I've been running it in sort of that – Uh, not, you know, people say lifestyle.
I wouldn't know if I'd go all the way to lap, but that implies a certain ease of life that I don't know if I'm all the way achieved, but yeah, not super stressed about that stuff. It's been nice, especially the last, I think we're going to talk about the early years. There's probably more action in some ways, but it's kind of last 10 years. You know, my kids have been getting bigger.
My oldest just went to college. So it's sort of been this, like, I've been cool with it being profitable and running well. And that's great. And, uh, I think we're starting to turn a little corner of some new things I want to do with it as I get more time, kids get older, all that stuff. But yeah, it's doing well.
this is going to sound like a negative pejorative question, but it's like, how have you not gotten bored? I would, I would get bored where 19, you're going to be, it's next year, 20 years. Yeah. And you know, I know we all have different personalities and I'm, I'm the person who's never worked the same job.
Even let's see, I think microconf, well, microconf doesn't totally count, but even cause it was part-time for me, it was a hobby for many years. Right. But microconf and tiny seed now, I think are the thing I've worked on the longest six years. Cause Because even Drip, which from the founding to selling was three and a half years. And then I stayed another like two years.
So even Drip was five and a half years. You know that? So you can tell I just had that personality of like, oh, I need to do the next thing. But you've stuck with something for 20 years.
You know, I don't know. I'd never, I guess I wouldn't have thought it would be exactly like that in the beginning necessarily. I think what I've done is since it's been profitable, it's given me flexibility to do other things along the way. So like I ran Laracon conferences, both in world and online. So like similar to what, you know, you've done with MicroConf as like a way to explore things.
We built a job board for the Laravel and we run the official job board. We, I built a product called Thermostat that, didn't really work. And I recently sold off. I built another product that I sold off that didn't work.
So like every, you know, three or four years I get into something else and that'll distract me for a little while, probably to help spots detriment, but also probably practically just something that needs to happen to keep me, um, you know, when I come back to help spot, you know, after my little excursions, it's like, oh, It's still here. It's still doing great.
Like I'm re-energized to like take on some new stuff and do some new things. And so that's kind of how I've done it. Yeah.
And it's, you know, I think it's something I'm sure you hear a lot and bootstrapper sort of problems, let's say, is that you get to a certain level of success and it's just a little bit of a weird zone where like it's not big enough to sell for the amount of money that's just like, oh, I'd never have to work again money. I'm totally set. Don't worry about it.
It's not quite big enough for that really. Maybe if I sold in 2021, it's right at the top there. But so it's never been like really, I've never had any really appealing offers. That's like, oh yeah, I should sell it. Obviously you could just sell it to sell it and move on to the next thing and still have a nice amount of money.
But it's like, ah, who knows if the second product, I've never built a really good second product. I mean, some of these things have been okay, but it's hard to build a second product. So it's like, ah, I got the first product that's done so well. I'm just gonna... Stick with that.
That makes sense. Let's go back to the beginning. So you launched it in 2005 and you told me that you quit your day job and coded for six months, which is exactly what we tell people not to do today, right? Don't quit your day job and live off savings. Or, you know, you said your wife was basically supporting you during that time. But what a gamble. To me, it's like terrifying to do that, right?
Like, why did, were you scared at all? And why do you think, why do you think it actually worked? What was that time like?
Yeah, it was, oh man, it's so wild to think about now. The world was just incredibly different. Like in 2004, it kind of started, I learned, I wasn't even a programmer, like in college or anything, I learned the program on my own. And then I was like, okay, I want to do a product.
We went through a million product ideas, whatever, finally came on this HelpSpot idea because I used a really awful help desk at work that was mainframe based and didn't accept email and all this stuff. That's like where the world was back then, just to set the stage. Like a lot of big companies just used, had no help desk or a very poor help desk solution. So I was like, okay, I want to do this.
We both, me and my wife agreed. It's a good idea. So like we had just bought this condo, which was a little bit pricey. I was a little nerve wracking. We sold my car. So we had that money, put it in the bank. So we just went down to the one car. My wife kept working.
And then, yeah, it's like, I would never give anybody this advice now, but it's just such a different world because it's like, there was no choice. There was no real frameworks. There's no Ruby on Rails. There's no Laravel. There's none of these things. And so it's like, okay, I know PHP. I'm just gonna have to write it. I don't even know JavaScript.
So I'm literally sitting there with the JavaScript Bible, which is like a four inch thick book, learning JavaScript while I'm building the app.
And yeah, it's like, you know, I always say like, I could build V1 of Help Spot today, probably in three weeks or something with like, if I just use all the modern tools and everything we have and just do the very basic version that it was in version one, it's like, yeah, you could do it. keep your job, do it on the side, all that stuff. But it just would literally never happen.
I mean, I worked six days a week, like 12 hours a day for six months. And even then it wasn't great. It was just like functional, you know? And so that's just what you had to do back then or it wasn't going to happen. Like those were the, those were the options.
That's when back when people would raise half a million dollars with just an idea like that really doesn't happen anymore. But you had to do it because, as you said, you had to write every line of code and there were really no libraries. And it was so, yeah, it was a lot more to be done.
Even the raising money is something I thought about. But you got to remember, 2004, I mean, the dot-com bust was just a couple years before that. The whole VC world was kind of a mess. They weren't, like, looking to fund individual guys with an idea too much. I'm sure there was some investments, but it wasn't very common. So, yeah. So, we were all – I mean, you were there, right?
Like, we were all in these bootstrap circles, Joel on Software Forum, and all kind of just – Working together to figure out how do we ship software without really any big funding.
That was the thing is the narrative was still raise a bunch of money. But we, there were just, there was Joel Spolsky and there was, well, it was you.
Eric Sink.
Eric Sink. Patty O'Levin was there. Patty O'Levin, yeah. And these were, and we all knew each other by name. Right. It was like, oh yeah, they just, and we're all trying to figure it out kind of on our own, but also together. Right. Of like, is this even possible to do? Like there was no narrative. There were no books on this topic. There were no podcasts. You just kind of, it was forums, right?
I mean, that's what I remember.
Yeah. Just forums. That's it. There was not much else. Those of us in the community had blogs or whatever. And we talked about it. We talked about it in the forums. But yeah, no Twitter, right? No, none of the, no YouTube posts. Nothing. Like there was not a lot of nice ways to get information about how people do it and different strategies and all that stuff.
There was like, Joel was writing some books. Eric Sink wrote some awesome books. That was, that was kind of it.
Yeah. And I remember around that time, cause as I, I think I had done an invoice in 04. And I didn't know, I was like, well, how do you do, how do you market? How do you know, how do you do SEO, AdWords, you know, whatever? And so I would go look at the internet. There were no books about startups doing this. It was all the info marketer, internet marketing stuff.
And so I went and learned copywriting from them and applied it to startups. And I was like, oh, they split tests. A lot of them were very scammy info internet marketers. So I would take that and then translate it to me, which was the not scammy version. So they were doing split testing, they were doing AdWords, they were doing SEO, and I learned from those folks and translated it in.
And no one was really talking about that in the startup space. Startups were like, raise a bunch of money, go viral, and have a big launch party, buy billboards. It was this really odd thing of like, it was brand. It was a weird time. But folks like you starting HomeSpot, like you needed nuts and bolts. How do I get in front of people?
How do I sell so that I can have a paycheck, you know, next week? Let's flash forward six months, right? So you spend six months building, you get to launch day, like, how do you get the word out?
Man, it is crazy. You're going to appreciate this being an email newsletter kind of guy. So I built a list, an email list of, and this was really basically just people from the Joel Otsoffer Forum and a few people who follow my blog. And it was literally like 84 people, right? Like now people launch are like, oh man, I only have a thousand people on the list. What are we going to do? 84 people.
And the first month, we had like $4,000 in sales. And it's like some people brought it into their companies and brought it to their boss and like whatever. And I had started on the SEO a little bit before launch too with like the landing page and stuff. And, you know, like help desk software in terms of web-based help desk software was new.
So we were like first or second for like the term help desk software for like several years. Just kind of like... Blue Ocean or whatever. And that was like our main marketing channel. But yeah, the initial launch was like this 80 person email list. Then the SEO kind of picked up over those first few months. And then that was kind of it just like started going.
And, you know, we still have a lot of those customers today. But yeah, that was the that was the kickoff.
So someone listening to this who has tried to launch and failed thinks you got $4,000 of sales in your first month. Like what a month. I do want to remind them, this was not, it's not 4,000 of MRR. No. It is 4,000 effectively one time, right? Did you have a maintenance fee each year or how did that work?
Yeah, so that's a great point. Nobody out there listening is even going to think of it that way. Yeah, so it is not 4,000 MRR and you're like, woo, baby, we're like launched and going. Yeah, so it was $4,000 because it was an owned license. So you buy the license and you own it. And then...
yearly, there's a support maintenance fee where if you, you know, you pay that and you get updates and you get support. And so if you don't pay that, you don't get updates and you don't get support. And so the good thing though, is that like, it was effectively a recurring revenue and this is all annual. So yeah, it was 4,000. It was like a 30 something, 30%, let's say, um, was the support fee.
So it'd be, you know, whatever it is, like 1500 bucks or whatever. A year after that, so each year that the first group of $4,000 would pay us $1,500 to maintain support updates. It's a B2B app. It's a heavy use B2B app where it's not just like we use it once in a while. It's like, no, you're paying people full salaries to sit in this app 40 hours a week and use it.
And so generally, most companies are going to pay that support. And they did. And so that worked out good long term. But yeah, absolutely. It wasn't like, oh, man, this is monthly. Four grand a month was definitely not that. Yeah.
Do you remember what your pricing was? I'm just trying to get an idea of how many copies sold to get Fort Grin.
Oh, geez. I think it was... It was either, I think it was like 150 a license.
So it would have been like 30, not quite 30, like 26 or 27, somewhere in there, licenses.
Yeah, something like that. That's pretty good. Sounds right.
That's not bad at all.
Yeah, I was happy. I was like, whoa. And then we mined that mailing list. And so the second month was like $1,000 or something crazy. And it was a little nerve-wracking there. And then it went up after that and just like kept going up.
That's an SEO cot. Yeah, exactly. seven to 10 copies, sometimes up to like 13 copies or whatever. So you're talking like two, three, 4,000 a month. And we did have 20% maintenance, but it really was, it was one time. And so when, if we lost our SEO rankings or like during the financial crisis, we would lose like 80% of our revenue overnight.
So we'd go from like three grand down to like 500 because nothing was recurring. So, you know, you basically front load it, right? It's like they're paying for a year Which is good when you're, which is actually good when you're bootstrapping because you get a lot more cash up front.
Keeps you in business.
Yeah, it was pretty nice.
Yeah, well, I think that's true. Like with the invoicing software, it's like, it's a little more like, hey, we use it, it works. Yeah, well, maybe with some of us, sometime we'll pay him his renewal, but we don't really care that much. It's operational, right? It's like, if you can get to that next layer of like, no, we have like $2 million in payroll using this software.
And like, now we're taking this big risk. If we're down for a day, it's like, a big problem and we're losing money, right? More directly. And so I think when you're thinking about the kind of business to get into, there are advantages to that kind of thing where it's a product that people use very heavily, very competitive nowadays too.
So you had this on-prem software from 05 until you told me 2015 is when you launched a SaaS version. And The question that popped up in my mind around that is, 2015 feels late to launch SaaS. SaaS first became kind of in the zeitgeist in, I would say, like, 07 to 09. That MailChimp became a thing. Certainly there was SaaS before that, but it wasn't called that.
I remember ASPs and whatever, the other acronyms. Basecamp. Basecamp, Salesforce. Salesforce.
constant contact you know they were around even a weber was like really early but i remember by like 2011 2012 like sas was that was a thing it was like going so i would think you know you having this on-prem would have have moved to sat and not moved but just deployed a subscription version earlier so what what was the delay and i'm not acting like you you launched it late but it's just in my head yeah that number so what what what took that time
I think it was like really a couple of different things. Definitely when I launched, I knew about SaaS and made the decision to not make it SaaS because I didn't know anything about running servers. There was no money to hire somebody else to run servers. And so I just feel like that wouldn't have ultimately worked out very well.
So it was on premise and then was kind of going along and it was busy and it was fine. And the big... obviously when I took one notice in terms of direct competition was you had like Zendesk, which I think was maybe like 2008 ish something in there. And it's like, oh, okay. Like this is really becoming a thing now.
So I should probably start thinking about more, but we did even before Zendesk earlier on have a partnership with a hosting company and they ran the hosted version of help spot for people. And so it was a separate relationship with them. It's like,
You came to us, you bought the licenses, you went to them, you paid the monthly hosting fee, but they would actually install HelpSpot and run it for you. And if there was a problem with the server, they'd fix it. So we had this sort of in-between. So that did let us delay. Then another sort of aspect to it is that HelpSpot was not in any way conceived as a SaaS.
So like the data structures are not correct for SaaS and things like that. And so in that earlier phase of the SaaS rise, I think it would have been pretty tricky to do it. And what kind of happened later on is we had, then you have AWS, you have really cheap servers and things like that.
And so it made it simpler for us to make the move because how HubSpot SaaS version runs is actually everybody gets a tiny AWS like nano server and everybody's on their own server. We do have a centralized like big database, RDS database with like multi failover and all that stuff. But we basically deploy it as your own little help spot server.
And so we don't have to make the database work for multi tenant and all these things. And the cost isn't outrageous because by that point, It was like, okay, two bucks a month, you can have a little mini server on AWS. And so that's the way we rolled it out. And this way we can kind of keep the code base the same for on-premise and cloud.
You know, and as we go, I think it's going to start to, we do already make a lot more accommodations for the cloud version since it's more of the new customers. But yeah, that was kind of like the transformation there basically.
How painful was that to go on-premises? Oh, it's painful. Was it brutal?
It's brutal. Very painful. I mean, because there's a lot involved. We had to switch. We moved to subscription pricing at that time. But I didn't want to force everybody's subscription pricing. And so it's like if you want to be on the cloud version, you have to move to subscription. And yeah, so that was big.
So even on-premise customers now, if you're a new on-premise customer, you're on subscription. Everybody's on subscription. And it is annual subscription, which is another thing I think founders don't think enough about. It's just only having – I've only ever had annual. And I think it's serving pretty well. We are going to experiment with the monthly option here soonish.
But, you know, again, if you're in the kind of business where it's like – often it's like literally a committee we're dealing with. And they're evaluating multiple choices. And they're not really going to switch off like on a whim after three months. Like they're making a commitment on their end. So not that big a deal. So – That was kind of a big one, the subscriptions, the tech.
Yeah, there was, oh, the other thing is moving people. So we have all these existing customers and they want to move. And it's a big app. You can, you know, we have customers with 70 gigabyte databases. And so moving them onto the cloud is quite a production. We also allow a lot of customization. It's kind of one of HubSpot's differentiators from other solutions.
There's a lot of knobs and dials and things you can do. You can even write your own PHP in certain spots if you want to do something very custom, which is something that other helpdesk software won't let you customize on that deeper level, obviously, because there's no way for them to really safely do that. So we still to today, so we did that 10 years ago.
Today, we still will have at least usually one a month, but sometimes more of customers coming from on-premise to our cloud solution. And yeah, it's, you know, it's a multi-week operation usually to alter, not pure time, not like 80 hours, but, you know, going back and forth and figuring it all out and they check it and blah, blah. So yeah, it's a big process.
I was going to ask if you still offer on-prem or if at a certain point, obviously, you know, if you still have a bunch of customers using it, paying you, you would let them keep going. But the idea of just going to help spot.com and the only thing you can sign up for is the SAS, you know, did you ever, you haven't done that. You still offer both. What's the thinking there?
Yeah, and we have had competitors. I think Kyoko was also an on-premise like us, and then they moved to SaaS, and then they said, that's it, no more on-premise. Spiceworks also said no more on-premise. So people are definitely abandoning the on-premise. But yeah, for us, I just feel like we definitely obviously have a good amount of customers who still use it.
Like I said earlier, those are some of our biggest, best customers. Been with us 14 years and pay us $20,000 a year, right? Big accounts for us. And so- Like definitely eliminating that would be tricky if they had to, if I'm forcing them to come up to my cloud or go elsewhere, like some percentage are obviously going to go elsewhere just naturally. So I don't want to do that.
I could, of course, like you said, just going forward. But again, it's like a lot of like really great customers are in the on-premise. So even though it's only probably 10% of our new business. It's a valuable 10%. And also, I think we haven't done a great job marketing it recently. And that's something I want to actually do better and try to get that actually up a little bit.
There are interesting trade-offs with on-premise in that it's more support, for sure, because they're just like server issues. And sometimes the support person takes half a day on somebody else's problem, ultimately, that we end up being responsible for helping them. Things like that. But...
Um, you know, again, there are a lot, oftentimes much more higher revenue than the day in, day out customer. And they also, there's other little interesting things like they often pay by check or transfer, which costs either nothing or $10 versus cloud customers that often pay by. credit card and costs 5% ultimately and stuff, which went on $10,000, 5% is a lot of money.
So there are these little other things too, but yeah, that's kind of the reasons. I still think that there's something there.
And also that I think in general, we're seeing like Elastisearch and databases and a lot of the structural things still are even more so offering on-prem, you know, quote unquote, it might be literally on-prem, it might be in your AWS cloud, but it's your cloud, not our cloud. And so I think there's just still opportunity there that,
I wouldn't want to be totally out of the game, especially because no other help desk software, nobody knew when help desk software was offering it. None of the existing players are offering it who didn't already offer it in the past.
And so I feel like it is a little bit of a competitive advantage there where it's like we're going up against other poorer solutions than just the intercoms of the world with infinite money. It's like, no, this can be a little niche that we have some advantages in. Yeah.
No, I think that makes sense. I have a, may seem off topic, but I have a question for you about Laravel because you're written on, well, you're written on some custom PHP that you hacked together 20 years ago, but then I know at a certain point, you know, you integrated Laravel and you're pretty heavily involved in the community. Laracon, you know, I think you mentioned some of that earlier.
Laravel just raised $57 million, like, I don't know, two weeks ago, maybe. What's your thinking on that and what that means for the future of Laravel?
Yeah, so I think it's really exciting. I mean, I run the official Laravel job board. Taylor Otwell, the creator of Laravel, worked at Userscape with me for three years. That's my company's name is Userscape.
I didn't know that. Oh, what a trip.
Yeah, so he... Did he work on HelpSpot? Yeah, yeah. And some other new stuff. In one of my distraction periods, he worked on some new stuff. He worked on HelpSpot. But yeah, I actually found him. He was working at a shipping company. And I found Laravel. And I was like, wow, this is awesome. I want to have a framework to work on new versions of HelpSpot with, as well as other ideas.
And I didn't like any other PHP frameworks, even up to then, which is like 2010 or something like that. So I reached out to him. I was looking to hire a developer anyway. I ended up hiring him. He worked the first three or four months at Userscape, just brainstorming.
building out Laravel actually, like in some of the, in some of the more like enterprise-y things it didn't have already, like caching and some other things. And then, and then, yeah, we did like the conferences together and stuff. And then ultimately he built Forge, which is kind of the main revenue producer at Laravel. It's like a hosting platform or manager and,
Then that started making a lot of money and I was like, okay, you should go run that. And so he did. And then, but we've stayed, you know, close friends and I'm definitely friends with a lot of people in the Laravel community. So yeah, I think, you know, kind of the thing is he turned that into a bootstrapped and very profitable business.
And, you know, it's again, kind of hit that point where like he had some bigger ambitions basically to launch like this thing called Laravel Cloud, which is going to be,
heroku but for php and laravel basically um it's kind of like the shorthand but that kind of thing obviously requires just even if you have a very profitable business it's like ultimately you're going to need you know a lot of very expensive engineers and lots of servers and security people and all this stuff that starts to get into like you know if i'm paying i'm making up numbers here i have no idea
deal with their paying, but if you're paying a security guy $800,000 a year, let's say, or whatever, like that starts to get a lot of money, right? So kind of to chase those ambitions, that's, that's what he's done. So I think so far, so good. Like you said, it's only been a couple months since they raised.
So now I want to ask you something that I asked you offline. And it was about kind of what's your biggest fear, you know, today, looking ahead, you've run this business for 20 years. And you mentioned it was it was like, how can AI potentially impact this? You want to talk us through thinking?
Yeah, so I think this is a topical one, right? So, you know, I think customer service is more directly in the crosshairs of even current AI capabilities to some degree. Like obviously you can make the case for like, well, every job is going to be affected or whatever, you know, who knows? But I think this is one where it's like, it's a cost center.
A lot of companies look at it as, and they're like, okay, if AI can do a reasonable job, maybe we're willing to make changes there. So yeah, I just think it's a big unknown, right? I think so far it hasn't been really disruptive enough at all, but that doesn't mean it won't be.
There's definitely been some companies that made big moves, like Klarna got a lot of press for moving almost all their support to AI. But again, that is a very particular use case where they don't have a lot of different types of questions. Basically, it's like, I want a refund. Like, how do I pay my bill? So I think a very good use case for like an AI. They had poor service ratings to begin with.
So it's like, are the AI people going to do any worse? Probably not. So, you know, you have some differences there. But yeah, who knows? So, I mean, on the one hand, it's like there are those fears of just might consolidate down to a few big AI players who do a fantastic job with it and they just gobble everything up.
Or is there going to be – is it not going to be a thing at all or more of a middle ground where since we have access to a lot of similar technology at least ostensibly, right? We can pay for open AI or whatever else. We can add those tools to – for the most part, I think there's going to be probably some things that are going to be beyond our capability. But –
Yeah, so I think that's definitely just a big unknown. And we haven't had that in a long time. And so to help that space, it's been pretty stable. So this is definitely a new thing that's out there. And it's like, you know, we'll see how it goes. Is it we're definitely adding AI features. And maybe that's just kind of be kind of where it ends up. But we'll see.
That makes sense. What just out of curiosity, like, what's the first one or two AI features you're adding?
Yeah, so very early on, we did kind of like your standard writing helpers. We went farther than most of the other help desk tools I've seen have gone where you can define your own prompts and tools for the agents. But still, it's ultimately more like on the writing and human creation side.
But from there, you know, we're working on doing things like auto triaging, where it can route inbound tickets to the right categories or right agents and things like that. So that's going to be one of the first more sort of offensive-minded, more active AI elements that we're going to be adding.
And then from there, we have some different ideas about how we might do auto-responding in a way that's maybe a little bit safer. So obviously everybody's trying to go for like the holy grail of like The AI just responds, like you give it anything and it can just respond, right?
But, you know, maybe there's some in-between ground there where it's more of a human response, but we use the AI to maybe figure out what's the right response or some different things like that. So some stuff in R&D, some stuff very close to shipping. Yeah, so that's kind of where we're at with it.
But there's a big sort of sea change, much like when I started the company, which is like everybody's using client server apps or just pure email. And that was like the big shift. And now it seems like there might be another big shift. I don't know if it'll be quite. It could be bigger than that. It could be less than that. I don't know. Who knows? But we'll see.
So last question for you today before I let you go. I asked you offline, I said, you're named Help Spot. How did you feel when all these other help desks launched with help, right? So there was like Help Scout and Help somewhere else. And what did you say to me?
Yeah, so those don't bother me at all. There's lots of help, you know. whatever, variations. But I thought the spot was kind of my unique thing. I like the spot. And Dharmesh Shah, who's the co-founder of HubSpot, was in Joel on software with us and kind of in our circles, right? And then he starts HubSpot and stole my spot. And so now it's HubSpot.
And obviously, like anytime I say HubSpot and HubSpot and people get confused, even more than with HubSpot, like help scout, although that one does get confused as well sometimes. But yeah, I'd say in terms of naming irks, HubSpot kind of takes the project.
Sometimes that happens. Sometimes it happens. You seem to have done it. I like Dharmesh. Oh, yeah. Dharmesh is great.
It's all right. He's a great guy.
He's so gracious. And he's still like, when I wrote this ass playbook, I emailed and said, would you, you know, would you give me an endorsement? And he's like, of course. And he gave me this great endorsement. I put it on the cover of the book. It was so nice. You know, it was like, it was like, I've been learning from Rob for years. You should too, or something. I'm like, oh, you're the, ah,
Yeah, it's crazy. He's so good. Yeah. A few times I've talked to him over the years too. It's just like, yeah, he's still like the guy from in the four. You know what I mean? It's like, he's a billionaire now, but he's still kind of just the same guy.
Yeah. Yeah. That's great. Ian Lansman. Thanks for joining me today. If folks want to keep up with what you're working on, obviously help spot.com to see the app and you are Ian Lansman on X Twitter. Anything else you'd like folks to check out? I know you have a few podcasts.
Yeah, the other thing, I guess the other main thing, if you want to keep up with what I'm doing, is mostly technical is my podcast. I do with Aaron Francis and sort of there's a little, it's more like somewhat technical. There's a little bit technical, but mostly it's business and other topics. So it's more entertaining, I'd say. Yeah, so check that out. We have a lot of people seem to like that.
So that's been fun the last year or so working on that. Again, one of my little, I can't really justify it on an ROI basis purely, but it's a fun thing that I get to work on and it's exciting to do. Awesome. Yeah, so check me out there.
Thanks again for coming on the show. Thanks for having me. Thanks again to Ian for coming on the show. And thank you for listening this week and every week. This is Rob Walling signing off from episode 734.