# 106: We've Got ARR!  ## Episode metadata - Episode title: 106: We've Got ARR! - Show: Mostly Technical - Owner / Host: Ian Landsman and Aaron Francis - Episode publish date: 2025-11-11 - Episode AI description: The hosts dive into the 20-year journey of HelpSpot, revealing insights on sustainable SaaS and customer profiles. Aaron shares his surprising Twitter success and the strategies behind it. They discuss the importance of managing customer concentration and how modest subscriber counts can sustain a business. Additional topics include parenting challenges and balancing work with family logistics. The conversation wraps up with exciting updates on Database School and the launch of subscription services. - Mentioned books: [The Intellectual Life](https://share.snipd.com/book/94d2380c-17e6-44f5-876d-87e24f2c088f) by [Sir Antilanges](https://share.snipd.com/person/851dfece-f4fe-41eb-9964-8cba218e59dd) - Duration: 01:14:09 - Episode URL: [Open in Snipd](https://share.snipd.com/episode/3cc7d718-9ab0-4542-89ac-dd1b43f6d67f) - Show URL: [Open in Snipd](https://share.snipd.com/show/7ad45fb4-8aa6-49c2-83cc-bc2327d14b03) - Export date: 2026-02-17T23:24:34 ## Snips ### [From Spam To A Surprise Birthday Invite](https://share.snipd.com/snip/dc9ec419-f2ce-413e-92aa-bf2370971d22) 🎧 00:43 - 05:11 (04:27) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/abce8d37-eb3f-4cf4-94f0-34e17541c4d4" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Aaron recounts getting a Paperless Post invite that he first assumed was spam and then realizing it was a real birthday invite for twins. - The spontaneous decision to attend led to a delightful family outing and new neighborhood friendships. #### 💬 Quote > I get a text message from Paperless Post... Emily Erickson has invited you to the birthday party. And I'm like, OK, I know Emily Erickson, I haven't spoken to her in like 10 years. > — Aaron Francis Aaron Francis recounting receiving a Paperless Post invite and initially assuming it was spam #### 📚 Transcript **Aaron Francis:** get a text message you know several weeks ago uh from paperless post we all know paperless post. It is the modern, you know, birthday party invite software. I get a text message and I'll obscure the names because they did not agree to be on this podcast. We'll call her Emily Erickson. Okay. Oh, very nice name. That's good. Right. I thought of that before. Yeah. Her name is alliterative, but it's a different character or a different letter. And so I thought, all right, I'll come up with an alliterative alternative. Emily Erickson. I get it. I get a text message from Paperless Post. Emily Erickson has invited you to the birthday party. And I'm like, OK, I know in Emily Erickson, I haven't spoken to her in like 10 years. Somebody's address book got hacked. I'm not clicking on this. I'm not clicking on this. First of all, why are they inviting me? Like, I don't keep the household. No, I'm not in charge of the household I got no idea no idea what's going on I'm barely keeping it together in this one bedroom apartment I don't manage the household are you kidding? so I get it ignore it another one comes several weeks later that's like hey just a reminder Emily Erickson has invited you to this birthday party. And I'm like, yeah, I bet she has. Sure. I bet. She probably wants my social security number too, I'm a genius. Yeah. So then I'm going about my business. It's like Thursday or Friday. And I get a text message from an individual, a person that I know. We'll call him Eric Erickson. Okay. **Ian Landsman:** Is he actually the husband? **Aaron Francis:** He's actually the husband. Okay. Okay. Not just happened to be named. Okay. No, **Ian Landsman:** no, no. I get a **Aaron Francis:** text message from, uh, Eric Erickson and things start coming together in my mind and I'm like, Oh, this might be real. And it's one of the twin dads from the restaurant. And he's like, Hey, I don't know if you saw the invite. It might have gone to spam, but the twins are having a birthday party this weekend. And we want you guys to come. Twin And I'm thinking in my head, like, did I know that your wife's name was Emily? Did I know that your last name was Erickson? I just kind of thought you were Eric twin dad, you know, I just in my head and in my phone, you're Eric twin dad. And so I'm like, oh, yeah, you know, it did go to spam, which is close enough to the truth because I thought it was spam, you know, so it didn't go to spam. But I in my head categorized it as spam. That falls under the umbrella of being true. And so I was like, yeah, sorry, man, I definitely you know, thought it was spam. And let me talk to the boss. And so it's Thursday. This birthday party is on Sunday. It's Thursday. And I tell Jennifer, it's tight. I tell Jennifer, hey, one of the, you know, the restaurant twin dads, which is like a category that we talk about, the restaurant twin dads, invited us to a birthday party. It's up in Frisco, which, as you know, Ian, is the suburbs. The suburbs. Come on. You don't even go out there, probably. I don't go out to the suburbs. You're a city person. No, I'm in here. I'm walking around, avoiding poop on the streets. It's the friggin. It's I'm in the city, baby. Yep. And so it's like 30 minutes away. And we're like, you know what? What the hell? Let's pack up the whole family. So all six of us load into the minivan. Last minute drive up north to Frisco, 30 minutes. Great white north, yep. Great white north. We go to Little Jim, which is, you know, a a kid's, you know, gym. Oh, man, I miss Jim party. We get there and I swear we're like 20 to 25% of the attendees, our family of six. And it was the best, most fun birthday party ever. All four of our kids are having a blast. They're excited to see us. We're like yucking it up with them. And like Jennifer's finally getting to spend some time with the wife whom she's met one time at the restaurant. And I'm hanging out with the dad. We're laughing. We're joking about vasectomies. You know, we're just we're shucking and diving. It's great. And so it was just like the most serendipitous, best birthday party we've ever been to. The kids are having a blast. Everybody, you know, they get the big parachute out. We're doing the parachute up and down. the parachute. We're singing wheels on the bus and spinning it around. Oh, good. And I'll tell you what, the twin dad restaurant connection pays off again. This is crazy. It's crazy. friends. You actually went out there and made real friend at --- ### [Introduce Yourself To Make Connections](https://share.snipd.com/snip/22337da9-2b6d-4d51-9163-68f3c8381158) 🎧 05:22 - 06:30 (01:07) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/8e5d7933-6747-4470-99d7-1d05f6dffe22" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Introduce yourself to other parents using an easy, natural opener like noticing twins. - You can form real friendships and get invited to events by making small social gestures. #### 💬 Quote > You walk up and you say, hey, are those twins? boom, you're off to the races. > — Aaron Francis Aaron Francis on how to start conversations with other parents at restaurants #### 📚 Transcript **Aaron Francis:** I You walk up and you say, and this works better when you have twins, I will admit. But you walk up and you say, hey, are those twins? boom, you're off to the races. You know, **Ian Landsman:** you can use it. **Aaron Francis:** They just turned three. So they're right smack in the middle of ours. Ours are about to turn two and the others are four and a half. And so it's just perfect. Potentially as a single man, I wouldn't go up to parents and say, hey, are those twins? That's just a little, you know, it's situational. What about there? That could be inappropriate. Yeah. Read the room, read the situation, find a point of commonality and approach a stranger. You never know when it'll lead to a birthday party and the eventual learning of their last name. So now he's in my contact book as Eric Erickson, comma, twin dad. So now we know. **Ian Landsman:** One could say you could just do things. You can just do things. **Aaron Francis:** You can just make friends and get invited to birthday parties and show up. And turns out people are nice and wonderful. And the world may be going to --- ### [Twenty Years Running HelpSpot](https://share.snipd.com/snip/e98fb6af-0836-4502-bbf4-b4c22d60d770) 🎧 22:40 - 25:52 (03:12) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/acbfb677-b6b5-4373-98ae-7552ada1fd28" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Ian reflects on HelpSpot's 20-year run and how it feels both long and like it always existed. - He credits a small, stable team and long-term customers for sustaining the business. #### 💬 Quote > It's having these similar conversations we have on here and you don't know what's going to happen. And then the years go by and then you have kids and you're busy and the years just keep going by. > — Ian Landsman Ian Landsman reflecting on two decades of running HelpSpot #### 📚 Transcript **Ian Landsman:** Yeah. 20th anniversary of Help Spot. That's right. October My birthday. **Aaron Francis:** Speaking of the SaaS dream, years of running an internet business, that is no small feat because internet years are like dog years. That's like 140 years of running a business so tell us how's it feel it's good it's **Ian Landsman:** crazy it's uh i don't even know what i feel about it's like kind of not it's like so long that it just it always has been right you know you don't really want to be in the place where it always will be because that's not you know, how things work necessarily. But I mean, it's fine. We're doing fine. Hopefully that remains true. But yeah, I don't even know what to say about it. It's such a weird thing. It's like, it feels like yesterday I was talking about it. It's these similar conversations we have on here and you don't know what's going to happen. And then the years go by and then you have kids and you're busy and the years just keep going by. And all of a sudden, you know, 20 years you've been slinging the SaaS game and people have been using your software and getting stuff done across the globe. So **Aaron Francis:** when you started, you were young and broke. And if I recall, you had a kid or you were about to have a kid? **Ian Landsman:** When I very first started coding, we not have a kid. And then when Jamie was pregnant, when we released. So, but he wasn't born until the following June. So it was like early. **Aaron Francis:** So, and then since you released, you've been working on it full time, right? Yeah, **Ian Landsman:** full time. I mean, it was like double full time for the first like three years. And then, you know, since then, it's like we have some employees. So which is the thing I want to explicitly thank. I did. I wrote a little blog post about this in the show notes if you haven't seen that. But definitely want to thank all the employees who've worked at Userscape over the years and the current employees just literally would be impossible without the employees. And so that part is really cool, even though we've never been a very large team. It's just like we have this core group and most of the people have been there for many years over time. Even the people aren't there, several of them were there over a decade. And so, yeah, it's cool. It's just like a little family. I'm still in touch with a lot of the people who used to work there, obviously. And it's great. So it kind of been this little community. Some people have gone off and done bigger things out of Userscape, which is really cool and love to see that. Yeah, but customers have been great. We have customers who started with us before the iPhone existed. That to me is like one that really sticks in my head. Like that's crazy. Like the iPhone did not exist. These people laid down money for help spot. And then every year since then they've been paying for help spot. It's wild. **Aaron Francis:** That is crazy. **Ian Landsman:** So yeah, you know, part of it is just getting good customers, getting, having a product that like people utilize and are happy with and like a good customer service, like being on top of that stuff is super important. And I think people get so caught up in like all the other parts of it. Like we got to compete with OpenAI or Linear or like none of that stuff. So much of that stuff doesn't actually matter that much. It's like if you can just get a few good customers, keep them happy. **Aaron Francis:** Yeah. It's all you need. So I was talking to an IRL friend here who --- ### [Serving A Specific, Practical Customer](https://share.snipd.com/snip/660008f4-8ba2-444e-968a-c7a2290eca71) 🎧 25:34 - 28:31 (02:56) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/b4373ac1-a231-4f3c-a983-e548cf66a8f3" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Focus on a few good customers who need your product rather than chasing every startup or flashy feature. - Simplifying the product for real users reduces training needs and keeps customers happier long-term. #### 💬 Quote > If you can just get a few good customers, keep them happy. It's all you need. > — Ian Landsman Ian Landsman on HelpSpot's customer focus and product simplicity #### 📚 Transcript **Ian Landsman:** And I think people get so caught up in like all the other parts of it. Like we got to compete with OpenAI or Linear or like none of that stuff. So much of that stuff doesn't actually matter that much. It's like if you can just get a few good customers, keep them happy. **Aaron Francis:** Yeah. It's all you need. So I was talking to an IRL friend here who listens to the show and he was like, what is how does Ian compete with like HubSpot or Jira or something? And was talking about one, the on premise stuff that you've been, you know, uniquely doing for a long, long time. two, I was and I don't know if I was accurate on this. I was talking about how your customer profile is a little different than like just random internet startup. So like who are your main like industries? And do you think what you did is still doable, like repeatable today? **Ian Landsman:** Yeah, so the main industry, definitely this is a very important aspect, I feel like too, for small businesses. Like when you try to just go after the startup, they're similar to developers, like they're very finicky. They're not very valuable because like the startup doesn't have many people in it usually. Right. So it's like you're doing a lot, jumping through a lot of hoops for these companies that aren't going to pay you that much money and are probably going to leave as soon as somebody else comes up with something that's like slightly fancier or sexier or whatever. Right. So like um so yeah we've always had a bunch of like manufacturing companies higher education's a big one but **Aaron Francis:** i told him i told him higher education yeah **Ian Landsman:** higher education is of our biggest ones um you know there are some software companies in there there's uh there's like a how do get **Aaron Francis:** into manufacturing companies, though? Manufacturing in higher education? **Ian Landsman:** Because it's not like, we've never gone after specific, and we have like pages about those verticals and things, but it's mostly just SEO and people looking for it and then they find it and then they happen to be in those industries. Those are industries that are looking for these type of solutions in various ways. And so, I mean, listen, Zendesk, I'm sure, has a bunch of manufacturers too or whatever. So it's not like we corner the market on that or anything. I mean, we have like 500 customers or less than 500 customers probably. So, you know, it's more just that we have this broad array of customers and it's more, the similarity is more of like what they want to do, which is lots of email, but not a lot of the other stuff. So like they don't want Facebook, they don't care about Facebook integration. They don't care about Twitter integration. They don't care about all that type of stuff. Like they're not really into that end of it because we don't do any of that stuff. So if you want that stuff, then you have to go to one of these other bigger tools that has all that stuff. The downside of that is like those tools have all that stuff. And so if you don't use any of that stuff, now you're paying often for that stuff. It's just the interface is full of random stuff you're not even using. The **Aaron Francis:** confused by it. Right, yeah. **Ian Landsman:** Like HelpSpot, part of its big thing is like you can just drop your staff in there. And it basically kind of looks like Gmail. And there's not a lot of other stuff going on that they're going to get lost and confused. Like you don't need a lot of training and all that stuff. --- ### [Longevity Beats Chasing Trends](https://share.snipd.com/snip/6533bb7f-8358-453a-9aa6-2125fe1d39f8) 🎧 28:36 - 32:32 (03:56) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/d024607a-40c8-4ca6-9ec3-4ea307e25f40" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Longevity comes from showing up, adapting, and refusing to give up during new tech waves. - Staying small and profitable can be a deliberate and sustainable goal, not always scaling to infinity. #### 💬 Quote > Just don't die. Yeah, just do stuff and refuse to not do it and just keep going. > — Ian Landsman Ian Landsman on surviving SaaS cycles and technology trends #### 📚 Transcript **Ian Landsman:** Yeah, I think part of it is just the world's a big place. Like I said, we have like under 500 customers. **Aaron Francis:** That's crazy to me that you have employed a bunch of people and you've made a life for yourself for 20 years on under 500 customers. Yeah. **Ian Landsman:** I mean, time, it's probably more like whatever, let's say a couple thousand customers over 20 years, right? Because people come and go, whatever. But yeah, I mean, that's still not many, right? Like there's plenty of companies that have 20,000 active customers or whatever. So like, yeah, you don't need that many. That's the thing. If you sell something that you could sell, sometimes people, the minimum they pay you is like almost $1,000. And then you have sometimes they're paying you 30, $40,000, you don't need that many to get to a million or two, you know, like it doesn't take that many to do that. So that is also a nice thing. Whereas, I mean, when you're trying to reach individuals and things like that, it's like, well, I need 10,000 of these individuals to each, you know, pay me 10 or 20 bucks a month to start to add up to those bigger numbers, which is much harder. Yeah, that's kind of it. I mean, I think it's much harder than when I started, you know, even in these, these kinds of spaces where there's every company needs this product. There's now lots of companies that service this need also. So when I started, like there's definitely the luck factor there of like, Hey, I got on this before other people. We had a lot of people come in early. A lot of our big customers are still have been paying us for 20 years, you know, anywhere between 15 to $30,000 for 20 years. Right. **Aaron Francis:** So like that all adds up. So, yeah. So there are some customers that have paid you north of a half million dollars over 20 years. I **Ian Landsman:** don't think any probably got quite that big only because like in the early years the most you could pay us wasn't quite that high. Probably it was cheaper then, so the price has gone up over time. But there's definitely some that have paid us, I would say, close to $300,000 is probably the most, if I guess. That's awesome. a little more than that. But yeah, so you get one or two. This is where there's the 37 Signals idea of you should never have any big customers, which I don't really believe in that. I do the extreme of that. Surprising. The extreme of that version I do agree with. If you start doing custom stuff for one big customer type of thing, and it's like, well, we'll pay you half a million dollars. And now you basically just work for them. And yeah, you have other customers, but this one big customer is everything. And then they could just leave one day, and now you have to fire everybody because your one big customer is gone like that is not a good spot to be in but i would still take the money if i was you but like there is more downside risk of course but uh but yeah but when you have a company that's maybe one percent of your revenue or two percent of your revenue or something like that or you know half a percent or whatever it is you know i mean it hurts if one of those leave but it's you know you don't have to like make any changes either like it's like okay like that's unfortunate but it's fine so yeah i think that's that's been like just i don't know i don't know it's hard to like pull lessons out because it's now becoming such a long time that like some of these it's like multiple cycles it's like there wasn't even sass when i started and there was sass and everything was going to go SaaS, which I think this is an interesting of staying in the game element of it. It's like, oh, everything's going to go SaaS. We don't know how to do SaaS. We're going to go out of business. And then, you know, we didn't go out of business and we kind of figured out SaaS well enough and we kept moving. And then sort of on-premise started to come back a little bit because people had like the security concerns and stuff. So that's been interesting. And ONCE.com. And because of ONCE.com is the other reason, yes, of course. We must give credit where credit is due. Once.com. Then you had AI a couple years ago. was like, oh man, everybody's going to use AI. AI's going to answer every question and then don't need us anymore, but that hasn't been the case. Just don't die. Yeah, just don't die. Just do stuff and refuse to not do it and just keep going. That's pretty impressive. don't have something that's working a little bit, you know, you can't, if it's not working, that's a different situation. But if it's working a little bit, then you can just kind of keep going and maybe you don't get as big as you hope or whatever, but you can still make it all work. --- ### [How To Apply For HelpSpot Support](https://share.snipd.com/snip/a95724be-6784-4647-bae9-522030d48288) 🎧 37:27 - 40:52 (03:24) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/262a199b-d57d-4c78-8a1f-7eee572a09f4" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - If you apply for the HelpSpot support engineer role, highlight customer-facing experience and Laravel backend skills. - Show familiarity with working directly with customers and troubleshooting on-premise setups. #### 💬 Quote > The primary function of this job is that you will be working with customers the vast majority of time. the So you have to be okay and not just okay, but like happy to be helping people and doing that part. > — Ian Landsman Ian Landsman describing the support engineer role and candidate expectations #### 📚 Transcript **Ian Landsman:** do have one other little help spot thing I just want to talk about quickly, which is that we are hiring a support engineer. So if you want to work with me, you could work with me. Then apply over at, well, you can on larryjobs.com and it's at the top there uh we'll put a link in the show notes as well but uh yeah support engineer so it's going to be primarily supporting the customers uh and primarily we don't get we get a little bit of like how do i do this type of stuff so there's that um there's running onboardings uh but a lot of it is like more technical, like really helping on-premise people who have a weird situation, you know, bugs. If the person ends up being a developer, which is our goal here, there'll be bug fixing and things like that. And an opportunity to learn a lot of different things and be involved in HelpSpot's future. So interested in that? Fully remote? Fully remote. Which I'm so excited. I'm sorry to all the listeners, but I'm so excited you're all being forced to go back to the office because for 15 years. Your Yes, for 15 years, this was like a huge advantage we had was fully remote. And then everybody went fully remote. And now you're all going back to the office. So once again, we are back in it being an advantage, which I'm very happy about. **Aaron Francis:** Walk the hallowed halls of Taylor Otwell, Ian Landsman, Chris Fideliper, Fadau. Lots of great people have come through. Eric Eric Barnes. **Ian Landsman:** I forgot he worked there. Stenson, our current big dog that you just gave. So yeah, we have a lot of well I forgot that those guys worked there also. **Aaron Francis:** Yeah, go to the OG Laravel shop. So larajobs.com is the best way find it. just It's at the top **Ian Landsman:** there. And yeah, and you know what? What of like server? Don't ship. You're going to come here and just. If you're tired of shipping, I've got the perfect job for you. Yeah, exactly. **Aaron Francis:** Have you been shipping too much? What are we looking for? Like server experience for on-prem, developer? Like what kind of level of expertise do we need here? So we've gone **Ian Landsman:** different routes with this in the past with this role, but this time we're trying more of a like more regular Laravel developer experience. So like some Linux experience, but not like not you were a server administrator or anything like that. If that's also fine too, if you have been a server administrator, that's also an okay, you know, good background to have, but it's not a requirement. **Aaron Francis:** So we're looking for like, like right down the middle back end type experience. **Ian Landsman:** Yes, exactly. And I mean, I would say the key aspect of this is I know that there's a lot of developers out there, but the really key thing to internalize here is that the primary function of this job is that you will be working with customers the vast majority of time. So you have to be okay and not just okay, but like happy to be helping people and doing that part. And then in addition to that, you also know how to develop on some level. It doesn't, you don't have to be, you know, a senior developer, even just like more basic experience, I think is fine. But that's kind of the goal of what we're looking for here. So we did put the job out middle of last week, I think, and we already have had some good applications. But we haven't started getting back to people yet. want to give a little time, get on the show, give that a couple days, and then we're going to start going through them. And Matt Stenson is kind of the point person on this, of the hiring process. He's doing most of the legwork there, going through everybody and figuring out who's going to be a good fit. It is only one position. --- ### [A Viral Tweet About A Dream Studio](https://share.snipd.com/snip/fa414ed8-772a-4e8d-aee0-04b4af7d8a4e) 🎧 43:09 - 47:18 (04:09) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/d71d4110-f574-4b57-9f76-3be0b40e9575" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Aaron describes a tweet about wanting an old industrial building that unexpectedly went viral and reached millions of impressions. - He attributes success partly to luck and emphasizes tweeting spontaneously rather than over-optimizing timing. #### 💬 Quote > I tweeted 'men only want one thing'... and that thing is an old industrial building to turn into a studio. I woke up and it has exploded. > — Aaron Francis Aaron Francis describing his unexpectedly viral tweet about an industrial building studio #### 📚 Transcript **Aaron Francis:** It was very strange. So I think something has changed with the algorithm. Okay. I don't know what it is. I have no idea i i have not changed my behavior but i tweeted i'm just scrolling back um i tweeted on november 2nd so this is eight days ago at 8 50 p.m on november 2nd so it's like this is this is clearly this is 8 50 on a sunday night So if you had terrible time, if you had to pick a worse time, I don't know what you would pick. Literally the worst time. Literally the worst time. And goes back to my this goes back to my my dearly held belief that you should just tweet when it comes to your mind. Do not try to be an optimizer guy. Don't fill up your calendar with every Monday at 11. You have a pithy inspiration. No, just tweet when it pops in your head and go on about your day. I tweeted men only want one thing, which is a callback to an Internet meme of guys only want one thing. And it's disgusting. It was a woman complaining about men. The original tweet is lost to history, but it's taken on a life of its own. It's like men only want one thing. And then it's like, you know, a giant sword from the 1400s. And it's like, oh, okay, we're doing a meme now. So I'm playing on a meme. Men only want one thing. New line, new line, you know, you know, create a little breathing room there. And that thing is an old industrial building to turn into a studio. And I just went, I just went on Google images and searched brick building. I thought this was a building **Ian Landsman:** you knew. No, **Aaron Francis:** I found one that I was like, oh, that's the dream. I want like, I just looked until I saw one that was like, I could totally live there. And I copied the image from Google photo or Google images and pasted it and fired it off at 8 50 PM on a Sunday night. And then I go and I, you know, I get on my, my traction device, my torture machine, I'm stretching. And I go, I check and, you know, I lay in bed, I check. It's like, Oh wow, people are liking this. All the normal, like all my friends are like, Oh God, I really want that. That's great. I go to bed. I wake up the next day and it has exploded. It has just taken on a life of its own as it stands today. Eight days later, a million impressions, five million impressions, eleven hundred retweets, teen thousand likes and six hundred comments. And I'm like, what is happening here? This makes no sense whatsoever. And then, so there are some quote tweets that get, I think one of these quote tweets has a million views. So this guy did what I'm talking about and he quoted it with two pictures and he got a million views. But then I had another tweet and this is just the strangest. So I don't know what's happening. I had a how it started how it's going that's reached a quarter million impressions and then i had one uh another play on a historical quote i said if you owe the bank a hundred dollars that's your problem if you owe the a hundred million dollars that's the bank's problem which is the historical quote by j paul getty and then the final line that i added is if you owe the bank $100 billion, that's the government's problem. And it was a quote about OpenAI requesting government backing. That one has 930,000 views. I'm like, guys, this is not that interesting. And so it's very strange good yeah i don't know i mean they're good they're good tweets but i um so i count a tweet as like man that was really awesome if the number of views exceeds my number of followers and so that's kind of like that's how i kind of you know categorize it's like oh that was a that one did really well and they're just like they're just popping off now. And I don't understand, but I'm happy. And here's the thing. I haven't changed my behavior whatsoever. This is the exact same game I've been playing forever. Just tweet what comes to mind. And I wrote a little bit about this in my newsletter. And I called it games of luck and games of skill. And Twitter is just a game of luck. --- ### [Twitter Is Luck, Not Reliable Revenue](https://share.snipd.com/snip/a6e6e33c-38a8-40df-b3b4-7cc5efe8e67a) 🎧 47:18 - 52:33 (05:14) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/f886e7ef-6984-465b-bb83-2a97a6277c0d" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Treat Twitter as a game of luck where volume increases chances of a breakout, not a reliable sales channel. - Use social platforms for relationships and reputation, while relying on other channels for predictable revenue. #### 💬 Quote > Twitter is just a game of luck. I think there's some skill involved, very little. > — Aaron Francis Aaron Francis distinguishing luck vs. skill in Twitter success #### 📚 Transcript **Aaron Francis:** I think there's some skill involved, very little. But with a game of luck, the strategy is just play as much as you can if it's basically free to play and Twitter is free to play. And so I just keep tweeting. And you know what? Sometimes good things happen. I'll have to report back on the next creator payout to see if it actually made any money or whatever. Are you on that? You're in the creator payout **Ian Landsman:** system? Oh yeah. Yeah. Okay. **Aaron Francis:** I don't get very much. I'm looking right now. I **Ian Landsman:** saw the poker reference in your newsletter by the way which **Aaron Francis:** I saw. Uh huh. It's a game of skill. With some luck. My total revenue. This is insane. My total revenue from creator payouts is $5,000. **Ian Landsman:** Okay. **Aaron Francis:** Better than a poke in the eye. looks like each two weeks, the last two week periods have been around $300 each. And then before that, it's between $1 and $200. But as you and others will know, I refuse to pivot into like rage bait because the real value of Twitter is the relationships, the reputation, the other business deals. And so if I were to like become rage bait guy just for a couple extra dollars from Elon, that would be a miscalculation and against my things that I hold dear. So it's nice to get paid. Did **Ian Landsman:** pick up followers from this, though? I did. **Aaron Francis:** Not terribly many because it's kind of outside of the middle, but I think I probably added 12 or 1300 followers, which, you know, I'll probably churn some of those when they realize i don't tweet about buildings that often but i'm okay with that uh you **Ian Landsman:** worry about the thing i worry about with these things is just like it makes you feel like you accomplish something oh yeah **Aaron Francis:** that's bad but right but **Ian Landsman:** like you haven't necessarily accomplished anything with it right so like that's the part that i always like feel like even when i was in the twitter game which obviously now i'm not But like you're always just like, oh, like, oh, that's cool. It's exciting. And then you're like, but I don't know how I turn this into money. Exactly. I mean, like this goes **Aaron Francis:** back to our sweet hang with Jeffrey, where it's like doing conference talks is the exact same thing. It's the exact same thing. It's like, oh, I spoke at this big conference and everybody loved it. And it's like, okay, where's the mortgage money come from? It's like, oh. And so it's the correlation between like attention and money is still very diffuse. Right. And so there have been times where I've had something do really well and sales just tick up. Right. And I think there is a correlation there. I don't think the, the, whatever the, what is that? The P value? What's the correlation value number or letter? Is it P? Yeah, **Ian Landsman:** there's something there. **Aaron Francis:** Something like that. I don't think that approach is one. I think it is like very, very, very low. But in some regards, I am in the like awareness and attention economy in that I need more people to be aware of me so that I can, you know, sell them my wares. So I don't count it all for naught, but it is it is the weight that it like occupies in my mind and psyche is higher than it deserves for sure. It **Ian Landsman:** seems like the thing is to try to get this skill to then like, even if it doesn't blow up to 5 million views, but like if this was about databases, right. If this like, if the punchline was like, uh, indexes, you know, and like whatever, right? Now that's going to like reach the group that you're actually selling stuff to. And that's your way into those people. And yes, maybe they're not ready to buy a Postgres course right now or whatever, blah, blah. But like now you're gathering those people up as opposed to just like totally random internet people who like buildings or whatever. So, yeah, like whether or not the algo rhythm will support that is, you know, I don't know if that's true. It might not be true where it'll push it, but. **Aaron Francis:** Yes. And so I will say for the dear listener, this is not a good business strategy. Like don't, **Ian Landsman:** don't try to. It's cool as its own thing. It's **Aaron Francis:** cool as its own thing. It's fun. I enjoy it, But I am not going to like if you scroll my feed, you see, you know, the picture of the building. You see talking about the book, The Intellectual Life, The Dominican Monks. You see pictures of my kids. And so my strategy is and has been and will remain just be Aaron, but online. That is the extent of my strategy. And so like, if you scroll up, there is one where I talk about, uh, um, my face, when you tell me that you're using UUID V4 as a primary key. And like that one got 200,000 views. And that is a, that is a database one. That is fully a database one. And so that's good. But then the next one was talking about OpenAI, or I'm sorry, Claude is hiring a DevRel person for $305,000. And then the next one is talking about the Dominican monk that created the Midwit meme --- ### [Database School Achieves First ARR](https://share.snipd.com/snip/3237e7df-7d4d-4170-9f5e-137ffa257734) 🎧 53:27 - 55:37 (02:10) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/18720f7e-4a5b-4443-8eec-fbd31b9b6c80" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Aaron announced Database School subscriptions and revealed $2,000 in annual recurring revenue from pre-orders. - He frames the early ARR as modest but meaningful proof the subscription model can start immediately. #### 💬 Quote > We've got annual recurring revenue. It's not a big number... It is $2,000 in annual recurring revenue pre-ordered. > — Aaron Francis Aaron Francis announcing pre-ordered ARR for Database School subscriptions #### 📚 Transcript **Aaron Francis:** So I probably have five more videos to do. OK. Which I'll That's like. Yeah, I'll get done. I'll get those done today. The edits are looking great. He's already doing them, doing them as they come. Nice. losing AirPods, so I'll charge one while I talk and the other. The edits are looking great. We sent out an email, Kelsey did, sent out an email that says like, hey, coming soon, do you want to subscribe? Because we're going to go to subscription. And if you, yeah, I know. If you subscribe early as like a true believer, you get a discount. And so people have subscribed. People have. What? We're already getting revenue? We've got annual recurring revenue. **Ian Landsman:** Yeah. Well, first of all, hold on. I didn't even, I don't think I got this email. I have to check to see if it got filtered off. I do have a bunch of heavy filtering in but I usually get your emails. So that's weird. don't know. **Aaron Francis:** Maybe I was not a group. I this went to. Okay. I feel It is possible that this went to, it's possible that this just went to the people who signed up for Intro to Postgres, like the new people. Oh, okay, yeah. So I don't know exactly. There are a bunch of launch sequences planned. Right. Um, Kelsey has all that worked up. Um, but some will go to the people, the new people. Some will go to people that have purchased. Some will go to people that are just on the Aaron list. So that kind of thing. Kelsey messaged me this morning and said, you've already got, uh, you've already got, I think it was, and now this is ARR. It's not a big number. So nobody feels sad for me. I'm aware of that. It is $2,000 in annual recurring revenue pre-ordered. So they've signed up for a subscription that will renew in one year. And I'm sure the churn will be high. That's fine. That's fine. But we're making, we have left the launch pad on subscriptions. **Ian Landsman:** We buried the lead here. I didn't know we were launching the subscription service this week. Holy You know, you **Aaron Francis:** don't have to just talk about it. You can just be about it. I just did it. We just freaking did it. Wow. Kelsey and **Ian Landsman:** I mean, $2,000 is huge. I know. That's great. I mean, it didn't go out even to everybody. --- ### [Launch With Annual Plans To Build Commitment](https://share.snipd.com/snip/4e0773eb-e40f-45d7-bbc3-f766805e37da) 🎧 55:51 - 01:00:55 (05:03) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/406cd5b7-3ac9-45ce-b7ad-dfcbb42b8862" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Start paid subscriptions as annual to build committed users and simplify content planning. - Use existing course buyers and newsletters to convert early adopters while offering free content to attract newcomers. #### 💬 Quote > I'm going to start with just annual. It's like well within reasonable education budgets for companies. > — Aaron Francis Aaron Francis explaining the decision to launch Database School with annual subscriptions #### 📚 Transcript **Aaron Francis:** it monthly or is it annual? So it's an annual. a annual. The subscription is annual. And so we won't know churn until, you know, one year from now. And I expect it to be relatively high. But that gives me the opportunity to prove myself in that year. **Ian Landsman:** Is that going to be the plan? Is it only annually subscription? Or it **Aaron Francis:** monthly? At Yeah. Okay. So I'm going to start with that just to, because I do have to build the base, you know, of content. And so I will start with just annual. It's like well within reasonable education budgets for companies. So I don't anticipate it being a problem. And as time goes on, I might offer the monthly. But yeah, for the start, it'll be just annual. And so I logged into Bento, bentonow.com and I looked up, um, I like looked at our account cause I don't do that terribly often. I write the newsletter personally by hand. It's not AI, but I write it in Google docs and throw it over the wall to Kelsey and she like handles that. And so I don't log into Bento terribly often, but I logged in to Bento and our project name is, I think it's like Francis Empire or something. It contains, you know, my personal, it contains database, it contains screencasting. And deduplicated across all of those properties, the number of individual email addresses that we have is north of 20,000 people. Wow. **Ian Landsman:** Okay. And I was shocked. I was shocked. You're not doing enough with those 20,000 people. **Aaron Francis:** No, not even close. I need more people to be unsubscribing because I'm sending so many emails. Yeah, it's awesome. And so that, of course, includes every person that has purchased a course. So it's not just like voluntary signups. It's like you a course, we add you to the list so we can send you emails about it, which is legal, but it's not like, you know, they, you know, went to some page to sign up for a newsletter. That does include many thousands of people on the personal newsletter, which is crazy. Wow, you're **Ian Landsman:** up to that many already. Yes um **Aaron Francis:** so i am that's a nice that was a nice surprise i feel like this is like all signs are all signs are pointing the correct direction um and so as it's feeling like you know we turn the corner we turn the corner whatever episode that was two three ago the corner is in the rear view mirror. It's gone. I can't even see the corner from **Ian Landsman:** where I am. I love that. This is like a you just hang around kind of thing, right? Like you put up some newsletters, subscription boxes in various places over various years and like you just hung around and you kept doing some interesting stuff. You weren't like promoting newsletter every two minutes and every tweet and whatever. Yes, no auto responder. Organically built up to 20,000, which even if, okay, 15,000 are active and legit and like are going to respond and stuff. Great. That's 15,000. 15,000 **Aaron Francis:** direct connections. **Ian Landsman:** You're to sell to those people. Yes. And all those people are from you and your stuff, which has been mostly in this general realm in one way or the other. Should be very promising now i love this this is great we got crazy we got stuff happening i believe good the leads good these are the glengaria leads that's right this is a little like a counter culture kind of thing but we've only also ever had annual subscription we've never had monthly and i have toyed with monthly, but we never actually launched it. I do. I love the annual. I don't know. I think it's like, I mean, I don't know. I just think the buyer is more committed. Like for my stuff, it's a little different because like you're not going to implement a helpdesk app unless you're fairly committed to begin with because it's a lot of work. But still, I think that it's good to have that alignment there. And like if you can get away with just only selling annual, I think that's fantastic. Like, so if that ends up just working, that's great. Like, just stick with that and maybe have a lifetime or something too. I can see a lifetime in your case working. **Aaron Francis:** My theory is that the annual will work out just fine for now because it is either the price of a single course or less than a single course. And so it's like, hey, do you want to buy, these won't be available for sale individually, but like, do you want to buy high performance SQLite for $199 or do you want to buy a year to this platform for $199? It's like, oh, I'll just buy a year and watch all the videos. I'll watch these on Redis. watch these on SQLite. I'll watch these on generic indexing. And so I think it will occupy a good space in the buyer's mind. Now, of course, the further away we get from remembering the individual courses of errands cost north of $200, the more pushback we'll get on. I got to spend $200 to even walk in the door. But even that's not true because there will be a lot of free content. And so hopefully they'll become addicted to what I hope is very high quality, high value education. And then they're like, oh, $200 for access to all of this stuff. That's a no brainer. So that's my operating thesis. --- ### [Medium Wins Stack Into Longevity](https://share.snipd.com/snip/743f217b-2a69-4954-ad1b-e1a647f1494a) 🎧 01:04:54 - 01:07:51 (02:57) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/d1187f1e-a236-476b-9a4c-5d602a0b191c" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Small, repeated efforts and medium successes compound into long-term business stability. - Shifting from high-stakes launches to steady work reduces existential risk and supports gradual growth. #### 💬 Quote > You can just try to hit a medium note and sometimes it'll turn into a high note and sometimes it won't. And sometimes a medium note is just fine. > — Ian Landsman Ian Landsman on steady work and incremental progress over big launches #### 📚 Transcript **Ian Landsman:** Dude, you're launched. This is blowing my mind. I didn't know we were launching today. We're pre-launched, we're pre-launched again. Yeah, but you're collecting money. This is not like pre-launched like we're collecting emails. We're collecting money. No, **Aaron Francis:** and I don't know if it was explicit or just implicit, but getting away from like the massive spikes of launches, I feel like we're already doing that like we just sent email to people that expressed interest and said you can sign up now and it's like i didn't have to do a live i didn't have to do a launch video it's just like we're just running a business here of course i will continue to try to generate hype because hype is good for for business and hype is fun um but is a little different. I'm no longer like tied to it, which feels like a relief. Well, **Ian Landsman:** I think there's also like there's like when you're doing a launch for the course, it's like this will succeed or fail, period. Yes. is not anything else to it besides success or failure. when Right. It's not fun. If you do a launch style video or live stream or something for a new course in this and it fails, it's like, OK, well, this was an experiment. We tried on to the next. We already have some customers paying us a baseline. This thing didn't work. Now we will know to do this part different next time. We'll try it. It's just part of the ongoing experimentation instead of like this is. the **Aaron Francis:** catalog and keep on trucking. **Ian Landsman:** Yeah, it's totally different than like, oh, man, I put my heart and soul into this. It failed. I made no money. Now I have to go look for a job or do whatever. my has to go look for a job. Right. Or something, whatever, like all that kind of stuff. So it's like, no, this is just a marketing activity I did. It didn't work this time or it did work and we're going to do more of it or whatever. And okay, take that into consideration going forward. And that's it, because you're just running a day in, day out business. And it's not every every single thing isn't so high stakes. It's just another thing you tried and you go on from that one way or the other. So and **Aaron Francis:** this all this all comes back because it's very fresh in my mind, to this book I've been reading, The Intellectual Life. And it all talks about focusing on the work day to day. You need to sit down and do the work day to day. And this feels like, since my vision quest and the blocking of social media and then being exposed to this book, it just feels like I'm narrowing in on the daily activities of work are the important part. And I think for so long, I've just been like, the big launch is coming. I have to put all my hope into this big launch, the big set reveal, the big shed build out, the big blah, everything. It's always the big thing is coming. And I'm finally being able to like, put my head down a little bit and be like, today, I will work on this. And this is my job today. And it's like, oh, that's, that feels good. That's a relief. Yeah. **Ian Landsman:** Yeah. And then it's like, yeah. And then you just do that and it's 20 years later. --- Created with [Snipd](https://www.snipd.com) | Highlight & Take Notes from Podcasts