# 136: Big, Audacious Goals  ## Episode metadata - Episode title: 136: Big, Audacious Goals - Show: Mostly Technical - Owner / Host: Ian Landsman and Aaron Francis - Episode publish date: 2026-06-16 - Episode AI description: They debate the Great DJ question and event vibes. Travel plans and a Laravel Live UK talk preview come up. A founder explains why he raised HelpSpot prices and the tricky math and billing behind it. New Solo pricing and team plans get detailed, including Stripe headaches. They react to the sudden shutdown of Fable 5 and discuss sponsorship systems for podcasts. - Duration: 01:15:40 - Episode URL: [Open in Snipd](https://share.snipd.com/episode/56ef0c16-be2c-4c85-9d6f-92e07090b57e) - Show URL: [Open in Snipd](https://share.snipd.com/show/7ad45fb4-8aa6-49c2-83cc-bc2327d14b03) - Export date: 2026-07-08T01:11:42 ## Snips ### [Raise Prices With A Clear Case And An Out](https://share.snipd.com/snip/6dd790ca-80f0-457d-b40e-02132f12310e) 🎧 14:21 - 16:53 (02:31) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/fa97a3d8-7add-4b03-a842-26f797023318" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Raise prices on existing customers when your product delivers more value and costs rise. - Ian increased HelpSpot ~25% with a clear email explaining added features, future roadmap, and offered an easy opt-out to avoid churn. #### 💬 Quote > You got to make the case. When you don't make the case, it goes disastrously. > — Ian Landsman Ian Landsman on how to raise prices with communication #### 📚 Transcript **Aaron Francis:** All **Ian Landsman:** right. This week, we raised prices on HelpSpot. And I thought it'd be just a fun little business topic. We haven't really done a needy business topic like this in a while. Like, should you raise prices? How you raise prices? And the biggest thing to me, I just wanted to bring this up because I know so many software developers, founders, whatever, the whole thing, who never raise prices on their existing customers. And to me, it's like a humongous, gigantic error of mega proportions. So I just want to bring this up. You can raise prices on your existing customers. You should raise prices on existing customers. Nobody likes it when you do, of course, but like I've talked about this on here before, Bugsnag is still charging us $30 from 15 years ago. We started using Bugsnag. I can never leave Bugsnag. Century sounds great, but I can't leave Bugsnag because we literally put millions of events in Bugsnag and like, it's going to cost us $800 a month or whatever. So you should raise prices because you're delivering more value than you used to. And so the main thing you have to do is make the case. You got to make the case. When you don't make the case, it goes disastrously. And I've done that before. I'm just like, oh, prices are increasing next week and people freak out. Right. So you got to like be like, look at over the past years, it's been three, four years since last price increase. Look at all the stuff we've added this new module and this thing and that thing, right? Then you lay out the future. This is what's coming. Look at it. We're going to have AI autoresponder. We're going have all the goodies and that stuff's coming, right? And you can give them a little bit of, depending on what's going on in the world, a little inflation. We've all been hit by inflation, right? You make the case. And it goes fine. Like, I mean, we have like,, 400 something customers, whatever it is. I got one mad email and they weren't even mad about the price increase. It was like, you know, it just kicked them off into like writing a mad email. Fine. So one mad email from a very small customer. Like three or four. Oh, the other main thing is you want to give everybody an out. Always give them an out. So at the end of your email, you say, hey, I know you weren't expecting this. Maybe you have budget. You already budgeted for the year. Just email us if it's a problem. We'll work it out with you. And, you know, three or four people email me, oh, we already set the budget for this year. Nope, no problem. This year, you just get the old price. You don't even, you know, no pushback. There's no nothing. I auto say, no problem. Keep you at the last year's rate. And that's it. And then it's fine. And now you have 25% more money. --- ### [Offer A Grace Period To Keep Customers](https://share.snipd.com/snip/a926f13f-457e-4ad9-b250-f3f9679f135b) 🎧 15:58 - 16:53 (00:55) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/87a22451-2a53-4b29-a45c-953b21c987e5" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Give existing customers an easy exemption or grace to avoid resentment and churn. - Ian told customers who already budgeted they could email and keep last year's rate for a year to smooth the transition. #### 💬 Quote > At the end of your email, you say, hey, I know you weren't expecting this. Maybe you have budget. Email us if it's a problem. We'll work it out with you. > — Ian Landsman Ian Landsman on handling customer pushback during price increases #### 📚 Transcript **Ian Landsman:** And it goes fine. Like, I mean, we have like,, 400 something customers, whatever it is. I got one mad email and they weren't even mad about the price increase. It was like, you know, it just kicked them off into like writing a mad email. Fine. So one mad email from a very small customer. Like three or four. Oh, the other main thing is you want to give everybody an out. Always give them an out. So at the end of your email, you say, hey, I know you weren't expecting this. Maybe you have budget. You already budgeted for the year. Just email us if it's a problem. We'll work it out with you. And, you know, three or four people email me, oh, we already set the budget for this year. Nope, no problem. This year, you just get the old price. You don't even, you know, no pushback. There's no nothing. I auto say, no problem. Keep you at the last year's rate. And that's it. And then it's fine. And now you have 25% more money. --- ### [B2B Customers Are Less Price Sensitive Than You Think](https://share.snipd.com/snip/2c10d6c6-7874-4069-88af-11932301eee2) 🎧 18:17 - 20:17 (02:00) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/31d96216-cefa-4f59-8551-3c683ee5ac60" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - B2B pricing tolerances differ greatly because buyers compare price to payroll and switching pain. - Ian notes HelpSpot customers paying thousands see modest hikes as immaterial compared to support staff costs and migration effort. #### 💬 Quote > Oh you're paying 3 500 a year in HelpSpot for you know 2.5 million in customer support salaries like well is three or 400 more dollars 500 more dollars 800 more dollars, is that what puts you over the edge? > — Ian Landsman Ian Landsman on why B2B customers tolerate modest price increases #### 📚 Transcript **Ian Landsman:** Obviously, there's all the like hassle of moving. So there's the lock-in. We love the lock-in. This is, of course a little bit easier with a b2b app than a b2c app um it's also just more direct value right oh you're paying 3 500 a year in help spot for you know 2.5 million in customer support salaries like well is three or 400 more dollars 500 more dollars 800 more dollars, is that what puts you over the edge? Probably not. So. Yeah. **Aaron Francis:** So when did we execute this? It **Ian Landsman:** was last Monday. You know, didn't hide it. I was ready to do it on Friday. I was delayed. I wanted to do it like Thursday and then whatever. It busy. Didn't get everything kind of in place till Friday. And now it's like, I don't want to do it on Friday because I don't want it to be like, oh, we put it out Friday at 4 p.m. Like everybody puts out the bad news. Ship it out Monday morning. That's what we did. It **Aaron Francis:** went great. And you just got 25% more money. I **Ian Landsman:** got 25% more money. **Aaron Francis:** Oh, that is amazing. That's what I'm **Ian Landsman:** talking about. More money. That's freaking dream, man. I mean, listen, it's not all just like profit because there's like, I mean, I mean, in a sense it is all profit. But I know our costs are going up too. It's like, you know, Taylor Otwell and Eric Barnes used to work for me for less money than anybody who works here now combined. **Aaron Francis:** Yeah. **Ian Landsman:** Right. So like, you know, the costs are not the same as they were, you know, 10 years ago. I know two, three years from now, the costs are going to be more. Right. So like Monday to Tuesday, you got a you got a big bump. Right. We got a bump. So, you know, a little flexibility. That's we're doing with AI tooling and help spot. You know, who knows how that's going to go? We're going to have a whole bunch of expenses. One of the things we've never had before is like metered expenses, right? Like up until now, it's like, well, it's all marginal increases. Like every unit sold is just profit basically, right? Whereas like now it won't be that. --- ### [Use Simple Honest Pricing To Avoid Confusion](https://share.snipd.com/snip/f90395a9-5a49-4747-9a6c-31a266bcb2cb) 🎧 28:24 - 29:56 (01:32) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/964b7dfd-85b7-4ca6-a466-52a75bf724eb" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Simplify public pricing and avoid one-year loss-leader renewal pricing. - Aaron removed his $99 first-year then $69 renewal pattern and set a single $99/year price to avoid confusion and revenue loss. #### 💬 Quote > That was just dumb. I don't get the benefit of the $69 sticker price because everybody looks at it and they see $99. > — Aaron Francis Aaron Francis on simplifying Solo's pricing #### 📚 Transcript **Aaron Francis:** so the first thing i did which is um similar to what we were just talking about if slightly different is i raised the price on all new people but not not the first year price the renewal price because for some reason i set it at 99 first99 first year, $69 year after that. Insane. That was just dumb. That makes sense. I don't get the benefit of the $69 sticker price because everybody looks at it and they see $99. So they think, oh, it's $99 a year. So I don't get that social credit. And then I get fewer dollars the next year. So what the hell was **Ian Landsman:** I doing? Your love you most and are never leaving are now paying less, which makes no sense. Makes no sense. So that's a good fix. You're at two groups already. See, this is how you end up with multiple groups. You now have two groups. Yes. **Aaron Francis:** Yes. So and I did all this through Stripe. So we'll see how goes. is where you were talking about from your own known pain here. see goes. Okay. So **Ian Landsman:** now it's **Aaron Francis:** just a year period. $99 a year. Get over it. That's less than something that doesn't cost very much. People are not that **Ian Landsman:** price sensitive. This is a huge thing you have to understand out there, you people, not just Aaron. People are not price sensitive on that level. It's like $69, $99. It's all the same thing. It doesn't matter. $99 is a great price. I $99. $99. **Aaron Francis:** So it's $99 a year. So that's good already. I'm already seeing, I mean, we don't have enough to be like statistically significant, but purchases **Ian Landsman:** are still rolling through. So it's fine. Didn't kill. Yeah. I can't imagine. Nobody even understood they were paying 69. --- ### [Sell Teams With Graduated Pricing And Claim Links](https://share.snipd.com/snip/d5f07b25-0b79-40aa-85a2-0ac4f6061b59) 🎧 30:14 - 32:43 (02:28) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/10fe09e8-dc04-4b58-9201-5b7612f4f12a" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Offer team plans with graduated seat pricing and self-serve claim links to reduce friction. - Aaron built tiers (99→89→79→69) and prepaid claim links so managers buy seats without maintaining rosters or immediate billing for unclaimed seats. #### 💬 Quote > You can buy prepaid seats and then you can hand out a link a claim link to all of your employees so you don't need a registry you don't need to maintain some roster. > — Aaron Francis Aaron Francis on Solo's team purchasing flow #### 📚 Transcript **Aaron Francis:** Okay. Yes. So. I'm very happy. **Ian Landsman:** Very excited. **Aaron Francis:** One is like, so it's centrally managed. So the manager could sign up and do all of that that's a that's a benefit the other benefit is as you move up the tranches get cheaper so like the first three and it's like it's like tax brackets like the next one is cheaper it doesn't make your previous ones cheaper so the licenses one through three are sticker price 99 and then like four through is 89 and then like 11 through 50 is 79 and then 51 up is 69 so the more you buy the more you save something i just came up with there great genius idea so liking that what i'm but i'm what I'm really liking is the means by which the manager controls the licensing pool so you can you have two options you can sign up and just buy 50 seats and then you can hand out a link a claim link to all of your employees so you don't need a registry you don't need to maintain some roster because the manager is like, okay, I'll go freaking buy this thing. And then here's the link I never want to hear from you developers again. You know, it's like. **Ian Landsman:** It's always annoying to have some management central. You're inviting people and removing people. The **Aaron Francis:** only time that makes sense is if you're SSO'd into like one of these central management platforms. And it's like, I keep my employee roster in a singular place and I need all of you other apps to respect that. That's not what's going on here. I'm not going to make them log in to Solo to do this. So you can buy prepaid seats. You could also just buy a seat to just like start your subscription. Just buy a seat. then you can set a limit on, um, auto growing your pool. So you can buy a seat, get your claim link and say, all right, uh, up to 50 people, I will pay for up to 50 people, but not until, not until they come in and claim their license. **Ian Landsman:** Right. Okay. And **Aaron Francis:** then the pool, like from the point of view of the employee, they just go in and claim a license. And then the pool auto expands up to the size and it like does the stripe proration and everything. So everybody's renewal date ends up the same, which is nice for next year's billing. But that allows the manager to hold off. --- ### [Pair Automated Onboarding With Personal Outreach](https://share.snipd.com/snip/e686ae50-9664-4d6c-aa2b-b39993dc1a5d) 🎧 43:11 - 44:56 (01:45) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/533fbd9e-12bd-4b64-91dd-68874d3c0c3c" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Combine automated email onboarding with at least one personal outreach to boost trial engagement. - Ian shares Jamie's manual outreach gets ~50% reply rate versus almost zero from automated emails. #### 💬 Quote > Jamie actually is personally reaching out to every trial with like, Hey, really, how's it going? And there's like a 50% response rate to that. > — Ian Landsman Ian Landsman on trial onboarding effectiveness #### 📚 Transcript **Aaron Francis:** By the way, turn on the MCP. Here's how you can do coordination. By the way, you can save prompt templates. And so that'll like get people into using it. So that's one thing that like is a best practice that we have not been doing. I that. I got a note on that. Give me a note. For end. **Ian Landsman:** Oh, you want the note now? Okay. **Aaron Francis:** Is the note on this email flow? It is. It is. **Ian Landsman:** Give it to me now. All right. So we've obviously had that kind of email flow, blah, blah, blah. Nobody ever replies to them. Sure. And are they useful? Are they not? I don't know. Have I micro-optimized it no i haven't so we're actually i actually right now we i just like a month ago turned those off completely because i want to redo it and like rethink it a little bit so i think it's fine to have those but a thing we've added like in the last three months is jamie actually is personally reaching out to every trial with like, Hey, really, how's it going? And there's like a 50% response rate to that. So the automatic emails literally never got any responses. And the personal email from the actual human gets like 50% responses. **Aaron Francis:** Personal, personal, or like auto sent personal, personal, personal, personal, she physically **Ian Landsman:** sends each one, which probably first of all, helps with deliverability a little bit. So there's probably that's a little bit of the factor. But also, I just think it's like very clearly just, I mean, you could probably fake this to be very close and people couldn't tell. We are not doing that right now. She's just sending a normal email as a normal person saying, hey, what's up? If you anything, let me know. It's like, you know, a couple sentences and tons of people write back. it could be something for Sam, you know, maybe, again, you're more B2C here, at least right at this stage. So I don't know time-wise how realistic that is, but maybe even like spot do that and just see how much people reply. --- ### [Big Acquisition Goals Steer Product Tradeoffs](https://share.snipd.com/snip/2d71af90-2da1-481a-98d0-c66d9943f239) 🎧 49:12 - 51:11 (01:58) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/8ca2927a-5507-41a2-999e-5b532cc6ada7" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - A bold acquisition goal clarifies product strategy and trade-offs. - Aaron's vision to be acquired by OpenAI or Cloudflare within a year influenced choices like paid vs free user growth and team features direction. #### 💬 Quote > I want to be purchased by OpenAI or Cloudflare, ideally in the next one year. > — Aaron Francis Aaron Francis on Solo's acquisition-oriented vision #### 📚 Transcript **Aaron Francis:** I want to be purchased by OpenAI or Cloudflare, ideally in the next one year. That would be best. We'll see. **Ian Landsman:** You're really setting yourself up here. That is **Aaron Francis:** the only way to do it. You've got big audacious goals true **Ian Landsman:** this is the ai world people do get acquired you're in the cutting edge thing that's more likely to be just scooped up potentially **Aaron Francis:** we haven't had a bible corner in a minute but let me tell you where there is a lack of vision the people perish ian you gotta **Ian Landsman:** have a vision quote yeah? **Aaron Francis:** Yeah. Okay, I like that one. Let's see. I have, my references are so bad. It seems unlikely to be an exact quote, but. Let's see. Without vision, the people perish. Boom. Proverbs **Ian Landsman:** 29, 18. There we go. It was pretty much an exact quote. Nice job. But he that **Aaron Francis:** keepeth the law, happy is he we **Ian Landsman:** got we got a little people need to hear that one **Aaron Francis:** yeah we got a little law enforcement there at the end so you know problem **Ian Landsman:** problem with that **Aaron Francis:** they love the law um so i gotta have a vision and that's my vision get bought get rich start digging that's the vision it's **Ian Landsman:** an okay vision i think that there's a i but see probably i don't i don't personally love that vision because i feel like you're in a conflicted spot with that vision because i think what you two different paths like i want to get acquired in a year i think you should be doing very different things i wouldn't be charging anybody money for anything it'd be totally free you're right yeah it should be totally free and just get as much users as you can keep that chart going up up up up which is gonna be much harder if you're charging money. Right. So it's just like, oh, every month the users are doubling. That's great. Like in free, you have a shot at that. Like paid is going to be very hard. So yeah, **Aaron Francis:** I **Ian Landsman:** do think you're, that's a little bit like tricky there. But **Aaron Francis:** I like what you're from a boot jobber. Yeah. **Ian Landsman:** Boot jobber angle. I like the charging people money, of course. I think that's the way. I like the team plans. It's all good stuff. --- ### [Free Growth Versus Paid Revenue Changes Exit Paths](https://share.snipd.com/snip/3658cfb8-36bd-49ed-92f6-2c159b1a4524) 🎧 50:39 - 51:11 (00:32) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/d4a175de-f0fb-4e5a-84ed-84fa447b89fa" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Charging users and aiming for acquisition require different growth strategies. - Ian argues free user growth favors acquisition while monetization prioritizes sustainable revenue and team features. #### 💬 Quote > If you want to get acquired in a year I think you should be doing very different things. I wouldn't be charging anybody money for anything it'd be totally free. > — Ian Landsman Ian Landsman on tradeoffs between free growth and paid revenue #### 📚 Transcript **Ian Landsman:** right yeah it should be totally free and just get as much users as you can keep that chart going up up up up which is gonna be be harder if you're charging money. Right. So it's just like, oh, every month the users are doubling. That's great. Like in free, you have a shot at that. Like paid is going to be very hard. So yeah, **Aaron Francis:** I **Ian Landsman:** do think you're, that's a little bit like tricky there. But **Aaron Francis:** I like what you're doing a boot jobber. Yeah. **Ian Landsman:** Boot jobber angle. I like the charging people money, of course. I think that's the way. I like the team plans. It's all good stuff. --- ### [Management Controls On AI Usage Are A Team Seller](https://share.snipd.com/snip/65890e8a-e161-4728-8042-9e7974fd8bb1) 🎧 53:20 - 56:21 (03:01) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/6a9b9697-d9d1-44a9-aa8a-d716b36303c0" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Team features that control AI usage, costs, and data policies are strong enterprise hooks. - Ian suggests centralized token-usage dashboards, spend alerts, and policy enforcement across OpenAI/Anthropic to sell teams beyond billing convenience. #### 💬 Quote > You could have alerts, you could have all the stuff, all the money, you can check that in one spot I think you could have things like settings for like making sure like you're never allowing training. > — Ian Landsman Ian Landsman on product features that appeal to teams #### 📚 Transcript **Aaron Francis:** yeah i could i could pass a flag and I already do some introspection on their cloud.json at the root level. Yeah, so stuff like that. I'm feeding **Ian Landsman:** that on everybody. Now we can make sure everybody's in the right state so OpenAI can't train on your data, and that solo's enforcing that across all the different types of AI **Aaron Francis:** use. interesting. I **Ian Landsman:** don't know. I think stuff like that where it's really management-y. You know what I mean? **Aaron Francis:** Yeah, that's interesting. I think I could totally get there. **Ian Landsman:** Yeah. I don't think it seems too bad. There's probably other stuff along those lines, but like people are scared of spending too much money on the AI, right? And they're scared of like the data getting leaked. So like things where Solo can help with those things, I think it's kind of interesting. And also stuff I haven't seen. Well, I mean, obviously the lab ones don't really do it. They only do it for their own, right? They don't do it across. So, I don't know. There's something **Aaron Francis:** there. Yeah, that's interesting. Because if you're not using Open Router, and you're like, hey, team, we're on, you know, for Claude, we're on teams for codex or whatever which is exactly what i do yep then you're hosed you don't get a centralized right dashboard hmm that's interesting and **Ian Landsman:** i think your market is probably not **Aaron Francis:** so much **Ian Landsman:** that we **Aaron Francis:** use open router and are like big enterprisey **Ian Landsman:** right type of **Aaron Francis:** nobody wants to pay by token i mean right so **Ian Landsman:** yeah so you want to be able to track still though like who's going over and like again i can do this in each individual dashboard but like i have to go around and check all these things and like i don't know i'm sure there's even other stuff you could do from there right you could expose who's not using enough tokens. Maybe there's excess capacity and people want to utilize that somehow, whatever, blah, blah, blah. I don't know. You could enforce other types of things. We could have logging of various sorts potentially, or injecting corporate rules at the start of every session, making sure Claude files contain certain rules, no matter what. **Aaron Francis:** Well, well, well, well, well. This is interesting, isn't it? Yeah. **Ian Landsman:** I don't know. Again, that's all stuff that has to be really marketed, so it's not so discoverable, right? It's like you built this whole server side thing that does a bunch of stuff, and now you've got to figure out how to get people to know about it. But I do think there's something there.'s something there okay **Aaron Francis:** hmm well the door is open now i have teams so yeah i can start to figure out one right now it's right now it's merely a billing convenience but i do like the idea of getting it to an actual like **Ian Landsman:** team yeah i think if you could add features to it, it's like very intriguing on like people buying the team plan to begin with for like a reason beyond just like the billing convenience. And then that gives you more pricing power. Like if some of those things are really good and awesome, people it. --- ### [Fable 5 Takedown Felt Like Losing A Superpower](https://share.snipd.com/snip/d2652a9c-9028-4c66-8a13-85debc01129c) 🎧 56:51 - 58:16 (01:24) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/4e2303b3-bef4-4e5f-ad36-4b222c94181b" 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 and Aaron reacted strongly to Anthropic's Fable 5 takedown and felt its absence immediately. - Ian described coding with Fable 4.8 as like working with one hand tied and praised Fable 5's helpful UI flow around unfinished Stripe Connect setups. #### 💬 Quote > This is the worst 12D chess I've ever seen from any CEO in all of history. The 12D chess? Yes, my goodness. > — Aaron Francis Aaron Francis reacting to Fable 5 shutdown #### 📚 Transcript **Ian Landsman:** Did you see what they did to Fable 5? Did you see? **Aaron Francis:** They killed it. They **Ian Landsman:** murdered my boy. They killed it. It's dead. love 5. Let me tell you. The rest of the weekend i was working in 4.8 with 5.5 it's like they're both so bad like these are freaking it's like working one hand tied behind your back it's terrible i was just this morning i went into something that fable built and it was like uh when so an outro you're gonna be able to connect uh you know the stripe connect thing so that people can pay for sponsorships and the money goes right to the person's account, not to me, so I don't have to deal with the money. Fine. So there's like a connection flow to connect you up. And like Fable, unprompted, had just done this beautiful little in-between state of like, you started your connection process, you didn't finish it. And it's got the right button. It's got a little message. Yes. It's like when you come back to the page of the sponsors, it's hey, you started this, but you didn't finish it. Like, you know, click here to finish it. Like, it just did all that. It just knew to do it. It did it. And it looked nice. It was done. 4.8 is not doing that. 5.5 is not doing it either. And you brought **Aaron Francis:** the kindergartners in to finish **Ian Landsman:** the job. So bad. I don't want to go back to hand coding, but it feels like I am. It feels like I'm hand coding again. It's like, **Aaron Francis:** boy, how quickly we adapt. **Ian Landsman:** Isn't that crazy? It's crazy. It's like you used it for a day. And it's like, boy, it's so much better. --- ### [AI Releases Can Prompt Rapid Political Pushback](https://share.snipd.com/snip/befa1337-bb56-40e8-a778-b2d862a0c2e5) 🎧 59:00 - 01:02:28 (03:27) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/68fba8d1-1fb0-491b-8a64-234880e6ea4a" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Cutting-edge models trigger political and regulatory reactions that shape access quickly. - Ian and Aaron discuss Fable's removal, U.S. government intervention, and the likely short-term vs long-term availability tradeoffs across providers. #### 💬 Quote > It's over. Because no model, like, going forward, I can't imagine maybe the next, the very next micro generation is, like, less powerful than Fable. > — Aaron Francis Aaron Francis on the significance of Fable 5's removal #### 📚 Transcript **Aaron Francis:** It's over. Because no model, like, going forward, I can't imagine maybe the next, the very next micro generation is, like, less powerful than Fable. But after that, this is it. We don't go backwards. No, we're not. I mean, this is **Ian Landsman:** why I'm going to be very interested to see what they do with open AI. Because if you're saying, listen, we are at nuclear weapons level, right? This is nuclear weapons. You can't have a nuclear weapon in your house. That's going to be true of this class of model and beyond. Then let's see it everywhere, right? Let's see the open AI. You know, the next open AI one's going to be in the ballpark of as good, right? It's very unlikely it's going to be that Anthropic has some magic juice that's like, they're so much better, right? They're five years ahead. I don't think they're five years ahead. I think they're a few months ahead. So, I don't know. We'll see if it's politics or if it's legit. If it's legit, I would like to see some actual laws. I know we don't do that in this country anymore, but I would like to see some laws that are like, this is, we're going to put some guidelines around this in a way everybody understands and we're all agreeing to. I got to **Aaron Francis:** say, this is the worst 12D chess I've ever seen from any CEO in all of history. The 12D chess? Yes, my goodness. **Ian Landsman:** What Make it seem like I'm building nuclear weapons and giving them to every rando yeah the **Aaron Francis:** it's like i'm building a nuclear weapon this is too powerful to release um i can't give it to the u.s government i won't work with the u.s government if anyone builds it everyone dies announcing fable five like what did you expect was going to happen? Like, this is literally what you were asking for. You wanted regulation, and then they hit you with this pseudo-regulation, and you were like, oops, not like that, you know? I don't know, man. And, you know, on the flip side, I'm sure you've read the Paul Graham either tweet or essay about if Sam Altman were, you know, parachuted onto an island of cannibals, you'd come back in six months and he would be their ruler. Like, have you read that from Paul Graham? That **Ian Landsman:** sounds kind of awesome. I have to go read that now. So on the **Aaron Francis:** other side, you've got the actual 12D chess master who is Sam Altman. And you have to wonder now what happens to GPT 5.6? Like, because he's playing the game. And meanwhile, Dario's like, I hate that I'm building this civilization ending tool. $200 a month. And you're like, why? Come on, dude. We've talked **Ian Landsman:** about that before. I don't know. I feel like it's such a powerful tool in a positive light that you don't need the negative aspect to sell it. I agree. It sells itself. You have something that literally sells itself, which happens very rarely. If you can just get anybody to taste it for a second, it just sells itself. It's so much better than what you were doing before. Like, just keep giving out tastes. Like, so, yeah, I don't know. They've definitely played that, I guess, incorrectly. I mean, we'll see. But probably they played it incorrectly. But it also is like, who is really being hurt, I think is an interesting question. Me? Oh, well, that's for sure. But, you know, all these Chinese models, they're just catching up all the time, every day, every minute. --- ### [Make Sponsorships Optional And Marketplace Ready](https://share.snipd.com/snip/407f2259-20f7-40bd-9c8f-a45a9b112d09) 🎧 01:09:59 - 01:14:29 (04:29) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/52c49913-5c98-438c-a017-58a22d4c5858" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Build sponsorship tooling with optional Stripe connect and a marketplace to attract both podcasters and advertisers. - Ian built Outro to let hosts optionally connect Stripe, manage deals, and later list shows with basic metrics for advertisers. #### 💬 Quote > You can just manage deals through there if you want to without billing. You can use it as like a back office without taking the payment. > — Ian Landsman Ian Landsman on Outro's sponsorship model #### 📚 Transcript **Ian Landsman:** But it's very sad because Fable 5, I know I'd be done already. **Aaron Francis:** So what's the model of the sponsorship? So I connect my Stripe as a podcast host. **Ian Landsman:** Optionally. You don't have to. Okay. You can just manage deals through there if you want to without billing. **Aaron Francis:** Oh, I can use it as like a back office without taking **Ian Landsman:** the payment. Right. Smart. Okay. Because I know big shows are not going to ever use this for payments, right? Like Bill Simmons, if he uses this, is not going to do his payments through this thing, right? He's going to have some big **Aaron Francis:** department. You're going to do an for $5 million for three episodes. Ah, damn it. So then can I like, is there like yet a marketplace or a public listing of these shows except sponsors? **Ian Landsman:** No, but it's there. It's ready. It could do it, but it's not doing it yet. Because I figured **Aaron Francis:** not what's the point **Ian Landsman:** of doing it yet. There's no point doing it yet. Nobody even uses it. But yes, you'll be able to do that. We already had somebody ask about that. Bento was asking about that. So that's in the works and i think that's how you sell the **Aaron Francis:** dream to the podcasters yes **Ian Landsman:** you say you'll be listed on this on **Aaron Francis:** this page where advertisers come to spend money and every podcaster is going to be like i want money i that's how how you get, especially if you tie back in some sort of metrics. So you know, presumably you know the podcast feed, and then you could, like, offer OAuth to the big five players, know, Transistor, whatever, whatever, and pull in their stats. And then advertisers can say, like, oh, this podcast gets this many listens. They do episodes this often and they're asking this price yeah that's like that's some that's some transparency that i don't think exists out there that is interesting **Ian Landsman:** i wonder i i don't know if that level of transparency is even good for the podcasters but i'd like where your mind's at in general of like uh there's also like a lot of weirdness obviously nowadays with like well there's the audio listeners but then there's youtube right then there's shorts but then there's like seven places you actually need to get data from I **Aaron Francis:** wonder if PodScan has it all already that data I don't know if **Ian Landsman:** they have that exact data maybe they wouldn't have though estimate but I don't know how they get the listeners like he does estimate that I don't know how he does it because he doesn't have the actual data I don't think well maybe that those are public endpoints like maybe the apple podcast endpoint to get those stats is public i guess maybe it is um so yes but i think even like phase one of it just being like hey here's marketplace some filtering on types of podcasts maybe that podcasters have a place to put their metrics in. Yeah, that could be like a phase one. I think there's even like a bigger world of like big, big sponsors just dump a pile of money on us and we distribute the money out in a logical way, right? So I think there's like a bunch of options there, but that's all like phase two, three type stuff to me. But I do think the idea of having a marketplace pretty early, I don't know if it'll be V1, but pretty early to like at least have the basic, like here's a list of all the podcasts and the platform and yeah, like tags for what their topics you know what their general topic area is and some basic stats and whatever blah blah um yeah i like that so it's there me and fable had worked that part out we had made sure that everything we were building was like prepared for that and so we're good to go on doing a marketplace um once we have some shows besides token town and mostly which the next show is coming july **Aaron Francis:** 8th i believe is when you have to onboard someone else i think **Ian Landsman:** it's gonna work i think i think it's possible this week off for me in the middle is a little bit annoying but i still have a week when i get back so you knew that when i knew it i knew it so i think we'll get somebody in there i want to get sponsors done which it's almost done and it's pretty complicated thing so it's almost done and then uh i don't know i wouldn't mind having the mailbag but i don't think i need the mailbag to get somebody else in there so i think we can get somebody else in before the mailbag so yeah, I think we're almost there. Um, you know, once you let that person in, they're going to feedback and they want things. Boy, don't I know it. --- Created with [Snipd](https://www.snipd.com) | Highlight & Take Notes from Podcasts # Snips updated after 2026-04-05T10:16:17 ### [Raise Prices With A Clear Case And An Out](https://share.snipd.com/snip/6dd790ca-80f0-457d-b40e-02132f12310e) 🎧 14:21 - 16:53 (02:31) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/fa97a3d8-7add-4b03-a842-26f797023318" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Raise prices on existing customers when your product delivers more value and costs rise. - Ian increased HelpSpot ~25% with a clear email explaining added features, future roadmap, and offered an easy opt-out to avoid churn. #### 💬 Quote > You got to make the case. When you don't make the case, it goes disastrously. > — Ian Landsman Ian Landsman on how to raise prices with communication #### 📚 Transcript **Aaron Francis:** All **Ian Landsman:** right. This week, we raised prices on HelpSpot. And I thought it'd be just a fun little business topic. We haven't really done a needy business topic like this in a while. Like, should you raise prices? How you raise prices? And the biggest thing to me, I just wanted to bring this up because I know so many software developers, founders, whatever, the whole thing, who never raise prices on their existing customers. And to me, it's like a humongous, gigantic error of mega proportions. So I just want to bring this up. You can raise prices on your existing customers. You should raise prices on existing customers. Nobody likes it when you do, of course, but like I've talked about this on here before, Bugsnag is still charging us $30 from 15 years ago. We started using Bugsnag. I can never leave Bugsnag. Century sounds great, but I can't leave Bugsnag because we literally put millions of events in Bugsnag and like, it's going to cost us $800 a month or whatever. So you should raise prices because you're delivering more value than you used to. And so the main thing you have to do is make the case. You got to make the case. When you don't make the case, it goes disastrously. And I've done that before. I'm just like, oh, prices are increasing next week and people freak out. Right. So you got to like be like, look at over the past years, it's been three, four years since last price increase. Look at all the stuff we've added this new module and this thing and that thing, right? Then you lay out the future. This is what's coming. Look at it. We're going to have AI autoresponder. We're going have all the goodies and that stuff's coming, right? And you can give them a little bit of, depending on what's going on in the world, a little inflation. We've all been hit by inflation, right? You make the case. And it goes fine. Like, I mean, we have like,, 400 something customers, whatever it is. I got one mad email and they weren't even mad about the price increase. It was like, you know, it just kicked them off into like writing a mad email. Fine. So one mad email from a very small customer. Like three or four. Oh, the other main thing is you want to give everybody an out. Always give them an out. So at the end of your email, you say, hey, I know you weren't expecting this. Maybe you have budget. You already budgeted for the year. Just email us if it's a problem. We'll work it out with you. And, you know, three or four people email me, oh, we already set the budget for this year. Nope, no problem. This year, you just get the old price. You don't even, you know, no pushback. There's no nothing. I auto say, no problem. Keep you at the last year's rate. And that's it. And then it's fine. And now you have 25% more money. --- ### [Offer A Grace Period To Keep Customers](https://share.snipd.com/snip/a926f13f-457e-4ad9-b250-f3f9679f135b) 🎧 15:58 - 16:53 (00:55) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/87a22451-2a53-4b29-a45c-953b21c987e5" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Give existing customers an easy exemption or grace to avoid resentment and churn. - Ian told customers who already budgeted they could email and keep last year's rate for a year to smooth the transition. #### 💬 Quote > At the end of your email, you say, hey, I know you weren't expecting this. Maybe you have budget. Email us if it's a problem. We'll work it out with you. > — Ian Landsman Ian Landsman on handling customer pushback during price increases #### 📚 Transcript **Ian Landsman:** And it goes fine. Like, I mean, we have like,, 400 something customers, whatever it is. I got one mad email and they weren't even mad about the price increase. It was like, you know, it just kicked them off into like writing a mad email. Fine. So one mad email from a very small customer. Like three or four. Oh, the other main thing is you want to give everybody an out. Always give them an out. So at the end of your email, you say, hey, I know you weren't expecting this. Maybe you have budget. You already budgeted for the year. Just email us if it's a problem. We'll work it out with you. And, you know, three or four people email me, oh, we already set the budget for this year. Nope, no problem. This year, you just get the old price. You don't even, you know, no pushback. There's no nothing. I auto say, no problem. Keep you at the last year's rate. And that's it. And then it's fine. And now you have 25% more money. --- ### [B2B Customers Are Less Price Sensitive Than You Think](https://share.snipd.com/snip/2c10d6c6-7874-4069-88af-11932301eee2) 🎧 18:17 - 20:17 (02:00) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/31d96216-cefa-4f59-8551-3c683ee5ac60" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - B2B pricing tolerances differ greatly because buyers compare price to payroll and switching pain. - Ian notes HelpSpot customers paying thousands see modest hikes as immaterial compared to support staff costs and migration effort. #### 💬 Quote > Oh you're paying 3 500 a year in HelpSpot for you know 2.5 million in customer support salaries like well is three or 400 more dollars 500 more dollars 800 more dollars, is that what puts you over the edge? > — Ian Landsman Ian Landsman on why B2B customers tolerate modest price increases #### 📚 Transcript **Ian Landsman:** Obviously, there's all the like hassle of moving. So there's the lock-in. We love the lock-in. This is, of course a little bit easier with a b2b app than a b2c app um it's also just more direct value right oh you're paying 3 500 a year in help spot for you know 2.5 million in customer support salaries like well is three or 400 more dollars 500 more dollars 800 more dollars, is that what puts you over the edge? Probably not. So. Yeah. **Aaron Francis:** So when did we execute this? It **Ian Landsman:** was last Monday. You know, didn't hide it. I was ready to do it on Friday. I was delayed. I wanted to do it like Thursday and then whatever. It busy. Didn't get everything kind of in place till Friday. And now it's like, I don't want to do it on Friday because I don't want it to be like, oh, we put it out Friday at 4 p.m. Like everybody puts out the bad news. Ship it out Monday morning. That's what we did. It **Aaron Francis:** went great. And you just got 25% more money. I **Ian Landsman:** got 25% more money. **Aaron Francis:** Oh, that is amazing. That's what I'm **Ian Landsman:** talking about. More money. That's freaking dream, man. I mean, listen, it's not all just like profit because there's like, I mean, I mean, in a sense it is all profit. But I know our costs are going up too. It's like, you know, Taylor Otwell and Eric Barnes used to work for me for less money than anybody who works here now combined. **Aaron Francis:** Yeah. **Ian Landsman:** Right. So like, you know, the costs are not the same as they were, you know, 10 years ago. I know two, three years from now, the costs are going to be more. Right. So like Monday to Tuesday, you got a you got a big bump. Right. We got a bump. So, you know, a little flexibility. That's we're doing with AI tooling and help spot. You know, who knows how that's going to go? We're going to have a whole bunch of expenses. One of the things we've never had before is like metered expenses, right? Like up until now, it's like, well, it's all marginal increases. Like every unit sold is just profit basically, right? Whereas like now it won't be that. --- ### [Use Simple Honest Pricing To Avoid Confusion](https://share.snipd.com/snip/f90395a9-5a49-4747-9a6c-31a266bcb2cb) 🎧 28:24 - 29:56 (01:32) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/964b7dfd-85b7-4ca6-a466-52a75bf724eb" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Simplify public pricing and avoid one-year loss-leader renewal pricing. - Aaron removed his $99 first-year then $69 renewal pattern and set a single $99/year price to avoid confusion and revenue loss. #### 💬 Quote > That was just dumb. I don't get the benefit of the $69 sticker price because everybody looks at it and they see $99. > — Aaron Francis Aaron Francis on simplifying Solo's pricing #### 📚 Transcript **Aaron Francis:** so the first thing i did which is um similar to what we were just talking about if slightly different is i raised the price on all new people but not not the first year price the renewal price because for some reason i set it at 99 first99 first year, $69 year after that. Insane. That was just dumb. That makes sense. I don't get the benefit of the $69 sticker price because everybody looks at it and they see $99. So they think, oh, it's $99 a year. So I don't get that social credit. And then I get fewer dollars the next year. So what the hell was **Ian Landsman:** I doing? Your love you most and are never leaving are now paying less, which makes no sense. Makes no sense. So that's a good fix. You're at two groups already. See, this is how you end up with multiple groups. You now have two groups. Yes. **Aaron Francis:** Yes. So and I did all this through Stripe. So we'll see how goes. is where you were talking about from your own known pain here. see goes. Okay. So **Ian Landsman:** now it's **Aaron Francis:** just a year period. $99 a year. Get over it. That's less than something that doesn't cost very much. People are not that **Ian Landsman:** price sensitive. This is a huge thing you have to understand out there, you people, not just Aaron. People are not price sensitive on that level. It's like $69, $99. It's all the same thing. It doesn't matter. $99 is a great price. I $99. $99. **Aaron Francis:** So it's $99 a year. So that's good already. I'm already seeing, I mean, we don't have enough to be like statistically significant, but purchases **Ian Landsman:** are still rolling through. So it's fine. Didn't kill. Yeah. I can't imagine. Nobody even understood they were paying 69. --- ### [Sell Teams With Graduated Pricing And Claim Links](https://share.snipd.com/snip/d5f07b25-0b79-40aa-85a2-0ac4f6061b59) 🎧 30:14 - 32:43 (02:28) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/10fe09e8-dc04-4b58-9201-5b7612f4f12a" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Offer team plans with graduated seat pricing and self-serve claim links to reduce friction. - Aaron built tiers (99→89→79→69) and prepaid claim links so managers buy seats without maintaining rosters or immediate billing for unclaimed seats. #### 💬 Quote > You can buy prepaid seats and then you can hand out a link a claim link to all of your employees so you don't need a registry you don't need to maintain some roster. > — Aaron Francis Aaron Francis on Solo's team purchasing flow #### 📚 Transcript **Aaron Francis:** Okay. Yes. So. I'm very happy. **Ian Landsman:** Very excited. **Aaron Francis:** One is like, so it's centrally managed. So the manager could sign up and do all of that that's a that's a benefit the other benefit is as you move up the tranches get cheaper so like the first three and it's like it's like tax brackets like the next one is cheaper it doesn't make your previous ones cheaper so the licenses one through three are sticker price 99 and then like four through is 89 and then like 11 through 50 is 79 and then 51 up is 69 so the more you buy the more you save something i just came up with there great genius idea so liking that what i'm but i'm what I'm really liking is the means by which the manager controls the licensing pool so you can you have two options you can sign up and just buy 50 seats and then you can hand out a link a claim link to all of your employees so you don't need a registry you don't need to maintain some roster because the manager is like, okay, I'll go freaking buy this thing. And then here's the link I never want to hear from you developers again. You know, it's like. **Ian Landsman:** It's always annoying to have some management central. You're inviting people and removing people. The **Aaron Francis:** only time that makes sense is if you're SSO'd into like one of these central management platforms. And it's like, I keep my employee roster in a singular place and I need all of you other apps to respect that. That's not what's going on here. I'm not going to make them log in to Solo to do this. So you can buy prepaid seats. You could also just buy a seat to just like start your subscription. Just buy a seat. then you can set a limit on, um, auto growing your pool. So you can buy a seat, get your claim link and say, all right, uh, up to 50 people, I will pay for up to 50 people, but not until, not until they come in and claim their license. **Ian Landsman:** Right. Okay. And **Aaron Francis:** then the pool, like from the point of view of the employee, they just go in and claim a license. And then the pool auto expands up to the size and it like does the stripe proration and everything. So everybody's renewal date ends up the same, which is nice for next year's billing. But that allows the manager to hold off. --- ### [Pair Automated Onboarding With Personal Outreach](https://share.snipd.com/snip/e686ae50-9664-4d6c-aa2b-b39993dc1a5d) 🎧 43:11 - 44:56 (01:45) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/533fbd9e-12bd-4b64-91dd-68874d3c0c3c" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Combine automated email onboarding with at least one personal outreach to boost trial engagement. - Ian shares Jamie's manual outreach gets ~50% reply rate versus almost zero from automated emails. #### 💬 Quote > Jamie actually is personally reaching out to every trial with like, Hey, really, how's it going? And there's like a 50% response rate to that. > — Ian Landsman Ian Landsman on trial onboarding effectiveness #### 📚 Transcript **Aaron Francis:** By the way, turn on the MCP. Here's how you can do coordination. By the way, you can save prompt templates. And so that'll like get people into using it. So that's one thing that like is a best practice that we have not been doing. I that. I got a note on that. Give me a note. For end. **Ian Landsman:** Oh, you want the note now? Okay. **Aaron Francis:** Is the note on this email flow? It is. It is. **Ian Landsman:** Give it to me now. All right. So we've obviously had that kind of email flow, blah, blah, blah. Nobody ever replies to them. Sure. And are they useful? Are they not? I don't know. Have I micro-optimized it no i haven't so we're actually i actually right now we i just like a month ago turned those off completely because i want to redo it and like rethink it a little bit so i think it's fine to have those but a thing we've added like in the last three months is jamie actually is personally reaching out to every trial with like, Hey, really, how's it going? And there's like a 50% response rate to that. So the automatic emails literally never got any responses. And the personal email from the actual human gets like 50% responses. **Aaron Francis:** Personal, personal, or like auto sent personal, personal, personal, personal, she physically **Ian Landsman:** sends each one, which probably first of all, helps with deliverability a little bit. So there's probably that's a little bit of the factor. But also, I just think it's like very clearly just, I mean, you could probably fake this to be very close and people couldn't tell. We are not doing that right now. She's just sending a normal email as a normal person saying, hey, what's up? If you anything, let me know. It's like, you know, a couple sentences and tons of people write back. it could be something for Sam, you know, maybe, again, you're more B2C here, at least right at this stage. So I don't know time-wise how realistic that is, but maybe even like spot do that and just see how much people reply. --- ### [Big Acquisition Goals Steer Product Tradeoffs](https://share.snipd.com/snip/2d71af90-2da1-481a-98d0-c66d9943f239) 🎧 49:12 - 51:11 (01:58) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/8ca2927a-5507-41a2-999e-5b532cc6ada7" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - A bold acquisition goal clarifies product strategy and trade-offs. - Aaron's vision to be acquired by OpenAI or Cloudflare within a year influenced choices like paid vs free user growth and team features direction. #### 💬 Quote > I want to be purchased by OpenAI or Cloudflare, ideally in the next one year. > — Aaron Francis Aaron Francis on Solo's acquisition-oriented vision #### 📚 Transcript **Aaron Francis:** I want to be purchased by OpenAI or Cloudflare, ideally in the next one year. That would be best. We'll see. **Ian Landsman:** You're really setting yourself up here. That is **Aaron Francis:** the only way to do it. You've got big audacious goals true **Ian Landsman:** this is the ai world people do get acquired you're in the cutting edge thing that's more likely to be just scooped up potentially **Aaron Francis:** we haven't had a bible corner in a minute but let me tell you where there is a lack of vision the people perish ian you gotta **Ian Landsman:** have a vision quote yeah? **Aaron Francis:** Yeah. Okay, I like that one. Let's see. I have, my references are so bad. It seems unlikely to be an exact quote, but. Let's see. Without vision, the people perish. Boom. Proverbs **Ian Landsman:** 29, 18. There we go. It was pretty much an exact quote. Nice job. But he that **Aaron Francis:** keepeth the law, happy is he we **Ian Landsman:** got we got a little people need to hear that one **Aaron Francis:** yeah we got a little law enforcement there at the end so you know problem **Ian Landsman:** problem with that **Aaron Francis:** they love the law um so i gotta have a vision and that's my vision get bought get rich start digging that's the vision it's **Ian Landsman:** an okay vision i think that there's a i but see probably i don't i don't personally love that vision because i feel like you're in a conflicted spot with that vision because i think what you two different paths like i want to get acquired in a year i think you should be doing very different things i wouldn't be charging anybody money for anything it'd be totally free you're right yeah it should be totally free and just get as much users as you can keep that chart going up up up up which is gonna be much harder if you're charging money. Right. So it's just like, oh, every month the users are doubling. That's great. Like in free, you have a shot at that. Like paid is going to be very hard. So yeah, **Aaron Francis:** I **Ian Landsman:** do think you're, that's a little bit like tricky there. But **Aaron Francis:** I like what you're from a boot jobber. Yeah. **Ian Landsman:** Boot jobber angle. I like the charging people money, of course. I think that's the way. I like the team plans. It's all good stuff. --- ### [Free Growth Versus Paid Revenue Changes Exit Paths](https://share.snipd.com/snip/3658cfb8-36bd-49ed-92f6-2c159b1a4524) 🎧 50:39 - 51:11 (00:32) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/d4a175de-f0fb-4e5a-84ed-84fa447b89fa" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Charging users and aiming for acquisition require different growth strategies. - Ian argues free user growth favors acquisition while monetization prioritizes sustainable revenue and team features. #### 💬 Quote > If you want to get acquired in a year I think you should be doing very different things. I wouldn't be charging anybody money for anything it'd be totally free. > — Ian Landsman Ian Landsman on tradeoffs between free growth and paid revenue #### 📚 Transcript **Ian Landsman:** right yeah it should be totally free and just get as much users as you can keep that chart going up up up up which is gonna be be harder if you're charging money. Right. So it's just like, oh, every month the users are doubling. That's great. Like in free, you have a shot at that. Like paid is going to be very hard. So yeah, **Aaron Francis:** I **Ian Landsman:** do think you're, that's a little bit like tricky there. But **Aaron Francis:** I like what you're doing a boot jobber. Yeah. **Ian Landsman:** Boot jobber angle. I like the charging people money, of course. I think that's the way. I like the team plans. It's all good stuff. --- ### [Management Controls On AI Usage Are A Team Seller](https://share.snipd.com/snip/65890e8a-e161-4728-8042-9e7974fd8bb1) 🎧 53:20 - 56:21 (03:01) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/6a9b9697-d9d1-44a9-aa8a-d716b36303c0" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Team features that control AI usage, costs, and data policies are strong enterprise hooks. - Ian suggests centralized token-usage dashboards, spend alerts, and policy enforcement across OpenAI/Anthropic to sell teams beyond billing convenience. #### 💬 Quote > You could have alerts, you could have all the stuff, all the money, you can check that in one spot I think you could have things like settings for like making sure like you're never allowing training. > — Ian Landsman Ian Landsman on product features that appeal to teams #### 📚 Transcript **Aaron Francis:** yeah i could i could pass a flag and I already do some introspection on their cloud.json at the root level. Yeah, so stuff like that. I'm feeding **Ian Landsman:** that on everybody. Now we can make sure everybody's in the right state so OpenAI can't train on your data, and that solo's enforcing that across all the different types of AI **Aaron Francis:** use. interesting. I **Ian Landsman:** don't know. I think stuff like that where it's really management-y. You know what I mean? **Aaron Francis:** Yeah, that's interesting. I think I could totally get there. **Ian Landsman:** Yeah. I don't think it seems too bad. There's probably other stuff along those lines, but like people are scared of spending too much money on the AI, right? And they're scared of like the data getting leaked. So like things where Solo can help with those things, I think it's kind of interesting. And also stuff I haven't seen. Well, I mean, obviously the lab ones don't really do it. They only do it for their own, right? They don't do it across. So, I don't know. There's something **Aaron Francis:** there. Yeah, that's interesting. Because if you're not using Open Router, and you're like, hey, team, we're on, you know, for Claude, we're on teams for codex or whatever which is exactly what i do yep then you're hosed you don't get a centralized right dashboard hmm that's interesting and **Ian Landsman:** i think your market is probably not **Aaron Francis:** so much **Ian Landsman:** that we **Aaron Francis:** use open router and are like big enterprisey **Ian Landsman:** right type of **Aaron Francis:** nobody wants to pay by token i mean right so **Ian Landsman:** yeah so you want to be able to track still though like who's going over and like again i can do this in each individual dashboard but like i have to go around and check all these things and like i don't know i'm sure there's even other stuff you could do from there right you could expose who's not using enough tokens. Maybe there's excess capacity and people want to utilize that somehow, whatever, blah, blah, blah. I don't know. You could enforce other types of things. We could have logging of various sorts potentially, or injecting corporate rules at the start of every session, making sure Claude files contain certain rules, no matter what. **Aaron Francis:** Well, well, well, well, well. This is interesting, isn't it? Yeah. **Ian Landsman:** I don't know. Again, that's all stuff that has to be really marketed, so it's not so discoverable, right? It's like you built this whole server side thing that does a bunch of stuff, and now you've got to figure out how to get people to know about it. But I do think there's something there.'s something there okay **Aaron Francis:** hmm well the door is open now i have teams so yeah i can start to figure out one right now it's right now it's merely a billing convenience but i do like the idea of getting it to an actual like **Ian Landsman:** team yeah i think if you could add features to it, it's like very intriguing on like people buying the team plan to begin with for like a reason beyond just like the billing convenience. And then that gives you more pricing power. Like if some of those things are really good and awesome, people it. --- ### [Fable 5 Takedown Felt Like Losing A Superpower](https://share.snipd.com/snip/d2652a9c-9028-4c66-8a13-85debc01129c) 🎧 56:51 - 58:16 (01:24) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/4e2303b3-bef4-4e5f-ad36-4b222c94181b" 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 and Aaron reacted strongly to Anthropic's Fable 5 takedown and felt its absence immediately. - Ian described coding with Fable 4.8 as like working with one hand tied and praised Fable 5's helpful UI flow around unfinished Stripe Connect setups. #### 💬 Quote > This is the worst 12D chess I've ever seen from any CEO in all of history. The 12D chess? Yes, my goodness. > — Aaron Francis Aaron Francis reacting to Fable 5 shutdown #### 📚 Transcript **Ian Landsman:** Did you see what they did to Fable 5? Did you see? **Aaron Francis:** They killed it. They **Ian Landsman:** murdered my boy. They killed it. It's dead. love 5. Let me tell you. The rest of the weekend i was working in 4.8 with 5.5 it's like they're both so bad like these are freaking it's like working one hand tied behind your back it's terrible i was just this morning i went into something that fable built and it was like uh when so an outro you're gonna be able to connect uh you know the stripe connect thing so that people can pay for sponsorships and the money goes right to the person's account, not to me, so I don't have to deal with the money. Fine. So there's like a connection flow to connect you up. And like Fable, unprompted, had just done this beautiful little in-between state of like, you started your connection process, you didn't finish it. And it's got the right button. It's got a little message. Yes. It's like when you come back to the page of the sponsors, it's hey, you started this, but you didn't finish it. Like, you know, click here to finish it. Like, it just did all that. It just knew to do it. It did it. And it looked nice. It was done. 4.8 is not doing that. 5.5 is not doing it either. And you brought **Aaron Francis:** the kindergartners in to finish **Ian Landsman:** the job. So bad. I don't want to go back to hand coding, but it feels like I am. It feels like I'm hand coding again. It's like, **Aaron Francis:** boy, how quickly we adapt. **Ian Landsman:** Isn't that crazy? It's crazy. It's like you used it for a day. And it's like, boy, it's so much better. --- ### [AI Releases Can Prompt Rapid Political Pushback](https://share.snipd.com/snip/befa1337-bb56-40e8-a778-b2d862a0c2e5) 🎧 59:00 - 01:02:28 (03:27) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/68fba8d1-1fb0-491b-8a64-234880e6ea4a" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Cutting-edge models trigger political and regulatory reactions that shape access quickly. - Ian and Aaron discuss Fable's removal, U.S. government intervention, and the likely short-term vs long-term availability tradeoffs across providers. #### 💬 Quote > It's over. Because no model, like, going forward, I can't imagine maybe the next, the very next micro generation is, like, less powerful than Fable. > — Aaron Francis Aaron Francis on the significance of Fable 5's removal #### 📚 Transcript **Aaron Francis:** It's over. Because no model, like, going forward, I can't imagine maybe the next, the very next micro generation is, like, less powerful than Fable. But after that, this is it. We don't go backwards. No, we're not. I mean, this is **Ian Landsman:** why I'm going to be very interested to see what they do with open AI. Because if you're saying, listen, we are at nuclear weapons level, right? This is nuclear weapons. You can't have a nuclear weapon in your house. That's going to be true of this class of model and beyond. Then let's see it everywhere, right? Let's see the open AI. You know, the next open AI one's going to be in the ballpark of as good, right? It's very unlikely it's going to be that Anthropic has some magic juice that's like, they're so much better, right? They're five years ahead. I don't think they're five years ahead. I think they're a few months ahead. So, I don't know. We'll see if it's politics or if it's legit. If it's legit, I would like to see some actual laws. I know we don't do that in this country anymore, but I would like to see some laws that are like, this is, we're going to put some guidelines around this in a way everybody understands and we're all agreeing to. I got to **Aaron Francis:** say, this is the worst 12D chess I've ever seen from any CEO in all of history. The 12D chess? Yes, my goodness. **Ian Landsman:** What Make it seem like I'm building nuclear weapons and giving them to every rando yeah the **Aaron Francis:** it's like i'm building a nuclear weapon this is too powerful to release um i can't give it to the u.s government i won't work with the u.s government if anyone builds it everyone dies announcing fable five like what did you expect was going to happen? Like, this is literally what you were asking for. You wanted regulation, and then they hit you with this pseudo-regulation, and you were like, oops, not like that, you know? I don't know, man. And, you know, on the flip side, I'm sure you've read the Paul Graham either tweet or essay about if Sam Altman were, you know, parachuted onto an island of cannibals, you'd come back in six months and he would be their ruler. Like, have you read that from Paul Graham? That **Ian Landsman:** sounds kind of awesome. I have to go read that now. So on the **Aaron Francis:** other side, you've got the actual 12D chess master who is Sam Altman. And you have to wonder now what happens to GPT 5.6? Like, because he's playing the game. And meanwhile, Dario's like, I hate that I'm building this civilization ending tool. $200 a month. And you're like, why? Come on, dude. We've talked **Ian Landsman:** about that before. I don't know. I feel like it's such a powerful tool in a positive light that you don't need the negative aspect to sell it. I agree. It sells itself. You have something that literally sells itself, which happens very rarely. If you can just get anybody to taste it for a second, it just sells itself. It's so much better than what you were doing before. Like, just keep giving out tastes. Like, so, yeah, I don't know. They've definitely played that, I guess, incorrectly. I mean, we'll see. But probably they played it incorrectly. But it also is like, who is really being hurt, I think is an interesting question. Me? Oh, well, that's for sure. But, you know, all these Chinese models, they're just catching up all the time, every day, every minute. --- ### [Make Sponsorships Optional And Marketplace Ready](https://share.snipd.com/snip/407f2259-20f7-40bd-9c8f-a45a9b112d09) 🎧 01:09:59 - 01:14:29 (04:29) <iframe src="https://share.snipd.com/embed/obsidian-player/snip/52c49913-5c98-438c-a017-58a22d4c5858" width="100%" height="100" style="border: none; border-radius: 12px;" sandbox="allow-scripts allow-same-origin allow-forms allow-popups allow-clipboard-write" ></iframe> - Build sponsorship tooling with optional Stripe connect and a marketplace to attract both podcasters and advertisers. - Ian built Outro to let hosts optionally connect Stripe, manage deals, and later list shows with basic metrics for advertisers. #### 💬 Quote > You can just manage deals through there if you want to without billing. You can use it as like a back office without taking the payment. > — Ian Landsman Ian Landsman on Outro's sponsorship model #### 📚 Transcript **Ian Landsman:** But it's very sad because Fable 5, I know I'd be done already. **Aaron Francis:** So what's the model of the sponsorship? So I connect my Stripe as a podcast host. **Ian Landsman:** Optionally. You don't have to. Okay. You can just manage deals through there if you want to without billing. **Aaron Francis:** Oh, I can use it as like a back office without taking **Ian Landsman:** the payment. Right. Smart. Okay. Because I know big shows are not going to ever use this for payments, right? Like Bill Simmons, if he uses this, is not going to do his payments through this thing, right? He's going to have some big **Aaron Francis:** department. You're going to do an for $5 million for three episodes. Ah, damn it. So then can I like, is there like yet a marketplace or a public listing of these shows except sponsors? **Ian Landsman:** No, but it's there. It's ready. It could do it, but it's not doing it yet. Because I figured **Aaron Francis:** not what's the point **Ian Landsman:** of doing it yet. There's no point doing it yet. Nobody even uses it. But yes, you'll be able to do that. We already had somebody ask about that. Bento was asking about that. So that's in the works and i think that's how you sell the **Aaron Francis:** dream to the podcasters yes **Ian Landsman:** you say you'll be listed on this on **Aaron Francis:** this page where advertisers come to spend money and every podcaster is going to be like i want money i that's how how you get, especially if you tie back in some sort of metrics. So you know, presumably you know the podcast feed, and then you could, like, offer OAuth to the big five players, know, Transistor, whatever, whatever, and pull in their stats. And then advertisers can say, like, oh, this podcast gets this many listens. They do episodes this often and they're asking this price yeah that's like that's some that's some transparency that i don't think exists out there that is interesting **Ian Landsman:** i wonder i i don't know if that level of transparency is even good for the podcasters but i'd like where your mind's at in general of like uh there's also like a lot of weirdness obviously nowadays with like well there's the audio listeners but then there's youtube right then there's shorts but then there's like seven places you actually need to get data from I **Aaron Francis:** wonder if PodScan has it all already that data I don't know if **Ian Landsman:** they have that exact data maybe they wouldn't have though estimate but I don't know how they get the listeners like he does estimate that I don't know how he does it because he doesn't have the actual data I don't think well maybe that those are public endpoints like maybe the apple podcast endpoint to get those stats is public i guess maybe it is um so yes but i think even like phase one of it just being like hey here's marketplace some filtering on types of podcasts maybe that podcasters have a place to put their metrics in. Yeah, that could be like a phase one. I think there's even like a bigger world of like big, big sponsors just dump a pile of money on us and we distribute the money out in a logical way, right? So I think there's like a bunch of options there, but that's all like phase two, three type stuff to me. But I do think the idea of having a marketplace pretty early, I don't know if it'll be V1, but pretty early to like at least have the basic, like here's a list of all the podcasts and the platform and yeah, like tags for what their topics you know what their general topic area is and some basic stats and whatever blah blah um yeah i like that so it's there me and fable had worked that part out we had made sure that everything we were building was like prepared for that and so we're good to go on doing a marketplace um once we have some shows besides token town and mostly which the next show is coming july **Aaron Francis:** 8th i believe is when you have to onboard someone else i think **Ian Landsman:** it's gonna work i think i think it's possible this week off for me in the middle is a little bit annoying but i still have a week when i get back so you knew that when i knew it i knew it so i think we'll get somebody in there i want to get sponsors done which it's almost done and it's pretty complicated thing so it's almost done and then uh i don't know i wouldn't mind having the mailbag but i don't think i need the mailbag to get somebody else in there so i think we can get somebody else in before the mailbag so yeah, I think we're almost there. Um, you know, once you let that person in, they're going to feedback and they want things. Boy, don't I know it. ---