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From Pivot Hell To $1.4 Billion Unicorn

Y Combinator • 2025-12-10 • 38:47 minutes • YouTube

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From Pivot Hell to Unicorn: How PostHog Built a Remarkable Developer-Focused Analytics Company

In the highly competitive world of tech startups, few stories are as inspiring as that of PostHog, a company that evolved through multiple pivots to emerge as a $1.4 billion-valued unicorn. We sat down with James Hawkins, CEO and co-founder of PostHog, to explore the journey from their early days in Y Combinator’s Winter 2020 batch to raising a $75 million Series Z round, and how they carved out a unique space in the crowded product analytics landscape by embracing openness, humor, and authenticity.


The Early Days: Pivoting Through “Pivot Hell”

James and his co-founder began their startup journey with a series of ideas, working through what many YC founders call “pivot hell”—a cycle of trying multiple ideas before finding product-market fit. Initially, they tried a sales territory management tool aimed at helping sales leaders optimize their pipeline, but despite positive initial feedback, actual user engagement was low. They quickly realized that building for sales leaders was challenging due to the poor signal-to-noise ratio and decided to pivot toward building tools for more technical users like engineers, who provide clearer, more actionable feedback.

Their YC application even featured a product where developers took surveys about technical debt during pull requests—a stepping stone on their path. However, the breakthrough came just weeks before Demo Day with the launch of open-source self-hosted product analytics, a tool designed to solve a frustration they faced repeatedly: the need to implement product analytics over and over again, often hindered by ad blockers and lack of data control.


The Breakthrough: Developer-Focused, Open Source Analytics

PostHog’s defining insight was recognizing that existing analytics tools were built primarily for product managers, often requiring engineers to implement cumbersome setups. They wanted something that engineers could own directly—one that was open source, self-hosted, and allowed querying data with SQL directly from their own infrastructure.

This fresh approach resonated strongly with the developer community. Launching on Hacker News, PostHog quickly gained traction as the most upvoted dev tool post of the year, marking the beginning of its rise. James recalls the excitement of this launch as a turning point, even though back then the product was still “mediocre” by today’s standards.


Fundraising in the Face of Adversity

Raising money in early 2020 was fraught with challenges. Just as PostHog was launching, the COVID-19 pandemic hit, causing many investors to pull back. What started as meetings with top-tier VC firms became a grind of securing small angel checks to keep the company afloat.

Despite the stress—especially with James’s wife pregnant back home and visa concerns for his co-founder—the team persevered. Eventually, they closed a seed round and quickly followed it with a Series A once the market recovered. James candidly admits their early pitches were “vanilla” and that learning to be more opinionated and passionate about their vision was key to winning investor confidence.


A New Era: Scaling Up with AI and Product Autonomy

Fast forward to today, PostHog is a team of 160+ people serving over 300,000 users with 16+ products in various stages of development. The company is aggressively expanding its product suite, leveraging AI to automate tasks like generating pull requests based on customer data insights.

James describes this phase as the most fun yet—comparing it to unlocking “rocket launchers” in a video game. After years of hard work laying the foundation, PostHog now has the resources and confidence to build deeply integrated tools that help product teams understand and improve their user experience autonomously.


Building Trust and Connection Through Radical Transparency

From day one, PostHog embraced building in public as a core strategy. Trust was paramount, especially for an open-source product analytics tool where users’ data privacy is critical. The company’s website goes far beyond typical marketing pages—it features detailed documentation, team bios with personal touches (like engineers’ pets!), a developer job board with unique filters, and a transparent company handbook.

This openness humanizes PostHog and fosters a community that feels connected to the people behind the product—an essential edge in a crowded market.


Standing Out with Humor and Contrarian Marketing

Perhaps one of the most memorable aspects of PostHog’s approach is their bold, humorous marketing—most notably their quirky billboards scattered around San Francisco. These ads parody vintage Americana and traditional corporate advertising with playful, offbeat messages like comparing session replay to tomato sauce’s “sweet taste of understanding.”

James explains their philosophy: in a world saturated with ads vying for attention, being funny and bizarre is more effective than playing it safe. This “transcending corporate tryhard” approach, combined with a culture of brutal internal feedback to hone every joke, helps PostHog cut through the noise and make a lasting impression.


The Website as the Sales Team

PostHog’s website is another standout feature, described by James as their primary sales tool. Unlike typical SaaS websites optimized for quick conversions, PostHog offers a rich, multi-dimensional experience designed to engage and educate their technically savvy audience.

They intentionally went beyond the “80/20” effort most startups settle for, pouring resources into making the site remarkable and polarizing—knowing it would attract passionate users and spark conversations, even if some don’t love it.


Key Takeaways from PostHog’s Journey

  1. Embrace Pivoting with Purpose: Don’t wait for perfect ideas; try multiple approaches to discover real problems worth solving.
  2. Build for Clear Feedback Loops: Target users who provide honest, actionable feedback—engineers over sales leaders in PostHog’s case.
  3. Be Transparent and Build Trust: Openness about your product, team, and company builds authenticity and loyalty.
  4. Invest in Remarkability: Whether it’s marketing, your website, or product, go beyond the norm to stand out in a crowded marketplace.
  5. Use Humor to Cut Through Noise: In today’s attention economy, being funny and bold can amplify your message far beyond traditional tactics.
  6. Scale with Confidence: After laying a solid foundation, leverage resources to pursue ambitious, innovative product visions—like AI-powered product autonomy.
  7. Persistence Pays Off: Fundraising and growth are tough, but consistent effort, learning, and resilience can lead to success.

Final Thoughts

PostHog’s story is a testament to the power of resilience, creativity, and authenticity in building a modern tech company. From the grind of pivot hell to the celebration of unicorn status, James Hawkins and his team have shown that a developer-first mindset combined with transparency and a bold marketing voice can create a brand that not only succeeds but also inspires.

For founders and builders navigating their own journeys, PostHog’s experience underscores the importance of being remarkable, staying true to your audience, and embracing the messy, iterative process of startup life.


Ready to learn more or try PostHog? Visit their website to explore their open-source analytics platform and see how they’re changing the way product teams understand user behavior—one quirky billboard at a time.


📝 Transcript Chapters (8 chapters):

📝 Transcript (1356 entries):

I'm here today with James Hawkins, CEO and founder of Post Hog from the YC Winter20 batch. James is here hot off the news of raising a 75 million series Z round of funding at a $ 1.4 billion valuation, making Postto the latest YC unicorn. Today we're going to talk about how Postto got started, how they pulled off what I think is one of the best YC pivots of the last decade, and how they use attention and humor to compete with not just other tech companies, but with everything out there for attention. Welcome, James. Thank you for having me. James, could you tell us what is Post Talk? Explain it to us a little bit. >> Sure. So with YC, I always feel like this is my homework being marked by the teacher. Um, we help users to debug their product to ship features faster through kind of things like feature flags and so on. And we help keep all their kind of customer and product data in one stack. >> And tell us a little bit about um the state of the company, how how big it is. You guys are pretty big these days. G give our give our viewers a snapshot of what's going on at Post Talk. >> Sure. Yeah. So, we're about 160 people. Um, we're around 300,000 customers across like free a lot of free customers and paid. um we have several thousand paid. We have I think 16 or 17 products kind of in production or um in development. They're all at different kind of stages. And we've been I guess like at the moment the main thing we're doing and the reason kind of why we did a lot of raising this year. Um we're pushing very hard on getting more products still out of the door. So instead of kind of going up market, we're going just across more of kind of the customer data that people are generating. Um, and we're automating a ton of things through AI, which has been a long and arduous pro process. Um, but we're starting to get to the point where I'm starting to get proud of what we've achieved so far, but I still kind of feel like ah, we haven't got started yet. There's a lot more to go. Um, which I don't think is a feeling it will ever go probably, but um, yeah, it's like proving a lot of fun and we're just starting to scale up pretty aggressively now. Like we're I think we start at 70 people this year. Um, and so we're supposed to be about 200ish by the end of the year or something. So it's time to get properly and to kind of scale up maybe at this point. >> So you've got this team, you've got all these customers, you have all these products that you're developing and improving on, but what what was the initial product that Post HTog started with? What was that the first thing that you guys brought to market as Post Hog? >> Sure. So yeah, the first thing that worked for us, we had a bunch of pivots before um was self-hosted product analytics because we pivoted so many times and every time we had to set up product analytics over and over again and we're just getting frustrated having to implement it. I think we found that there's an awful lot of really strong competition. Um, but we felt all the products were built for kind of product managers to force engineers to go implement. But as like reasonably technical, especially my co-founders, a very technical co-founder was just getting annoyed at like I can't I want to write SQL. I want to see the data underneath. I would like to keep this in my infrastructure so I don't lose data due to ad blockers. So we thought, okay, we think there's room for a self-hosted alternative. And we also we spent some time talking to potential customers. Um, and we found that quite a lot of people had self-built their analytics stack and we're maintaining this kind of junky system which we felt if we can productize something like that because new infrastructure and we could see this working quite well. Um, so yeah, we started with just open source product analytics on hacker news. We spent like the last four weeks of the batch uh desperately trying to get that out of the door and then we hit like we actually we didn't really pivot we iterated I would say afterwards and now we're all cloud-based with multi-roduct but that was the thing that landed um for us finally I think of postg um well there's this meme um among founders of pivot hell and it's a thing that YC founders talk about a lot where you're going from idea to idea to idea and you're trying to find something that's going to work and you guys not only came out of pivot hell and have built this awesome But what you built was literally forged in the fires of pivot hell, >> right? Like while doing these pivots, you had this pain that only came because you were doing the pivots and trying to do them at a high level, setting up the analytics over and over again. Tell us a little bit about how you guys actually got to YC and and started this journey of of pivoting and finding startup ideas that might work. my co-founder uh quit. We used to work together. Um and when I heard news that he was leaving, um I had also been thinking about leaving and that kind of triggered me to go, okay, I want to do my own thing. Um so I made sure to grab him and instead of getting him to go off and work in um another startup, whatever, I thought, hey, let's just do our own thing. >> And when he when he was leaving, was he leaving to join another company? Was he leaving to start something? >> Yeah, I think he was actually trying to get a job at Facebook at the time. He was doing an incremental kind of career move. Um and I think I showed up being like I think I have this idea that we'll probably have product market fit for in a couple of weeks time. >> Of course. Of course they are. >> Of course. Yeah. It's only a hop skip and a jump away and then we can just you know um I had like a I'd created a list of problems I'd encountered professionally thinking okay I should solve a problem I've had myself and we started going through the list but we thought we wanted to bootstrap initially. So the two of us were just like working out of coffee shops. One of the main problems we found was every time we went to see a customer, we'd have to buy another round of coffee. And so we'd often end up getting like whatever the coffee equivalent of wasted is basically. Um so eventually we we did this for about 6 months and we worked through an average of one idea every like five probably average about five or six weeks. >> Do you remember what any of those ideas were? >> Yeah. Um so the initial thing we tried to build was a sales territory management product. So, I used to run a sales I was VP of sales and I felt that like in sales, you're literally wasting over 90% of your time because deals don't usually win. They don't usually close. Like they usually just float around and gradually get killed off. And we thought if we get better at not focusing on deals that are closing, but on the ones that aren't closing, getting a bit more ruthless at using statistics to pull them out of people's pipeline and change the territory for the sales team is what I thought might work. Um, and it was just kind of really complicated um to build and I think because I'm much more technical than a traditional sales leader would be, I just think we built something kind of complicated and I don't think our go to market was right or anything. Um, yeah, we had this idea, we built it. I think the thing that was important or the harsh lesson I learned was my co-founder was building it. I was just trying to get interesting prospects to buy it from us. Um, so I had about I got through I got about 15 sort of series B, C, D um, sales leaders queued up saying they wanted to use this. Well, they said they wanted to use it. We got the first version done in a couple of weeks. Send them the link to create an account. Of the 15 um 14 of them didn't even click the link. One click the link and then didn't create an account. And we're like um it was like first good we should have read the mom test was the we hadn't done any of the user interviews correctly. Um, but I also it made me feel that building for sales people or sales leaders in particular, I feel the signal to noise ratio is pretty poor. Um, because they're really quite willing to hop on quick calls and are very very positive and kind of very friendly people. A little bit later it kind of dawned on us that we think we'd be better because we're not very good at product. We're terrible at product initially because we're kind of bad. We need to deal with people that are what they say is close to what they'll do. And we felt that like natural problem solver people like engineers or customer support people probably would be a better audience for us to work with because out of all the many variables you can get wrong. Like it might be like your product's incredible but you're terrible at explaining what it does. You'll still fail. Um and we thought that okay one of the variables we can remove from this equation is the person being a little bit um easier to read basically. And so that was a big part of why we wanted to build something dev tooly later on was that sort of realization. >> Um but yeah that was the first thing that we worked on. And so when you guys did Y Combinator, the product that you had was another pivot was having developers take surveys about technical debt when they would submit a poll request. >> And so you'd already done a few products by that point. >> You came into YC with another one. Did you guys have a like how did you kind of keep your spirits up or how did you track your trajectory? Did you feel you were getting stronger or better or closer to the target as you were going through these pivots? I would like to think that was true. I'm not sure it was. We didn't reflect on that. We should have asked like are we actually getting better each time around? Um I think we should have run a retrospective basically. I don't think we actually were getting that much better each time. There are definitely some things that were consistently very important to us though. Like for example, we went full gas on each idea. Like we didn't sort of like call it in. Like we would go in person to every single customer that was remotely interested, we would go in person to go meet. Like we started in uh England and came to San Francisco to do YC. like we'd catch like a bunch of trains and buses to get to a customer in some random place and like we would put the effort in to go really push it because then kind of what happens when we started charging for a lot of these products. You would find that oh I'm not failing this cuz I don't have a relationship or like I'm kind of friendly with this customer at this point and they still don't want to buy from us. This is a really good sign this product isn't solving the problem. This really demonstrates to me it's a nice to have. Like in my previous job, um, we used to sell comp like enterprise software for millions of dollars a year. And I can remember multiple times thinking I'm having to work kind of as hard to sell a like $50 a month SAS subscription as I was to sell like a $100,000 a year plus deal in my last job. >> I know that I've tried really hard. Um, and so I can rule out one of the other variables I guess is like, are you actually trying as hard as you could be? And we were. I think that helped us feel confident enough to go this just isn't working. So yeah, we just we worked very hard. And it look I I remember it feeling weird like on LinkedIn for example I talk about like hey this is what we're up to and it would be like one week it was like some dev tool next week it's a CRM thing. Um but we just didn't care like we just threw ourselves into each problem. >> There's an aspect of shamelessness that you have to have to just kind of keep up the momentum and keep trying and not get bogged down. I think it's easy for it to feel kind of lame almost. Like yeah, you have friends who are like in investment banking or they have these like proper careers and we're doing something that just seems so kooky, but like that's the bit I think that is a specific reason why most people don't run companies because that first bit is like all is so existential and all over the place. I think we just have faith that if we just keep making the input we're looking at is like are we making very regular real progress? So on the ideas we'd often at the start of the week be like okay by the end of this week what is the list of things we will feel good if we get them all done and it would be something like okay we want to do like 10 custom meetings build these three big features um and we just held ourselves to account on a like very short cadence all the time as people I think we got much stronger at things like product much later on once post dog had sort of taken off but I think we were just like very we just yeah put our heart into things we're very fast that was kind of all we needed I think realistically you guys were working through these pivots maybe getting better, maybe not. Trying to be wholehearted, trying to be consistent, trying to be really committed to the bit, maybe as a comedian would say, when you started with the open source product analytics, what became the final pivot, what signals did you get early on or signs that maybe this is it, maybe we're really on to something was a month before YC demo day. Tell us a little bit about how that unfolded. >> Yeah, so I think um we had a slightly higher level of excitement about this idea ourselves. I think we had had a couple of ideas where in our heart of hearts we weren't that interested in them. Like we were kind of doing them because we like felt like we had to get something to work. Um whereas I think this one and we had an office hours here and I can remember and we're like well we're kind of thinking about building this thing that will do two at the time. We thought there are two things are important. We thought we want to capture all user data completely automatically. Like we don't want anyone to have to set up event tracking manually. We didn't realize someone had already built this. Um and that didn't turn out to be particularly important. But then the second thing we're like we want to be able to self-host this thing so that it can say your infra and we came out the office hours I was going ah that's not the right framing it's open source product analytics then it's not just about it being your infrastructure it's also just like a whole vibe like I think immediately we were like we feel very confident I could see that really landing on hacker news that we both my both read it and it just felt like the kind of thing you would see on the front page so the level of excitement was a little bit higher for us I do think it's a bad idea though to like sometimes I see other founders they're like I'm waiting for an idea that I'm excited about but I think The reality is for us it's we had to just build a bunch of things to find the thing we're excited about. What we didn't do was like sit cross-legged on the top of a mountain waiting for inspiration. >> Um so by trying a few things we started going this idea just doesn't feel good. But we know that because we have tried it. >> You had to find something in the middle of what people want and what you're excited about. >> Yeah. Exactly. Um and so will I think doing stuff gives you much stronger I think it's like a Brian Armstrong quote but like doing stuff gives you much stronger signal more information. And then I think when we started booking interviews, it was a little bit easier to get people to talk to us. Um, but the big deal was on Hacker News when it was just on the front page and had like it wasn't the best ever. Like at the time it was pretty good compared to what happened before. >> It was a good launch. We had a good hacker news launch. >> But if you look at it at like sort of like 20 23 24 vintage hacking news launches, it was very mediocre, but it was enough to get an initial audience. I I think um I because I go back to people's old demo day slides a lot of the times when helping batch founders figure out what they should say. So I I pull up the post hog slide every now and then and I believe according to the slide and I think it's true it was the most uh upvoted dev tool hacker news post of the year. So pretty good. I remember being in the office hour you probably shared the idea with a bunch of people but I remember the first time I heard it and it just made a lot of sense. Uh there were a bunch of product analytics uh companies out there but no one had really gone all the way to make this truly developer focused by going open source. Um and so it just sounded like something someone should try. Uh, and uh, I wasn't that surprised that it hit when it the way it did and was really excited for you guys at the time. So, okay. So, you had this um, you were starting to get some users. You had to go out and raise money for this thing at demo day and you'd only been working on it for a few weeks at that point. What was that like? Like, how do you get your conviction up to go, you know, pitch investors about a product that's really only a month old at this point? It was a very mixed. Um, we at first we felt really good. We're like, okay, it feels like we can have this done in like two days or three days. Slam dunk. >> Yeah. Yeah, I think we're coming in going like, "Yeah, we've had a really solid launch." I think we were still buzzing a little bit after like oh it's such a a feeling of kind of relief that suddenly we've got something where it just instantly the day we launched it went from being a push basis to a pull basis getting people interested like suddenly it's just like we're trying to service all these random problems or feature requests and stuff we can see coming in and so we went out to raise I think very confident like we thought we'd kind of be pushing quite big valuation at the time and I think we felt that we will have this done in just a few days um but our the timing was horrible because it was 2020 in March And the same week basically co went from being this somewhat niche thing to changing the world and everyone just suddenly pulled out. So we kind of went from feeling like oh we've got like all the fanciest VC firms in the world are interested in this thing to everyone's pulled out and we're now doing like we're trying to get angel checks for 5,000 bucks a pop to try and get all the way up to like raising a few million dollars. This is going to take a long time. Um so it was very peaky and we also had a lot of stress over like we're in the US still. My wife was at home and pregnant and I was worried about getting stuck in America and my co-founder left and because he was also worried about getting stranded, overstaying his visa and stuff. So there was just all this chaos kind of happening. We just kept plugging away basically. Um I think it was very easy to it would have been very easy I think to get disheartened and it was painful but we just didn't I guess we just kept going um was the main thing. And so we were doing angel checks um happily taking 5K off of people um until eventually we got um a proper term sheet um and that led to another one and then we um got the round done very quickly and then the market completely picked up like even just a few months later end up doing like a series A like a month after the seed round had closed but I think the statistics are something like >> I think we met 160 different firms in the seed round. I think for like if I added up the total number of pe number of firms I've met for the series A, B, C, D, and E, probably like 20 uh in total like 30 in total. It's it was by far the hardest round we had to raise. Uh but also we sucked it. It's not just them market like we sucked at pitching. We're trying to people please I think too much. Um so we would be like well they were like what are you going to do with the money and it's like well you know we'll like kind of get some revenue. We'll build some features which is very vanilla feeling. Um, and we had a lot of people rejecting us because they felt we were too early. But the reality was it's like, well, we're dealing with a lot of these investors have never invested at that time. They never invested in open source at all. Like the vast majority hadn't. Um, because it was quite it was much more unusual then. And I started realizing that I don't even believe that we'd want to spend money across all these areas. Like we actually just want to go full all in on the open source project for a while. Um, again, I think that's very bad advice for something that doesn't have competition that's making lots of revenue. So be very careful with something like that. But we started getting much more opinionated and that's what started that eventually landing. Hey, like you're out of your mind if you think we're going to go big on like hiring a big sales team or trying to go into the enterprise or something like it's just about building this like nice big inbound kind of community. We think is the if we can't do that nothing else will follow and we need to make really establish that properly. Um so yeah, we got much punch here. >> It's funny how that is. It's almost like investors are pretty agnostic on what the plan is. So long as there's a plan >> and that you you're really passionate about it and you've thought about it and you're ready to go execute on it. >> I think there's a Mark Benoff quote which is something like um it's better to be different than right. I think that it's almost the equivalent here where I think it's if you're trying to raise money, it's better to have a plan that than it is to necessarily be like somewhat correct, like be either very clearly right or wrong because you'll learn something from that. So, that round was really hard. You talked to 160 investors. It took months to get the money. Yeah. Okay. >> Fast forward to this this latest round that you guys just raised. Obviously, it's 5 years later. Things are very different. The company's in a very different place. You have revenue and customers. What's it like to raise a $75 million round? You know, how is that relatable to folks that maybe are out there trying to raise the first money for their company? What's that experience like? >> Yeah, perversely. It's easier. Uh like we had um we spoke to one investor for this round. We raised from Pete 15. Um this one called Chelendra that is the main partner, but also Anav um is involved as well. The round before he tried to take part in, we only had just gotten to know him though, so we kind of felt like we want to spend a bit longer with you before we raised with you. Basically, we did spend a little bit more time with them because we liked him as a person. They offered to do the next round preemptively and at first we thought it was a bad idea um because we just felt we don't know how we would spend this. We haven't spent like the round before the round before almost. But then at the same time what was starting to happen was we were getting increasingly confident on AI. Um what actually happened was I went on vacation and read um about some of the motives for why some of the co-founders built open eye in the first place and I thought the reasoning was really interesting. It was humans have a brain um it's a physical object. We can therefore build one basically and there's no technical reason we can't build ADI essentially. Then I just this is nerdy reading but I started thinking like what are the specific differences between your brain and LMS today and I kind of concluded there's a lot of things that could be built but I don't understand why they don't exist yet. So I therefore think that AI will I don't think it will flatten out like I think the rate of improvement may vary but I think over a long time frame it will be incredibly important to the world. So I got much more um bullish on its importance and then thinking at work I'm like okay I can definitely see a path like I just spent some time reflecting with my co I'm like okay how could this shake out basically like should we change our strategy if we both believe this is this important so at the time we were thinking about building like a CRM a support platform all kinds of other data customer data oriented products >> and everything was kind of working but we felt actually we can do so much more in the realm of product at first like we can build kind of product autonomy out um so we want to go deeper within our products that help you understand what to build. So we wanted to work on like at the moment we're working on like a desktop app for example that ships pull requests based on your customer data. So it'll look across all your session recordings or your analytics or your error tracking your LM traces go hey these are the issues we can see in your customer base we literally fix them whilst you're asleep. Um here are the pull requests. So instead of like please build me this feature it will be the flow is pull based. So it's like hey we've built these features based on what's happening. um you can just review, close, edit, merge them depending what you want to speed up development further. Um and we just were like, hey, let's just go we want to be able to go all in on this idea. Um and so we raised to have just like the comfort and the confidence. So a lot of it psychological like I don't think we'll manage to suspend it. Um but we want that's kind of the point. It's like this means that we can just fully embrace um our product strategy and take it bigger and just like increase the size of swing that we're taking. Well, and it sounds like what you're saying is uh you're able to fully explore the implications. Yeah. Of the original idea of post hog, which is understand what's happening in your product and what your users are up to. And there's all this stuff downstream of that like once you understand it, then you can do these things and take these actions. Yeah. Cuz we started thinking like, okay, it's a bit like if you're trying if your customer is like a painting that you're trying to understand. If you have one data type, um it's a bit like seeing a painting but only be able to see the color of blue. You're not going to get a nuance understanding of your customer. Like looks like they're not using this feature. we should email them to cross- tell them the new feature we've just built. But at the same time, your other data might be telling you something conflicting like they're really pissed off in support right now and this is a terrible time to automatically send them an email or something. So we kind of felt like and that's what a human would do it today is you kind of look across your tools and we thought oh we can basically just build something that does this. Um and so we set off trying to build basically a product manager that's a physical thing we can build it. >> Yeah. We don't want to build something that has like that we can't conceive of. We want to build something that exists but just like a better version. And we were like well there's a human product manager has product market fit like companies buy those that is sort of where the idea came from. Um so instead of just building because normally our strategy had been what are the products have product market fit have customer data we will build all of them it's more convenient but then we well also like you could consider the team members um and thinking about sales has product market fit in companies so does support so does engineering um so can we build those things now because it's now possible uh I think it's going to be correct that that works but we'll see. >> All right. All right. You mentioned to me before we started talking today that you're h this is like unexpectedly maybe you're having more fun than at any other point in the company so far. >> Um and that is a little counterintuitive to people. Uh a lot of founders say oh the early days are the most fun and they kind of look back nostalgically. Why do you think you're having more fun now than ever before? >> The the work feels much more leveraged now which is quite entertaining. I think before you're so much of our focus was trying to get attention from people because you have no attention by default. It's the world is very noisy and so I'm just like sending emails and LinkedIn messages into the ether basically and it just feels like I'm doing an awful lot of stuff that has no impact. Obviously when you do that like a tiny little spark it then leads to a big fire. Whereas now um it feels like we're playing computer game. We've just unlocked like rocket launchers or something. So it's like, oh, we can like go absolutely nuclear on this particular idea and like really fully build it out in a way that would be very hard to we're like lucky enough to be able to build this because it involves having to have like 15 or 16 products and also a bunch of AI stuff and we need to be able to like have the time to build this because like there's been remarkable work at like intercom where they built pin um and what we're trying to do is analogist to that I think but it's not making posto work with kind of what a couple of products it's trying to make it work across like 16 of them. Um, I feel like we're going much deeper than we've ever been. But it's enabled us to make a bet like that. Like I think similarly if we're starting from scratch, trying to build what we're now trying to build would be impossible. I think like SpaceX or something um is a much more grandiose idea. Like on day one it's not building um like the transportation from Mars. It's like day one's like we need to build actually a relatively unambitious satellite launching business. I think we've been we've sort of done quite a lot of the homework. That means we're able to now >> do these take the bigger test basically. >> I wonder how many products Post Hog would need to have to be as grandiose as ambitious as SpaceX. Yeah, it's an interesting comparison. You know, you mentioned like having fun getting this work out there. Like um I know building in public is something that you're keen on. What does that look like as a CEO is getting this attention, getting that spark and and putting it out there and trying to start a fire. How do you think about that and doing it in the open where people can see what you're up to and hear about it and follow along? >> Trust was the original reason for it. Like we just felt that even if you're offering like most of our users don't pay anything like you the open source project and no one paid but it still takes up there is a cost like it's trust in terms of what are they doing my data um and also just time with setting this tool up. I think especially software is getting more like as it's getting quicker to build. There's more software appearing. It's getting just more and more competitive. I think it's got it's become a step change more competitive with AI. And so we felt that okay the fundamental thing we have to achieve in marketing is we need to highlight how we're different because it's in a busy industry. Uh and then we need to build trust with users and like the foundation of trust we felt was transparency. So um instead of just having like a one pager landing page we're going to like really fully explain everything we can about who we are what we're trying to do. I think that gave us the trust we needed. Um, and we thought about kind of I look through other hack and use launches and just sort of summarize like okay these are all the pieces of critique I can see and so we're going to make sure we have transparent answers to these types the questions would be things like they don't have a clear business model I don't think this is sustainable for example there's like this sort of inherent suspicion of ideas and we thought okay let's just like think through >> these types of questions that we know that our audience developers would have and we'll just address them on the website. So we like you know we didn't have a pay product. We said hey this is how we think the pay product is going to work in future. >> And that was from like day zero. You you put some of those things in practice. >> Yeah. Like before we launched Hacker News. I think the other thing we realized from a content and like a marketing perspective was I think experts writing about things is more compelling often than non-experts. If you look at like the front page of hacker news there'll be like incredibly technically savvy people talking about very complicated topics quite often. >> And I thought man I'm like don't I'm not clever enough to get there but I need to figure out a way to get us visible in hacker news is like the probably the most popular place for our audience. And I thought well I am the thing I'm actually an expert in is our business and so I can write about what we're learning and doing and so I feel like a really natural topic. So we like we wrote a blog post also doing the Y bad batch like shortly after the launch of what it's like moving San Francisco. >> I remember that post. Yeah. >> Yeah. Um and again that was also viral but I think I build a lot of trust because it humanized us underneath. So I was like put photos in of like we climbed up like Twin Peaks for example in the night at night. I think people realize like oh there are human beings you know in the same way that someone might be really aggressive online but as soon as you meet in person they're much more chill. It's the same sort of feeling and we're trying to make that clear like with all our products today. You can see like the literal engineers that we have every single team member on the team pages. You can see all the so you can look at like product analytics. You can see the handful of engineers building it. You can click their bio and read about like their pet cat for example. So that you're like oh there are people building this. The humanization I think is really important to stand out basically. Yeah. It it lets people know someone's at home. You go visit this house there'll be someone there and you'll have a neat interaction. I actually I I think about your your moving to San Francisco post quite often over the years since because if you look at it, there's nothing that remarkable in the post, >> but you got it on Hacker News. People read it, they talked about it, it was discussed, and I think you're right. It's because you just showed some of your humanity behind uh this product that people could use. And everyone's looking for ways to relate to to folks like themselves. I remember when I read that I thought, "Wow, they can they can, you know, climb up Twin Peaks and write about it and get developers to want to check it out. They've got, you know, this is going to go somewhere." Um, building in public is one of the ways that you guys have really connected with developers. I think another aspect of that though is is humor and u bringing a sense of like marrynt, amusement, and maybe even a little chaos to how the Post Hog message gets across. One of the manifestations of that was present all over San Francisco this last year with the the crazy billboards uh that you guys put up. In my opinion, like there's billboards all over the city. When people move to San Francisco, they're shocked by all the tech ads everywhere on all the billboards, but I don't think I've seen anyone do quite what you guys did with your marketing. And so, I thought it'd be really fun to just take a look at some of these together and and get your take on what's going on here. So I guess this first one is about session replay ostensibly, but it's a also like an ad for tomato sauce and it's promoting the sweet taste of understanding. Where did you guys come up with this and what made you think to compare to Tomato sauce to session replay for example? >> There are a few things I think kind of by design we wanted it to it had to be different. So kind of our grand theory of billboards was how interesting your brand is. If your brand's normally here, everyone's a bit more interesting on billboards. Like if you just look at companies seem to come out of their shell a bit more on billboards than they do on their websites. >> Why do you think that is? >> I think they're trying to stand out basically, but I think it's a bit like, again, this is going to sound harsh, but I think it's a bit like watching like a first grader play football where they're going to dabble. Um, but like they're starting from a base of being a first grader where it's like, well, we're already pretty weird online, so our billboards need to be bizarre. like they need to be like totally out there. So, we should like lean harder into this, which we think will work because the whole point is like it has to stand out in the environment and we need people to we want people to talk about and see it and we're not trying to get conversion like it's you're unlikely to decide to install like our SDK whilst you're driving your car down the freeway. Instead of trying to please everyone, we're not going to care about conversion. We are just going to try and raise awareness. And then the other thing I think that had struck us was from actually doing a bunch of social stuff, we're like, "Oh, I can like spend the time to write a useful post based on something we're learning and that will work reasonably well to get some like if it's helpful, people will share it." But somewhat depressingly if we write like if I just write something I think is funny, it can sometimes go a thousand times further in terms of reach. So if I'm just trying to raise awareness, it has to be funny. Um it and that's actually the primary thing we want to get across and and so yeah we just really wanted to like crank as far as we could over on the like weirdness slightly funny scale. Um it is a real skill. I think we've been trying very hard to I think a lot of corporates or whatever do like corporate tryh hard and it's very hard to not come because you're obviously trying hard. >> Your stuff is almost a parody of corporate try hard. You've transcended corporate tryh hard. It's a very um like on hacker news for example people talk about like on hacker news it's like troll by fire basically where there's unbelievable level of criticism our marketing channel in slack is like that too where people like your joke is just not funny um it has to be better this you look like you're trying so it's with a very um heavy feedback culture in marketing. >> Let's let's talk about that. So before um a post hog uh tweet or billboard gets out into the wild >> what is the incubation? Yeah, it's a very small number of people will be involved like probably like three or four and it is a very high trust direct place and so we're really trying to get something that we think is genuinely it might be sarcastic but something that's genuinely funny to get onto a billboard um or genu like just something that's that would make our laugh or that we would want we are kind of doing them for ourselves like is it something I think would be quite funny to see is sort of the bar it feels like you're competing against B2B software because like there's all these like AI billboards that are quite similar to each Um, but I think the reality is if you want people to pay attention, it's like no, you're competing with like what they're listening to on the radio or what they're doing on their phone or whatever else. Um, and so the bar is so many times higher. Um, so it's like it needs to be like in the at least in that realm. Um, it's not just about being like doing a slightly better incrementally better job than other software companies and which is like impossing as Mr. Beast or something, but like the mentality is like oh I wish we need to be playing that game at least a bit more. Um, we felt that, um, we would make fun of adverts in general and so we thought like, okay, we'll do like a very like Americana style >> That's right. >> ad, but we'll make it like it's like a 1950s thing, but for like AI software, whatever. >> Tastes better than spaghetti. >> Yeah. >> And you're done up here like the host of a um like a 1950s food show. >> Yeah. >> Uh, talking about your B2B B2B SAS product. Okay. And so why why 1950s Americana? Like what where was the appeal there? Yeah, I think if you sort of say like what's the most stereotypical kind of billboard ad you'd imagine. I think you sort of would imagine you would go back to like what's the origin of billboards? That's almost when you look at them from a positive perspective. I think of like oh like back in the day ads were kind of cool. They're like funnier, better thought out whereas now they've just got a bit death to humans. >> Yeah. Yeah. Or it's just like big words on a billboard with like no design element to it at all. And we thought like actually let's try and make something that's kind of a little bit like warm feeling um and pretty stupid like I was wearing like a frilly frock. >> And what about the decision to put yourself in all the ads? So, I was like, I don't they don't even realize this is me or they think they've got some like random middle-aged guy to turn up these ads. Um, either case is probably fine. Um, yeah, we did a lot with hedgehog. We did do some with hedgehogs as well, but we felt again it's just not quite as >> edgy. It's hard to make it not feel like too professionally >> done almost where it's like kind of kooky to have like >> a very average person on the ads or whatever. Um, instead of like something that we could clearly put tons of time into. >> Too hard on yourself, James. Uh, I mean, I agree. Like, I think these are great. My wife gives me so much grief. I get so excited every time I see a post dog ad around the city and my wife is like the spaghetti guys again. But it lets people know that someone's home. Yeah. >> That there's actual people behind this and that they really care a lot. You know, even things down the details in the typography like it sends a message. We are going to make a product that's also this well thought out and it's also trying to get you what you need to the same level. >> Yeah. I think that's just like a level of um signaling that like you know what you're doing to pull off an ad like this. Um because it I know it does show a level of savviness like the website is similar in thought process of like we're trying to demonstrate someone who isn't yet using our product that oh no they kind of get technology or they like kind of just get me as a person a little bit better than like a faceless corporation. Let's talk about your website. I think you've got the best website of like any B2B company maybe in the YC portfolio and I get in trouble for saying that but it's incredible. Your website's awesome. What was the genesis of going in that direction? cuz it wasn't always like that. You mentioned a little bit ago that early on you guys had a lot of back content, a lot of lore on Post Hog early on, but the website itself was still pretty typical um static website with some information for a SAS company. But now it's this whole experience simulating, you know, using a computer in post hogland. Where did this come from? >> I think a few things. I think we kind of since like 2021ish, the website's our sales team. like there isn't a single customer that won't go through the website before they buy >> the product and especially because of nature our audience. We're very self- served and so like well we should invest in this like it's that we don't have to hire a sales team it turns out in the first few years or we we had but it was tiny kind of like two people and so well I think it we can therefore justify spending like a ridiculous amount of effort on the website. The cost isn't that high but like we can put it's kind of the energy really because I think this will make us stand out. So I think a lot of people quickly 8020 something you can extremely quickly get to a polish website now like in a day you have a polish website. So everyone just does that and they're like cool I'm done now this is 8020 they move on and I'm like well like marketing to me is like because we're in a busy industry it's about standing out and so there's no point doing 8020 like there's it's just a missed shot. It's like actually all the respect on the website has come from like the last percent of effort where it's like no we're going to go like so insanely far past what is normal that it is remarkable which means that people will talk about it. Um because when we talked to users early on it turned out all of them are coming to us for people were showing up because they'd heard about us online or someone recommended us. Um and then we said why did they recommend you and it was all the tools in one low pricing um develop a brand and very technical support people >> and we have literally just done those things and but it's like okay we can't just keep doing them as it is we should be trying to >> crank the dial up further so it's like instead of building like three products we should build like 300 products um how could that work um or on the brand side it's like okay post is kind of weird it's like it needs to be weirder still like it needs to be so weird that it polarizes every day we'll get a whole bunch of people talk about that website and we we monitor all our brand mentions online and it's going to be like either this is literally the best thing I have ever seen and we also get this website is atrocious but we feel like we're polarizing it largely in favor of our audience more like I'm sure there are some people who are like what um but we're happy to >> push so hard in the direction we think is something cool for our audience that the people that aren't really our focus are going to we don't care if they disproportionately hate it basically and then partly the other thing that phenomenon that was happening was it didn't just come from like a pure aesthetic perspective we genuinely were trying to out how do we build a website that fully documents and prices for like 15 or 16 products. But we also have a whole load of other things we built that we think are useful. So for example, we have a cool developer jobs board. It's like a jobs board where the filters instead of being just like location or pay range or something are like what kind of laptop do I get? Is the majority of the company developers? The stuff that an engineer actually would be interested in think about. Yeah. Yeah. And we reveal this as like kind of a fun project, but we're like well this is useful to our audience. We have that in there. We have like a handbook that's quite popular for people to read and learn from. like we you can learn how everything works like how much we pay people like when we let people go like everything is there and so that's like another thing we have a newsletter with like more than 100,000 subscribers that's also in there and so it just felt like the form of a website of just like a thing lots of pages you scroll through it felt like we're doing something more multi much more multi-dimensional than that that was yeah it's the two things it wasn't purely aesthetic it was also from experience but we actually thought it would be better reflect what we're doing post is quite a complicated company like again it's tempting to be like okay we should just have like a single landing page we're like one button you click and nothing no other information. It's not what our audience wants. >> You're kind of like spitting in the eye of the idea of a funnel. Um it's almost like instead of a funnel that you're trying to push people through, you're just giving them a great piece of cheese >> to dig into and enjoy and savor. Well, we were wondering what would happen to conversion rate and we were like we kind of knew this is going to tank the conversion rate is going to get we like this get much more traffic and the conversion rate is going worse. And I was like, well, like if we ongoingly had way more traffic and a worse conversion rate, I if I could like double our traffic and half our conversion rate, I would take that. And so we launched it kind of knowing that's probably what would happen. But we did also think like we think this is interesting enough that people will actually switch on for once online rather than just like sort of like trying to rush to get to the button. And like we also thought like I mean if a developer can't work out how to click get started when there's already like three of them on the page like you know that marginal person who maybe would have would not converted like I don't know. It just felt like you're playing like a weird game trying to appeal to that user. And so we think like of the marginal user, this will impress enough that they will convert despite the fact the conversion experience is very unusual. >> And so yeah, the conversion rate did uh it didn't actually tank. It was like 10%ish off the top of my head. We're going to do a post on it. It was worse. Um we did like one experiment to change the flow slightly. Now the traffic's much higher. The conversion rate is significantly higher too. Um so it's performing better um from a conversion perspective even though it's like wildly complicated. My favorite part of the website, you have this uh unhinged merch shop that has some some deep cuts in it. And my favorite of the deep cuts is um visitors can buy a signed photo of James and Tim, the founders of Post Hog, and it's sold out. Someone actually came and bought >> I think we sold one. So, in fairness, I I love the yacht rock aesthetic of the photo, by the way. >> Yeah, we've had quite a few voting um off sites. This is supposed to represent Tim alignment, but I I was thinking about it on the way here and I was actually think I think the reason that feels funny is you go like this is represent Tim and I being aligned and close together, but this is what aligned would be >> we're close but something else this. Yeah. >> All right. Well, um thank you so much for spending time with us today and talking us through all this. Uh I know we have so many folks out there that follow um you the videos that we put out there looking for ways to break through. Yeah. And I think your point about like you have to be remarkable uh is obvious but overlooked so much today. And so thank you for sharing some of the ways that you guys have figured out how to try to stand out and be remarkable. And congratulations again on this latest round that you guys just raised. We're so happy for you guys excited here at YC. >> Yeah, thank you. Yeah, it was u monumentally important to us to go through the program. Um so um yeah, turn if you're listening like go apply to YC. >> All right, thanks for joining us today.