The Exchanges

Q Can I be blunt, dude? We obviously did a show a couple of years ago, and I remember when you started like your own thing, you were doing some boring shit in finance. And I remember the first round going down and I was like, I love JD, but it's pretty boring. Um, what was the pivot?

A I mean, we, we, so we've spent a year building an AI tax company, like business tax prep with AI, and we just, we got to some product market fit, but not enough where it was going to be a success. Like that's, you know, there's a thing, like the truth is we failed at building a business that would be a great business. And yeah, after a year, we were like, we got to reset. And we spent three months kind of in the wilderness trying to figure out what we wanted to do. And one of the, One of the areas we just looked at is why has no one built AI that operates out of email? Just there's so many people in the world who run their business and their life out of email and calendar. We were like, why no one, why has no one built a great product there? And it was just about the time that like Opus had gone fully agentic, right? This was like November, December last year. And so it was also the same time that models could start to actually do real work, not just do like a few steps, but really agentic work. And the prototype, we built a quick prototype in a couple of weeks and it had product market fit almost immediately. Um, so that was the pivot. It was very lucky. There's no, you know, we didn't go talk to like a hundred customers and take their notes and, you know, we built for ourselves. And, um, I think it was one of those where the technology was changing so that what we wanted to d…

AI assessment note: “we spent a year building an AI tax company... so that was the pivot.”

Q How do you advise founders in terms of hiring ahead of time? You spoke about the best engineer there for your business. Often VCs are claimed to be able to show the problems before they become problems and help you hire ahead of time. Do you think founders should hire ahead of time or actually it's hiring for the here and now?

A I think I've changed my mind on that. I think for ICs, very early on, like first, like, 15 people, you want to hire for the here and the now, you want people who are hungry, who can solve the problems you have right now, because you're trying to get and expand your, the amount of product market fit that you have and the amount of product momentum. I think at most companies, the advice that I give is somewhere between 15 and 30 people, things will break on the management side, and the problems that you encounter are not cutie cutter. Like, you can't, Ask someone who's grown a company to 200 and ask and give you a roadmap of the changes they had to make and be like, those are the changes I'm going to have to make. No, because every business pretty quickly ends up looking different. So at that point, what I generally say is like, hey, you need to hire your first few managers and your first head of, like the first person who's kind of going to grow your product team or grow your engineering team. And I think there, there, there are two choices you can make. One, you can hire what I call the four year candidate. The person who's run like a 75 to a hundred person team. So they're going to come in at 20, and you're going to be, as a founder, you're going to be like, cool, this person is going to be able to grow us for a while. They're smart, they're a problem solver, they'll get in fr…

AI assessment note: “I think for ICs, very early on, like first, like, 15 people, you want to hire for the here and the now”

Q What's been the biggest career bet you've made that didn't work out?

A I was in tech and then I was a lawyer for four years and I went back to tech. I learned a lot, but you know, four years of your life is a quite a long, quite a long time. So that's, that's definitely one. And then when I was at Dropbox, I was responsible internally for kind of trying to build a Slack like product, basically a product that would allow communication on top of like the documents that are in, in, in Dropbox. And we just, we really, really didn't figure that out. Like that was like big flop. I think we were too far from the customers. There's a ton of stuff in terms of like early product that I, I got way wrong on that one. I learned a ton from it.

AI assessment note: “when I was at Dropbox, I was responsible internally for kind of trying to build”

Q Why don't you just go fuck it, burn the bows?

A It's a, it's a good question. And I, I think I, I would be lying if I said there aren't Mornings where I wake up and I think about it. I believe that to prove value on the business side, you must make your customers pay. So I do think there might be a world where our, where the PLG part is much more subsidized, but as soon as you get three to five team members, I really want to make money on that side. I really want to make sure I'm delivering value. I'll give you a story. We, we, when we launched the product initially, Right. For the first five months, not launched, but we were like in private beta and then we opened the beta. We didn't have pricing. Okay. There were users who were spending a shit you not like 2000 dollars of compute a month, 4000 dollars of compute a month. There's someone on the platform who'd spent in five months was like 26,000 dollars.

AI assessment note: “I believe that to prove value on the business side, you must make your customers pay.”

Q So what is the future interaction between human and agent? And what I mean by that is, do we have, like, a consumer agent, an enterprise agent, and then a hardware agent that does maybe productivity and notes? How do we think about that multi-agent versus single agent?

A Each human will have one, two, maybe three entry points into the, into the digital space, because I don't think you'll want to be like, oh, I'm doing sales. Let me use the Salesforce agent. Oh, I'm doing project management. Let me use the linear agent. Oh, I'm doing this other thing. You'll want one entry point. You won't want to ask yourself the question. You just push a button and you start speaking. But there are real reasons why it may be more than one, and it has to be. So one of them is just privacy and how your workplace is going to feel about their data being intermingled with your personal data, right? So I think you, you might still have only one hardware entry point, but from a privacy perspective and from a, like, where your data lives, I think you're going to always want to separate on the data layer your personal and your work data. And in town, we do that for you, but I think it could be two different companies that you end up using, right? Uh, like one layer, one layer below, but I think privacy is the main deter will be the main determinant of your data silos and, and your company, whoever you work for's desire to own the data that you create for them, right? They won't want that to intermingle with your personal, but from a usability perspective, like it's just on my phone, it's annoying that I have 55 apps and I'm clicking everywhere. And so if you move to a …

AI assessment note: “Each human will have one, two, maybe three entry points into the digital space”

Q How important is time to wow or time to user delight?

A I mean, yeah, I think the only reason our product works today, honestly, is we have very low, very low time to value for a single user. And so what happens is single users like the product, even for some, you're talking about like meeting briefings and kind of naysaying, but coming into a meeting really fucking prepared, getting the action items from the meetings like automatically handled for you is for a lot of, for a lot of roles like sales, recruiting, small business owners is like magic. So the fact that with us, no configuration, you get out of the box, it gives a magic moment. Then the user is like asking questions. What else could I do with this technology? That's for us all the, like our focus is on getting that right. Can we give you time to value there really quickly? And then we play the longer game on all the other integrations. And for us, that's working really, really well.

AI assessment note: “the only reason our product works today, honestly, is we have very low time to value”

Q Can you help me understand Apple's agent roadmap?

A I think the problem for Apple is twofold. One, they're not a cloud company. They're just not, it's just not their DNA. They don't know how to do cloud. And the reason why that matters is because What we talked about earlier. Agents are better the more data they have. And the data is not all on the phone. And, and so the fact that they're not cloud is like one big issue. The second issue is they've like contorted themselves for competitive reasons around a privacy and on device story that is like Absolutely, like, puts them far away from the frontier. Like, local models on the phone, it's amazing, but they're just not, they're just, it's just slower and dumber, right, than what's at the frontier. And so, as long as they're committed to this, like, on-device, like, privacy-preserving stuff, it's, the privacy stance is good from a human perspective, but they've tied it too much to the on-device. So the, not being good at cloud, Then being on device, and then from the privacy standpoint, making it difficult even on the phone to interoperate with all the data that they have, it just, it's, those are a lot of disadvantages to play with. Now, you know, at the same time, they do have the devices, so the new Siri, right, is going to be much, a much better personal assistant than the, I mean, that's rumored, but you know, you know people who've tried it, so when you're in the Valley, you…

AI assessment note: “so the new Siri, right, is going to be much, a much better personal assistant”

Q Is that that insightful? ChatGPT is always like, here's all the things that we want from you, and I'm like, no way, no way. Read, write, email abilities, no.

A I think, well, I think their suggestions are, I think their suggestions are just like plain bad, to be honest, but they didn't even have suggestions until a few months ago. The delta is this. If you want to use ChatCPT, you don't have to connect your email. They just don't force you to do it. They ask you a bunch of times to do it now because they realize the value is helpful. But the base experience, they're trying to show someone normal. Hey, you can have value in this product just because you have a chat box. And that's how most people experience it. Our approach is more like, listen, you have to connect email and calendar. You cannot use our product if you don't do those things. But if you do those things, we can do all this magic for you, right? Here's what we know about you. Here's work that you normally do. We'll recommend automations that automate that part of your work. That's the, that's the part where people are like, oh, that's really cool.

AI assessment note: “I think their suggestions are just like plain bad, to be honest”

Q Well, I'm about to extract a decade of knowledge. So I think I'm the one winning, but I want to start with your career. And I think careers are often made actually with more singular moments. So when you reflect, what would you say was the single biggest break in your career and how did it impact your trajectory?

A That's a good question. I think, look, I think, objectively, the answer would have to be joining Plaid as, you know, to lead engineering, um, which was about six and a half years ago, just because I joined when the company had, you know, forty-ish people and, you know, less than ten million in ARR. We've had, we've had a crazy trajectory, and it means, like, in terms of my career and my ability to be successful long term, I have a lot of options now that I never would have had if I hadn't Join Plaid, but actually it's not joining Plaid is not what I consider the, the lucky break that I had. That would be joining Dropbox, which was my first job, like truly in Silicon Valley. Um, so before, before Dropbox, I kind of had a weird career. I'd worked in tech for a bit, then I'd been a lawyer for a bit. Then I'd helped a friend kind of grow a company like a FinTech company in New York, but more on the hedge fund side of things. And I hadn't had like what you would call like a triple A employer on my resume. And I was smart, but you know, I was kind of a weird outsider with, you know, a little bit of an attitude. And I realized at some point that if, if you want to be an engineer and you want to do great engineering work at the time, at least I felt like you had to move to Silicon Valley. And I was in my early thirties. You know, I don't think I'd had a great success and I knew a frien…

AI assessment note: “That would be joining Dropbox, which was my first job, like truly in Silicon Valley.”

Q How do you advise founders in terms of hiring ahead of time? You spoke about the best engineer there for your business. Often VCs are claimed to be able to show the problems before they become problems and help you hire ahead of time. Do you think founders should hire ahead of time or actually it's hiring for the here and now?

A I think I've changed my mind on that. I think for ICs, very early on, like first, like, 15 people, you want to hire for the here and the now, you want people who are hungry, who can solve the problems you have right now, because you're trying to get and expand your, the amount of product market fit that you have and the amount of product momentum. I think at most companies, the advice that I give is somewhere between 15 and 30 people, things will break on the management side, and the problems that you encounter are not cutie cutter. Like, you can't, Ask someone who's grown a company to 200 and ask and give you a roadmap of the changes they had to make and be like, those are the changes I'm going to have to make. No, because every business pretty quickly ends up looking different. So at that point, what I generally say is like, hey, you need to hire your first few managers and your first head of, like the first person who's kind of going to grow your product team or grow your engineering team. And I think there, there, there are two choices you can make. One, you can hire what I call the four year candidate. The person who's run like a 75 to a hundred person team. So they're going to come in at 20, and you're going to be, as a founder, you're going to be like, cool, this person is going to be able to grow us for a while. They're smart, they're a problem solver, they'll get in fr…

AI assessment note: “first 15 people you want to hire for the here and the now”

Q You mentioned some crucial, crucial topics there, which I do want to discuss because we touched on them a little bit before. One of them, which I'm actually very passionate about and not in a friendly way either, but it's the in-person versus remote versus hybrid. Um, talk to me about how you think about this and do we have an opinion here?

A One opinion I have is we've talked too much about it. So there was, I think I spent A lot of the last two years in the CTO dinners where we, or CPO dinners, or president dinners, or whatever, VC dinners, you name them, and we would spend half of the time talking about what we're doing. When are we returning to office? Are we not? Are we, are we hybrid? Are we remote first? Are we moving back to in office? And when I say it doesn't matter, I, I think I think there are plenty of really successful companies before the pandemic that were really going hard after fully remote first. And it worked for them because they had a, the people who went to work, there were people who want remote first. What happened in the pandemic is we forced people into working models that maybe they didn't like. So on my team, I have people who like remote first and I have people who want to be in the office because I didn't pre-select in my hiring criteria, like a specific persona. Now you kind of make a decision. And I'm not saying it doesn't matter, but again, I don't think it's the difference between success and failure. You make a decision, you make sure your hiring and your culture matches the decisions. There's a few areas where I think you should be careful. So I'll give you an example. Highly creative, fast moving work where you're not sure what the requirements are and where your customers are l…

AI assessment note: “I think in person is better because I think you collaborate more effectively.”

Q then fuck them. I'm so enjoying this. So two questions I thought on the negotiation pre-joining side. One of my biggest lessons is when people are really difficult on the title. I want chief of staff, not EA. I want head of engineering, not VP of engineering or whatever that title. It's never a good hire. Do you agree and have you felt the same or actually am I wrong?

A Certainly the most of the environment environments I've worked in, we try to be kind of low ego, low title. We want the best ideas to win, not just the most seniority. So even at Plaid amongst ICs, for example, there are no titles, even in managers outside of the person who leads like a giant area, we have don't, we don't have directors and things like that. So I've been very much in the, like, It's, it's not a red flag, but it's a little bit of yellow flag when people really care about those things. The, the flip side of it, which I think is, is really, really important is It actually, it matters in the industry and you can never fully divorce yourself from the industry, especially when you get to a certain size, right? When you get to like a thousand people, 2000 people, you're going to recruit people who have titles. You're going to recruit people for whom titles matter. So like a, like a thing for you is, um, there's bias and unfairness in the industry, right? And so there's some underrepresented groups for which being a staff engineer on LinkedIn It's truly meaningful career-wise. It, you know what I mean? It, it, it matters not, it's not about ego, right? It's a, it's a, it's a, it's about this feeling that the industry hasn't, like, done right by you, and, and when you achieve this thing that is truly meaningful, you wanna, you wanna celebrate it. So I think at scale, wh…

AI assessment note: “It's not a red flag, but it's a little bit of yellow flag”

Q your company, you know, it's all about mission and vision. That doesn't sell. That makes people dislike you. The truth like that is what makes people like you. My question to you is, I suck at firing so much so that I've had my COO fire people because I don't want to do it. How, what does being good at firing mean? And how can I get good at it?

A It's like having a breakup. No one ever likes doing it. I don't think you truly get good at it. And I don't think you ever have a playbook where both sides come out of it like super happy humans. That's just, that's just reality. So the first thing you got to realize that when I say good at, I actually don't mean the conversation with the other person. I mean, identifying at the right point in your company that the odds of success of that individual and the role is no longer right for the business. Because if you can look at someone in the eye and, and you're convinced yourself that it just doesn't make sense for the business. You've given a shot to prove, a shot for them to improve and prove themselves, and they haven't. You're just doing what's right for the business, and they will understand that, and they will respect you for it, even if they don't like you in the moment, and they don't feel like it's fair, because they're shareholders. They joined a startup. They understand the risk. They understand it's, it's a very, very difficult job. I just think that's how you have to treat it, right? There's a human level where, you know, how you deliver it, how open you're in communication, that those things matter, but at the end of the day, it's, It's about what's doing right for the business. Probably the biggest mistake is not giving feedback.

AI assessment note: “when I say good at, I actually don't mean the conversation with the other person”

Q It's just, it's just true. Um, I totally agree. Um, I do want to ask one final one on people, and it's just a question around, do you believe that you can be truly great and have work life balance? And when I say truly great, let me put a placement around it. Build a ten billion dollar plus company. I don't.

A Well, so I know a few truly great people who I think are, have the right viewpoint and are really good at motivating and delegating, meaning they create the structure for success, like the North star, the product roadmap, and then they're able to motivate other people to go in that direction. So that person can do it. And that person could be a great CEO. Like it's, it's possible, but as a whole, no, you need, I think to, to do great things, you, you, There's a, there's a great sacrifice. You'll find exceptions like one offs, but I think on average it doesn't play out. And the analogy that I would say is to like a professional, a professional athlete, like a LeBron James or whatnot, there's plenty of people who are professional athletes who from a pure physical understanding of the game, they're there and who just don't put in the work. And there's people who put in the work and with athletes, we're totally okay to make fun of the ones that don't put in the work, right? They get like the, the, the sports writers, like, Just, like, make fun of them all the time. They're like, ah, it's a 15 year career, you get one shot at this, like, you get your big payday, and then you stop trying as hard. Right? They, like, love digging into them. But, like, what's the difference? You know, we're like, oh, the athlete's career is so short, you know, so, so, like, they shouldn't, they should w…

AI assessment note: “as a whole, no, you need, I think to, to do great things”

Q then fuck them. I'm so enjoying this. So two questions I thought on the negotiation pre-joining side. One of my biggest lessons is when people are really difficult on the title. I want chief of staff, not EA. I want head of engineering, not VP of engineering or whatever that title. It's never a good hire. Do you agree and have you felt the same or actually am I wrong?

A Certainly the most of the environment environments I've worked in, we try to be kind of low ego, low title. We want the best ideas to win, not just the most seniority. So even at Plaid amongst ICs, for example, there are no titles, even in managers outside of the person who leads like a giant area, we have don't, we don't have directors and things like that. So I've been very much in the, like, It's, it's not a red flag, but it's a little bit of yellow flag when people really care about those things. The, the flip side of it, which I think is, is really, really important is It actually, it matters in the industry and you can never fully divorce yourself from the industry, especially when you get to a certain size, right? When you get to like a thousand people, 2000 people, you're going to recruit people who have titles. You're going to recruit people for whom titles matter. So like a, like a thing for you is, um, there's bias and unfairness in the industry, right? And so there's some underrepresented groups for which being a staff engineer on LinkedIn It's truly meaningful career-wise. It, you know what I mean? It, it, it matters not, it's not about ego, right? It's a, it's a, it's a, it's about this feeling that the industry hasn't, like, done right by you, and, and when you achieve this thing that is truly meaningful, you wanna, you wanna celebrate it. So I think at scale, wh…

AI assessment note: “It's not a red flag, but it's a little bit of yellow flag”

Q You mentioned some crucial, crucial topics there, which I do want to discuss because we touched on them a little bit before. One of them, which I'm actually very passionate about and not in a friendly way either, but it's the in-person versus remote versus hybrid. Um, talk to me about how you think about this and do we have an opinion here?

A One opinion I have is we've talked too much about it. So there was, I think I spent A lot of the last two years in the CTO dinners where we, or CPO dinners, or president dinners, or whatever, VC dinners, you name them, and we would spend half of the time talking about what we're doing. When are we returning to office? Are we not? Are we, are we hybrid? Are we remote first? Are we moving back to in office? And when I say it doesn't matter, I, I think I think there are plenty of really successful companies before the pandemic that were really going hard after fully remote first. And it worked for them because they had a, the people who went to work, there were people who want remote first. What happened in the pandemic is we forced people into working models that maybe they didn't like. So on my team, I have people who like remote first and I have people who want to be in the office because I didn't pre-select in my hiring criteria, like a specific persona. Now you kind of make a decision. And I'm not saying it doesn't matter, but again, I don't think it's the difference between success and failure. You make a decision, you make sure your hiring and your culture matches the decisions. There's a few areas where I think you should be careful. So I'll give you an example. Highly creative, fast moving work where you're not sure what the requirements are and where your customers are l…

AI assessment note: “I don't think it's the difference between success and failure.”

Q Can I ask what's been the hardest thing about the product build that you maybe didn't expect?

A The speed of the market is insane, Harry. I've never seen anything like it. Before, in the past, you know, you, you, you talk to customers, you build a feature, they would use it, and you would be, like, learning from that feature, and the learnings would go into the next feature, and the next feature, and then eventually someone would copy your first feature, but then you had, like, your three learnings ahead. Do you know what I mean? You'd been able to, like, Use your product market fit to generate more product market fit. And, you know, for startups, usually you're like milking these, these, these user insights for a really long time. Eventually you run out of user insights, but that would take like 10 years, right, to happen. So you have this entire period where you can, you can just because you're number one or number two in a market, learn more and iterate, right? And it's really, it's really good. The problem today is it is so much faster to build that as soon as something is working for somebody, Everyone notices and is able to get there within like two weeks or four weeks, like copy really, really fast and learn. You can only learn at the speed of humans. Do you know what I mean? You can build now at the speed of machines, but you can only learn at the speed of humans. And so you're, I'm not able to extract quite as many learnings as, you know, that allows me to get to…

AI assessment note: “You can build now at the speed of machines, but you can only learn”

Q Why are you really stressed out about it?

A It's just, I think it's the percentage of tasks that are frontier. Because on everything else, I can imagine getting the prices down. But, you know, the thesis that I just said before is, over time, there are more ways to use AI to generate more revenue for a lot of companies. The implication there is, it's like, there's like things at the frontier that generate more revenue. And the problem with the frontier is, I have zero pricing power at the frontier. And I mean, I think this is what happened to Cursor, right, at the end. It's like, you can have huge market share and customers love you and everything, but if you're, If you're paying your suppliers and competing with your suppliers at 70% margin, eventually it gets like a little bit difficult. And so, you know, the, that, that is the part that I'm worried about, the end game. If we are, but again, I have lots of ifs. I have to get to tens of millions of users. They have to be paying. I have to have a lot of scale. And then I'm like at a place where I'm still competing with my suppliers. I'm still competing with OpenAI and Anthropic, and I'm just giving them money for the 20 or 30% of workloads that are at the frontier for me. And that's what makes the economics not work. That's the, that's the part where at the end of the game, I need some, I need some solve for that by then. I don't need it right now. The reason that's the …

AI assessment note: “the problem with the frontier is, I have zero pricing power at the frontier.”

Q You are competing with your suppliers. I mean, like Astra, you see, you see as a direct competitor, correct?

A Totally. I am today. A hundred percent. I am today. Yeah. But the percentage, the percentage that was a face, the, I mean, I am competing with Astra, but there's still the, the, it's the open box problem. You would be shocked at how many people just don't know what AI can do. Right. It's like, the problem is, Having a product experience that gets a normal person to get value out of AI is really hard. That's why when people use town, they like it, and then they start paying for it. Like the, the, the, the payment rate for us on acquisition is like more than 15% of users who try the product end up paying for it, which is extremely high for PLG, because the value delivered relative to what they were getting out of ChatGPT is just huge. Yes, I'm competing with.

AI assessment note: “Totally. I am today. A hundred percent. I am today.”

Q How does that compare to Dropbox? Cause Dropbox must have way more than ten million users.

A You have to have the growth, right? It couldn't be, I couldn't terminal a 10, right? I'd have to believe that I can keep getting a good rate of growth. The problem, I mean, I'm pretty far from Dropbox. It's been a long time since I worked there, but I think there was a huge free, huge pack of free users that were very costly on the cost side. And then on the paying side, I don't remember if the number was like 10, 20, thirty million, but it did, You know, I did flatten out at some point and there was no way to generate more revenue or growth from the users. I think what's different on the AI space is like, I think you should be able to, as you do more, like once you have a company on a platform using your platform as the core part of where AI works happen, you can, you, you should be able to generate increasing revenue as, as the token spend goes up.

AI assessment note: “I don't remember if the number was like 10, 20, thirty million”

Q your company, you know, it's all about mission and vision. That doesn't sell. That makes people dislike you. The truth like that is what makes people like you. My question to you is, I suck at firing so much so that I've had my COO fire people because I don't want to do it. How, what does being good at firing mean? And how can I get good at it?

A It's like having a breakup. No one ever likes doing it. I don't think you truly get good at it. And I don't think you ever have a playbook where both sides come out of it like super happy humans. That's just, that's just reality. So the first thing you got to realize that when I say good at, I actually don't mean the conversation with the other person. I mean, identifying at the right point in your company that the odds of success of that individual and the role is no longer right for the business. Because if you can look at someone in the eye and, and you're convinced yourself that it just doesn't make sense for the business. You've given a shot to prove, a shot for them to improve and prove themselves, and they haven't. You're just doing what's right for the business, and they will understand that, and they will respect you for it, even if they don't like you in the moment, and they don't feel like it's fair, because they're shareholders. They joined a startup. They understand the risk. They understand it's, it's a very, very difficult job. I just think that's how you have to treat it, right? There's a human level where, you know, how you deliver it, how open you're in communication, that those things matter, but at the end of the day, it's, It's about what's doing right for the business. Probably the biggest mistake is not giving feedback.

AI assessment note: “when I say good at, I actually don't mean the conversation with the other person”

Q As an investor today, every company in some respects is questioned about how How cannibalized could this be from any of the big providers? Um, this is like right in the motherfucking sweet spot. Just to be blunt. Like, how do you want, and we've got GrokBot in the most recent times. How do we think about cannibalization by frontier model providers and GrokBot in recent weeks as a threat?

A You want to know, the truth is I know what I'm building is a top three priority at Google and Apple, like in the next 12 months. Not a top 10 priority, like a top three priority. So, you know, I, when I go to sleep, I fall asleep very quickly. It's one of my superpowers, but I do wake up at like three in the morning and immediately, usually when I wake up, like some dark thought goes into there and it's, you know, it's like roulette when you're a founder, like which dark thought will stop me from falling asleep again. And definitely the, ah, this is gonna be, you're like in the middle of the fairway and everyone's trying to, you know, is gonna try to get you. That's a hundred percent the fear, but I gotta, I gotta say this. You won't talk about modes, right? You're like, what's the mode? What's defensible? I, I think talking about moats is a little bit of a luxury and you have to be more successful than town is today for it to matter. So just like, I will answer your question, but like my mindset right now is how do I get a 100,000 or a million paying users in a market that has like a TAM of a billion potential, you know, paying users. Step one is like, you need, we have to have really deep product market fit. And I think none of the products today actually have really deep product market fit yet. Like Grokbot's really cool. It's awesome, but it's a power user product. It's not…

AI assessment note: “talking about moats is a little bit of a luxury and you have to be more successful”

Q On the network effect side, have there been any interesting lessons or observations? What have you learned on expansion from wall to wall?

A So first of all, interesting aspect for us of network effects is if the company has one person who is a tinkerer and who starts to build things like team skills, team integrations, team routines, that is like building, those are all building blocks on town that everyone on the team gets for free. Then we'd send to see a lot more adoption faster. And it's, it's interesting, right? Cause I'm, we're trying to build a product that doesn't require the tinker. Right? Because for the single player experience, we want you to be onboarded and get a ton of value, right? And if you're a real estate agent, you have automations that are real estate agent specific. And if you're a salesperson, you get automations that are salesperson specific. We're trying to give that, that experience to you out of the box. But what happens is if there's a power user that's next to other users, they find ways to make those other users much more successful. And I think you'll find that with a lot of AI products, right? So one of the, one of the predictors actually is, is there A tinker on the team. So one of the questions we ask ourselves a lot is can we identify those folks and can we make it easier for them to create virality for their other team members? Um, and then the second observation is there are a lot of functions that are underserved by AI within companies, even enterprises. So I'll give you a ver…

AI assessment note: “interesting aspect for us of network effects is if the company has one person who is a tinkerer”

Q To what extent is GrokBot's integration into X a feature or a bug? Because to some corporates and to professional usage, It could be concerning actually the interaction with the social.

A Well, I think they have, I think brand for them. I think some people just won't want to touch it because of brand. And it's like, that's just inevitable. And it's, you know, that's just a thing that they're going to have to deal with forever. Um, but from a distribution perspective, uh, and I think for some segments, I think in early growth, it is probably quite useful. I think a person on X that uses these products is not actually product market fit. Meaning that those are not the mainstream users and you have to keep that in mind. And I, by the way, I think they think about that Over at Grogbot all the time, but I don't think they think winning the power user slash influencer on X is where the market is. That is not where you win the market. That's the early adopter market, but.

AI assessment note: “from a distribution perspective, uh, and I think for some segments... it is probably quite useful.”

Q Can I ask you, when we think about usage, how do you define a successful user?

A Oh, um, well, I, I just define them as someone who pays me every month. If they keep paying me, no, I'm, I'm serious. I'm serious, right? If they keep paying me, I've done my job, right? I can't think of them as the most, the more tokens they use. It's a dangerous way to think about it, because if you think about it as like, they use more tokens every month that's successful. What if they're using the tokens in a way where the ROI is less clear to them? Meaning they don't realize that they're using tokens to do things that they don't value as much. If you do too much of that, then they wake up one day and they're just paying you too much and they get mad and they turn off of the product. So I think you have to take a long-term perspective. The problem with token maxing, there's two problems in my opinion. One is like companies told, told people, Hey, you can use as much money as you want on AI, which is bad. Like you want people to think is the ROI of using AI here worthwhile. So now, you know, people are not going against employees using AI. They're going, they're like, no, no, we need incentives. So they use AI for good reason. So that's like one aspect you need to think about ROI upfront. But the second problem is sometimes it's hard to know the ROI of something like, let me be more prepared for a meeting. How much, how worth it is it to be more prepared for a meeting? For p…

AI assessment note: “I just define them as someone who pays me every month.”

Q It's just, it's just true. Um, I totally agree. Um, I do want to ask one final one on people, and it's just a question around, do you believe that you can be truly great and have work life balance? And when I say truly great, let me put a placement around it. Build a ten billion dollar plus company. I don't.

A Well, so I know a few truly great people who I think are, have the right viewpoint and are really good at motivating and delegating, meaning they create the structure for success, like the North star, the product roadmap, and then they're able to motivate other people to go in that direction. So that person can do it. And that person could be a great CEO. Like it's, it's possible, but as a whole, no, you need, I think to, to do great things, you, you, There's a, there's a great sacrifice. You'll find exceptions like one offs, but I think on average it doesn't play out. And the analogy that I would say is to like a professional, a professional athlete, like a LeBron James or whatnot, there's plenty of people who are professional athletes who from a pure physical understanding of the game, they're there and who just don't put in the work. And there's people who put in the work and with athletes, we're totally okay to make fun of the ones that don't put in the work, right? They get like the, the, the sports writers, like, Just, like, make fun of them all the time. They're like, ah, it's a 15 year career, you get one shot at this, like, you get your big payday, and then you stop trying as hard. Right? They, like, love digging into them. But, like, what's the difference? You know, we're like, oh, the athlete's career is so short, you know, so, so, like, they shouldn't, they should w…

AI assessment note: “You'll find exceptions like one offs, but I think on average it doesn't play out.”

Q Would you be, Would you be an investor in 11 Labs at a twenty two billion dollar price?

A I think on 11 Labs, like we're users of 11 Labs. I mean, I just think it's just, they sound the best. I'm not paid. I'm not an investor. It is very expensive. What I don't know is if it tops out, and that's, I think, the risk for something like 11 Labs, meaning, like, we just get voices good enough, and then you can get it. I can put, you know, open weight models on base 10 and get it, but it just doesn't feel like that right now. I just don't know how much runway they have before it reaches that, and so that's why, I'm not saying I'm bearish. I really like that company, but, like, twenty-two billion is a lot of money, and, um.

AI assessment note: “I really like that company, but, like, twenty-two billion is a lot of money”

Q What's the biggest internal product disagreement you guys have today?

A We have product market fit for like some purely personal use cases that we didn't expect, you know? And the problem is it's like, it's like what? Like families, like parents. Parents and families, there's like tremendous product market fit for town there. Because schools, you don't have kids. Right? You have, yeah, you have a girlfriend, you don't have kids. So, um, schools in America, at least, send a lot of emails, and they have a lot of, like, portals where things have to happen for sports leagues, and they're like, this kid's reports, and there's a lot of scheduling for kids that has to happen for, like, haircuts, and summer camps, and all of these things. And our products, because it's really good at email, and it's really good at the scheduling stuff, it, it really has tremendous product market fit for families. Um, and we have like a marketing, so it has the product market fit. The question is like, do we market to this group and do we spend time on it? Because it's a great group and it has a willingness to pay, but it does not have the willingness to pay of a mid-market firm, right? It's just, it's a different look.

AI assessment note: “The question is like, do we market to this group and do we spend time”

Q Where does going against the grain accelerate the business?

A I think that's very, like, business specific. My overarching thesis is that a lot of people things On a lot of people matters, how you level, how you title, how you comp, um, how you organize your org, like your manager to IC ratio, remote hybrid. It's like, pick a thing, pick one of the three options on the menu for each of those, and just like move forward with your life. I just don't think it's the difference between a good and a great business, like bad strategy, bad product plan, going to the wrong market. The efficiency gain or loss is like a hundred percent or zero percent. You know, you build the wrong product for like two years. You're slightly better at leveling people. Like, I don't know, your pulse score is like three points higher and your retention is like one and a half percent higher. Like, I just don't think that fundamentally matters.

AI assessment note: “I think that's very, like, business specific. My overarching thesis is that”

Q Guide them into like, what is best? Hey, we find best outcomes if you let them run for X.

A One way to think about LLMs, right, is they're just, they turn energy into, like, GDP, right, or into revenue. You know, like, really, you step way back, right, you know, because you power and silicon, and then you get intelligence, and we're applying the intelligence towards business results, so, you know, if they get smart enough, it just creating GDP on the other end, and so, like, you just say, like, hey, make money for me, and then let it run for a long time, and it can do whatever it want to, or do we want to live in a universe where we think the humans Role in this is actually to set the direction and like make sure that the actions that are being taken align with some kind of human value system. So I live in that second universe where I think it is the human's responsibility to first allocate the resources. That means to say how many tokens are we willing to spend to try to get a goal to set the goal right as well. So you, you set the goal and the budget and then to monitor, right? Like the, The overall shape of the actions that are taken to get the result. And how much as, as the intelligence gets smarter, you might say, well, maybe, maybe the allocating of resources you're trusting in LLM to like analyze ahead of time what it thinks the ROI is on a pretend task and tell you how many tokens you should be willing to allocate before deciding to step away. And maybe on li…

AI assessment note: “it is the human's responsibility to first allocate the resources. That means to say how many tokens”