The Exchanges

Q Speaking about who it's for that, one really striking element for me when I was going through the numbers was the You know, despite the incredible ARR, only one percent comes from enterprise. Like, how do you think about this? And is this like, yeah, that's how it's meant to be? Or is this like, hey, this is the opportunity we have in front of us?

A So we definitely think there's an opportunity there. And we have a group inside Squarespace called Channels and Services that has really started trying to figure out where we fit in enterprises. You know, they operate off of inbound leads right now. They have a sales force. And there's a number of ways that Squarespace can grow within enterprises. A couple primary ones are one, large resellers. So people who specialize in a vertical and they need to buy 305 hundred websites and administer them in bulk. And so we have tools that are just coming out that target that use case. Or it's sort of the model of how Dropbox spreads into companies where it's like, hey, you're the marketing team at pick a big company on like Nike or something like that. You know, the marketing team is, you know, strapped for resources. We need to make these event websites and these landing pages. And they start to use Squarespace, and then the larger company is like, whoa, hold on. We need to control that. We need single sign-on. We need the inventory of the sites. And it's like, okay, well, we can really help with that. So I think those are the two primary ways we're sort of moving into the enterprise use case. Or, of course, there's a large customer that needs someone to call with support, and they need to pay not on a credit card, and they want to control single sign-on for a single site. So there's a h…

AI assessment note: “we definitely think there's an opportunity there”

Q I totally get it. You mentioned COVID there, and one thing that fundamentally changed within COVID was e-commerce. I'm really intrigued. How would you say e-commerce has turbocharged Squarespace, and what does the future hold for e-commerce within Squarespace?

A Yeah, it's been an exceptionally important part of our business, and frankly, one that we've been no stranger to for a decade. You know, the ability to sell things on Squarespace has been the most requested feature for a decade. We started investing in our e-commerce platform. That's basically physical goods, digital goods, eight years ago. And over the past couple of years, what we've been focused on is, you know, we internally refer to as multimodal commerce, which is just, there are many, many different ways to sell. And if you think about Squarespace right now, we offer an incredible amount of ways to sell each with an amazing amount of depth. Yes, there's physical commerce, which again, Working on for eight years. You can sell digital goods. You can accept donations. We have a scheduling product, which was, we joined forces with Acuity Scheduling, and that powers Squarespace Scheduling right now, so you can sell time. We have a member areas product, so you can sell access to, like, you could have a private blog, private video lessons. You can combine that with our email campaigns product to do a sub-stack-like product with Joining Forces with Talk. You can do to-go ordering, reservations on Squarespace. There's just many, many, many ways to Transact. And what I'm excited about over the next couple of years is just having all of those exist within one platform and have our …

AI assessment note: “what I'm excited about over the next couple of years is just having all of those exist within one platform”

Q Speaking about who it's for that, one really striking element for me when I was going through the numbers was the You know, despite the incredible ARR, only one percent comes from enterprise. Like, how do you think about this? And is this like, yeah, that's how it's meant to be? Or is this like, hey, this is the opportunity we have in front of us?

A So we definitely think there's an opportunity there. And we have a group inside Squarespace called Channels and Services that has really started trying to figure out where we fit in enterprises. You know, they operate off of inbound leads right now. They have a sales force. And there's a number of ways that Squarespace can grow within enterprises. A couple primary ones are one, large resellers. So people who specialize in a vertical and they need to buy 305 hundred websites and administer them in bulk. And so we have tools that are just coming out that target that use case. Or it's sort of the model of how Dropbox spreads into companies where it's like, hey, you're the marketing team at pick a big company on like Nike or something like that. You know, the marketing team is, you know, strapped for resources. We need to make these event websites and these landing pages. And they start to use Squarespace, and then the larger company is like, whoa, hold on. We need to control that. We need single sign-on. We need the inventory of the sites. And it's like, okay, well, we can really help with that. So I think those are the two primary ways we're sort of moving into the enterprise use case. Or, of course, there's a large customer that needs someone to call with support, and they need to pay not on a credit card, and they want to control single sign-on for a single site. So there's a h…

AI assessment note: “So we definitely think there's an opportunity there.”

Q That is very, very kind of you, but I want to start today with a little bit of the story. You know, we see Squarespace is this incredible public market's behemoth today, but it all started in the dorm room, which I just love as the foundation story, so take me back there. What was that founding aha moment for you?

A Yeah, I mean, wow, we're talking 18 years ago now when I first started programming it. You know, my background is engineering and design And so, you know, back a zillion years ago, I wanted a website for myself, and I was very frustrated with what was out there, and I wanted something that was all in one, and back then that meant, like, page builder and photo galleries and hosting and statistics software were together. I mean, it's, like, unimaginable now. And I wanted something that was really design-centric and looked really good, and I think that, especially back then, I think we take it for granted a little bit now, but design on the web was not really a great thing, and I've always been a huge, Fan of design and aesthetics, and I wanted something to look good, so I started making Squarespace really for myself.

AI assessment note: “I wanted a website for myself, and I was very frustrated with what was out there”

Q I totally agree. It is just a very different phase of the company that you mentioned three to four months. I spoke to Eliza at NEA before, and she said, you've got to ask him, how would you personally describe this chapter of Squarespace?

A Okay, we're private for 18 years. So I would say the past couple months have been Really fascinating because the entire dynamic really, really, really does change. You've got your insiders who are holding things, and they could be concentrated or not concentrated. I think the other thing I started to realize is I spend every day thinking about Squarespace, but for public market investors, they have their own portfolio. Maybe they're looking at 70 companies, 80 companies. You're one sliver of their time, and, you know, what incentive do they have to pay attention to you right now versus, you know, let's just let a couple quarters play out and then pay attention to you then. And so it's just very, very, very different dynamic than what is happening in the private markets. It plays out every day right in front of your face, rightly or wrongly, in the stock price, which is, of course, you know, new for a lot of us. I mean, in the private markets, we did a four and nine A, we were doing it monthly, but you know, it's kind of, it's not that volatile. And so this is very new.

AI assessment note: “past couple months have been Really fascinating because the entire dynamic really, really, really does change.”

Q Can I ask? I mean, that's a misnomer. Do you think there's any other misnomers of Squarespace that people have?

A You know, for a long time, and I'm not sure it's really true today, because of our emphasis on design and on creatives, and, you know, they were sort of like, oh, well, is it just for that community? Is it, you know, we're headquartered in New York. It's just for, like, you know, artsy people in New York. And I was always like, no, it's never been for that. It's, it's been for Exposing the benefits of that kind of thing to a much broader customer base. And so, like, should a dentist use Squarespace? Absolutely they should use Squarespace, and they should have an amazingly designed website that highlights their message and gets them more business. And so it was always about bringing that, that notion of design and aesthetics to everyone, as opposed to saying, no, it's only for the people, you know, the certain group of people who really care about that.

AI assessment note: “is it just for that community?... no, it's never been for that.”

Q I totally get it. You mentioned COVID there, and one thing that fundamentally changed within COVID was e-commerce. I'm really intrigued. How would you say e-commerce has turbocharged Squarespace, and what does the future hold for e-commerce within Squarespace?

A Yeah, it's been an exceptionally important part of our business, and frankly, one that we've been no stranger to for a decade. You know, the ability to sell things on Squarespace has been the most requested feature for a decade. We started investing in our e-commerce platform. That's basically physical goods, digital goods, eight years ago. And over the past couple of years, what we've been focused on is, you know, we internally refer to as multimodal commerce, which is just, there are many, many different ways to sell. And if you think about Squarespace right now, we offer an incredible amount of ways to sell each with an amazing amount of depth. Yes, there's physical commerce, which again, Working on for eight years. You can sell digital goods. You can accept donations. We have a scheduling product, which was, we joined forces with Acuity Scheduling, and that powers Squarespace Scheduling right now, so you can sell time. We have a member areas product, so you can sell access to, like, you could have a private blog, private video lessons. You can combine that with our email campaigns product to do a sub-stack-like product with Joining Forces with Talk. You can do to-go ordering, reservations on Squarespace. There's just many, many, many ways to Transact. And what I'm excited about over the next couple of years is just having all of those exist within one platform and have our …

AI assessment note: “what I'm excited about over the next couple of years is just having all of those exist within one platform”

Q That was a different time though. I'm sure you have many founders ask you for advice today. Would you advise them to take advantage of the capital rich markets today? Or would you say, actually, my model worked well, build a business that can get to break even?

A Look, I would always encourage people to get to a business. It's so hard to give generic advice. I mean, because there are businesses where that's probably bad advice, but I mean, in the whole scheme of things, if you are break, even you are more in control of your destiny and it puts you in a better negotiating position for when, you know, you do need to go or want to go and raise money because you can take it or leave it. And so, I don't know. I've always been, you know, very dilution sensitive and just making sure I have a point for the money as opposed to stockpiling it or burning irresponsibly or anything like that.

AI assessment note: “if you are break, even you are more in control of your destiny”

Q Can I ask? I mean, that's a misnomer. Do you think there's any other misnomers of Squarespace that people have?

A You know, for a long time, and I'm not sure it's really true today, because of our emphasis on design and on creatives, and, you know, they were sort of like, oh, well, is it just for that community? Is it, you know, we're headquartered in New York. It's just for, like, you know, artsy people in New York. And I was always like, no, it's never been for that. It's, it's been for Exposing the benefits of that kind of thing to a much broader customer base. And so, like, should a dentist use Squarespace? Absolutely they should use Squarespace, and they should have an amazingly designed website that highlights their message and gets them more business. And so it was always about bringing that, that notion of design and aesthetics to everyone, as opposed to saying, no, it's only for the people, you know, the certain group of people who really care about that.

AI assessment note: “oh, well, is it just for that community? Is it... just for, like... artsy people”

Q That is very, very kind of you, but I want to start today with a little bit of the story. You know, we see Squarespace is this incredible public market's behemoth today, but it all started in the dorm room, which I just love as the foundation story, so take me back there. What was that founding aha moment for you?

A Yeah, I mean, wow, we're talking 18 years ago now when I first started programming it. You know, my background is engineering and design And so, you know, back a zillion years ago, I wanted a website for myself, and I was very frustrated with what was out there, and I wanted something that was all in one, and back then that meant, like, page builder and photo galleries and hosting and statistics software were together. I mean, it's, like, unimaginable now. And I wanted something that was really design-centric and looked really good, and I think that, especially back then, I think we take it for granted a little bit now, but design on the web was not really a great thing, and I've always been a huge, Fan of design and aesthetics, and I wanted something to look good, so I started making Squarespace really for myself.

AI assessment note: “I wanted a website for myself, and I was very frustrated with what was out”

Q Can I ask, we're all expect founders to have these grand visions today, and I think that's a little bit bullshit, because no offense, when you started Squarespace 18 years ago, did you have a grand vision that it would be this incredible public markets company, or was it just like a great project that you were passionate about?

A You know, I of course didn't think I could have never thought forward to what it's become today, and I also don't necessarily think Frame its accomplishments in financial goals, which is the transition to a public market, is a huge honor, really, but it is just really one step along the way. I think I knew by early people's reaction to it that it was going to be something people liked a lot, and, you know, there was an uphill battle along the way, obviously, selling people on, frankly, the importance of design and what it could do for them, and, you know, we look at it now, and it's obvious that was a huge differentiator in the company, and it really set us forward, but that wasn't necessarily obvious the whole way through.

AI assessment note: “I of course didn't think I could have never thought forward to what it's become”

Q What would that have properties are if you have great cash flow, if you have great unit economics, and you're printing money direct?

A Easy to understand business, you know, great top line growth rate, great cash flow, lots of recurring revenues, stable churn, all these predictable, you know, there's a lot of Solid things within the company that make it, you know, frankly pretty easy , I think pretty easy to understand. Yeah, I mean, when thinking about those different formats, I mean, the direct listings, it's definitely a little strange. I mean, just kind of a free-for-all in the early days, and I think that, you know, what people have told me, you know, I've been now public for all of, what, three, four months? Like, you know, not very long, is that this stuff will normalize out, you know, over the years. It's just in the near term, it's a bit choppy. I mean, your volume can be low, it can It could be because direct listing, you know, people don't have the same modeling capabilities because you haven't been out there for a while. You don't have a lot of quarters under your belt. There was no lockups. I mean, there's all these things that are kind of going into it.

AI assessment note: “great top line growth rate, great cash flow, lots of recurring revenues, stable churn”

Q You mentioned when you were about ten million run rate, you could have raised, I'm sure, when you were at five million or three million, when you'd outproved a lot of points. Do you wish now, looking back, that you had raised earlier, or are you happy at the point in which you raised?

A It's such a unique raise because the driver for it was not a ton of money into the business, and so I really kind of just kept taking the opposite stance of a lot of people, which was, I think a lot of people want to raise as much as possible, as fast as possible, you know, in case times were bad, and then, you know, they'll have a buffer or something like that, and I never needed the buffer, and so, not really, I mean, they needed some buffer, but, like, I never needed, like, a big buffer because it was always cash flow breakeven, so I was just trying to minimize the amount raised. And I think my problems were not exactly money dependent back then as much as they were making the product easier to use or, you know, engineering management or things like that, that money can't just directly fix.

AI assessment note: “I never needed, like, a big buffer because it was always cash flow breakeven”

Q Can I ask, why do you buy the bundled model versus the unbundled model? If you think about, like, feature richness and depth, like, bluntly, there are things that substack as they scale and have bigger and bigger engineering teams, they can, players can do in more depth than you can because it's all that they do. Why do you buy the bundled over the unbundled?

A Well, what's sort of interesting is that, you know, we've made it a point to go very, very deep into a couple areas that we play in, and sometimes that meant an acquisition for us, like Acuity or With Talk, where we couldn't have Possibly gotten to where, you know, they've gotten on their own. And so I think there's a lot of convergence that happens. I mean, I think if you're, you know, a restaurant and, you know, you're on a platform like that, you want to be selling items, like it's very, very hard to create the depth of an e-commerce platform like what Squarespace has. Or if you're, as you mentioned, Substack, having the archive of the emails on the web sort of starts to look like a blog, and then maybe that's on a domain, and maybe that looks like a website, you know, and you start to see the benefit of kind of having it Sort of in one place. I think, you know, also just merging things like the CRM together, like trying to figure out from, I sent an email, they landed to my website, they bought something, they're in my database, you know, just that stuff coming together, that's pretty hard to do when they're separate platforms.

AI assessment note: “that stuff coming together, that's pretty hard to do when they're separate platforms.”

Q Can I ask, we're all expect founders to have these grand visions today, and I think that's a little bit bullshit, because no offense, when you started Squarespace 18 years ago, did you have a grand vision that it would be this incredible public markets company, or was it just like a great project that you were passionate about?

A You know, I of course didn't think I could have never thought forward to what it's become today, and I also don't necessarily think Frame its accomplishments in financial goals, which is the transition to a public market, is a huge honor, really, but it is just really one step along the way. I think I knew by early people's reaction to it that it was going to be something people liked a lot, and, you know, there was an uphill battle along the way, obviously, selling people on, frankly, the importance of design and what it could do for them, and, you know, we look at it now, and it's obvious that was a huge differentiator in the company, and it really set us forward, but that wasn't necessarily obvious the whole way through.

AI assessment note: “I of course didn't think I could have never thought forward to what it's become”

Q What would that have properties are if you have great cash flow, if you have great unit economics, and you're printing money direct?

A Easy to understand business, you know, great top line growth rate, great cash flow, lots of recurring revenues, stable churn, all these predictable, you know, there's a lot of Solid things within the company that make it, you know, frankly pretty easy , I think pretty easy to understand. Yeah, I mean, when thinking about those different formats, I mean, the direct listings, it's definitely a little strange. I mean, just kind of a free-for-all in the early days, and I think that, you know, what people have told me, you know, I've been now public for all of, what, three, four months? Like, you know, not very long, is that this stuff will normalize out, you know, over the years. It's just in the near term, it's a bit choppy. I mean, your volume can be low, it can It could be because direct listing, you know, people don't have the same modeling capabilities because you haven't been out there for a while. You don't have a lot of quarters under your belt. There was no lockups. I mean, there's all these things that are kind of going into it.

AI assessment note: “Easy to understand business, you know, great top line growth rate, great cash flow”

Q You mentioned when you were about ten million run rate, you could have raised, I'm sure, when you were at five million or three million, when you'd outproved a lot of points. Do you wish now, looking back, that you had raised earlier, or are you happy at the point in which you raised?

A It's such a unique raise because the driver for it was not a ton of money into the business, and so I really kind of just kept taking the opposite stance of a lot of people, which was, I think a lot of people want to raise as much as possible, as fast as possible, you know, in case times were bad, and then, you know, they'll have a buffer or something like that, and I never needed the buffer, and so, not really, I mean, they needed some buffer, but, like, I never needed, like, a big buffer because it was always cash flow breakeven, so I was just trying to minimize the amount raised. And I think my problems were not exactly money dependent back then as much as they were making the product easier to use or, you know, engineering management or things like that, that money can't just directly fix.

AI assessment note: “not really... I never needed, like, a big buffer because it was always cash flow breakeven”

Q Can I ask, you mentioned the secondaries element. How do you advise founders on the secondaries element? We see founders, say, taking them earlier and earlier. How do you feel about it, and did it change your mindset?

A So back when I took some secondary, I would say it was, and this is 2010, it was very much not the norm, and I was looking to do it for a very specific reason, because I didn't want to sell the company, and at the time I basically owned all of it. And so, you know, I was like, look, you know, I don't come from some Background where I have a bunch of money or anything. And, you know, at some point you start to feel irresponsible where it's like, okay, I'm getting offers for how much money? Like, I don't even know what that means. And so I was like, okay, well, how do I get a deal where people who otherwise couldn't participate in this company get to participate on the investment side? And I'm kind of, for whatever is in my head, you know, taking those sort of acquisition things off the table. And, you know, I was able to reach that deal with, with certain investors. Other investors looked at that and they were like, there's no way I'm giving this, you know, 20 some year old kid, X, Y, and Z monies to I'm just gonna leave, and I was like, that doesn't make any sense. If I wanted the money, I'd just sell the company, right? So, like, I understand it. I think it was actually very empowering in the sense that I think it let me take more risks in the company, otherwise maybe would have continued to hesitate on, because I guess I felt this sort of, like, everything will be okay, and I…

AI assessment note: “I think it was actually very empowering in the sense that I think it let”

Q What have you loved, and what have you not enjoyed?

A Oh my god, you're gonna have to end the same. I think it's exhilarating. It's interesting to think that, you know, on any given quarter, what you're doing is judged. You see the results of it pretty quickly. Fairly or unfairly, by the way. I mean, I think there can be a lot of, you know, we're witnessing quarters in our industry kind of lap the COVID quarters, and people Kind of freaking out about that, but it's kind of a very short term thing versus looking at a business that's been around for two decades and thinking about where it'll be the next decade and, you know, thinking about if you want to be a long term holder of it. So that dynamic is, has been puzzling. Look, I mean, you're kind of at the final stages of this. If you're doing a really, really, really great job, you'll just get rewarded almost in real time, which is exhilarating. You know, I think you have to have a lot of conversations with people on the side of things. And some I really, really enjoy very, very, very, very thoughtful conversations With people who want to be supportive and have done their work on the company and think about it, and they ask great questions, and I've had some that, you know, haven't really felt that way.

AI assessment note: “I think it's exhilarating... So that dynamic is, has been puzzling.”

Q What mistakes did you make? Because I do the honeypotting. I get, I really like you, Anthony. You're hired, and you may not be a candidate, but I like you, and we're going to have a great time together, and we hit it off. What mistakes did you make?

A Oh my God, there's so many of them that I don't even know where to begin. I think outside of raw skill sets, I think that there's a emotional maturity that comes with running teams of certain sizes, and there are certain personalities that always are amplifying levels of panic and problems and spewing that out, and there are certain personalities that naturally want to de-escalate things, solve things, collaborate. I'm just much better at getting the softer side of things right now versus just And figuring out and helping people when that's going wrong versus, you know, just only seeing the other side of things. I think the thing that was hard for me is every time Squarespace hires somebody, it's the biggest company I've ever worked for. And so, you know, I'm relying on a lot of people around me who've done this elsewhere and manage much bigger teams than me in many cases. And I've really learned to learn from them, which has been a real pleasure. And that's kind of necessarily the case when, you know, when it's kind of for the first time.

AI assessment note: “I'm just much better at getting the softer side of things right now”

Q Anthony, you were giving me advice before we started the show. I love advice here, you know, in terms of like relationships It's one that I oscillate on back and forth. How do you find your relationship to money has changed over time?

A Oh my god, what an interesting question. It gets I'm more comfortable with it. It's in 18 years. I'm not sure I still, you know, look, I mean, Squarespace is still, I hope, a very disciplined company. I mean, we're one of the few companies you're going to see with top line revenue growth like ours, but also great free cash flow. And that doesn't come from, you know, all of a sudden thinking money doesn't matter, spending doesn't matter, dynamics don't matter. It completely matters. So I care about, I mean, small details of how we spend inside Squarespace. But look, I mean, time goes on and you can be a little more, it's an enabler. I think what it enables within people that really is going to depend on, I think, certain people's character. It's sort of like back to your question around the early investment. Like, why didn't you just, you know, okay, there's X million dollars in the bank. Why didn't you spend it all right away? It's, I don't know. I would never do that. So, you know, it doesn't matter if there's eight million dollars there, eight hundred million dollars there.

AI assessment note: “I'm more comfortable with it. It's in 18 years.”

Q That's really interesting, because I spoke to your investors before, and they said that one of your big strengths is, you know, how you think about acquisitions. How do you think about acquisitions and that build versus buy decision?

A I think of them as partnerships with great entrepreneurs for the most part, and I think that, you know, we'd never done any until probably only three years ago. It's kind of been a great pleasure to be able to work with company founders and insofar as they have to deal with the negatives and the positives of being inside a larger company. You know, I'm an entrepreneur like them, and a lot of the company, all the companies are Obviously acquiring smaller than us, but all these companies have their own nuances, but I'm used to so many different phases of their growth, and I'd like to think I have a particular sensitivity to protecting what I need to protect within those acquired companies, knowing full well that they're not going to be exactly the same. They shouldn't be. But yeah, I just try and be as sensitive as possible to the nuances of each person's scenario, and empathetic, because I'm a, I'm an entrepreneur myself.

AI assessment note: “I think of them as partnerships with great entrepreneurs for the most part”

Q Final one, my friend. What do the next five years hold for you and for Squarespace? Paint that picture for me.

A Look, I mean, so we're a newly public company, which is, you know, been fascinating, and we're learning this side of the journey. You know, a lot of people look at it, and I always hated people who sort of look at it and say, like, oh, look, there's, like, it's a, they call it an exit. That's so weird to me, because I go to different companies that I admire, and I do, like, the max graph view on their, their stock, and it's like, whoa, that company is 50 times bigger after a public, or, like, I mean, there's just so much more that there is left for us. And so I am really excited to continue to build and partner with great teams to build great products and help entrepreneurs and help people with self-expression and help people transact online. I just think we're at the very beginning of this story. We're just so well positioned to help so many people out, and so I'm excited to be part of that story.

AI assessment note: “there's just so much more that there is left for us”

Q That's really interesting, because I spoke to your investors before, and they said that one of your big strengths is, you know, how you think about acquisitions. How do you think about acquisitions and that build versus buy decision?

A I think of them as partnerships with great entrepreneurs for the most part, and I think that, you know, we'd never done any until probably only three years ago. It's kind of been a great pleasure to be able to work with company founders and insofar as they have to deal with the negatives and the positives of being inside a larger company. You know, I'm an entrepreneur like them, and a lot of the company, all the companies are Obviously acquiring smaller than us, but all these companies have their own nuances, but I'm used to so many different phases of their growth, and I'd like to think I have a particular sensitivity to protecting what I need to protect within those acquired companies, knowing full well that they're not going to be exactly the same. They shouldn't be. But yeah, I just try and be as sensitive as possible to the nuances of each person's scenario, and empathetic, because I'm a, I'm an entrepreneur myself.

AI assessment note: “I think of them as partnerships with great entrepreneurs for the most part”

Q Anthony, you were giving me advice before we started the show. I love advice here, you know, in terms of like relationships It's one that I oscillate on back and forth. How do you find your relationship to money has changed over time?

A Oh my god, what an interesting question. It gets I'm more comfortable with it. It's in 18 years. I'm not sure I still, you know, look, I mean, Squarespace is still, I hope, a very disciplined company. I mean, we're one of the few companies you're going to see with top line revenue growth like ours, but also great free cash flow. And that doesn't come from, you know, all of a sudden thinking money doesn't matter, spending doesn't matter, dynamics don't matter. It completely matters. So I care about, I mean, small details of how we spend inside Squarespace. But look, I mean, time goes on and you can be a little more, it's an enabler. I think what it enables within people that really is going to depend on, I think, certain people's character. It's sort of like back to your question around the early investment. Like, why didn't you just, you know, okay, there's X million dollars in the bank. Why didn't you spend it all right away? It's, I don't know. I would never do that. So, you know, it doesn't matter if there's eight million dollars there, eight hundred million dollars there.

AI assessment note: “I'm more comfortable with it.”

Q What mistakes did you make? Because I do the honeypotting. I get, I really like you, Anthony. You're hired, and you may not be a candidate, but I like you, and we're going to have a great time together, and we hit it off. What mistakes did you make?

A Oh my God, there's so many of them that I don't even know where to begin. I think outside of raw skill sets, I think that there's a emotional maturity that comes with running teams of certain sizes, and there are certain personalities that always are amplifying levels of panic and problems and spewing that out, and there are certain personalities that naturally want to de-escalate things, solve things, collaborate. I'm just much better at getting the softer side of things right now versus just And figuring out and helping people when that's going wrong versus, you know, just only seeing the other side of things. I think the thing that was hard for me is every time Squarespace hires somebody, it's the biggest company I've ever worked for. And so, you know, I'm relying on a lot of people around me who've done this elsewhere and manage much bigger teams than me in many cases. And I've really learned to learn from them, which has been a real pleasure. And that's kind of necessarily the case when, you know, when it's kind of for the first time.

AI assessment note: “Oh my God, there's so many of them that I don't even know”