The Exchanges

Q best founders that, you know, you know, and you've, uh, kind of grown alongside. We spoke about kind of Henrique at Brex before we spoke about John at Stripe. When you think about kind of commonalities and lessons from them, have there been some takeaways from watching them scale Stripe and Brex that you've really kind of taken with you in terms of how you think about your operating mentality?

A Yeah. So this actually came up recently is we're looking for a head of engineering and Now, and our head of engineering, you know, profile, we've been looking for it for maybe six months or something, and the profile has shifted a little bit as, you know, our virtual engineering team has grown a little bit, as we've gotten more successful, et cetera, the profile has shifted a little bit, and what's interesting about, if you look at, you know, let's say both Henrique and John, is that they're both incredibly bold, and so this is, you know, kind of goes against what I was saying a little bit, you know, a minute ago or so, regarding sort of being fairly measured, sort of being fairly realistic with yourself, et cetera. They both actually sort of dream incredibly big, and so, for example, John told me once, when we're sort of thinking about head of engineering profiles, he's like, you know, all these candidates are not good. You know, you should be going after something more like this. And then he named someone who is the CEO, I think, of a maybe ten billion dollar company right now in Silicon Valley. And he was like, there's a 10% chance you can get this person as your head of engineer. And I was like, wow. That was like no way would I have ever thought I could get, you know, the CEO of a ten billion dollar unicorn in Silicon Valley to come be your head of engineering. And John sa…

AI assessment note: “both Henrique and John, is that they're both incredibly bold”

Q best founders that, you know, you know, and you've, uh, kind of grown alongside. We spoke about kind of Henrique at Brex before we spoke about John at Stripe. When you think about kind of commonalities and lessons from them, have there been some takeaways from watching them scale Stripe and Brex that you've really kind of taken with you in terms of how you think about your operating mentality?

A Yeah. So this actually came up recently is we're looking for a head of engineering and Now, and our head of engineering, you know, profile, we've been looking for it for maybe six months or something, and the profile has shifted a little bit as, you know, our virtual engineering team has grown a little bit, as we've gotten more successful, et cetera, the profile has shifted a little bit, and what's interesting about, if you look at, you know, let's say both Henrique and John, is that they're both incredibly bold, and so this is, you know, kind of goes against what I was saying a little bit, you know, a minute ago or so, regarding sort of being fairly measured, sort of being fairly realistic with yourself, et cetera. They both actually sort of dream incredibly big, and so, for example, John told me once, when we're sort of thinking about head of engineering profiles, he's like, you know, all these candidates are not good. You know, you should be going after something more like this. And then he named someone who is the CEO, I think, of a maybe ten billion dollar company right now in Silicon Valley. And he was like, there's a 10% chance you can get this person as your head of engineer. And I was like, wow. That was like no way would I have ever thought I could get, you know, the CEO of a ten billion dollar unicorn in Silicon Valley to come be your head of engineering. And John sa…

AI assessment note: “if you look at... both Henrique and John, is that they're both incredibly bold”

Q to John, and having access to that kind of mentorship, I guess, in the early days, you know, came through the YC network, and when we chatted before, you said something that was really interesting to me, which was, you said, YC is useful pre-product market fit, but useless post-product market fit. So, what makes you say this, and I guess, what makes you say this? Let's start with that.

A Yeah, so, I think the most surprising thing about YC is actually that there's nothing really surprising about it. You actually don't learn anything new. Going to sort of all the dinners, or Even Demo Day or whatever else. Almost everything YC tells you is available online. If you just go read every PG essay, you know, you could probably become a YC partner, basically, if you read every essay, and just maybe that's being a little bit uncharitable, but, you know, I think you could sort of get most, maybe, 95% of the advice you get from YC just by reading the essays. That said, I think the, the advice is not particularly helpful, but the networks that you build, I think, are quite helpful, but those networks really are useful pre-product marketplace. When you're trying to get, let's say, advice from potential customers, you're, you know, trying to figure out what the product should look like, all that kind of important sort of early day stuff. And that's the kind of stuff that it's helpful to have sort of other people next to you where you can sort of bounce ideas off of them, get their thoughts on, et cetera, stuff like that. Once you have product pocket fit, you don't really need to be talking to anybody who's just kind of heads down, just executing, just writing code, talking to customers, you know, for, for as many hours a day as you can, really. And so once that does happen, …

AI assessment note: “YC doesn't really add any particular value at that point in time”

Q like, you don't need the help that the VC would bring, which brings me to something else that you said, though, which is, like, VC's Pre-product market fit aren't so helpful, but post, they're very helpful. So I'd love to hear your thoughts, because that kind of flies in the face of, like, my experience of, like, post-product market fit, they don't need you. How do you think about that?

A Yeah, so retail has not always been going, you know, that well, right? You know, we certainly sort of had our struggles, you know, in the early days, right? And during those days, I would say, what VCs did for us did not necessarily make that big of a difference. I think, you know, it is true that when companies are not doing well, they'll sort of ask for more help, Ask for more advice or whatever else. But I think in the end, it doesn't actually make that much of a difference. You may sort of spend more time with the company, but that doesn't actually sort of translate into more results or anything, or does it translate into sort of value creation or whatever else? That's maybe one thought there. On the pre and post product market fit, yeah, it's interesting because it's the opposite of YC, where I think VCs where they can add a lot of value is not really sort of telling you what to build typically or how to build it. It really is, you know, something's working already. How can we scale this thing up and how can we grow a Faster. How can we sort of see around the corners that you might not see? And in that case, Sequoia has been tremendously helpful. So I remember maybe a year and a half ago or so, Sequoia, for example, kept on pushing us to go hire more leaders for the company. And I was very skeptical of this. I was thinking to myself, the company's going pretty well. Sales …

AI assessment note: “where VCs where they can add a lot of value is not really sort of telling”

Q Henrik ever lacks courage, let's just put it that way. Final one is, like, you mentioned before about, kind of, the top three decisions that you made, and how pivotal it was in terms of Sequoia and the Angels. When you think about the other two, if you were to choose one, what do you think another one is, and how did it have such a transformational impact on Retool?

A I think the other one is, as we've been talking about already- I think it is hiring slowly and sort of building the fundamentals. I think if you look at Retool, you know, I think the company is, what, three and a half years old, so, you know, by all sort of means, it doesn't look like it was that slow, you know, reached a billion after an evaluation, at least, at three and a half. And yet, if you look at the first year and a half, the team was less than, I think, three people, something, myself included. It was a tiny team for the first year and a half, and it was only until, you know, year one and a half, year two or something, when we really started, sort of, pedal to the metal, really started Higher. That has a lot of effects or second order effects that you might not think about. So one, I think by doing everything yourselves, you actually learn a tremendous amount about all areas of business, you know, and so I think I now have a much more respect for, let's say, sales and market, all the go-to-market functions, I think are incredibly critical to the company, whereas before I might have been like, oh, you know, sales is really easy. It's like, call some people, right? And, you know, deals close. In reality, of course, it's substantially harder than that. If anything, it may be harder than engineering to really do sales properly. And so, uh, I think you sort of Gained a lot…

AI assessment note: “I think the other one is... hiring slowly and sort of building the fundamentals.”

Q to John, and having access to that kind of mentorship, I guess, in the early days, you know, came through the YC network, and when we chatted before, you said something that was really interesting to me, which was, you said, YC is useful pre-product market fit, but useless post-product market fit. So, what makes you say this, and I guess, what makes you say this? Let's start with that.

A Yeah, so, I think the most surprising thing about YC is actually that there's nothing really surprising about it. You actually don't learn anything new. Going to sort of all the dinners, or Even Demo Day or whatever else. Almost everything YC tells you is available online. If you just go read every PG essay, you know, you could probably become a YC partner, basically, if you read every essay, and just maybe that's being a little bit uncharitable, but, you know, I think you could sort of get most, maybe, 95% of the advice you get from YC just by reading the essays. That said, I think the, the advice is not particularly helpful, but the networks that you build, I think, are quite helpful, but those networks really are useful pre-product marketplace. When you're trying to get, let's say, advice from potential customers, you're, you know, trying to figure out what the product should look like, all that kind of important sort of early day stuff. And that's the kind of stuff that it's helpful to have sort of other people next to you where you can sort of bounce ideas off of them, get their thoughts on, et cetera, stuff like that. Once you have product pocket fit, you don't really need to be talking to anybody who's just kind of heads down, just executing, just writing code, talking to customers, you know, for, for as many hours a day as you can, really. And so once that does happen, …

AI assessment note: “those networks really are useful pre-product marketplace... Once you have product pocket fit, you don't really need”

Q like, you don't need the help that the VC would bring, which brings me to something else that you said, though, which is, like, VC's Pre-product market fit aren't so helpful, but post, they're very helpful. So I'd love to hear your thoughts, because that kind of flies in the face of, like, my experience of, like, post-product market fit, they don't need you. How do you think about that?

A Yeah, so retail has not always been going, you know, that well, right? You know, we certainly sort of had our struggles, you know, in the early days, right? And during those days, I would say, what VCs did for us did not necessarily make that big of a difference. I think, you know, it is true that when companies are not doing well, they'll sort of ask for more help, Ask for more advice or whatever else. But I think in the end, it doesn't actually make that much of a difference. You may sort of spend more time with the company, but that doesn't actually sort of translate into more results or anything, or does it translate into sort of value creation or whatever else? That's maybe one thought there. On the pre and post product market fit, yeah, it's interesting because it's the opposite of YC, where I think VCs where they can add a lot of value is not really sort of telling you what to build typically or how to build it. It really is, you know, something's working already. How can we scale this thing up and how can we grow a Faster. How can we sort of see around the corners that you might not see? And in that case, Sequoia has been tremendously helpful. So I remember maybe a year and a half ago or so, Sequoia, for example, kept on pushing us to go hire more leaders for the company. And I was very skeptical of this. I was thinking to myself, the company's going pretty well. Sales …

AI assessment note: “where they can add a lot of value is not really sort of telling you what to build”

Q Henrik ever lacks courage, let's just put it that way. Final one is, like, you mentioned before about, kind of, the top three decisions that you made, and how pivotal it was in terms of Sequoia and the Angels. When you think about the other two, if you were to choose one, what do you think another one is, and how did it have such a transformational impact on Retool?

A I think the other one is, as we've been talking about already- I think it is hiring slowly and sort of building the fundamentals. I think if you look at Retool, you know, I think the company is, what, three and a half years old, so, you know, by all sort of means, it doesn't look like it was that slow, you know, reached a billion after an evaluation, at least, at three and a half. And yet, if you look at the first year and a half, the team was less than, I think, three people, something, myself included. It was a tiny team for the first year and a half, and it was only until, you know, year one and a half, year two or something, when we really started, sort of, pedal to the metal, really started Higher. That has a lot of effects or second order effects that you might not think about. So one, I think by doing everything yourselves, you actually learn a tremendous amount about all areas of business, you know, and so I think I now have a much more respect for, let's say, sales and market, all the go-to-market functions, I think are incredibly critical to the company, whereas before I might have been like, oh, you know, sales is really easy. It's like, call some people, right? And, you know, deals close. In reality, of course, it's substantially harder than that. If anything, it may be harder than engineering to really do sales properly. And so, uh, I think you sort of Gained a lot…

AI assessment note: “I think the other one is... hiring slowly and sort of building the fundamentals.”

Q I love that, and totally. Ok, interesting one here. Who's the best board member you've worked with and why? What's been the biggest takeaway from having Brian on the board?

A Yeah, I think initially I was quite sceptical about VCs, and I think part of it is because when you deal with VCs Pre-product market fit. There's nothing for them to give you advice on, right, besides the product. And so a lot of the product advice that we got, I candidly thought wasn't so great, and so I sort of developed a very sort of skeptical view of VCs. That said, I think VCs really are experts in scaling companies, and the sort of advice Brian has given us regarding how to scale companies, what challenges we'll have in six months and a year's time, have been incredibly accurate. It's funny, you know, if I could tell myself a year ago something, I'd probably say something along the lines like, trust Brian a bit more, or something like that.

AI assessment note: “I'd probably say something along the lines like, trust Brian a bit more”

Q I would have said, well, you know, Sequoia won't get their ownership, but they need to really be incentivized to really give you the time. You'll then have five angels that have one or two percent, and are they really incentivized? You know, they're probably gonna be, you know, OGs of the industry, which they are. Is one or two percent gonna really incentivize them? Like, why was I wrong?

A So I think when it comes to, let's say, so on the first point, sort of regarding ownership percentages, I think this is mostly not true. I was gonna say bullshit, but I think it's mostly not true, I think. I think there's obviously some truth to it, obviously, right? You know, if UFOs owned two percent of a company, it's certainly less incentivized than if you owned, like, 10% or something. In our case, I think Sequoia probably owns, I think it's either 15 or 17%, something like that, or in the Series A, at least, they own something like that. And 15 or 17 is not radically different from, you know, Or whatever it is, 25, or whatever the typical series is. It's not radically different, and so I think ultimately, and I think this is probably true for you as well, if one of your companies does extremely well, you want to help out, you know, you sort of, you're not doing the math in your head about, okay, well, you know, actually, this company's doing well, but I only own 15% of it, I suppose, 17% or 20%. Therefore, you know, sort of on a per hour basis, I'm, you know, my time is better spent in this company that owns, where I own 20%. I think the delta between sort of two companies that It's probably greater than 25%, and so you'd probably much rather help the sort of company that's doing incredibly well rather than the company that is doing probably quite a bit less well where yo…

AI assessment note: “on the first point, sort of regarding ownership percentages, I think this is mostly not true”

Q levers of growth versus profitability? I understand everything you said there, but a lot go, ah, but with VC dollars, I can really be very expansive in terms of my sales and marketing activities. I can really be aggressive, multi-test on marketing channels, and just be a lot more aggressive. Like, how do you think about that growth versus profitability, and kind of also the marketing and aggressive sales spend?

A Yeah, so I think, at least in our case, we want to be profitable in the sense that sort of we have a basic business that's going pretty well, right? And then by having this business that's sort of fundamentally working, we can then try new things that we can afford to take more risks, because we know if the risks don't pay off, we still have the fundamental business that's growing, you know, sort of many multiples here on here today. And so for us, that's the reason why we raised is, you know, if we had not raised, theoretically, we could have been more like Zapier or something. And I think Zapier is now, I'm not sure, 50, 80, a hundred million or something like that, and to my knowledge, they've never raised a round after the seat. Having raised in the Series A, I think, did, well, I'm trying to think whether it actually made us grow faster or not. I mean, when we raised the Series B, I think we've spent a million dollars in the Series A, so, so, you know, I guess we haven't really deployed the capital very much. That said, I do think it really upped our ambition, and I think this is one thing that Visa's going to top a lot with, because if you bootstrapped There's kind of always a sort of nagging thought in the back of your mind that if everything goes to shit, I can always move to Hawaii, and, you know, we have a business that's profitable, and life can't be that bad, right?…

AI assessment note: “we want to be profitable in the sense that sort of we have a basic business”

Q well, there's so many things that are really interesting about the journey, but you know, the twenty-five million A, when you were at a millionaire and you were at four people in the team, it's a chunky round, and it's a chunky A. What was your thinking around, and around that? Were you nervous about taking on such a large capital kind of injection, and what was the thoughts there?

A Yeah, I think really interesting is sort of the, uh, divide between bootstrapping and raising VC. I think there's actually less of a divide than many people think. And so in our case, we could have, well, we did raise, as you can see, and we also could have not raised, actually. You know, at that point, we were four people. I think we would raise maybe 1.4, something like that in the seed. And so I think when we were raising our A, I think we'd burn maybe a hundred K of the 1.4, something like that. And, you know, four people doing a mill in ARR or a software company already profited Right. So we didn't need to raise at all. But the fact that we didn't need to raise and could bootstrap actually then caused us to be able to raise a lot because, you know, VCs, I think, are quite excited by businesses that are actually working as opposed to ones that, you know, need VC money to work and, you know, may or may not work. And so in our case, and this has to date still been true, is if that if you sort of are on the precipice or are already profitable, raising money actually becomes substantially easier. And I think one key point here, too, is once you become, once you sort Set yourself up for profitability in the early days. It's actually quite hard to ever become unprofitable, actually. And so if you do the math, right, you know, let's say we're a million dollars for people. Yeah, ne…

AI assessment note: “the fact that we didn't need to raise and could bootstrap actually then caused us”

Q as you are. My question to you is, like, you know, you said there are three people after a year and a half, 45 now, three and a half years in. With scaling that fast, things break. What's broken, and I'm sure you fixed it very fast, but it was broken in the past, and what have been some lessons in terms of scaling as fast as you have done?

A Yeah, I think the hardest one has been hiring for us. I think in the end, most Problems that we've had at Retool. I think most problems in business for a host of this is, to some extent, a people problem, right? I think, you know, engineering problems can be solved with the right people. Sales problems can solve the right people. Marketing problems with the right people, etc. And so, really, at this point, the challenge for a reasonable head of us is finding the right people to really help us build the company. And most of the mistakes we've made have been regarding hiring, not hiring the right people, sometimes hiring the wrong people, and then sort of having to crack those mistakes and As quickly as possible. I think a lot of them have to do with sort of cultural misalignment, and so for a while, I, as a technical founder, I think sort of underweighted culture, where I thought culture is the sort of fluffy thing that doesn't actually really matter very much, but I think now it's absolutely critical. It may be sort of one of the three defining features of Retool, sort of, you know, if we succeed, culture may actually be one of the three reasons why we did so, and today it's become incredibly important, and something that we really screened during the interview Process. But this is not always the case. I think in the early days, we certainly made many mistakes. Either wrong per…

AI assessment note: “most of the mistakes we've made have been regarding hiring”

Q I would have said, well, you know, Sequoia won't get their ownership, but they need to really be incentivized to really give you the time. You'll then have five angels that have one or two percent, and are they really incentivized? You know, they're probably gonna be, you know, OGs of the industry, which they are. Is one or two percent gonna really incentivize them? Like, why was I wrong?

A So I think when it comes to, let's say, so on the first point, sort of regarding ownership percentages, I think this is mostly not true. I was gonna say bullshit, but I think it's mostly not true, I think. I think there's obviously some truth to it, obviously, right? You know, if UFOs owned two percent of a company, it's certainly less incentivized than if you owned, like, 10% or something. In our case, I think Sequoia probably owns, I think it's either 15 or 17%, something like that, or in the Series A, at least, they own something like that. And 15 or 17 is not radically different from, you know, Or whatever it is, 25, or whatever the typical series is. It's not radically different, and so I think ultimately, and I think this is probably true for you as well, if one of your companies does extremely well, you want to help out, you know, you sort of, you're not doing the math in your head about, okay, well, you know, actually, this company's doing well, but I only own 15% of it, I suppose, 17% or 20%. Therefore, you know, sort of on a per hour basis, I'm, you know, my time is better spent in this company that owns, where I own 20%. I think the delta between sort of two companies that It's probably greater than 25%, and so you'd probably much rather help the sort of company that's doing incredibly well rather than the company that is doing probably quite a bit less well where yo…

AI assessment note: “regarding ownership percentages, I think this is mostly not true”

Q Got you. No, I mean, listen, I love that. As I said, I welcome any British accent. How did then, like, philosophy and CS degree at Oxford, how did that lead to retool?

A Yeah, ok, so this is kind of a, you know, a long story at this point. It's a bit of a detour, and so what happened was when I was in Oxford, I was American, and so one of the major, I was working on a bunch of side projects, Basically. And one of the major side projects that we ended up working on was basically something like a clone of Venmo, basically, for the UK. Because, I mean, as you know, in the UK, you send money via faster payments, probably. You know, you use an account number, you use a sort code. And I remember back, you know, when I was an undergrad there, this must have been 2013 or so, 2014, something like that, the mobile apps were actually pretty bad. And so, if you use, let's say, Santander or Barclays or whatever else, it was actually quite difficult to send money back. And so to me, this seemed, you know, enormously stupid. You know, clearly this is something that tech, you know, it's not that hard to solve. It's changing sort of a number of the database and moving some money back and forth. How hard could that be? And so we decided to start working on basically a clone of Venmo, basically. That actually went reasonably well. It actually got a bunch of users, and we actually got into YC doing that. But then it turns out it's actually a terrible business in the sense that every time someone sends money, we were losing money. And so the faster we grew, the mor…

AI assessment note: “when I was in Oxford, I was working on a bunch of side projects”

Q Wow, that is a lot of credit to give to it. Next one. What would you most like to change about the Silicon Valley tech scene?

A Silicon Valley texting is quite insular. It's funny you ask this, because to some extent, I suppose the texting in the UK, texting in the UK is definitely smaller, but it's actually, I think, much more positive and uplifting to some extent. I think, you know, the rest of British culture maybe not, but the texting actually is, because when you run into someone who is in tech in London, it's so exciting, you know, you're sort of so pleased to see them, and you can always sort of connect or bond about something. Right, and you want to talk with them. Whereas in San Francisco, or in Silicon Valley, you know, everyone works in tech, and so it's not special to work in tech. You know, if anything, all my friends are telling me they don't want to have more tech friends. They want to find non-tech friends, you know, and I think that's a little bit sad. I think that sort of tech has got such a bad rap in Silicon Valley, but also that the, I think the culture is quite insular, and to some extent, this is why YC works, because YC can sort of bring you into the fold, sort of get you connected very quickly into the tech scene, but I do wish as someone who, to some extent, was outside of the Silicon Valley tech scene, at least one First started. I do wish, sort of, there were less gatekeepers, or it was, sort of, more open, and people were more excited to talk about tech than they're not.

AI assessment note: “I do wish, sort of, there were less gatekeepers, or it was, sort of, more open”

Q Well, that is very, very kind of you, and an ego boost for me is always welcome, but I do want to kick off with a little bit on you, so tell me, I hear the dulcet British tones lurking beneath there, so how did you make your way into the world of tech, and how did you come to found Retools?

A Yeah, it's funny. So I actually grew up in Palo Alto, actually, but during high school, somehow it got the idea in me that I wanted to study philosophy, and so my parents weren't really a big fan of philosophy, and so they recommended that maybe I paired it with something else, perhaps, you know, computer science or something like that, basically, and then I was like, well, computer science sounds kind of interesting. Let's go take a look and see what's out there, and then I actually founded sort of a, a degree, actually, in the UK, at Oxford, that is both philosophy and computer science together, and it's actually one degree, which is really interesting, and that is Pretty much the only reason why I ended up in the UK for three years from undergrad, but it was so much fun.

AI assessment note: “parents recommended that maybe I paired it with something else, perhaps, you know, computer science”

Q think about when's the right time to double down? And what I mean by that is like, I often see very optimistic founders who go, it's working, it's working. And actually they're We've had three days of positive CAC data, and it's not exactly a sustainable indicator that Facebook is going to be this incredible kind of positive ROI channel moving forward. So what's enough to make you go yes?

A Yeah. So this is an interesting personality trait. I think I'm always, well, I think overall I'm fairly realistic. Maybe I'm too realistic, actually. That's problematic sometimes. I think up until maybe three Three, maybe four million dollars in ARR. I, I don't think even up to three or four million dollars in ARR, I was fairly convinced we did not have product market fit. I was thinking that, you know, every customer we sell, you know, this guy must be really weird. I can't believe he's using Retool. It doesn't make any sense, but he's buying Retool, you know, let's celebrate, but, you know, we don't have product market fit yet. And it was only maybe, I think we hit, I'm trying to remember, maybe a few hundred, maybe a thousand, you know, a few thousand, something like that, customers, where it was fairly clear that, you know, probably we do have product market fit now. Probably. And so, I think to answer your question, I think sort of being fairly pessimistic or being sort of fairly realistic about things is quite helpful in doing a startup. I think of most of these sort of really great founders I know, almost all of them are at least realistic with themselves. I think many are maybe, let's say, quite optimistic when talking to the press, talking to investors or whatever else. I think that's an important quality as well, but I think incredibly critical that you are very criti…

AI assessment note: “up to three or four million dollars in ARR, I was fairly convinced”

Q Got you. No, I mean, listen, I love that. As I said, I welcome any British accent. How did then, like, philosophy and CS degree at Oxford, how did that lead to retool?

A Yeah, ok, so this is kind of a, you know, a long story at this point. It's a bit of a detour, and so what happened was when I was in Oxford, I was American, and so one of the major, I was working on a bunch of side projects, Basically. And one of the major side projects that we ended up working on was basically something like a clone of Venmo, basically, for the UK. Because, I mean, as you know, in the UK, you send money via faster payments, probably. You know, you use an account number, you use a sort code. And I remember back, you know, when I was an undergrad there, this must have been 2013 or so, 2014, something like that, the mobile apps were actually pretty bad. And so, if you use, let's say, Santander or Barclays or whatever else, it was actually quite difficult to send money back. And so to me, this seemed, you know, enormously stupid. You know, clearly this is something that tech, you know, it's not that hard to solve. It's changing sort of a number of the database and moving some money back and forth. How hard could that be? And so we decided to start working on basically a clone of Venmo, basically. That actually went reasonably well. It actually got a bunch of users, and we actually got into YC doing that. But then it turns out it's actually a terrible business in the sense that every time someone sends money, we were losing money. And so the faster we grew, the mor…

AI assessment note: “when I was in Oxford, I was working on a bunch of side projects”

Q think about when's the right time to double down? And what I mean by that is like, I often see very optimistic founders who go, it's working, it's working. And actually they're We've had three days of positive CAC data, and it's not exactly a sustainable indicator that Facebook is going to be this incredible kind of positive ROI channel moving forward. So what's enough to make you go yes?

A Yeah. So this is an interesting personality trait. I think I'm always, well, I think overall I'm fairly realistic. Maybe I'm too realistic, actually. That's problematic sometimes. I think up until maybe three Three, maybe four million dollars in ARR. I, I don't think even up to three or four million dollars in ARR, I was fairly convinced we did not have product market fit. I was thinking that, you know, every customer we sell, you know, this guy must be really weird. I can't believe he's using Retool. It doesn't make any sense, but he's buying Retool, you know, let's celebrate, but, you know, we don't have product market fit yet. And it was only maybe, I think we hit, I'm trying to remember, maybe a few hundred, maybe a thousand, you know, a few thousand, something like that, customers, where it was fairly clear that, you know, probably we do have product market fit now. Probably. And so, I think to answer your question, I think sort of being fairly pessimistic or being sort of fairly realistic about things is quite helpful in doing a startup. I think of most of these sort of really great founders I know, almost all of them are at least realistic with themselves. I think many are maybe, let's say, quite optimistic when talking to the press, talking to investors or whatever else. I think that's an important quality as well, but I think incredibly critical that you are very criti…

AI assessment note: “up until maybe three Three, maybe four million dollars in ARR”

Q you, though, and it's a big one for me, which is, like, when you think about pivots, like, how do you think about giving it enough time to get enough Because we often hear that best founders follow their vision through the toughest of times. How do you think about sticking to the vision versus actually just reacting to when something's not a good business or doesn't have the demand?

A Yeah, so I think conviction is very important, and so I think when choosing ideas, I think conviction probably is sort of highest order you have to care about, basically, is do you actually get convicted about the idea? I have a bunch of friends now, and I'm sure you have many too, and maybe sort of seen many of these as investments, where people don't really know what to work on, and so what they do is they just sort of Throw 10 ideas against the wall, they go build 10 landing pages, and they go buy AdWords for 10 of them, and sort of see what does best. I think that very rarely works. The only case where I know this might potentially have worked was, uh, I think it was paloaltodelivery.com or something, which then became DoorDash. I think it's the only sort of recorded case of this ever actually working, but if you look at all the other sort of major companies like Airbnb, Stripe, etc., I think all of them were sort of very conviction-based. That said, I think when you have conviction, you also have to be fairly open-minded regarding what is and what isn't going well, and so it's funny you mentioned this because it brings me to a story. When we were working on the sort of demo clone for the UK, I think I would say we were fairly sort of hard-headed and fairly convicted that it was going to work, right, and, you know, despite sort of, you know, the fact that we're losing boatl…

AI assessment note: “when you have conviction, you also have to be fairly open-minded regarding what is”

Q Wow, that is a lot of credit to give to it. Next one. What would you most like to change about the Silicon Valley tech scene?

A Silicon Valley texting is quite insular. It's funny you ask this, because to some extent, I suppose the texting in the UK, texting in the UK is definitely smaller, but it's actually, I think, much more positive and uplifting to some extent. I think, you know, the rest of British culture maybe not, but the texting actually is, because when you run into someone who is in tech in London, it's so exciting, you know, you're sort of so pleased to see them, and you can always sort of connect or bond about something. Right, and you want to talk with them. Whereas in San Francisco, or in Silicon Valley, you know, everyone works in tech, and so it's not special to work in tech. You know, if anything, all my friends are telling me they don't want to have more tech friends. They want to find non-tech friends, you know, and I think that's a little bit sad. I think that sort of tech has got such a bad rap in Silicon Valley, but also that the, I think the culture is quite insular, and to some extent, this is why YC works, because YC can sort of bring you into the fold, sort of get you connected very quickly into the tech scene, but I do wish as someone who, to some extent, was outside of the Silicon Valley tech scene, at least one First started. I do wish, sort of, there were less gatekeepers, or it was, sort of, more open, and people were more excited to talk about tech than they're not.

AI assessment note: “I do wish, sort of, there were less gatekeepers, or it was, sort of, more open”

Q you, though, and it's a big one for me, which is, like, when you think about pivots, like, how do you think about giving it enough time to get enough Because we often hear that best founders follow their vision through the toughest of times. How do you think about sticking to the vision versus actually just reacting to when something's not a good business or doesn't have the demand?

A Yeah, so I think conviction is very important, and so I think when choosing ideas, I think conviction probably is sort of highest order you have to care about, basically, is do you actually get convicted about the idea? I have a bunch of friends now, and I'm sure you have many too, and maybe sort of seen many of these as investments, where people don't really know what to work on, and so what they do is they just sort of Throw 10 ideas against the wall, they go build 10 landing pages, and they go buy AdWords for 10 of them, and sort of see what does best. I think that very rarely works. The only case where I know this might potentially have worked was, uh, I think it was paloaltodelivery.com or something, which then became DoorDash. I think it's the only sort of recorded case of this ever actually working, but if you look at all the other sort of major companies like Airbnb, Stripe, etc., I think all of them were sort of very conviction-based. That said, I think when you have conviction, you also have to be fairly open-minded regarding what is and what isn't going well, and so it's funny you mentioned this because it brings me to a story. When we were working on the sort of demo clone for the UK, I think I would say we were fairly sort of hard-headed and fairly convicted that it was going to work, right, and, you know, despite sort of, you know, the fact that we're losing boatl…

AI assessment note: “when you have conviction, you also have to be fairly open-minded”

Q Well, that is very, very kind of you, and an ego boost for me is always welcome, but I do want to kick off with a little bit on you, so tell me, I hear the dulcet British tones lurking beneath there, so how did you make your way into the world of tech, and how did you come to found Retools?

A Yeah, it's funny. So I actually grew up in Palo Alto, actually, but during high school, somehow it got the idea in me that I wanted to study philosophy, and so my parents weren't really a big fan of philosophy, and so they recommended that maybe I paired it with something else, perhaps, you know, computer science or something like that, basically, and then I was like, well, computer science sounds kind of interesting. Let's go take a look and see what's out there, and then I actually founded sort of a, a degree, actually, in the UK, at Oxford, that is both philosophy and computer science together, and it's actually one degree, which is really interesting, and that is Pretty much the only reason why I ended up in the UK for three years from undergrad, but it was so much fun.

AI assessment note: “Pretty much the only reason why I ended up in the UK for three years”

Q Can I ask one final one? I promise it's the final one, but it's like, when I listen to you, everything is so rational, methodical, logical, and it's also so calm. Do you ever lose your shit? And how do you deal with, like, shit hit the fan moments? What's your coping mechanism? Hmm. Like, I lose my shit a lot.

A Yeah, yeah, yeah. Thanks for admitting that. I maybe lose my shit maybe once a year or something on average. It's not that frequent. I think part of it also is a SaaS company is just fairly stable in the sense that nothing really goes that wrong, really, for us. Hmm. Yeah, I'm trying to think of a better answer for this. We might want to cut this one. Yeah, I'll think about it for a bit longer. Maybe we can return to that at the end of the episode or something where I can try to give you a better answer. That's interesting. Yeah, so instead of having, let's say, a particular sort of very acute feeling of losing my shit, it is really existential angst, maybe, that keeps me sort of this dull thudding pain that Rather than sort of this acute, you know, sudden pain. And the funding pain really is, I think we're not moving quickly enough. I think, you know, Retool should be operating substantially faster as a company in all areas. I think, you know, in sales, marketing, engineering, everything. I think, you know, to be clear, we're moving pretty quickly for a small team of . . . Faster. I think it's actually surprisingly sustainable as long as the progress is really being made. I think if you try to really increase the clock speed and sort of cadence at which you move, but there are no results, I think that leads to burnout very quickly. At least for me, and potentially for you as w…

AI assessment note: “I maybe lose my shit maybe once a year or something on average.”