The Exchanges

Q Not at all, but I spoke to Rob Ward before the show at Meritech, and he said we had to start on the founding stories. It's the only founding story that involved, in his words, a founder founding something by trying to kill it. So what does he mean by that, and what's the founding story?

A Yeah, so this is back in 2000... We left school and decided to do Y Combinator, and we, we got into Y Combinator with this idea for a classroom lecture tool, and the idea was to give students this button to push to say, I'm confused, and the professor would see this graph over time of how confused those students were. We were super excited about this, built way too much code over the summer of YC, raised a little bit of money coming out of YC Demo Day, and then we started deploying this classroom lecture tool into classrooms in Boston, all over the universities there, and it was a total disaster. Professors weren't really using it. The students, as soon as they opened their laptops to push the I'm confused button, just like went to Facebook and so on. So it was a total disaster. So then we spent about a year trying to build an analytics tool because we felt like we should have been able to figure out that this was a problem in some of our beta tests over the summer, and we didn't feel like our analytics tools had supported that. So then we spent about a year building an analytics tool, and we had this big grand vision, just like we'd had a big grand vision for classrooms, and like ultimately no one really cared, and we couldn't get traction with it. So then my co-founder Ian had this idea. He's like, well, you know, we wrote this little JavaScript library for our own use called…

AI assessment note: “And this is when I tried to kill”

Q Through the iteration process, one learns a lot, and it was when I was speaking to Rob again at Maritech, he said in terms of learning, you're one of the most impressive thinkers and fastest learners that he's ever encountered. Can I ask, how do you think about learning frameworks for new topics and new projects, and how do you construct yours?

A I guess the way I approach things is very depth first. I think using a narrow curiosity to maximum benefit to just go insanely deep, In an area. So like, for example, if I have a meeting on diversity, equity, and inclusion, I'll go try to like read a few pieces of published literature in a random area of diversity, equity, and inclusion that I find interesting. Or if I'm like having a discussion about a data product or something, I'll go like read a paper or two about what makes data tidy. Like there's a great one from the author of Language R. So I think like just going deeper into these things at every opportunity, if you kind of have a curiosity about it, you actually don't have to go that far. I find before you get a pretty significantly deeper understanding than most of the rest of the people that you'll encounter, and that depth generates much more interesting conversations and generates kind of better mental models for what's really going on. So I think depth first for me is like the fastest way to figuring out sort of reality and what's going on.

AI assessment note: “the way I approach things is very depth first.”

Q Not at all, but I spoke to Rob Ward before the show at Meritech, and he said we had to start on the founding stories. It's the only founding story that involved, in his words, a founder founding something by trying to kill it. So what does he mean by that, and what's the founding story?

A Yeah, so this is back in 2000... We left school and decided to do Y Combinator, and we, we got into Y Combinator with this idea for a classroom lecture tool, and the idea was to give students this button to push to say, I'm confused, and the professor would see this graph over time of how confused those students were. We were super excited about this, built way too much code over the summer of YC, raised a little bit of money coming out of YC Demo Day, and then we started deploying this classroom lecture tool into classrooms in Boston, all over the universities there, and it was a total disaster. Professors weren't really using it. The students, as soon as they opened their laptops to push the I'm confused button, just like went to Facebook and so on. So it was a total disaster. So then we spent about a year trying to build an analytics tool because we felt like we should have been able to figure out that this was a problem in some of our beta tests over the summer, and we didn't feel like our analytics tools had supported that. So then we spent about a year building an analytics tool, and we had this big grand vision, just like we'd had a big grand vision for classrooms, and like ultimately no one really cared, and we couldn't get traction with it. So then my co-founder Ian had this idea. He's like, well, you know, we wrote this little JavaScript library for our own use called…

AI assessment note: “And this is when I tried to kill”

Q What did he say that made you convinced in fact in your decision?

A Yeah, it was the realization that the vision that he had for how Segments customer data and Twilio's communication channels came together in a way that was Very novel in the market, or could come together in a way that's very novel in the market, and that is extremely valuable for companies. And I think we've seen enterprise customers in particular get really excited about the combination as a result of kind of the direction that they see it going. But it took me a while to appreciate that there was sort of deep value behind that joint opportunity in a way that would be pretty hard to unlock for either company separately. So that is ultimately what's compelling. I'm a long shareholder, so I believe in it.

AI assessment note: “it was the realization that the vision that he had for how Segments customer data”

Q Can I ask, how do you think about, then, that balance between the pursuit of vision and that unwavering belief in what you're doing, versus actually just realizing when it's not hitting and you need to try something else?

A Yeah, I think one of the most destructive myths in Silicon Valley is the Airbnb story and myth, because the story is basically that they hung on and didn't have product market fit, and then just eventually things started going well, and they didn't really change that much, and, like, the whole thing kind of took off, and they, like, scrambled, and they made it work. And so there's, like, this idea that you should just hang on for years to your idea because, like, your vision is probably right. I think it's super destructive. There are some times when people's vision happens to match what the world is, Actually needs or what the world actually thinks it needs. But for the most part, like the world honestly couldn't care less what your vision is. It just doesn't care. And a business is about solving other people's problems. I think it's actually super important to set aside a vision until you actually understand what the world wants. And like, okay, if you started solving some problems for other people, which is what a business does, then the world starts to care about what you're doing. And if you amass sort of critical mass of like actually solving problems for folks, then I think you earn the right to tell them How you think it ought to be done, but I think that's a right that you earn, not a way to start a company.

AI assessment note: “set aside a vision until you actually understand what the world wants”

Q Can I ask one thing that I see maybe with first time founders or less experienced founders is kind of intensity of emotional responses. Something bad happens and it's very alleviated. And with more experienced founders, it's just much more muted. How do you think about your emotional responses to more intense or binary situations? And has that changed over time?

A Oh yeah, it's definitely changed. I've definitely gotten, like, more muted in my emotional responses to things. I've heard other founders and myself and my co-founders describe it as, like, you go through such emotional roller coasters all the time, it feels like your body learns to, like, bound your emotional response into a narrower and narrower range, which, like, is good and useful in the workday if you have to jump between, for example, doing a press interview and firing somebody. And you need to do that back to back. Like, you can't let the emotions of the two get in your way, right? So it's very useful, but I think it's just a natural outcome of spending an extended period of time in a roller coaster.

AI assessment note: “Oh yeah, it's definitely changed. I've definitely gotten, like, more muted”

Q Through the iteration process, one learns a lot, and it was when I was speaking to Rob again at Maritech, he said in terms of learning, you're one of the most impressive thinkers and fastest learners that he's ever encountered. Can I ask, how do you think about learning frameworks for new topics and new projects, and how do you construct yours?

A I guess the way I approach things is very depth first. I think using a narrow curiosity to maximum benefit to just go insanely deep, In an area. So like, for example, if I have a meeting on diversity, equity, and inclusion, I'll go try to like read a few pieces of published literature in a random area of diversity, equity, and inclusion that I find interesting. Or if I'm like having a discussion about a data product or something, I'll go like read a paper or two about what makes data tidy. Like there's a great one from the author of Language R. So I think like just going deeper into these things at every opportunity, if you kind of have a curiosity about it, you actually don't have to go that far. I find before you get a pretty significantly deeper understanding than most of the rest of the people that you'll encounter, and that depth generates much more interesting conversations and generates kind of better mental models for what's really going on. So I think depth first for me is like the fastest way to figuring out sort of reality and what's going on.

AI assessment note: “I guess the way I approach things is very depth first.”

Q How do you prevent your mind actively jumping from a limited set of data points to a narrative that's fully baked out? Do you have to kind of constantly do it like meditation, bring yourself back, bring yourself back? How do you think about not developing the narrative from the limited data set, which is just very human and natural?

A You can develop the narrative, but you need to verify it. So I think the intuition that comes with development of the narrative guides what your next question should be, right? So, okay, I have two data points. I think the narrative is this. Can you ask a question to try to verify whether or not that is actually what's going on? And what's the fastest way that you can unlock that data point? It may not be in an active conversation. It might be reading a doc or looking something up on the internet, but what's the fastest way that you can figure out whether or not that is actually what's going on or not. And until you verify that you can't respond emotionally. To the narrative that you've constructed. Basically what happens is most people get a few facts, construct a narrative, and then respond emotionally to the narrative as opposed to the facts. And when you respond emotionally to the narrative or try to make a decision based on the narrative is when you get into trouble.

AI assessment note: “You can develop the narrative, but you need to verify it.”

Q It's funny. It also teaches you a lot of humility. When you think about humility, how do you feel? And do you think it's changed a lot over the years? And do you think humility is actually important? Because we see, you know, great leaders today from Bezos to Musk who Probably wouldn't be described as humble. How do you think about humility and leadership?

A I think it's super important and basically a necessary precursor to continued growth, like personal growth, which is like, if you're not willing to admit that there's something wrong with the current you, then like, you're not going to change it, and so therefore you're not going to personally grow. I think if someone lacks humility, at least on some of those dimensions, yeah, they're not going to grow, so they're stagnant in their capacity, whatever that is. So to me, it's a huge warning sign, actually. If there's someone in the company or one of my directors Ports or something that's, like, not displaying humility. They're probably at their peak. They're not going to grow anymore, and that's a big red flag or yellow flag that, like, I need to start thinking about hiring over them.

AI assessment note: “I think it's super important and basically a necessary precursor to continued growth”

Q Can I ask, how do you think about, like, fear within organizations, especially around accountability? And, you know, with responsibility comes accountability, and you want people to go big and be bold, but you also don't want them to be scared of failing. How do you think about that very challenging relationship to balance with you as a leader, often goal setting?

A I think it's something that gets harder as an organization scales. And I'm not sure I have a good answer for it as an organization scales. I'm not sure that any organization has a good answer for it as it scales. But I think you want people to broadly sign up for the risk that they're taking or sign up for the upside of the thing that they're doing. And so the more that you can get a team to write down their own goals and kind of encourage and get them excited about the thing before you hold them accountable for it, I think is important. I think also recognizing and having an intuition for when a goal really was a stretch goal versus when a goal was really a table stakes goal, I think is really important. Like, if someone sets a stretch goal and you hold them accountable as if it was a table stakes, I think you have to have some intuition and balance for the emotional aspect of what really was behind the written goal.

AI assessment note: “recognizing and having an intuition for when a goal really was a stretch goal”

Q In terms of learning, I think a lot of founders today struggle with learning what really great looks like in specific roles where maybe they're not tailored or accustomed to, be it marketing for maybe more technical people and vice versa. How do you think about, like, scaling learning curves and understanding what great looks like in talent, especially in lessons when you were scaling that segment?

A Yeah, one way is to black box it and basically say, what is the outcome of great marketing? What's the outcome of great engineering? And measure the black box and not bother to inspect inside as to whether the box isn't, like, being done well internally, right? And that, I think, is a useful skill in its own right, is to, like, figure out how to set those kind of black boxy metrics. Because you can't always have the time to go deeply inspect. The other way is to find creative ways to go depth first, like find a creative way to go actually learn what a marketer does. If you're a founder doing interesting things, like a lot of people want to talk to you. And like, you can just leverage that into conversations to learn and share. I think if you just ask a lot of like, honestly, pretty aggressive questions to understand what a marketer does say, I think you'll find people are like willing to share that.

AI assessment note: “one way is to black box it... The other way is to find creative ways”

Q Can I ask one thing that I see maybe with first time founders or less experienced founders is kind of intensity of emotional responses. Something bad happens and it's very alleviated. And with more experienced founders, it's just much more muted. How do you think about your emotional responses to more intense or binary situations? And has that changed over time?

A Oh yeah, it's definitely changed. I've definitely gotten, like, more muted in my emotional responses to things. I've heard other founders and myself and my co-founders describe it as, like, you go through such emotional roller coasters all the time, it feels like your body learns to, like, bound your emotional response into a narrower and narrower range, which, like, is good and useful in the workday if you have to jump between, for example, doing a press interview and firing somebody. And you need to do that back to back. Like, you can't let the emotions of the two get in your way, right? So it's very useful, but I think it's just a natural outcome of spending an extended period of time in a roller coaster.

AI assessment note: “Oh yeah, it's definitely changed. I've definitely gotten, like, more muted”

Q Yeah, I can tell. Listen, I do agree with you in many respects. Again, it was Robert Maritek that said, in terms of unique skills, you never shy away from poking fun at yourself. His words. He asked, where did that life lesson come from, and do you think it's important?

A Yeah, I think it's important. I'm not sure that I was that way before we found product market fit, or before we started the company and kind of had the year and a half of failure. I think the thing that, just to go back to the founding story for a second, it was a very formative year and a half, two years for me. I came into it with, like, a lot of pride about what I achieved in the first part of my life of going to MIT and getting into YC and all these things, and I was like, oh, well, like, here's how I think the world should work in terms of classrooms, and I just got crushed. Like, it was just wrong. The world didn't care. That's a pretty eye-opening experience, and then we were like, oh, well, here's how analytics should work, and, like, the world does not care. And so then, you know, my co-founder was like, well, I think the world actually does want this. And I was like, no way. And then I was wrong. So it was like three times in a row. I was just like straight wrong. And you kind of have to laugh at yourself after that, especially when the third one ends up being successful, right? It's just funny.

AI assessment note: “Yeah, I think it's important. I'm not sure that I was that way before”

Q What did he say that made you convinced in fact in your decision?

A Yeah, it was the realization that the vision that he had for how Segments customer data and Twilio's communication channels came together in a way that was Very novel in the market, or could come together in a way that's very novel in the market, and that is extremely valuable for companies. And I think we've seen enterprise customers in particular get really excited about the combination as a result of kind of the direction that they see it going. But it took me a while to appreciate that there was sort of deep value behind that joint opportunity in a way that would be pretty hard to unlock for either company separately. So that is ultimately what's compelling. I'm a long shareholder, so I believe in it.

AI assessment note: “the vision that he had for how Segments customer data and Twilio's communication channels came together”

Q Can I ask, how do you think about, then, that balance between the pursuit of vision and that unwavering belief in what you're doing, versus actually just realizing when it's not hitting and you need to try something else?

A Yeah, I think one of the most destructive myths in Silicon Valley is the Airbnb story and myth, because the story is basically that they hung on and didn't have product market fit, and then just eventually things started going well, and they didn't really change that much, and, like, the whole thing kind of took off, and they, like, scrambled, and they made it work. And so there's, like, this idea that you should just hang on for years to your idea because, like, your vision is probably right. I think it's super destructive. There are some times when people's vision happens to match what the world is, Actually needs or what the world actually thinks it needs. But for the most part, like the world honestly couldn't care less what your vision is. It just doesn't care. And a business is about solving other people's problems. I think it's actually super important to set aside a vision until you actually understand what the world wants. And like, okay, if you started solving some problems for other people, which is what a business does, then the world starts to care about what you're doing. And if you amass sort of critical mass of like actually solving problems for folks, then I think you earn the right to tell them How you think it ought to be done, but I think that's a right that you earn, not a way to start a company.

AI assessment note: “super important to set aside a vision until you actually understand what the world wants.”

Q also listen intently. And that takes me to another element, which, you know, many of your investors said you were world class at, which is just actually your ability to truly listen and engage deeply on a listening level. My question and thoughts around that was like, how do you balance between listening and data ingestion versus action, orientation, putting things in process? How do you balance between the two?

A I think there's actually a little bit of a misnomer there that listening is somehow passive. I think good listening is not good listening. I think it's about reflecting back what you're hearing. So you just, for example, sort of communicate it as a dichotomy, if you will, between how do you ingest data versus take action? I actually think good listening, for example, would be like, well, why do you feel like those two things are separate? Do you feel like you can't do both at the same time? Like a good listener asks questions, clarifies, pushes for generating next steps. Like, well, how would you figure that out? When are you going to figure that out by? And so a good listener, I think actually Guides the person almost to the conclusions that you could spit back to someone, but guides them to the outcome and the next steps and clarity of what needs to happen next, and so I think listening actively like that actually generates clarity, and I think clarity is usually what large organizations or teams in general are kind of most starved for.

AI assessment note: “I think there's actually a little bit of a misnomer there that listening is somehow passive.”

Q How do you prevent your mind actively jumping from a limited set of data points to a narrative that's fully baked out? Do you have to kind of constantly do it like meditation, bring yourself back, bring yourself back? How do you think about not developing the narrative from the limited data set, which is just very human and natural?

A You can develop the narrative, but you need to verify it. So I think the intuition that comes with development of the narrative guides what your next question should be, right? So, okay, I have two data points. I think the narrative is this. Can you ask a question to try to verify whether or not that is actually what's going on? And what's the fastest way that you can unlock that data point? It may not be in an active conversation. It might be reading a doc or looking something up on the internet, but what's the fastest way that you can figure out whether or not that is actually what's going on or not. And until you verify that you can't respond emotionally. To the narrative that you've constructed. Basically what happens is most people get a few facts, construct a narrative, and then respond emotionally to the narrative as opposed to the facts. And when you respond emotionally to the narrative or try to make a decision based on the narrative is when you get into trouble.

AI assessment note: “You can develop the narrative, but you need to verify it.”

Q It's funny. It also teaches you a lot of humility. When you think about humility, how do you feel? And do you think it's changed a lot over the years? And do you think humility is actually important? Because we see, you know, great leaders today from Bezos to Musk who Probably wouldn't be described as humble. How do you think about humility and leadership?

A I think it's super important and basically a necessary precursor to continued growth, like personal growth, which is like, if you're not willing to admit that there's something wrong with the current you, then like, you're not going to change it, and so therefore you're not going to personally grow. I think if someone lacks humility, at least on some of those dimensions, yeah, they're not going to grow, so they're stagnant in their capacity, whatever that is. So to me, it's a huge warning sign, actually. If there's someone in the company or one of my directors Ports or something that's, like, not displaying humility. They're probably at their peak. They're not going to grow anymore, and that's a big red flag or yellow flag that, like, I need to start thinking about hiring over them.

AI assessment note: “I think it's super important and basically a necessary precursor to continued growth”

Q I do want to finish with one final question before the quickfire, and it's, you know, founders today, I think, idolize in so many ways the massive acquisition, the big exit, the big TechCrunch article. When it happened for you, how did it feel?

A An acquisition is a mix of every emotion, and then the question is, I mean, like literally, like you feel relief, you feel excitement, you feel sadness, you feel loss, like significant loss because you are losing control. Like every emotion under the sun I felt over the period of two weeks and like day by day was completely different. My impression is that pretty much every founder goes through that if this is the route that they go down. I think the question, more interesting question though, is where does it settle, right? Does it settle on a feeling of loss or does it settle on a feeling of excitement? For me, it's settled on a feeling of excitement of like the things that Segment and Twilio can go do together. And we'll announce more later this year at Signal and so on, but that feels really good to me that that's where it's ending at.

AI assessment note: “An acquisition is a mix of every emotion... you feel relief, you feel excitement”

Q Do you feel many CEOs today actively listen, as you just said, and was it always innate to you, or did you kind of learn to actively listen? Because I don't think that's like an innate Skill. Like, that's an incredible learn.

A I think most good leaders that I come across seem to do that, partly because they're low context on most things, and so the only way to figure out what's going on is to ask a lot of questions, myself included. But I think for my earlier kind of suggestion about reading or going depth first, I think the book that most changed how I think about listening is the book Crucial Conversations. The basic thesis is that most humans, by default, invent a narrative about what's going on based on a couple facts. So you hear a couple actual facts, But then you construct in your head an entire narrative for why that's the case. For example, you see someone driving slowly, and you see that you can't see anyone over the top of the backseat, and you're like, oh, it's some old person who's driving super slow and can't see the road, and you know, you like invent a whole narrative about what's going on. And it's actually generally not a good thing. So I think going depth first into like, well, maybe the person like can't see well right now because they just got out of an eye appointment, or like there's all kinds of reasons that someone could be driving slow. And so, like, actually trying to, having the intellectual curiosity to go figure out what those things are is really important. And in fact, if you just make those narrative assumptions, you kind of find yourself constantly in these, like, bi…

AI assessment note: “I think most good leaders that I come across seem to do that”

Q Well, I mean, I think it takes a great leader to admit they were wrong. Can I ask, you know, you mentioned the multiple elements that failed there before that insight. You know, it's tough. You write thousands of lines of code, commit many, many late evenings, many early mornings. How did you deal with it not working and the dejection? Was that tough?

A Yeah, super crushing. I think at one point I lost like 20 pounds or 10 pounds in like two weeks or something like that. I was going to the hospital for panic attacks. We just kind of glazed over that part, but like crushing. Yeah, actually the founders that I'm most impressed by and how they handled that were actually the Codecademy founders who were in our batch of Y Combinator. They started and killed, like, 12 ideas over the course of Y Combinator, and then three days before Demo Day launched Codecademy, and got to 300 and something thousand signups in the 72 hours before they presented at Demo Day. And they were, like, by far the hottest company in the batch. But they were just ruthless, killing off ideas that weren't working.

AI assessment note: “super crushing. I think at one point I lost like 20 pounds”

Q also listen intently. And that takes me to another element, which, you know, many of your investors said you were world class at, which is just actually your ability to truly listen and engage deeply on a listening level. My question and thoughts around that was like, how do you balance between listening and data ingestion versus action, orientation, putting things in process? How do you balance between the two?

A I think there's actually a little bit of a misnomer there that listening is somehow passive. I think good listening is not good listening. I think it's about reflecting back what you're hearing. So you just, for example, sort of communicate it as a dichotomy, if you will, between how do you ingest data versus take action? I actually think good listening, for example, would be like, well, why do you feel like those two things are separate? Do you feel like you can't do both at the same time? Like a good listener asks questions, clarifies, pushes for generating next steps. Like, well, how would you figure that out? When are you going to figure that out by? And so a good listener, I think actually Guides the person almost to the conclusions that you could spit back to someone, but guides them to the outcome and the next steps and clarity of what needs to happen next, and so I think listening actively like that actually generates clarity, and I think clarity is usually what large organizations or teams in general are kind of most starved for.

AI assessment note: “I think there's actually a little bit of a misnomer there that listening is somehow passive.”

Q Can you unpack that for me just a little bit? What is the core understanding revelation about sales?

A I came into segment thinking that sales was about flash and relationships and things like that. You can do great sales repeatedly without any of that, and it really comes down actually to depth first, asking the customer the questions of, well, what's the actual problem do you have? How much would you pay to solve that problem? Like pretty aggressive questions that like, as an engineer, you feel very weird and uncomfortable about asking. But when you actually engage that way with a company or someone who represents a company, they actually really enjoy it. You're like helping them think through the problem and think through, well, I don't know. Yeah. What is the ROI? Yeah, you're right. Maybe I should think through that. As you ask those questions, you become a partner for them and you naturally figure out how your solution is going to fit in or not. Either way is fine, but that sales process drives efficiency and effectiveness and I think it's like a crazy powerful tool that I totally did not understand in the early days.

AI assessment note: “it really comes down actually to depth first, asking the customer the questions”

Q Well, I mean, I think it takes a great leader to admit they were wrong. Can I ask, you know, you mentioned the multiple elements that failed there before that insight. You know, it's tough. You write thousands of lines of code, commit many, many late evenings, many early mornings. How did you deal with it not working and the dejection? Was that tough?

A Yeah, super crushing. I think at one point I lost like 20 pounds or 10 pounds in like two weeks or something like that. I was going to the hospital for panic attacks. We just kind of glazed over that part, but like crushing. Yeah, actually the founders that I'm most impressed by and how they handled that were actually the Codecademy founders who were in our batch of Y Combinator. They started and killed, like, 12 ideas over the course of Y Combinator, and then three days before Demo Day launched Codecademy, and got to 300 and something thousand signups in the 72 hours before they presented at Demo Day. And they were, like, by far the hottest company in the batch. But they were just ruthless, killing off ideas that weren't working.

AI assessment note: “Yeah, super crushing. I think at one point I lost like 20 pounds”