20VC: Segment Founder Peter Reinhardt on His Learning Process, How Great Leaders Listen and Encourage Debate within Their Organisation & How To Use Data Intelligently To Improve Decision-Making

Peter Reinhardt is the Founder and CEO @ Segment, the leading customer data platform with over 20,000 companies using Segment to collect, clean, and control their customer data. Prior to their $3.2BN acquisition by Twilio in 2020, Peter raised over $283M for Segment from Accel, Thrive, Meritech, GV, General Catalyst and Kleiner Perkins to name a few. Peter is also an active angel investor having made investments in the likes of Retool, Newfront, Pilot and more. In Today’s Episode with Peter Reinhardt You Will Learn: 1.) How Peter made his way into the world of startups and how he came to found a company, Segment, by actively trying to prove to his co-founder that it would not work? Why does Peter believe the Airbnb story is the most destructive myth for founders to follow? 2.) Learning: How does Peter think about learning frameworks for new topics? How does he construct his? How does Peter use data within this learning process to increase his rate of learning? Where do the majority of people go wrong in constructing their framework for learning? 3.) Listening and Debate: What does Peter believe is required to be "a good listener"? What questions do the best listeners ask? What tone do they use to ask these questions? How does Peter create an environment of safety internally where people feel they can debate? How does one balance between debate and thinking vs putting those thoughts into action? 4.) Problem-solving: How does Peter breakdown problems into their component parts? Through what mechanism does he determine what to prioritise first? How would Peter describe his decision-making process? How does he determine between head vs heart in decisions? In what way does Peter use data to further inform the decisions he makes? 5.) How would Peter describe his management style today? Has it changed over time? In what way has working with a coach changed the way Peter thinks about leadership? What elements do they focus on? How often does he see his coach? What have been some of his biggest takeaways? Item’s Mentioned In Today’s Episode with Peter Reinhardt Peter’s Favourite Book: The Chalice and the Blade, Crucial Conversations As always you can follow Harry and The Twenty Minute VC on Twitter here!

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  You are listening to 20 VC with me, Harry Stebbings, and I want to dive straight into the show today. Last year, this founder sold their company for a reported $3.2 billion, having scaled the team to over 500 people and some of the biggest and best companies as customers. My favorite part of this story, it is the only founding story I've known where the founder founded the company by trying to kill the idea. I've given enough away already, though, so with that, I'm thrilled to welcome Peter Reinhardt, co-founder and CEO at Segment, the leading customer data platform with over 20,000 companies using Segment to collect, clean, and control their customer data. Prior to their $3.2 billion acquisition by Twilio in 2020, Peter raised over $283 million for Segment from Excel, Thrive, Meritech, GV, General Catalyst, and Kleiner Perkins, to name a few.

• 0:45Harry Stebbings?

  Peter's also an active angel investor, having made investments in the likes of Retool, Newfront, Pilot, and more. And I do also want to say a huge thank you to Vas at Excel, Ravi at Newview, and Rob Ward at Meritech for some fantastic question suggestions today. I really did appreciate that. But before we dive into the show today, did you know that more than 80% of US public stock is owned by just 10% of Americans? This divide is even greater in the private markets. Carter makes it as easy to issue equity to your employees as it is to issue payroll, and for employees, as easy to accept it, too. More than 16,000 companies issue equity to their employees through Carter. Whether you're just getting started or getting ready to go public, the team at Carter can help. Check them out at Carter.com. And then another incredible product you have to introduce is SecureFrame.

• 1:30Harry Stebbings?

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• 2:14Harry Stebbings?

  So to learn more about the number one most active law firm representing VC-backed companies going public, head over to Cooley.com and also check out CooleyGo.com. That is enough from me though, so now I'm very, very excited to hand over to the one and only Peter Reinhardt, co-founder and CEO at Segment.

• 2:36Speaker 01

  You have now arrived at your destination.

• 2:39Harry Stebbings?

  Peter, this is such a joy to do. I've heard so many great things. We obviously had our great show many years ago now, but thank you so much for joining me once again today.

• 2:46Speaker 02

  Yeah, thanks so much for having me.

• 2:48Harry Stebbings?

  Not at all, but I spoke to Rob Ward before the show at Maritex, and he said we had to start on the founding story as 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?

• 3:02Speaker 02

  Yeah, so this is back in 2011. We left school and decided to do Y Combinator, and 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 their 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 of 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,

• 3:44Speaker 02

  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 so 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 Analytics JS, and it took data off of our website and sent it through to our analytics tool and Google Analytics and a few others, because we wanted to test them all in parallel." And he's like, "I think there's a big business behind Analytics JS, this little open source library." And this is when I tried to kill it. That is literally the worst idea I've ever heard. Like, it's an open source library. It's a hundred lines of code. Like, you gotta be kidding me. There is no business behind that.

• 4:27Speaker 02

  So I was like, I have to kill this. This will be the end of the company. We only have like six months of runway left. If I don't kill this, then like, we're done. So I went home and was like, okay, how do I kill this as fast as possible? Eventually, came the next day and I was like, all right, guys, here's what we're gonna do. We're gonna build a beautiful landing page. We're gonna put it up on Hacker News that pitches the value of Analytics JS. And we'll see what happens. And I was like, this will definitely kill it. Nothing ever does well on Hacker News. So we built the landing page, posted it up, and I was just wrong. We just went straight to the top of Hacker News, got hundreds of upvotes, thousands of stars on GitHub, thousands of email signups. People were reaching out to us on LinkedIn demanding access to a beta version of a hosted open source library. Which didn't exist, but we were pitching. So the whole thing just kind of blew up. So yeah, I tried to kill it.

• 5:08Speaker 02

  And in the process of like testing it, basically, trying to give it an honest test that would kill it, accidentally proved the opposite.

• 5:15Harry Stebbings?

  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?

• 5:31Speaker 02

  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.

• 6:07Harry Stebbings?

  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?

• 6:18Speaker 02

  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 think 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 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,

• 7:02Speaker 02

  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.

• 7:19Harry Stebbings?

  Through the iteration process, one learns a lot. And it was when I was speaking to Rob again at Maritac. 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?

• 7:35Speaker 02

  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

• 8:20Speaker 02

  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.

• 8:28Harry Stebbings?

  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 at Segment?

• 8:48Speaker 02

  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 and goals and measures, 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.

• 9:32Speaker 02

  And those are the two ways of doing it is either like sort of honey badger your way into the information and go deep or black box it and measure it around the outside and don't bother.

• 9:40Harry Stebbings?

  I mean, at the end of the day, you have to 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?

• 10:02Speaker 02

  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? 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.

• 10:43Speaker 02

  And I think clarity is usually what large organizations or teams in general are kind of most starved for.

• 10:50Harry Stebbings?

  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.

• 11:00Speaker 02

  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 per my earlier kind of suggestion about reading or going depths 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 of facts. So you hear a couple of 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.

• 11:44Speaker 02

  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 bizarre battles and making poor decisions, I think.

• 12:04Harry Stebbings?

  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?

• 12:21Speaker 02

  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 trying to make a decision based on the narrative is when you get into trouble.

• 13:03Harry Stebbings?

  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?

• 13:20Speaker 02

  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.

• 13:54Harry Stebbings?

  No, I'm totally with you. Speaking of emotional intensity, often internally it can come out in the form of debates and discussions. Crucial to any kind of intellectual progression in a lot of ways. You've got to also create that environment where debate and dissent is not only like welcome, but also encouraged. How do you think about doing that? Because it's not an easy thing to do.

• 14:13Speaker 02

  Yeah, I think I could do a better job of this. I think sometimes being just silent and waiting is actually extremely effective. There are some other leaders that I look up to that do this actually quite well, like literally just sitting in silence. And like people are really uncomfortable with it and eventually the discomfort of sitting in silence overcomes. The discomfort of saying whatever it is that they didn't want to say or didn't think they should say or whatever. Silence is a powerful tool.

• 14:36Harry Stebbings?

  No, I'm totally with you. I think you've got to get really like comfortable in silence, especially when it comes to a lot of negotiations. It's something that I've learned the painful way over time. In terms of like problem solving, which is, you know, at the core of a lot of debates and decision making, I spoke to Vass at Excel. And he said, again, I mean, you seem to be pretty world class at quite a number of these different skills. So clearly you've impressed your cap table immensely on numerous different levels. But he said, in terms of your problem solving skills, you're unique. How do you break down problems to their component parts? And do you have some form of structure or process in how you approach problem solving?

• 15:10Speaker 02

  I think I would describe it slightly differently. I think most problems actually have fairly obvious solutions if you have the necessary information in front of you. Like, I think rarely is the problem itself so complicated that you actually need to sit there with like a math proof. Like, sometimes you might need to achieve quiet or something to like feel a subtler kind of aspect of a problem. But like rarely do you actually have such a complicated intellectual pursuit that you actually really have to sit there for a really long time smashing your head against the wall. So most of the time, you either need quiet so that you can just feel what your intuition is really telling you, or you're missing information. And if you're missing information, the answer again is depth first. Just go rapidly search and find information that is relevant to the problem at hand. So I think speed to depth of information usually wins and generates great results.

• 15:54Speaker 02

  And that's something I try to interview for is how fast can someone go get information that is relevant to a problem? And are they resourceful in finding information about it?

• 16:02Harry Stebbings?

  How do you test for that? Because I agree with you in terms of speed to depth, but how do you test for that in an interview process?

• 16:07Speaker 02

  Usually it's about asking, one, what the most impressive thing is that they have done recently? And then working back into their process for how it is that they figured out that that was the right thing to work on and how they figured out what the solution was. And you kind of find out, did it take them a long time to figure it out? Or did they figure out quite quickly? And how did they figure it out?

• 16:25Harry Stebbings?

  In terms of the information itself, you know, I think a lot of founders struggle with information overload, especially when it comes to investor advice and the input that they have. I'm intrigued, how do you determine the information and advice to ingest versus which to reject? Often VCs say, oh, 5% of what I say you should listen to and 95% you shouldn't. How do you think about that ingest versus reject on information ingestion?

• 16:47Speaker 02

  I would prefer to just ingest as much as possible. I find that I'm time bound as opposed to anything else. So it's more like a prioritization as opposed to like trying to figure out which 5% to reject. Like, I don't know, just read more. Like, if there's bad data in there, then you can usually overwhelm that by just more and more data. You can tell my predisposition here is just more information, more information, more information.

• 17:07Harry Stebbings?

  Yeah, I can tell. Listen, I do agree with you in many respects. Again, it was Robert Meritak 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?"

• 17:21Speaker 02

  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 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'd achieved in the first part of my life of going to MIT and getting into Y C and all these things. And I was like, oh, well, like, here's how I think the world should work in terms of classrooms. 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, 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's like, three times in a row, I was just like, straight wrong.

• 18:04Speaker 02

  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.

• 18:09Harry Stebbings?

  It is 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 in leadership?

• 18:25Speaker 02

  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 direct reports 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.

• 19:00Harry Stebbings?

  Where do you feel you've personally grown a lot over the last year?

• 19:03Speaker 02

  In an acquisition, you're handing over the reins of control ultimately for the thing that you built. In this case, something that I spent a decade building and handing over the ultimately ultimate control of that to other folks that in this case I trust and I'm super impressed by. I think that's yet another lesson in humility, actually, of that that's the right thing to do in a certain situation.

• 19:24Harry Stebbings?

  Did you always know it was the right thing to do?

• 19:26Speaker 02

  No, you know, it took Jeff about eighteen months to convince me that it was the right thing to do.

• 19:30Harry Stebbings?

  What did he say that made you convinced inflecting your decision?

• 19:35Speaker 02

  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 was ultimately what's compelling. I'm a long shareholder, so I believe in it.

• 20:10Harry Stebbings?

  In terms of like, you know, the personal growth element, where would you like to personally grow over the next 12 to 18 months? Do you have like areas where you're like, you know what, on reflection, I'd like to spend some more time on this?

• 20:21Speaker 02

  Yeah, one area that I'm working on is being a better coach for my leaders. Like, I tend to either inspect deeply or give them sort of total free rein in their area. And I think there's a middle ground of engagement that is helping them more continuously kind of get coached through whatever challenges I'm seeing in their organization. So that's an area that I'm spending time on with my coach is figuring out how to coach my people.

• 20:44Harry Stebbings?

  What does that journey look like for you then in becoming a better coach with your coach? I mean, first, like, how often, if you don't mind me asking, how often do you see your coach? And then I guess, what framework does one put in place to become a better coach with your coach? This is so meta.

• 20:57Speaker 02

  Yeah, I meet with him once every two weeks for an hour. The main transition for me is figuring out how to ask the right questions of my leaders such that they're the one actually doing the intellectual effort and figuring out of what it is that they need to change and making them responsible for making that change themselves as opposed to me being responsible for that change. So for example, let's say someone needs to learn how to delegate better. I can say, hey, you know, you're doing great in all these areas, but there's one thing that's holding you back here, which is that I don't think that you're delegating enough to your team. One, do you agree with that feedback? And two, walk me through how you think you're going to get better at that and come back in two weeks with a plan. Two weeks later, ask, well, what did you experiment on? To practice getting better at delegation this week.

• 21:42Speaker 02

  I don't expect to be perfect right away, but I do expect to be making changes and practicing. Did it work? Did it not? What's your reflection? What are you going to do next week? So like those kinds of questions that help someone think through their own solution to their problem and take ownership of their own thing that they need to change. It's a nuanced skill. It's like how to guide someone. It's not an intuitive thing, but at least for me, not naturally.

• 22:02Harry Stebbings?

  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 the leader often goal setting?

• 22:20Speaker 02

  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.

• 23:02Harry Stebbings?

  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 tech crunch article. When it happened for you, how did it feel?

• 23:14Speaker 02

  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 up.

• 23:52Harry Stebbings?

  I'm really pleased that it has settled on that. On that very positive note, I do want to take it into a quickfire round, Peter. So I say a short statement and you give me your immediate thoughts. Does that sound okay?

• 24:01Speaker 02

  Let's do it.

• 24:02Harry Stebbings?

  So from your information ingestion questions and answers, I can tell you're a reader. What's the favorite book and why?

• 24:07Speaker 02

  Most recently, a book that I read by accident because it happened to be in the shared Kindle library with my mom, which is The Chalice and the Blade. It's a book by a famous feminist from the eighties, I think. Sort of totally rewrote my understanding of gender dynamics and the religious and cultural history of the West. Super interesting.

• 24:24Harry Stebbings?

  Tell me, question from Vas. What are your climate change ambitions?

• 24:28Speaker 02

  I helped start a company called Charm Industrial that is actually now the world's largest carbon removal operator. And so I hope we can get it to a gigaton of CO2 per year kind of scale.

• 24:38Harry Stebbings?

  What do you know now that you wish you'd known when you started Segment?

• 24:41Speaker 02

  Sales process. Unbelievably important in scaling a company after 10 million in revenue.

• 24:46Harry Stebbings?

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

• 24:52Speaker 02

  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, I 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.

• 25:33Speaker 02

  But that sales process drives efficiency and effectiveness and I think is like a crazy powerful tool that I totally did not understand in the early days.

• 25:40Harry Stebbings?

  Is that a sales process or is that customer discovery?

• 25:42Speaker 02

  The number one part of a sales process is discovery, so.

• 25:47Harry Stebbings?

  Okay, tell me, what three traits would you most want your children to adopt?

• 25:51Speaker 02

  Focus and then curiosity and humility.

• 25:53Harry Stebbings?

  What's the biggest misnomer about being acquired?

• 25:56Speaker 02

  I think that it's the end, ever beginning just needs an end to get started.

• 26:00Harry Stebbings?

  Tell me, the best board member that you've worked with and why?

• 26:03Speaker 02

  I think every board member is super unique and brings like different superpowers to the table. And that's actually how you assemble a board, right? You assemble a board specifically to put different superpowers around the table. That said, I will never forget Kim Hammond's first board meeting. Five minutes in, she interrupted my presentation to like, hold me accountable for something. And it was like, no one had ever interrupted the presentation before and no one had ever quite held me accountable in that way before in the board. It set a tone, which was awesome. So I'll never forget that.

• 26:29Harry Stebbings?

  I mean, it's a good and it's a daunting moment at the same time. I do want to finish it with probably the most important of all, which is what does that is five years old for you and for Sigmund Peter? How do you think about that?

• 26:39Speaker 02

  What does it hold for us up until the right? I think Twilio and Sigmund is a crazy cool combination and lots more to announce there in months ahead.

• 26:46Harry Stebbings?

  Peter, I've so enjoyed this. I hope that my question asking has got better since we last did it. I certainly like love doing it. So thank you so much for doing this.

• 26:54Speaker 02

  Thanks for having me.

• 26:57Harry Stebbings?

  Absolutely loved doing that show with Peter and I have to say I couldn't be more excited by the combination of Sigmund and Twilio. If you'd like to see more from us behind the scenes, you can of course on Instagram at H Stabbings 1996 with two Bs. However, before we leave you today, did you know that more than 80% of US public stock is owned by just 10% of Americans? This divide is even greater in the private markets. Carter makes it as easy to issue equity to your employees as it is to issue payroll. And for employees, as easy to accept it too. More than 16,000 companies issue equity to their employees through Carter. Whether you're just getting started or getting ready to go public, the team at Carter can help. Check them out at Carter.com. And then another incredible product you have to introduce is SecureFrame.

• 27:38Harry Stebbings?

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• 28:22Harry Stebbings?

  So to learn more about the number one most active law firm representing VC-backed companies going public, head over to Cooley.com and also check out Cooleygo.com. As always, I so appreciate all your support and I can't wait to bring you two phenomenal episodes next week.