The Exchanges

Q When you think back to being the three-person team there compared to where you are today, you weren't the same leader then that you are today, and it's a much more mature leadership stance and standpoint. Were there inflection moments that changed how you thought about that leadership?

A I think first time I realized the need for that this is a continually evolving job. I remember the company was probably about 30 people, and I was really frustrated all the time. Like, it didn't seem to be working well. Anymore. And I remember I was talking to one of our investors, Albert Wenger from Union Square Ventures, and Fred Wilson, his partner, and I was talking to them, and I was like, event that they were holding. How's it going, Jeff? I'm like, well, honestly, it feels pretty crummy right now. Why is that? And I was explaining some of the things I was frustrated by, and they said, well, can you draw the org chart for me? And I said, oh, yeah, you know what? Yeah, I've never done that before, actually, because we're such a small company. You don't, you don't really think about org charts in those early days of a company. It just is what, like, you're just kind of running fast. So I go, okay, and I go up to the whiteboard. I'm like, okay, well, there's me, and then there's this one, and I'm, And I'm drawing each person, and it's a straight line with everybody reporting to me. It worked when we were three people, four people, five people, right? But at some point, we reached this tipping point where, like, you needed an org chart that wasn't just a straight line to help make sense of things and to make progress. And so I remember drawing this thing, and I'm kind of, as …

AI assessment note: “it was the first time I really had this realization of, like, oh, yeah”

Q When you think back to being the three-person team there compared to where you are today, you weren't the same leader then that you are today, and it's a much more mature leadership stance and standpoint. Were there inflection moments that changed how you thought about that leadership?

A I think first time I realized the need for that this is a continually evolving job. I remember the company was probably about 30 people, and I was really frustrated all the time. Like, it didn't seem to be working well. Anymore. And I remember I was talking to one of our investors, Albert Wenger from Union Square Ventures, and Fred Wilson, his partner, and I was talking to them, and I was like, event that they were holding. How's it going, Jeff? I'm like, well, honestly, it feels pretty crummy right now. Why is that? And I was explaining some of the things I was frustrated by, and they said, well, can you draw the org chart for me? And I said, oh, yeah, you know what? Yeah, I've never done that before, actually, because we're such a small company. You don't, you don't really think about org charts in those early days of a company. It just is what, like, you're just kind of running fast. So I go, okay, and I go up to the whiteboard. I'm like, okay, well, there's me, and then there's this one, and I'm, And I'm drawing each person, and it's a straight line with everybody reporting to me. It worked when we were three people, four people, five people, right? But at some point, we reached this tipping point where, like, you needed an org chart that wasn't just a straight line to help make sense of things and to make progress. And so I remember drawing this thing, and I'm kind of, as …

AI assessment note: “And that was just one moment I remember, but it was the first time”

Q British, and so I normally just skirt around anything at all, because we hate conflict. But Frank Slootman said the other day, diversity should not override marriage, and it was one that kind of struck me, and so I, and you said I disagree both privately and publicly on it. Can you unpack your thinking here, and how you think you as a leader have a role to respond, actually?

A Yeah, two things. First of all, I do disagree publicly and privately. What I was responding to mostly is he said, and like all the CEOs I talk to privately will say they agree with me on this. I'm like, well, how can you speak for every CEO? So I was really responding to is like, well, I just want to make sure that in my voice, I am clear. This is, I do not say something differently in public than I say in private. And you can ask anyone who I've talked to. That was the major thing that I was disagreeing with because Here's a high profile CEO who's saying, look, secretly everyone agrees with me. And I'm like, no, you can't say that because you just described that to me, even though we've never talked about this. In fact, I've never even met Frank. And so that's the thing that really made me feel obligated to say something in that moment. Now let's talk about why I wanted to say something. First of all, it is a straw argument that there's a choice between diversity and merit, right? If you were to say, well, look, I've got, you know, this person deserves a job, but this person is diverse. Clearly I have to pick the diverse. Like that does not How it actually works. That is not how it plays out in practice. Those are not the decisions that we make. I don't know what kind of recruiting process that would be or a promotion process, but the way it works in practice and in reality is…

AI assessment note: “that's the thing that really made me feel obligated to say something in that moment.”

Q In what way did you most want to break out of your jail that you were not able to do?

A Well, the thing that frustrated me, so our most successful product was our messaging product, right? And so as a messaging API, the, the crux of that product was three, was, was an API with three primary fields, right, if you will, like from to body. That's a text message. Who's it coming from? Who's it going to? And what does it say? That's a text message. And so we had millions of developers who integrated Twilio into their code and specified in their code a to, a from, and a body. Now in that world, How do you add more value to the customer over time? They specifically said, I want you to send a text message from this to this that says this. What do you do to add value? You're kind of in a box. And so if you look at the last, say, 10 years of Twilio, it was all about how do we add value? How do we create a product that allows us the expressiveness to go add value because the customer hasn't explicitly stated exactly what they want us to do, and therefore any deviation from that exact thing is called Failure by the customer. And so that's a lot of what we were always trying to do, is to create a surface area that allowed us more expression as a product team and as a company. You know, think about if you're a file storage company, you know, success is I stored your file and I didn't lose it, and failure is, oops, I lost your file, sorry. Like, and so you have to break out of t…

AI assessment note: “You're kind of in a box... it was all about how do we add value?”

Q familiarity. I do want to start on your leadership though, because, you know, I think bluntly, you know, when you look at your scaling from that, you know, first founder raising the pre-seed to where we are today in terms of the public market CEO that you are, it's a broad and terrible question. I have to admit. But it's really like, what does great leadership mean to you today?

A I think great leadership is really deciding what behaviors you want permeating your, let's say for a corporate leader, your organization, and then modeling those, of course, but then trying to create the framework whereby other people can understand why those are the behaviors that matter and create systems that continually reinforce those behaviors. And I think about companies that You know, we as human beings, we're tribal creatures, right? We survived for thousands of years in the wild because we formed tribes and we could accomplish more together than we could as individuals. And that's what really separates human beings from, you know, so many other species is our very advanced ability to collaborate. And that, like that tribal thinking is like deep in our brains. And so when you think about a company, what you're really creating is a tribe that people belong to, to accomplish something together. And if you think about all the tribes that we kind of affiliate with in our lives, right? We've got, you know, a tribe of schools that we went to. We've got tribes of the sports teams that we follow. We've got tribes of, you know, many people religion, right? These are all the, the belongings that like create our identity, even like brands that we like, right? The, you start to form a kind of a tribal belonging to all these groups. And like what creates a tribe, I think is really …

AI assessment note: “great leadership is really deciding what behaviors you want permeating your”

Q feel secure and safe To really pursue things, to go big, to build. How do you create an environment of safety and a culture where, yeah, Jeff, you can try that. That sounds really interesting that you've heard that from four customers. Give it a go. It's okay if it fails. How do you create that acceptability of failure, but not also accepting failure? Do you know what I mean?

A Yeah, I think the best that I've thought of, and we are imperfect at implementing this, but two things. Number one, you treat every one of those ideas as a hypothesis. As opposed to like, you know, a lot of companies you might say, oh, like, you know, somebody, especially someone highly paid has an idea and they say, I want you to go do this, right? That's not a hypothesis. That's an order. And then if you, you know, build whatever that thing is and you put it in front of customers and nobody cares, it's like, well, you know, it must've been bad execution, right? And that would be a career suicide for someone if that happens. They'll definitely start your career, right? And because it's certainly, it's not the executive's fault if the idea was bad. It was some underling who didn't do a good job executing it, right? Well, that's why customers don't want it because you didn't explain it right or you didn't build the right features. And so if instead you treat every idea, whether it comes from someone on the front line or the CEO of the company, you treat it as a hypothesis, and hypotheses then need to be tested, and they can be true or they can be false. So the work ahead is to prove the hypothesis true or false, and success is doing just that. Success is getting to a true or false as quickly and cheaply as possible. As hypotheses, the only failure mode is failing to prove it tru…

AI assessment note: “you treat every one of those ideas as a hypothesis”

Q familiarity. I do want to start on your leadership though, because, you know, I think bluntly, you know, when you look at your scaling from that, you know, first founder raising the pre-seed to where we are today in terms of the public market CEO that you are, it's a broad and terrible question. I have to admit. But it's really like, what does great leadership mean to you today?

A I think great leadership is really deciding what behaviors you want permeating your, let's say for a corporate leader, your organization, and then modeling those, of course, but then trying to create the framework whereby other people can understand why those are the behaviors that matter and create systems that continually reinforce those behaviors. And I think about companies that You know, we as human beings, we're tribal creatures, right? We survived for thousands of years in the wild because we formed tribes and we could accomplish more together than we could as individuals. And that's what really separates human beings from, you know, so many other species is our very advanced ability to collaborate. And that, like that tribal thinking is like deep in our brains. And so when you think about a company, what you're really creating is a tribe that people belong to, to accomplish something together. And if you think about all the tribes that we kind of affiliate with in our lives, right? We've got, you know, a tribe of schools that we went to. We've got tribes of the sports teams that we follow. We've got tribes of, you know, many people religion, right? These are all the, the belongings that like create our identity, even like brands that we like, right? The, you start to form a kind of a tribal belonging to all these groups. And like what creates a tribe, I think is really …

AI assessment note: “great leadership is really deciding what behaviors you want permeating your... organization”

Q feel secure and safe To really pursue things, to go big, to build. How do you create an environment of safety and a culture where, yeah, Jeff, you can try that. That sounds really interesting that you've heard that from four customers. Give it a go. It's okay if it fails. How do you create that acceptability of failure, but not also accepting failure? Do you know what I mean?

A Yeah, I think the best that I've thought of, and we are imperfect at implementing this, but two things. Number one, you treat every one of those ideas as a hypothesis. As opposed to like, you know, a lot of companies you might say, oh, like, you know, somebody, especially someone highly paid has an idea and they say, I want you to go do this, right? That's not a hypothesis. That's an order. And then if you, you know, build whatever that thing is and you put it in front of customers and nobody cares, it's like, well, you know, it must've been bad execution, right? And that would be a career suicide for someone if that happens. They'll definitely start your career, right? And because it's certainly, it's not the executive's fault if the idea was bad. It was some underling who didn't do a good job executing it, right? Well, that's why customers don't want it because you didn't explain it right or you didn't build the right features. And so if instead you treat every idea, whether it comes from someone on the front line or the CEO of the company, you treat it as a hypothesis, and hypotheses then need to be tested, and they can be true or they can be false. So the work ahead is to prove the hypothesis true or false, and success is doing just that. Success is getting to a true or false as quickly and cheaply as possible. As hypotheses, the only failure mode is failing to prove it tru…

AI assessment note: “Number one, you treat every one of those ideas as a hypothesis.”

Q British, and so I normally just skirt around anything at all, because we hate conflict. But Frank Slootman said the other day, diversity should not override marriage, and it was one that kind of struck me, and so I, and you said I disagree both privately and publicly on it. Can you unpack your thinking here, and how you think you as a leader have a role to respond, actually?

A Yeah, two things. First of all, I do disagree publicly and privately. What I was responding to mostly is he said, and like all the CEOs I talk to privately will say they agree with me on this. I'm like, well, how can you speak for every CEO? So I was really responding to is like, well, I just want to make sure that in my voice, I am clear. This is, I do not say something differently in public than I say in private. And you can ask anyone who I've talked to. That was the major thing that I was disagreeing with because Here's a high profile CEO who's saying, look, secretly everyone agrees with me. And I'm like, no, you can't say that because you just described that to me, even though we've never talked about this. In fact, I've never even met Frank. And so that's the thing that really made me feel obligated to say something in that moment. Now let's talk about why I wanted to say something. First of all, it is a straw argument that there's a choice between diversity and merit, right? If you were to say, well, look, I've got, you know, this person deserves a job, but this person is diverse. Clearly I have to pick the diverse. Like that does not How it actually works. That is not how it plays out in practice. Those are not the decisions that we make. I don't know what kind of recruiting process that would be or a promotion process, but the way it works in practice and in reality is…

AI assessment note: “it is a straw argument that there's a choice between diversity and merit”

Q When you look at Mike on the offensive today, whether we get the thesis or not, and when you look at a couple of the other players in this realm of market cap, Do you wish you were a public CEO on the offensive with a big ass budget to be aggressive and buy some of these assets? Or are you happy not being there?

A No, absolutely. I thought this was going to be a really, uh, exciting time. I thought, for public companies to navigate this. And like I said, one of the other things is, like, we were in a different boat than most any SaaS company because, A, we weren't SaaS, we were infrastructure, so we weren't selling seats, so we had no innovator's dilemma as it related to AI. Everyone who's selling seats has this massive innovator's dilemma, and we didn't. And the way I looked at it is, you know, if you look at, like, we were always trying to crack into SaaS, right? We built a, a contact center product, a marketing automation product, And it was hard to do. It was hard to crack into the SaaS market because that's just not what people thought about us. And so that was frustrating. And when I saw this, all the AI coming, I looked at it and I was like, holy shit, this is going to replace SaaS. And so all the legacy, all the incumbents here are going to have innovators dilemma. They're going to go add a feature here and there that's, oh, we're going to make your human beings doing the 10% more efficient because of the AI co-pilot thing. When reality is they're gonna want a product that is like, no, no, no, I don't need 75% of these people anymore. Give me that product. And anybody selling you seats is like, they're not gonna sell you that product. And so the amazing opportunity is to come in …

AI assessment note: “No, absolutely. I thought this was going to be a really, uh, exciting time.”

Q it is empowering. It's inspiring. When you think about leadership today, it's very different from leadership of old, of the chest pumping in the HQ, and firing up the org. It's remote world. It's a lot written. How do you think about the effective communication style to inspire, to empower, to make people feel safe? How do you think about imbuing those emotions effectively to a 5000 person team, though?

A I think a lot of the experience you have at a company is local, right? And so really the question is not like, what do I say in an all hands or whatever? Really the answer is what is the experience on a day-to-day basis people have with their team, with their managers and the other people that they are, they have the opportunity to work with on a daily basis. And that's where it really comes down to principles of how we operate. How do we get things done together? How do we set goals? How do we make decisions? How do we hold each other accountable? That's the meat of really a company culture. And people often talk about some of the fun things about culture, like in the early days, people, oh, it's a great culture. Why? Because we got to the bar and drink afterward. And it's like, that's not the culture. That's people building friendships, which is great. But the culture of a company is how you get your work done. How do you deal with a fact when you're in a room with five people and six opinions and you need to make a decision that those are the moments where the culture of a company really shines. And that's the lived experience of, of most people in a company. And so therefore how you set up The shared principles to navigate those situations. That is what really dictates the experience that people have inside of a company. And so I give a lot of thought to the principles that…

AI assessment note: “really the question is not like, what do I say in an all hands”

Q No, it was fantastic. I actually was very human in the way you brought it back down to like sports teams, and you know, the cheeseheads, I totally understand that now. My question is, how rigid are those three things, and how plastic do you as a leader have to be to change them over time with the scaling of your company?

A I mean, what I just described to you essentially is the culture of a company, and therefore you as the leader of that culture, and you know, every one of these cultures evolves, and your job is to really understand when is it that Time for them to evolve and then to lead that transformation, lead the changes that you feel the tribe needs in order to continue to survive and thrive. And as a CEO, going back to the three person company that we were when we started it up to now, we're over 5000 employees. You have to continually reinvent your job in many ways yourself in order to continue to be effective at leading organizations that are bigger and more diverse and more viewpoints and As well as, you know, in a more tactical sense, like the mechanisms you use to lead a company as it grows need to continually evolve. And I always find that generally speaking, when, you know, we continue, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we

AI assessment note: “you have to continually reinvent your job in many ways yourself”

Q No, it was fantastic. I actually was very human in the way you brought it back down to like sports teams, and you know, the cheeseheads, I totally understand that now. My question is, how rigid are those three things, and how plastic do you as a leader have to be to change them over time with the scaling of your company?

A I mean, what I just described to you essentially is the culture of a company, and therefore you as the leader of that culture, and you know, every one of these cultures evolves, and your job is to really understand when is it that Time for them to evolve and then to lead that transformation, lead the changes that you feel the tribe needs in order to continue to survive and thrive. And as a CEO, going back to the three person company that we were when we started it up to now, we're over 5000 employees. You have to continually reinvent your job in many ways yourself in order to continue to be effective at leading organizations that are bigger and more diverse and more viewpoints and As well as, you know, in a more tactical sense, like the mechanisms you use to lead a company as it grows need to continually evolve. And I always find that generally speaking, when, you know, we continue, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we're, we

AI assessment note: “every one of these cultures evolves, and your job is to really understand when”

Q the secondary that they did, which is ten billion dollars. It's expanded more and more. The greatest liquidity event of all time. How does this change surrounding areas? And it can be anything from San Francisco's real estate market to the retention of those employees to the amount of angel investors. The Valley is about to get a lot, a lot of millionaires that it didn't have before. What changes?

A I just remember feeling that way before Twitter's IPO back in, like, 20, was it, 1415? I just remember, because I actually was, like, looking for, you know, our, our first house, I think, around that time, and it was like, I just remember thinking, like, oh my god, I gotta get, if I'm gonna buy a house, I gotta do it before the Twitter IPO, because everything's gonna go nuts. And, you know, and the question is, did it? Like, yes, it did. Is it because of that? Particular batch of people that finally got some liquidity. I don't, I don't know, but, uh, I think that it's, um, I hope that San Francisco and I know some of the leaders now in the Bay Area are focused on, on a, on an abundance and growth mindset in terms of housing and in terms of building capability to absorb, uh, new wealth and also, um, not have the displace, uh, other folks. And I think that that is the mindset of folks in office now. And I think that's a good time for it. I don't know if that's your, your thought process. Or more, uh, flip side, which is it'll create more entrepreneurship, and so you probably get more founders now spinning out of OpenAI once they get liquidity because they're afforded the ability to take that risk. That's another upside.

AI assessment note: “it'll create more entrepreneurship, and so you probably get more founders now spinning out”

Q Now, I've heard so many great things, obviously, from Byron, Scott Rainey at Redpoint, and many others, but I want to start with some context. So tell me, what was the aha founding moment for you with Twilio as a good starting point?

A You know, the aha moment, right? I'm a developer. When I set out to start my next company, I knew I wanted to build something that was in a product category Category and serving a customer that I would just love to wake up every day and serve. As I thought back on my entrepreneurial career, because I had founded three companies before Twilio, all very different in terms of the industry they were in and customer we were serving. My first company was an academic content company for college students. My second company was StubHub, so marketplace for live event tickets. My third company was a brick Mix and mortar retailer for extreme sporting goods. It's like you couldn't get three businesses that were as different from each other as these three. Yet I realized that all three had two things in common. First was that each one of these businesses, again, totally different businesses in every way, except we were using the power of software to build a better customer experience and a better product than what the status quo was in each of those respective industries. And to me, as a software developer, the superpower of software is the ability to listen to your customers and hear a problem that they have, and then very quickly go build a prototype and answer to that problem and put it in front of some of those customers and say, how's this? Am I on the right track? And you get feedback,…

AI assessment note: “I realized that all three had two things in common.”

Q Now, I've heard so many great things, obviously, from Byron, Scott Rainey at Redpoint, and many others, but I want to start with some context. So tell me, what was the aha founding moment for you with Twilio as a good starting point?

A You know, the aha moment, right? I'm a developer. When I set out to start my next company, I knew I wanted to build something that was in a product category Category and serving a customer that I would just love to wake up every day and serve. As I thought back on my entrepreneurial career, because I had founded three companies before Twilio, all very different in terms of the industry they were in and customer we were serving. My first company was an academic content company for college students. My second company was StubHub, so marketplace for live event tickets. My third company was a brick Mix and mortar retailer for extreme sporting goods. It's like you couldn't get three businesses that were as different from each other as these three. Yet I realized that all three had two things in common. First was that each one of these businesses, again, totally different businesses in every way, except we were using the power of software to build a better customer experience and a better product than what the status quo was in each of those respective industries. And to me, as a software developer, the superpower of software is the ability to listen to your customers and hear a problem that they have, and then very quickly go build a prototype and answer to that problem and put it in front of some of those customers and say, how's this? Am I on the right track? And you get feedback,…

AI assessment note: “Yet I realized that all three had two things in common.”

Q In what way did you most want to break out of your jail that you were not able to do?

A Well, the thing that frustrated me, so our most successful product was our messaging product, right? And so as a messaging API, the, the crux of that product was three, was, was an API with three primary fields, right, if you will, like from to body. That's a text message. Who's it coming from? Who's it going to? And what does it say? That's a text message. And so we had millions of developers who integrated Twilio into their code and specified in their code a to, a from, and a body. Now in that world, How do you add more value to the customer over time? They specifically said, I want you to send a text message from this to this that says this. What do you do to add value? You're kind of in a box. And so if you look at the last, say, 10 years of Twilio, it was all about how do we add value? How do we create a product that allows us the expressiveness to go add value because the customer hasn't explicitly stated exactly what they want us to do, and therefore any deviation from that exact thing is called Failure by the customer. And so that's a lot of what we were always trying to do, is to create a surface area that allowed us more expression as a product team and as a company. You know, think about if you're a file storage company, you know, success is I stored your file and I didn't lose it, and failure is, oops, I lost your file, sorry. Like, and so you have to break out of t…

AI assessment note: “create a surface area that allowed us more expression as a product team”

Q When you look at Mike on the offensive today, whether we get the thesis or not, and when you look at a couple of the other players in this realm of market cap, Do you wish you were a public CEO on the offensive with a big ass budget to be aggressive and buy some of these assets? Or are you happy not being there?

A No, absolutely. I thought this was going to be a really, uh, exciting time. I thought, for public companies to navigate this. And like I said, one of the other things is, like, we were in a different boat than most any SaaS company because, A, we weren't SaaS, we were infrastructure, so we weren't selling seats, so we had no innovator's dilemma as it related to AI. Everyone who's selling seats has this massive innovator's dilemma, and we didn't. And the way I looked at it is, you know, if you look at, like, we were always trying to crack into SaaS, right? We built a, a contact center product, a marketing automation product, And it was hard to do. It was hard to crack into the SaaS market because that's just not what people thought about us. And so that was frustrating. And when I saw this, all the AI coming, I looked at it and I was like, holy shit, this is going to replace SaaS. And so all the legacy, all the incumbents here are going to have innovators dilemma. They're going to go add a feature here and there that's, oh, we're going to make your human beings doing the 10% more efficient because of the AI co-pilot thing. When reality is they're gonna want a product that is like, no, no, no, I don't need 75% of these people anymore. Give me that product. And anybody selling you seats is like, they're not gonna sell you that product. And so the amazing opportunity is to come in …

AI assessment note: “I thought this was going to be a really, uh, exciting time.”

Q What did you do to fix that? My question was going to be like, what do you think you put in place that enabled you to scale so well as a founder? What mechanism, what support structure, how did you transition so well from stage to stage? And I know it's tough with hindsight to reflectively look back, but what would you say it was?

A I think the key when I've done this well, and there's many instances when I've not done this well, when I do this well is when you're thinking to where the organization is going to be, you know, 24 months from now, 36 months from now, and planning ahead to that company, and thinking about what are the leaders that I need? What are the mechanisms that I need? What are the gaps? And building ahead of the challenges that you see coming. When you think about repeatable, there's different things at different stages you have to do, but ultimately thinking ahead and And then just recognizing, like, you know, we had talked about the culture and all that kind of stuff, and realizing that a lot of those things have to be very malleable. Certain things are not, but other things you are constantly changing. And one of the things I keep telling the company, because I actually just saw a stat that in the beginning of 2019, Twilio was 1900 employees. Here we are just over two years later and we're over 5000, right? So that's a lot of growth in a short period of time. And so the thing I keep telling the company is that every company that you have ever heard of, Admired, been a fan of, like, pick your company. Harry, what company do you think of as like, oh, this is my favorite big company?

AI assessment note: “planning ahead to that company, and thinking about what are the leaders that I need”

Q the secondary that they did, which is ten billion dollars. It's expanded more and more. The greatest liquidity event of all time. How does this change surrounding areas? And it can be anything from San Francisco's real estate market to the retention of those employees to the amount of angel investors. The Valley is about to get a lot, a lot of millionaires that it didn't have before. What changes?

A I just remember feeling that way before Twitter's IPO back in, like, 20, was it, 1415? I just remember, because I actually was, like, looking for, you know, our, our first house, I think, around that time, and it was like, I just remember thinking, like, oh my god, I gotta get, if I'm gonna buy a house, I gotta do it before the Twitter IPO, because everything's gonna go nuts. And, you know, and the question is, did it? Like, yes, it did. Is it because of that? Particular batch of people that finally got some liquidity. I don't, I don't know, but, uh, I think that it's, um, I hope that San Francisco and I know some of the leaders now in the Bay Area are focused on, on a, on an abundance and growth mindset in terms of housing and in terms of building capability to absorb, uh, new wealth and also, um, not have the displace, uh, other folks. And I think that that is the mindset of folks in office now. And I think that's a good time for it. I don't know if that's your, your thought process. Or more, uh, flip side, which is it'll create more entrepreneurship, and so you probably get more founders now spinning out of OpenAI once they get liquidity because they're afforded the ability to take that risk. That's another upside.

AI assessment note: “you probably get more founders now spinning out of OpenAI once they get liquidity”

Q Can I ask Jeff, you are brilliant at storytelling, and I actually spoke to Peter at Segment before this show. And the one question he had for you is, what does great storytelling mean to you, and how do you think you've changed in terms of how you tell stories?

A Hmm, that's an excellent question. I think, you know, where good story begins, the key thing is to start wherever your listener, your reader, whoever it is, like, start in a place they know, and then bring them somewhere new, right? So, like, you know, start with, like, you know, you're working on a new idea, and you're trying to figure out If it's any good. And like, I think a lot of people can probably connect with that idea and then like bring a blog on the journey and tell the various bits that actually end up in the conclusion. But I don't know. I don't think of myself as an expert storyteller. It's just a way of telling it like it happened.

AI assessment note: “start in a place they know, and then bring them somewhere new”

Q What did you do to fix that? My question was going to be like, what do you think you put in place that enabled you to scale so well as a founder? What mechanism, what support structure, how did you transition so well from stage to stage? And I know it's tough with hindsight to reflectively look back, but what would you say it was?

A I think the key when I've done this well, and there's many instances when I've not done this well, when I do this well is when you're thinking to where the organization is going to be, you know, 24 months from now, 36 months from now, and planning ahead to that company, and thinking about what are the leaders that I need? What are the mechanisms that I need? What are the gaps? And building ahead of the challenges that you see coming. When you think about repeatable, there's different things at different stages you have to do, but ultimately thinking ahead and And then just recognizing, like, you know, we had talked about the culture and all that kind of stuff, and realizing that a lot of those things have to be very malleable. Certain things are not, but other things you are constantly changing. And one of the things I keep telling the company, because I actually just saw a stat that in the beginning of 2019, Twilio was 1900 employees. Here we are just over two years later and we're over 5000, right? So that's a lot of growth in a short period of time. And so the thing I keep telling the company is that every company that you have ever heard of, Admired, been a fan of, like, pick your company. Harry, what company do you think of as like, oh, this is my favorite big company?

AI assessment note: “planning ahead to that company, and thinking about what are the leaders that I need”

Q Can I ask Jeff, you are brilliant at storytelling, and I actually spoke to Peter at Segment before this show. And the one question he had for you is, what does great storytelling mean to you, and how do you think you've changed in terms of how you tell stories?

A Hmm, that's an excellent question. I think, you know, where good story begins, the key thing is to start wherever your listener, your reader, whoever it is, like, start in a place they know, and then bring them somewhere new, right? So, like, you know, start with, like, you know, you're working on a new idea, and you're trying to figure out If it's any good. And like, I think a lot of people can probably connect with that idea and then like bring a blog on the journey and tell the various bits that actually end up in the conclusion. But I don't know. I don't think of myself as an expert storyteller. It's just a way of telling it like it happened.

AI assessment note: “start in a place they know, and then bring them somewhere new”

Q it is empowering. It's inspiring. When you think about leadership today, it's very different from leadership of old, of the chest pumping in the HQ, and firing up the org. It's remote world. It's a lot written. How do you think about the effective communication style to inspire, to empower, to make people feel safe? How do you think about imbuing those emotions effectively to a 5000 person team, though?

A I think a lot of the experience you have at a company is local, right? And so really the question is not like, what do I say in an all hands or whatever? Really the answer is what is the experience on a day-to-day basis people have with their team, with their managers and the other people that they are, they have the opportunity to work with on a daily basis. And that's where it really comes down to principles of how we operate. How do we get things done together? How do we set goals? How do we make decisions? How do we hold each other accountable? That's the meat of really a company culture. And people often talk about some of the fun things about culture, like in the early days, people, oh, it's a great culture. Why? Because we got to the bar and drink afterward. And it's like, that's not the culture. That's people building friendships, which is great. But the culture of a company is how you get your work done. How do you deal with a fact when you're in a room with five people and six opinions and you need to make a decision that those are the moments where the culture of a company really shines. And that's the lived experience of, of most people in a company. And so therefore how you set up The shared principles to navigate those situations. That is what really dictates the experience that people have inside of a company. And so I give a lot of thought to the principles that…

AI assessment note: “really the question is not like, what do I say in an all hands”