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SPEAKER_05: Hey, everybody. Welcome to This Week in Startups. I've got an amazing guest on the program. I should say back on the program because he first appeared on this program back in 2014.

SPEAKER_07: His name is Jeff Lawson. He's got a company called Twilio. You know it because all the developers and startups out there use Twilio for their messaging, whether it's SMS messaging or even email now since they bought the company SendGrid for $2 billion back in October of 2018. I think this is your third time on the podcast and since that time, things have gone really well. Welcome back to the program, Jeff.

SPEAKER_08: Thank you, Jason.

SPEAKER_07: It's great to be back. Yeah. You IPO'd. Congratulations. True.

SPEAKER_09: Thank you. We'll talk about that. I think the most interesting thing is you just crossed a billion dollars in revenue. Forget about a billion dollars as valuation, which is the value of the enterprise. A billion dollars in actual revenue. When did Twilio start and then when did you cross the 1 million mark in yearly revenue? Just to start to benchmark it.

SPEAKER_12: So we started the company very beginning of 2008, so 2008, myself, John, Evan, all three of us developers, and we had this idea.

SPEAKER_15: We said, you know, from my experience and all the companies that I had started prior, so I had started my first company when I was still in college, then I was the first CTO of StubHub, then I was one of the, or started a bricks and mortar retailer actually doing extreme sporting goods of all things, then I was one of the first product managers at Amazon Web Services, and when I left Amazon was thinking about what I wanted to start next, because I knew I wanted to start my next thing, and I realized that every single one of those companies, there were really two things in common, right?

SPEAKER_16: First was the fact that we were using the power of software to build a better product and a better customer experience than anything that existed to date in those industries. And even though like my startups that I had done before were very different from each other. My first company was an academic content company for college students. My second company was, you know, live event tickets, concerts, sporting events, StubHub, and then my third company was bricks and mortar for skateboarding and snowboarding and surfing. Like these businesses could not have been more different from each other yet.

SPEAKER_15: And every single one of them, we were using the power of software to build a better company and a better customer experience. And to me, that always meant, well, you listen to customers, you got and build something, you put it out there in front of the customers, you get feedback, and then you keep iterating

SPEAKER_16: your way towards a better and better and better product and a better customer experience. And the job of a software developer and a software minded company is never done. You're always listening to customers and hearing how you can create a better product.

SPEAKER_15: And so that iterative spirit of software was key to every company that I had started prior. So take StubHub, for example, we went from the first line of code written to launch in six weeks.

SPEAKER_16: Wow. Right. That's like agile. Like that to me is like, this is what it's all about. But then the other common thread among all those companies was that you needed communications in order to build a great relationship with your customer. Right. And every time we ran into these ideas, we say, oh, well, yeah, if a customer calls us, let's we can give them this information or let's reach out to customers when this happens, when their package ships, when their cars or whatever it is.

SPEAKER_20: And every time we said, oh, yeah, that's an amazing idea.

SPEAKER_15: But I'm a software developer, like making a phone ring, like having some voltage appear on a phone line somewhere in the world, like that's magic.

SPEAKER_21: I have no idea how that works. Yeah.

SPEAKER_15: And so we turned to the companies that seemed like they didn't know. We turned to carriers or like, you know, Cisco and say, how do we do this? And every time it was the same answer was like, hey, we can help you with that.

SPEAKER_16: You know, first thing, we're going to roll out a bunch of copper wire from a carrier to your data center. Then we're going to rack up a bunch of like telco hardware. Then you're going to buy a whole software stack that's on top of it. And then we need to integrate it all.

SPEAKER_15: And then we need to integrate it with your systems and build the thing you have. And so we're going to bring in this army of professional services.

SPEAKER_16: And every time I was like, wait a minute, hold on a second. First of all, millions of dollars to get started. I'm like, yeah.

SPEAKER_23: Makes no sense.

SPEAKER_16: I don't have that budget, but let's say I did. You know, what's more offensive than the money was the time.

SPEAKER_24: Yeah, it's brutal.

SPEAKER_16: This idea that like, so I have this idea and I will have to wait two, three years before customers are ever able to tell me if we're on the right track, if this experience is any good. Oh, and then they're going to tell us a bunch of feedback and tell us what we really should have built. Yeah. And it'd be another two years and $2 million before we get that built. I'm like, this is the opposite of software. And so we started Twilio beginning of 2008 with this idea of saying, how can we bring software or how can we bring communications into the era of software under the belief that the future of communications was not going to be about all those physical wires and servers and windowless buildings, but rather the future of how we as human beings

SPEAKER_15: actually make use of this technology. It's going to be about the software. Yeah. And who's going to build that? The software developers of the world. People like me who in their company saw ways to communicate with customers that would be better and just needed this in our toolkit. And so that's where we started. And so 2008, we did a fairly agile process, right? We talked to a lot of customers before we even wrote a line of code, pitched the idea.

SPEAKER_19: Then we built a prototype.

SPEAKER_07: When you talk to customers, how does that go? Like, how do you pick the customers and what do you ask them? It's an interesting thing that I think a lot of start, it's an interesting moment that

SPEAKER_33: I think a lot of startups skip. They don't talk to customers. They just build something they think customers like.

SPEAKER_16: Well, what we did in those days, actually, of all, and Twilio wasn't the only idea I was working on, actually, at the time.

SPEAKER_15: It was a few ideas I was testing out with customers and trying to figure out. Oh, really? Yeah. What were the other ones? Two of them, they've actually both been built now. One successfully, one unsuccessfully. Not by me, by other people. The first idea I was working on was essentially Dropbox, but I got one thing wrong.

SPEAKER_16: I said, the value proposition here is backup.

SPEAKER_42: Yeah.

SPEAKER_16: And I talked to a lot of customers about backup and what they wanted, and nobody gets excited about backup.

SPEAKER_43: No. It's like a chore. It's like cleaning out your garage.

SPEAKER_16: It's like the same technical solution, except the value proposition is sharing. Yeah.

David Friedberg: Something people need to do right now. As opposed to- They have a document they're attaching. Backup is like, I'll think about that after I lose my father.

SPEAKER_46: Well, and the weird thing about backup is you get no value out of it. Yeah.

SPEAKER_16: Like in the best scenario, you never get value out of the product. Yeah. It's like flood insurance. Yeah. Yeah. Exactly. And so who gets excited about insurance products? Like nobody. Sorry, insurers of the world. And so I went to customers and I got no energy in response. I was like, okay, I guess it's a bad idea. And I moved on. Interesting. Right? So defining the right problem is like half the battle, right?

SPEAKER_15: Yeah.

SPEAKER_07: And also it's sometimes you explain to customers what you plan on building and they don't understand it or don't actually even know their own behavior. Like I guess there's that famous Henry Ford quote, like if people, if I asked people what they wanted, they wouldn't have said the car, they would have said like a faster horse or something like that. What was the other idea then?

SPEAKER_11: So the other one was a BitTorrent based distributed cable system.

SPEAKER_33: Oh my God. That's brilliant. Actually, that's what Travis was building with Red Swoosh, if you remember. So you wanted to do peer to peer.

SPEAKER_11: Peer to peer. So you capture the radio waves, right? Yeah.

SPEAKER_15: From TV signals and then you could tune into anyone else's station anywhere in the world.

SPEAKER_60: Oh, okay.

SPEAKER_15: But the reason why I decided not to pursue this, which ended up being true, is that I just

SPEAKER_16: said it would be sued out of existence.

SPEAKER_61: Yes.

SPEAKER_16: And somebody did this. They did. Aero, something like that.

SPEAKER_33: Yeah, yeah. It was in New York. And what they would do is they would put a computer on a card for you in a server rack

SPEAKER_07: somewhere. Then that would be your specific antenna to you. So they were just hosting technically your antenna. Yep. Then your antenna could be programmed to then save your files. And that would be your files. And if you taped the Warriors game and I wanted to do it, I had to tape it as well.

SPEAKER_67: So they would have to manage, instead of having one file for a million people, they'd have to have a million antennas for a million people. And it still got shut down and sued out of existence.

SPEAKER_15: Well, I looked at this one. I was like, first of all, this is one of those things as an entrepreneur, you're like, well, if I really want to go give the middle finger to the establishment, this is a great way to do it. Yeah. But it's probably not going to be a great business. But the thing that really made me feel like, yeah, this is not how I want to spend my life is I talked to customers and I explained how this thing would work and all that. And I got basically a yawn. It was like, uh. And the funny thing is whenever I would pitch ideas to customers, here's how I would do it. Like I go to people who just seem like they would be the target customer to the idea, whether that idea was the cable thing, whether it was the backup thing, or whether it was Twilio. I would just pick people who seemed like they would be in the target and I would describe to them, I would say, you know, I'm working on this idea and what it would let you do is this, right? And we'll let you do is like stream a TV station from New York or whatever, you know, or whatever it is you wanted to do.

SPEAKER_16: And, and I look for the people's reaction and obviously the pitch has to be pretty, you know, decent, but let's assume I've got a decent pitch and the reaction from, from customers is like most of the time what you get is like, oh yeah, let's uh, yeah.

SPEAKER_73: Okay. How about, uh, how about the Mets?

SPEAKER_15: Yeah. You know, and it's like, it's like awkward and they're like, they try to change the conversation and like, you're like, okay, well, I guess, you know, it's, it's not

SPEAKER_16: sticking in their head. It's not piquing their interest. Okay. And you do that enough times and you, you keep end up talking about the Mets. You realize this probably isn't a great idea, but then sometimes you get a different reaction. So when I was Twilio, I'd, I'd find developers, right? And I'd say, Hey, I'm working on this idea where you have this API you could call and you could make a phone ring, for example, and then you could play back audio or, or, or playback text or record the audio or bridge people together into a phone call and do all these magical things, or, you know, send a text message.

David Sacks: And a funny thing happened when I talked to developers, you know, at first I'd explain the idea and then they'd say, oh yeah, how about the Mets? Right.

SPEAKER_16: And I'd be like, oh, okay, I guess it's a bad idea. But then a funny thing happened almost every time, like about a minute later, like conversation moved on and I'd be like, oh, okay, I guess, you know, I guess I got another dud here. Right. And about a minute later they would say, Hey, you know, I got a question for you, that phone thing you were talking about. Could I like call my customer when their package ships and let them know that the, that the package ship from my e-commerce website. And I said, yes, yes, you could.

SPEAKER_77: So it was the inception was there and it just took a little while to process the use case.

David Sacks: And every, and I would say, yeah, yes, you can. Oh, interesting.

SPEAKER_16: And what I saw was they started matching the pattern of things they had wanted to do as a developer in the past, but always assumed they couldn't. Right. So they'd just written off these ideas. That's not what I, I'm not a teleco person. I'm a software developer. So that's just out of the realm of things I do. And when I would pitch this, it took a minute, but they would start connecting it of like,

SPEAKER_15: Oh, wait a minute. What if I was that person? What if I was someone who was able to make phones ring and do all this magical stuff

SPEAKER_16: with communications? Oh yeah, I have been having these ideas my whole career that I've just put aside and said, I can't do. And then they would say, Oh wow.

SPEAKER_15: Yeah, look, can I try it out? Let me know when I can try it out. And so we started building and we had this like alpha version, like it all ran on one EC two instance at one point in like March of 2008 and all those developers I'd talked to, I sent them an email. We created an account for them on this, you know, this thing. And I said, Hey, remember that idea I pitched you about? Well, actually try it out. Yeah. I just send them some very simple API docs and an API key. And I think there was no console. They couldn't log in or all they could do is call the API and they started building. And we of course watching, are they using it? Incredible.

SPEAKER_16: Who's hitting it? And we talked to them. Yeah. What are you building? And I remember some of one of them, one of those early, early developers built something that got on Lifehacker in like June of 2008.

SPEAKER_85: And the thing was like really, you know, it was janky. Like this thing was, we took it down every night to like-

SPEAKER_86: And then all of a sudden 10,000 people engaged in. Yes. Crazy.

SPEAKER_16: But that gave us the courage to say, you know what? I think we're onto something.

SPEAKER_33: When did you hit a $1 million run rate? What year was it when you hit that? What would that be? Like 80K a month? If I remember correctly- 90K a month? Yeah.

SPEAKER_16: We launched in November of 2008. Yeah. 2009, if I remember correctly, we did about 200K of revenue for the year. Okay.

SPEAKER_20: 2010, we did about 2 million of revenue. So somewhere in there, we hit that run rate. Somewhere in that 2,000-

SPEAKER_95: And I can tell you probably approximately where it was actually. It was probably in about October or November of 2009, about a year after launch.

SPEAKER_16: Yeah. Because I was trying to raise our Series A starting earlier that year. And I remember I pitched Union Square Ventures. So I pitched- Fred Wilson. Fred and Albert and Brad. Smart cats. And, you know, they were intrigued. I remember Fred saw the- I did the demo because I would live code a thing in front of the investors. And Fred was like, God, that's really cool. You distilled all of telecom down to five APIs. That's amazing. But they still weren't sure that we understood how the go-to-market was going to work and all that. And so they said no, you know, as investors do. And I just started, unsolicited, sending to Albert every month the revenue, the chart. Every month, I just sent him- Chart bait.

SPEAKER_103: It's VC bait. Chart bait, yeah. All right.

SPEAKER_33: When we get back from this quick commercial, I want to talk about what seems to be insurmountable,

SPEAKER_105: which is 10X-ing and then 10X-ing and then 10X-ing. A million to 10, 10 to 100, and 100 to a billion. This is scaling at a level that very few people have ever achieved, certainly not in this under a decade lifespan that Twilio's had. When we get back, I want you to explain to me how you did it, how you did that 1,000X fold

SPEAKER_07: in revenue that you just passed, I think this past quarter as a public company, a billion dollars in revenue. When we get back on This Week in Startup.

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SPEAKER_67: All right. We're very lucky to have Jeff Lawson for his third appearance on this week in startups. He was on episode 308, episode 495.

SPEAKER_07: And here we are on episode number, well, it's 900 something. We don't know when we're going to actually do this. We're going to hit a thousand this fall. Talk about scaling. A thousand. And you went a thousand X. We went a thousand X ourselves from one podcast to a thousand. When you got to that million, you had to be thinking, okay, I'm onto something.

SPEAKER_114: It's growing nicely. You were growing, what, 20% month over month, something like that? Something like that, yeah. Yeah. It feels pretty good.

SPEAKER_07: Did you ever conceive of this billion dollar revenue number? When did you start to realize this was kind of a hockey stick happening?

SPEAKER_46: Well, you know, it never was exactly like a hockey stick, right?

SPEAKER_15: Because it was sort of every month for 10 years, just kind of growing the revenue, growing the customer base. So some consumer businesses, you see that point of inflection where it just goes nuts, right? Especially with network effects. But in B2B or business to developer like we are, like it is a little more you win every

SPEAKER_118: customer. But as you do that, you start to get the reputation of like, oh, this is a winning company. If you use this, it'll make you better. It'll make you stronger as a company or as a developer.

SPEAKER_16: And so you do gain momentum behind you, but it is always about, you know, you always focus on your next customer and focus on your next great product and listening to your customers and making every single one of those customers successful and evangelizing you. And that is how you build the business. And so I remember, you know, we always talk about order of magnitude accomplishments.

SPEAKER_15: So every time we cross an order of magnitude accomplishment, like 1 million, 10 million, 100 million, billion, like those are the things that we celebrate because it obviously gets harder and harder to achieve those things. Yeah. And that makes the importance of it all the more.

SPEAKER_16: And, you know, I just remember thinking like, I remember extraordinarily excited, like the first day we launched, November 20th, 2008, we launched that morning. We had, you know, the TechCrunch story landed. You know, Evan, John, and I, all three founders, we're sitting in like a coffee shop in the mission and like reading the TechCrunch story.

SPEAKER_15: We, true story, we found a bug on the website with like the story was going to land at noon, 11.58, we found a bug, we fixed it. And we're like rolling a new deploy out to production, racing the clock for the noon

SPEAKER_16: story launch. And that afternoon, we were driving down the 101, I think there was some startup event we were going to, and my co-founder's in the backseat, refreshing our intranet, saying, oh, they're paying us. They're putting in their credit cards. They trust us. Oh my God, for the first dollars that we were getting, let alone the first million or 10 million. But, you know, every time we sort of look up, what you need to do as an entrepreneur is appreciate where you've gotten to and appreciate the team and all the hard work that goes into getting to where you are today. Right. But as the CEO or the entrepreneur, you need to be looking up ahead. Yeah. And saying, this is where we need to go and always rally the troops from where you need to go. And one of the things that I always think about, like as much as we can look at how much we've accomplished and feel great about whether it's the 1 million number or the 10 million number or the 100 million number or now the billion number.

SPEAKER_15: Yeah. Pat yourself on the back.

SPEAKER_12: Say, thank you. We feel blessed. We feel proud, but we've only just started.

SPEAKER_16: And in a market as big as ours, communications, this is a trillion dollar market, Jason. Right. You cannot take that for granted. You can't say, wow, we're really big. You can't get complacent and say, oh, wow, you know, we've won because we have truly only started. So when we went public in 2016, you know, one of the things I stole from Jeff Bezos at Amazon was day one. Yeah. I love that sentiment.

David Sacks: And that is how I feel.

SPEAKER_135: Explain to people what that means and what it means to you and how you replicate that or live it.

SPEAKER_16: You know, it's like every day of building the company and every day of life, right? If you'd wake up and you say, this is day one of my opportunity. And you can say that as a person, as an individual, you can say it as a company, that whatever we've achieved to date has just gotten us to the point where we get to wake up and say, this is day one of our next big opportunity. Yeah. That's what this means. And so, you know, people often ask, oh, when's it going to be day two? And you say, well, you know, never, right? Because day one is a mindset. It's not literally a, you know, 24 hour period of the day. Right. And so it's a mindset. Do you wake up feeling like whatever we've gotten to at this point, this is just the precursor? This is just the stage, the launch pad for what we need to do in the next phase. And to me, that's what day one is always about, always waking up with that day one mindset. And so that was our, like the t-shirts we printed at the IPO said day one. Yeah. And I always drill that in. We just, you know, we just did our earnings a couple of weeks ago where we announced our

SPEAKER_15: first quarterly billion dollar run rate milestone. So order of magnitude achievement. That's incredible. And of course.

SPEAKER_105: Just let that sink in. That's like two or three million dollars a day. Let that sink in for a second.

SPEAKER_09: And if it's two or three million dollars a day, it's a hundred thousand dollars an hour. It's a hundred thousand dollars an hour.

SPEAKER_07: It's about two thousand dollars a minute. That's what you're making now. And just think about how hard it was at Twilio to get a two thousand dollar a month client.

SPEAKER_118: But at the end of the day, it is just. I mean, it's mind blowing.

SPEAKER_16: All of those, all those stats and you're faster on the revenue breakdown calculations than I am. But it's, to me, it's like you can sit and be and say, wow, all that. And you can be nostalgic or you can say like, yes, but what's the true size of this opportunity? Yeah. And what do we have to do next? Like, let's not take any of that for granted. Yeah.

SPEAKER_153: What do we need to do next to make our customers even more successful?

SPEAKER_07: What percentage of the way you are? Are you there? Like, what do you think? If you look at this and say, hey, it's day one, you think you're 1% or 10% of the way to what the market size could be in the opportunity?

David Friedberg: You said it's a trillion in communications, but there's a lot of different things. There's people's cell phone bills, whatever. What do you think? That's B2B communications. Oh, B2B communications.

SPEAKER_16: Did you know that of all IT, IT budgets are about $2.4 trillion. Okay. 40% of all IT spending is on communications.

SPEAKER_162: So the routers, the ethernet, the ISDN lines, the T1s, everything fiber lines.

SPEAKER_16: Yep. All spend. And so as I look at it, you know, some of the market like hard lines, whatever, like, you know, that's not what Tolio is going to do. But for the most part, other than the most physical elements of the network, what in

SPEAKER_118: that story should not be software? What part of that story would not be better if it was running in software, running in the cloud, at cloud scale with cloud operational excellence, and having the flexibility of software and the creative ability of the developers of the world to improve that infrastructure every day.

SPEAKER_16: And like, so to me, I look at that, that is the true opportunity. And so how big is it? I think the market is going to get reconfigured.

SPEAKER_95: And I think segments of the market that seemed clear before, like, oh, you have the connectivity and then you have the hardware that it plugs into, you have the modem and the line and the carrier. The router. And this stuff all collapses into a service offering that doesn't have those distinction anymore.

SPEAKER_168: Yeah, it's all been attracted away, right?

SPEAKER_15: Think about what happened in SaaS, right? Where it used to be, okay, well, I have to buy my data center. Yeah. Then I have to go rack up my servers and buy my switches. Yeah, get the operating system set up. Get your sysadmin in there. What's the market for Ethernet cables? Yeah.

SPEAKER_16: And then I have to install the software and buy the disks and then the backup solutions and all that stuff is now obviated by the fact that you can just pay one monthly fee to a SaaS company and get the benefit that you were looking for out of all of that infrastructure jump straight to the benefit. Yeah. And we have the opportunity to do the same thing in communications, but that's not all. Because our most recent part of our offering, we started out, we did voice and then we did

SPEAKER_15: SMS and then we added Facebook Messenger and WhatsApp and programmable chat and programmable

SPEAKER_16: video. And then we added Alexa and Google Home. And so all the channels of communication we have on our platform now, and then SendGrid

SPEAKER_15: with email, right? But then we started talking to customers and saying, how are you using this? Because when you think about it, when you're a developer platform, the fact that developers are using their time to build on top of you and their companies are spending their money either to use our platform or to pay those developers to spend their time to build those things means there's something that is yet unbuilt in the world, a problem that is unsolved

SPEAKER_16: that they're trying to solve. And as a platform, we now have 160,000 customers and over 6 million developers on our platform. We have this visibility into the big unsolved problems that are out there. When we see these patterns continually emerging, we go to our customers and we ask them, why are you building here? Why don't you just go buy a solution? What's motivating you to actually build something here? And what they reveal to us is the big unsolved problems. And we ask them, did you want to build this? Like if we had built something in this arena that solved that problem for you, that empowered

SPEAKER_15: you, the developer, but made your job easier and faster, would you have wanted us to do that? And the answer is usually yes. So for example, take the contact center space. We had all these customers building contact centers on top of Twilio. Yep. You know, ING Bank, Home Depot, a lot of these companies were building their next generation

SPEAKER_16: contact centers using our raw APIs. Right. And we go in and we talk to them and say, why are you doing that? Yeah. There's so many. You could go on-prem, you could buy all sorts of contact centers.

SPEAKER_52: You got Zendesk. You got Salesforce. Yeah, there's a lot of great cloud stuff. Everybody's doing all this stuff. Yeah.

SPEAKER_95: Why are you choosing to build your own? And the answer for these large enterprises was essentially, look, on-prem world was actually

SPEAKER_16: great for some things because we could pay all those consultants to come in and build exactly what we wanted. And when you've got- Very customized on-premises. Yeah, totally customized on-prem. And when you've got 10,000 contact center agents like we do, then you need to completely dial it in. Because if I can shave 30 seconds off of every interaction, multiply by 10,000 agents every day, huge ROI, customer satisfaction goes up, all sorts of great things happen. Okay, fantastic. So what's wrong with that world? Well, let me tell you, once you do all that customization, you have this completely bespoke thing. Yeah. No one in the world has an installation of a contact center like ours. There's one person in the corner who knows how it all works. Let's make sure that person doesn't die. Yeah, right? Like we're going to put that person in a bubble. Yeah. And then reliability starts to suffer. Like, oh, we're on the 17 versions ago because we can't touch it anymore. Yep. So security suffers. Technical debt. And customers are telling us they get 1-9 reliability. 1-9. I mean, telco is supposed to be the land of five nines, right? This is 1-9 availability out of these solutions. And so while they love the customizability, operationally, they were just stuck. Yeah. And they couldn't.

SPEAKER_15: And at some point, you're like, don't nobody. Don't touch it. Don't even breathe in the server room anymore because it seems to be working. And they're just stuck. They have no roadmaps.

SPEAKER_192: So does that mean you're moving up the software stack and you'll have more application level stuff?

SPEAKER_16: And so what we launched last year was a product called Flex. And it is a application platform for the contact center. The world's first application platform for the contact center. And what it does is it delivers a contact center. Like, you know, you sign up and you get this contact center provisioned. And it does the things you would expect a contact center to do.

SPEAKER_15: But it's not just an app that's done there. And if you want some feature, you got to, you know, earn the favor of the product manager, right? It is a platform. So the next step after you spin it up is developer download the SDK and start customizing.

SPEAKER_195: Nice.

SPEAKER_15: And the developer can go in and add modules every layer of the stack is programmable.

SPEAKER_192: So you start them on second, third base. They just got to get the ball home. Yeah.

SPEAKER_16: And then they can take it in any direction they want. So for example, Shopify moved all their customer support over to Flex last year. And they got started. They got a team of three developers and two interns.

SPEAKER_12: And in three months, they went from the very first lines of code written to powering their global support.

SPEAKER_117: Isn't it amazing?

SPEAKER_114: Both of your companies, Toby's just, Shopify has gone huge. He was on the podcast at the same time you were the first time, like in the 300s. And like, I went up to Canada to interview him. And it's like, this little tiny idea, like we're going to help mom and pop shops sell

SPEAKER_198: online. And now it's a juggernaut.

SPEAKER_12: You know what the funny thing that Toby and I have in common? What is it? We both started snowboarding companies in our past.

SPEAKER_15: Really? Yeah.

SPEAKER_200: Oh, wow.

SPEAKER_15: He did a mail order snowboard company before Shopify. And he said, why wasn't this easier? You still bored? Or you go back to skiing? I was a horrible snowboarder. Oh, okay. I did it like once a year for 10 years. Yeah. And by the end of like my one day, I'm like, oh, I think I remember how this works. And then I wouldn't get to go back out.

SPEAKER_207: Man, watch that toe side edge, man. Woo. Right on your face.

SPEAKER_16: And the first few years, because I started in like 2004, people didn't necessarily wear helmets as much back then. No. No. I did not wear helmets the first few. I would be a much smarter person.

SPEAKER_209: Twilio would have twice the market cap if I'd only worn a helmet. You probably have two concussions.

SPEAKER_109: Hey, speaking of concussions.

SPEAKER_209: Speaking of.

SPEAKER_07: For the entire existence of your company, people have said Twilio will die when Jeff Bezos points the AWS laser on you and decides to kill Twilio. And they've created competing products.

SPEAKER_105: And you have surged and beaten in your category the mighty Amazon Web Services and the mighty Jeff Bezos.

SPEAKER_33: When we get back from this quick break, I want to know how you beat Amazon in your category on This Week in Startups. What is it that makes one startup work and another startup fail? This is something I ask myself all the time as an angel investor. Well, one of the things that all the companies that win big have in common is they understand their customers. They understand their customers deeply so that they can make better products and services

SPEAKER_07: for those customers to delight them and keep them from churning. You know this. And nothing will get you closer to your customers than Gainsight PX. Gainsight PX is the only all-in-one product experience platform. And it's built specifically for SaaS products, enterprise products. So if you're an enterprise founder, listen deeply. It provides the tools so you can understand your users deeply and study their behavior at both the individual level as well as at the account level. So you know at the company level and you know the people in the company. Maybe some people are gravitating towards one feature in your product and the other group of people don't even know it exists. That's data you need to know because that will reduce churn and maybe let you land and expand inside an enterprise. Well, this information is going to allow you to improve your product and keep your existing customers happy while gaining new ones. It's fully customizable. It's so scalable. And no coding's required. You can do it yourself. Some of their best customers include Bongo, Bizaboo, Anaplan, Kenshoo. You know these great companies. And here, take a look at the Gainsight PX platform if you're watching the video. You can see us now looking at all of the active users. Hey, it's up 36% in the past seven days. And then you can go into your navigation and do really interesting things. Like maybe look at what is the path at which users are going through your product or service. Whoa, look, 17 people went to the next phase, 17% dropped off. You got to know. And you can create a new NPS survey in the editor and pop that right on the website. So here's a great call to action. You can use Gainsight PX for free right now. Okay. What more do you need to know? It's free. Get in there. Gainsight. G-A-I-N-S-I-G-H-T dot com slash twist. Okay. Let's get back to this amazing episode. Hey, everybody. Welcome back. The awesome Jeff Lawson is with us. If you want to hear his first two appearances, 308, 495 for those super fans out there. Quartz Seng grid for 2 billion. Nicely done. Company went public back in 2016. You were first out.

SPEAKER_216: Weren't you like amongst the first out?

SPEAKER_11: We were. There have been no IPOs, tech IPOs that year. In fact, I think Square had been the last one in like the fall of 2015.

SPEAKER_218: Yeah.

SPEAKER_15: And if you remember, there was a big like SaaS freak out in like February. And that's where like LinkedIn ended up getting bought. And yeah, it was sort of interesting. Like I always thought that like our reason for going public.

SPEAKER_221: Yeah.

SPEAKER_16: Was we are serving these critical, mission critical communication workloads for companies of every variety. You know, we obviously have the startups, the Uber, the Lyft. The Airbnbs of the world, but also the enterprises. And by going public, what I wanted to do is to create a bigger stage for the company to execute on. And be able to then accelerate our penetration into the bigger enterprises.

SPEAKER_05: Those big companies go, hey, this is a public company. It's legit.

SPEAKER_15: Yeah. They get x-ray vision. They can see into your books. They know that you're, they know the health of the company. They can see the balance sheet. Because trust.

SPEAKER_95: Trust is the number one thing we're selling in every business that there is. But in particular in the cloud. Right? Think about what the cloud is. I don't care if it's a SaaS application like Salesforce or infrastructure like AWS or communications like Twilio.

SPEAKER_16: So what you're telling your customers, look, take this piece of your company and trust us with it. And trust that we are going to move faster and execute better than you can do yourself if you build and do all the stuff internally. And so I believe that no matter what your product actually is, the number one thing you're selling is trust. And a great way to build trust is to be transparent. But to also have the validation of the investor community. Know that the audits and everything like that are like you are on the up and up. You're holding yourself to the highest bar. And that is a great way to build trust with your customers.

SPEAKER_232: Were you guys profitable when you were public? Or just break even?

SPEAKER_16: We were. We had always maintained a good degree of financial discipline. And while we were money losing, obviously, we raised about $240 million of venture capital before we went public. We never went into the red in a crazy amount.

SPEAKER_236: We were investing in the business, right?

SPEAKER_16: Exactly. With a market as large as ours, we've always seen this as an opportunity of a lifetime to transform one of the world's most largest and most important industries, communications. And so that is something you invest in. And so we've always invested. But we always kind of kept our eye. Like we could see profitability. It wasn't so far off. Right.

SPEAKER_118: One of the other things that was interesting is that unlike some businesses that have to invest crazy amounts in sales and marketing to achieve growth, we were always a very efficient business because of our developer first approach.

SPEAKER_16: Right. We didn't have to pour tremendous amounts of money into go-to-market to grow the top line. We've been able to grow the top line but do it very efficiently.

SPEAKER_07: It's part of that because the developer learns how to use Twilio. They leave their company. They go to the next one. They're talking to their manager or the team. And they're like, you know, Twilio does this. I did it on my last company. Or here's three ideas of what we can do with Twilio. And they just bring it with them. So now you've infected the next company because that person with the Twilio skill set went to the next one.

SPEAKER_118: There's a bit of that. But even at the company they're at today, right, when a developer finds out about Twilio, oftentimes the first thing a developer might build with Twilio, you know, they hear about Twilio.

SPEAKER_15: They sign up. And the first thing they might do is like prank call their brother-in-law. Like Rickroll someone. Right. Yeah. Like, okay, great. Like technically against their terms of service. But okay, whatever. Yeah.

SPEAKER_16: This is the first thing they might do. But then they're like, okay, I get it. I know how this works. Then they're in the work. Maybe the next day, maybe a month later, maybe a year later. And someone's like, God, you know, it would be amazing is if we could engage our customers and let them, you know, can we text them when this thing happens or let them text with us? We're going to have a conversation. Yeah. And the developer in the room is now able to say, oh, you know what? I know how to do that. It's Twilio. And they pick up Twilio and they build that prototype. And they might do it in an afternoon. And they come into the meeting the next day.

SPEAKER_15: Hey, remember that idea we were talking about? Well, check out. I built this prototype yesterday. Let me know what you think. And you've just replaced a like, you know what? In the traditional world of enterprise software, it might have been a year-long sales cycle, you know, going and getting budget, issuing an RFP, having, you know, 10 salespeople from 10 competing vendors come in and do a song and dance, pick a vendor, sign a contract, go professional services.

SPEAKER_16: You just replaced all that stuff with an afternoon of a developer saying, I wonder if this is possible and getting out of the way. And now we're done. Getting out of the way.

SPEAKER_248: Yeah.

SPEAKER_16: But then the developer is the one who brings us in. So when they build that prototype and the business starts to see, oh, wow, look at what's possible. Look at what the developer did in an afternoon. If she was able to do that in an afternoon, imagine what she could do in a week or a month or a year. Right. And so that gets the ball rolling where customers contact us and say, you know, for some customers, that's all they want. They're going to launch and that's fine. But for a lot of customers, especially in the enterprise, that will start the conversation with our sales team. But instead of having to be a hard sell, you're taking the momentum the developer created and accelerating it and ushering it through to success. You got to champion internally. And then we've got, because we're a platform that can do many things, we can then say, oh, what are the other areas of communications where you want to engage with your customers?

SPEAKER_118: What other challenges are you seeing? And we can come in and we can start addressing those.

SPEAKER_16: And so usually the first use case that a company deploys Twilio to solve is just the beginning and we get to go sell the next and the next and the next. And so we've got this dollar-based net expansion rate, which last quarter was 140%.

SPEAKER_182: Dollar-based expansion.

SPEAKER_67: So this is what the current customers, how they expand. So if they spent a dollar last year, how much did they spend this year? In aggregate. In aggregate.

SPEAKER_15: So net of churn, right? So including churn. Like most companies, historically, that would have been a negative number. Sure. Because some of your customers churn.

SPEAKER_16: For us, the customers who spent $100 a year ago, today in aggregate are spending $140.

SPEAKER_192: So even if you lost a couple of people, you have that net negative churn, I guess is the industry churn.

SPEAKER_254: Yep. And they made up for it, right? All right. Back to the Amazon question.

SPEAKER_07: Over and over again, you heard, I heard, pundits, yada yada, Twilio's toast.

SPEAKER_114: Amazon can make this in an afternoon and just destroy them. Well, Amazon did make competing products and you guys have just continued to grow.

SPEAKER_09: Why? What happened? Why didn't they kill you?

SPEAKER_15: Well, first of all, we have a great relationship with Amazon, right? So we partnered with them and we help power a lot of those products. And they were an investor in Twilio in our last private round. Oh, really?

SPEAKER_257: I didn't know that.

SPEAKER_77: Bezos or Amazon itself? Amazon. Does that come with like, we're not going to compete with you or it just comes with a little bit of like friendship?

SPEAKER_260: It comes with a, you know, it's a relationship. Got it.

SPEAKER_16: And, you know, having worked at AWS in the early days and, you know, knowing Andy and the team, you know, I feel like we've always had a great relationship. But that aside, business is business, right? Got to compete. And so the way I think about it is that here's the classic blunder that I think some companies make when they fear or when Amazon does enter their domain. And by the way, if you have an interesting enough business and a large enough market, you should expect that even if it's not Amazon, somebody big and scary is going to enter your domain. Of course. And here's the classic mistake. Think about Amazon's playbook. What does Amazon do? They always focus on the customer. And, you know, famously, the culture at Amazon is about focusing on the customer and their needs, right? And so what happens to a lot of companies when Amazon enters your space? What is that startup focus on?

SPEAKER_264: Amazon.

SPEAKER_16: Amazon. Yeah. And you have board meetings. What's our Amazon strategy? How's our, what's the strategy to defeat Amazon? And all anyone talks about is Amazon. Meanwhile, Amazon's sitting there talking about your customers. Yeah. Who's going to win? Exactly. Right? And so my advice to anyone, if like, you know, you worry about Amazon or Amazon has entered your space, like, and this goes not just Amazon, but any company. Well, the answer is right in front of you. You're your customers. Yeah. Just focus on your customers, serving your customers better and faster with the things that they need from you. And if you do that better than any other company. You're fine. You should win. Yeah. And here's the thing to remember. Any company, whether it's Amazon or Google or Facebook, or just pick the scary company in your domain, whatever it might be. It's just made of people. We're all people. I'm a person. Jason, you're a person. Every listener, you're a person. And we're all building companies. And every one of our companies is prone to success when we have great people or is prone to failure if we have bad people or we make bad decisions.

SPEAKER_15: And just remember that even though there's, like, a big scary corporate logo that you might read a lot of stories about this company, behind that logo is people.

SPEAKER_16: And you are competing against the people behind that corporate logo for who's going to better serve the customer and who's going to listen to customers and who's going to build faster and who's going to serve them better and make customers more successful.

SPEAKER_15: And it's, there may be a scary, like, trillion dollar corporate logo behind that thing.

SPEAKER_16: But at the end of the day, it's, ask yourself, do I think that they, whoever the team is inside that big company that is, like, competing for my customers, do I think they're better than I am? And if the answer is yes, well, maybe you should go join them or go find another business. But probably when you look inside yourself, you're like, no, I'm better, you know, I'm better, my team is better, our ideas are better, we're here to do this, we're here to serve our customers, and we are smart, and we are motivated, and we're going to get this done. That's essentially, that's the reality of life.

SPEAKER_07: Yeah, it's interesting. People get really scared by these big names. You have to remember, it's like, your business is one of 500 things they're contending with, right? Like, Amazon's got a lot on their plate.

SPEAKER_85: Yeah, you teed up the question, like, Jeff Bezos is going to, like, say, Trilio, you know, wake up one day.

SPEAKER_192: Jeff Bezos is, like, shopping for new baiting suits, because he's only got one, apparently.

SPEAKER_283: Did you see that story? You know what, I really don't. Jeff Bezos has one baiting suit. It's become, like, national news.

SPEAKER_284: I don't keep up on his undergarment situation.

SPEAKER_15: Did you work with him when you were there? I had some interactions with him. What is he like?

SPEAKER_288: What makes him so special?

SPEAKER_15: I would just, you know, I had some interactions. I would say he's focused. He tends to be right a lot, which actually became one of the values of Amazon, which I think is so funny, because it's, like, how do you make a value being right? It's either you are or you are, but you can't say, oh, yeah, I was going to be wrong, but I remembered our value. Is to be right. So I'm going to be right now. But he does. He has this knack for being right, which is great. And then he helps train the people around him.

SPEAKER_16: And what I think about more than Jeff is the system, the values of Amazon, when you look at the leadership principles that they have. It's really a playbook for how to think and act like Jeff does. Yeah. So if you want a window into Jeff, just read those principles.

SPEAKER_15: That really is Jeff saying, here's to the best I can figure out. Here is what I do that tends to help me make good decisions and build a great business. And here's his playbook. And I'm handing it to all of you, all the people at Amazon. And by the way, it's not private. It's public on the website. He's handing it to the world. Yeah.

SPEAKER_118: Saying this is what it means to focus on customers and to be focused and to make hard decisions and to live with them and read his shareholder letters. Yeah, they're great.

SPEAKER_94: You know, there's amazing tidbits.

SPEAKER_297: That's why I thought it was like so weird. Did you read that story about like the New York Times? They're like, it's so horrible to work at Amazon. And they have like all these people who quit and hated it.

SPEAKER_300: And it's like, do you realize that people who work at Amazon are some of like the most loyal, like insane, like high performance people?

SPEAKER_07: Like, of course, it's not for everybody, that culture.

SPEAKER_33: Accountability is critically important for your startup. You have to assign tasks. You have to assign projects. You've got all different phases of things you're trying to deploy at your startup. And Monday.com is going to allow you to do this. It's beyond just task management. You create boards. You can do your own or you can do it from a template. And it's really popular with non-tech teams as well as tech ones. And it replaces all these burdensome Excel files where you're putting checklists and punchlists in Excel. And then or maybe in a Google sheet and you're trying to make that work. No, you want to use Monday.com. And Ben Seidel, who's been on the program and is in our portfolio from Neighborly, he uses it to plan the build outs of the new venues that he's creating at Neighborly. They can assign accountability. And if people don't get something done, you know who's responsible. So you can go have that little chit chat and do a walk and talk. Pete Davis from AmpJar, another one of our high-growth startups, he went through our incubator. He's from Sydney. He uses it for the growth marketing project management he's doing. You do growth marketing. You know how much work that is. Well, here's how easy it is. Here's my CMO, Presh, creating a board. And he's doing this for open office hours, which you guys have been experiencing when I do open office hours. And he's assigning tasks. He's setting up a type form integration. They have all those great integrations. So you can see all the status of the founders and their biggest challenges coming into that monday.com board. He's going to make the board public. And we're going to do this ourselves here. We're going to have a public board where you can see the topics that are going to be discussed. Go see it right now. Officehours.launch.co slash August. I want you to start a 14-day free trial by going to monday.com, the day of the week, monday.com, what a great domain name, slash twist. That's monday.com slash twist.

SPEAKER_07: And use the promo code twist when you're ready to buy, and you'll get 10% off a paid account. Thank you for that, Monday. Great product, great software. I met the team the other day. Wow, really impressive progress. And everybody, go ahead and try it. Okay, let's get back to this amazing episode. How has the culture changed in your company? How many people do you have now?

SPEAKER_303: We're almost 3,000 people.

SPEAKER_07: 3,000. You had three people 10 years ago. How did your job change having to get 3,000 people to work towards a common goal besides, you know, 330, 300? I mean, we could all imagine how to manage 3 in 30 people. 300, there's some techniques. 3,000 is a whole different ball of wax, isn't it?

SPEAKER_11: What I find is that as a startup CEO going through hypergrowth, you just have to accept the fact that your job is to serve the needs of the company.

SPEAKER_118: And those needs are going to change as the company grows.

SPEAKER_16: And they're going to change quickly. And so for me, I would say every 9 to 12 months over the last 11 years, I've had to say, hmm, what's my job now? Because it seems to have changed.

SPEAKER_15: Because the things I was doing a year ago to lead this company don't feel like they're working anymore. And so you start to see these things and it's natural to get really frustrated.

SPEAKER_16: And to say, you know, people aren't listening or, God, I've said this before. How come I have to say it again? Or, you know, whatever it is. But, you know, you can get angry. You can get angry at, you know, the fact that your company is growing. You can get angry at gravity for being there, right? Or you can say like, well, that's just a fact. And therefore, I have to evolve and continually change the way I lead in order to serve the needs of a much larger company.

SPEAKER_13: What's the number one thing you've had to change personally as the leader of 330, 300, and now 3,000? How if it's changed?

SPEAKER_312: It's just certain things get more important, right?

SPEAKER_118: First of all, you always have to hold yourself to the highest leadership standard. Because I find that companies become a reflection of the leaders. 100%. And in particular, if you're a founder, CEO, you're the most obvious and apparent leader in the company, that the company reflects your actions, your behaviors, your thought processes, like it or not. Like the company becomes an amplification of both your best features and your worst features.

SPEAKER_15: Your bugs and your features. Right? And so be prepared for that and then say, okay, great. How do I focus on presenting my best features and making them better? And how do I prevent the things that I don't like?

SPEAKER_317: Yeah, fixing your bugs. Fix your bugs, right?

SPEAKER_118: And I feel incredibly privileged to have worked with a coach as I built Twilio, a guy named Jerry Colonna. And what's nice-

SPEAKER_319: Oh, Jerry's your coach?

SPEAKER_07: Jerry was just on the podcast. Jerry hired me to be an analyst for him for $1,000 a month with Acme Ventures, which was the precursor to Union Square Ventures, which was a precursor to Flatiron. And he was just on the podcast for the new book, Reboot, which is incredible.

SPEAKER_46: Well, that's what I was going to say, which is everybody can now, for the cost of about $12 or whatever- Read the book.

SPEAKER_118: Read the book. And Jerry is fantastic in the sense that it is easy. Two books I'll give that I really loved on this management concept. I mean, there's so many books. But Jerry's book just came out, Reboot. Reboot, amazing. And then the other one is Danny Meyer's book, Setting the Table.

SPEAKER_07: Really? I haven't read it. Union Square Cafe, Shake Shack, famous New York chef, right? I think I got this right.

SPEAKER_326: Yep, famous New York chef, Shake Shack, Union Square Cafe.

SPEAKER_07: He's the guy who included the service fee and got the back of the house to share in the service fee. Very iconoclastic, strong beliefs. What did you learn from that book?

SPEAKER_16: But a beautiful human being. He is just one of the most thoughtful, menschy people that I've had the privilege of getting to know in the course of building Twilio. And the book is fascinating, right? He talks about this notion of, you know, when you start your restaurant, you want everything to be perfect. Yep. And so you put the salt shaker in the middle of the table, right? In the perfect middle of the table because that's where it's supposed to be. And you train your staff, you know, all the service people. Like, you want to put it right in the middle of the table. And then what happens is like, you know, someone's setting the table and it moves off center of the table. And there's a natural tendency, especially for an entrepreneur, to get mad. Why is it off? I told you to put it in the middle. And he's like, but the thing to do is to just show people, just put it back in the middle of the table. And with your leadership example, show how it's supposed to be. And every time it moves off center, what do you do? You move it back. Show, don't tell. And here's the reason. The reason is you can get angry at that thing and say, well, it's not supposed to be that way. But you have to recognize that the order of the universe is to move that salt shaker off the middle of the table.

SPEAKER_118: That's what the universe does. It creates disorder.

SPEAKER_16: It creates chaos. The universe is there to do that. And you can get angry at the universe. Yeah.

SPEAKER_15: Or you can accept that and keep correcting it and bend, you know, essentially bend the behaviors towards what you want. Right. But getting angry at the universe, getting angry at essentially the natural order of things. Like I liken it to, am I going to get angry at gravity or am I going to accept that it exists? It exists. And then work around it.

SPEAKER_16: That to me is essentially the essence of leadership in a complex and demanding environment. It's like you need to take all these things that are going to happen to your business, right? And figure out how do I lead with grace and humility and empower the people around me to themselves deal with the salt shaker getting moved for whatever their salt shaker is. And they're part of the job and try to teach people here's what we're here to do and do that all in the purpose of a mission your company is on. And so what your job as the CEO at the end of the day is to set that vision and that mission and continually re-articulate it. I am always surprised at how often you need to repeat yourself. And that's the job. That's what you're there to do. And then the second thing, assuming you want to achieve it, you need to keep on repeating it. And the second thing you need to do is to show people by your actions and by the values of your company how to go achieve that. And what is the path we're going to take to get there? How are we going to get there and get there intact and get there as a greater group of human beings than we started with? And what is the way that we're going to do that? Because along the way, you're going to achieve obstacles. You're going to have to jig and jag and find ways around obstacles. And it's going to be hard and people are going to be upset and angry and like all sorts of emotions come out in this whole thing. And so how do you as a company address those? How do you as leaders address those things? And how do you react to those situations? That to me is what makes or breaks the company and its values and the probability of you actually achieving the mission that you're on. And I've sort of internalized with Jerry's help and others that I think that is the most important thing.

SPEAKER_118: And sure, there's stuff we do in the day-to-day. Tactical.

SPEAKER_16: I got to check my email. Sure. I got to make sure in the early days, okay, the bills have to get paid and the customers. But as long as I – the most important thing over the longer timeframe that you do is set that compelling vision and mission the company is on and get people to want to follow you on that mission.

SPEAKER_344: Yeah.

SPEAKER_16: And number two, set the tone for how is it we're going to go achieve that mission.

SPEAKER_344: Right.

SPEAKER_95: And that's with your own behavior, your own leadership, the actions you put out. What is your tone? What is your tone?

SPEAKER_49: Your nature is different. Are you intense? Are you focused? Are you kind?

SPEAKER_310: What is your tone?

SPEAKER_16: What I generally try to do is bring energy towards all of those interactions because, like, look, building a business is hard. Yeah. And it's easy to get down. It's easy to get frustrated. It's easy to get tired. And if your leaders look tired. Oh, it's bad. Right?

SPEAKER_349: Yeah. They're exhausted. I'm not going to pick up the rifle if they're not picking up the rifle. Right? You got to come in with the rifle up. Yeah.

SPEAKER_16: So number one thing that I think about is I just need to approach these situations with the excitement that I have for this opportunity. And the energy for whatever the situation we're in is. Yeah.

SPEAKER_118: And a fundamental belief in the human capacity to overcome whatever the adversity is or whatever the situation is, whatever hill we need to take, whatever thing we're trying to get done.

SPEAKER_16: I fundamentally believe in the human ability to do that. Yeah. And if I come in with that energy, then, and that's what I present to my team, then that will give them the energy in order to do the same. And that is how I believe. Now, look, sometimes it's hard. Sometimes you actually are tired. Sometimes it's hard sometimes. Yeah. Right? And so the other thing I would say is I take very visible vacations.

SPEAKER_359: Oh, really?

SPEAKER_16: Oh, yeah. So first of all-

SPEAKER_359: You make it clear to people, I'm taking two weeks off. Take care of yourself.

SPEAKER_118: Yeah. Take vacations. Any business worth building is not a sprint. It's the marathon, whatever. Pick your analogy.

SPEAKER_57: Might be some sprints in there, but it's a marathon. Sure. Yeah.

SPEAKER_15: We just had our big customer conference. That feels like a sprint. Oh, man.

SPEAKER_360: That thing got huge. This is a marathon.

SPEAKER_15: Yeah.

SPEAKER_12: Our first year in Moscone Center. That was really exciting.

SPEAKER_361: Oh, my God. That's an arm and a leg. You must have a big budget now.

SPEAKER_114: How many people came to that? What do you call it? Twilio? Signal. Signal, right.

SPEAKER_12: Signal's the name of our conference. We had over 4,000 attendees. 4,000. Wow. Yeah, much bigger than last year, despite the fact that we did it in August, which was-

SPEAKER_349: Well, that's probably the only dates available for Moscone.

SPEAKER_297: I went and negotiated with them. They're like, 8,000 hotel rooms, this, that, the other thing. It was so hard to negotiate.

SPEAKER_284: It's tough to get in there. And when you're first year in, they're like, you're on the lowest run here. No, I know.

SPEAKER_368: They're like, Steve Jobs has been here before. They tell me the Steve Jobs stories. Yeah, Steve gets whatever date he wants, but you-

David Friedberg: They built bathrooms for Steve Jobs. Really?

SPEAKER_07: When he went and he would do the things there, he'd be like, I want these bathrooms, and that my people are going to come in and build these bathrooms for me. And they're like, bring in bathrooms, whatever. It was like crazy stories like that. All right, listen, you got to wrap up. You got a lot of-

SPEAKER_371: I didn't do that.

SPEAKER_07: You didn't do that. You're not that crazy. Let me ask you a personal question.

SPEAKER_198: When we met, you were doing okay. You're a billionaire now.

SPEAKER_16: How do you not let that- Before we talk about that uncomfortable topic, I want to finish- It is uncomfortable. That's what I want to ask you about.

SPEAKER_15: That's why you're going to ask. That's why you've got a following that you do, because you ask the hard questions. Take vacations. Take them.

SPEAKER_16: You want to finish that thought, but also let your teams know that you do. Right. When I come back from vacation, I announce, we have all hands every month. I come back. I say, I just took an amazing two-week vacation. I unplugged. First of all, thank you to my amazing team, everybody here that lets me do it, and by the way, all of you, take care of yourself. Remember to take your vacations.

SPEAKER_381: And you show them.

SPEAKER_15: You don't just tell them to take the vacations. You show them you take the vacations. And I show them, and I show appreciation for the team, and I think that is one of the key

SPEAKER_12: things to actually being able to have longevity. The other thing is, and I didn't do this until about a couple of years ago, physical health. You lost a little weight. Look at you. You're looking good. Thank you very much, Jason. What are you lifting?

SPEAKER_109: You're biking? What are you doing?

SPEAKER_384: I ride outside. I like to run now. How many pounds did you lose? About 50 pounds. You look great.

SPEAKER_109: I used to say, I love- When you walked in, I was like, whoa, it's noticeable in your face.

SPEAKER_16: Thank you, Jason. Your energy level goes up, right? Energy level goes up. But I wasn't taking good care of myself. Take good care of yourself. And the amount of energy you'll have, the amount of excitement. Yeah, get some sleep. Work out, drink those juices. All those things, especially in the early days of a startup, be like, who has time for working out or sleeping or drinking juices? You're like, work, work, work, work, work, work. And look, I won't lie to you. In the early days of a startup, lots of hard work. And you can sit here and say, sure, Jeff, easy for you to say. Now. Yeah, now. You're 10.

SPEAKER_15: Yeah. And you weren't doing that when you were a smaller company. But I'll say, I know plenty of entrepreneurs who have made taking care of themselves a critical

SPEAKER_16: part, like physically, getting to the gym. Mental health. I didn't do it. Mental health. In the early days of a startup, and they are incredibly successful. Yeah. So no matter what you think is more important than being physically healthy and mentally

SPEAKER_19: healthy, guess what? I doubt it is.

SPEAKER_05: Yeah.

SPEAKER_07: All right. How has this messed with your brain at all? How do you contend when you talk to Jerry? It is a burden, great wealth. Do you think about it sometimes? We get on this train, and all of a sudden, something hits. Like it hit for me with Uber, right? And all of a sudden, you have this big check comes in and change your life a little bit. How have you dealt with it? Because you're doing it on a really big scale now. Are you distracted by the money? Being a billionaire, it makes you obviously uncomfortable for me to even say it to you. I can see the look on your face when I say, Jeff, you're a billionaire now. You got the B next to your name.

SPEAKER_395: How do you-

SPEAKER_392: Now you're just going to keep going. All right. No. I got to rise.

SPEAKER_33: How do you manage it? Like, you know, because a lot of people- It's turning that screw a little bit. I have a lot of friends who don't manage it well or had like a lot of- Listen, I have friends who flip the car. Let's put it that way. You know, they kind of really made them weird. They had to go to therapy and figure it out. You seem like you've adjusted really well to this, you know, level of privilege, wealth.

SPEAKER_114: And let's face it, it's a responsibility in our society to be in this position. How have you dealt with it?

SPEAKER_16: I would say- You don't think about it? First thing first is remember that like for a company founder who has a lot of equity, right, it's paper wealth. Okay. So keep that in mind. Yeah. Right? Keep things in perspective. Like nothing is guaranteed. Yep. And I was like, every time Twilio would reach milestones where like, you know, we would like raise around a financing and so our paper value got higher, whatever it is, I would always remind myself and the company like, hey, look, we're just, we're just getting started, nothing is guaranteed.

SPEAKER_118: This could all go sour tomorrow. So remember that and focus on what we need to do as far as our customers, their

SPEAKER_16: success and the company's success. And if we keep doing that, you know, maybe some of that paper wealth turns into actual wealth one day, but like, don't take that for granted. So that's the first thing that I would say. And even for me, like most of, um, most of what I have is in Twilio stock. Yeah. Which is, uh, it's fantastic that the market has treated us so well, but at the same time, I can't take it for granted and say, you know, peace out. Right. I got to build a company here. Yeah. Um, but the second thing and the more important thing I would say is no matter what your level of, uh, fortune is in the world is having a responsibility to the world around us and the greater society around us and the communities that we operate in. And just remember, like we've had the privilege of building these companies because of the amazing society that we have.

SPEAKER_406: Yes.

SPEAKER_16: Democracy, democracy, capitalism, capitalism, but even just, but also recognize that you can't take those things for granted. And by the way, not many people around us don't have those things. Yeah. Um, and so, you know, uh, investing in the community around you, whether it is the people

SPEAKER_118: like homelessness is a big issue in San Francisco, whether it's investing in the democracy and making sure representative democracy continues to work or, uh, investing in other areas.

SPEAKER_16: I believe that it's our job as our companies and as ourselves to recognize the privilege

SPEAKER_118: that we have entering this life of entrepreneurship and building a company and giving back and making sure the world is better for more people around us. And for the next generation of entrepreneurs, how do we leave the world better than we found

SPEAKER_16: it? And so, you know, the only thing that I would say is, is a material difference, um, after having been marked as a billionaire is that, uh, my wife and I were able to take the giving pledge. And so we committed to giving half of our wealth, uh, that's technically the commitment, although our intention is to do more than that. Of course. Um, whatever our wealth ends up being in our lifetime, we commit to giving almost all of

SPEAKER_12: it away, uh, in the interest of using our good fortunes on this planet to help bring more good fortune, more opportunity to the people of the world around us.

SPEAKER_411: All right.

SPEAKER_07: Listen, Jeff, you said it all, uh, and you said it well, congratulations on the tremendous success. It's been great getting to know you over the years and thanks for coming on the pod so consistently, a lot of, sometimes people get the, uh, you know, they get the escape velocity. I don't hear from them again, but you come back on the pod and you share it and you're so candid. Uh, if you are a developer or, uh, looking for a great job, no better place to work, no better boss to have than Jeff Lawson, go to their jobs page and, uh, go join the team

SPEAKER_88: there. It's still day one at Twilio. All right.

SPEAKER_415: We'll see you all next time in the speaking service. Bye-bye.