The Changelog: Software Development, Open Source - Getting to Resend (Interview)

Episode Date: April 4, 2024

This week Adam is joined by Zeno Rocha — the creator of the beloved Dracula theme and Co-founder and CEO of Resend. They discuss his personal journey and the challenges of balancing work and family life, how becoming a parent has given him new perspectives and influenced his decision to start his own company, the role of citizenship and immigration in his journey, how he prepared for the Y Combinator interview, meeting Paul Graham, the challenges of sending email, and the future of Resend and the possibility of a Series A round.

What's up friends? Welcome back. This is the Change Log. I'm Adam Stachowiak, Editor-in-Chief here at changelog.com and I'm going solo today talking to my good friend Zeno Rocha. Zeno is the creator of the beloved Dracula theme. It's my favorite. And is now co-founder and CEO of Resend. We discuss his personal journey and the challenges of balancing work and life and family, how becoming a parent has given him new perspectives and influenced his decision to start his own company, the role of citizenship and immigration in his journey, how he prepared for the Y Combinator interview process, meeting Paul Graham, the challenges of sending email,

and the future of Resend, and the possibility of a Series A round in the near future. And a bonus from me on this show, I was surprised to learn that Zeno is a fan of Silicon Valley, the TV show. So of course, we talked about that too. A massive thank you to our friends and our partners at fly.io, the home of changelog.com. That's where we live. That's our home. As Happy Gilmore said, go to your home. Go to your home. With Fly, you can easily put your app and your database and your AI near your users.

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teams is an issue for us because um like the one the one alert fires for one team and then it seems like to have to bounce around and it never does uh which then means that we have tons of communication issues because like people aren't updated. No, I mean, to be open and honest, when can we switch? So you're probably tired of alerting tools that feel more like a headache than a solution, right? Well, Signals from Fire Hydrant is the alerting and on-call tool designed for humans, not systems. Signals puts teams at the center, giving you the ultimate control over rules, policies, and schedules. No need to configure your services or do wonky workarounds.

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Again, firehydrant.com slash signals. Well, we're back. It's been too long, in my opinion. I invited you early this year. Got super busy. Didn't get a chance to get you on until basically three-ish months into the year. I've wanted to get back in touch with you for a while. I've been a fan of you for many years. I would call you a friend like if we lived close

I would hang out with you that kind of thing yeah for sure I am sad though that I think I might be saying your name wrong if it starts with Z I'll answer right yeah it's Z now okay well I was talking to Michael Greenwich not long ago and we were talking about you because

he was on Founders Talk we were talking about obviously WorkOS. And you worked there prior to founding Resend recently. But as I'm talking to him, I'm like, I kept calling you Zeno. And he kept calling you Zeno, I believe. Which is it? Which do you prefer? So if you want to do the right Portuguese spelling, it would be Zeno.

And that's why he calls me zeno but even i say zeno i think it's just easier on the phone or when i go to starbucks i'm like i'm zeno i'm zeno i i got used to it now but yeah zeno works too either one works okay all right so either or zeno or zeno and you're cool with that i'm totally cool with that. Now I feel better again because I was like, I feel like, you know, considering the intro, feeling like we're friends. And here I got a friend's name wrong. I feel like a jerk. You got to fix that. We're out the gate, you know?

Yep. Yep. But, you know, I've loved your story. We've covered a lot of your journey I would say as a developer not obviously every nook and cranny but we've covered you know from an injury to accidental open source to you know leading in a lot of ways in open source and you know building in public and being very out there with your ideas obviously just mentioned Michael Greenwich and WorkOS and we've been sponsored by them before I'm a fan of Michael I'm a die hard forever pry it from my hands if you can Dracula user

I like the way you say it better than you say Dracula which I think I love your accent the way you say it because I just say Dracula right but I love the way you say Dracula

which is so cool and then now founder congratulations yeah holy smokes what a journey what a journey man right a journey, man.

Right? There's definitely a lot like that inspired me during my time at WorkOS, you know, to start this off, like just seeing how a small team can operate and seeing the beauty of SaaS internally, the beauty of a product that is very sticky and how it can grow with their customers too. So, yeah, I decided to give it a shot. And funny enough, it was like close to the time that I got my citizenship. So I was like, oh, now I can live the American dream fully. Now there's no strings attached. Let me just go all in. And that's what came out of it.

Before we go into, you know know this new journey for you can we touch on some personal stuff too do you mind for sure let's do it follow you i think i may have seen on instagram potentially i don't know where i saw but i think i think i follow you on instagram and i'm barely on there i'm just like a lurker you know i'm not a poster you know i saw you got married so you had a child you know I saw some like key moments in your life that really matter. Can you share some of like, since the last time we talked, like change in your life, you mentioned citizenship and obviously founder, but can you share some of your, you know, journey in life, I suppose?

Man, having a daughter was just something that really changed my perspective. It's not like I changed as a professional as much, like I continue to be a workaholic and things that I, maybe I'm not that proud of, but definitely as a human, just changed the way I see life. And a lot of the decisions I made professionally were because of that too. So obviously me and my wife, we've been here in the U.S. now for nine years. I recently moved from L.A. to San Francisco. That was another big change. And all of those things together, you know, the fact that we are here alone as a couple, we don't have family around.

And now growing up, growing this human being and it's just like super wild. So, yeah, my wife and I, we've lost our parents, so we don't have parents with us. So we don't have family nearby. So similar where we're not like it wasn't a move that isolated us as parents, but it was circumstance. Right. We have friends who go on date nights frequently and because they have like parents nearby right and so it's hard not to be like jealous of that because like you know it really takes a lot it takes us to move a small mountain basically sometimes maybe in a big mountain to get that that together time where we don't have our two amazing kids around us but

similar like my i think we're blessed with kids because kids provide perspective, really. I see my face in my youngest, my four-year-old, more than I see my face personally in my eight-year-old. And I have a 20-year-old daughter, too. So I have three kids. Two of them are still children, one that's now an adult. But, you know, all three of them have provided unique perspective and unique feedback into how I operate life. You know, how I think about life, how I show up for life, not just to succeed or to, you know, do awesome podcasts like this with people like you who I care deeply about. But I guess just to like, what is my purpose? What am I optimizing for? What am I showing up for? And, you know, pushing things away that don't really give me the things that are what I'm optimizing for and like fine tune, you know, to the things that truly matter. I think that's what kids have done for me.

It sounds like that's what your daughter's doing for you. For sure. I'm wondering, like, do you think you would still be doing the podcast if it wasn't for them? Like, because that's something I really admire about you. Like, you've been able to keep this up at the highest level for so many years. And very few people in the world can do that. Do you think that resilience comes from having kids and all that? Yes, I would say resilience, patience, pain, deep joy, deep love. I mean, like all the possible emotions come from children. Yes, and maybe even the grayness in my beard.

Some of the gray hairs that are coming in my head i'm 45 years old now i don't know if you know that i just turned 45 so yeah i don't know i think it's hard to tell it really is hard to tell i know that not that this show's about me uh but you did ask uh it was only until recently that my my kids got to see me at a conference so we had a conference i live in austin texas now and there was a conference here called that conference so we partnered with our friends at cloudflare to get us to go there and all that good stuff we had a bunch of fun we set up our banner we do a mobile podcast setup it's amazing like it looks cool we got two tvs there with all of our YouTube clips. Like it looks, it looks super cool. Right. And my kids, they see me go to work and they see, they hear really. Cause one of my, one of my children is really into music. And so

he loves break master cylinder, our producer of our music, right? All of our music is custom and a custom license for us too. And so they get to experience the podcast and they get to see it from the fringes. They know what I do and they hear the music and they hear the content because I'm listening sometimes. I call it, hey, I'm QAing this podcast. I got to listen to my own stuff to pay attention,

to fine tuning and get better. But they didn't get to see the thing in real life. They see me go to work, they see me talking to a microphone, they see the lights and the cameras and stuff like that. But to see me at a conference and people, you know, like coming up and meeting me and Jared and giving us hugs and high fives and like the whole realness kind of come full circle in that moment. So like only recently did they really get to see like what dad does and it you know we essentially create a digital artifact called an mp3 and we deliver it across the internet and then

people listen to that like that's ephemeral really there's no physicality to that aside from maybe a t-shirt or a sticker or the banner you know they don't see it it's like now they get why you're locked in in a room for like an hour or two and like, okay, what this really is, right? Like, it's fascinating. It's funny because I feel like a lot of my work ethic comes from growing up and watching my dad and my mom work, you know, like we, we grew up, uh, in Brazil without, you know, a lot of money. And we, my, my parents used to sell, uh, superhero costumes. So imagine like as a kid, I absolutely loved it. And basically the way it worked was I would see them like just producing everything like the whole week. And then on Sunday, we would go to like a street fair and then sell those things. And sometimes it would rain and then that would screw up the whole week.

And, you know, we wouldn't have money during that week and things were very tight. Other times, like it was sunny and then we would sell a lot, a lot of kids because like a new Spider-Man movie came out and and so on and for me it was clear like i could see them working with their hands and then on the next like during the week and then over the weekend talking to people and selling and i feel like for us it's so hard right like we're just locked in a room like i i hope I can somehow show to my daughter, hey, here's how this whole thing materializes, which is so hard when you're working in a digital format. It's so tough. For sure.

I would say some advice on that front then. I don't know. Do you work from home? Do you have a studio? What's your scenario? Are you at home for the most part? Yeah, I work from home. So you may have heard me say this on a podcast, potentially if you listen frequently enough, I don't say it too

often, but I've definitely said it enough where I think our listenership knows about it, but I call it my micro moments essentially. And so when you work from home versus a dad who has to go to the office, in quotes, the office, right? Somewhere that's different. You will go potentially drop them off at school if they're old enough, maybe like 7.30 in the morning, right? Go do your day, stop at a coffee shop, go to your office, go to lunch, be with coworkers, leave, be in traffic, get home, five, six, seven o'clock at night, whatever. Some version of that is true for most people who leave and go to work. But for people like you and I who get to work from home, five, six, seven o'clock at night, whatever. Some version of that is true for most people who leave and go to work. But for people like you and I who get to work from home,

we're blessed with these micro moments. You get up in the morning, you're hanging with them, you get some playtime in the morning before the work time begins. You take a break at 10 in the morning to disconnect and go get some coffee or refill or water or do some yoga, whatever you're doing, whatever you're doing to this, like disconnecting for a moment. Well, you just don't walk through the living room and, and just like put your blinders on and ignore. No, you probably stop for a moment. I get a snuggle anytime I can get with my kids. You know, every moment I have with my kids is priceless. Absolutely priceless. You know, I cannot, I just love hugging my kids. They're, they're amazing. And so I call those times my micro moments. And if I was away from the home working somewhere else, I could enjoy those micro touches, those micro noon things or having lunch with them when they're home like my one son's in school five days a week now my other son's in

pre-k three days a week so I still get Tuesdays and Thursdays micro moments with him you know but you kind of get the point right like that's the blessing is like is the real I guess really the advice is is when she knocks on your office door unless it's absolutely crucial for you to say don't come in now like I used to have my son come in and meetings, like I would be in a meeting with like, I don't know. I can recall before having meetings with like century or fastly or whatever our sponsors were. And I'm like on these phone calls and I'm like, hang on a second. My son just knocked and he comes and says hello.

And he like maybe waves at the camera. It's like, Hey, this is my life, right? Just, you gotta, if you want to do business with me, you want to do business with all of me. And all of me is my ethics and my family. And so I would never deny my son coming in and bombarding. Unless it was just like something that just didn't make sense, like a podcast. Like if he came in right now, I'd be like, bud, you know, you can't come in now. Like now is not the best time ever.

But we also do edit, so I could edit it out. I just would say, she knocks answer, let it, let the office be somewhere that she can, you know, is welcome. You know, that, that it isn't dad's working. Don't bother him. It's more like, wow, I can be curious and I can explore and I can ask questions and I can fiddle with whatever is available. You know, whether you're working with hardware, working with software, just like, just be curious and ask your questions.

That would be my advice to you. I love that. I feel like whenever a meeting ends, like three or four minutes and I have like the next meeting and I'm like, oh, this is perfect. Like, let me go downstairs. Let me play around with her a little bit.

Or whenever I'm working, I hear them like screaming and talking and laughing. I'm like, I got to stop this. And I go down there and then we start playing. I wouldn't trade that for anything, to be honest. And we had like VCs ask us like, oh, are you really sure that you're going to do a remote company? Like after COVID, now all the companies are going back to in person and for me it feels

like such a hard ask to tell folks like hey you gotta leave your family you gotta you're not gonna have those micro moments like because of this thing that we are building and it just feels so unfair to i i don't have a face to make that ask. It's just so. Absolutely. Even though everybody on the team, they don't have kids yet. But I still believe like those micro moments are important with your loved ones and whoever is in your life, right? Yeah.

They're only young once. You know, you can't, that moment, I look back because my iphone is great i put that little picture widget on my phone for a reason right and i think that uh is like the one piece of magic that apple has developed in my opinion for iphone users i don't know if you're an iphone user i think you might be because you're a fan of dx and ux so i imagine that you might be i would encourage you if you don't have that widget in in yet, put it in place because every single day I'm reminded of past moments, right? Past memories. And for me, memories and making memories is what I'm optimizing for. I'm not optimizing for more money necessarily because money comes and goes. It's here and it's gone, right? The memories is

what stays in the relationship you forge and how you show up for the people you love that's what really really matters and that could be the people you love is immediate family the people you love is who you serve in your business you know how you show up for the people you love is really all that when we're measured in life some people might measure you by your things maybe by the car you drive or the cyber truck you pre-ordered and you finally got or whatever you know or the mills that you might have or the bills you might be worth but at the end of the day for me I'm optimizing for how do people feel about who I am to them and how I showed up for them and the time I gave them versus the things I'm wearing or the things I own or the money I've got in my pocket. Like to me, that's the true measure of a person.

And there's something so beautiful about doing some kind of work that in the end inspires other people to do, to be a better version of themselves too, right? Like you're leaving a different kind of legacy every single episode that you show up and you invite a guest. And then whoever is listening is like, oh, wow, this is so inspiring. Like, let me maybe change this way of living. Let me rethink about this other thing. I love that we can do that with the type of work that we do.

And yeah, it's definitely not about the things, man, about the objects. It's definitely, if that's the game that anyone listening is playing, just look at your surroundings, look at the people who are, you know, in your circle. And yeah, just check that because it's definitely, if there's one thing that we know is like, that's not the answer. It's not about the options. Well, friends, April is here. And that means that CloudF's Developer Week is also here. It's happening all this week, April 1st through April 5th, virtually.

They also have a meetup here in Austin that I'll be at on Wednesday, April 3rd in their ATX office. Check for a link in the show notes to register for that. Spots are limited, so secure your place right now. And I'm here with Matt Silverlock, Senior Director of Product at Cloudflare. So Matt, what is this week for you? Launching for developers, a bunch of new tooling, a bunch of new things that gets the next year or the next several months revived and a resurgence for new things happening. What is that to you? Internally, we call them innovation weeks, which is kind of the way we think about it, which is how do we ship a bunch of stuff that is meaningful to developers, both getting some things over the line, getting some early things out,

sharing some ideas, some things that maybe aren't actually fully baked, but kind of getting that out there and talking about it so that we get earlier feedback. But it kind of comes back to like, how do we think about innovating? And I think candidly, what's really, really helpful is kind of setting those deadlines, setting that week to kind of rally the team and get things out actually helps us get things done. There's always that tweaking for perfection, you know, another week here, another month there. It's nice when you set an immutable date, you get things out, gets into the hands of the developers much faster. Well, we're diehard R2 users.

We had an S3 build that just set us absolutely on fire. It kept growing and growing. And I was like, this can't happen anymore. We've had an affinity and a love for Cloudflare from afar in really a lot of cases until we're like, you know what? R2's pretty cool. We should use R2. And so we did, and I think I tweeted about it about a year ago, and then over time

a relationship between us and Cloudflare has budded, which I'm excited about. But why are developers, we're opting for it, but for R2 in those cases, but why are developers opting for Cloudflare products over Amazon Web Services or other providers out there? There's a lot of answers to this, but I think the one that I find kind of connects a lot of folks is we're building a platform that makes it easy to deploy, you know, reliable distributed services without being a distributed systems engineer.

Because it turns out, if I want to go and build something really reliable on sort of an existing cloud, I want to build it across regions. When I've got to egress across regions, got to pay for that. I need to make sure I'm spinning up shadow resources, right? When you deploy to workers, for example,

we just call that region earth, right? We take care of actually deploying all of those instances, keeping them reliable, spinning them up where they need to be spun up. If you've got users in Australia, then we spin one up there for you without asking you to think about it, without charging you extra to kind of do that. That ends up being really, really powerful. You get to compute closer to users. You don't have to think about that kind of coordination. In practice,

it's just really, really hard to do that on existing providers. So we find a lot of teams coming to us so they can build applications at scale like that. There you go. Celebrate live in Austin with us on Wednesday, April 3rd. Again, check for a link in the show notes for registering to that. Spots are limited and I'll be there. Otherwise, enjoy Cloudflare's Developer Week all week long from April 1st through April 5th. Go to cloudflare.com slash developer week. Again, cloudflare.com slash developer week. Let's not bury any sort of leads here. I love to go deep and talk about life and philosophy as much as we possibly can.

But, you know, I think, as I mentioned before, I've tracked your journey, been a fan of you over the years. We've had you on a few times and we've gotten snapshots of that journey, you know, here in this podcast in transcript form and audio form as well. And we'll link those up in the show notes as part of this episode. But what is a resend is a thing now i don't recall when exactly you found i think about a year ago maybe a year and a half i feel like it's a year and a half in my brain is it a year and a half it was january 2023 so 15 months okay so oh yeah i guess we're close to a close to a year almost a year i saw you met paul graham that so cool. I saw your photo with him and like, how cool is that? Right. Backed by Y Combinator. I mean, you're living the dream.

You've done it and you're doing it. I would say, you know, maybe the beginning could be like, how did you go from being very focused on developer experience at WorkOS and the various places you've worked at? How did you go from that to having an idea that was worth quitting and taking the risk and pursuing venture capital? Give me that. How did you get here? It's crazy because I feel like every single thing that happened in my career was leading up to this point. The fact that I was involved in open source my whole life made me so that I could appreciate how to build software that developers loved using. I remember back at Liferay when I was doing developer evangelism

and then developer relations and then did some product. I ended up being a CPO there before I left. All of those things also prepare me to think about like holistically about like a product and how to approach it and how to get people excited about it. And then at WorkOS, just looking at that, like how can a startup really be differentiated in this whole sea of stuff that's out there and products that we can use? So it was almost like the perfect storm was created. And then the citizenship, like all of those things were like preparing to this moment

of like, you know what, I think I'll just try to do my own thing. And not only the good stuff that happened to like all the bad stuff, all the toxic bosses that I had in the past, all the all-nighters that I had to pull because someone didn't, you know, think about their deadlines well or didn't prepare up stuff that they should have done. So, all of this culminated in this idea of like, you know what, let me see if I can make it, if I have what it takes. And I definitely don't feel like I have the answer to this yet. Like this is definitely like looking from the inside, it's still like craziness and

a lot of moving pieces all the time. But it's been a really interesting journey of understanding myself and understanding my fears. There are many moments in the history of the company where I was the one holding off because of a fear or because of an insecurity that I had. So you're just like being slapped in your face every single day with so many challenges

that you just, you see your flaws right there. You know, I'm sure you on display. Yeah, it's like it's in your mirror. And it's like you either deal with your flaw or you keep hiding. You keep giving it in coming up with excuses of why you're like that or why you made that mistake. Or maybe it was someone else's fault. Or you just acknowledge that you're like that or why you made that mistake or maybe it was someone else's fault or you just acknowledge that you're not perfect. You are full of flaws

and you're going to still keep making mistakes, but hey, you can get better. If you do this one thing differently next time. So it's been fascinating. I highly recommend anyone to one day try to build your own thing because it just opens up all of this chest of things that you didn't know about yourself. And once I open up that door, oh my gosh, there's no turning back. I don't want to hide anymore from those flaws and those insecurities.

What about, like, what role did your citizenship slash immigration process play, I suppose, in that delay? Or even aid you when you got to the moment where you wanted to pursue funding? Like, did that, was that a hindrance or a help? Like, how did that play a role? It's funny because immigration is such a tough thing to go through. Because in many moments in my life, I remember when I came in with a visa and then I was looking to get a green card. I felt like, you know that image of a prisoner with a ball on their foot? On their leg? Yeah, on their leg.

Yes. I felt like that, that I couldn't leave my job because my visa was attached to the company and I was hating working on that company. I wanted to leave. And then when I got the green card, I was like, oh, this is actually a great place to be at. Maybe I don't want to leave. But it unlocked like, okay, now I can come and go. And then with the citizenship was something along the lines of there's absolutely nothing else, like no excuses anymore.

And, you know, the fact that my daughter was born and I was thinking about like, hey, is this what I would love to do that would inspire her or that would give her a better life? I know myself. I know that I'm going to work crazy hours and I'm going to put my heart and my soul in everything that I do. So I might as well do that for myself instead of someone else. And I hope that I can cause the same transformation that other people had in my life, giving me opportunities to travel, to go to conferences and speak and all that kind of stuff. I hope I can give that to other folks too.

It was a combination of all those things. And YC was super interesting by itself because we were playing with this idea of what if we created the Vercel of email, the stripe of email. And this was just a side project type of endeavor. We're just like, yeah, let's just play around with this. And as we were building it and we're getting more confident, we're like, oh, we should apply because the process of applying is so cool. Like the form they have, like it's so nice. There's so many things you've learned just by filling out that whole thing. So we just applied without any hopes that we would get. And I remember applying back in 2020 when I built like a cheese app.

And I was like, oh, let me just apply for that. And I was rejected right away. And I was expecting the same thing. I'm like, I'm just going to be rejected right away. And that's totally fine. But they invited us to for an interview. And I was like, oh, wow, we might have a chance. Yeah, it got real really fast.

And then my mentality was, okay, am I really ready to quit? Because I have a daughter, I have a wife. Like, I'm supporting my parents. Like, I can't just leave. The idea of quitting my job was so crazy. Like, to pursue, even though I had Dracula making money on the side, it's not like, okay, I'm going to be screwed. But just that idea was pretty wild. So when they call us for the interview, I was like, man, is this idea, this, it was called Claudie back then,

not even recent, crazy name, just the only domain that we found. Like, is this idea dependent on getting into IC or not? That was a huge debate internally that I was having. So then what I did to resolve that was like, oh, let me talk to some friends that I know that they know other angel investors. So then I talked to them and then I talked to the CTO of Plaid know other angel investors. So then I talked to them and then I talked to the CTO of Plaid and other angel investors. And then I pitched them the idea

and they were like, oh yeah, we would invest. And then I was like, oh, okay, hold on. I'm not taking your money right now. Thank you. I'll call you in six months. I'll call you in six months, exactly. And then I was like, okay, so we're not gonna depend on YC. If we go to this interview

and we don't get approved, I don't really care. We're doing this anyways. And that was amazing because when we came to the interview, we had that confidence of saying, hey, we're going to pursue this without you anyways. It would be amazing if we can do this together. I feel like tapping into the YC community would be huge for Resend. You guys passed on SendGrid in 2009, and that was one of the things that Paul Graham told me in person of like, wow, that was one of our worst passes. We shouldn't have done that.

But, you know, like, we're going to do this. So instead of them having the leverage of like oh you're we're almost like we're giving you a favor it was almost like no we want to partner with you to to make this happen and then we got in and i still don't know how i'm like wow i can't even imagine i was super happy when we got the news. What was the interview like for you? How much you had confidence? And I know you have a deep aesthetic, both desire to do well and taste. You have great, great taste, in my opinion, in terms of like looking good and presenting good and whatnot. How did you actually prepare for the presentation? Was there slides? Was there a deck?

You know, who was in the room? How did they, what was the response? Did the jaws drop? Was it like, wow? Give me all the touches and feels of this moment. It's so wild because I was traveling with my family for Christmas. So I didn't have all my setup. I didn't have my mic.

I didn't have any of those things. They don't allow you to present with slides. It's actually just a 10-minute conversation. And they will make the call, yes or no, based only on those 10 minutes, which is extremely wild to think about that. It's like... Compression at its best. Yeah. No, it's crazy. And it was so much pressure. Yeah, I was so afraid of doing

that whole thing. Because I really thought that, hey, if we can get in, I think this will change our lives. I think this will change the trajectory of my career. So I really put a lot of effort into that. But there was no presentation presentation it's just like getting ready getting prepared for questions that could be any question right so that was really tough and i remember the moment i was sitting in a co-working people were like watching the the world cup games on like with their speakers super loud i was like oh my Oh my gosh, like it's go crazy. This is like the worst environment ever. And then I'm waiting on zoom. And then I see like the name, like Gustav. And I was like, Oh no, this is the guy from Airbnb. I'm like, I can't believe I'm like, I was so, yeah, I was so afraid and overwhelmed. And, uh, yeah, it was a wild experience. Yeah.

Wow. What would be your passing grade then? If you were the teacher and the interview was a test or the presentation was a test, did you ace it? How do you think you did? I have no idea. I think maybe well because I got in. But I feel like it really comes down to just communicating your conviction about that problem that you're trying to solve and your vision and all that. And that's what I try to do. And it didn't come from a place of like, oh, let me artificially generate this excitement or this grandiose vision.

No, it was, I really truly believe in my heart that this is a great opportunity i remember we we were looking for a good domain uh which then we bought like recent.com and the guy wanted like 50k and i'm like no way i'm paying this and then ended up negotiating and paid like 20k for that domain and i paid with my own money without the YC money because I was like, I have so much conviction that this is the right way to go that I'll just put all my chips in. And I feel like that came across when folks heard what we're trying to do.

Can you give us a glimpse into your conviction? I guess, I think at that time, it was a different name than it is now, but I'm sure the premise, the foundation is very similar or close to the same. What is the conviction with what Resend is today? Like where did you, how did you, I know you had, I think the React email template, I think it was like the inception parts of it, right? Like you had this very popular open source UI library for email

that maybe got you the itch. How did that happen for you? I think you appreciate this because when we were building Resend, we first started with Resend. And then we're like, oh, okay, this is looking good. Like, oh, this is shaping up to actually be something nice. And I had the pain myself. And that's why I had a lot of conviction because I'm like,

I've used Mailgun, I've used Mailchimp, I've used SendGrid, Postmark, all of those at different capacities. Sometimes as an executive, like dealing with problems of emails from customers going to spam and not knowing how to address them.

Other times as a developer integrating and then other times as just like someone on a team that is like dealing with a lot of emails that are being sent so and other times as a side project you know for Dracula just setting something out on a Saturday so I knew like that there's a lot of opportunity so we started creating this and I had a lot of conviction on building a product that was really great in a world where all the other products weren't that great. And that has something to do with the fact that they always started like 20, 13 years ago. They all have been acquired by now. When you look at Mailgun,

SendGrid, Postmark, every single one of them. And there's no player that is just coming up and trying to really rethink email in 2023. So we started Resend That Way with that idea. And then in the middle of it, we're like, oh, are we just going to come out of nowhere with like an email? Like, what's the point? Like, it's just like, oh, hey, here's an email solution.

Like, no, we're talking to all these people and they're always saying that the first problem is when they're building the template. That's when the journey starts, right? Like a designer hands you off this beautiful Figma file and then you look at it and it's like, oh, I'm going to do this with all this archaic HTML that I need to build emails. Oh, crap. And then you look for solutions and it's all super bad. And testing them across Gmail and Outlook is also super bad. So we're like, okay, so let's do React email first. Let's launch that. And we did that in December 2022.

And then let's launch recent right after. So I wanted to tell a story. And I'm really big into storytelling as a whole, right? Like what is the journey? What is the hero's journey here? And the hero journey is like, it starts with open source. It starts with first giving back. So we're going to give something. It's going to be React email. It's going to help you create email templates using Tailwind and TypeScript, all the modern tech that you're used to. And then once you have the template, you need a way to send it. So here's a platform for you. And I remember I saw this Notion doc that I found from very early

on. It had only like three bullet points for this master plan, which was build an open source project around email, establish ourselves as email experts, and then build a SaaS product for email. So that was the idea of like, and I feel like people don't really spend too much time on that. Like, what is the story that you're writing to the world? You know, like what's the sequencing? What's, I feel like those kinds of things matter. Dang, man. That's profound. And you're doing that, basically.

I mean, that's a three bullet point simplified outline of a plan, but like, the ultimate keep it simple, right? I knew that I wasn't sure what React react email what role it played in resend because i pay attention to you but i you know like the world is big right i can't pay attention to every single detail and i knew you did that first i thought that that was an itch and you're like okay now that i've done this now i found out there's this whole world to explore i didn't know the full sequence of like you know know, the, like you had said, just the ultimate plan, like serve out an open source,

helping those ways build a product that you can deliver and then assess around it. Like that to me is just, that's a great outline. That's pretty awesome. I mean, it's a really a simple execution too. It's going to have to take note. Yeah. And it comes from observation, right? Like it's not like we, we are the first ones to do that. Like, you look at Vercel, like React email is our next JS,

plain and simple. And we wanted an open source component, even though we're not an open source company, we don't plan to be. But we knew the importance of having an open source component in the positioning of the company, in the positioning of whatever we're doing. So I would definitely recommend people to just look around at what other people are doing, how they are lending their products as they are building their own.

What is the state of Resend right now like when you describe resend when you define or share with other folks in the industry what the status is success wise whatever feature wise product wise how do you how do you explain it we try to be very simple and that's the tagline we have on our website like resend is an email api for developers it started only as a transactional email API, something that you call when you need to do a reset password or a welcome email or something that you integrate into your product.

And for that whole first year, we've heard from folks that, hey, I love using Resend for that, but I wish I could also send my marketing emails. So that's something we've added recently. And we want to be this one-stop shop for all your email needs. But the vision is much bigger than that. Although I like email, it's not like I'm super attached to email as the only channel that we're going to be using. What I'm really attached is the ability for two human beings to communicate, just like

what we're doing now. So I see Resend as a communications platform, not an email company or email product. We're starting with email and we are being very intentional about covering everything that's related to email. We're now working on how to receive emails, not just sending. So that's another big feature that we're working on. So we want to nail this use case, nail this niche first, and then look around and, you know, tackle the Twilio's of the world down the line with SMS, push notification, other types of communication channels, right? And yeah, we have a long way to go.

We're just getting started. You know, the team is still super small, six people. So that has been fun. And yeah, we've seen a lot of growth this last year. Like now we have almost 100,000 users in the platform. We have like 1,400 paying customers. So we've been able to execute a lot with such a small team. And we want to keep doubling down on that idea.

Yeah. Do you have a pretty generous free tier that keeps the hundred thousand ish kind of using recent to kind of get to that value are they pretty active like that's a pretty large number like it said for a six-person team and 15 months to achieve i think why commuter probably has something to do with that the fact that they've got some connection to obviously a great product but at the same time you've you're not just batting alone you've got you know you've got some accolades behind you've got some people that have definite network right to kind of help with the awareness front which is really such a hard battle when you're a new tool

in town so to speak yeah for we were very one of the strategies that we had early on was we got to make sure that Resend is the de facto solution for YC companies. Because if YC truly is the place where the best founders are coming from, if that's a true statement, then making sure these people are happy

is going to be extremely hard. It's not going to be an easy battle. So we've got to build a really good product. So we build like this YC deal. They have like this internal place where you can post promos for companies within YC. And we got like more than 120 YC companies using us now. And we want to be on that top tier of like, if you are, you know, you're using Stripe, you're using Brex, you're using PostHog, Superbase, and Recent. That's like the stack of your company.

We want to be there early on. And the free tier plays a big part on that, right? And again, this just translates to my experience as a developer. I would hate going to this service and the first thing they ask me is to go on a call or schedule a demo. No, I just want to try it out because the way it happens is

I'm on a Sunday afternoon, 3 p.m. with my laptop and then I'm checking some stuff out. And then I see this new service. And I'm like, oh, let me give it a shot. And my daughter's running around in the living room. And I don't have too much time. I'm not even paying that much attention, right?

But then when I go to the website and I see this nice website, I'm like, oh, this is cool. And then I go to the docs. I'm like, oh, this is interesting. Looks easy to use. And then I sign up. The onboarding is cool. And then I go to the docs, like, oh, this is interesting. Looks easy to use. And then I sign up, the onboarding is easy. I can send the email very fast or do whatever I want to do in the product. And then I can start using, oh, this is a great experience. Let me talk to my team Monday morning and let me show them that, hey, I built this POC over the weekend in 30 minutes. We should maybe use this at work.

And the opposite is also true, right? Like if you go to a product and then the website looks a little bit weird, you don't really understand the messaging. You go to the docs, it's confusing. There's a lot of stuff going on. You sign up, the confirmation email takes five minutes to arrive. And then once you get it, you click

and then you're like, oh, how do I even get started? It's not clear. And then that's a product that you're just not going to remember. You're not going to tell your friends. So for me, it was really important to get those things right. It needs to have a generous free tier. It needs to have like a great onboarding because otherwise, yeah, we're not going to be remembered. Well, friends, I'm here with my good friends over at Cinedia, Byron Ruth and David G. And as you may know, Cinedia is helping teams take NAS to the next level via a global multi-cloud, multi-geo and extensible service fully managed by Cinedia. They take care of all the infrastructure, the management, the monitoring and the maintenance, all for you. So you can focus on building exceptional distributed applications.

But before we even get there, we have to understand exactly what NATS is. So Byron, when you get asked to describe what NATS is, what do you say? How do you explain it? It allows an application developer to adapt and evolve their application over time and scale it based on maybe the unknowns that they have at the time that they started the application. How that manifests is really in infrastructure complexity, developer components that you have to bring in, whether they're streaming things, storage things, whether there's operational complexities about multi-tenancy and considering the security, a consistent security model

around how your client components can talk to one another. And once you start evolving your system, scaling your system, you're inevitably going to have to, especially at the connectivity layer, bring in load balancers and proxies and network overlays and things like that. And NATS provides you the foundation that allows you to not need to introduce those additional things. You can Lego brick your NAT servers together to scale out to sort of a topology that you need or use a managed service that Sanadia offers, for instance. And you don't have to add primitives that are very common when building an application like KV and object store and streams and things like that. That's all baked into NATs. And so what inevitably will happen is that you start out with something

simple, simple request reply, and that's fine, but you're going to need to adapt and scale depending on your use case and your needs. If you start with NATs, I think it gives you a better foundation, not needing to introduce additional dependencies as you adapt and scale your system. I've got a total curve ball one here. A curve ball? Yeah, total. Okay. Let's hear it. Oh, please do.

I'm not going to talk about NATS. I'm going to describe what NATS is. NATS is an intergalactic ready video conferencing system, like your favorite sci-fi show. When two ships pull up side to side, they open a hail channel, they talk. They might not know what the language is, but the channel opens, communication happens. So what happens when you open a video call? Two people might talk, multiple people might talk, the ships themselves might talk. So what we're

saying here is NATS gives software the ability to have point-to-point and point-to-multipoint communications irrelevant of where they are, irrelevant of how they're connected and irrelevant of what languages the connecting software is written in. It's a video phone system for software. And if you want voice recording, you can have that as well. We can add the ability to make sure things and conversations are recorded for playback. Yes, that is a curveball. Thanks, David. Well, there you go. Today's tech is not cutting it. NAT's powered by the global multi-cloud, multi-geo, and extensible service fully managed by Cinedia is the way of the future for application developers. Learn more at Cinedia.com slash changelog.

That's S-Y-N-A-D-I-A dot com slash changelog. Again, S-Y-N-A-D-I-A dot com slash changelog. you have gotten funding we kind of skipped over a little bit of that and you're kind of touching on what i think is a point that you can afford to, which not everybody can afford to do a generous free tier. That's obviously marketing, but you do have to have the burn rate or the cash for the burn rate to be that generous and to get to that adoption rate. Can you speak to, I guess, the venture capital behind you and what it took to have the financing to be able to do these kind of things? And really what it takes to run the company from a financial standpoint. How deep are you in those details? Is it something that you like to even pay attention to, or are you super product and UX and DX focused, and CFO does that?

I just check a report. How does it work? I wish we had a CFO. That would be super nice. But man, this whole journey with venture capital was super interesting because I've seen the other side. I've seen what is it like to do a project as an indie hacker. And I think we sold like $300,000 and something thousand dollars with Dracula Pro. So I was like, this is definitely a valid path. Like we could build Resend as a bootstrap company. That was one option on the table.

But then looking the other side is like, if we do this with venture capital, we can do that type of thing. We can be generous with the free tier. We can build stuff that is more refined than just like ship it and then be very, I don't know, like you have so much more constraints. So we were very intentional about going that route.

And that's why we took YC, we got into YC and then took their money first. And I remember this was back in March, April. Approaching fundraising was so hard because I've never done that myself. Like this was so new. Like how do you talk to VCs? How do you behave? The little games that they do, the back channels that they use to get more information about you.

It's just a super weird game. It's so crazy. And there was a lot of interest around recent because we're getting a lot of traction. We wanted to present ourselves as like the next big thing, not just like something that is being validated. So that's why we got recent.com. We came up with a nice website. You go, you see this weird Rubik's Cube rotating on the homepage. You're like, whoa, what's that?

And all those things were there because we wanted to create a sense that, hey, we're here to stay. Like I remember something super weird and funny. It's like we wanted the footer to have a lot of links because when you see a company that is more established, they typically have a lot of links on their footer. So we're like, oh, yeah, we got to have a lot of pages on the website. So going through that was super interesting. And a lot of my peers at YC, they were like raising money from funds for their seed round. And we did the math and we're like, OK, maybe we could raise like $3 million. I think that would take us to the next step.

There's this thing with fundraising where even if you can raise more, which was the case for us, we intentionally kept the round smaller because you don't want to dilute yourself as much during that point. And we had all the big funds that you can think of, like Andreessen Horowitz, Sequoia, all the big ones coming after us for a reason and we're like no no we're not gonna raise from funds we're only gonna raise from angels and you know that's when i talked to guillermo rauch from vercell which then introduced me to dylan from figma and i i couldn't even imagine that i was talking to those guys. I was like, these are the people that I admire so much. The founder of Segment, the founder of Superbase. These are the creators that when I look at their products, I'm like, yes, this is it.

I wish I could have done something great like that. So we only took money from angels during that first round. And that was another thing by design. Because during the seed funding, we're like, this is the moment where you get angel investors in. Because like Series B, Series C, you don't have room for that anymore. So let's just capture that right now. And these are the people that are going to give us the right advice because they've been through that. It's not like someone that just works with finance and doesn't really know about how do you get to product market fit. The only thing we're trying to get is to product market fit right now. And at some point, we're going to need like those finance folks.

And then the right time will come. And then I'm sure we'll have them on our side. But just doing all that stuff as a developer, like raising money, building decks and all that kind of stuff was super, super interesting. Yeah. Super hard. Wow. I don't know how I missed that detail that you were that your seed round, your first funding was only from angels. I didn't, I gapped that somehow.

I'm happy to admit it because I don't mind being wrong in life. I feel like it's something you should, if you're wrong, say you're wrong, you know? And if you're sorry, say you're sorry, that kind of thing. But that's cool. How did you approach that then? How did you, I guess, one, how did you turn down the biggest funds in the world, basically? What was your literal response? If you can TLDR it or somehow give a bridge version of it, cool with that.

And then two, how did you begin to develop the list of angels you wanted to go with i know you talked about guillermo and then dylan and that kind of thing but how did you then map out to all the others because there's several of the of the folks you have in your angel list that i'm personally aware of and know as well and how did you reach out to them did you have an email not template but did you have like a script or a thing you'd written like, hey, I'm only raising from angel investors. I've been a fan of nowhere. You want someone that respects that other person that you're trying to get to, to introduce you. So that was the path that we tried to go. Not like cold emailing folks, even though I think I've sent some of those, but I would just name drop people that I admire. And when I was talking to several people and then like one of

them would connect me. And by observation, looking at these other successful companies and looking like, oh, who is backing them? And sometimes it was just like individuals, like I would see Cassidy Williams, which I love. She's such an amazing human being. I would love to have her on my side. I feel like she gets what it takes to build developer products. So let me talk to her. Call Ving from segments. You know, like he gets it. James from post hoc, he gets it.

So it was like through introductions, navigating this maze of introductions. And then when getting to these people, just being fast, being direct to the point, sharing that vision. And I feel like as creators, it's easier for them to say yes or no. I got many no's too from people that I really wanted on our side. And for about the funds, it was about taking the meetings and acknowledging and being very transparent that, hey, we want to work with you, but we just don't know if this is the right time. And they totally get it. They're like, this is a long game. You're probably going to need help during the series A. Don't worry. Let's continue building the relationship. And that also shows their personality, right?

If they back off and disappear, okay. Maybe I actually don't want to work with them because I'm doing this for the next 10, 15 years. I'm not doing this to sell out in a year from now. So this is going to be a long journey. If you want to be here for that, I would love to do that with you. So it's definitely like a relationship where you're just evaluating folks. And for me, raising like we did, like $3 million, it was so much money. It's like, wow, this is insane.

It's just so much money. Turns out for every single person that we talked to, we had to decrease their check sizes because they wanted to invest more and we didn't. We wanted to optimize to like only 10% dilution as founders. So we're like, no, no, no. Oh, you want to invest a million? We're only giving you 500K allocation. Oh, you want to invest 200? We can only give you 100.

And it filled out very quickly. We started the fundraising process Monday morning and we scheduled a whole week for calls. Wednesday morning, we were done. We were oversubscribed. So it was all very, all happened very fast. So you had a dollar amount cap per angel. Did you, you got an easy number. If your number on the website is accurate talking to some of like, you were like, the cash allocation would matter more. So then some people I'm like, wow, I really want to work with you. Even if you can only do a 5k check. That's fine. Let's do it.

I love your work. You know, the respect is mutual. Let's do it. So it's less about the number of angels, more about like how much is allocated, which is like a Tetris game. Because as you get bigger checks, you get bigger checks, then it's like, oh, now I have less space. So when do you think you'll raise again? I know the landscape of fundraising right now is getting better this year. Last year was really bad.

It's getting better this year. I've heard from many folks like do you need money do you want money when's the right time do you do you think about that and are you so are you just totally focused on product and product market fit or have you reached product market fit like where are you at with i guess generally a good next step i share the same sentiment as you described like we i feel like it was pretty bad last year. It's getting better now. But we're not in a rush.

We can wait more time. Like we've been able to grow with bigger customers recently. So it's been giving us more runway so we can have more freedom in our decision making process. So we do have a number in mind that we want to achieve in terms of revenue before we start talking to more folks. But it's also the case where I think about that all the time. It's like definitely on my mind every single day,

but it's not what keeps me up at night. What keeps me up at night is how can we deliver a great product, a great service? How can we not have downtimes? How can we, you know, every morning I wake up, I'm like, oh, let me just check if the servers are still up, you know, like that kind of feeling of like constant stress and constant like caution and watching out for everything that's happening.

Yeah. So, yeah, we're not in a rush. Maybe it will happen next year or end of this year. We'll see. and i guess this would be your official a round right because like this one this or is that still you're in the i guess an angel round is a seed run round right like that's how you would categorize it so series a is still that's your next step is series a some people raise like seed extensions that that's another path but yeah i feel like the next one for us could be a serious act do you think the next round would have a mix of you know maybe

reallocation to existing angels maybe some new angels and funds as well like what's your thoughts on how you expand and i mean because really what you're offering really is you've got some conviction you got some awareness where you're, and you're offering an opportunity to folks, not just simply people coming to you who really appreciate what you're doing and wanting to invest in your company, but you're also saying, we're going to go here, and here's an opportunity for you to be a part of that. Not just simply the funds, but maybe more angels that are out there that respect you and appreciate you and want to invest as well that maybe didn't get the invite or the friend of the friend invite or the introduction or whatever.

Cause you know, when you've got 28 angels in your first seed round, realistically, that's not a lot of people. It's a lot of people kind of, but it's not a lot of people when you've been in as successfully as you have been in the industry. I think 28 people's not nowhere near your network, like nowhere

near the amount of people you could have had in your seed round, for example, from Angels. Yeah, it's definitely the case where you would imagine that the hardest thing to get is capital. But in reality, the hardest thing is like getting people that share the same vision of the world or share the same passion for serving developers. And that takes time. You know, like when you're serving developers, it's a different kind of business model. You need patience.

Or you're going to target enterprise companies too early in your journey before you have all the things you need in place. So it's about finding that right partner that you want to, you know, grow with. And that's extremely hard. That's much harder than like, oh, yeah, let me just, how can I get $10 million? Like, you would think that's extremely hard. And I'm not saying it's easy. It's extremely hard, but even harder than that.

It's both easy and hard. Yeah. It's easy and hard. Yeah. So, yeah, we'll see how it's going to turn out. But I think it's what you described. It's like a mix of more allocation for some existing angels, maybe bringing a few more, and then probably a fund, which is what typically happens on a Series A. You give a board seat to a fund and now you start like building that relationship. And that's why it's so important to pick the right person because now you're going to have that person for the next 10 years in your board.

It's like marriage. Yeah, right? Possible cancer even. Proxicity is totally an option. Yeah. Yeah. I've seen Silicon Valley, the TV show. Exactly.

Yep. So many times. So many times. So many times. I love that show. I mean, that thing's basically a Bible of what to do and what not to do. And what's possible. And it's so, it's satirical, obviously, but it's also, and satire is obviously so close to reality.

So close. In a lot of cases, but it's, I mean, obviously, but it's also, and satire is obviously so close to reality. So close. In a lot of cases, but it's, I mean, yeah, anyways. I don't know if you're a fan of that TV show or not, but if you are, then we're even better friends than I have alluded to because I absolutely adore that masterpiece of a show. Totally. I'm watching now again. I guess, I don't know, maybe the third time or something. And it's funny how it's still accurate. Because some shows, they don't get old well.

This one, it does. Everything is still there. It's crazy how super up-to-date still. I'll share a small aside then that's tangential to the show that we're doing here today, but very close to Silicon Valley. There's a character in season six named Gwart. Are you familiar with Gwart by any chance? Mm-hmm.

Friends with Brian Cantrell of Joyent fame and now Oxide fame. He's been on the podcast before and he's a big fan of Silicon Valley. We're in DMs on Twitter podcast before and he's a big fan of silicon valley and we're in dms on twitter slash x and pretty much all we talk about is just silicon valley i mean occasionally things that matter like the industry and other things but like it's pretty much just like trading silicon valley riffs of sorts or screenshots or whatever and he's like hey you

know that gward had a cameo in season one right and i'm like no and then like he just like didn't talk to me for like a week and i was like come on don't leave me hanging here what's tell me he's like oh i'm sorry i didn't tell you i left you hanging and so he tells me in season one episode four there's a gward cameo so oh wow the actress who played gwart was an extras actress at the time. And so it's not really Gwart. It's the person who played Gwart eventually in season six. All this to say is that I was like, after Brian told me this and I found this out, well, I found the actress's website. She seemed super approachable and they had a contact form.

So I'm like, all right, I'm going to reach out. And so I reached out to confirm one, that it was the cameo was true and then after that the it wasn't and I forget her name I'm so sorry the actress who played Gwart I'm like so only in only knows Gwart her handler or PR person whomever however you would phrase that person's title or role was talking to me and I said hey do you know do you think that she'd be down to pod with some super fans of Silicon Valley? And she responded with, yeah, let me figure out some time. And so the, the plan at some point in the near future is to have a show here on the change log, probably on friends or Friday talk show with the Gwart actress actress just riffing about silicon valley no way i got oh my gosh

i'm so looking forward to that though that's gonna be awesome yeah i mean i'm such a fan of that show i mean i could literally just like stop podcasting right now about resending just talking about silicon valley the whole time but i'm not gonna do that but that's how that's what a fan i am i think it's just an absolute masterpiece and anyone anyone out there who says I don't watch it because it's too close to the vest or too close to the chest or is too close to reality for me or PTSD, I really do understand the literal not truly PTSD. So don't give them that credit. They're missing out. They're missing out absolutely on like a masterpiece of a show. Masterpiece. Yep, for sure.

And you could probably attest this because you're like, Richard Hendricks was looking for a Series A and finally got it. I think it's in Season 2. That's kind of like you're in like end of Season 1, Season 2. You're just past TechCrunch Disrupt, which was really YC for you. And now you're in season two, potentially going to get removed from your board if you get the wrong person into your board, which is the whole reason I brought this up is because like the toxicity in the board is, you know, elucidated very well in this whole entire show and i think it's like in a way of to do and what not to do in you know literally silicon valley or just in the software industry which tends to like revolve around you know california and sf and it's not your philosophy page says you know not everybody

lives in sf or new york or you know all these other cities in the world we'll get into that as well but like it very much revolves around the silicon valley way yeah right man watching that show as a regular developer at first then watching now as a silicon valley founder like living in sf like it's just so it's extremely close to reality like it's so i i'm getting i'm understanding some jokes that I'm sure I couldn't understand the meaning at first, you know, so it's so. Like negging? Yeah. Right?

Yeah. Well, you were talking about, I mean, I don't think you probably had this problem with your angels, but giving too much or taking too much. Like that one founder of, I think it was Gooley Bots or something like that, or Giggly Bots or whatever was the company name. He took too much money taking too much like that one founder of i think it was gooley bots or something like that giggly boss or whatever was the was the company name he took too much money yeah down round season two right as a ceo like that's a total reality right total reality you take too much you get pressure because you don't know like you were saying before i've never raised i don't know these things and there's etiquette and there's also like should you take too much should you take too little if you take too much? Should you take too little?

If you take too much, you, you, you will naturally have a down round because you won't gain the momentum. You won't gain the revenue. You won't gain the valuation. And so therefore you can get pushed out as a CEO, original founder, and essentially have your company taken from you.

And that's, if you choose the wrong venture capitalist to work with or the wrong fund to work with, that's totally a possibility. That's like they're not really predatory, but they obviously have their own self-interests in mind whenever they invest. And some have great mindsets and great intentions. And some are really just in it for the possibility of acquiring a company, a funding company and taking it over. Just crazy, right?

Imagine like taking your baby from you. acquiring a company you know a funny company and taking it over just crazy right imagine like it's crazy taking your baby from you you know like wow like you spend so much time building that thing how dare you yeah right so it's so wild i mean i don't want to call it predatory because i don't want to like blanket it that way but that kind of that kind of action if premeditated is totally predatory. Right? Like if you purposefully overvalue, overfund based on evaluation, and you know, or you have an inclination that they may not have the ability

to raise at the next level and get to a series B and they're going to have a down. And you know, that's a possibility. You do that on purpose. And that's totally predatory. That's evil, man. That's plain evil.

Pure evil. It's the ultimate version of evil, man. That's plain evil. Pure evil. It's the ultimate version of evil, man. So you're in season two, basically, with Resend. Yes. Season two with Resend. Yep. Hopefully I don't get taken out. Do you have an Ehrlich in your life?

Oh, man. So we joke that my wife is Ehrlich. Is that right? Yeah, we joke about that because she makes some jokes that is like totally or like yeah ah do you have a richard then i don't think so maybe no my co-founder yeah i don't have a gilfoyle gilfoyle is my favorite character i absolutely love gilfoyle i mean the best i mean i really love them all but gilfoyle's my favorite character. Gilfoyle, yeah. I absolutely love Gilfoyle. I mean, the best. I mean, I really love them all, but Gilfoyle is like, if I'm ranking them, I'm thinking like, you know,

there's times I like Richard way more than everybody, too. There's times I like Donald, really. Yeah. But Jared is his name. Jared is so good. His real name is Donald, though, you know? There's times I like Jared as the character the best. I have been Flo, but I think they all are a stellar cast

and a stellar set of characters. But Guilfoyle, really, he brings it. He brings it so good. Let's go back into Resend. Okay, so we're in Season 2, technically, of Resend. This year, maybe next year, funding. I've got to imagine that the challenge, like you had said, was not really getting to the money figure because if you can do well in this industry and put together a good network

It's it's not too challenging To have good. I mean, I guess good to challenge you have good It's it's not too challenging to like build out a network that wants to believe in you and give you An opportunity like you have done with your angels I'd imagine email generally just dang hard from deliverability to certificates to be trusted on the internet to like, how in the world do you build a technical stack? Like I've known you to be more on the front end and more on the DX and the UX side of things and less on the, not so much the technical parts, but like this deeper archaic back end area where like i don't think

there's a lot of people who have a lot of depth in email deliverability how did you get there what were your partners like how did you get the technical ability to deliver the emails that resend does and like i think the the ux side seems to be pretty easy for you because you've got skills on the front end you've got taste you, you know, beauty has always been part of the things that I think you've produced that I've seen. But the challenge seems to be like the real hard stuff, the deliverability of email, the all the things that are involved in sending email period. How did you get there? I think if I knew all the problems that I would face, even on still on season two, I probably wouldn't have done this.

Like, it's so hard, man. It's so hard. Like, there's a lot that we are learning as we go. And I feel like that's the beauty of Resend in a way because we are outsiders of that email industry. We know how to build tools for developers. And we know about email to a certain degree. But it's an industry that as you go deep, I went to an email conference recently.

It's actually an anti-abuse conference. And that conference was doing, it was their 20th year edition of that conference. Dang. That's a lot of years. How does this even exist? And it turns out when you go there, like there's all these folks from Yahoo Mail and Outlook and Gmail,

all the people who are actually building that kind of infrastructure. And they're all talking about how can we prevent abuse, phishing emails, spam at scale, right? And we see those problems every single day. Like, in fact, one of the reasons why we started Resend was because I remember going to all these other services and you sign up and the first thing that they ask you is like, oh, okay, you want to start sending emails?

Fill out this verification form and then wait two days and then we're going to get back to you and tell you if we're going to allow you to send or not. And I was like, wow, there's no way as a developer that I'm going to go for that flow. I want to send my first email and then if it works, then I might be able to fill that out later if it's really important. But I just want to get this over with. And now I know why these forms exist because there's so much abuse. There's so much difficulty in making sure that the emails

are going to land on the primary box and not on the spam folder or the promotional tab. But I feel like you kind of need that naivete. Like you need to be that naive to go and say, oh yeah, let me take on SendGrid.

Let me try to build the next Twilio. Like you gotta be really naive to think that you can do that, which is actually maybe a good thing in a way. Yeah. Well, we know it's hard. How well do you think you're doing at the hardness? Like, are you pretty good at email delivery? I mean, you can't just be pretty good. You have to be

really good, right? To be considered enterprise or worthy of even taking a dollar. Yep. And there's definitely different expectations, right? Like folks that sign up and they pay $20 a month, they have a certain level of expectation. But now we're closing people that are sending 3 million emails a month, 6 million emails a month. And now we're at a scale where now that we're sending dozens of million emails a month, it's like, how do you process all that data? It's so much data to process. How do you store that data? How do you make sure that you have the right observability in place so that if something is not going well, you got to fix it. So I'm very lucky that we have like a lot of

great people on the team that know a lot about all that, You know, like we have folks like Boo, my co-founder, who is, man, the best engineer I've ever worked with. Like he's so good. He's so fast. He can build stuff that, yeah, like very few people I've worked with in the past can do. And Vitor, who used to work at Spotify and now is at Resend. So people that have seen big scale, they know what it takes. And they also know the trade-offs because we can't just be operating like we're Spotify because we're not. We're a team of six people.

We need to move fast. So you got to make trade-offs all the time. So that's super hard, especially if you want to do that combination of we want to have great quality and we want to move fast. Those things are in tension all the time because if you want to have quality, oh, it's going to take a long time to deliver that quality. Oh, you've got to move fast? Okay, let's just make it not good and then we can ship fast. So, the secret that I've found is, no, you're still aiming for both of those things. You're not going to make trade-offs on quality those things. You're not going to make trade-offs on quality or speed. What you're going to make trade-offs is around the scope. So we're

going to have to cut some features, cut some scope so that we can deliver both at the highest level. And that's the way that we operate. And that's on the front end, that's on the back end, that's on the infrastructure level. Always thinking about that minimum version that is at both levels. We call this like V zero all the time. We're like, oh, how can we ship the V zero of this project? What's the very minimum, but it needs to be really good because that's what Resend is about.

We're not gonna ship crap. So how do you do that? Super, super in practice practice extremely difficult to do because it's about saying no's and you don't want to say no to that one thing that you believe really cares you know so when you think about the team you've had to build then like you've got ops you've got you know uptime you got sres this is like a whole new world how do you build out your infrastructure like what kind of infrastructure you do you build out your infrastructure like what kind of infrastructure you had to build out to make this even possible from a server standpoint

tell me all that yeah i think i got lucky with the fact that when i was before i worked i was i was at a company called live frame and this company would sell this on-prem software to big companies. So think of like the McDonald's of the world, Pizza Hut, these really big companies. And that product, like they existed for like maybe 10 years until the point I got there. And then we heard about this new thing called Docker. And we're like, oh, so now you can put stuff on the cloud much more easily than just giving like a Java bundle, which was how this portal was built. So I had this opportunity of like me and a coworker to start this Liferay cloud division, which was at first just like an experiment of, oh, how can we put LiveRain in the cloud and maybe build our own paths? So we kind of built our own Heroku or RayOA or Render inside the company for this product,

which then became like a whole thing. We had to actually start a separate division. And we grew the team from just me and my co-workers to like 70 people. And then we went from like running our own Docker containers and then Docker Swarm came up and we started using that on AWS. And then Kubernetes came up and then we moved everything to GCP. So I've seen that firsthand, which was really good because even though I wasn't an infrastructure guy, I was like, oh, so this is how it works. This is like how you deal with these type of people, right? Like it's a different skill. Like I've met DevOps engineers that doesn't even know how to write like a single line of code, but they're extremely good with shell scripts

and they know how to scale these kubernetes clusters like like no one else can right so i feel like that experience equipped me to do recent later so that now that we are facing all these scaling challenges like at least i have a framework to go about it we still don't have kubernetes we still don't have all this infrastructure like I used to have in this other company, but at least a mental model. And it's so funny because me and my co-founder, we sit down and we're like, okay, we're having this scaling challenge. How can we solve it? And then we model this architecture, which we think by the end of the conversation, we're like, okay, this is definitely going to hold at least nine months, right?

Like, I'm sure this will be great for the next nine months or a year. And then three months goes by and we're like, oh, actually, now we've got to rethink everything again. So scaling is something that now for the first time I'm seeing in a different way that I've ever experienced in my life where you are constantly rethinking the way you do things. And the decisions you made last month are maybe not the right decisions that you need for the next year, which is super, super interesting. It moves so fast. That's challenging. It's a good challenge, though, right? I mean, you want to. that's a good problem to have. It is a hard problem, but it's a good problem to have. Given what you have to do, what do you think is over the horizon for you? Is there

anything that maybe not many folks know about? I know that in the pre-call you mentioned the philosophy page. I think it's like, I think you lead a lot with story like you mentioned before earlier in the in the podcast but what is next what's a big next thing for you not many people know about you can share on the show in a way i'm tempted to say feature a b or c as the next big thing that's coming up but i think the next big thing is delivering on that promise of, hey, uptime is like water. Like uptime is crucial because frankly, like we did have a downtime in January and then another one in February and our uptime is not looking great. So we got to address that. We feel like we've done a lot of things to build the product with great quality.

Am I 100% satisfied with that? No, there's a lot of stuff that we still need to do to make the product really, really exceptional. So if we go down that list, just fulfilling that promise is the next big thing at all levels, like when you have an issue, you go to support. I feel like we do a great job today. But do we do such a great job that you have to tell your friends about it? You're like, wow, I had I had this issue. I talked to their support team and then they fixed it a hoodie in the end. And I'm like, wow, this is so incredible. Like I can't help myself, but share the word about it. So pursuing that excellence at all levels is the next big thing, which is what we try to do every single day. And most of the times we fail, sometimes we get it right. But yeah, that's what we sign up for. What about you then personally? Like what do you focus, on the daily? Like in a month from now, what is your focus?

Man, that's, that's probably the hardest question of this whole thing. Yeah, I feel like I have so many gaps as a leader that I need to fill. I don't think I'm the best salesperson, you know, when I'm talking to enterprise customers, you know, when talking to enterprise customers, you know, there's a lot of things that I never had to sell a big contract. So now I get to learn how to do that. Sometimes I, there was this one candidate that we're interviewing this week and then last week, actually. And then they, he told us like, oh, I have this other offer. And he was super interested on us. We were super interested on him.

And then because I was moving to another house, I dropped the ball on the reference checks, the last step of the interview process. And then he ended up accepting another role and not our offer. And I was like, that was totally on me. I should have done a better job just following up quickly because we are a startup. We should be having that competitive advantage or delegated to someone to do that job. And I failed. So I feel like just getting better at project management, at recruiting, at sales, at product.

I feel like there's just filling those gaps. It's probably not going to be the task for next month, but for the next 10 years, which, yeah, it's interesting. I like that. Well, it begins with self-awareness, right? The fact that you are self-aware is a positive. It's not a negative. And we-awareness, right? The fact that you are self-aware is a positive. It's not a negative. And we all have gaps, right?

I think being aware that you have gaps and being willing to say you have gaps and admit you have gaps, not just to me or others, but to yourself even, because sometimes we're just so narcissistic and egotistical that no way can I fail or have gaps. My gosh, do you know who I am? Kind of thing, you know? Self-awareness. It begins there. That's the key, man. Well, it's always good catching up with you. Big fan, obviously. Big fan of Resend. Big fan of you. And wish you nothing but the best. Not just in business, but maybe even more so with your wife and your family. To me, that's why I show up is my kids and my wife and my people, I say.

But definitely a big fan of what you've done, and I'm proud of you. I'm excited to have you back on the show in a whole new role as the role of founder and CEO. You're leading well. We all have gaps, sure, but you're doing well, and I'm proud of you. So thank you for coming on the show. I love how we started talking about family family and we're ending talking about family. That's what this is all about.

I love that we have this friendship, even though we only had time to talk like three times on a podcast and somehow we got super deep those three times. And I really appreciate, man, all the work you have done for the community. Whenever I hear about the changelog, it's always great stuff. At every company that I worked at, when we thought about like, oh, how can we get more awareness? Oh, let's sponsor the changelog. Whenever we asked the engineers like, hey, engineering team, how can we, like, what are your favorite podcasts? They always bring up the changelog.

When I talked to the team this morning and I said, hey, I'm going to the changelog, they're like, oh, really? Oh, that's so cool. So I really appreciate all your work. I know it's not easy. I'm sure there are days that you're like, oh, okay, let's do this. But you're still doing it for such a long time at the highest level. So thanks for everything. Well, thank you for saying that. I really appreciate that. It definitely, it is hard work. Jared and I come every single day and we show up and we do it and

he's done. And I feel like that's really what you got to do. You got to love what you do. You got to love the people you're doing it for. But it is, hard work but it's also very very rewarding you know like all hard work it's it is rewarding and i but i do appreciate you know you saying that and then for coming back on we'll have to find time at some point when we're in the same city and and literally hanging together or just like make time to do it it's it's uh it's not easy for sure sure. We've got to do that, man. Thanks again, Adam. Very cool. Thank you for coming on.

Appreciate you. Well, maybe now is a good time to go give a loved one, a favorite person in your life a hug. Maybe even a kiss if it makes sense. Tell them you love them and appreciate them. We did start off the show talking about family and the things that motivate us, the things we care about deeply, basically the reasons why we show up. I know for me, my family is a massive reason for showing up. Some people are motivated by just their work and that's okay. But for me, it's my family, really. I do everything I do for my family. And as you know, I'm a big fan of Zeno based on this episode. I won't gush anymore, but I'm also

a big fan of Dracula, the theme that he created. And I've also bought Dracula Pro because, you know, I got to put Dracula everywhere I want. And Dracula Pro is so cool too. But I'm not, and when I say I, I mean us, we are not Resend users yet. And maybe we'll change that sometime soon. We'll see. But this could be your chance to become a Resend user. Check them out. Resend.com. Big fan of Zeno, as you know.

And so he's got my endorsement. Okay, big thank you to our sponsors for this episode. FireHydrant, you know I love them. The new hotness in town. I love that pun. On-call solution, FireHydrant.com. Check them out. Signals is out there for you to use.

If you're using PagerDuty, you just might be wrong. And to our friends at CloudFlare, big, big fan of CloudFlare, was just at their developer week meetup last night at their office in downtown Austin. So cool meeting everybody, saying hello, catching up, hanging out, all that good stuff. Such a cool office. And also to our friends at sanadia yesterday's tech is not cutting it nats powered by the global multi-cloud multi-go setup they have is so cool fully managed nats by sanadia it's the way of the future and of course to our partners our friends

our home fly.io. And of course, a sentry. Use the code SHINGELO to get $100 off the team plan. Don't sleep on that. Use that. $100? Team plan? So cool.

And those beats by Breakmaster Cylinder, so, so banging. Love BMC. Got some new beats coming out, too. Keep listening in our interstitials, and you'll hear them as you probably love them too. Okay, this show's done. Thank you so much for listening. Stay tuned for Friends.