Getting to Resend

Well, we’re back… It’s been too long, in my opinion. I invited you earlier this year. You got super-busy, I 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; 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.

Zeno, right?

Yeah, it’s Zeno.

Okay. Well, I was talking to Michael Greenwich not long ago, and we were talking about you, because he was on Founders Talk, and 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 to 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 “Zeno.” I got used to it now. But yeah, Zeno works, too. Either one works.

Okay. Alright. So either, or. Zeno or Zeno, and you’re cool with that.

I’m totally cool with that. Now I feel better again, because considering the intro, feeling like we’re friends, and here I got a friend’s name wrong, I feel like a jerk… Gotta fix that right out the gate, you know?

[laughs] Yup. Yup.

But 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 from an injury, to accidental open source, to leading in a lot of ways in open source, and building in public, and being very out there with your ideas… Obviously, I just mentioned Michael Greenwich, and WorkOS, and we’ve been sponsored by them before… I’m a fan of Michael. I’m a diehard forever pry-it-from-my-hands-if-you-can Dracula user… I like the way you say it better, that you say Dracula, which - I love your accent, the way you say it… Because I just say Dracula. But I love the way you say Dracula. It’s so cool. And then now, founder! Congratulations! Holy smokes… What a journey.

What a journey, man.

Right?!

And there’s definitely a lot that inspired me during my time at WorkOS to start this off. Just seeing how a small team can operate, and see 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 funnily enough, it was close to the time that I got my citizenship, so I was like “Oh, now I can live the American dream fully. There’s no strings attached… Let me just go all-in”, and that’s what came out of it.

Before we go into this new journey for you, can we touch on some personal stuff, too? Do you mind?

For sure. Let’s do it.

I follow you – I think I may have seen on Instagram, potentially; I don’t know where I saw it, but – I think I follow you on Instagram. And I’m barely on there. I’m just like a lurker, I’m not a poster. I saw you got married, I saw you had a child… And I saw some key moments in your life that really matter. Can you share some of, since the last time we talked, like, change in your life? You mentioned citizenship, and obviously founder, but can you share some of your journey in life, I suppose?

[00:07:58.05] Man, having a daughter was just something that really changed my perspective. It’s not like I changed as a professional as much. I continue to be a workaholic, and things that maybe I’m not that proud of… But definitely as a human it just changed the way I see life. And a lot of the decisions I made professionally were because of that. So obviously, me and my wife, we’ve been here in the US now for nine years. I recently moved from LA to San Francisco; that was another big change. And all of those things together, the fact that we are here alone as a couple, we don’t have family around… And now growing this human being - it’s just like super-wild.

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. We have friends who go on date nights frequently, because they have parents nearby. And so it’s hard not to be jealous of that, because it really takes a lot… It takes us to move a small mountain, basically, sometimes maybe even a big mountain to get that together time, where we don’t have our two amazing kids around us… But similar. I think we’re blessed with kids, because kids provide perspective, really. I see my face in my youngest, in 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, they’re still children, one that’s now an adult. But all three of them have provided unique perspective and unique feedback into how I operate life, how I think about life, how I show up for life. Not just to succeed or to do awesome on 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 pushing things away that don’t really give me the things that I’m optimizing for… And fine-tune 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, do you think you would still be doing the podcast if it wasn’t for them? Because that’s something I really admired about you; 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 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…

Congrats, man.

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, but you did ask… It was only till recently that 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 band, and we do a mobile podcast setup… It’s amazing. It looks cool. We’ve got two TVs there with all of our YouTube clips… It looks super-cool. And my kids - they see me go to work, and they hear really - because one of my children is really into music, and so he loves Breakmaster Cylinder, our producer of our music, right? All of our music is custom. And custom-licensed for us, too.

[00:12:04.23] And so they get to experience the podcast, and they get to like see it from like the fringes… Like, they know what I do, and they hear the music, and they hear the content, because I’m like listening sometimes… I call it “Hey, I’m QA-ing this podcast.” I’ve gotta listen to my own stuff, to pay attention, to fine-tune and get better. But they didn’t get to see the thing in real life. Like, they see me go to work, they see me talking into a microphone, they see the lights and the cameras and stuff like that… But to see me at a conference and people coming up and meeting me and Jerod, and giving us hugs and high fives… The whole realness kind of came full circle in that moment. So only recently did they really get to see like what dad does. And we essentially create a digital artifact called an mp3, and we deliver it across the internet. And then people listen to that. That’s ephemeral, really. There’s no physicality to that, aside from maybe a T-shirt, or a sticker, or the banner… They don’t see it.

It’s like, now they get why you’re locked in a room for an hour or two, and what this really is… 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. We grew up in Brazil, without a lot of money, and my parents used to sell superhero costumes. So imagine, as a kid, I absolutely loved it. And basically, the way it worked was I would see them just producing everything, 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 we wouldn’t have money during that week, and things were very tight… Other times it was sunny, and we would sell a lot, to a lot of kids, because a new Spiderman movie came out, and so on… And for me, it was clear. I could see them working with their hands during the week, and then over the weekend talking to people and selling… And I feel like for us it’s so hard - we’re just locked in a room… 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. Yup.

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”, 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, 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. 5, 6, 7 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 for disconnecting for a moment, where you just don’t walk through the living room and just like put your blinders on and ignore. No, you probably stop for a moment. I get a snuggle anytime I can get my kids; every moment I have my kids is priceless. Absolutely priceless. I just love hugging my kids. They’re amazing. And so I call those times my micro moments. And if I was away from the home, working somewhere else, I couldn’t enjoy those micro touches, those micro noon things, or having lunch with them when they’re home.

[00:16:23.13] 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… But you kind of get the point, right? Like, that’s the blessing, is the real – I guess really the advice 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 into meetings. Like, I would be in a meeting with – I can recall before having meetings with like Sentry, 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…

Hey, this is my life, right? 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. If he came in right now, I’d be like “Bud, you know you can’t come in now. Like, now’s not the best time ever.” But we also do edit, so I could edit it out.

I just would say “When she knocks, answer.” Let the office be somewhere that she is welcome. You know, 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”, whether you’re working with hardware, or working with software… “Just be curious and ask me questions.” That would be my advice to you.

I love that. I feel like whenever a meeting ends, three or four minutes and I have the next meeting, and I’m like “Oh, this is perfect. Let me go downstairs, let me play around with her a little bit.” Or whenever I’m working, I hear them screaming, and talking, and laughing, I’m like “I’ve gotta 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 “Oh, are you really sure that you’re going to do a remote company? 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 “Hey, you’ve gotta leave your family – you’re not going to have those micro moments because of this thing that we’re building.” It just feels so unfair. I don’t have a face to make that ask.

Absolutely.

Even though everybody on the team, they don’t have kids yet. But I still believe those micro moments are important with your loved ones, and whoever is in your life, right?

Yeah. They’re only young once. That moment… I look back, because my iPhone is great. I put that little picture widget on my phone for a reason… And I think that is like the one piece of magic that Apple has developed, in my opinion, for iPhone users. Now, I don’t know if you’re an iPhone user; I think you might be, because you’re a fan of DX and UX, and I imagine that you might be… I would encourage you, if you don’t have that widget in place yet, put it in place, because every single day I’m reminded of past moments, 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. The memories is what stays, and the relationships 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 as the immediate family, the people you love as who you serve in your business… 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 Cybertruck you pre-ordered and you finally got, or whatever… 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. To me, that’s the true measure of a person.

Yeah. And there’s something so beautiful about doing some kind of work that in the end inspires other people to be a better version of themselves, too. You’re leaving a different kind of legacy. Every single episode that you show up and you invite a guest, and then whoever’s listening is like “Oh wow, this is so inspiring. 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. If that’s the game that anyone listening is playing, just look at your surroundings, look at the people who are in your circle… 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 objects.

Break: [00:21:27.12]

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 I think, as I mentioned before, I’ve tracked your journey, I’ve been a fan of you over the years, we’ve had you on a few times, and we’ve gotten snapshots of that journey here in this podcast, in transcript form, in audio form as well… And we’ll link those up in the show notes as part of this episode. But Resend is a thing now. I don’t recall when exactly you founded it. 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 mouths.

Okay. I guess we’re close to a year. Almost a year. I saw you met Paul Graham. That was so cool. I saw your photo with him and I’m like “How cool is that?” Backed by Y Combinator… I mean, you’re living the dream. You’ve done it, and you’re doing it… I would say 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, ended up being a CPO there before I left - all of those things also prepared me to think holistically about 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… All of those things were preparing to this moment of “You know what? I think I’ll just try to do my own thing.” And not only the good stuff that happened, too; 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 think about their deadlines well, or didn’t prepare stuff that they should have done. So all of this culminated in this idea of “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. 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.

[00:28:11.15] 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.

Yeah. On display.

Yeah. It’s like, it’s in your mirror, and you either deal with your flaw, or you keep hiding, you keep 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 acknowledged that you’re not perfect. You are full of flaws, and you’re gonna still keep making mistakes… But hey, you can get better if you do this one thing differently next time. So it’s been fascinating. It’s been a – I highly recommend anyone to one day try to build your own thing, because it just opens up 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 – what role did your citizenship/immigration process play, I suppose, in that delay, or even aid you when you got to the moment where you wanted to pursue funding? Was that a hindrance or a help? 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 like a prisoner, with like a ball on their foot…

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, and 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. And maybe I don’t want to leave.” But it unlocked, like “Okay, now I can come and go.” And then with the citizenship, it was something along the lines of “There’s absolutely nothing else. Like, no excuses anymore.” And 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 were just like “Yeah, let’s just play around with this.” And as we were building it, and we were getting more confident, we were like “Oh, we should apply, because the process of applying is so cool.” The form they have, it’s so nice; there’s so many things you learn just by filling out the whole thing. So we just applied, without any hopes that we would get.

And I remember applying back in 2020, when I build LeCheese app, and I was like “Oh, let me just apply with 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 for an interview, and I was like “Oh, wow… We might have a chance.”

It got real.

[00:32:05.24] 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. I’m supporting my parents. 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 gonna be screwed.” But just that idea was pretty wild.

So when they called us for the interview, I was like “Man, is this idea –” It was called [unintelligible 00:32:40.11] back then; not even Resend. Crazy name… Just the only domain that we found. Like, “Is this idea dependent on getting into YC 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 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 “Okay, hold on… I’m not taking your money right now. Thank you.”

Right. “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 we’re going to do this.” So instead of them having the leverage of “Oh, we’re almost like giving you a favor.” It was almost like “No, we want to partner with you 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 looking good, and presenting good, and whatnot. How did you actually prepare for the presentation? Was there slides? Was there a deck? Who was in the room? 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 –

Wow. Compression at its best.

Yeah, 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’s no 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 watching the World Cup games, with their speakers super-loud… I was like “Oh my gosh, this is like the worst environment ever.” And then I’m waiting on Zoom, and then I see like the name, Gustaf, and I was like “Oh no, this is the guy from Airbnb.” I’m like, “I can’t believe –” I was so afraid and overwhelmed, and… Yeah, it was a wild experience. Yeah.

[00:36:24.18] 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 of that. And that’s what I tried to do. And it didn’t come from a place of “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 were looking for a good domain, which then we bought Resend.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 felt like that came across when folks heard what we were 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? 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 were like “Okay, this is looking good. 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, 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 have been sent… And other times as a side project for Dracula, just sending something out on a Saturday… So I knew 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 12-13 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 gonna come out of nowhere? What’s the point?” It’s just like “Oh, hey, here’s an email solution.” We were talking to all these people, and they were always saying that the first problem is when they’re building the template. That’s when the journey starts; a designer hands you off this beautiful Figma file, and then you look at it and it’s like “Oh, I’m gonna do this with all this archaic HTML that I need to build emails. Oh, crap.”

[00:40:01.15] And then you look for solutions, and it’s all super-bad. And testing them across Gmail, and Outlook is also super-bad. Sort of 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 Resend right after.”

So I wanted to tell his story, and I’m really big into storytelling as a whole. Like, what is the journey? What is the hero’s journey here? And the hero’s journey starts with open source; it starts with first giving back. So we’re gonna 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 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 it.”

Wow.

So that was the idea. 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? What’s the sequencing? 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… The ultimate keep it simple, right? I wasn’t sure what React email – what role it played in Resend… Because I pay attention to you, but the world is big, and I can’t pay attention to every single detail… And I knew you did that first. I thought that was an itch, and you were like “Okay, now that I’ve done this, now I’ve found that there’s this whole world to explore.” I didn’t know the full sequence, like you had said, of just the ultimate plan, like “Serve out in open source, help in those ways, build a product that you can deliver, and then a SaaS around it.” That to me is just – that’s a great outline. It’s pretty awesome. I mean, it’s a really a simple execution, too. I’m gonna have to take note.

Yeah. And it comes from observation. It’s not like we were the first ones to do that. 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, and 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 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? 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 explain it?

Te try to be very simple, and that’s the tagline we have on our website. “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 would 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.

[00:44:03.22] What I’m really attached to 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 an 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 tackle the Twilios of the world down the line with SMS, push notification, other types of communication channels.

And yeah, we have a long way to go. We’re just getting started. The team is still super-small, six people, so that has been fun… And yeah, we’ve seen a lot of growth in this last year. Now we have almost 100,000 users in the platform, we have 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 100,000-ish kind of using Resend to kind of get to that value? Are they pretty active? That’s a pretty large number, like you had said, for a six-person team in 15 months to achieve. I think Y Combinator 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’re not just batting alone; you’ve got some athletes behind you, 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. One of the strategies that we had early on was we’ve 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 built this YC deal, to have like this internal place where you can post promos for companies within YC… And we got more than 120 YC companies using us now. And we want to be on that top tier of like if you’re using Stripe, you’re using Brex, you’re using PostHog, Supabase, and Resend. 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.

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, 3pm, 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. 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, like “Oh, this is interesting. It 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 on 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.”

[00:48:05.02] And the opposite is also true. 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.” 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 a great onboarding. Because otherwise - yeah, we’re not going to be remembered.

Break: [00:48:44.21]

You have gotten funding. We kind of skipped over a little bit of that, and you were kind of touching on what I think is a point that you can afford to do, 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. 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 this something that you like to even pay attention to, or are you like 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’d be super-nice. [laughter] 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 and something thousand dollars with Dracula Pro, so I was like “This is definitely a valid path. We could build Resend as a bootstrap company.” That was one option on the table.

But then looking at the other side, it’s 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, you have so much more constraints. So we were very intentional about going that route, and that’s why 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’d 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 a super-weird game. It’s so crazy. And there was a lot of interest around Resend, because we were 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 Resend.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.”

I remember something super-weird and funny… 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 like “Oh yeah, we’ve gotta have a lot of pages on the website.” [laughs]

So going for that was super-interesting, and a lot of my peers at YC, they were raising money from funds for their seed round. And we did the math, and we were like “Okay, maybe we could raise like $3 million. I think that would take us to the next step.”

[00:55:46.25] 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: Andreessen Horowitz, Sequoia… All the big ones coming after us for Resend. And we’re like “No, no, no. We’re not going to raise from funds. We’re only going to raise from angels.” And that’s when I talked to Guillermo Rauch from Vercel, which then introduced me to Dylan from Figma. And 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 Supabase… 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 were like “This is the moment where you get angel investors in”, because 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 gonna 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 to product market fit right now. And at some point, we’re going to need 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. And super-hard.

Wow. I don’t know how I missed that detail, that your seed round, your first funding was only from angels. 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? I guess, one, how did you turn down the biggest funds in the world, basically? What was your literal response, if you can TL;DR it, or somehow give an abridged 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 folks you have in your angel list that I’m personally aware of and know as well. 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 you…”? Give me all the details. What can you share?

Yeah, the thing with fundraising is that you always want to have a really like warm intro, and not just come out 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 cold-emailing folks… Even though I think I’ve sent some of those, but I would just name-drop people that I already admire 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?”, sometimes it was just like individuals. 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. [unintelligible 00:59:48.16] from Segment. He gets it. James from PostHog. He gets it.

[00:59:56.18] 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 just say yes, or no. I got many no’s too, from people that I really wanted on our side.

And 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 the 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. 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) $3 million, it was so much money. It was like “Wow, this is insane.” It’s just so much money. It 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. Sort of like “Oh, you want to invest a million? We’re only giving you 500k allocation.” “Oh, you want to invest 200k? We can only give you 100k.” And it filled out very quickly. We started the fundraising process Monday morning, and we scheduled the whole week for calls. Wednesday morning we were done. We were oversubscribed. So it all happened very fast.

So you had a dollar amount cap per angel. You’ve got an easy number… If your number on the website is accurate, it’s 28. Did you have, like “Okay, 28 slots”? Is that the circumference of all angel investors? Is that a limited number there? How did you come up with that?

Yeah, it was not like a predefined number of people. As I was talking to some of the – 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, the respect is mutual… Let’s do it.” So it’s less about the number of angels, more about how much is allocated… Which is like a Tetris game. Because as 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. Do you need money? Do you want money? When’s the right time? Do you think about that? Or are you just totally focused on product and product-market fit? Have you reached product-market fit? Where are you at with, I guess, generally a good next step?

I share the same sentiment as you describe. 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. We have 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 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 –”

[01:04:06.23] You know, every morning I wake up, I’m like “Oh, let me just check if the servers are still up.” That kind of feeling of constant stress, and constant caution, and watching out for everything that’s happening. So yeah, we’re not in a rush. Maybe it will happen next year, or end of this year. We’ll see.

I guess this would be your official A round, right? Or is that still – you’re I guess in an angel round as a seed round, right? That’s how you would categorize it. So series A is still - that’s your next step, is series A.

Some people raise seed extensions. That’s another path. I feel like the next one for us could be a series A.

Do you think the next round would have a mix of maybe reallocation to existing angels, maybe some new angels, and funds as well? What’s your thoughts on how you expand? Because what you’re offering really is you’ve got some conviction, you’ve got some awareness where you’re going, 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 gonna go here, and here is 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… Because when you’ve got 28 angels in your first seed round, realistically, it’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 as successful as you’ve ever been in the industry; I think 28 people is nowhere near your network, 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 getting people that share the same vision of the world, or share the same passion for serving developers. And that takes time. 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 grow with, and that’s extremely hard. That’s much harder than “Oh yeah, how can I get $10 million?” 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. It’s easy-hard.

Yeah. So yeah, we’ll see how it’s gonna turn out… But I think it’s what you described; it’s 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; give the board seats to a fund, and now you start building that relationship. And that’s why it’s so important to pick the right person, because now you’re gonna have that person for the next 10 years on your board.

It’s like marriage.

Yeah, right?

Possible cancer, even. Toxicity is totally an option.

Yeah.

Yeah, I’ve seen Silicon Valley, the TV show…

Exactly. [laughs]

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 satirical, obviously… And satire is obviously so close to reality.

So close. Oh, my gosh.

And in a lot of cases – 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.

[01:07:59.18] Totally. I’m watching it now again, I guess maybe the third time or something… And it’s funny how it’s still accurate. Because you know, some shows don’t get old well. This one - it does. Everything is still there. It’s crazy how it’s super up to date still.

I’ll share a small aside then, that’s tangential to this 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-hm.

So friends with Brian Cantril, of Joyent fame, and now Oxxide fame… And he’s been on the podcast before, and he’s a big fan of Silicon Valley… And we’re in DMs on Twitter/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 it’s pretty much just like trading Silicon Valley riffs of sorts, or screenshots, or whatever… And he’s like “Hey, you know that Gwart had a cameo on season one, right?” And I’m like “No…?” And then he just like didn’t talk to me for like a week. And I was like “Come on, don’t leave me hanging here… Tell me.” He’s like “Oh, I’m sorry. I didn’t tell you. I left you hanging.” And so he tells me… And in season one, episode four, there’s a Gwart cameo.

Oh, wow. I haven’t paid attention.

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 - I’ve found the actress’es website, and she seems super-approachable… And they had a contact form, so I’m like “Alright, I’m gonna reach out.”

No way…

So I reached out to confirm, one, that the cameo was true. And then after that, it wasn’t – and I forget her name; I’m so sorry. The actress who played Gwart. I only know her as 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 think that she’d be down to a pod with some super-fans of Silicon Valley?” And she responded with “Yeah, let me figure out some time.” And so the plan at some point in the near future is to have a show here on the Changelog, probably on Friends, our Friday talk show, with the Gwart actress, just riffing about Silicon Valley.

No way…! Oh, my gosh. I’m so looking forward to that. 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 Resend and just talk about Silicon Valley the whole time, but I’m not going to do that. But that’s what a fan I am. I think it’s just an absolute masterpiece. And 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 “It’s too close to reality for me”, or PTSD… Now, I really do understand the literal circumstance of PTSD. I think in the case that these people say PTSD, it’s not truly PTSD. So I don’t give them that credit. They’re missing out…! They’re missing out absolutely on a masterpiece of a show. A masterpiece.

Yup, for sure.

And you could probably attest to this, because you’re like – like, Richard Hendricks was looking for a series A, and finally got it… I think it’s in season two. And season one, season two… You’re just past TechCrunch Disrupt, which was really YC for you… And now you’re in season two, potentially gonna 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 the toxicity in the board is elucidated very well in this whole entire show. And I think it’s in a way a to do and what not to do in literally Silicon Valley, or just in the software industry, which tends to like revolve around California and SF. Your philosophy page says “Not everybody lives in SF or New York”, or all these other cities in the world - and we’ll get into that as well - but it very much revolves around the Silicon Valley way. Right?

[01:12:06.16] Yeah. Man, watching that show as a regular developer at first, then watching now as a Silicon Valley founder…

Way different, right?

…like, living in SF… It’s just so – it’s extremely close to reality. I’m understanding some jokes that I’m sure I couldn’t understand the meaning at first.

Like nagging?

Yeah. [laughter]

What 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 Googly Bots or something like that, or Giggly Bots, or whatever, was the company name… He took too much money, had a down round…

Yes. Season two, right?

…got exited as a CEO… That’s a total reality, right?

Yup. 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, 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 capitalists to work with, or the wrong fund to work with. That’s totally a possibility. 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, or funding a company and taking it over.

For sure. It’s just crazy. Imagine taking your baby from wow. You spent so much time building that thing…

“How dare you”, right?

Yeah. It’s so wild.

I mean, I don’t want to call it predatory, because I don’t want to blanket it that way, but that kind of action, if premeditated, is totally predatory. If you purposefully overvalue, overfund based on a valuation, 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 gonna have a down round, and you know that’s a possibility, and you do that on purpose, then that’s totally predatory.

That’s evil, man. That’s plain evil.

It’s pure evil. It’s the ultimate version of evil.

Yeah. [laughs]

So you’re in season two, basically, with Resend.

Yes. [laughs]

Season two with Resend.

Yup… Hopefully, I don’t get taken out.

Do you have an Ehrlich in your life?

Oh, man… So we joke that my wife is Erlich.

Is that right?

Yeah. we joke about that, because she makes some jokes that is like totally Erlich.

Do you have a Richard then?

I don’t think so… Maybe my co-founder… I don’t know.

Do you have a Gilfoyle? Gilfoyle is my favorite character. I absolutely love Gilfoyle. I mean, the best – I mean, I really love them all, but if I’m ranking them, I’m thinking… There’s times I like Richard way more than everybody too. There’s times I like Donald, really, but Jared is his name… His real name is Donald though, you know… There’s times that Jared is the best character… They ebb and flow, but I think they all are a stellar cast, and a stellar set of characters. But Gilfoyle, really, he brings – he brings it. He brings it so good.

Let’s go back to Resend. Okay, so we’re in season two, technically… This year, maybe next year, funding… I’ve gotta 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 not too challenging to have good – I mean, I guess [unintelligible 01:15:51.00] It’s not too challenging to build out a network that wants to believe in you, and give you an opportunity, like you have done with your angels.

[01:16:00.21] I imagine email generally is 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? I’ve known you to be more on the frontend, 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 backend area, where 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 I think the UX side seems to be pretty easy for you, because you’ve got skills on the frontend, you’ve got taste, you’ve got – beauty has always been part of the things that I think you’ve produced, that I’ve seen… But the challenge seems to be the real hard stuff: the deliverability of email, 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 still on season two, I probably wouldn’t have done this. It’s so hard, man. It’s so hard. 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.

I was like “How does this even exist?” And it turns out when you go there – there’s all these folks from Yahoo mail, and Outlook, and Gmail… All the people who were actually building that kind of infrastructure, and they’re all talking about “How can we prevent abuse, phishing emails, spam, at scale?” And we see those problems every single day. 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 “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 gonna go through 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 exists, because there’s so much abuse, there’s so much difficulty in making sure that the emails are gonna land on the primary inbox, and not on the Spam folder, or the promotional tab… But I feel like you kind of need that naiveté; 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.” You’ve 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? Are you pretty good at email delivery? I mean, you can’t just be pretty good. You have to be really good to be considered enterprise or worthy of even taking a dollar.

Yup. And there’s definitely different expectations. 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’ve got to fix it?

[01:20:15.18] I’m very lucky that we have a lot of great people on the team, that know a lot about all that… We have folks like Bu, my co-founder, who is – man, the best engineer I’ve ever worked with. He’s so good. He’s so fast, he can build stuff that – yeah, 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’ve got to make trade-offs all the time. 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 gonna 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 have found is no, you’re still aiming for both of 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 gonna 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 frontend, that’s on the backend, that’s on the infrastructure level… Always thinking about that minimum version that is at both levels. We call this v0 all the time. We’re like “Oh, how can we ship the v0 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 going to ship crap. So how do you do that? In 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 [unintelligible 01:22:10.28]

So when you think about the team you’ve had to build then - like, you’ve got ops, you’ve got uptime, you’ve got SREs… This is like a whole new world. How do you build out your infrastructure? 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 before WorkOS I was at a company called Liferay. And this company would sell this on-prem software to big companies. So think of like the McDonalds of the world, Pizza Hut… These really big companies. And that product - 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 this how this portal was built… So I had this opportunity of like me and a co-worker to start this Liferay Cloud division, which was at first just like an experiment of “Oh, how can we put Liferay in the cloud, and maybe build our own PaaS?” So we kind of built our own Heroku, or Railway, or Render inside the company for this product… Which then became like a whole thing. We had to actually start a whole separate division, and we grew the team from just me and my co-worker to like 70 people.

[01:23:45.20] And then we went from 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 how you deal with these types of people.” It’s a different skill. I’ve met DevOps engineers that don’t even know how to write a single line of code, but they’re extremely good with shell scripts, and they know how to scale these Kubernetes clusters like no one else can.

So I feel like that experience equipped me to do Resend later… So that now that we are facing all these scaling challenges, at least I have a framework to go about it. We still don’t have Kubernetes, we still don’t have like all this infrastructure 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. 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’re 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, 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 [unintelligible 01:25:59.09] I think you lead a lot with story, like you mentioned before, earlier in the podcast, but what is next? What’s a big next thing for you not many people know about, that you can share on this show?

In a way, I am 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. Uptime is crucial. Because frankly, we did have a downtime in January, and then another one in February… And our uptime is not looking great. So we’ve 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. 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 this issue, I talked to their support team, and then they fix it in like one minute. They gave me this tip, and they gave me a hoodie in the end, and I’m like “Wow, this is so incredible. 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 again, that’s what we signed up for.

What about you then personally? What do you focus on on the daily? In a month from now, what is your focus?

[01:27:53.12] 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 when talking to enterprise customers; there’s a lot of things that – yeah, I never had to sell a big contract. So now I get to learn how to do that.

There was this one candidate that we were interviewing this week - last week, actually - and he told us “Oh, I have this other offer.” And he was super-interested in us, we were super-interested in 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 startup, we should be having that competitive advantage, or delegate it 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 all have gaps. 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… Self-awareness. It begins there.

That’s the key, man.

Well, it’s always good to catch up with you. Big fan, obviously. Big fan of Resend, big fan of you, and I 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 – 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, 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; somehow we got super-deep those three times, and I really appreciate you and 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 “Oh, how can we get more awareness? Oh, let’s sponsor the Changelog.” Whenever we ask the engineers “Hey, engineering team, 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? 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 “Ah… 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. Jerod and I come every single day, and we show up and we do what needs done… And I feel like that’s really what you’ve gotta do. You’ve gotta love what you do, you’ve gotta love the people you’re doing it for… But it is hard work, but it’s also very, very rewarding. Like all hard work, it is rewarding. But I do appreciate 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 literally hang together, or just like make time to do it. It’s not easy.

For sure. We’ve got to do that. Thanks again, Adam.

Very cool. Thank you for coming on, I appreciate you.