IndieHackers Podcast: Pivoting from Hard Times to a Viable Product

Listen to this exclusive deep dive into the development of the Nylas APIs with Nylas CTO Christine Spang.

Pivoting from Hard Times to a Viable Product - IndieHackers Podcast - Nylas

Courtland Allen of Indiehackers recently sat down with Nylas CTO Christine Spang as she shared more about Nylas’s journey of reorganization and growth, and the challenging decisions she had to make along the way. You can listen to the full podcast here and follow along with the transcript below.

After her co-founder left the company, Christine Spang found herself in a difficult position: deciding what to do with a product that wasn’t selling as much as she’d hoped, juggling several different projects competing for her team’s time, and rebuilding the team’s morale to get the company moving again while fostering a great culture. Learn how she overcame the odds to turn the Nylas APIS  into a thriving company that handles over 100 million API requests per day.


Courtland Allen: What’s up, everyone? This is Courtland from and you’re listening to the Indie Hackers podcast. On this show I talk to the founders of profitable Internet businesses and I try to get a sense of what it’s like to be in their shoes .How did they get to where they are today? How do they make decisions, both at their companies and in their personal lives? And what exactly makes their businesses tick?

Today I’m talking to Christine Spang: the co-founder and CTO of a very cool company called Nylas. Christine, welcome to the show and thanks for joining me.

Christine Spang: Hey Courtland. Thanks so much for inviting me to be in the show.

I’ve heard about Indie IndieHackers for a long time. So it’s a real honor to actually be on the show.

Courtland Allen: I’ve heard about Nylas for a long time and I was actually a user of your desktop based email application back in the day.

Christine Spang: Oh wow, super cool.

Courtland Allen: Yeah, so can you explain to us what Nylas is and how it works?

Christine Spang: Yeah, so the basic gist of Nylas is that email has been around for a really long time and it’s essentially the lingua franca of business. When people are talking between different organizations, they’re communicating, they’re organizing collaboration, meetings, sharing  documents. All sorts of things like that.They do it through email. And yet because emails been around for so long. It’s been around for about 50 years longer than the the web itself.It’s become really hard to develop with overtime. It’s a global distributed system that has many different client server implementations. And while there are open protocols for working with email because there’s so many different implementations, there is a lot of edge cases and complexity that you have to deal with.

So we built Nylas in order to drastically simplify the experience of developing software that works with email.So the basic product is a modern rest API that allows you to connect to any email mailbox as well as anyone’s calendar and address book all through one really simple API. So if you’ve used APIs like Stripe or Twilio, it’s like that but for email.

Courtland Allen: Okay. So for the non developers in the audience, it’s very difficult for a developer to build an app that includes email integration or calendar integration because it’s just too complex.

What Christine has been working on at Nylas for the last few years is building an API than any programmer can plug into and that allows them to easily build an app that includes email or calendar or contact integration.

Christine Spang: What we’ve seen in the software market trends in the last few years is more and more folks building business productivity tools that allow you to be better at some job. But also you need to pull communication and collaboration information and the data for that is in email. So all these folks need to be able to integrate with email we make that really easy.

Courtland Allen: I wish you had existed eight or nine years ago when I first started making apps online because the very first three things that I made were all intimately connected with email.I made I think the very first app I ever coded was an app that you checked your Gmail inside of Facebook and then after that it was an app that you create advanced filters for Gmail. You could say if I get an email with this many attachments or this many recipients, I want you to delay it until this time of day or something that.Then I made an app that let you turn your emails into tasks and check them off. Every single one of them I had to integrate with email and there was no API like Nylas. So I had to go do all the heavy stuff myself and it was a good learning experience, but it was extremely frustrating.

So I understand why a company yours can exist, but let me ask you right off the bat, emails are notoriously difficult to work with as a programmer. Then on the sales side of things I think most people think of email as being free. So you’ve got this dual challenge of starting a company where it’s really hard to build what your building and also the people in your market aren’t exactly used to paying for stuff.

Why do this to yourself? Why start an email company?

Christine Spang: Yeah funny story. So in the beginning actually the product vision for Nylas was to eventually create an email client for power users. The infrastructure side actually fell out of this initial product vision of building an email client, but we actually did realize that it was going to be difficult to build an email client. Which is actually why we started out with this data abstraction layer.

So the advice we got was you need 10 engineers for a year just to build the basic version. We were like “well, we don’t have 10 engineers or a year, so maybe we won’t do that.” So we took a step back and asked “ what’s a stepping stone that could help us get there that might also be useful to other people?”

That’s how we ended up building this essentially middleware layer API that abstracts away all the complexity of dealing with mail providers and I can talk a little bit more about this. You mentioned earlier that you were a user of N1 or Nylas Mail which actually is the email client that we built. This email client was originally built backed by the data APIs that we sell today.

We started building the data APIs, and launched those as an open source repo. This was an interesting thing that we did to get the word out in the beginning. We knew that we were going to have to get developers excited about what we’re doing because we were essentially saying hey, here’s a new way to develop with email and trust us to be a good service provider for you.

So first, we released the basic APIs and open source repo on GitHub and did a bunch of press around that. Then we turned that into a SaaS service. Which is actually the same service that we run today. So we first launched that in fall of 2014, I believe. So it’s been a few years at this point. Pretty soon after we had launched this SaaS APi we started working on this email client that was based off the API and probably spent two years total working on that.Learned a lot and I would say this ties back to what you were talking about in terms of it being a challenge to monetize email and that the email client was a pretty challenging business model to figure out where we had these developer APIs and we had the email client.

We very easily got a lot of people to download and try out the email client but because people expect email clients to be free no one really wanted to pay for just the base email client. So we were building plug-in packages into the email client to make the email client have really tight Integrations with other products. That was our long-term plan for being able to monetize that email client. As you can imagine building three major products as a tiny startup is incredibly difficult.

We just saw a lot of churn on the email client, people would try it and then they were early adopters who would go on to the next big thing afterwards. People who didn’t want to pay for the base email client and it was a real struggle for us to also build products on top of  that, that we could sell for more money.

Courtland Allen: Yeah, I bet. So what did you guys do after you decided to pivot away from the email client?

Christine Spang: Yeah, so we basically went back to our roots. All of that time when we were working on the email client we were still developing and selling the email data infrastructure APIs. We had a few companies come on board in the early days that started out super small and had been growing all of that whole time. So we essentially took a look at the business metrics of are two different products for the data APIs and the email client and found that the business metrics for the email client or really bad. We had lots of people download it try it and then churn within like two months was 90% or something that. Which is really hard to turn into any sort of sustainable business because your customers trend down towards zero over time. We just would have to spend infinite money in marketing. But at the same time looking at the metrics for our data infrastructure APIs, it was the opposite story actually.

We found that when people started using the APIs they would start out small and their usage would grow over time. So they would connect more mailboxes to their applications. They would get users and we would then be powering those users as well. So it’s almost the opposite situation where we found that that product is really sticky. People would build the APIs into their product to power their email features and their usage would increase over time. So the way that we charge for the APIs is essentially per connected mailbox. So any email address that is connected to an application through Nylas, we bill the developer of the application for that mailbox.

Just looking at the metrics for that API, that started out super small, but it’s very steadily growing and the growth metrics that we were seeing there were really really promising. So essentially what it came down to was we decided to shut down development on the mail client. We essentially spun it off as its own open source project and one of the original developers on that mail client still maintains it. There’s a fork called Nylas mail which if you want to continue to use Nylas mail you can use the fork because we’re not developing Nylas mail anymore. So we spun that off and completely stopped developing it and refocused completely on the data APIs which just made much more sense as a business. That transition was complete about a year and a half ago, I would say.

Courtland Allen: How are things going nowadays? Can you share any numbers around the amount of revenue you’re generating or the number of customers you have or the size of company?

Christine Spang: Yeah, for sure. So just two things, we’ve now been around for about five years. The team’s about 35 people and a lot of that growth has been recently. So I would say that about a year ago we were about 15 people and now we’re 35. So it’s quite a lot more. We are making millions of dollars in revenue each year. I won’t get into exact specifics there but we have about 200 paying customers that are using the platform. So those are all other businesses that are using us to power different features in their applications or internal tools, there’s all sorts of different use cases. Not just people building other pieces of software, any time you want to access any of the data or to automate things in email the Nylas APIs are a good fit for that.

Courtland Allen: Nice. Congratulations on all of that. That’s got to feel, I imagine, really good to be in a position where you’re generating millions of revenue.

You probably feel very secure. Where not too long ago the mail client you’re working on wasn’t really working out the way that you planned. Did you imagine at that point in time that things could have taken a turn they have?

Christine Spang: That’s a good question. It was definitely pretty rocky for a while there, where we weren’t really sure what the future of the business was going to be but I’m kind of the person who takes things one week at a time.

I don’t give up until it’s obviously totally not working and because we never reached a point where there was no way forward. It just worked out but it does feel good. I would say that there are almost more challenges over time as you grow a company because there’s just so many more moving parts and complexity.

Now we have an entire sales and marketing department which in the early days of the company it was all engineers. So that’s been a new thing that’s been really interesting and also it’s tricky in terms of your culture will change over time as you add different sorts of people and have to figure out how to work well together. At this point, I’m basically a full-time manager.

I rarely write code on our product anymore and I think that’s a really healthy thing. If you start a company and you expect to grow it, you should want to learn the skills of management and want to get good at them because that’s the way to have the most leverage as a founder of a company, once it’s beyond 20 people.

Courtland AllenThat’s a tough lesson to learn especially as a developer used to all the productivity coming out of yourself, right? If something’s going to get done, you sit down and you do it. It can be hard for a lot of first-time founders or developers to realize the power that lies in delegating and having other people who you trust to get things done and how much more effective you can be if you let them do those things and you work with them.

Christine Spang: Yeah, for sure. I feel before a year ago it was still at a point where I could do some things myself and that was fine, but doubling the company in the past year it’s completely changed.

Also in a good way and that we hired a bunch more engineers and now I actually don’t feel like I need to hold up the product and the system.

There are a lot of really smart, competent people that I’m working with who are honestly better at many of the things that I used to do. So, it’s really exciting to see.

Courtland Allen: Let’s go back to the early days where you were doing a lot of coding.

Christine Spang: Yeah.

Courtland Allen: Or even before then, how did you first learn to code?

Because a lot of people listening in want to start companies and they’re in a position where they don’t know how to code and they’re wondering if they should learn how they can best learn.

What’s the story behind how you got into programming?

Christine Spang: Yeah, totally. So the basic gist of it is that in high school, I well even before high school, I started out being into computer games. All sorts of different computer games from Warcraft and Starcraft and Privateer and all these kinds of things. Essentially I was trying to find games that could let me escape into other worlds and eventually this led me to this online game called MUDs or multi-user dungeons. I don’t know if you’ve heard of them.

Courtland Allen: I have.

Christine Spang: They’re basically space games that you play across the Internet and so in high school, I started playing this Lord of the Rings themed MUD called Shadows of Isildur and I have this habit of ending up in charge of things. Just through force of curiosity, I guess. So I got really into this game I played a lot. Eventually the people who ran it were like, hey help us run the game. So I started helping run it, building areas of the world using the in-game tools. Running storylines and plots because it was a very role-playing intensive game and eventually I wanted to be able to do things in that role that involved changing the game mechanics itself. So basically I had to learn to code.

The game engine was written in C and I don’t really recommend C as a first language, but I essentially started teaching myself C in high school in order to work on this game engine. And the game engine also only ran on Linux. So I had to get my brother to help me install Linux on my computer and somehow we managed to not brick our Windows installation while doing that. It was really, it was before the days when the partition editor in the Linux installer was completely foolproof. So if you pressed the wrong button you could wipe your whole hard drive. It was super scary.

Courtland Allen: Sounds you really wanted to make changes to this game and you’re willing to jump through hoops, learn how to code and risk breaking your entire computer to do. Which I think is great because a lot of people it’s difficult to learn how to code there’s lots of frustrating periods where you ask yourself why am I even doing this? And if you don’t have that sort of drive, this thing you want to work on to learn then it’s easy to just give up.

Christine Spang: Yeah totally but it’s funny, through this experience of wanting to contribute to this game I got introduced to the free and open source software community surrounding Linux. So the distribution that I installed in high school was this distribution called Debian which is a really popular Linux distro that’s also the foundation of many other Linux distros. Through that I learned about open source and the free software, where it came from and that ultimately led me to want to go to MIT. So I had heard for software, go to MIT, this sounds really awesome. I want to go there. So that’s essentially how I ended up going to MIT is because I started teaching myself to program and then discovered free software.

Courtland Allen: So let me ask when did you start learning about entrepreneurship and startups and running a business because that’s something that is very tangential to learning how to code? Most people I’ve talked to who ended up starting a start-up have spent some time reading about it and dreaming about it before they got started. What’s the story there for you?

Christine Spang: I consider myself to be a bit of an accidental entrepreneur. So I basically ended up in startups through free and open source software.When I was in college, I essentially got all of my college internships through my connections in the open source software communities. Including my first job out of college, which was this startup called Ksplice which was started by a few people that I knew from Computing Club. Or the Student Information Processing Board, which was the full name of this club because it had been around for so long that they called computing, information processing back in the day. I joined this startup that was started by some friends of mine and that was my first experience with any sort of entrepreneurship. It was a really interesting super cool company in that it was totally bootstrapped. So they never raised any money for Ksplice other than they won the MIT $100k entrepreneurship competition which was one way they got some initial funding for the company and then also we got some small business research grants from the government. Other than that Ksplice was a totally bootstrapped company that built itself up through revenue. I was there for basically a year-and-a-half including the few months that I spent working there as a senior at MIT. Then the founders sold that company to Oracle. So I got to see the whole arc of a lifetime of a startup in one iteration through Ksplice. I would say that’s my first experience with entrepreneurship.

Courtland Allen: Did that inspire you to start your own company after that? Or did you feel that oh, that was a cool experience, but I still want to keep on the path as the developer and maybe go into the industry.

Christine Spang: Honestly, I never really thought of myself as a founder. I had a friend also from MIT who I remember having a conversation with about what I was going to do after Ksplice. He was like, do you think you’ll start something or join something?

I was like, I don’t know. I’ll probably join something. He was like, yeah, starting something is stressful. Which is pretty funny looking back in hindsight because I would agree that certain something is stressful but here’s what happened. So basically at Ksplice the founder sold the company to Oracle. I stayed at Oracle for basically the two years of my retention and six months before my retention was up at Oracle I was trying to think of what I was going to do next because honestly I was super bored. I felt if I stayed at Oracle for a few years, it was a pretty cushy job, but I didn’t feel I was learning that much and it just seemed a place where I could stagnate and get left behind. So I was trying to figure out what I was going to do next and it was also a time of my life where I had stayed living in Boston for a couple of years after school, working at Ksplice but I didn’t necessarily want to stay in Boston forever. In that past three years a bunch of friends of mine had moved away and I felt it was a good chance for me to try living somewhere else because I would have to rebuild my community in Boston if I was going to stay there.

So I wanted to check out the Bay Area and I had a friend of mine from college, this guy Michael Greenwich, who had this email idea he’d been kicking around for a while because he’d been trying to build some stuff with email as his undergraduate thesis at MIT and it was really hard. So we were pretty good friends in college, and I’d been talking to him about that. But I was also talking to companies about potentially just getting a job. So essentially I took a week off from work in April of 2013 and I flew out to San Francisco and I interviewed with two companies, Stripe and Meteor. This was actually the first time I had ever done a technical interview, anywhere, anytime because I’d gotten all my jobs through connections previously. So needless to say, I think I was pretty bad at interviewing at the time and I didn’t get an offer from either company. So I basically was just like, what the heck, might as well just start the company with my friend. It didn’t feel super risky at the time given that I was like, well, I want to move across the country. That’s a big change and I was 24 and didn’t really have a lot of possessions or responsibilities. I think the most expensive things. I owned at the time were a laptop and two bicycles.

Courtland Allen: Did you guys have any funding or were you living off your savings?

Christine Spang: So in the beginning we were just living off of savings. So my co-founder Michael had been consulting for a while and just doing part-time contract work and essentially I moved across the country, did it super cheap. I shipped books via Media Mail, which is the super cheap way to send books across the country. Also I have three siblings and in college I lived in a big 30-person co-op, so I had a lot of experience with living with a lot of other people and just keeping my expenses really low.So I just moved in with a bunch of roommates in Oakland and I was living off of savings for the first three or four months. Which wasn’t that difficult just because I wasn’t spending a lot of money on much.

Courtland Allen: So if you think back to those days, you move in with all these roommates. You and your co-founder are going to start this company, somewhat out of necessity because you didn’t get any job offers. What was your overall goal here? What was sort of your best case scenario for what could happen?

Christine Spang: Yeah, I mean honestly at the time I approached it with the attitude of, this is a fun experiment and no matter what happens it’ll be an interesting story to look back on later in life. I didn’t really expect it to be still around to be honest. I didn’t really have a dream of the future but I was excited about building an organization from scratch this was something that was really fun that I wouldn’t really get a chance to do somewhere else. To have a place that I could imbue with the culture that I wanted. Essentially create a place that is a place that I would want to work and hopefully also make something in the meantime that helps people build stuff that they wouldn’t be able to make before. It seems a good way to make a mark on the world that you wouldn’t be able to do at a company. So it’s how I was thinking about it.

Courtland Allen: Yeah, it makes perfect sense that after your job at Oracle where you were super bored that you would prioritize creating a company that would actually be fun for you to work at and where others would enjoy working as well. What was it like in the early days of Nylas when you first got the company off the ground? And how did you make decisions as to what to prioritize working on first?

Christine Spang: So for the first three or four months or so essentially we were mostly prototyping things and iterating on the idea because it’s hard to get people to give you money if you can’t really even describe to them what your goal is. So the early days were a lot of conversations around what the long-term goal was and how to communicate that to people.How to communicate the problem and talking to lots of people that were potentially having that problem, to help the ideation phase and also starting to write some  code to see what an initial product would look like. So my background is all back-end systems engineering so I started out by writing our initial IMAP sync engine. So it was three or four months of working out of my co-founders apartment and every single cafe in the mission.I can tell you which is the best cafe to work out of, or at least it was five years ago.

Courtland Allen: Yeah, which one?

Christine SpangIt’s Haus Coffee at 24th and Folsom, that place’s the shit.

Courtland AllenAll right. I’m going to write that down.

Christine Spang: Yeah, it’s house the German way, haus. And they’re really great because one everybody else there is working. Two it’s pretty quiet and they just play chill electronic music in the background and three there’s power and Wi-Fi.

I felt I learned a lot about about working out of coffee shops. And that is super annoying to have to find a seat and deal with bad wifi and buy a coffee every three hours. So I was really glad when we stopped having to do that.

Courtland Allen: So, how did you guys get out of this phase where you’re scrimping at coffee shops and you guys are burning through your savings and trying to get the product out the door, to the point where you reached some first stepping stone of stability?

Christine SpangIt turns out it’s really hard to hire people if you don’t have any money, so we started talking to various seed investors and I would say that basically in December of 2013, we raised a million dollars or something that. The way that we did that was through our network essentially. So my co-founder had run this entrepreneurship event at MIT so had gotten connected to various people in the startup community that way and just by asking around. One of the great things about Silicon Valley is that there is this large community people that’s willing to take a bet on a team, even if the idea is in its early stages, give you some money to work on a problem. I think that’s something that’s really unique about this area. That’s pretty great. So we essentially had this early formation of an idea and the pitch that we’re giving people was, it’s really hard to develop with email. We want to make email better. So a bunch of folks gave us some money and we got this tiny little studio office in the mission which had no windows, but it did have a skylight which made it not quite a cave but essentially we managed to fit six desks and an Ikea couch in there and it was just the place where you would go to crank out code every day.

Courtland Allen: So you’ve got some funding, you’ve got an office you’re no longer having to buy coffees every 3 hours at coffee shops. What did you do to get your first few users in the door?

Christine Spang: Yeah, I alluded to this a little bit before with really focusing on open-source and generating developer interest that way. So we hired our first couple employees in January and February of 2014 so essentially we raise this money and then basically used our network to find other people with few responsibilities who could live cheaply. We paid ourselves all a flat $75,000 a year plus equity in the company and we got this really cheap office and spent six months writing the first version of our API and our IMAP sync code and released that in summer of 2014 as this open source repo on GitHub, which was super scary. I remember flipping the bit on the GitHub repo that made it public and worrying that I don’t know hordes of Internet trolls were going to show up the next day and tell us our code was terrible.

Courtland Allen: Which happens sometimes.

Christine Spang: It does but it turns out that most of the time if you don’t go and actively tell other people about the thing that you’re working on just no one even will find it or notice.

Courtland Allen: Is that what happened to you?

Christine Spang: Yeah kind of. I mean we flipped it, we made the repo public in January of 2014 and essentially no one found it until we did a press push and we were like, hey, we are working on the future of email and here’s what it looks like. We got an article in TechCrunch, talked to a bunch of reporters and we essentially needed to get attention.There’s no way this thing was going to work if we didn’t manage to talk to other developers who are having the same problem and make sure that what we were working on would solve their problem and get initial customers. So I think it’s a really key part of how we got the company off the ground.

Courtland Allen: I’m curious about how your mindset has changed, if at all, since those early days. Are there any things that you believed back then when you first started Nylas that you don’t believe anymore?

Christine Spang: Yeah. I really thought in the early days that we could reinvent all parts of corporate America from scratch and I definitely don’t agree with that anymore. It turns out a lot of best practices that exist with running companies are there for a reason. Everything seems super simple and you don’t need to have structures when there’s 6 people in a room. Even going from 6 people to 35, communication gets a lot harder and there’s all sorts of things that you need to do to get everyone aligned and rowing in the same direction. In the early days I could literally go to work whenever I wanted. We weren’t having to have any meetings. I could work on Saturday. I could not work on Tuesday and nothing would really change because it’s just following your own rhythms but as you add more people to group. You have to get more disciplined about when you’re working and when you’re available.You can’t just follow your whims as to what you want to be doing. So I thought we could just reinvent everything but now I really feel you should pick a couple of things that you want to change about your company and just do everything else by the book.

Courtland Allen: Were you ever tempted to just stay small? Sell your API that you’d built, keep the company lean. Maybe not raise any more money and then continue being able to take Tuesday off and not have to worry about meetings and do all that good stuff?

Christine Spang: Hmm, honestly, not really. Just because just building that technology for this product has been very challenging and I really want to go to hire more people to work on it because having more people makes it better. So I think if I’d wanted to do that I should have picked a different problem domain and this is the business where you can make a whole area really better for everyone but it’s going to take a lot of work and you’re going to have to build a significant organization to do it. So I should have signed up for a different problem if I wanted to keep it small but I think it’s really exciting to build a bigger business and I think there’s pros and cons of raising venture funding but there’s a lot of things that it unlocks that are really exciting.

Courtland Allen: Yeah, that’s really something to think about how the product you decide to build and the business you decide to create really influences whether or not you need to raise venture funding. How did you guys transition from deciding you wanted to do this API to building Nylas N1 your email client.

Christine Spang: I mean it’s a bit tricky. Essentially in the first year our employees one and two were both back end engineers and then we actually met this awesome guy in a coffee shop. His name is Ben Gotow and his background was in building iOS applications and we brought him on pretty shortly after and he essentially was building various different front-end applications as we were building the API in order to make sure that the API design was good. So essentially he started building the email client as soon as we had the API in a pretty good place. We developed two teams over time where we had the smaller team that was building the core of the email client and the majority of folks working on the back-end infrastructure.Eventually the the client team got bigger. We were essentially working on both at the same time but the mail client started out as a very small experiment with two people working on it.

Courtland Allen: That’s such a difficult place to be in where you guys have really these two  projects operating side by side. One of them is beginning to grow pretty fast and the other one is the one that you started off with. How was that for you? Was it stressful trying to decide how to prioritize and split your time between these two projects?

Christine Spang: Yeah, for sure. It was super challenging and honestly, looking back at it, I almost would consider it to be a strategic mistake to try to do both of those things at the same time. In that the email client, we considered it to be the future of the company at the time. So it was the exciting shiny thing to work on and yet the back end had to be rock solid and scalable in order to enable that to happen. So there was definitely some weird cultural things around it’s exciting to work on versus not. Also especially as we were starting to scale up, the back-end team being really overworked. So as I mentioned earlier infrastructure and back-end stuff is always been my interest and what gets me excited. So I wasn’t that unhappy to have the email client not work out and it’s been really really helpful for us as a company to be super focused on one product. And if I were to start another company, I would never try this again, to have two major products that were both pretty complex and to try to resource them with a really small team.

Courtland AllenYeah, I bet it’s one of the most common things you hear people tell founders is to focus because in any company, the number of things that are tempting to build is always growing. Every time you build anything it enables you to build a bunch of other things and it’s really hard to say no to those things and it’s hard to prioritize. What was it like to transition out of building the email client and back into focusing on the API full-time?

Christine Spang: Yeah. Totally.

Courtland Allen: That’s a hard decision to make as well.

Christine Spang: Yeah. I mean part of the reason to do a start-up is to think big and dream big and one reason that people do it when they’re young is because you don’t know what’s not possible. So when we were building these multiple products, we thought it might be possible and it turned out to be completely crazy, but I would say that we probably hung onto the email client for a bit too long in terms of not deciding that it was a bad business. We did a bunch of iterations on things to try to make it work. We actually ported our email sync engine to JavaScript to ship it in the front end. So that the email client wouldn’t have to be storing tons of data on our back end which is really expensive. So about 15 months ago my co-founder left the company and this is also the time that we stopped working on the email client. The mail client was really always Michael’s vision and I think that was definitely a factor in how things shook out there and that it wasn’t working out.

Courtland AllenThat’s a lot of change to handle, not only dealing with shutting down this product that’s absorbing your entire company, but not doing very well, but also losing your co-founder. How did you deal with that?

Christine Spang: It was really stressful and honestly the relationship I don’t think was great for me or him for a while before that for various reasons. I mean, essentially what happened was my co-founder left and then the whole company really came together. We talked about what was going to happen next and folks thought that I could be CEO or we had basically our first business development hire this guy Gleb Polyakov who had been with the company for about two years at that time.We had hired him after raising a series A in 2015. And I also thought that Gleb could do a good job as a CEO and basically what we did was Gleb and I sat down and had a conversation and I really wanted to stay focused on technology. I also thought that Gleb’s skill set just would allow him to ramp up much more quickly to be a really effective CEO and what I really wanted was for us to make a decision that was going to be the best thing for the company. So we decided to make Gleb CEO and I think that’s actually worked out really well for us, but it was pretty transformative for me to go through this experience of all of us to come together and to have the team really back me. That really helped with my confidence level and for us to just figure out something that was super difficult. Most companies don’t really make it through a transition like this and I think it’s something that’s really unique about our team that folks really trust each other. That we’re now battle hardened and we’ve reaffirmed that we want to be working together and are excited to be working together and that’s a really powerful core for an organization. So I feel really good about where we’re at right now. I think that we’re stronger than we were before and also way more focused and yeah, I’ve learned a lot about myself through the whole process. I also wouldn’t really trade the experience, obviously people make mistakes and there are some things that I would do differently in the future, but I’m not really sure that I would do them differently in the past.

Courtland Allen: Yeah. I think there’s definitely something to a team going through something difficult together and in some ways staring death in the face, like we might not make it through it and then making it through it and coming out the other side far stronger. It seems that’s what happened to you because since then you guys have grown from 15 people to 35 and your business is doing millions in revenue. What are some of the bigger things and decisions you made to emerge from that pivot and build an even better business than you had before?

Christine Spang: Yeah, for sure. I also want to give a quick shout-out to our series A investor 8VC. They were of super fantastic with us throughout the whole transition and I definitely don’t think we would have gotten through it without their backing and support. So I definitely want to give credit where credit is due. Yeah. I mean the first thing that we did basically after the first part of the transition was over was, we took everyone to a whole company offsite. This was 15 people at the time and we had to do this super scrappy. We just used the house of our VP of Engineering in the Oakland Hills because we just wanted to get out of the office and he was very gracious to offer his space. So we just sat down and went through the process of writing down who we wanted to be as a company and one of the things that came out of that was our open source company handbook.Which you can read on GitHub, which iterates what our values are, what the mission of the company is, a bunch of company policy things. I think that day was really important for changing a bunch of things about the company that we wanted to be different and getting on the same page about what we’re about. Just orienting that hey, we just went through this pretty challenging phase and we’re coming out the other side and we want to be all moving in the same direction. That was the first thing I think that was really important. I guess the other thing was engineering had to transition to everyone working on the back end. So we had to do a lot of teaching and mentorship and also started ramping up hiring again, and that was definitely a challenging thing to start doing again, and I think that this process of starting to articulate what we’re about has been really helpful with ramping up our hiring again. One thing that we did in the past year that’s really useful was work with, I think it’s a friend of yours actually who introduced us, Lynne Tye and who has this website Key Values.

Courtland Allen: Yeah.

Christine Spang: Which is awesome, you should totally check it out. Talking to Lynne really helped us articulate what was unique about us as a company and why people would want to join. I think that when it comes to hiring in the early days, the easiest thing to do is to really milk your network and just hire your friends because when you’re a tiny company and you can’t pay people anywhere close to market salary, it really helps to have a direct connection to other people. To get them to jump ship because it’s it’s scary and risky. So we had exhausted our network in the past and I think when you get to the point where you can’t just go to your friends anymore because you’ve already asked all of them, you have to work on building the brand of your company to extend beyond your network. So the first part of that is figuring out what’s unique about you and writing down and then sharing that. So these various different parts of the process were really helpful and obviously it works pretty well in that we have hired a whole bunch of people in the past year and have grown the company a lot. I also think that we’ve succeeded at staying true to the core of who we are by trying to find folks that values aligned with the company and that’s just pretty cool.

Courtland Allen: That’s super cool. I mean you said online that your main goal as you scale Nylas as a business is to grow company culture that you’re proud of and to see that you’ve been able to do that, especially emerging from a super hard time. It’s really impressive. I mean, it’s hard to grow a good company culture in any condition let alone the situation that you guys found yourselves in. What are some things you’ve done to create the culture that you’re proud of and what does that culture look like exactly?

Christine Spang: Yeah, for sure. I really believe that the roots of culture come from the leaders of a company. So a lot of what I do to help grow the culture in the way I want is to act in ways that I want people to replicate. So one of those things is basically giving people a really high level of trust by default. I have been described as earnest by many a person. I’m the person who believes what you say and who, if you’re in charge of something I will totally let you fail at that thing if that’s what you need and I think that giving this high trust by default helps establish that as a quality that exists at the company. I also think that having high trust and psychological safety is really the core of a well-functioning team. So that’s really what I keep coming back to time and time again, there’s a few other things that I also try to do that I think are really important. One is just being really reliable, show up on time, do the things you say you’re going to do. Be kind to people, don’t hold back when there’s things that need to be said, but also try to deliver things with kindness. Also one thing that I’ve learned from my family growing up was how to be gritty and tough and not give up when problems are hard. I think that one of the most meaningful experiences in life is to work with other people through a hard thing and accomplish something that you didn’t know was possible. In some sense that involves suspending disbelief of we can’t do this and just grinding through things even if it is really difficult. So yeah, that’s how I think about it.

Courtland Allen: You mentioned earlier that before you became a founder one of the things you heard from a friend was that it can be a stressful thing to do. We spent some time talking before this episode about how stressful this job can be, how stressful is you find it to be the founder of 35 person company. To have the burden of this company’s success and these people’s careers on your shoulders. How do you cope with that burden?

Christine Spang: Yeah, for sure. I would say the stress level is definitely a thing and it varies a lot. Sometimes I’m super stressed and sometimes I’m a lot less stressed. The things that are really important to me are essentially what it comes down to is making sure to take care of myself. I think with many things there’s a spectrum when it comes to self-care and working hard. Where there’s such a thing as using self care as an excuse to be lazy but there’s also such a thing as working too hard that you’re like neglecting taking good  care of yourself and it makes your work suffer.

To me, one of the promises I made to myself when starting this company was that I wouldn’t sacrifice my physical or mental well-being to make this company go because you only have one life.

Courtland Allen: Yeah.

Christine Spang: I don’t want to make it shorter and so I make sure to get at least eight hours of sleep a night. I think exercise is really important. I’m really into rock climbing and one of the things I really like about rock climbing is that I find that it very effectively induces a flow state. So when I’m rock climbing, I literally can’t think about work and I do think it’s really important to disconnect from your work, especially if it’s really stressful. You can’t be thinking about it all the time and often by disconnecting you can make your mind relax in such a way that you can solve problems that you wouldn’t solve by sitting in front of your computer and directly thinking about them all the time. So to me work-life balance is not about the number of hours that you work. It’s about making sure that you are getting what you need that’s not work. For me that’s some disconnect time, lots of physical activity, meaningful relationships with friends. I think you have to know some people that you’re close with, that are not in your company because otherwise you can’t disconnect.

Courtland Allen: That’s funny you mentioned being in a flow state because that’s something that a lot of software engineers will commonly tout as one of the benefits of programming, one of the things that makes it so enjoyable. You’re an engineer, you came into this company more as an engineer than it’s a founder really. What’s your advice for software engineers who are listening who are considering starting their own companies? What can they learn from your story and your experiences?

Christine Spang: One thing that I would take away is that you don’t need to be someone who’s always dreamed of being a founder in order to be a founder. One thing that I want to accomplish through this company is to be an example of someone who’s a little bit different from the standard person you imagine starting a company. Especially as a woman, there’s not a ton of women founders out there. I think that if you have an idea that you want to work on totally go for it. One of the best ways to create an environment that’s a good place for people who don’t look like the status quo is to start something from scratch because it’s easier to mold something that doesn’t exist than to try to change the trajectory of something that’s already flying in some direction.

Courtland Allen: I could not agree more and I think that you’re already a role model for a lot of people listening in including myself. So thanks a ton Christine for coming on the show and sharing your wisdom. Can you tell listeners where they can go to find out more about what you’re up to and Nylas?

Christine Spang: Yeah, so we have a blog which both posts about company events that we run and also about various different pieces of our technology. You can also follow us on Twitter @Nylas. If you’re in the Bay Area, you should totally come by our developer series of events. We have a group on meetup called Nylas Developer Events and if you come to one of these events, you will probably meet me and I’d love to say hi.

Courtland Allen: Great. Well, thanks so much for coming on the show Christine.

Christine Spang: Thank you Courtland. It’s been a pleasure.

The Nylas APIs power applications with email, calendar, and contacts sync from any inbox in the world.The APIs are also compatible with 100% of email service providers, so you only have to integrate once. No more headaches building unique integrations against archaic and outdated IMAP and SMTP protocols.

To learn more about the Nylas APIs, visit us here!

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