Yes We Can

Hi everyone, welcome back to this week's episode of Yes We Can. I'm just super excited to have Christine Spang here today.

Hi Christine, how are you? Hey Michelle, I'm doing awesome.

I have been following Cloudflare for a long time and love the innovation you guys are doing and just super awesome to get to meet you and have this chat.

Well, I'm so glad we got to meet you. I'm excited for our chat too. So just two housekeeping items or one housekeeping item before we dive in for all the audience tuning in.

If you have any questions for Christine, there's a way to submit them.

So please do. And if you have ideas of people you'd love to see on the show, please send me a message at yeswecanatCloudflare.tv.

I read every email I get and people suggest lots of great people who end up on the show.

So please, please share great ideas and people you'd love to see here.

All right, Christine, so let's dive in.

You are a software engineer by training and also now today the CTO and co-founder of a great company called Nylas.

There might be some people listening who aren't sure what Nylas does.

So maybe you can start by sharing with the audience.

Tell us more about Nylas and what you do. Yeah, for sure.

Before I dive into that, I just wanted to just let folks know, bear with me about the boxes.

I've just finished up a move and I'm not quite moved in yet. And I have a lot of books.

So it's a little bit of a work in progress over here. But in terms of Nylas, so Nylas has been around for about eight years at this point.

We're a API platform that makes it super easy for developers to connect to communications data and also to make sense of that communications data, to get insights out of it, to connect it to other systems and also to automate workflows involving communications.

We connect to all different sorts of channels. Email is a really big one.

We also connect to calendar, to context and to SMS. And I find it's really helpful to illustrate this with a few examples.

And because we're a very horizontal platform and a lot of the different ways that people have used us, we haven't predicted that.

We didn't go into a meeting room and figure out like, this is what are the things that people are going to build using Nylas.

We kind of started from a position of just wanting to kind of democratize and make it easy to use this really valuable data.

And then all of the amazing developers out there have really been driving what exactly people are using it from for.

So, these are not the only things you can do with Nylas, but these are some things that people have done and have gotten a lot of value out of it.

One example is that, for example, we have a really large e-commerce company that is a customer and they essentially use us to connect to essentially like a feed of all of the orders that people have made because that data goes to their email mailbox.

And then we have technology to essentially tune into that really big feed of unstructured data, a mailbox.

You get all sorts of different kinds of messages coming into email, things that may be personal message, there might be documents, there's receipts from all these different companies.

There's just tons of data that you have to sift through.

And if you only care about one particular thing, like in this case, orders, things that people have bought online, then it's just a huge amount of work to build the infrastructure, to filter through this data, and then to connect that data to your other systems.

So, we essentially do all of the kind of heavy lifting around just connecting to all these data providers and then also the filtering piece and sort of structuring the data and just giving people basically a JSON feed of this is the data that you care about.

And now you can connect it to your other systems.

You can put it in a database. You can use it to power features in your applications.

And it just really relieves a lot of the hard work that people would otherwise have to essentially have entire engineering teams dedicated to building, which is not the point of this application.

There's plenty of other things for them to be doing. So, that's one example.

We also have tons of variations on a CRM that are using Nihilus.

There's all sorts of different flavors of this these days. And at the end of the day, people everywhere need to keep track of their customers, need to communicate with them, and engage with them.

And we essentially allow people to build email communications, things, and pull data directly into their apps so people don't have to be contact switching all the time and switching to their email clients and having a lack of comprehensive data in that one tool for managing their real estate business or their customer support.

Lever is a customer of ours. We're also working with sales loft.

And there's just a lot of companies like this who use us to embed communication features into their application.

And it's interactive.

So, we also power sending. And it's not just about bringing the data in, but also about what actions are you performing.

And we can essentially do that for the user as well, all within our customer's application.

Nihilus sits behind the scenes.

We're fully white labelable. In the ideal case, people shouldn't even know that Nihilus is involved unless they're digging through the terms of service and the vendor list of a product that they're using.

We really want our customers to be the ones that are owning that full end-to-end user experience and to be the brand that their customers are seeing and associating with.

Amazing.

I'm trying to think of a good analogy because as you're talking, obviously, you build real infrastructure to help power these communications for your customers in lots of different industries, right?

And it's like all these signals come to Nihilus and then Nihilus makes sense of it, structures it so it can go back out and add value to end customers and users.

And sometimes it's amazing in technology that that even exists.

That's even a problem that existed. How did you find this problem?

Because I don't think you woke up one day being like, here's a problem.

I was assuming you felt it in some way. Yeah, for sure. Just kind of going back to your point there, I think the fact that this platform has ended up being kind of so horizontal and in so many different verticals and industries, it basically points to the fact that there's this core kind of human need that is universal.

It's about that communication and interaction. And the vision when I started the company was not as broad as it is today.

And I think this is the case for a lot of companies where you start out solving a very specific problem.

And in Nihilus's case, it started with email.

And the problem that we sort of ran into in the early days was that email is really old.

It's older than the web itself. There's a lot of diversity in terms of the protocols that you use to access a mailbox.

And it wasn't really designed for this world where software is integrating and connecting to all of the other applications out there.

And this is something that it's this huge trend where as software kind of permeates into more and more industries and is powering more and more of what happens in the world, there's more and more of a need for that software to interoperate and to integrate with each other.

And so we kind of ended up with just this ton of data that has ended up in email that happened very organically.

People started out using it as a replacement for sending paper letters.

Then just things sort of layered on top of each other until we kind of ended up with this giant document store that was essentially unstructured.

And so the spark that led to Nylas was like, there's all this really valuable data in email, but it's really hard to access.

And it seems like people should be building more things that connect to that data, but why aren't they doing that?

And the thesis was that it's just too hard. The barrier to entry was too high.

And what if we could build something that made it easier? So the very first thing that Nylas the company built was just an abstraction layer over all of those protocols for connecting to a mailbox.

And it started out with just that.

And everything that we've built since then over the years has come from looking at what people were trying to build and what we're trying to accomplish, having all those conversations with people about what problems that they were having and seeing that there were overlapping use cases and that we could expand to help fill more of.

If you're looking to pull data from email, you often also need to do scheduling.

Those are powered by the same providers. We could use the same authentication and all kind of gradually branched out and expanded the capabilities of the platform based off of what we were seeing in terms of what people wanted to build.

So that's really where we came from. When you're speaking, Christina, all I could think of is it's almost like you kept pulling the thread.

The thread kept going.

You're like, there's something here. There's something here.

There's more and more. And all of a sudden, eight years later, you have this company with a lot of customers and a lot of teammates working every day to help empower all this.

Where did you come with the name? How did you come up with the name Nylas?

Yeah. It's so funny that company was actually originally called Inbox, which we started with email.

It kind of made sense. It was like you're accessing an inbox.

But we ended up changing the name in kind of the early days because Google launched a new email app called Inbox.

And we call up our lawyers and like, what can we do about this?

We can't compete with Google for SEO.

And the thing about trademarks is that you really can't use a generic word and trademark it in the same context that it applies to.

So you can have Apple computer, but you can't trademark Apple orchard because all orchards have apples.

That's confusing.

So they're like, this is indefensible. You can't do anything legally about this.

And so we were 10 people at the time or something, and we decided we just had to change the name.

So this was sort of an urgent thing. We ended up hiring essentially like a brand design company to help us figure out what are some ideas.

And you try to find a name that's memorable, that sounds nice, that's easy to pronounce, and that you can find a domain for.

And so that's kind of how we ended up with Nylas.

I think the one criteria that it's weakest at is the pronounceability.

People still sometimes get confused about how to pronounce it. Oh, what do they say?

I feel like it's pretty straightforward, Nyla. Like, Nylas sometimes, or yeah.

I mean, it's just phonetic, right? Yeah. Or Nyla. It's so interesting you say that because I was just talking to another founder two weeks ago, and they're going through the process of changing their name, but they're a lot more than 10 people.

And a lot of us are like, oh, there's just so much brand equity built up that we've got to change our name.

And so I think it was maybe a blessing that it happened at 10 people, Christine.

Maybe it's one of those times you're like, why do I have to do this?

But looking back, I'm like, actually, it's good.

And like Nylas, it's very melodic. And it's interesting just on this topic, we've named Cloudflare.

I love Cloudflare. But a lot of people can't pronounce it. They say Cloudfair all the time.

And also, Flare can be spelled two different ways. And it became, when we were naming it, we got it right away.

Matthew and Lee and I, it was not a problem.

But as we've grown, sometimes I'm like, oh, we maybe could have picked a different name from the beginning.

But anyhow, it turns out naming things is hard.

Yeah, that's so interesting. It's kind of funny because we've had a little bit of a twisting path in terms of the product.

We built the APIs.

And then we also, we went down this path for a couple years. We were building this email client that was extensible on top of the APIs.

And if it had been kind of like the perfect iteration, we would have changed our name after we sort of stopped doing the email client.

We spun it off. But for a long time after that, we had this problem where everybody who was coming to a website was looking for the mail client.

And I think it's at this point, it's totally fine. We've kind of pivoted the brand.

And also, there's a ton of developers out there who will be like, oh, I remember Nylas Mail.

That was a super cool app. And so it's still kind of nice to have that associated with us.

But for a year or so, we're like, maybe we should have changed the name again and just started from a clean slate because everyone's confused.

Anyway, these are the stories. These are the stories that you don't always hear.

So thank you for sharing all those. Okay, so we're going to come back to Nylas.

But before we do, I'd love to go back before that, because before you started Nylas, right, so you did your Canadian, you did computer science at MIT, amazing school.

And then you actually went and you started your career at an early stage startup.

I mean, I think it was like 15 people when you joined.

So I want to hear a little bit more about how you found that first job. And then in what is super interesting and kind of the great Silicon Valley story is that startup got acquired by Oracle.

So then you worked at Oracle for a while. And now you've since started your own company, and it's going really well.

But I just, you know, when you think back to that initial startup, how did you find it?

And then now, you know, now that you've had that breadth of experience from very tiny an acquisition by Benhemuth, I mean, Oracle is a huge, huge, large technology company.

And now you're running your own company. I'd also love for you to share some maybe lessons learned or reflections with the audience.

Yeah, for sure. So that startup was a really interesting experience.

And honestly, a very positive experience is how I got into entrepreneurship in the first place and kind of what connected the dots for me in that, you know, I, I didn't really know anything about entrepreneurship.

When I was in college, I had a very sort of tech heavy, like open source background where I got into software engineering through open source.

And I was really into Linux and big into kind of these open source communities.

And so this startup, the way the way that I ended up working at this startup was because it was essentially like a spinoff of the essentially the computer club at MIT, and they were commercializing some Linux kernel software.

And so I started working for them because I was sponsoring uploads to this Linux distribution called Debian for one of the founders of it, who I knew through this, the computer club.

And so it's kind of a interesting connection. And I'm not sure I would have gotten into the startup world without that, you know, sort of spontaneous thing that happened.

So it was a really small company. It was around 15 people for sure.

And it was a bootstrapped company. So a different path for sure.

And, you know, bootstrapping, you know, has has a number of different characteristics, like you're not, because you haven't raised so much money, you're not pressured so much to really grow really fast.

But you also have a lot fewer resources, because you have to earn every dollar from customers.

And so it was a super great experience, super scrappy, like, you know, we worked out of the founders house.

And, you know, we had servers in the basement and stuff like that.

And just seeing kind of the whole arc of a startup through that, you know, I wasn't there as an independent company for super long, I guess I worked there for a year, and then the founder sold the company to Oracle, and, you know, a modestly successful outcome.

And then I got to see the whole integration process of, like, sort of a giant company, acquiring this tiny company.

And I think we might have been the smallest company that Oracle ever bought.

And they had this sort of one size fits all process of, you know, the same thing that they used to acquire Sun Microsystems, we had to jump through all the hoops, which was wild.

And I, you know, that that startup was my first job outside of after college.

So I didn't really know what working like a big company was like.

And so the first year, I would say that, you know, I was shielded a little bit from like, you know, the red tape that happens in a in a really large organization, because, you know, they essentially kept the company the same and just sort of plugged it into a larger structure.

And then, but there's a lot of things that happened really slowly, that seemed quite frustrating, as someone used to a really agile environment where we could just make a decision and move on, you know, things like, you know, going through the process of moving our servers into an Oracle data center, it seemed like there were problems that we had to solve that were just like, how do you find the right person to talk to to figure out where to put these, which, you know, like, I'm an engineer by training, I didn't, I felt like I didn't get my degree in software in computer science from MIT to figure out, like, solving this kind of bureaucratic problem.

And so, and things just moved also a lot more slowly. And over time, I felt like I was stagnating, and I really wanted to do something that was more faster paced.

And it was a comfortable job. But, you know, I felt like if I stayed there too long, I'd get left behind and the whole world would have moved on without me.

So I guess I like to be at the cutting edge. And so here we are, creating the cutting edge, literally inventing the future, which is super exhilarating and hard at the same time and rewarding and frustrating.

You can hold all those emotions at once.

Yeah, for sure. You know, I think that is really that experience of, like you said, you were a part of the computer club at school, and it led to this job that you didn't even know kind of existed as a career choice.

And it opened your eyes to all these sorts of things. I love that story.

I feel like I hear those stories all the time in technology and entrepreneurship.

And I'm a big believer, like life is a collection of experiences, just like go collect a lot.

And I think that that's a good message for folks like you're just to kind of pay attention, just try things.

Yeah. Yeah, at MIT, it was very common on campus to kind of poke fun at the business students as being like, you know, less hardcore than the engineering students.

And just looking back at that, you know, I'm really grateful that I ended up, you know, on this entrepreneurship path, essentially, you know, through that technical path, because today, I see business as like being a great way to make an impact on the world and kind of wish that like, it's kind of seems kind of like a very small minded thing to be like, you know, business students, like, make fun of them, that kind of thing where you need all sorts of different specialties and personalities in order to create something great.

And also, definitely in in the US and in America, in the West, you know, business is like the dynamic energy that moves the world forward.

And yeah, I kind of came to that through winding path. And I almost wish that I'd been able to come to that realization sooner.

Yeah, yeah, no, I think that what you're saying resonates so much where it's I, you know, I, I'm a chemist by training a scientist by training, but went to business school.

And then Matthew and I met there.

And Matthew's got a technical background, a legal background.

And I remember when we started cloud for a lot of people like, why are you starting with Matthew?

And people would sit with Michelle. And it just wasn't and we were just so different.

But that's good. As a founder, you don't want your co founder be the same person as you, you, you want to be complimentary.

My co founder, Gleb is a very different person for me.

And it's great. It's amazing.

He's a super huge business nerd. And I really appreciate that. I just, you know, don't, don't look down on people with other, other specialties and perspectives, because you need both like, you know, the stereotype for people coming out of MIT is like, they're really great at technology, and they like, can't sell worth whatever.

And you just, you need to get the word out there, you need to figure out, you know, how to like, show people the value of what you're building.

And I just really believe in that collaboration between, you know, different kinds of people to make things happen.

And I just think it's really important to be open to that.

I love that. There's so many wise words there, Christine, thanks for sharing all that.

Also very poetic, actually. Very well, very well said. So switching gears. So back to Nyla.

So now today, you run a large team, you've over 200 people, over 250 people at your company.

You went from a co founder, your C level executive, but you're also a manager and a leader running a large team.

That's a lot of people. And so what have you learned about people management and leadership, especially on your journey?

I'd love to hear kind of some of your reflections around that. Yeah, for sure.

The job overall of a co founder is to build the company. And that looks very different at different stages of the company.

When Nylas was super tiny, less than 15 people, I was building the product, you know, I took that software engineering training and was using it and committing a lot of code.

It's super funny, I was just chatting with a team member earlier today, where they pointed out that, despite really not committing that much this year, I'm still like super high on like our GitHub stats, just because of past contributions.

And yeah, we wrote a lot of code back then.

But the thing that's tricky, and that, you know, I feel like has been a real journey for me is going through those different phases and having to like, look at what you're doing in terms of building the company in very different ways, because you're doing different things.

First, first, you may be, you know, building in a very hands on way, then you might be running a team that is doing the building.

And that's just even going from that direct building to managing a team.

That's, that's a whole journey, it probably took me, I don't know, two years or something to really feel like I got the hang of it.

And I remember when we got to the point, it was like, you know, 10 or 12 people or something like that.

And, you know, the wheels start falling off the bus of just like, winging it.

And I reached out to, so I started Nihilus when I was pretty young, I was 24.

And so I didn't know a lot of people who had management experience, because I wasn't old enough.

So I reached out to like the one friend I had, who was a little bit further on who had like run teams.

And I was like, are there books I can read?

What, what resources should I consult to, to learn some of these skills, because I just have no idea where to start.

So he recommended me some books. The one that I remember most is this book called Becoming a Technical Leader by Jerry Weinberg.

And that was super helpful. And just like how to sort of shift your mindset from that of like someone directly building to someone who's leading a team.

And then, you know, Nihilus today is about 250 people. And at that scale, I'm not even like running a team directly.

I'm like, running, like running an organization that has other people that are running the teams is another layer down, which I think I'm still in the process of sort of really feeling comfortable with that and sort of giving direction at a higher level.

And I think it's really tricky to kind of switch back and forth between all the different things that you have to do.

Because like as a founder, you know, I have an operational role that changes usually every six or nine months or something like that.

You know, I try to line up what are my skills and what does the company need right now.

And I talked to my co-founder a lot about, you know, what should I be doing?

But then there's always like 20% of my brain that's thinking about the entire company because it's my baby.

And like, you can't just not think about that. Think about the culture.

Think about how we're doing. Think about, you know, fundraising. Think about like, you know, what are we doing in the next year and what are the problems we need to solve?

Like, what are the gaps on the executive team? So there's all that, that like the thing that I find most difficult is like shifting between these sort of different ways of operating.

Because you almost have to like reprogram yourself in order to like be in a different role.

And then just like having different hats and switching back and forth between them is, it's kind of tricky, but it feels, feels like doing like, like pushups, like you get stronger over time.

You get better at it. You for sure get better. I think that I've heard two analogies on this one that's good, where I think what you're saying, what you're describing is, has definitely been my experience.

And it's almost like you're a puffer fish, like you become, and you never quite go back to the same size because you've gotten stronger.

You've like kind of, and so and it just, the journey continues.

And then the other side of that is actually I heard someone else was like, this is crazy.

Like I got to switch gears. It's too much. And they kind of went to a bigger company and kind of a cushy job.

And like, they were like, oh my God, I miss it.

I need, I need this other thing because totally my, you know, my girlfriend tells me whenever I like complain to her about how stressed I am.

She's like, but you wouldn't have it any other way.

You'd be so bored if you were, you know, working at, you know, one of the big tech companies, it would be too slow for you.

So, you know, the grass is always greener, but it's good to have someone you trust to remind you that this is the way that you like it.

I agree. And I guess another thing that I wanted to mention was that I think it's really important to, to not forget that the things that you've gotten really good at that now feel easy are still really valuable.

And that there's other people that those things are not easy.

And it's really easy to discount, you know, the value of something that doesn't feel like hard work to you when for other people, you know, that thing might be quite difficult, but like you only have your own perspective.

And I think, especially as women, it's really easy to get into that mindset of like, well, this thing isn't hard for me.

And so it's not that valuable, but always good to remember, find someone to tell you what you do that is uniquely valuable and that you're really good at.

It's useful. I love that. I need to hear that today, Christine.

That was a good one. That's a really good one. Okay. We have about a minute and a half left, which is just the last three minutes flown by.

But the last question I want to ask, ask everyone on the show is as a woman in technology and you're like really hardcore tech, where has the industry lived up to your expectations and where has it fallen short?

Yeah, I think, you know, one of the things that I appreciate about tech so much is that it's really fun and interesting.

And that's definitely, you know, how I got into it in the first place, just kind of following curiosity.

I, I lucked out on the weird hobby lottery and you know, got into programming in high school and just so happens to be the wave that is powering the 21st century.

And I'm just so grateful that that is the case. And I hope that, you know, more people can get into it.

Because I just really loved programming.

And so that piece of it is definitely I lived up. I don't think that I realized how amazing the career opportunities and sort of room for growth and impact would be when I got into it, because I was just following something that seemed really fun and interesting on like a curiosity level.

So maybe has exceeded expectations in that way.

In terms of the shortcomings, I get really frustrated that I still hear from my people on my team about things that seem like they're really basic that tech is still doing wrong.

Like for example, I've heard from people of color on my team that there are things like, you know, my webcam doesn't display me well in low light.

And it's just crazy to me that after all these years of conversations about how our own sort of lack of testing or lack of diversity in sort of the perspectives of building things, and we still haven't really fixed it.

And I think that's a gap that we really need to fix, because software is only becoming part of more and more different things, more and more parts of our daily life.

And, you know, it has the possibility to be a great equalizer, both in terms of being this really sort of upwardly mobile, mobile career path for anyone with a technical aptitude.

But also just, you know, as a society, we can sort of choose what to encode into that software.

But if we don't choose, like mindfully what's in code, you know, we just end up embedding in the, you know, the biases that already exist and the inequities that already exist in society.

So we got to do better.

And, you know, I think, hopefully, we'll keep making progress there.

I couldn't agree more. Christine, we're out of time. Thank you so much.

This was I really enjoyed our conversation. Thank you so much for tuning in.

Thanks, everyone for tuning in. Christine Spang, CTO, co-founder of a great company called Nylas.

Check it out. And we'll see you here next week again at Yes, We Can.