Brien Colwell, Co-founder & CTO @ Headspin: The value of company culture to startups.

This episode features Brien Colwell, co-founder and CTO at HeadSpin, a mobile performance platform for managing user experience globally. Brien previously founded a Y Combinator-backed startup, Nextop. He also worked on mobile architecture at Quora, and early product development at Palantir Technologies. Brien graduated from UC Berkeley majoring in Electrical Engineering and Computer Science.

Brien shared his career path from an engineer to a tech leader and entrepreneur and his insights on building a unique culture for start-up companies.

Highlight 1: What is a rewarding startup culture and how to build it?

Highlight 2: Early days at Palantir and interaction with Peter Thiel

Watch the full interview: is a content platform dedicated to helping engineers and researchers develop leadership, entrepreneurship, and AI insights to scale their impacts in the new tech era. Sign up with us to stay updated and access exclusive event, career, and business mentorship opportunities.

Full Transcript

Wenli: So you went to UC Berkeley for undergrad. How was it like growing up here?

Brien: I grew up in Nevada around Lake Tahoe, just down the street from Lake Tahoe in the Colina area, outside Reno. My dad had a computer shop, he sold used computer. I was actually born in the Bay Area and then moved to that area. My dad opened up a computer shop. That was interesting for me, because at the time in the 90s a lot of kids were just kind of getting into computers, getting into programming. So that's kind of how I got into it, just started making websites, started selling websites to people. I went to school at Berkeley and focused on electrical engineering first. I don't want to insult the hardware guys out there, but it seemed like a lot of the most interesting stuff was happening in software. Towards the end of my undergrad, I started focusing much more on software.

Wenli: Yeah, that makes sense. You were majored in electrical engineering and then to computer science. After graduated from UC Berkeley, you were hired by Palantir Technologies. It is one of the most secretive startups in the Valley known by the job it does, it helps governments and spy agencies to find terrorists. Is that right?

Brien: I can’t speak to it. But yeah, that's right.

Wenli: How was it like in 2006, when you joined the company?

Brien: Great question. So coming out of college, I had a job. I actually worked as a programmer already for a company out of Tahoe. I was clueless about what do I do with my career, because I was kind of just writing code and just kind of doing my thing. And my undergraduate advisor whom I've been doing infoVis research with actually met with the Palantir folks. So it's kind of an example in the Silicon Valley, connection just happens out there. And I think it's a really magical thing to be in this area. Because a lot of people talk, a lot of people interact. And a lot of things surface up in ways that aren't exactly obvious out here. And I got the intro to go, talked to the Palantir people. And I went over there, I didn't have a car at the time. So I was in Berkeley, I took the bus out to Palo Alto on Page Mill. So it was in the basement of a bank on Page Mill.

Wenli: How many were there back then?

Brien: I was in the teens. I don't know the exact number, but everyone was like in one room. For me at the time, I didn't really even know what to prioritize in my own career. Like, what do I prioritize? I prioritize money. Do I prioritize learning? Do I prioritize trying to start a company myself one day. And the thing that really struck me walking into that initial Palantir office was that, everyone was working very hard. It was very apparent that people were working, they're building something. And it seemed to me like an environment that can join and learn something. So that's why I started, I think I just took a bet on the team. They seemed like a smart group of people whom I could learn with.

Wenli: During your years working there, did you have any chance to interact with Peter Thiel?

Brien: Yeah, so Peter Thiel came in and out of the office while I was there. So he'd be around certainly, as an advisor. When we did our first release, I think about a year after I was there and started, we kind of cut the first version with some first major contracts. And he took us all out to dinner in his house, so he hosted an event next to the Palace of Fine Arts in San Francisco, which was very nice. I remember I was thinking at the time the numbers, like how much he paid in rents and the stuff. It's all staggering, right? And I think sometimes in Silicon Valley, it is pretty amazing. You can interact with very successful people, work with very successful people. And you're also working together, building something. And I think a lot of people in Silicon Valley think it's interesting that they don't just take their money and leave. It's like, if you make money, a lot of people re-invest, a lot of people try to mentor the next generation. And so he was around for sure, even though he's obviously a very successful entrepreneur.

Wenli: So you mentioned that you went back to Tahoe for your first job after graduation, right?

Brien: I had a job in Tahoe. I worked there during undergrad. And I was also deciding like, do I stay there? Or do I do something different? And I chose to move on to Palantir.

Wenli: Coming back to Silicon Valley?

Brien: Yeah, because I was at school here.

Wenli: Okay. So after a year and a half working at Palantir, you decided to move on. Did you figure out something, like why did you left Palantir, such a great team?

Brien: Yeah, that's a great question. I think it's something that everyone deals with, the idea of burnout. And I think I was burning myself out. I think that's something I learned later in life, that you kind of got to moderate yourself, especially if you view this career like a marathon, right? You can't just burn out in a year, or two years. So I was definitely not healthy, not taking care of myself, not really happy in a lot of ways. I was just working really hard. And I think that plus trying to explore other interests was a major decision for me to go out to Washington to take the research fellowship.

Wenli: How long was the research fellowship?

Brien: A year.

Wenli: Was it a good break for you?

Brien: It was good. We got some papers published, and some top human-computer interaction conferences, and meet people who was the first engineer to join HeadSpin. He has been there since the beginning. Actually I met him at U-Dub (University of Washington). Sometimes you need to step out, meet new people, get new ideas. It was a good break for me.

There's a piece of my history that I was skipping over, which was I moved to New York City for four years. And I actually went to art school in New York City. So I started a master's degree in New Media and did that for about two semesters, financial crisis happened. And I think that was sort of a moment for me that I realized, I got to figure out how to balance everything a little bit better; I got to figure out how to balance creativity; I got to figure out how to balance like doing something I believe in; I had to figure out how to balance making money, running a business. And so at that time, one year in art school, I started working with this little company in New York, started by some musicians, like concert pianists and composers, great backgrounds, building enterprise software and being very successful selling enterprise software in New York City. And I just felt like, this whole experience of working with this group was kind of eye opening in a lot of ways. They had a lot of interest, they were very well rounded, but they were also able to succeed in business. My move back to Silicon Valley to start at Quora was really a way for me to learn again, because I wanted to figure out how to balance this for myself, right? Like what's the balance of engineering skill, or business skill to be able to make it long term in this industry, like really love the industry, really love the business and building. And Quora was the first step of that, to work with these really smart people.

And then the next company I went to was similar. It was a Mobile first messaging company focused on remote working called Talko. For me, it was also learning experiences, building this mobile app, that's like real-time. And this was before Slack launched, it was essentially a slack product before Slack. And slack launched like right as we were getting ready to launch. So then this company got acquired by Microsoft, later became part of Skype for business. And at that time, I had started my first company.

Wenli: Was Talko your first experience to build a mobile app? Was that the first one?

Brien: No, Quora. I did mobile apps at Quora.

Wenli: So you started your first company, Nextop. What do you like about entrepreneurship?

Brien: For me, I think it was a couple things that I felt like really drew me to creating a company. One was to work on problems that I found interesting. I was basically drawn to the way people were building mobile apps, because I've gone through Quora, and then Talko and seeing a lot of issues with building mobile apps, deploying mobile apps. And then the other piece that drew me to starting a company was to create a culture that I really liked. Sometimes it's hard to find a company with the right culture working in the problems you're interested into. And so I think one great thing about being an entrepreneur is, if you stay true to actually solving the problems and you stay true to building a good culture is you can actually have a company that you really enjoy working at. You don’t dread going to work every day, you're not just thinking about like, when am I going to get acquired, right? It's like you actually want to go to work every day and solve this problems. And that's what I wanted for myself, to create that environment.

Wenli: Nice. After your first company that you co-founded - you are currently the co-founder and CTO of HeadSpin. Can you tell us briefly about the company?

Brien: Sure. So HeadSpin is a global platform to help teams making mobile apps build better mobile apps for their target markets. A lot of companies who are out there building mobile apps fall into two categories. So they either have sort of a quality team in place so that they write the test, test their apps, they evaluate them. So HeadSpin can take your current tests and your current team and expand that over the entire globe. So we have access to over 100 different countries. And there's also a set of companies out there building mobile apps that don't have an existing quality team. They don't have anyone really focusing on testing the apps. We also help those companies by offering them an easy way to get going with continually measuring their app quality. So every day, how’s my app doing in Brazil, how’s my app doing in Japan, how’s my app doing in Australia, how’s it doing in North America? Just give me those quick updates about how is my app working from a user perspective in these locations, given that I don't have anyone doing this. So HeadSpin came into a market that had some existing players. And then partially, our goal was to take the work that people currently do in the space of the investment that teams currently have made in testing and quality and amplify that. So let's take what they currently have and amplify it, but then also give them new tools to go further with quality and monitoring of their apps.

Wenli: Is that how HeadSpin differentiates itself from competitors?

Brien: Yeah, absolutely. So we go very deep in data, we call it high-fidelity data. So being able to take a user using your app, look exactly what they see and our system annotates regions that could be improved. So we have an AI team that builds very sophisticated models. And additionally, part of our AI analysis is actually doing what used to have to be done using references. So for example, here's a good session, and then tell me when it changes. We've actually built a system that can adapt, so you can put an app into our system, and it can tell you what's broken, or what's wrong without ever having seen your app before. So we spent a lot of time on that data, on that machine learning to be able to help you understand if your app is broken, without ever telling the system what’s right or what's not right. So think about it like going to a hotel. And the valet comes out and takes your car and parks in the right place. And then they give you your keys and you show up, and there's like a warm towel on your bed. That’s exactly the same experience that has been brought to app developers, which is, you don't have to know anything about the process. But we're going to guide you to getting the value to building the better app. And that's something that doesn't exist currently out there. It’s something that has been innovating.

Wenli: Who are the typical customers that you have?

Brien: We work with four market segments. Basically anyone launching a mobile app can be our customer. So we work with enterprises, telecoms, app developers, and also government, governments are going to need the apps and all these stuff.

Wenli: You previously mentioned that you really value the culture. What kind of culture do you think you and Manish created?

Brien: It's a place where people can learn. Obviously, like you go to a job, trying to do the same thing for the rest of your life. Every job is kind of a stepping stone to go somewhere, to meet your own personal goals. So everyone at HeadSpin takes on a huge role. Everyone has a big opportunity to work on big problems, they get visibility and credit for the work that they do. Like someone's releasing features, everyone's really rooting for them to get that feature out, really rooting for them to make that big improvement to the platform. And I think the culture is really great that way, that everyone's trying to see everyone else advance, grow, becomes better at what they do.

One of my core values is, besides growth, just giving people the freedom and the space so that they can actually do their best work. What you see a lot of time in a big company is that, you'll work really hard on something for like six months, a year, and then you want to release that thing, and then it never gets released. At HeadSpin, I think one of the great things we have is like, everyone works on stuff that gets released. To me, that's a great culture. I think it's a very distributed culture where instead of having everyone trying to fit into someone else's vision, is basically trusting people to run with their own vision, and take their own ownership of what they're shipping and get that visibility of, this is my feature, this is my products. I'm really responsible for getting this out. And so that means a lot to me.

Wenli: Sounds like a very warm and supportive community to work with and lots of smart people. And people can find mentors, and you've been very supportive. I think that's really important. HeadSpin was invested by Google Ventures. How did you find them?

Brien: This one was actually not that interesting. Manish’s previous company had been acquired by Google. When he was thinking about leaving Google, Google Ventures wanted to make an offer to invest in his next company. So we were deciding between Google and a couple of other VCs. We ended up deciding to go with Google, because they’re a really awesome firm, obviously a great partner to have on board, especially being one of the largest developer ecosystems in the world.

Wenli: So they will bring more resources?

Brien: More opportunities. Introductions, potential engagements to work with.

Wenli: Besides of Google Ventures, there are some other great ventures that you invested in your company as well, GGV and Battery Ventures? Can you tell us a little bit about how you attracted those venture?

Brien: I went through Y Combinator. Y Combinator is one of the best business schools that an engineer or a tech entrepreneur can go through. It will very quickly realign your vision for what investors look for, and how you actually should be thinking about your company to attract investors. Investors obviously look for potential, they look for the growth. So you need to focus on building a business that has a real business, right? It has growth, it has revenue, it has a path forward, it has a plan. The best thing you can do for your company is basically focus on getting that initial attraction, getting those initial numbers, those initial customers. Showing that you have a product that solving hard problems, and solving problems for these customers. In this case, that was how he did it. So we got customers, we just kept building product, kept getting customers. Because we're a company that grows every year, we have a great growth, we'll get the best investors on board through that growth. So I think we've been very fortunate, because a lot of our growth actually come from product, just straight product, I think we're building a great product, solid product that is solving the problem. Sometimes, companies have a great business plan too. And I think we've done some great stuff on the business side. But usually there's a combo that you write a great product, a great business plan that puts your numbers in place. And that's how you can get some of the best investors on board. In the past, sometimes it's who you know, those are the people who are going to take a bet on you. But it all depends.

Wenli: We talked to other investors, like from DCVC. And one of the investors actually told us, besides of very solid product, they also see the entrepreneur himself to see this is a great leader, and the team. So as a CTO, besides of technology problems, you also have to work with the team. What's your takeaway from team building?

Brien: Yeah, that's a great question. Incredibly important. I think actually teams is my number one job. It seems kind of strange to say that, because there's the technology to build, there’s the certification to get, there's company to build, sales teams to support. But without a great team, you can't go anywhere. So you can't grow, you can't get that momentum. So some things I tried to do when building team or look for leaders, it's hard to grow a team without those corner pieces on the team. You also need to get people in the company. So like, if you have a company just for leaders without the raw talent around them, that's also not a great team. So part of this comes out of recruiting. I think recruiting is really interesting. In the current environment of Silicon Valley, especially with the things like coding academies coming out, sometimes as a startup, you have to be a little more scrappy with how you recruit, how you get people in the company. You have to look at things like people in transition points. So people going from large companies who want a startup, people who started going through a skill transition. So one skill, like retraining through coding academy, or advanced boot camps until trying to get into the computer field. And if you focus on people who are hungry, they have the passion, want to work hard, and then put them around great leaders, I think it's a pretty good way to grow a good team.

I do think it's also important that people know what they're building. It's actually interesting for me to kind of reflect back on say, my first job, like we had talked about at Palantir, which is you joined this company, it’s like, very driven by some people with a vision. And they're asking you to work really hard to build this thing that you might not even know like, what is it doing? And you can go with like with blinders on for a little bit, you can work for a year or something, just like heads down, crank away, ship stuff. But at some point, to really be holistically like, enjoy and engage with work, you have to understand what you are doing. I think it's important for founders to keep that in mind.

Wenli: As a leader right now, how would you describe your leadership style? Like how do you deal with conflicts?

Brien: As a leader, I like to just jump in and take on the hard problems, help understand the hard problems. Because I think there's an aspect of a small team, which is essentially incredibly isolating to be on a small technical team. A lot of times you feel alone. And as a leader, I think one of my roles, especially on a technical team, is to make sure that people don't feel like they're alone on a problem or they’re stuck on a problem, is I like to jump in the problems with people on the team, help them through, get the ball moving, so everyone can feel that progress and feel like they're moving forward. And that's what I could think of leading from the front. I do think that a leader also has to step back and give the vision, like where are we going, what are we building, how's it going? I think as a leader, when you're in the front, sometimes you have to step back and do that. And it's a lot of going deep and coming out. I think that describes my style as very much going to the front, coming out, working on direction and then going to the front again.

Wenli: Where do you see HeadSpin in the next couple years?

Brien: Where I see HeadSpin going in a couple years, is actually a tool that I hope everyone gets a chance to try. Currently, we work with a lot of enterprise customers, working with testing teams, which is great. We can help an existing testing team make a lot of progress and look at their app differently and multiply their efforts. But I see HeadSpin as being a tool that integrates with every mobile developer’s workflow.

Wenli: So definitely market growth. That's something that HeadSpin is focusing on right now. Any challenge that you're facing on technology side and market side that you can share?

Brien: I think there’re some interesting stuff for HeadSpin. We sponsor some open source, I think that's a really interesting question that probably every company at some point has to think about is get open source. When you're on the forefront, it’s actually kind of this interesting inversion that happens in multiple aspects of software technology is that you have a lot of people using software that a few people make. And typically, those few people are in open source communities. So what's kind of interesting is, from a business perspective, or tech perspective, when you're trying to build software for developers, one of the best places to get all the feedback from the developers is to integrate with those key projects that all these developers are using. Because there's a few projects out there that 80% of developers use. And so to understand what challenges we have, you have to actually connect with the community. And one of the great ways we connect with the community, is especially to sponsor some key open source projects. That actually helps us a lot, understand the technical problems, because as we're trying to help mobile teams solve their problems and make better apps, we're also seeing what problems they’re having with these open source, which we can actually help them with our technologies.

The typical problem is, we have a global platform. Managing global platform is very hard, especially with the startup size team. So we have locations in over 100 countries, we manage our networks, we manage the availability, the security of this whole system, as well as the technology. We work on this very large distributed systems. So I think there're just a lot of challenges in that. But thankfully, I work with some really, really smart people, and we’re able to build this out, and keep growing, and keep adding new features on a regular basis.

Wenli: Thank you for sharing about that. It comes to my last question. We talked about that you learned a lot from YC, as you think it was a really good business school for engineers and entrepreneurs. Can you share with our community some of the most important things, or even just one thing that you learned?

Brien: So you might really like an idea. But you can’t sell it, or you can’t get people using it. There's not a business, and you have to move on from that idea. This process of listening to customers, listening to their objections, iterating, trying to solve these objections, trying to figure out what the root problem is. That process, I think YC will really drive into you, because you're trying to, in a very short period of time, get your numbers up. And if you don't have something that's working, there's only so much marketing you can do. Like, you can't spend $100,000 on something Google has every month. You have to fundamentally listen to customers and improve your product and build things they want to get in front of a lot of customers, get a lot of feedback. YC is great, it basically holds you to the fire. Because at the end, everyone's trying to come out with more funding, engage with more VCs. The only thing that the VCs want to see is just those numbers that you're having the attraction and having users using your thing. So I took a lot from YC, I thought that was really good.

Wenli: Well, thank you so much for coming to our platform and sharing with us your experience.