Founder Stories are conversations with people that have been through YC.

Kate Heddleston is founder and CEO of Opsolutely (YC S16).

Discussed: Developer Productivity; Human-Computer Interaction; Kate’s CS Degree; Academic vs. Practical Knowledge; Deciding to Do YC; Learnings from YC; Being a Female Founder; Advice to College Students; Dune.

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Craig: What is Opsolutely?

Kate: We want to do for deployments what GitHub did for code repositories–make them visible and collaborative for every member of your team while being safe and secure. Everyone should be able to deploy, no one should be scared of it, and you should be able to focus on the process that your team has for releasing code as opposed to building a whole bunch of really fragile deployment tools that are terrible to maintain and no one really knows how they work.

Craig: And where did the idea come from?

Kate: So I’m a software engineer and I have a master’s in CS. But I actually found it through a lot of the work that I do on diversity and developer productivity. My background is team sports. I played a lot of water polo growing up and then when I was done playing in college, I coached for a while. I have a lot of opinions about how teams operate and what makes a really high-functioning team. I also have a lot of opinions about leaders and leadership and the role that it plays on teams.

A couple years ago I wrote a series of blog posts about environmental factors killing diversity that largely have to deal with management and developer productivity and I was brought in to consult with a bunch of top tech companies. Oftentimes around onboarding, training, retention, diversity and developer productivity.

What I found doing a lot of that work was deployments were this really high friction point. We kind of know that from a technology perspective, but from a people perspective it’s this huge pain point. It really kills how teams function if you have something that creates an us vs. them mentality, which deployments do.

There’s usually a group of people who defends the fragile system and a group who tries to change the system. That’s a bad place to start.

Above and beyond that, most teams have to build their own in-house tooling, which means they can never get around to building the features that people really need to be productive because they’re always just barely managing to get things working. There aren’t enough DevOps engineers. There aren’t enough engineers period, much less people who know how to build truly robust deployment infrastructure. And then add on to that, usability.

So my degree in computer science had a focus in human-computer interaction, it’s an entire track. I have two degrees in human-computer interaction. Saying that knowing how to build features that make your team more productive is somehow something you can just tag on to a normal engineer’s role is not true.

I think that it became clear to me after looking at things that, you know, if GitHub is this great collaboration solution for code repositories and you’ve got collaboration solutions for metrics there clearly needs to be a collaboration platform for deployments.

Craig: Cool. So let’s talk about what your experience before Opsolutely a little. Were you mainly a consultant?

Kate: No. I was mostly just unemployed. [Laughter] That’s actually a better description. I worked at early-stage startups. I love beginnings: the first five minutes of every movie, the first chapter of every book. I wanted to start my own company.

And even after all of this consulting, it never occurred to me to make a deployments platform a company. I was actually building a cosmetics product. One of my best friends went to cosmetology school in high school and I’ve always been fascinated by how makeup works. It’s very formulaic and if you know what someone looks like, you actually can tell them how to look because formulas for beauty are deterministic. I was building something that could walk you through, “What do I look like? What do I want to look like? How do I look that way? And what do I buy to look that way?” and it had machine learning and image processing and all these different components, because it basically categorized and measured the aesthetics of your face to break it down into the major features that mattered for makeup and then gave you an illustrated version of your face. So it was pretty complicated, one day I will finish it.

And at the same time I was like, “Well, I have used all of these deployments tools, but let’s be honest, the best thing for a deployment is just a web platform with a deploy button where, under the hood, it manages all these things.” Then scripts are terrible to maintain. No one knows how to use them, no knows how to find things, and so I built a deployment platform for myself. I was like, “I wanna make it really easy to add people just like in GitHub, I wanna be able to add a collaborator to my infrastructure so that they can see things and they can actually deploy and I won’t have to train them on the system because training is really expensive.” And then some people were like, “We would use that because you built this thing based on all of this research you did while consulting.”

Then my brother gave me some of the best advice I’ve ever received, which was, “Perhaps you should focus on the products where you already have customers.” I was like, “Thank you, Russ.” Two years of him in business school and that’s what we got out of it. Well, that’s when I pivoted. I did the classic Silicon Valley pivot from cosmetics to DevOps.

Craig: [Laughter] “Annnd, we’re a dev tools company.” Okay, so you did do a graduate degree?

Kate: I did. I did my undergraduate degree in communications with the focus in human-computer interaction–Stanford has a really cool program. We basically study how people use computers, which I honestly believe is probably the more useful of my two degrees. And then I got a master’s in computer science with a focus in human-computer interaction. I knew I wanted to study computer science, so I did the coterminal there and started during my junior year.

Craig: Let’s break both of those out. Would you be able boil down the main learnings from both?

Kate: The main learning from my communication degree is that people treat computers the way they treat humans because we do not have special pathways in our brains for how we communicate with inanimate objects vs. animate objects. One of the best examples of this is how we treat dogs like humans. We anthropomorphize everything.

How your software communicates with people is hugely important because people will not change, but technology can. That has also been important for how I approach products, because I look at how people are doing things or want to do things, knowing that people don’t really change. Usually, software takes off when it maps to something that people already want to do.

It took us a long time to get to touchscreens, but everyone always kind of knew that touchscreens are more intuitive, because people like to touch things. That’s how we operate in the physical world. Even the elderly stopped needing training on it or on certain parts of it.

So that’s a big takeaway and that writing and communicating ideas is hugely important because this startup and a lot of the consulting work that I’ve done has to do with these 2000-word white papers that I wrote on my blog, that I also illustrated. Being able to write and communicate ideas is just really, really important.

Craig: Is there a common pitfall that people encounter around human-computer interaction?

Kate: The thing I see happening in the DevOps space most often is that people weigh the technology problem as being greater than the human problem, which to me is really funny, again, because technology can change but people often don’t. We don’t evolve that quickly.

They’ll think everything is a technology problem and they’ll approach everything as having a technology solution, which is one of the reasons why there’s an opening for a company like us. UX is sorely missing from the deployment space.

Another big pitfall in our space is people trying to automate away the people problems. “Well, if we just get it to the point where we can automate it so that no one ever has to deploy, code can just go live all the time safely.” And you’re like, “That’s a really ideal world, which doesn’t exist.”

Craig: What do you tell people that’ve made that mistake?

Kate: Once you realize that people just need to feel happy when they’re communicating with your product, there’s a lot of hacks that you can do in between. So for our product we want it to have a great user experience, but perfecting it takes a really long time. Right now it doesn’t have a great user experience, but I literally bring people cupcakes when things go wrong.

We need to make sure that people have a really strong sense that we are there as people so they will forgive us more when we mess up. If your brand or your company doesn’t have this feeling of being an entity people can communicate with, I think it’s harder for people to forgive you. They can just write you off because we communicate with computers like they’re humans and we don’t really like humans that we don’t feel a connection to. We just ignore them and leave.

If we feel connected to something, we’re more willing to forgive it in its early days. That’s kind of how we think about hacking things together before we actually have a product that has a truly automated, beautiful onboarding experience for our customers because it’s just not there yet. So yeah, cupcakes, in-app chat tools, and email, just give them as many excuses to forgive us as possible and love us.

Craig: What about the master’s degree? Were there separate learnings there?

Kate: It was the other side of the coin. I joke that I studied computers looking in and then I studied computers looking out. The CS degree was a lot of the fundamentals of computing–algorithms and all of the introductory courses on programming. Stanford is a research institution so there weren’t a lot of practical applications.

I didn’t actually know how to write a web application until I got out into the real world, but I did learn all about systems programming. So once I learned how to actually implement a web application, I could be like, “Systems? Oh, I know a fair amount about this,” which is important for our deployment platform, because people build systems. They don’t just build a single codebase, there are all these different moving parts. So that was really neat. I loved the theory and I loved the concepts.

I’m trying to think what the major takeaways were. I just really loved understanding how computers worked under the hood. It takes a really, really long time to learn to be a good programmer because there’s just so much to know, both about how computers work now and the history of it. But I loved that it was theoretical and that I could use a lot of it later for many years to come.

Craig: Agreed. Were there any particular courses that you could reference? I’m sure there’s tons of stuff online.

Kate: I think the introductory core is really good, so CS 106, 107, 108, and 110 classes.

CS 107 is systems programming and I had a nightmare during that class, during finals week. I had a dream that I was a struct, which is this really simplistic object. I had a dream that I was a struct and I hadn’t properly cleaned up my memory. I was out of memory and had a segfault and my brain was full and I wouldn’t be able to learn anything else for the week of finals. It was a terrible nightmare.

Craig: [Laughter] I can say without qualification that that is the nerdiest thing I’ve ever heard at YC, full stop.

Kate: [Laughter] Systems programming was a very dark time for me. And then 108 was a lot more about Object-Oriented Programming and testing and then 110 was again about systems theory. I loved that class.

Then the HCI core for my focus, which is 147 and 247. Those are really fun, because it’s a lot about how you start to build core usability and there are a lot of design classes that you have to take.

Craig: So then, what made you apply to YC?

Kate: Well, I honestly wasn’t going to. I didn’t have the greatest opinion of YC just because I only knew about it through the media. And I thought of YC as being kind of like the heart of the Silicon Valley machine and Silicon Valley is kind of sexist and racist, so I wasn’t sure how YC was gonna be any better. And I didn’t really like the whole valuations crunch that happens at Demo Day.

I kind of went in thinking I wouldn’t apply, but then I had several people recommend it and I was like, “Okay. Well, I’m gonna apply. It’ll be good practice, it’ll give me a sense for YC.” I didn’t expect to get in. I applied as solo female founder and, you know, I didn’t have many customers. I just was kind of like, “There’s no way I’m gonna get into this program, but I’m gonna see what it’s about,” because two women I knew who’d been through the program recommended it.

I was like, “Well, when you get two women saying something, I usually start listening,” which means that when I got the interview and when I went in that I wasn’t nervous at all because I was like, “Well, first off I’m never getting it in. Second off, if I get it in, I’m sure that I’m gonna say no.” And so while I sat there waiting for my interview, I really enjoyed watching everyone else run around, because it was a bunch of groups of founders who were really nervous. And some of them were wearing matching t-shirts, which I thought was very funny. It was just kind of fun to sit there and watch the fray.

Then I went in. It was a 10-minute long interview and I really enjoyed it. It was just rapid-fire questions and I had already talked to some investors and started looking into fundraising, so I’d answered a lot of them before. That night I got a call telling my I got in and I was just like, “Okay, I know that they said to be prepared with an answer,” I was like, “But I’m gonna need two days.”

I called everyone I knew who had done YC, because I hadn’t done my homework before that, thinking that I would never get in. Everyone I knew who’d gone through said, like, unanimously that it was really valuable for them and that they loved it. So I was just like, “Well. Okay. All right.” So I said yes, and I actually kind of had that same experience. I absolutely loved it. I loved the focus on your customers.

Craig: [Laughter] God damn it!

Kate: [Laughter] I know. I looked at the numbers and 13% of the founders were female, which meant that none of us was alone and that’s, like, at least a standard deviation above the percent of female founders in any other portfolio. So I was like, “Damn it. They’re not as sexist or racist as even the other investors.” So yeah, that was how I ended up applying. I was told to apply by people and, begrudgingly, listened.

One cool thing I didn’t expect is that the alumni community now is large enough that it has as much power as the YC organization does. And you can disagree and you can voice opinions, and that’s a really important part of the community. So yeah, that was that was a really fantastic part as well.

Craig: So on that note, were there other things where the reality differed from your perception?

Kate: I didn’t put enough value on the importance of having an emotional support group and it turns out that it means the difference between being pretty miserable and stressed and feeling like you might actually be able to pull this off.

Craig: And what were the most valuable things you took from YC?

Kate: One of the things I really like that they did throughout the course of the summer was help differentiate what is work from what isn’t work. So I’m in a conference right now and I know that this is not work, which is fine. I think that the biggest thing that you can do as a founder that hurts you is delude yourself into thinking that what you’re doing is work when in fact you know you’re not gonna work all the time. It’s good to just recognize what things are and are not. They did a really good job of that.

Then just staying close to the customer and doing things manually before you make them automatic. I really appreciated them saying that because there’s a lot of stuff that we have to do manually, still, and knowing that that’s an important part of the early process is great. I think that those are the biggest takeaways.

I took copious notes during the lectures and wrote down all of the advice from the partners at the beginning of the summer and all of their advice at the end of the summer. I posted it on my blog.

Craig: Cool, we can link to that. If you were to do YC again, what advice would you have for yourself?

Kate: I think I would be a little more prepared. I would have an idea of where I wanted my company to be at before I did YC. I would have a better idea of how I would utilize Demo Day. I would have a plan for what investors I wanted to talk to to and how to move them through the intro and diligence process.

So as for before YC. I think I would want to have a measurable amount of traction going into YC. I think I would want to apply YC with a goal of how much traction I wanna get while there, and these were all things that YC normally has you set up doing. But not going and trying to create that mindset.

Get a certain amount of leg work done before YC and then just focus on growth with customers or whatever growth means to you. Otherwise, for first-time founders going through the program, I think it’s a lot more exploration and figuring out what you’re doing in the first place. I’d never started a company before and even though I had worked at them, kind of just figuring out what is the core value of your product, what’s the differentiating value, and how are you gonna go to market.

These are things we thought about and it just took us a lot longer to figure some of them. We were one of the earlier companies, so we didn’t utilize the resources the same as other companies, which was great. Like, it was still really useful to me. But if I were to do it again, because I would kind of know a lot of those things, then I would prep those ahead of time and I would use YC to help me with other things: accelerating and fundraising.

Someone described YC as throwing fuel on a fire, and so if you can make that fire as big as you can before you go in, then you can get more out of it in some ways. I think it’s valuable even if you don’t approach it with that mentality. Even if you aren’t like, “Oh we’re gonna have massive growth and we’re gonna raise a lot of money at the end,” I think there’s a lot to get out of it. Just trying to understand your company and the process and how are you gonna market and why are even a company, and things like that.

Craig: Oh yeah. “We need to exist” is a foregone conclusion for most people but I agree. What about practical tips for interacting with batchmates or partners?

Kate: For batchmates I would say the batches are big enough that you should get to know some people that you find exciting more than trying to get to know everyone. Then keep in touch with them. Start to form a small community within the community and go from there. You don’t need to know everyone. And it’s cool because you can reach out to anyone if you need to, so you don’t have to be a super networker, just find some good people. Just find some good people you’re excited to talk to and who you like, because the cool thing is everyone’s going through a lot of the same stuff. Help people out and they’ll help you out back.

Tips for interacting with partners? The partners are great. I mean, they really know what they’re doing and that’s really helpful. I think any time you’re asking for help or advice, the more specific you can be, the better. But also just ask for help and advice even if it doesn’t seem that specific. I found that I would go in with questions. I didn’t really even know what I was asking and there were times when they were like, “We know what you’re asking and this is actually your question.” And I was like, “Yeah, that is.” I got some really great advice that really helped me, like, stay grounded and anchor myself so I don’t float away. Some of the best advice I got from Tim Brady, A.K.A “The nicest man in the world.”

Craig: [Laughter] Agreed.

Kate: [Laughter] Yeah, we were talking about equity and how to think about structuring it and he goes, “You know, startups pretty much never fail because someone was too generous.” And I was like, “You are so right, Tim. They don’t fail because people were too generous,” and so I just recalibrated anything I had to think about equity where I was like, “Equity, especially in the early stages, isn’t about being some sort of smart business person. Obviously, you wanna protect yourself, but I was just, like, be generous and don’t worry about it.” Within the bounds of reason, too, like YC will tell you what reasonable ranges are. But I err on the generous side, and I love it, hands down. That was great advice.

Craig: Right. So, did you feel there was any difference in a being a female founder at YC?

Kate: Well, to answer your question in a general sense, I mean, there’s always a difference between being a female founder and a non-female founder. I thought that YC was significantly better than a lot of other places. I didn’t feel as though I was treated differently, on average.

In group office hours or in any of the questions that we were asked around metrics or growth or how we’re rolling out with customers, I thought that we were treated pretty equally and pushed just as hard, and I liked that. The structure is nice because structure. The fact that YC is structured makes it more egalitarian. That kind of process is good, right, because if there’s a certain set of things that every company is focusing on, then that’s what you talk about.

It was nice having YC as an institution backing you as a female founder. So I did some fundraising meetings before YC and I had some comments where I was like, “You would never say this to any guy who walked into the room with my credentials.” But having YC as, like, this institution that backs you means that you have this pretty large, powerful, third-party organization that you can report bad behavior to and that you can also ask about bad behavior. So if an investor does something that’s sketchy or questionable, I have an organization that I can now go to, and be like, “This is weird, right? Like, I’m not being crazy?” And I think it’s really a lot more stressful when you are out there in the industry and you feel unprotected, because when you aren’t protected, that’s when you see a lot of really bad behavior.

Craig: Yeah, you feel like you have no agency, I imagine.

Kate: Yeah. There’s nowhere to go. Like, if an investor were to do something to you, what would you even do about it? So I think that’s what I really liked. There were some moments where people in the organization said things that were uneducated, but not malicious. That’s pretty par for the course, and I gave the feedback to YC. So I felt comfortable enough to actually give feedback to the organization, which is a really big deal, because most of the time you don’t. You’re like, “Why would I give any feedback here, no one’s ever gonna listen to me?”

But I felt that YC would listen, because they’ve obviously done a lot of work to improve things. And so I assume and hope that they will continue to do a lot of work to improve things, which matters, honestly, a lot more than whether or not someone says some remark where you’re like, “That’s not quite right,” you know?

The nicest thing about being a founder is that you get to keep everything that you do, that’s the way I describe it. If investors are sexist, they usually don’t talk to you, which is great because then you don’t have to talk to them. If they don’t invest in you, it’s pretty binary. They’re not in your life if they don’t invest. You don’t have to spend any time with people who are sexist if you don’t want to.

Craig: Hopefully, yeah.

Kate: The nicest thing about being a female founders is a lot of the sexist assholes don’t ever come talk to you, and a lot of the guys I know can’t figure out which ones are the assholes until too late, and then they’re stuck with someone that’s terrible, whereas I love all of my investors. They’re wonderful people, you know?

Craig: Yup. Surrounding yourself with good people makes all the difference. So two more questions. Do you have advice you would give yourself when you were just out of college?

Kate: I think that there are some things I did that I’m glad I did. I do feel bad when I see founders who are much younger than me, even like in college or right out of college, because taking time to develop a set of skills and just to kind of see how organizations work and just how people work, is important. You can’t build a great organization unless you have an opinion on how an organization should operate, which you can’t have without that experience. And founders create company culture, so I really don’t think that founders should be that young. Like, I would never work for a young founder again. I would never work for a young founder again unless they put an adult in charge, because I think a lot of the gender issues in our industry come from just people who have zero management skills and zero understanding around what it takes to build and grow a team when starting companies.

I would tell people to get experience out in the world and to mentor in their industry, too. And to kind of learn some management skills in addition to whatever core skills they’re learning if they wanna start a company.

I would also recommend just meeting people and networking, not even networking for business, but just find people that you like, because when you do start a company all of the people that I’m working with now are people who are really talented who I know and think are just wonderful people, and I wouldn’t have them otherwise. I didn’t network with any of them in the sense of, like, “I’m gonna network with you so that I’ll know you later for business.” They’re just good people that I like who are good at something. So I think that that’s really important.

Craig: Cool. Last question, what are your favorite books, podcasts, or just media in general.

Kate: I have a really hard time listening to podcasts. I don’t know why.

Craig: [Laughter] Deleted. What about books?

Kate: I mean, I read a lot of sci-fi/fantasy novels.

I usually read to escape reality. If I wanted to do anything self-help, I read a lot of blog posts. I don’t think I follow any one person in particular–just a whole bunch of different people. Normally, when I read, I just like to escape reality and read a good story, preferably set in space or a totally different world.

Ready Player One is one of the best new books out in that genre. Neil Gaiman. A lot of the famous fantasy authors Ender’s Game is a classic, Orson Scott Card. Oh, Dune. Oh my God, I quote Dune. I literally quote the book or movie almost every day.

Craig: [Laughter] That’s very impressive.

Kate: [Laughter] Just because… I don’t know. It just comes up a lot for me, “They tried. They tried and failed. No, they tried and died.” And the people are like, “Wait, what?” And I’m like, “No. I’m just kidding. No one died.”

Craig: [Laughter]

Kate: Someone was like, “Should the women in engineering, like, form a guild?,” and I was like, “Yeah. As long as we can have, like, a monopoly on baking and space-time travel, I’m in.” People were like, “What are you talking about?” I’m like, “I don’t know. I just make Dune references.”

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