From Startup CEO to Investor

Ellen Chisa, Partner, boldstart Ventures

I talked with Ellen Chisa about her startup leadership experiences and how she moved to being a partner at investment firm boldstart Ventures which invests in pre-product founders. Though this challenge is slightly different from others, I wanted to cover it because we don’t talk enough about the transition from a leadership role, especially one like CEO. I think you’ll find Ellen wise and her story enlightening.

We have mostly known each other, I think through Twitter. I don't even know when. Honestly, it's been a while that I've been following you.

Yeah, I've been following for a while and then I've definitely read some of the recent interviews you have done, but I don't know when we started following.

I'm so glad you came on. In the process of prepping for this, I learned that you also grew up in Michigan, like me.

I did. I grew up in Rochester Hills outside of Detroit.

And I grew up in Warren, which is where, for people who don't know, that's where the GM’s headquarters is. My dad was a design engineer and so we lived really close to his work. He used to ride his bike sometimes to work.

That’s very unusual for someone who worked at GM!

Yeah, my dad's an interesting dude. He designed prototypes for GM. He’s why I love tech and I love software engineers. Well, you're no longer in Michigan. At what point did you leave Michigan?

I left right after high school. I went to undergrad at a tiny engineering school called Olin College of Engineering. Michigan’s huge on first robotics and a lot of people who ended up going to Olin were first robotics participants in high school. That's out in Needham, Massachusetts. So, I left when I was 18.

You haven’t lived there since, is that correct? Or did you go back for a while?

Not really. I spent the summer there when I was 19, right after my first year of college. And then right after I left Dark, I ended up staying with my parents for a couple months just so I could see my family more during the pandemic. But that was a pretty quick three month stint, and we knew we were coming back to Massachusetts after.

Oh cool. I've lived all over the country, but I feel like I'm always a Midwesterner at heart. No matter that I haven't lived there in years, it's still inside me always.

I have the same thing. My husband makes fun of me because he thinks I like people better who are from the Midwest. And so if there is someone at a party who's from the Midwest, I will probably find them.

Then you'll go talk to them, right?

Yeah.

Thanks again for coming on. I've had another Michigander on the show so far too, Tramale Turner. It’s nice to have more folks from my home state. Can you just give us a quick little background about an introduction of yourself?

Absolutely. So I guess going from the beginning as we just learned, I grew up in Michigan and then I went to engineering school in Massachusetts. After that I worked in a variety of software roles, spent a little bit of time at Microsoft, then was a product manager at Kickstarter in New York. Had a little detour through business school, was the first employee and de facto head of product at a company called Lola, which was recently acquired by Capital One. Then founded a startup called Dark, which I think we'll talk about today, where we built a programming language that is integrated into its editor and infrastructure. Now I’m a partner at boldstart Ventures where we invest in technical founder-led companies at formation. So as early as possible. Most of what I've done there so far is in the developer tooling space, although we also do some other enterprise and SaaS investing.

Oh, very cool. I was in the developer tool space too when I was at Travis CI. I love that space.

It's a super interesting space. I feel like developer tooling has a lot of interesting technical challenges, a very opinionated user base, but then also some fun aspects from the consumer side and some of the very pragmatic enterprise type work. I think you get the best of everything.

I would agree. That's a great summation. So you founded and were CEO of Dark. How did that come about?

I always knew I loved startups. When I was an undergrad, five of my friends and I dropped out and had a startup in the edtech space. There were a lot of problems with this company. The fact that there were six of us is one, that we all had exactly the same background is another. Edtech is a really hard market. But I think that was the first time where I really got a feel for it, and was like, Oh, I want to go and get better at building software. I definitely want to make more startups.

I want to build things that have a real impact on the world. I think part of that came out of going to a brand new college. When I went to Olin, it wasn't even accredited, so I got very accustomed to selling the dream, which I think is a big part of startups.

I'd spent a lot of time in the entrepreneurial space, but hadn't been a founder yet. When I started at Lola it was actually that I was originally an EIR in an incubator called Blade. So I had been working at a project alone. I thought I was going to be going on the founder journey that time. And then we ended up deciding that it was a better fit for Blade to instead pivot the core staff into being Lola. I was there through the series B. Lola was focused on travel. One of the things I realized working on Lola was that while I personally love travel, it wasn’t a space I wanted to start a company in. My personal mission is around helping people build things, which could be through accessing capital, it could be through teaching, it can be through building tooling of various types. I knew I had to start something that aligned to that mission.

Since I like to build software, developer tooling is a pretty logical extension of that. So when it came time to think about starting something, that was the space I was most interested in. And then my co-founder Paul, had previously founded CircleCI, which you probably know from the CI space.  He had come at it from a different angle of what happens if you go from continuous deployment to not having to do it at all? Actually continuous, where as soon as you write anything it's live. We started working on ideas in that space and how to build something that actually enables everyone to be getting real time feedback as they're building software so more people could actually be writing code.

At what point do you decide we're going to turn this into an entity and how did you become the CEO of that entity?

I think there was always an intent for it to be an entity. I think for some of the specific ideas around CI/CD, Paul had obviously been thinking about them longer than I had. My thoughts were more around how we make it feasible for more people to build software and what makes for a good product that allows people to do that. So there was always the intent there for it to be an entity. In terms of role division, I think that really it's going to vary startup by startup. Especially looking at more developer tooling companies now, I think there's a period of time, usually about a year, depending on how complex the tool is, where you're building the core infrastructure and getting to something that works. To do that you have to have that cohesive architectural vision in your head, which I think is something Paul is very strong at, especially coming from a background in compilers.

Then there’s the next part. It can be very easy to make a developer tool for yourself that you enjoy using. It’s very hard to get even the first other person to adopt it. Half the conversations I have with people who have an interesting project is how do I get anyone other than me to use this for the first time? I think in an early developer tooling company the crux of the CEO role is spending the time there. So most of what I spent my time as a CEO — getting people to use it.

The first one was we hired an “engineer in residence” who came and built a big chunk of his company on top of Dark. It was a really fun process to find the right person. And then after that it was the experience of pairing with people to get them onboarded enough to use Dark before we really had any good documentation or full understanding of what people would use the platform for. And so I really gravitated towards spending the time with other developers to see what they would want to use our tooling for.

Oh wow. When did Dark get kickoff?

That would've been in the spring/summer of 2017.

Since you wanted to found a startup, being CEO was probably something considered?

Yes.

Yeah, that's what I thought. A number of people I’ve talked to hadn’t considered being a CEO. So it's interesting people who did versus who didn't.

I think part of it is that I do enjoy it. I don't know if you've ever talked to anyone about Enneagrams, but I'm a very strong Enneagram eight and so I feel much better when I have autonomy.

One form of having autonomy is sitting at the top of a hierarchy because it's very easy, once you're sitting there, to then give that autonomy away and empower other people to have it. So I feel no need to make every single decision about something. I don't like making every decision, but I feel a need to be able to have autonomy. So that was one part of being CEO.

And then I think the reason was that I'd just been in a variety of other leadership roles. Since Olin was such a small school, there were inevitably always more things to be done than there were students to do them. There were only 300 students at a time and running the full infrastructure for a college on that small student body was challenging. Or early in my career when I was working at Microsoft outside of work, I became the dean of a chapter of the Awesome Foundation. So I was accustomed to keeping track of 10 permanent trustees and our rotating cast of guest trustees.I was familiar from that standpoint and so it seemed to just be a role that I gravitated towards.

That makes sense. I just love to hear how people sort of got into it, whether they expected it or not. What was different or harder about leading a startup than you expected?

It's really interesting. There are some things you’re uniquely good at, and those are the last part of the job that you will give away. So it takes immense awareness of what those things are. I think one of the challenges is that you’re doing so many things which results in being scattered and less good at your superpowers. I can certainly say I was less good at classic product management for Dark than I was when I worked in a role where I could entirely be focused on product. Watching yourself cut corners or be worse at something that you know you are very good at is rough. 

In contrast to that, at the same time you still underrate your experience in certain areas just because it seems easy to you because you've been doing it for so long.

When you’re very good at something you will sometimes assume that it’s easy. When you think it’s easy instead of understanding the talent, you’ll assume other people on the team can pick up those things and do them the same way you would. So you have to be very aware of your own strength so you can know when you are having an unrealistic expectation of someone else, and that strength might not translate across the board. The type of thing that might feel easy to you is not going to feel easy to everyone on your team.

As a founder of a startup, you're also usually hiring people to do jobs you've never done before. I had luckily had that experience at Lola, it was really nice to have managed people in other disciplines before doing at Dark. It's certainly quite different to manage people doing roles you have not done, and that's enjoyable and challenging.

And then I think the other one is that any compromises you make with yourself - if you say, “hey, I'm going to put up with this,” it becomes something you have implicitly asked every other person on the team to put up with, too.

If you set an example where you've cut a corner and paid a little price, it's not just that you're paying a little price, you have perpetuated that little price across everyone else who works at the company.

That's so great. I don't know that I've heard somebody articulate that way before, but I love that it's paying the price that when you pay the price as the leader, you are now asking other people to pay the price. Were you aware of that when you were making that decision or was it later?

It was definitely later. I think actually our first employee at Dark, Ian Connolly, was one of the people who gave me the feedback that indicated “if you are willing to do this, it means you are setting the standard that everyone else also should be too”. I also worked with a coach at the time, Semira Rehmetulla, and she might have pointed it out too. So I think it's one of those things as a leader, you're going to constantly hear feedback from people, which is data, but at some point you have to synthesize all of that together and take the lesson from yourself about what it means for you as a leader. And so that's been something, those are definitely two people who helped me come to that realization that's changed how I lead today.

My guess is that, after, did you think about it more about the prices and gave you a different perspective to think about what I am putting up with, and also means I'm asking other people to change your mind about it.

Yeah, one of the nice things about being at a fund, especially a small VC fund, like boldstart is, there's seven of us full time, is that you're not thinking about things in the same way where it's necessarily going to be replicated across tens of thousands of people. In the best case scenario, at the end of the day it's going to be replicated against seven or maybe we grow a little bit and it's 10, but it's still a number of people you can have individual relationships with. So you can think about it differently there. For me, I'm really happy that we have a team today where if I'm excited about something I'm working on and I send out a message over the weekend, that's totally fine and everyone will understand.

No one's going to feel obligated to work because I'm working, and I like being in an environment like that. Whereas if I were thinking again about a larger scale environment, I think I would be more likely to say, Oh, I don't want to be sending some implicit signal that I expect everyone to answer me when I have a good idea on Saturday, therefore I'm going to hold them until Monday. But I feel like I lose something for myself when I hold the ideas back. And so that's one example of the kind of things I think about now.

I love that you talk about that because I think leaders all the time are sending messages that they don't understand or don't intend to send. And it's only looking back later we're like, oh wait a minute, I didn't mean to send that message accidentally by how I behaved or just naturally being myself. We don’t always see it at the moment.

I think at some point you just have to decide what's worth it or not worth it and be okay with what messages you're going to send. No one's going to be a perfect leader for everyone. You're going to have to decide what is your style of leadership and what type of people work best with your style of leadership and build a team that is effective for both of you together.

That's such a great point. When did you leave Dark?

Summer of 2020

What was hard about leaving a startup? I mean startups are in your blood, right?

Oh yes. I think the hard part is that it's in your blood. I think one really awesome thing about being a founder, especially after you've been a founder in a space for a few years, is you become such a deep discipline expert on the one specific thing you are doing and you are pushing the frontier of that thing.  I really miss the idea of waking up every morning thinking about what the next iteration of programming looks like, and what are the small details and an experience that can really drive that forward?

Not that I can't do that today, but it's very different to think about something in the abstract or have smaller experiments or talk to people about an idea and have a platform that you're experimenting on top of. I had that with Dark, I had that with Lola. So I think that's always hard for me personally. Every time I've worked on a product that got my blood that I really loved, it's taken at least six months to a year. I think this time was frankly probably two, before I felt like I had removed myself from that problem at all.

I think as a leader but especially as a founder, the passion and really caring about the space...I mean people laugh about the word passion, but it's like you really care about it. You get really invested in that problem space and the product that is working on that.

Yeah. I think the other thing is as a founder there's always something you could be working on or doing to move the business forward. So even if you're further along, there's always like you can jump in and answer support tickets or go through and kind of look at what customers are asking about. You can go think about what would be an interesting new partnership. You can try out a new feature. There's always something going on that you can very specifically plug into, where you can see if I plug into this, this will be a tangible outcome for our business.

Whereas when you're in a phase of transition, you're only accountable to yourself. There aren't necessarily tasks that come up immediately. There's a lot more work that is about the arc of what are you trying to do in the long run and why, and there are things you can reflect on. But it's not the same as this customer had a question, I answered it. I definitely missed that little bit of linear task doing that you can always find as a founder.

That makes a lot of sense. How did you decide to become a VC?

This was actually really nice. I had been an active angel investor before. I enjoy figuring out how people can make more interesting things in the world and access to capital is one way to do that. Angel investing is one way to give people access to capital. So I'd been doing it from that standpoint. And boldstart had been one of the investors in Dark, so I'd known Ed and Eliot, Shomik and Natalie and the rest of the team really well already. They were people who I liked and trusted a lot, which was very important to me. When we started talking about the role, we really framed it in terms of, okay, maybe I'll start another company. Like I said, it takes a long time for the last company to get out of your blood.

I didn't know how long that would be. So I was like, okay, maybe I will get excited about another space or something adjacent or something different, and if not, what I've been doing is mostly helping with early adoption of developer tooling and refinement of product based on that. The boldstart portfolio can benefit from that. So I could spend a lot of time working with the existing founders in the portfolio. And then investing was also interesting because I had been doing that angel investing. So when we originally carved out my role, we carved it out as the Founder in Residence role to give me the freedom to work across those three spaces and land on the right thing.

What we found over time was since we're a small fund, I can still do pieces of the other parts, definitely not starting something new, but I can still help all of the companies in the portfolio and then I can also find and invest and serve on the boards of new companies and work with founders who are in this space. It was a very seamless transition.

Was that something you'd ever really considered before moving full time into venture capital? Was that something that had been an aspiration?

It definitely hadn't been an aspiration. I would say it was definitely something that was on the table. I think one nice thing about being a venture-backed founder is you are exposed to venture capital. You meet a lot of really smart and interesting people who are investors. So I think it's hard to not consider it at some point as an option. But I like to think about all the different careers you could do. So similarly I've thought about how much fun it would be to get a PhD in technology and operations management, which is basically what Harvard calls the process and operations flow. So how do you get cranberries out of a bog to a store? And I find logistics really interesting and so it had certainly been something I thought could be interesting but wasn't one of the people... I have friends who have known they wanted to be investors for their entire careers. And I definitely wasn't in that bucket.

Yeah, got it. I'm always interested in how people, especially in leadership roles proceed throughout their career, how they make those decisions about what's next.

I tend to think of it in arcs. When I started Dark it was such a big idea that you have to be willing to commit a decade to. And the same thing I think that’s nice about venture is when you commit to backing an early stage company, you're assuming they're going on this 10 year journey and you're going on this 10 year journey with them. I spent a lot of time in my transition period thinking about what is worthy of the next 10 years of my career.

That resonates, as I was coming out of my role at Travis, I had a friend who was also coming out of a role. We both pondered what was next. They’re now a CEO of a startup in the dev tool space. So the ten year arc makes a lot of sense. If you want to found a company and really commit to something, that's what it takes. This is not a one year venture to found a company.

You’re nowhere in a year! A year into Dark, we just started having our first user. which If you're building a SaaS company or you have something you can prototype or Wizard of Oz, it can go faster than that. Lola, I was a travel agent two months in, because there's so many other chat platforms you can build on top of. But with Dark a year in, we were just starting to see what real people using dark looked like.

How is your role now different from being a CEO? And what do you like about the role now versus when being a CEO?

When you're a CEO, everything falls on you. At the end of the day, whatever has gone wrong with the company, at some point it will become your responsibility unless someone else deals with it. This means the hardest things tend to come to you or the things that just fall through the cracks and aren't technically someone else's responsibility. So there's that pressure where at the end of the day, there's no one else that will really go to.

As a VC, you are there for the founders you're working with, but at the end of the day it's their company and they're going to make the final call on what they're going to do. You're there as a sounding board to provide resources or, as my partner Eliot calls it, to provide options and leverage. But at the end of the day you have the phone call, you have that conversation, you maybe jump in the trenches with them for a little bit, but at the end of the day, it's not the same for you as it is for them.

On the other hand, with both of them, there's definitely a balance of how do you keep your thinking at a high enough level and make sure you're tracking towards the right thing. When you think about quarters or years or what set of milestones you're looking at achieving next, you have to maintain that higher level context. Both of them are jobs where you can’t just say, oh, I'm going to do this task. You can't measure your success as “I shipped this thing.” Certainly the beginning of shipping things matters, but you also have to ship the right things. And so I think that focus on what really matters is similar between the two.

What do you feel like you brought as a CEO? What kind of experiences did you bring to the role that has informed the way you do your work now?

One thing I really missed as the CEO was feeling like I had someone else who fully kept the state of my business in their head with me. I wanted someone who could reflect back on what they heard repeatedly over time or point out when I had gotten stuck or in a loop or something. And so for that, I truly try really hard every time I'm with a founder to be able to say, Okay, everything else that might be going on, there might be new deals happening, there might be another company that's having a problem right now or a good thing happening right now. I try to put all of that to the side when I'm interacting with a founder, and think about it from their context and everything we’ve talked about before.

And that's not to say I can't think about the rest of the landscape that might be useful to them, but it's sort of I think about the entire landscape with the filter that is appropriate to them on. So I would try not to end up in a state where I'm giving short shrift of my time because I'm actually thinking about some other deal I wanted to get done.

Sounds like you're really trying to immerse yourself in what's going on for them and the problems that they're facing externally in the market or internally at the company or whatever it is. You try to really immerse yourself in their experience.

Yeah, exactly.

What advice might you have for first time leaders?

I don't think people talk very often about the difference between management and leadership. When people tend to get their first management roles, it's as a frontline manager. If you're managing a small team of four to eight people who are doing the job that you used to do, that skill is very much about building the management discipline as a skill. But I think it's quite removed from leadership as a skill. Simply because depending on the size of the company, often frontline managers don't have that much autonomy to change the overall direction.

I think oftentimes first time managers frankly often end up managing teams of people who either didn't want to be managers or didn't like being managers and don't necessarily always have the ability to manage their manager. If you're a director or a manager of managers, you're managing people who have some empathy for what that relationship is and their role in it. People tend to think, “I have to learn how to be a leader now that I'm a manager”. I would say instead to pause at that moment in your career and think about the manager stage before you think about the leader stage.

I love that. I don't think people talk about the difference between manager and leader enough. Management and leadership are not the same. We collapse the two and they're really quite different disciplines.

Yes. When I think about first time leaders, I actually think one of the nice things about leadership is you can lead without being given any formal authority to do so at any point in your career. I tend to think of that as saying, “okay, what is my role in this system and what is the ideal outcome I'm going for, and how can I do that and how can I help the people around me do that?” I think a big part of it is also self-management in a lot of ways. I really like the book, The 15 Commitments of Conscious Leadership. That would be my recommendation to someone who is thinking about how they can be more of a leader, regardless of where they are in their career. If you start with yourself, it can really help you build the skill sets and discipline that will help you lead in a more formal position of authority. That one is just much more about how you interact with your colleagues, or maybe not colleagues, but in whatever scenario or group you're collaborating with.

I have not heard of that book, but self-management is so important for leaders. Is there something you took from that book that you really live today?

Yeah, there's a few. What I mentioned earlier about knowing what you're good at, definitely relates to one of the topics in that book. The other one I really take is this idea of if you're acting from above the line or below the line. One is more of an expansive mindset and one is more contracted. So if you're above the line, you feel like you're an agent and you have control over what you're doing or you are coaching someone else and trying to help them get somewhere in a helpful way or you are challenging someone else to try to make their idea better. But in either way, you are a protagonist who is playing a role in contributing within a system.

When you go below the line, you feel like a victim or a villain. “Why is this happening to me? Why did my boss assign me this work?” Would be a classic victim type of mindset, or “why is this customer being unreasonable?” A villain, which is you might be antagonizing people or just always sending really negative feedback. Or a hero, which this is the one I'm prone to on my bad days. I think a lot of founder type personalities go to hero and want to step in and save the day, without realizing that that pressure you feel where you're like, oh, I'm here and I have to save the day again, is actually a negative energy, not a positive one. I think we like to think of heroes as always being positive, but in that particular case it's not. But I think just having that internal barometer can really change how you interact at work. It can change how you're interacting with others, I think can change what you're able to accomplish.

I love that you brought up the idea that even leaders can feel like victims or feel like they're at the whims of other people. I think people who have not been in leadership roles sometimes see leaders as all powerful. I think that there's a lot of times when leaders feel really disempowered or victims to circumstances.

Yeah, 100 percent. I think the challenge for the leader is learning you're not going to do your best work when you feel like you're a victim to the circumstance. You have to say, well here's the circumstance I'm in. Where do I go from here? You can't dwell on, oh, these bad things are happening to me as a leader. Even though frequently they do. You can have funding fall through at the last minute. You can have a key employee quit. You can have something go wrong in your personal life at the same time something is happening at work. There's so many things that can go wrong, but all you can really do is say, yes, this is the circumstance and how it is. What am I going to do now? The faster you can get yourself into that loop instead of a victim feeling, the more effective you tend to be.

My dad always talks about it as your assets in access become your liability. So maybe being a hero and solving things is great, but that there's also when is it too much maybe?

Yes, I totally agree with that. I think your strengths are also your weaknesses for sure. One of mine is like I am very happy to work on anything autonomously. I enjoy having autonomy and I want to get it done. The flip side of that is I am bad at roles in process, and if you try to get me to follow a rule, and I think it's stupid, I probably won't. Which makes me a very bad employee in very many circumstances. But it goes with my strength. I can't have one without having the other.

Yeah, for sure. So you spend a lot of time now coaching or mentoring your folks? Or how much role does that play in your work?

When you are an investor, you have new deals that you're working on where you always want to be finding new and exciting things that are happening and other people that you want to work with. So there's some amount of that. But once you've decided you want to work with someone, again, it's a 10 year journey. One of the things that compounds is investing in that relationship and helping that person. Most of the founders I work with are first time founders, and helping them go through that transition from mostly engineers. So from individual engineer or engineering manager into engineering leader and company leader.

Are there any patterns you notice in those folks making that leap or is it all over the board and in their journey?

Certainly the exact things that happen are all over the board and they will vary person by person. Startups fundamentally have a huge amount of unknowns. There's a lot you can't control. You can have a great idea that seems like it's for the right market at the right time and the company still fails. Happens all the time. And so you see a lot of people, especially first time founders, going back to what's comfortable or something they can control. So maybe that's like they want to just get back into the code base and write a bunch more code, because that's something they've been good at before.

Or it could be picking a number that might not actually be the right proxy, but saying, oh, if I hit 1 million of ARR, everything will work. I'm just going to brute force our way to 1 million of ARR. Which isn't necessarily always the answer, depending on the space and the market and what you're trying to achieve and how you want to set the company up for the long run. And so I think that feeling of uncertainty causes a reversion to “what can I actually control” rather than just accepting the ambiguity that comes with startups. That pattern definitely comes up pretty frequently.

How do you advise leaders to stop that behavior or to recognize that's what they're doing?

When people just say, this is what I'm doing I ask them, “How will you know if this works? What do you think the impact of this will be?” I just try to keep people coming back to “why am I?”... Not activity for the sake of activity, but outcome and goals and how they'll know if things are working or not. It's easy to spend a lot of time and do a lot of interesting work without it really tracking towards where you want to go at the end of the day.

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