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Ellen Chisa - Partner at Boldstart Ventures Episode 87

Ellen Chisa - Partner at Boldstart Ventures

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Ellen Chisa:

Understand that you are probably unfairly good at something, and take the time to figure out what it is, and you're probably discounting it because the things that we were unfairly good at look like, feel and look easy to us.

Jack Bridger:

Hi, everyone. You're listening to Scaling Dev Tools. I'm joined today by Ellen Chiesa. Ellen is one of my most requested guests and is a partner of Boldstar Ventures, a VC firm focused on enterprise companies at inception, including developer tooling and infrastructure. They invested in the likes of Snyk, as well as Zooplo, who's been on the show.

Jack Bridger:

Prior to Boldstar, Ellen co founded dark along with the co founder of CircleCI. Dark is an integrated programming language editor and pass that has been very influential in the developer tools ecosystem. Ellen has a background in product development at various companies including Microsoft, Lola, and Kickstarter, and also sits on the board of Liveblocks. Ellen, thanks so much for joining.

Ellen Chisa:

Thanks for having me. I'm bummed that we're missing each other in London, but at least we get to do this.

Jack Bridger:

Yes. Yeah. We have kind of swapped sides of the Atlantic. So yeah. So one of the things that we were talking about before is how many SDKs should a startup have?

Ellen Chisa:

I mean, if you want the the spicy answer, the answer is 1 and always 1. But, of course, it's gonna depend on what you think of as being a startup. And so for me, when founders are saying, like, oh, I built this great tool, should I have made my SDK for Python? Should I make a bunch of other ones because that'll, like, juice my user numbers? I mean, the answer is usually just keep doing the one thing you are doing and do it well and reduce your whole speed as much as possible by keeping it narrow.

Ellen Chisa:

So you can keep iterating and making an experience better and better for those users and just wait until people are banging you down your door for the next one. Don't think of it as being something like, okay. Well, I shipped Python next week. I shipped an SDK for Ruby or something like that.

Jack Bridger:

Yeah. That that makes sense. I I have to say when we spoke about this, I found it interesting because I'd kind of committed the cardinal sin already where I'd emailed someone and they said, oh, no. We only we use Python, so you don't have that. And then I was like, the yeah.

Jack Bridger:

We'll build a Python SDK. And so how, how do you get past that kind of like temptation of just,

Ellen Chisa:

this is actually a really great meta question. And I think what it really comes down to is at some point you have to decide who you're building for and build for them. And so if you're saying like, I guess in your case, you're, you're building tooling around, video streaming. You can kind of say like, which developers who are building, you need something for video stream am I focused in on? And are the people who are already using Python or are they, what did you build the first version in again?

Jack Bridger:

JavaScript.

Ellen Chisa:

JavaScript. Yes. Or are they JavaScript people? And so if you said, like, hey, I'm building for JavaScript people. There are certainly enough JavaScript people in the world that you should be able to find a few who are excited about using it, And maybe you just got bad luck with the first person's a Python person, or they just happen to see it.

Ellen Chisa:

But the limiting factor right now shouldn't be that there aren't enough JavaScript people in the world.

Jack Bridger:

Yeah. I re I really like the way you you put that actually. And before when we were chatting, it's like, yeah. Clearly, that's not the problem.

Ellen Chisa:

It is really tempting though because, like, I think as founders and as builders, whenever someone comes in and is like, oh, I wanna use your thing. I just need this one thing. You you wanna do them the favor. You wanna make it so they can use it. And it emotionally can feel like the right choice and emotionally can feel like, oh, I'm being responsive to my to my users, but they aren't your users yet until they're actually using it.

Ellen Chisa:

And so that's like being responsive to your potential future users at the expense of the users you have today.

Jack Bridger:

Yeah. That's that's that's something that we were speaking about as well. It's like you were talking about people that wanted, like, esoteric features that didn't really matter and, like, it's so tempting to just, yeah, help everyone and try and solve every problem.

Ellen Chisa:

Yeah. I think this is, like, this is true if you're building a developer tool. This is also true no matter what you're building. At the end of the day, you only have so much time and so much, like, space, surface area, and your product for what you can do. And so every time you say yes to something, you are implicitly saying no to a bunch of other things.

Ellen Chisa:

And so I think people sometimes will, like, trick themselves into being like, oh, I just, like, always wanna be a yes person. I always wanna be helpful. I always wanna be, like, going in this forward direction. And don't take into account that by saying yes, they're in fact also saying no a 100 times, because they're not saying it out loud. And if you kind of force yourself to say, okay, when I do this, this means I'm not doing these other a 100 things on my to do list.

Ellen Chisa:

That makes it a little bit more clear what the trade off is, and it doesn't feel as good to say yes.

Jack Bridger:

Yeah. And how how do you know if it's like a a yes or a no?

Ellen Chisa:

I mean, I think that's that's hard. I think that's kinda, building things is hard enough that I think that's kind of why we ended up with PMs is everyone was like, okay, well, we can't just build everything. So we're gonna like employ this entire class of people who decide if we should build something or not. But I actually, I think the closer you can get decisions, people are actually building the better. And from that standpoint, I tend to think of it as what's the what's gonna have the highest impact.

Ellen Chisa:

Some people will say like, you should have 1 north star metric that you're going towards, and that's the thing you're trying to drive. And so everything you're looking at, you evaluate, does this hit my north star metric or not? Sometimes for me, I'll use the Eisenhower matrix, which is like, is this important and is it urgent? And if it's important and urgent, I'm definitely going to do it. If it's important, I'm going to do it.

Ellen Chisa:

It's urgent. I might do it. And if it's not urgent and not important, I'm definitely not going to do it. So that's another way of looking at it. But at the end of the day, I think for every single thing I build or talk to someone about building, I think if we build this and it's successful, like, what do I expect to happen after?

Ellen Chisa:

And I should sort of have the hypothesis in mind at the time of building of what the impact is going to be. And if I don't have that, that probably isn't something I should build until I know what that hypothesis is.

Jack Bridger:

And what do you do when you don't know the what the hypothesis is?

Ellen Chisa:

I make one. So I guess, like, in your in this case of I have a JavaScript SDK, should I build a Python SDK? Say, I don't think this is the case, but pretend you'd have the JavaScript SDK for 3 months and no one's been using it. And you're kind of like, you know what? I've kind of, I think I've figured out that there are other better solutions for JavaScript users in this space.

Ellen Chisa:

But I keep hearing from these Python people who really want an SDK. And I know I haven't gotten, say it's no users or say it's 5 users of this, like, original thing in 3 months. I'm gonna do the work and I'm gonna build the Python one. And if I see 10 users in the 1st week, or if I email everyone who's asked me about the Python one and they all sign up and start using it on day 1, like, that's enough of a success for me to go, oh, okay. I'm gonna deprecate this JavaScript SDK.

Ellen Chisa:

I'm not gonna worry about that anymore. We're, like, all in on Python. And so, like, that's one one way I would potentially think about it. Another one could be in even the same scenario, you could just say like, oh, I think I've tapped out the JavaScript market. I've been working on my products for the last 4 years.

Ellen Chisa:

And I am the defacto answer for video processing for JavaScript developers. And I feel like there's not much to be gained and, like, there's no more SEO I can do. There's no more events I can go to. I feel like I'm really limited in the JavaScript space. I wanna move over and, like, open up, and I see there's, like, a lot of demand for similar problems in Python.

Ellen Chisa:

And, like, now is the time for that. And I'm expecting that this will expand my user base in a way that shipping the next JavaScript feature wouldn't.

Jack Bridger:

Yeah. That that makes that makes sense. That you're kind of, you're exhausting that well before you move on to the next one and, like, start trying to

Ellen Chisa:

And it's sort of like is it it's a diminishing returns thing. Like, I'm not saying you gotta get every single JavaScript to develop Brian Earth before you decide to do something for Python, but I definitely see far more founders go the other way where they're like, okay, I'll build the JavaScript, Python, I'll build the Ruby, I'll build something for Rust, I'll build something for Go, and wanting to cover the whole landscape right off the bat. And so I tend to push people in the opposite direction. Just focus on one thing and do the one thing well.

Jack Bridger:

And I guess it's like it's kind of almost like a trick where it's like, oh, you could just build an SDK, and that might not take that long. You know, you could get a first version out, like, depending on the product, like, pretty fast. There's even tools that generate them. Right? But then it's like, for me, I I probably know who most of I I know most of the things that JavaScript developers read, and I know who's influential, and I know, like, the culture of the JavaScript world.

Jack Bridger:

But then if it was if we wanted to build a Rust SDK, I don't know any of those things. And all like, I feel like it yeah. That must be part of it as well of, like, stretching yourself.

Ellen Chisa:

Yeah. That's definitely true. And I think that's something a lot of people who haven't spent much time in the dev tools world miss is, like, developers are not a monolith at all. And, like like, exactly what you're saying. Like, different communities have different norms and different ways they think about the products, and they have different tools they're already using.

Ellen Chisa:

And so you're you're kind of fitting into a different tool stack depending on what community you're working with. I think that's very important to keep in mind that it might not just not be just making an SDK. There might be a lot under the hood to really get that to take off.

Jack Bridger:

And when you were talking about kind of having the north star, could you give, some examples of like, what kind of things might be a good north star?

Ellen Chisa:

Yeah. I think we got to this when I was thinking about like red flags and developer tooling companies. And one is definitely like, oh, I just need one more SDK. Another one, like I've definitely fallen prey to this is I think we tend to look at a lot of vanity metrics and developer tooling. And so like, it's very tempting to be like, oh, we have so many, like so many developers signed up.

Ellen Chisa:

We have this many accounts. And at the end of the day, the number of developer accounts you have, or the number of stars you have in GitHub doesn't really matter. All that really matters is developers who are actually using your product and getting value out of it on, I would say a day to day basis. Obviously, there's like some nuance there where if you're in the workplace, maybe you're seeing daily active users between Monday Friday and like a little bit of a drop on the weekend when people aren't at their day job. Like, that's fine.

Ellen Chisa:

But looking at regular usage and regular value accrual to developer wanting to come back and do it again, is something that I think is definitely a very good north star. Another one you mentioned at the beginning, my background's from consumer products, and I think there's actually a lot of overlap with consumer metrics and developer metrics. And so much like every time you buy a new product, they usually say like, hey, share your discount code with your friends. So they get $20 off on this thing and they wanna see that referral number go up and you bringing more and more people in. The same thing is true in developer tooling, where you definitely want to see people saying, oh, I started using this.

Ellen Chisa:

It's making me so much more productive. I wanna tell my other 5 friends about this tool as well. And you wanna see like that same sort of, barrel loop that you would see in a consumer product.

Jack Bridger:

Yeah. Are there any kind of limits in to that? Like, is it like, are there differences between consumers and developers or is it?

Ellen Chisa:

Yeah, definitely. I would say that with consumer products, you're usually thinking about a specific purchase point where you're either like subscribing to a software application or like with direct to consumer stuff, you're buying a physical good that you consume. And that's the primary revenue driver. I would say with developer tooling businesses more often, you're not thinking about every single developer pays me $10 a month. Like there can be cases where that's true, but more often than not, I see the long term business models for developer tooling companies lean much more enterprise based where at the end of the day, maybe there's an overlap with the security team, like, sneak obviously being an overlap between developer and security oriented things.

Ellen Chisa:

There's an overlap with, like, the CIO's office. And so there's some reason for a large company to be writing a, like a 6 figure or a 5 figure contract to the company that isn't just $10 per developer on my team per month. It might have something more to do with tokens or with credits or with some sort of usage based pricing.

Jack Bridger:

Is there something that's clear at the beginning when you're starting out? Like, I don't know. It was like dark. Were you thinking about, like, what does this overlap with? Like, is it a CIO thing?

Jack Bridger:

Is it like a kind of Yeah. I mean, it's

Ellen Chisa:

just, you're really getting me to hit all of the things that I feel like we all do and then go, Oh, shouldn't have done that one.

Jack Bridger:

I

Ellen Chisa:

know it's no, it's great. I feel like another common one I see with developer drilling companies is we all, like, we all know as developers that we pay for hosting and it's like, what are the things we're like, we're totally happy to pay for infrastructure. Like, oh, yes. I'm paying for my cloud computers. That's fine.

Ellen Chisa:

And so I think at the beginning of dark, I was very much like, oh, great. In the, like, super long run after dark has fully replaced AWS, everyone will be paying us for infrastructure. But like, if you think about how long it's gonna take a business to replace something like AWS, like that's a very long time. And that's a very deep relationship to overcome because every software company already has a big cloud contracts that they're happy using. And so I would definitely say I wouldn't I wouldn't think of it off the bat as being like, hey, we're just gonna charge for infrastructure.

Ellen Chisa:

I would think of it much more as like, what are people no longer having to do because they have our tool? Like, what is the pain that they're avoiding because we exist?

Jack Bridger:

What what are, like, good examples of, like, those things?

Ellen Chisa:

I mean, I think I hate going to these because these are all like the super canonical ones, but obviously like Twilio before that to integrate with a telecommunications provider, like that was a huge hassle. Stripe, same thing with finance. I don't actually know if there's been one in the travel space yet, but integrating with, the GDS systems for the back end of the travel industry, like the Amadeus's and the Savers of the world is actually quite difficult. I think I wouldn't work in the travel space again, partially for that reason.

Jack Bridger:

Those are for like looking up, like flights or something

Ellen Chisa:

like this. Yeah. Like the hotels. Yeah. Yeah.

Ellen Chisa:

And then booking them after you've looked them up And, like, ITA was another one that was acquired by Google, and that's what Google Flights is powered by. I don't know if anyone has tried to make a new developer friendly version of that infrastructure. I don't know if that market would be large enough, but those are the sorts of things where I look at it and go like, oh, yeah. There's like stuff out there that's still really painful to do as a developer. And so, like, there are interesting abstractions to be built there.

Jack Bridger:

Does it have to be like this kind of complex? I guess those make the best businesses when it's like super complex.

Ellen Chisa:

I don't know if it has to be super complex, but I would say super important and super painful. Like, it has to be, like, people have to be very unsatisfied with the way they are doing it today, and they have to be like wanting to look and find a better solution for

Jack Bridger:

that. Yeah. And how how does it work if like, you know, for instance, like, say like Zoopla or something like, so do you remember like the pain point that you were like excited about? Like,

Ellen Chisa:

Yeah. If you think about it, well, I'm like a big API person. I think the entire world is going towards APIs. I think that's even more true in our current era where if you think about people are gonna have agents of some sort taking actions autonomously, regardless of how high b people are about AI or not. I think if you think that might happen, I think APIs are a great way to encourage more automation across the board.

Ellen Chisa:

I think they're a great way to encourage more structured data. And so when I think about Zoopilo, it was very much that the existing set of API gateway and infrastructure companies, we're very enterprise focused, but we're very much like, okay, there's no, like, sign up and do it today button. It's like you're going to call and you're going to talk to a salesperson and you're gonna have a demo. And there was a big gap in the market for a gateway where you had full programmability. You could build whatever features you were wanted on top of it.

Ellen Chisa:

You didn't have to adopt the whole thing out of the box. You could say, like, okay. I'm gonna start with just rate limiting, or I'm gonna start with, like, I wanna add this one particular feature to it. And so I think the, like, level of configurability and ease of getting started as an individual developer really stood out to me.

Jack Bridger:

Yeah. So it's like, it's not it can be, like, the technology and actually, like, building the thing, but it could also be, like, the business model, like, how it set up in, like, in that sense of, like because sounds like a lot of the pain was just that you couldn't necessarily access it as a developer.

Ellen Chisa:

Yeah. That's definitely a case. And then anything about other examples or like live blocks you mentioned at the beginning, building collaboration features into a product was something everyone was kind of doing from scratch. It was actually something we built in dark for dark. And like, I, I believe that every product is something that every software product is something that multiple people are going to be kind of using and acting on the same data or needing to work together in some way.

Ellen Chisa:

Like, anything that's on the Internet, anything that's hosted, you definitely gonna have to work with other people. And all of us rebuilding that same infrastructure over and over again just doesn't make sense. Like, that's a table stakes feature that we should all be able to use, and stay focused on, like, our specific end users and the business value we can provide for them.

Jack Bridger:

So when you have this kind of painful problem, how do you think that DevTools can learn from consumer facing companies in in their marketing?

Ellen Chisa:

Yeah. This is also something I think is very interesting. We talked about it a little bit before with like developers using something and then referring other people to it is very similar to consumer virality. I also think there's something about the, the level of taste and kind of the set of adopters we come into a product over time. And I think most developer tools, like you'll get a couple influential people who use them early on in those influential people, some of them end up getting hired to do DevRel, and some of them are just people who, like, are interested in people who have completely different jobs, who are, connoisseurs of tooling, will then influence other people to use those as well and help lend to their credibility to a product.

Ellen Chisa:

And I think it's the very similar to consumer models. And I think it's because you are very much appealing to an individual. And I think it's also because you are very much appealing to a sense of identity. And so I think a lot of consumer products, it's like, oh, if you buy this kind of shoe, it says this about you as a runner. Like you're not out there wearing VaporFly's.

Ellen Chisa:

If you're like the casual jogger doing a 5 ks once a week, you're wearing VaporFly's of like, you wanna be fast in your race. And I think that's the same way developer tools feel. It's like if I think about things like, would we consider Raycast to like, I don't know if I would consider Raycast a developer tool or if I would consider it a SaaS application. But when you think about that, it's kind of saying you're the person who cares about optimizing your desktop and optimizing your workflow and being able to fully customize it. And I think that's like the sort of mindset that would appeal to a lot of developers or like Obsidian.

Ellen Chisa:

You're saying, I care about my software being more open. And so, like, it definitely says something different about you if you're an Obsidian user who's writing your own plugins than if you're say a Notion user. And so I think a lot of developer tools have the same brand and feeling associated with them and the same identity creation that consumer products do as well. And so I think it's important to be mindful of that. On one hand, you have this very pragmatic, this is the pain I'm overcoming, and this is why.

Ellen Chisa:

And on the other hand, you have like this aesthetic brand. This is what it's saying about someone when they're a user of our product, and this is what message they're conveying outwards to people when they're referring people to our tool.

Jack Bridger:

And, like, how do you if you're a small start up, how do you make sure that you encourage an identity or, like, how do you go about that? I feel, you know, if you're not Raycast, you're starting from day 1, how do you? Yeah.

Ellen Chisa:

I honestly think this is like one of the hardest things to teach. Like, I think this is something that very authentically comes from a founder. Like, at the end of the day, when you're building a product, when you're building a company, your company's gonna feel like you. This is like another painful thing I think about being a founder, is whatever you think your flaws are as a person, you will see them reflected back to you in a, like, a 1000 fold in, like, a much worse way than you thought. And so, like, I don't know if there's really any any way around that.

Ellen Chisa:

And so I think the easiest way to get that out there and get that the ethos is, like, being out there with your product. Like, I think another, problem I seek come up sometimes is founders saying like, oh, I built it, and, like, I wanna raise VCs or someone like, I can hire a salesperson and they'll sell it. And, like, that's just not how things get adopted most of the time. At the end of the day, like, you, the maker of the thing, care the most about it. And so maybe you're talking about that online.

Ellen Chisa:

Maybe you're having a podcast and that gets people to hear about it. Maybe you're going into, like, every meetup on the topic because you're excited to talk to other people with the same problem. But at the end of the day, however you authentically talk about the thing you've built, like, that's what's gonna make that, like, brand feeling around it.

Jack Bridger:

It's really interesting to hear you say this because it's kind of how I've been thinking about it as with the people that I interview. It's like, seems like ultimately when you drill down to, like, why is your company good at this thing? It's usually because the founder is obsessed with that.

Ellen Chisa:

Yeah. For sure. Like, when I think about Josh Twisted Zupplo, I think about someone who's obsessed and made his cofounder. Like, people who are obsessed with a great developer experience, who've been thinking about that for a decade of their careers. Or when I think about Steven and Liveblocks and Guillaume, they both work together on Envision, which is a design tool.

Ellen Chisa:

And so, like, they perfectly married good developer abstractions with, like, their design engineers, I think are the best of anywhere. If you look at, like, every blog post they write, the, like, amount of craft that goes into it and, like, the quality if you're just, like, the visual experience of looking at it is it's unparalleled. And, like, I don't know. That's not something I'm good at. Like, I can barely like, I know it when I see it, but I could never make it happen the way that they can.

Ellen Chisa:

And, like, I love seeing founders who are spiky like that, who have that one thing that they're amazing at, and it comes through in their product, and it comes through in all their work, and it comes through in their team, and I I love that consistency.

Jack Bridger:

Yeah. It's it's it's pretty amazing. I I'm wondering what the kind of, like, the lesson is, like, where we can, like okay. So how do we figure out what you know, because we we can't obviously be someone else. So it's like Oh.

Jack Bridger:

How do we yeah. I know. I was just trying to bring it back to, like, from the deterministic, like, okay. You you must be good. You must be great.

Ellen Chisa:

No. I think you I think it's that you should understand that you are probably unfairly good at something and take the time to secure out what it is. And you're probably discounting it because the things that we were unfairly good at look like feel and look easy to us.

Jack Bridger:

That's so true.

Ellen Chisa:

And so I think it's kinda like, like it's not cheating. Like use that to your advantage with your, like with your tool as much as you can. Yeah. Mine was very much like, I love thinking about one workflow. I'm thinking about one example.

Ellen Chisa:

And so, like, there's a 10 minute demo of me building an office sign in application in dark that we use to watch.

Jack Bridger:

I was watching this before the show.

Ellen Chisa:

Yeah. That didn't know.

Jack Bridger:

One take.

Ellen Chisa:

I didn't wanna take. That's, like, very much my style. It also was probably best on the first take. I don't know if that one was, like, one where it was definitely best at the beginning, but, like, I just did that in every single meeting with people for, like, a year before I got to that. And like, I would like watch and see how people reacted and see, like, what moments people really needed to have hid to understand it.

Ellen Chisa:

That was fun. That was so much fun for me. And so, like, I feel like that was like a little bit of an unfair thing is like, you can make a really cool demo if you love showing what you're building to someone every day, and you love, like, slightly refining the script to try to get, like, maximum, like, maximum dopamine hit out of watching someone else react to it. I remember some good or bad things about me, but it was really fun.

Jack Bridger:

Yeah. That that's, that's amazing. And how how did you figure out? Was it just like a you do you remember, like, thinking, oh, I'm good at this? Like, was it?

Ellen Chisa:

No. I remember thinking, oh, this is terrible. Half the people, like, most of the people I talk to are much software engineers than I am, and they're asking me these questions that I, like, don't necessarily know the answers to because they would just be coming from, like, a different world view or a different set of lived experiences as a developer. And so I, like, I learned a lot from every single person I talked to, and so I guess maybe the thing I was good at was kinda going through that and not mind being embarrassed a lot of the time.

Jack Bridger:

That's a very good trait. That's a really, really good trait. Yeah. That makes sense. And then, how were you able to, like, kind of when well, I guess you you did realize that that was, like, a working way.

Jack Bridger:

Like, how did you kind of bring that user as, like, to your to your advantage?

Ellen Chisa:

I did a lot, like, I'm not sure if this is answering exactly what you asked, but it was, I did a lot of pair programming with people. So like that demo is the standalone version, but apart from that demo, the thing that existed kind of simultaneous or like contemporary contemporaneously with that was I would like get on the phone with someone and be like, what do you wanna build? And then we would pair them hands on keyboard to build in dark together.

Jack Bridger:

Which I guess taught you a ton of like how they would use it.

Ellen Chisa:

Yeah. It taught me a lot of, like, what do they wanna build based on what we've put into the universe, what do they think they should be trying to build here? It taught me a lot about how people had different styles for how they wanted to, like, think about their application, if they wanted to start from a template, or if they had, like, this thing they always built in. Was it, like, a coding question or was this specific demo application they liked? It taught me a ton about that.

Ellen Chisa:

It taught me a ton about usability and ergonomics and, like, whenever someone would like, the editor in dark was structured, at first. And, like, every time someone could not deal with structured editor, that was really interesting. It definitely showed me that people who loved dark were either relatively inexperienced programmers who are just excited to try something out and, like, the structured editor really supported them, or people who tried every single new tool and thus were, like, very mentally flexible. And the people who struggled the most were definitely people who were, like, I've been an X developer for the last 15 years, and I am amazing at it. And, like, those people I was pulling way too far out of their world to have it go well.

Ellen Chisa:

It was always really painful for both of us.

Jack Bridger:

Yeah. But it didn't stop you. Yeah.

Ellen Chisa:

No. But it didn't mean that, like, I then tried to narrow in on more of kind of the people on the other sides of the spectrum. Like, you don't wanna be dropping people into a product that you know isn't gonna work for them.

Jack Bridger:

Yeah. So how did you adjust the kind of strategy?

Ellen Chisa:

I mean, definitely, and that I'm trying to is a while ago now, but I think a quick chunk of that was be saying like, okay, the type of people are going to succeed are the people who have an application and they know what they want to build and they are ready to build it kind of trace in. So like one of the other features of dark was we called the trace driven development, but it was basically idea of like, you would send a post request to an API and then build the API logic after. And so I started kind of screening out of like, okay, do these people have an API they wanna build? And can I imagine the shape of the post request we would send to it? And can I kind of scaffold out of my head what our application would look like after that?

Ellen Chisa:

And then I would also specifically, one of the things I found that people could build an entire application when they were on the phone with me, but then the challenge of that was like, okay, they're done building. They don't need to do anything else. There was no reason for them to come back and build again. Because that wasn't really great from my perspective. So looking at things where I was like, okay, how far can we go today and then cut ourselves off?

Ellen Chisa:

So, like, they're coming back to finish this without me.

Jack Bridger:

Yeah. That makes sense. And what one of the things that you you had a background where at some point you were teaching, right? You were teaching a general assembly.

Ellen Chisa:

Yes. I I kind of think of my personal mission is I like helping people make things and that can be like, I love giving people capital and I've done that in a bunch of different ways. I love teaching people things, but I also love making tools that help people make things. And so, yeah, like teaching is one of those 3 prongs for me.

Jack Bridger:

Yeah. And do you think that there were things that you took from that experience into, being a founder?

Ellen Chisa:

I think there certainly were. It's actually quite hard for me to say. I also went to an engineering school called Olin College of Engineering that when I went there were the 1st alumni had just finished and we were unaccredited. And so I went to, like, a purely experimental college. And so I think thinking about pedagogy and how people learn comes very naturally to me because of that.

Ellen Chisa:

And so I think it's just so deeply infused into who I am at this point that I don't actually know how it impacts things.

Jack Bridger:

Very interesting. Yeah. I remember you asked me when we first spoke about how do I because I said I was trying to, like, learn in this podcast and how do I actually reinforce it. And it sounds like, yeah, you're always thinking about I imagine you were thinking about, like, I don't know. Does he write flashcards or does he do that sort?

Ellen Chisa:

I think I I think it was a little bit of a selfishly motivated question. One of the best parts of being an investor is that you get to meet lots of interesting people every day and you learn lots of little bits of content. And I think it's like hard to say, like, if you talk to 8 awesome people, how do you, how do you make sure you actually, I think them giving me the time is like such a sign of respect that I'm like, okay, and you've given me this gift of time and the gift of your insights. I want to keep track of them well, and then I want to, when possible, like pay them forward to other people. So like those ideas keep getting into the world and like keeping track of everything.

Ellen Chisa:

So you can do that, other than just doing it organically. I would, I would like more better ways to do that.

Jack Bridger:

Interesting. And so being an investor, yeah, I think you mentioned before that it's it's, like, lots of different work or maybe, like, less focused deep work and more conversations. And, what and also something else you've said is that there's power in busy work, and I'm not

Ellen Chisa:

I think one of the interesting things about being an investor is usually no matter who you're talking to, they know more about the space that they're specifically working on than you do. Like, as a founder of something, you probably have spent the most hours in the entire world thinking about that specific which I think is awesome. And like, I loved being that for dark. And that's probably the thing I miss the most about being a founder. And so I think when you're thinking about investors, it's very tempting to be like, oh, like Ellen was on the scaling DevTools podcast.

Ellen Chisa:

She She said all this stuff about building DevTools. She knows like more than I do about this thing. And like, that is definitely not true. Like every founder knows more about their space than an investor would. And so it's important to be able to kind of take from investors, what are the patterns they've seen or what are things that might be useful to you?

Ellen Chisa:

But at the end of the day, the founder kind of decides like what is useful to my business here and how does like this broader experience apply to my situation? Yeah, there's, it's a very different kind of thing.

Jack Bridger:

Yeah. And, and, and why is busy work, important?

Ellen Chisa:

I think with this a lot, I've been thinking about this a lot lately with our.

Jack Bridger:

So what is busy work actually? Just, Okay.

Ellen Chisa:

I feel like does that make sense? We all, like, we want to be doing work, and I think all of us enjoy the creative process of doing work. And so, like, when you talk about people, like, getting into flow and, like, writing a bunch of code, like, that's one format of it. Like, you could have the architecture in your head, but you can't magically turn that to a fully functional program. And I don't think most people want to.

Ellen Chisa:

And then same way we'll talk about, like, oh, the hard work of, say, being a staff level engineer is, like, the talking to the different teams and the coordinating the different people together, which is much more PM like in a lot of ways. I think that is also a form of, like, we're doing this activity to eventually get to a form of creation. But it was just like, you could snap your fingers and all of the teams just agreed. I don't think anyone would find that a very enjoyable job. And so I think to some extent, when we are building and like when we are consumers of tools, like we want to feel like things are like hard enough, but not too hard.

Ellen Chisa:

And we want to like consistently be like applying effort to something. I think most people at the end of the day don't want to go like full. I guess it depends. I think most software engineers at the end of the day don't wanna go full 4 hour work week. Like, I think a lot of us do this work because we enjoy the craft of doing the work.

Ellen Chisa:

I'm sure someone's gonna come and be like, no. You're wrong. We all don't. Listen to me. I enjoy the work.

Ellen Chisa:

Probably some of the people who listen. And so I think that's important and I think that's kind of true regardless of the role you're in. If you're a software engineer, if you're an investor, there are definitely things I do, They don't like the, like, oh, this is the magic moment. I found the founder. We're gonna do the round now.

Ellen Chisa:

There's like a lot of, like, listening to people and talking to them and then sitting by myself for half an hour while I, like, try to explain to someone why I'm passing on their company. It's like there's a lot of that work that comes in, and I think that's, like, a big part of how we eventually have new ideas and insights as well. It's just kind of all of that interstitial time of doing things.

Jack Bridger:

Yeah. So it's kind of, like they're really valuable and it also make life enjoyable.

Ellen Chisa:

Yeah. I don't know if that was like a well fleshed out thought yet, but if other people have kind of been thinking about that, I'd be happy to hear from them and talk more about it. Because it's just something that's kinda been stewing on lately.

Jack Bridger:

Yeah. No. It makes sense. Yeah. If things are too easy and kind of can just be achieved sat in front of your computer or I am maybe it's I mean, obviously, there's a lot of joy can be had there, but I feel like it's most of the hard things involve getting like, leaving your desk and talking to people and persuading people and

Ellen Chisa:

Being rejected by people. Being told by people you're stupid. Yeah.

Jack Bridger:

Yeah. Yep. So one one thing I I wanted to ask you is now that you are investing in developer tools, having built a developer tool. What do you think you look for that's different from what most investors might look for?

Ellen Chisa:

I don't quite know how to articulate this, but I definitely, for better or for worse, investors talk a lot about how, like, you think about people and you think about market. And I definitely think about people and I think about market, but I learn about people in market by talking to people about their products. And so I think, like, I spend an unusual amount of time talking to people about, like, would it be built? Why have you built it this way? And not because I think the, like the version of the product that exists is the one that's gonna exist forever.

Ellen Chisa:

Like I'm trying to judge if it's a good or a bad product. I like use the product as a lens to talk to and go and understand like who they are and what they're motivated by and why they're doing this and where they wanna go in the long run. Mhmm. And I think for a lot of developers and a lot of products people, the, like, the product is kind of like a manifestation of, like, our ideas that we have made. Like, it's like it's like it's kinda like art in a way.

Ellen Chisa:

And it's like the version of the art that you've put in the world to, like, be able to interact with. And I think it's like the best thing to interact with to understand how a founder's thinking about their their company.

Jack Bridger:

Yeah. I think that that I really resonate with that. I think preparing for the interview so I kind of do the same thing of not even not talking but just trying it out and it reflects personality a bit as well. Yeah. That's a really good point.

Jack Bridger:

And, are there any companies that you're very excited about at the moment?

Ellen Chisa:

Oh, man. That's like having favorites.

Jack Bridger:

By the way, you're gonna say a lot, and then I'm just why don't you just say everyone that you're excited about, and I'll just randomly edit.

Ellen Chisa:

No. I think, since we already talked about them, I'm always excited about Liveblocks. They just had their 2.0 launch recently. One of the things I love about them is, like, they do a really great job of speaking to developers and making, really usable tools for developers to adopt while also speaking at a high level to a PM or to a business lead about why they would care about what Liveblocks is building and why would they care about it being a developer friendly product. I think they've done that extremely nicely.

Ellen Chisa:

Similarly, I really admire the Zuplo team for taking a category that people kind of thought was, like, played out or a little bit boring saying like, no, this like really like it is infrastructure, but this can be infrastructure for developers. And I think that's something that, like, I really admire about them and about their experience. So those are definitely 2 that came out today, and, like, I'll just, like, re echo that there are 2 that I'm excited about.

Jack Bridger:

Yeah. That's a very, very smart way to do it.

Ellen Chisa:

Easy, you picked.

Jack Bridger:

Yeah. Exactly. They're they're my my two favorites of your portfolio probably. Well, Zuplo is probably my favorite because they've been on the show.

Ellen Chisa:

We'll have to send you more.

Jack Bridger:

Yeah. Send send them over. Actually one one thing that that one last question, is you mentioned about LifeBlocks marketing to multiple kind of people, not just developers that care about LifeBlocks. Have you seen any things that work well, especially at the early stages when you have that challenge?

Ellen Chisa:

Yeah. I think it's really about segmenting your message, depending on who you're talking to. Like, if you go to a JavaScript conference and talk at, like, a very high level about the future of collaboration, like, that's not gonna, like, it's not gonna resonate. Whereas if you go talk to a CIO about who stands, probably also not gonna resonate. They're gonna be like, what's that?

Ellen Chisa:

I've never heard of it. Why are we in the weeds here? And so I think it's really about nailing your message by the audience that you're talking to.

Jack Bridger:

Yeah. That's that's a really good tip. Amazing. Ellen, I think that's, that's about it. Thank you so much for joining, and thanks everyone who recommended that Ellen come on the show.

Jack Bridger:

And, yeah. Where can people learn more about you and about, Boldstar?

Ellen Chisa:

Yeah. You can find more about us at Boldstar, especially if you're thinking about starting a company. There's no real too early to meet us. We like talking about people to people about the problems they wanna solve and their hypothesis for how they're gonna solve it first, But we're at boldstar.bc. I'm Ellen at boldstar.bc.

Ellen Chisa:

You can Google me. I'm Ellen Giza pretty much everywhere on the Internet. I'm easy to find.

Jack Bridger:

Amazing. Thanks, Ellen, and thanks everyone for listening.

Ellen Chisa:

Thanks for having me.

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