From PM to Product Leader to Founder with Dark’s Ellen Chisa

Build with Maggie Crowley

Today on Build, Maggie sits down with Ellen Chisa, CEO and co-founder of Dark, which is making it possible to build an app in a single afternoon. Maggie and Ellen talk through her journey from PM to product leader to founder & CEO. Plus her years of experience at Microsoft, Kickstarter, Lola.com and now her latest venture, Dark. Also on Build, learn how to set up a product team and listen to what Ellen’s reading now, from fiction to the best reads for product leaders.

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Full Transcript

Maggie Crowley: Hello. Welcome back to Build. This is Maggie today. I’m really excited because I have Ellen Chisa, the CEO and cofounder of Dark where they’re working to make it possible to build a complete scalable app in an afternoon, Ellen was previously VP of product at Lola a travel startup here in Boston. She was also a PM at Kickstarter and before that a program manager at Microsoft. We met just sort of around in the Boston scene and I’m really excited to have her on the show. So Ellen, welcome.

Ellen Chisa: Thanks for having me today.

Maggie: Yup. So I want to get into two things in depth. First, one of the things we talk about a lot on the show is sort of how to go from how to a be better as a PM, but then how to go from PM to product lead and then on to founding your own company. So I want to talk through your journey through that whole process. And then now that you’re a CEO and you’re cofounder and you’re sort of in charge of the whole thing, how are you approaching products from scratch? So first, what was that journey like from you? From PM to product leader to founder.

Ellen: Yeah, absolutely. So I think my journey was a little bit unusual in that when I went into product I specifically knew that I wanted to start a company later and so I really went into it with the mindset of PM is this great opportunity because it’s a job where I’ll get to see a lot of different things. I’ll get to pitch in where I’m needed. I’ll get to work closely with everyone across the company and I really thought it would be good preparation for someday being a founder.

And so when I was starting out, I actually, I was coming off of another startup that I started while I was an undergrad, that was, I think we made every mistake you can possibly make, although I’m still making more so maybe not. But quite a lot of them. And coming out of that, I really thought that the thing I needed to learn how to do better was how to ship high quality products. I felt like I had a lot of ideas. I was super excited about user research. I loved spending time with customers. But then when it came down to writing really good reasonable code that didn’t have very many bugs and we were able to fix it and maintain it quickly, that was something that had been really lacking in the first startup I tried to do. And sort of the antithesis of that was going to Microsoft, which shipped full box software. At the time it was still, Office was on a three year release cadence.

So when you made something you knew how it had to be good because we’re going to be stuck with it for three years. And so I feel like my time at Microsoft really helps me learn a lot more about that. And I think that was really kind of even baked into the ethos at Microsoft of what a PM should do. One of my mentors there, Ian Todd, always talks about how he felt like when people first get into PM in their very first job that they got hired either because they’re really good at starting something, bringing high energy to the project, having lots of ideas, being able to think in a novel way or are they come in because they’re really good at getting things out the door. The skill that I didn’t have, getting stuff shipped and making sure they think through every single edge case. I think that like first early step for me in really becoming a PM as opposed to somebody who wanted to be a PM or wanting to be a founder was learning how to do that full cycle from, I’m excited about this, I want to make it happen. I have lots of novel ideas, through, yup, we’re going to cut the list down, going to do these things and we’re going to do the smaller set of things really, really well.

Maggie: Right. Yeah. I think that resonates a lot with me. I think some of the hardest projects I’ve ever worked on are when we have to remove a feature or sunset something and it’s like it’s one thing to start something, it’s another thing to finish and it’s a whole nother thing to remove something from a product that people are using.

Ellen: I think people really underestimate the role of product and removing things. I think engineering actually is a really great culture around this where people will celebrate deleting lines of code, removing tech debt, cleaning up a code base, but I don’t think I’ve seen very many PMs to get promoted for cutting a feature out or removing it from the product even though it’s often the right thing to do.

Maggie: Definitely. Okay, so that was your, the foundation that you were looking for and do you think that you got that across those two experiences that you had?

Ellen: Yeah, for sure. So I definitely had that at Microsoft. I remember the first time someone asks me to think through a edge cases, I was really bad at it and then I started realizing, oh there’s like all these constraints around different devices, or all the constraints were on browsers or like things about like what do you do when the networking stack goes down and I think that was super interesting for me. I think the thing at Microsoft that was challenging for me and another important part of being a PM is having the short loops of building things so you can have an idea, ship it, get the feedback from users, know what’s happening, modify and do it again and really feel like your working on something very actively. And so it’s a long shipping cycles were very hard for that and I think that was one of the reasons I decided to leave Microsoft and go to a smaller company like Kickstarter.

The other one being I feel like as a PM, and this isn’t true for every PM, some people can pick up a product manager job and do a great job on a product even if it’s not something that they would use every day. But for me I feel like I do my best product work when I’m working on something I care about a ton and I really want to use and I really think is making a difference in the world and I really identify with the user and want to support them completely. And so when I shifted to Kickstarter, I was looking both for those shorter cycles and also to be working on something that was really personally meaningful. And so I would say at Kickstarter there were things that were definitely similar to Microsoft.

I know a lot of times when I talked to early career PMs coming out of a big company, they think going to a startup will be this completely different world and nothing that you have done will transferred or vice versa. I’ll talk to people who were like, oh, I was at a startup and I was flying by the seat of my pants and they just want to go to a big company where they’ll tell me what to do and I feel like they actually have more in common than one would think.

Maggie: Yeah. I mean having done both, I feel the same amount of flying by the seat of my pants, but just in different ways in both situations.

Ellen: Yeah, exactly. Where I feel like at big companies you have the, how do you communicate to your product lead? How do you communicate to your VP? How do you communicate to the overall executive team? But at smaller companies it’s sort of the same thing except instead of someone who’s sitting there with their spreadsheet tracking business metrics that’s been operating this giant company for a long time, it’s the founder who has this internal idea of where they’re going and they’ve been trying to go in that direction for a long time. And so either way what you’re trying to do is take your idea and communicate it to someone else who be coming at it from a different perspective and explain what you’re trying to do with the product and why. And that’s really the same whether you’re in a big company or small company.

Maggie: Yeah, I agree. It’s something that we’ve been talking about a lot here, again, which is that communicating those ideas and telling good stories. And having a good narrative gets you so far as a PM and so much farther than I expected. And something that I’ve learned recently, like if I were to go back, I would have told myself in my first PM job like the better your story, the better your future’s going to be. But you know, it took me a long time to learn that.

Ellen: I totally agree. I feel like I got really lucky working at Kickstarter because Perry Chen, the CEO cofounder and Yancey Strickler, who was also a cofounder, both cared a lot about word choice and storytelling and they were willing to invest a lot of effort in getting that right. And during the time I was there, even just the way I wrote email, the way I communicated with even the engineers I was working with that I talked to every day completely changed because I realized how much value you could get out of being thoughtful about it.

Maggie: Right. Okay. So then you were at Kickstarter and then what prompted you to leave?

Ellen: Yeah, Kickstarter was super interesting and so I think what happened for me was my role there was I was the PM for the discovery experience, which I really identified with. Like I said, I wanted to go somewhere where I could think about the users. And for me I always enjoyed supporting people who wanted to do creative work with capital. And so in a way I was building for myself as well as for a bunch of other people who liked to do the same thing. And over the time I was there I ended touching almost the entire products. We shipped advanced discovery. We actually made some changes to try and make it easier for people who are backing projects to start to think of themselves as creators. So I got to work on some changes to the start page, we completely redid the activity feed for how people that updates from projects.

We redid the backorder history where you can keep track of what you’d supported. And so I touched almost every part of the site that backers were using or working with and some that creators were working with too. And I felt like I was no longer adding as much because a lot of the things I thought about, were already in the product and I also felt like personally I’d gotten to the point where I could only think about Kickstarter related things and whenever I had a new idea for a project that I wanted to do or something I was excited about and I was still in this mentality of wanting to start a company, I would think of something and then I would realize it was just a Kickstarter for something else or it was just a feature that should be part of Kickstarter and I felt like in a way Kickstarter was getting diminishing returns from me because a lot of their early work I’d done had shipped and was out there and I was also getting diminishing returns because I felt myself narrowing rather than really having lots of ideas for what I wanted to add to the world. And that signaled to me that it was time to move on.

Maggie: Right and you’re, at the time, like maybe when you’re at a company for a long time you might be growing in scope in other ways and you weren’t getting that opportunity either.

Ellen: Yeah, exactly. The way the team was set up, we were a team of, we had a head of product who was both the head of product and engineering and four PMs. So it was myself, someone who worked on the creator experience, someone who worked on the internal tools experience because we had a giant community teams that did really great work and someone who took on really large scoped projects that didn’t neatly fall into another area. So like the first time we did internationalization, the first time we did mobile. Projects like that. And so the way the team was set up, and especially since you have so many fewer PMs than engineers in many scenarios, there wasn’t really a chance for me to move into a product leadership role just because there were other people there who were good and qualified and also deserved to be doing that type of work.

And so I felt like if I wanted to do that, there just wasn’t that much opportunity for growth because of the size of the company and what the company needed. And so at that point I decided to leave and I had also applied to Harvard Business School, where you also went a few years before that. And I had run out of time that I was allowed to defer. And so by deciding to stay, I was kind of taking a guess at will I get to do something later and I was going to be giving up this chance to go to a really interesting place and see a lot of ideas. And so for me it seems like the right thing to do to go to HBS instead of staying and waiting.

Maggie: Yeah. And one question, I feel like my reason for going to get an MBA is one thing, but I feel like, what was your hope for going to get your MBA? What did you think that you were going to get out of the experience and like how did you think that would add? Because it is a question I get all the time, which is, you know, should I go get an MBA?

Ellen: Yeah, absolutely. I don’t think PMs should think of it in terms of should I get an MBA? I have a whole talk I like to give on this about like how people should think about what they’re learning. But for me, one of the ways I like to learn is I really think of different disciplines as being a different lens that you can see the world through. And so since I went to engineering school for undergrad, sometimes I put on my engineering hat, which I don’t think of as being a writing code hat. I think of it as being a like thinking through a problem systematically, diagramming how it works, working through every step and every detail and figuring out how they go together. Or I might put on my designer hat, which again not pushing pixels, but more thinking from the perspective of who the end user is.

What mental state are they in when they come to the product, how are they feeling when they use this feature? What types of things are they trying to achieve? And I felt like I understood those two mindsets really well. Having been to engineering school, having taken graduate classes in design, having had so much experience as a pm, but I was still a little bit iffy on how do I think this about through the mindset of I’ve created value by making this product. How do I do that in a sustainable way where I’m making enough money and I’m making a fair amount of money for the company. And I’d really liked Kickstarter’s, business model where we took a certain percentage of the money creators raised when they were successful. So they had enough money, they knew they were going to be able to do their project. They could always put that extra buffer in knowing how much the fee was since it was consistent. And I wanted to think about what are other things I could do like that. And what are other business models that make sense like this?

Maggie: Interesting. But then you only did your first year, right?

Ellen: Yeah, so I went to HBS. I did my first year, the RC, which I really liked because I feel like it’s a really good foundation across the board. I loved learning about how to make financial models really liked some of the cases about leadership and things through your own strengths and weaknesses. I was not great at accounting, which taught me that one should always hire a very good accountant because it’s important.

Maggie: Yeah, I can second that a lot.

Ellen: Yep. It’s very good for people who are extremely detail oriented in a particular way. Like I’m detail oriented in some ways, but just not that one.

Maggie: I learned that I would never go into finance or accounting. So yeah.

Ellen: And so like I think it was just fun to get to learn a whole bunch of new skills and I intended to go back to the second year. But what happened for me was I had planned to either spend my summer in venture kind of seeing the other side of the investor or operating roles. But the more I talked to investors, the more people pointed out that I really liked building things. I was really excited about working on one thing consistently. I really like saying yes, I really like providing resources to people and a lot of the venture job is talking to a hundred people and saying no to 99 of them. And for me that was going to be kind of sad and not rewarding.

And so people in venture kept being like, why don’t you go find it? Like you’ve worked with Perry, you’ve worked with this one founder who’s super interesting, why don’t you find a founder who’s completely different than that and go work with and learn from them. So then once I decided I wasn’t going to spend the summer in venture, I was really interested in other entrepreneurs I might like to work with.

And an interesting opportunity came my way where Paul English, who had previously started Kayak, was running a consumer technology incubator in Boston and was hiring interns who are basically entrepreneurs and residents for the summer in this incubator to work on a few internal projects that they were excited about. And so I decided to join Blade in order to do that with him. And the thing that actually convinced me about it was I felt like one of the areas I was still weak in even coming out of HBS, which is surprising, was that I didn’t know very much about sales and one of the projects in particular seemed like it was going to have this huge element of cold calling small businesses and trying to convince them to use this product and I was super excited to put on my sales hat and try to do that since it’s sounding pretty uncomfortable to me as an introvert as someone who talks to a lot of people, but frequently people that I already know or people in my discipline or people that I’m working with.

So I wanted to see if I could do it and see what that was going to be like as a founder. Then when I joined, I ended up not working on that project and what I ended up working on instead was what became Lola.

Maggie: Oh, interesting.

Ellen: Yeah, and so at the beginning it was only me working on Lola and I’d read some emails scripting code to see if I could learn about my travel preferences. I got to go to travel agent school. I made a spreadsheet at the time, conversational commerce was sort of the new UI concept and people were excited to see like, could this be the new app store? So I spent a bunch of times looking at products that were like that. I spent a lot of times thinking about how you put together a very simple end consumer interface with a more complicated interface for experts in this case, travel agents. And so my job was really broad at the beginning and over the course of the summer as Paul and his cofounder decided to turn the incubator into a company to build Lola full time, he gave me the opportunity to stay at Lola, which was great.

Maggie: Do you think at that point that you had the things that you had wanted to get out of HBS and so you didn’t need to go back for that second year?

Ellen: That’s a great question. I think I learned a lot. I think in particular, the thing I learned that I’m the most fond of was how to make really good financial models and good cashflow analysis. So I think that was interesting to me. I would’ve really liked to have gone back. I think the other thing I wanted other than the like practical skill was since I went to engineering school for undergrad, I had this picture in my head of getting to sit in coffee shops and read books and talk to people about ideas and like what I think liberal arts college must be like. I’ve no idea if this is true or not.

Maggie: It wasn’t like that. I hate to ruin that dream for you. But we were also just doing problem sets and going to class.

Ellen: Oh, I don’t think I’ve ever actually asked anyone before. So I’ve been like imagining this thing for 10 years.

Maggie: Yeah. I have an econ degree and a minor in literature and we did read a lot of books, but maybe it’s just me. I mean, I wasn’t in a coffee shop, I was just in class. I think just like everyone else.

Ellen: That’s funny. Okay. Well I was hoping for this idyllic experience my second year of HBS where I took only the classes that I loved and was super interested in and I talked to people about them in the coffee shop all the time.

Maggie: Yeah, well I mean that wasn’t unreasonable for the second year. I think, you know, it’s interesting. I went because I didn’t know what I wanted to do with my life and I hadn’t heard of product and I wasn’t really sure what I was doing. I was in consulting and I discovered product along the way, but I did spend my second year taking classes I liked that were more along the lines of things that I wanted to learn more of and there was definitely more of that aspect, way more than it was an undergrad, so maybe it would have been the dream, but slightly different than an undergrad liberal arts education.

Ellen: Yeah. I really wanted to do it. But then when I like put the things side by side, if I’d had the opportunity to build and grow a product teams side by side with a founder I really respected before going to HBS, I would have taken that opportunity instead of going and so it seemed silly to turn it down just because I was halfway through a degree. And I figured if it didn’t work out, I could always go back to HBS later, which was kind of my thought at the time.

Maggie: Definitely. So you went from from program manager to PM and you have this opportunity at Lola to be VP of product. What were you looking to get out of that experience? Like I’m assuming at the time you were still sort of eye on the prize. I want to be a founder. Like what did you go into that role looking for?

Ellen: I don’t think I actually got to think about it very much. What happened with that role was the first month since I was working on an intern project was pretty calm and like I would go to work, I would work on it for awhile, I would talk to people about ideas. It was very exploratory, there were a lot of other companies around. I helped out some of them as well, but then as soon as we hit the ground running, it went from just being me working on it to like 10 of us working on it. And then less than six months later there were 50 of us working on it. And so I didn’t have much time to think about the growth curve. I just had to make things work every single day. And that meant that I learned a lot of things I wasn’t necessarily expecting to.

I think the first one was that we weren’t really originally planning on the hiring product. They didn’t have product at Kayak at the beginning. Paul himself is a really strong product person as was his cofounder and I was already there. And so when we got to the point where I had stopped scaling because I was chewing too different many different things, it wasn’t like I sat down and was like, oh I’m going to hire a PM.

I was like, okay, I need to get these things done and they’re not happening. Who at this company has skills that might be useful and how can I convince them that they would like to help me in addition to doing their other job. And that was sort of how the team started to build up. One of the first people who moved to the product team, Jeremy Hahn, who’s still there as a product manager now had been a travel agent on that team and just had a really great eye, especially for quality, he was constantly reporting all of the bugs, both for the travel agents and for users. He was constantly the person who was coming down and learning how to use the new travel agent console features. Then like going back upstairs and teaching everyone how to do it and he was just really engaged and really interested. And so yeah, he just really jumped in and hit the ground running in terms of helping me out with some of those things.

I think another thing was really realizing how important communication across the team was and I think as a PM I was working with a lot of people, but we saw each other most days. There was a few enough of us that we had a shared understanding of our product simply by the work we were doing day-to-day. And one of the things that was different about leading a product team was constantly reiterating the mission of what we’re trying to do, which is very similar to the founder, of like this is what our goal is for the long run. In order to do that, we have to hit these metrics, the initiatives we have to hit these metrics are these and the way your work fits into that is this other thing that you’re doing. And so realizing that a large part of my job was just repeating myself and saying the things over and over again to help motivate everyone else and keep everyone going in the same direction was really interesting and felt really fluffy to me at first as compared to sitting down and writing a spec for how something should work.

Maggie: Right. Yeah. I feel like we hear that over and over again, which is, if you’ve said something once, you haven’t said it nearly enough, no one’s going to remember. You have to communicate until you feel like you’re a broken record for the message to actually get through. And I agree. I think it wasn’t until I became a product lead that I sort of started to feel that, you know, I said it and that’s not enough. No one picked up on it. So I have to continually say the same things over and over again until you finally started to see people pick that up.

Ellen: Yeah, exactly.

Maggie: So thinking back across those roles, what are the big themes and the big learnings that you took to your new company and as a founder that you’re sort of leaning on in that new role?

Ellen: Yeah, so I think the first one, going back to what I just said was when I originally moved from Kickstarter into the product lead role at Lola. I for some reason, and this seems crazy in retrospect, thought I would know the entire product at the same level of detail as I had previously known my small part of the product area. I don’t know why I thought that, but I think a big part of that role for me was learning that the right thing to do when you’re in a leadership role is often to specify the problem rather than specifying the solution. And then you have to trust the people around you to bring you to solution. And I think that was a pretty hard warning curve at first. And I think it’s one of the most valuable things I got out of being a product lead that I didn’t get out of being a PM.

So I think that’s a big one. I think a second one that’s been really helpful is the ability to scope projects and particularly the ability to scope projects and draw hard boundaries around them and explain why those are the boundaries and how things fit with them. And so like I think that started way back at Microsoft where we would write prioritization lists and then there would be like a very specific cut line and then you had to have the meeting for negotiating. Things would go above or below and it was really high stakes because you were shipping things that were going to be used for years, not like you could deploy again the next day and fix it. And I think having that sense of a kind of a pattern matching, an intuitive sense of where should this cut line fall and what set of features this cohesive together is something that I find really valuable now.

In particular because since with Dark we’re building a holistic programming language editor and infrastructure compiler that’s basically redoing a giant product area. Like you could probably summarize, it as four to five different products put together. And so we lose a lot of complexity because we put them together and a lot of the hard parts of the boundaries between them, but when you’re thinking about inventing a programming language on day one you can’t sit down and make the entire programming language and so thinking about how to scope that was something I never would have known how to do without being a PM.

Maggie: Interesting.

Ellen: Then I think another one that’s been good and I think is a good thing about being a PM or a leader at different companies is just learning lots of different ways to do things and so my cofounder, most of his working experience was at the last company he started Circles CI and he has methods that work for him that work really well for him and I wouldn’t say that I have one method of developing a product that works really well for me.

It’s that I have a hat of like 50 things and I’ll look at a problem and then be like, oh, this tool might be helpful for this. We should build like a quick JavaScript prototype and then try it out with the user. And for this we should actually do some ethnography and go talk to 10 people who have this problem and understand why they have it first. And for this we have a ton of users and we want to like make a test and actually look at the data that comes out of it. And so I think being a PM and especially being a PM at different sized companies, it gives you exposure to way more things to put in your tool belt.

Maggie: So taking a step back and thinking about like product at Dark, are you sort of letting it build on its own or are you picking like a specific way that you want your product process to be? Are you just too small to even really have that yet? Like having been a PM and all these different scenarios now that you have the chance to do it all your own way, what does that look like?

Ellen: I think the funniest thing I’ve realized about being a founder is all of the things you critiqued other people for before are mistakes that you will then make even though you know how not to do them.

Maggie: Right. Because I can see every PM thinking about being a founder and saying you know this draconian process or this meeting than I hate. It’s going to be different when I’m a founder.

Ellen: Yes. And that is exactly what I thought and yet I still made some of the same mistakes. At the beginning we were super lightweight on process and we actually didn’t really have to do anything because a long time our team was only four of us and that meant that everyone could just sit in a room and talk to each other. All of our check ins were really lightweight. And then we actually really ran into this when we hired a couple more people, we started to need a lot more structured and not even structure. We just started to need to be more thoughtful about how we were getting things done in order to have it like not fall apart and make sure everyone was contributing as much as they were able to. So I think things that are important to me is I always want everyone to know what they’re working on and why that’s important to the business. So I’m still a big fan of iterating what’s important. Every single week I send our team and email every Sunday night that they read when they get to work on Monday. It’s about what I’m thinking about, but always ties back to our overall goals and what we’re doing. And so that’s a big thing.

And then we have planning Monday morning. I think it’s really important to let people estimate their own work rather than dictating from above how long things should take. So I do triage with my cofounder and we made sure we know what we think is the most important. But when we have people commit to their work, they’re coming into their work and estimating how much they think they can do. We’re not saying this was what has to get done this week. We have a really strong culture of interrupting people when we get stuck. I don’t want to see people sitting around and like being stuck on a problem for a long time. And so that means like if you are stuck, you should talk to someone else about it. For sure. And then I think the last piece for me is one of our core team values is to be reflective. And so we do retrospective, basically everyone does this at this point, but we try to set ours up so everyone’s able to give feedback on not just their work and why things got done or didn’t get done, but what would make their overall working environment better.

Maggie: Right. So those feel super familiar to me as someone in product. But what about the other functions? Do you have marketing, sales, ops, all that kind of stuff, and are you using the same principles for them as well?

Ellen: We don’t have all of those yet, just because the nature of the company is so much that we’re building this development environment for developers. It’s a very technical team right now. I do think we will have similar things. I don’t know if they’ll look exactly the same, but in terms of setting a high level goal and then working to achieve that goal, listening to the team and empowering individual people, I don’t think those are things I would ever want to change regardless of discipline.

Maggie: Definitely. Yeah. We formalized ours in a series of leadership principles and I definitely thought when I joined that it was sort of fluffy and not something that I thought I would use day to day, but a couple of the most of the principles actually I found to be useful in terms of tie breaking and decisions or making sure prioritizing effectively and they scale pretty well across the teams and it’s sort of a nice common framework that we have. You know, between marketing and customer success and product and engineering, we can all say, okay, we’re going to put the customer first right now. What is the best outcome for the customer? Let’s do that and we can use that as a team to kind of align ourselves.

Ellen: Yes, that makes a lot of sense to me.

Maggie: And it’s funny, we also get a Sunday night email from DC.

Ellen: Yeah, I think it’s like pretty common. Paul English used to do it too. His might’ve been a Monday morning email though.

Maggie: Yeah, it’s interesting. It’s really nice. I can at least say from my perspective that, you know, you might think that you know what the CEO is thinking about, or you might think you know what the founders care about because you know, as a product lead, I interact with them on that in that capacity. But hearing the sort of, I’ve been reflecting over the weekend, I haven’t been in the office. This is what’s on my mind. That’s really helpful and really nice to hear. Especially even more so when it has nothing to do with when I’m working on that day. But it’s more in general, here’s what’s on my mind.

Ellen: Yeah, that makes sense.

Maggie: So I think it’s probably one of my last questions, but now that you are a CEO and cofounder, is it what you hoped it would be? You know from that back in the day when you were just starting as a program manager and you wanted to be a founder?

Ellen: Yes. It’s interesting because I think a lot of founders find it to be really stressful. And I wouldn’t say that it’s not stressful, but I think with any job you’re kind of trading off what type of stress you have. And so for me as a PM, I felt the same level of ownership over my work. And so when I couldn’t convince leadership either like product leadership earlier in my career or like founders later in my career about something that I really believed in, it was really hard for me to not be able to see that impact on the product, especially if we did something and then it didn’t work. And it was like I wish would have done it my way and we could have seen. And so I like having the ability to be in control of that. And I think that reduces the stress level for me a lot.

And then I think the other thing is I’m just really interested in wording lots of different disciplines and knowing what’s going on. And I think one of the funnest things about being a founder and a CEO is when your team is early and it’s small, you’re basically everyone’s number two employee. Or if they need to brainstorm with someone, they’re probably going to brainstorm with you because you’re the person who’s around who can take the time to do that. And you’re the person who can work through problems with everyone. And I really enjoy getting to do that.

Maggie: Yeah, that’s really cool. I didn’t think about that. So what advice would you give to other product people who are thinking, you know, I have what it takes. I want to be a product lead and then I want to be a cofounder or I want to be a CEO of a company. You know, having gone through that journey and being like, right in that journey right now, what advice would you give people who are thinking about that?

Ellen: I think the first one with moving to being a product lead is remembering that you are going to be less hands on than you were. And so I think it can be a struggle to be a PM because it’s not like you shipped a specific set of code. At the end of the day you enabled a feature to be shipped and being a product lead is even more removed from that where it’s you enabled your PM to enable something to ship. So you have to like really check in with yourself and think, am I going to find this rewarding? And then I think the second part is thinking about how to support other PMs. And I think one of the interesting things about PMs is I don’t think I’ve met two PMs who learn exactly the same way. I think every single PM I’ve managed needs something different to get better at their job. And so you have to be very flexible as a manager to be able to support the team you have.

Maggie: Okay. And then what about for people who want to be founders?

Ellen: Yeah, I think the interesting thing about being a founder for me, and this obviously depends on who you’re working with. My cofounder is very technical and wanting to write code all day, but also has really great insight around product vision and really came up with the original core concepts behind what we’re doing technically. And so for me, the way we split the responsibilities, I still get to do a lot of the products rituals around figuring out how our process should work and making sure everyone else is involved and helping us scope. But a lot of the ideas are still his and a lot of my day to day job is things like fundraising and hiring and dealing with logistics and making sure we have an office to work out of and making sure the internet in the office works and so there’s so many other things you’re doing that you don’t necessarily get to spend as much time on the product as you would like. And of course the early stages when you spend the most, because that’s when the product matters the most. But if there’s something pulling you away, you’re probably going to be the person who has to deal with it. And so you have to get pretty good at being able to do both of those things at once.

Maggie: Right? So it’s not that you get to go and found a company and then you’re in your product dream world, but instead there’s actually tons of other responsibilities that are going to take your time away from that.

Ellen: Yeah. And then I think the other big part is that people don’t necessarily tell you as many things once you are in this case, I guess CEO. But I think probably the same thing holds for any founding team member is people don’t necessarily tell you the truth anymore because they want you to be happy. It’s your thing, you’re always selling the dream. And the communication dynamic definitely changes when there’s a different power dynamic.

Maggie: That’s super interesting. I never thought about the fact that you would go from expecting people to treat you one way and give you the same information and then all of a sudden your title changes and it’s very different.

Ellen: Yeah. And I do miss that. Like I think one of the fun things about being an early career PM is everyone will tell you everything and you know, all of the feelings of everyone on the ground, every time there’s an organizational shift and the further up you get, the less of that you hear.

Maggie: Yeah, it’s true. I think the product lead job can be a pretty lonely at times. Okay. So last question. What are you reading or listening to right now that’s helping you in your role? Either you know, specifically about business or just something that’s completely different that’s helping you sort of unwind?

Ellen: That’s a great question. So the most recent book I read that I really enjoyed was a book that just came out called Daisy Jones and the Six. It’s fictional, but it’s written as though it’s an interview with a band about their rise to fame and their fall from fame. And I think I’ve been reading a lot of things like that because the way I feel about startups is that there’s no winning when you’re a startup, you just keep going forever. Because, I mean even seeing like recently all the challenges, Facebook has had, they’re a giant company, they IPOed and everyone would agree they’re successful and they still have all these problems and I can’t imagine it feels good to deal with those and so you’re never done. It’s just do you enjoy doing it every single day? And so I think I read a lot of fiction that has to do with like how do people think about success? How did they deal with it? How do they balance the joy of doing the work they like every day with the pressures that come with external recognition.

Maggie: Oh that’s a really good one. That’s awesome. I think it’s probably the best answer I’ve had to that question so far.

Ellen: I feel good about that. I read a lot of books and I spend all my time trying to convince people that you should read fiction and that it is interesting and teaches you about humanity and not just like super businessy things.

Maggie: Yes, I have a literature minor like we mentioned in the liberal arts education and I 100% agree. I feel like I learned more about the human condition and how people make decisions to how they act, which is critical to being a PM through reading fiction and not through reading 10 amazing lessons that you need to have now to sell more whatevers.

Ellen: Yeah, exactly. I also read nonfiction. I was reading The Everything Store recently, which is about the rise of Amazon, which goes to that same theme of like what is it like as your company grows and changes over time.

Maggie: Yeah, that’s interesting. We were, I was checking out pieces of the High Growth Handbook and I know people have been reading The Messy Middle as a couple of other examples of that. I also just read an early copy of Julie’s book on making a manager, which is really awesome and really helpful tool that’s coming out soon for how to be a better manager, which I thought was really interesting. So I do agree that those books are great and I have learned a lot from them. But I think as a PM, the best thing you can do outside of that is to do things that will teach you how human beings are. And I think fiction is the best way to do that.

Ellen: I definitely agree.

Maggie: Yeah. Well, Ellen, thank you so much for coming on the show. I really appreciate you taking the time, especially since this is actually our second time and our internet didn’t work the first time.

Ellen: Which is my fault as a CEO founder, but hopefully my internet is better now.

Maggie: Yeah, yeah. Talk about what it’s like to work at a start up. So everyone who’s listening, please give Ellen a shout out in the reviews, five stars. Let me know if you have any questions, any feedback. And Ellen, again, thank you so much for coming on the show.

Ellen: Thanks for having me.

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