This is the latest episode of Product to Product, a podcast for / by product people.

Listen to the episode below:

We’re joined by Ellen Chisa. You may know her as the VP of Product at Lola, a former product manager at Kickstarter, or as a previous PM at Microsoft. Most recently, Ellen left Lola to launch her own startup that will make it possible to build a complete scalable app in an afternoon. She’s essentially creating a brand new programming language that aims to bring the ability to write software to a billion people. While her startup is still in very early stages, Ellen is completely in founder mode.

Our CEO, Latif Nanji, has first-hand experience with the PM-to-startup founder journey. So we thought, who better to chat with Ellen about how a role in product can prepare you to be an early-stage startup founder? With an increasing number of PMs starting their own companies, the two entrepreneurial PMs discuss how you can apply your PM experience as an early-stage founder. Plus: they determine whether product is actually the right field to be in when starting your own company.

The episode can be listened to above, and we’ve also included a transcript below. You can subscribe to Product to Product on iTunes (here) and Google Play (here), or get the latest episodes delivered to your inbox by subscribing here.

Latif: Thank you, Ellen, for coming to the podcast.

Ellen: Thank you for having me. I’m excited to get to talk about going from product to being a founder.

Latif: Perfect. I wanted to start by asking you if you could talk a little bit about your career in product management.

Ellen: Absolutely. I’ve spent most of my career in product management.

I did my undergrad in engineering at a brand new engineering school that focused on project-based learning. From there, I worked at Microsoft, and then I was a product manager at Kickstarter in New York. And then, I was at an incubator and ended up becoming head of product for one of the projects, which was Lola, a travel company based out of Boston. I was there through our series B, and built out the product team. Then, last spring I left to start a company with my co-founder, and that’s what I’m doing now.

Latif: I would love to hear a little bit about your new startup. What problem are you looking to tackle?

Ellen: All of the things I’d worked on at Microsoft and at Kickstarter—and the thing that was missing for me in travel—was helping people make things. In particular, I really like helping people make software.

My co-founder, Paul Baker, and I felt like it was still way too difficult to make software. We spent a lot of time doing logistical, operational tasks to get things done—not writing or shipping feature code. We wanted to go about removing as much of that complexity as possible.

Latif: That sounds like a pretty big problem to tackle. I was reading your website—and it sounds like you’re looking to build a new programming language. Is that correct?

Ellen: That is, actually. We really felt like a big issue was that we’ve been incrementally improving our development tools, when in fact our environment has completely changed from writing code on one machine to writing code that needs to go to a distributive system. We felt like languages weren’t designed for that. We started building a language that’s really tightly integrated into its own editor.

"Now, at this startup, everything is my job"

Latif: How has that transition been from going to running a product team, to doing that plus being the CEO and founder of a company?

Ellen: I felt like in my last role I was doing a lot of founder-related things as well. I was definitely involved across the board, since I was there so early. But there was still a lot of stuff I didn’t have to do. I didn’t have to be a person who was doing the fundraising. I didn’t have to be the person who was figuring out where our office should be. I didn’t have to think about payroll and benefits, and hiring. I thought about hiring for just the product team and I helped do interviews, but it wasn’t as though I coordinated the entire process.

Now, at this startup, everything is my job—and that leaves a lot less time for the type of product work I was doing before.

Latif: Are you still looking to hold product for the early part of the startup, or have you thought about how you would structure the first set of hires? And how does product management fit into that?

Ellen: My co-founder, Paul, started working on this before I did and he is really great at product. He’s really great at the long-term vision and looking at something and knowing if it’s done or if it’s good enough. But he didn’t have as much of the classical training for, “How do we get a process set up? How do we make sure we’re shipping the right things? How do we think through our hypotheses?”

To some degree, I can rely on him really heavily for early-stage product work—and both of us really like product work—so that’s sort of our unifying thing as founders. That’s been extremely helpful. We’ve also thought a lot about the person we want doing design at the startup. We want someone who is a very well-rounded designer, who’s excited about being involved throughout the whole process. Not someone who just wants to solve a constrained set of problems.

Latif: What were some of the things in that last six months at Lola that pushed you to build your own startup What prepared you to make the transition from a product manager to a founder?

Ellen: I always knew that I wanted to start something again. I’d done a startup with some friends in college. It was a complete disaster. I knew I wanted to do it again once I had enough experience to feel like I was doing it well.

The timing actually was completely unplanned and was very inconvenient. I planned to stay at Lola. I loved the team. I loved what we were building. But even so, when I went into Lola, I’d taken the role because I really wanted to work with Paul English, the CEO, because I really respected him as a founder. I went in planning to learn from him, and I told him upfront that this was something I really cared about doing, which is part of why he supported me in that journey.

I think probably the biggest thing for me in that last six months was that my team started growing and having more experience, and I got pretty comfortable with letting other people make decisions. I think that’s a thing that a lot of early founders can struggle with because you feel like every decision is really important. You feel like you’re the one who has the final say, and you have to figure it out.

I think having the experience of my team coming to me and saying, “Oh, I want to own this core part of the product” or “Oh, I want to differentiate our strategy for these two user groups” really helps me learn to let go. I think that’s helped a lot with the stress of being a founder.

Latif: Was there anything personally that you were setting yourself up for? Was there anything tactical that you were reading? Were you starting to talk to investors early on? What kind of activities did you do on that front?

Ellen: I got pretty lucky. I had actually started building relationships with investors—because I got to be involved in meetings at Lola and through events, conferences, and spending time in the community.

I spent a lot of time writing and sharing my ideas before I became a founder, and I think that made me comfortable sharing things that I worked on publicly. It helped me think about, “How do I think about building a team? How do I think about hiring? How do I think about product?” It gave me a little more breadth than I would have had just from my role internally.

Then, the second piece of that—which I wish I would have done a little bit differently than I did—was since I was writing, a lot of product managers would reach out to me and want to grab a coffee, want to chat. I got to meet a lot of people, and I think that can be really helpful––to have people to bounce ideas off of. I do wish I would have diversified roles a little bit more. I feel like I know a billion PMs, and I wish I knew maybe a third of a billion PMs, a third of a billion engineers, and a third of a billion designers, instead of having it be so concentrated in one job description.

Latif: Wow. That actually is quite insightful, because then when you’re trying to hire for those people, it sounds like you have to build out those networks—which you are probably doing now, I suspect.

Ellen: The nice thing about knowing PMs is PMs do know lots of other people. I take meetings with everyone I know who is a PM and I ask them who some of the best people they’ve worked with are—people who they think this idea would resonate with. I get introductions, and then I continue those conversations. I think it would have helped to build some of those relationships earlier.

Latif: How have some of the team structures you’ve seen in product management influenced your decisions on structuring your startup’s team?

Ellen: I care very much about having democratized teams—a lot of autonomy in decision making. I think when I’ve seen product teams move slowly, it’s often because a founder or a head of product wants to make all of the decisions. They need everything to come through for approval and have a bunch of meetings before something gets decided. That’s frustrating for the PM who really does want to be able to develop their own ideas that fit into the company’s strategy.

I also think a lot about, “How do we set up the right high-level guide rails so everyone on the team knows what we’re trying to do?” But not set up, “You have to do it this way” or “This is the right answer.” And instead, focus on helping people make sure they’re solving the right problems.

Latif: Do you feel like you have to spend a lot more time outside of the product because the type of problem you’re solving is very complex? How have you started to think about those problems as a founder?

Ellen: One of the things I feel that is most important for an early stage startup is having founders in the office frequently, and having founders who have their hands on the product all of the time.

I think I’m taking on a large set of those other responsibilities because that gives Paul, my co-founder, the leeway to be in the office writing code pretty much continuously without being interrupted by meetings. That’s something that’s very important to me—I just feel like part of my job is being there to help Paul do the work that he is best at, and be most successful.

I think, personally, it’s also a little more taxing for me to go meet new people every single day for however many meetings per day, compared to working with the same product every single day and coming into the office super excited to see these people. It’s not that I don’t like new people—there’s just a different feeling when you’re working with someone you work with every single day, and when you’re meeting someone brand new.

Latif: How are you planning to build out your team early on? Who are your first set of key hires are? Is a product manager going to be hired in the near future?

Ellen: No. We decided pretty early on what we wanted the core team to be—and that’s two engineers, one infrastructure scalability person, one designer, one operations manager to help with everything logistical, and then the two of us.

Since Paul and I are both drawn to product, having an additional person would remove us from what we’re both good at and like to do. I think also because the product is relatively ambitious, I think it would be difficult for that person to get their head around it at this stage, as compared to a little bit later on when we have some more pieces of the direction figured out.

Latif: Could you talk a little bit about what you most enjoy about switching over to a founder? And what have been some of the biggest benefits of that?

Ellen: I think one of the things I really like is that it feels like there’s no safety net. Whereas I feel like when you’re working in product you’re working with a founder, and you are trying to help them figure out where they’re going, and why, and get things done. But at the end of the day, you know that they’re not going to let you do something that’s completely wrong. You kind of have this extra gut check that goes into it, and it’s a gut check with authority.

For me, I think that’s really helpful when you’re starting out, but I wanted to be in the position where I felt like I was going through that myself.

Latif: Have there been decisions where you felt like the gut check wasn’t completely valid, and you weren’t completely confident? How did you approach that problem? Did you talk to other product managers, other founders, advisors?

Ellen: Paul and I do that together. We hired our first engineer, Ian Connelly—and just having another person in the room was really helpful, especially another person with fresh eyes.

A large part of that is talking about things as a team and taking a step back, and bringing our three independent opinions together—and Stephie’s as well, our operations manager.

Then it’s also about bringing external people in. We bring in people to usability test. Some of those people are the specific type of engineer who would use our product early on. Some of those are friends who have been engineers for a long time and we want to get their high-level thoughts on the direction. Some of those are other entrepreneurs. I think it’s just about bringing people in and making sure we have the right people to bounce ideas off of.

Latif: How have you focused your time as a product manager? Are there any specific areas that you were maybe surprised by how much time they require?

Ellen: I used to spend a lot more time helping people figure out what was going on, or kind of debugging their problems. I think it’s because I was in a slightly larger organization, so I would spend time talking to PMs about, “How do I convince this person of this thing? I’m having this problem. How can I make it go better.” In an early stage startup, there isn’t really any of that friction, and so I got back a lot of time from that.

"I used to spend a lot more time helping people figure out what was going on, or debugging"

Same thing, even as a head of product, I wanted to have one-on-ones with my peers on the executive team, with my manager, with my team, and so a large chunk of my week just went to having one-on-one meetings with people, and kind of keeping the train on the tracks. Whereas at a four-person company—which is what we are right now—there’s only so many meetings you need to have, and a lot of them happen ad hoc because we’re all sitting in one room together. We’re all building the same thing. We’re very tightly focused. I think to that regard, I got a lot of that time back, that I didn’t have before.

Latif: I totally get that. One of the things I discovered is that I had to go back to the days of requirements, and doing excessive numbers of wireframes and mock-ups, and get better at design. I’m not sure if that’s something you ran into as well, as part of the startup.

Ellen: A little bit. I think it’s a little bit better since we started from a language. Engineers really like designing languages, so some components of that are handled by my co-founder and our engineer.

But yeah, there was definitely an adjustment period where I went back to doing work instead of managing people––and even just like, “Oh, I’m going to set up our Trello.” I didn’t do that. We had someone who specifically was great at setting up task management systems at my last job, and I was like, “Okay, I like setting up Trello. I’ve done this a billion times. I just haven’t done it in the last year or two.”

Latif: Can you talk a little bit about how you define success as a startup founder and as a product manager?

Ellen: I have a framework that I use for myself, where what I’m looking at as a product manager changes depending on what the business goal is.

For me right now, metrics aren’t very important, because we haven’t shipped anything to users. We’re building things out incrementally, and so almost everything I look at is a combination of, “Where do we see the future going?” and “What is the future we want to build?” And then, “Are users using it? How do they react to it?”

It’s sort of a mix of what I think of as being almost an artistic vision, and also qualitative feedback from users. Certainly, metrics will come more into play as we get further along, but right now it would be relatively low numbers and not super useful for us.

Latif: Gotcha. It sounds like there is a larger qualitative aspect that’s going on where you’re evaluating how your users are interacting with the early versions of the product, and will probably continue to do so until there’s a point of confidence to ship it more publicly. Is that kind of how you’re thinking about the next few steps? What does that look like to you?

Ellen: I think of qualitative research as what helps you figure out why things are working or not working. I think early on, the “why” matters a lot more. The quantitative research is very good for figuring out “Is it working or not? What impact did this specific change have?” But right now, so many things change every single day that it would be hard to understand what the relative quantitative impacts of anything were, particularly at this scale. I think, later on, that’s much more important, where you can start to look at a set of things that you monitor over time.

Latif: How has product management helped you become a stronger founder? What were those skills or traits that you picked up along the way that gave you an advantage over other founders?

Ellen: I think there’s a bunch. One is just comfort with having been in startups before. I know a lot of great founders who came from a different industry and found a problem that they really wanted to solve, but haven’t been in that experience of having this tiny team and just needing to get everything done—and haven’t been through the process of shipping software before. I don’t think that’s specific to being a product manager, so much as specific to having shipped software in small teams.

I think product-wise, another piece is I got the chance to work with two founders, Perry Chen at Kickstarter and Paul English who previously founded Kayak and then Lola. I had these examples of people who built great companies. What do they do? Why do they do it? How does the team respond to it? What things are beneficial or challenging for the team? I think that made me pretty aware of the dramatic impact founders have on a company, and I think that can be uncomfortable. A lot of people, especially in their first role that comes with some sort of power, don’t really want to own that. They just want to be part of the team, because that’s the fun part. That’s why you’re a founder. You want to sit in a room and build things with these people, but I think it’s important to realize how seriously people are paying attention to your words and your actions—and so I think that helped a lot.

I think I’m also fairly lucky. One of the nice things about sitting in a product role is you get exposed to lots of things around the company. All of my roles have uniquely let me have a little bit of that. I also went to Harvard Business School, so I got a year of formal finance training, which was helpful. I think being in a seat where you can see lots of the different things that are happening means, even if you aren’t an expert in doing one of those, you’ve at least seen someone do it before—whether you thought they were doing it well or not––and you can call them up and ask them questions. I think just knowing what you don’t know, or knowing what the spaces are around you can be really helpful as a founder.

Latif: Now that you’ve experienced things from the founder side of things, how would you as a product person work differently with founders?

Ellen: I started figuring this out while I was still doing product. There was a point at which I realized that a lot of my role was to help them express what they were trying to express, and get the team’s support and buy-in for that—more so than it was to convince them that I was right.

I think I had a lot, especially early on in product, tied up in wanting to be right, wanting to have great ideas. Towards the end, I definitely thought of my role much more as a facilitation role, rather than as a “deciding what we should do” role. I think that, again, depends on the founders and depends on the startup. That’s not necessarily how I want it to be here, but I think that’s definitely something where I would have tried to be more attuned to what founders needed in that way.

I think another thing is that when I first started working on an executive team, it was a pretty rough shift for me. As a PM, I was like, “Oh, no. PMs work cross-functionally.” Shifting into the executive team and now building our team, I’ve realized that it’s about a lot more than engineering, and all of the conversations I was having as a PM were actually pretty technical. I think I would have respected that the founder probably was thinking across a much broader space, and I would have tried to spend more time there, not just on solving specific technical problems.

Latif: What do you mean by broader space? Is there a specific department that maybe he was thinking of? Was it resourcing across other areas of the business? What does that mean to you?

Ellen: I had never really thought about how different it is to hire and manage a service team, especially a service team that’s maybe compensated differently than an engineering team.

I had a mental model of how people work and why people take a job, and what they’re motivated by that was super engineering-, and design-, and product-focused. I hadn’t really thought about that class of problems before.

Latif: What are a few tactical ways that a role in product prepared you to start something? What inspired you? What’s the mental preparation, if any?

Ellen: I’ve thought about this a lot recently and I’ll give you the backstory. When I met my co-founder I was happy in my job. My husband and I had just bought a house in Boston and it was not a good time for me to be doing a brand new startup. We were in the middle of planning our wedding.

For me, the risk profile is just such that I was like “Oh no I really want to build this company and I really need to do this.” I think I have a risk profile that is pretty well suited to being a founder, and I’m pretty good at seeing large opportunity rather than trying to minimize downside risk.

I don’t think that’s the truth for every product manager, and I don’t think risk profile necessarily correlates with product management. That’s sort of just a trait I’ve always had. I went to a brand new college that wasn’t accredited. I’ve worked at other startups. I’m just willing to kind of put myself out there. That’s a big thing that enabled me to be a founder.

One other thing I did as a PM, that I think was helpful for becoming a founder, was spending a lot of time with friends who are founders and that I really respected. I talked to them about the challenges they were going through at the early stage. For them, that was helpful because they had another product person thinking through their problems. For me, it was helpful because I was getting to see the other side of the table. And I did that with friends but then I also started doing it in angel investing.

If you’ve been in a product career for a while or you’ve built out a product team, you might be far enough along in your career that you might have the financial means to start writing small checks to other startups. I think that getting involved with startups is a good way to kind of see that side of the table, understand the problems that are going on, understand a little bit more of what you’re going to go through while fundraising.

I would definitely encourage people—if you think you might want to start something eventually—to get into angel investing or advising other startups. It can be a good way to start to understand what you’re going to be facing.

Latif: Now that you’ve been on both sides of the table, what questions are you asking that maybe other traditional VC’s or investors wouldn’t ask?

Ellen: I’m interested in hearing about how people plan to go to market. And why they decided to solve this problem. Which are more conventional things, but I’m also interested in how they’re setting up the product process. What was the last hard product decision they made? Why did they make it that way? How did they make it that way?

I’m more likely to want to get a perspective on how people are operating, and a feel for what they like to do as founders, in addition to just is this the right market? Is this the right team? And I think that’s partially so I can learn and also because I’m looking for founders who are thoughtful about those things.

Latif: There seems to be a whole bunch of debate around whether product managers are the CEO of their product. I was wondering, now that you’re in the founder seat, what is your opinion of this concept?

Ellen: I don’t feel like I think about product dramatically differently as a CEO than I did before—but I also think that my style of working is to do the thing I think needs to get done, regardless if it technically falls within my job description. Which means, honestly, that I’m not a good large company PM at all. I’m not great with authority. I’m not great with structure. I’m not great with rules. I like starting things.

I think there probably are PMs who are like that, but I don’t think they’re the PMs that every organization wants. I think an organization needs to be realistic about setting expectations around what they want the PM to do.

Latif: For any product managers looking to found their own startup, what’s your one or two most actionable pieces of advice you’d offer so that they can prepare for that stage in their career?

Ellen: Definitely start meeting and talking to other people—founders, engineers, designers, marketers, sales—whatever you think you’re going to have to hire early. And just start getting your ideas out there. If you don’t know what it is you want to start yet, just start talking about spaces that you find interesting. There’s no way you’re going to get to the point of starting something without some deliberate effort in that direction.

Latif: Is there anything specifically you listened for in those conversations that influenced your thinking?

Ellen: Yeah, I’m actually listening more to myself sometimes than to the other people—it’s what they say that gets me excited, what challenges my beliefs the most, and it’s sort of what starts to feel like “Yeah I really want to bite into this problem.”

Latif: Just as a final question for you, where can people find you online?

Ellen: I’m @ellenchisa basically everywhere but particularly on Twitter or for more background or more of my writing it’s ellenchisa.com.

Latif: Thank you so much, Ellen for being on the podcast today, we really appreciate your insights and your time and we wish you the best of luck with your new startup.

Ellen: Thank you so much for having me.

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