Poornima Vijayashanker

How to Find Your Other Half: Secrets for a Good Co-Founder Partnership


We all have ideas for features, products, and companies. But we cannot bring them to life alone. Partners and teams help us get out of our echo chambers, see possibilities we’ve never imagined, and put one foot in front of the other when the going gets rough.

The best teams are composed of individuals with complementary skill sets, and as we learned back in Episode 4, empathy for one another.

But you might be wondering: How does a team form over time? And how do you pick an initial partner or co-founder if you’re starting from scratch?

In today’s episode of FemgineerTV, we’re going to talk about how to pick partners, assemble a founding team to get your idea off the ground, and reveal the key ingredient to a lasting partnership.

To help us out, I’ve invited the co-founders of Pop Up Archive, Anne Wootton and Bailey Smith. Pop Up Archive is a startup based in Oakland, CA that makes sound searchable by using cutting edge speech-to-text technology. Anne Wootton is the CEO and Bailey Smith is the CTO. We’ll learn about how, as co-founders, they split their responsibilities, support each other, and resolve conflicts.

Here’s what you’ll learn as you watch this episode:

  • the traits you should look for in a potential co-founder that are different from a teammate or an employee;
  • how to communicate setbacks to your co-founder; and
  • how to critique each other constructively.

If you’re actively looking for a co-founder, or if you already have one and want to improve your partnership, you’ll want to watch this episode!

After you’ve watched the video, let us know what your favorite part was in the blog comments below.

The next episode of FemgineerTV airs in August. I’ll be hosting experience designer Pauly Ting. Subscribe to our YouTube channel to know when it’s out!

How to Find Your Other Half: Secrets for a Good Co-Founder Partnership Transcript

Poornima Vijayashanker: Welcome to the sixth episode of Femgineer TV, brought to you by Pivotal Tracker. I am your host, Poornima Vijayshanker, the founder of Femgineer. Femgineer is an education company where we teach innovators how to build software products so they can find freedom in their careers, enrich other people’s lives, and make the tech community a lot more flexible and inclusive. As innovators, we all have ideas for features, products, and companies, but we can’t build these things alone. We need to have people who are on our teams with complementary skill sets, who can breathe life into our ideas. As we mentioned in the fourth episode, the best teams are the ones who have, not only have those complimentary skill sets, but practice empathy for one another.

You might be wondering, “How does a team form over time?” Or, “How do you go about picking a partner?” Maybe if you’re starting from scratch you’re wondering how to look for a potential co-founder. Well, today on Femgineer TV, we’re going to talk about how to go about picking a partner and getting them to help you get your idea off the ground.

To help us out, I’ve invited the co-founders of Pop Up Archive, Anne Wootton and Bailey Smith. Pop Up Archive is a startup based out of Oakland, California. They make sound searchable by using cutting-edge, speech-to-text technology. Anne is the CEO and Bailey is the CTO. On today’s show, we’re going to be talking about how they came together to start Pop Up Archive and how they split up their responsibilities as co-founders, and of course most importantly, how they resolve conflict as they continue to build their company. Hi Anne and Bailey, thanks for joining me today.

Bailey Smith: Hi, Poornima.

Anne Wootton: Thanks for having us.

Poornima Vijayashanker: Yeah, of course. We met about a year ago when you had joined 500 Startups accelerator program and I was advising you guys. It’s great to see all the progress you’ve made in the past year. Before we dig into talking about Pop Up Archive, why don’t we just start by talking about your backgrounds and how you two met. Anne, why don’t you kick us off.

Anne Wootton: Sure. Bailey and I met at the Berkeley School of Information about five years ago now. We had both dabbled in journalism in our very early careers, but technology was changing everything and turning us on its head. We both, coming from humanities backgrounds and undergrad, we were really inspired to learn more about technology, spend some time deep-diving so that we could ultimately combine that with media for the betterment of the industry.

Bailey Smith: Yeah. As part of the application process to the school of information I wrote this incredibly sincere essay about how I wanted to save journalism by helping find better business models. I thought, you know, data analysis and involving technology somehow would be the way to do that. It turned out in our program, there were very few other like-minded people, so when it came thesis time and people were pairing off into small groups, Anne and I had a natural affinity for one another. Poornima Vijayashanker: That’s awesome. That’s how you two got to know each other, you paired up as partners to do a project, your thesis project?

Anne Wootton: Yeah. I had worked on the newspaper in elementary school and high school and college and ran a project to digitize my university’s paper before I met Bailey. While in grad school had come across the Kitchen Sisters, these radio producers who have been on NPR for decades, and they knew that I was kind of interested in digital archives and bringing the history of the news into the present. They asked if we could help them build a digital archive for what they had come to call their “accidental archive.” That was the opportunity that Bailey and I decided to hone in on for our Master’s thesis, thinking somewhat naively that it would be a walk in the park of writing some lightweight plugins for some pre-existing open-source software, that in fact did not exist.

Poornima Vijayashanker: Got it. All right. What actually got you inspired to start working on Pop Up Archive?

Bailey Smith: The original incarnation of Pop Up Archive was actually called Pop Up Radio Archive, and it was this project which was these few small open-source tools that you could use with existing software. At the end of the project I think we both realized, “Oh, there’s a bigger opportunity here, there is a much bigger problem than we originally thought.” Like Anne said, I think we both really sincerely believed of course someone solved this problem already, and as we really delved into it, just realized that there is a solution that we were kind of in a position to provide. I don’t know if we would have kept at it if we hadn’t had like really strong additional encouragement from the Knight Foundation and it really, I think, solidified the feeling like someone was behind us and someone really wanted this. We kind of just went all in as soon as we got the support from Knight.

Anne Wootton: I’d even back that up a few months because it was absolutely Bailey who initially suggested that we apply for some business plan competitions while we were at Berkeley. We got enough attention and won a couple of those. It gave us a little bit of money and then it was also Bailey who suggested that summer once we had finished the Master’s program or starting to sort of pursue other work that we apply for the Knight News Challenge, which is a way that the Knight Foundation funds innovation in journalism. They used to endow professorships at journalism schools and this is their way of really trying to fund sustainable hybrid business models and innovation in journalism beyond faculty positions at universities.

Poornima Vijayashanker: Got it. Bailey you mentioned that you had used some open-source technologies, but how did you two go about initially building Pop Up Archive?

Bailey Smith: This was the first project of the sort of scope that I had ever worked with. I am a very firm believer and when you’re an initiate in something finding the best minds in the world, work on the problem with you, well, in the world maybe, is a big statement but really the best minds in the field. We reached out to the Public Radio Exchange and they had been doing a lot of software development in the space and they’d done the app for This American Life, Radiolab. They had conceived of a similar project where we had been working on and realized that they did not have the bandwidth to work on it and so they asked if we would be interested in some sort of partnership in the beginning. They really helped us get started and get infrastructure in place and allow Pop Up Archive to ultimately grow into what it’s become now. We’re very appreciative for the early days they taught us a lot.

Poornima Vijayashanker: Oh, nice. You collaborated with them to build the initial product?

Bailey Smith: Yes.

Poornima Vijayashanker: Got it. I am sure the rebirth of podcasting has caused a lot of podcasters to look for your product and start using it. Are podcasters the main customers and how do they go about using your product?

Anne Wootton: Podcasting has been around for a while. It’s over 10 years old. That being said, it’s a pretty slow although steady growth industry, which is not necessarily what a lot of investors are looking for but it’s reliable, which is something that we find comforting, and it has made a difference. Podcasters aren’t the main customers for Pop Up Archive right now—we work with a lot of journalists and newsrooms and universities. Large collections of audio, which we can talk about in a minute, but the sort of, all of the attention paid to Serial and the boom, as some people referred to it in 2014, definitely helped focus the attention of the sort of fledgling podcast industry in terms of monetization and business models.

It’s provided a great opportunity for us; you know we work with some podcasters who use Pop Up Archive’s tools to help them create their work and deal with all of the audio that they record in the process of podcasting, but there are also bigger entities, networks, aggregators, distributors who are thinking really critically about how to distribute and provide good experiences around podcasts. That led us to branch-off into our latest product, actually, which is called Audio Search.

Poornima Vijayashanker: Nice. How do your bigger customers use you? You talked about podcasters but I know you’ve got some other big media companies. How are they using your product? What are the benefits to them?

Anne Wootton: The way Pop Up Archive works is that we take sound from anywhere. It can be an independent radio producer dragging, dropping a file into their browser, or it can be a humongous server full of files stored at a place like the Stanford University library or Huffington Post. We take all that sound and we run a bunch of different software on it. Our speech-to-text software is trained specifically for that type of media for sort of news media, oral history, first-person conversation and then we analyze it and tag it so that it can be searched by topic or people or location.

The bigger organizations will use us either in their newsroom to support their reporters and their staff in producing content and being more efficient in distributing it by enabling search engines to index all of the words inside of an audio file so that people searching for phrases will find those exact moments in audio, or for archives and universities to create accessibility to big collections.

Poornima Vijayashanker: Oh, great. Yeah. That’s very important. That’s fantastic. I want to take you both back in time to when you first started out on Pop Up Archive. What inspired you to begin working on it?

Anne Wootton: Aside from being sort of archival enthusiasts off the bat, the opportunity we saw with the Kitchen Sisters and the bigger problem that that illustrated was that there, especially with digital audio and video, is so much media being created by so many people all the time. You may be able to find some of it on commercial platforms but those aren’t preservation-minded. There is no guarantee that that stuff will be around in 50 or 100 years, and even for older collections as they are digitized and brought on to the web, there are all of these voices and they’re telling these incredible stories and they are, you know Studs Terkel talking to London cabbies or Maya Angelou telling the story of when “I know why the caged bird sings” was first released in the ’70s.

We really saw this as an opportunity to not just help save that material but also make it accessible, because if you can’t search it, it’s pretty hard to know what you’ve got on your hands. An example of that is last year when Maya Angelou passed away, there was all sorts of news coverage about her, and the LA Times ran a blog post where they linked to this particular interview that she had done where she talks about her childhood and sings, and that’s material that had been digitized by the Library of Congress but would have sat, you know, at the time was sitting on servers, kind of otherwise unknown, and through Pop Up Archive we had brought it out into the public and made it possible to find through the typical search mechanisms that we’re all used to, typing things into a Google search bar, for example.

Poornima Vijayashanker: Yeah, that’s great. You’re really preserving these voices and you’re also giving them longer lifespan beyond someone, so that’s fantastic.

Bailey Smith: Yeah. Imagine not being able, and I am constantly gushing about The New York Times archive, it’s like maybe my favorite thing ever. They’ve got every word in The New York Times back to 1981, and imagine not being able to search that, which is the reality for podcast and also video, any of these like opaque, sound-based mediums.

Poornima Vijayashanker: Fantastic. Let’s switch gears and talk about how you two have developed as co-founders. I know one of the things as a co-founding team that’s important is to have complementary skill sets, so you don’t step on each other’s toes, which you two clearly have, but as you’re doing that you also want to keep each other informed about your decisions. Let’s talk about what are each of your areas and how do you two communicate and talk to each other about the decisions that you’re making. Let’s start with just in general: what are your areas?

Anne Wootton: Sure. Our responsibilities fall down along pretty standard CEO, CTO lines. That being said we’re a small company, we’re five people now and before this when it was just the two of us, we were all the hats all the time, as you can imagine. I spend a lot of time working on business developments, sales, strategic partnerships for the company. To oversimplify it, I spend a lot of time writing emails and working on spreadsheets and Bailey spends a lot of time writing and shipping code. That being said, I find our relationship to be complementary in a lot of ways. I talked about Bailey being the one who frankly came into the grad program where we met with more of a mindset to create new business models for media, and she was the first person who said, “You know, I think we should apply for this money from these people. I think that would be a good idea.” That’s where I mean, Bailey is process oriented, too, but that’s where I come in and sort of the logistics. How are we going to get this done and everything that entails and helping, like push it through to its final existence and the deadline freak.

Bailey Smith: I think we both, like Anne definitely does more of like the business, the relationship stuff, she’s much better at naturally than I am, which is really nice to have that complement and I have generally like a patience with technology that I think is unique to me, and the Venn diagram where we come together is the product stuff. I think we really do work on that together. I do design and technology, but when it comes to making product decisions I feel like that’s where we meet and talk through everything as a team. Not even just the two of us really with the employees as well trying to make all those product decisions together in a way that’s meaningful and structured and we have a long-term vision that’s building towards some sort of goal. It reminds us when we forget about what the goal is.

Poornima Vijayashanker: Yeah, that’s important, especially as a CEO. When you each come up with the ideas, how do you keep the other one informed? What’s sort of the communication process like?

Anne Wootton: You know, we’ve always had a pretty open back and forth between the two of us. I think Bailey knows even if she ignores some emails that she can’t ignore mine, so that’s good. If something comes into one of our minds, we communicate in a lot of different channels, whether it’s emailing each other or texting each other or Slacking each other about things we think about. Will often get text from each other when the other one is having a meeting or talking with someone who’s saying interesting things to them and it’ll just be like a long list of the names of companies or things we’ve never heard of before that we sent to the other.

We’ve built more structure into our communication as we brought more people on the team because they need that framework to operate within and we can sort of play it by ear and rely on the fact that we were luckily naturally good at communicating with each other about things like new ideas. Then Bailey is really good, I’ll go off thinking about all of the possibilities and potentialities of a particular idea. She’s really good at sort of nipping that to either like a particular time when it’s supposed to be addressed or just keeping us on task with what’s happening on a given day or as I need to be thinking about the big picture and the vision but there is a place and a time for that when it comes to everybody else’s time.

Bailey Smith: We have a tendency to make schedule time for when we’re going to have big ideas. Big idea talking time. Monday and Wednesdays we have hour-long meetings where we get really deep into what we’re working on for the particular sprint. If we need something in addition to that, particularly when it’s talking about a feature or a big concept, normally actually we end up giving everyone a little bit of homework. I recently read something it was like brainstorming is best done solo and then everyone comes back together and shares their idea so you don’t groupthink the ideas into nothingness first. We’ve been trying that, like everyone brainstorm about this thing, we’ll come back together, we’ll talk about it. It’s initial forays into this land but I am feeling good about it so far.

Poornima Vijayashanker: Nice. Now, I am sure there’s been some times where it’s not always Kumbaya and brainstorming happily and you’ve had some conflicts or disagreements. How have you gone about resolving those conflicts together?

Anne Wootton: You mentioned empathy and I think that’s probably the key for us when it comes to conflict resolution. We do 360 performance reviews every quarter with our team, but we’ve been working together for years now even before that. We’ve done founder communication workshops, it’s something that we take very seriously. I remember when it was first suggested to us by one of our advisors, we thought like, “Well, we actually, we get along really well,” and he was like, “Well, those are the people who benefit the most from this kind of thing,” because I think you can always get better, and that’s something we’re pretty aware of. That kind of stuff really helps but fundamentally knowing that when we critique each other or express concerns, it’s coming from a place of the best intentions, and wanting the best not only for the company but for the other person. We’re pretty tender with each other, which I think goes a long way when times are challenging or when things get tough.

Bailey Smith: Yeah, agreed. The communication workshops actually like really nice to have someone else tell you, “You should just talk about, you should just talk this thing,” because I wouldn’t have willingly, like in a notes, like not natural to me to like what…because I was like, “Yes, we’re doing great, we don’t need any help.” I would recommend doing that again to someone particularly if you don’t think you already have that good communication. There was some things that I remember…remember this day like had us put like I think an idea in the middle and we had to stand where zero to seven or something, how much we agreed with it?

Poornima Vijayashanker: Oh, interesting.

Bailey Smith: There were some places where we weren’t standing in the same spot and I was like, “I had no idea you felt differently than I did about that,” and probably would never have sussed it out or even if we did, it would have been eventually and slowly and it was good to just like have an occasion to talk through that.

Poornima Vijayashanker: That neutral third party was great to get the conversation started to feel like they weren’t obviously, because they’re neutral not taking sides, but get you to sort of the next level in how you want to communicate with each other.

Anne Wootton: The reason that helps so much is because I think both for our team and for the two of us, communication can be challenging because there are so many emotions inevitably tied up in the ideas and opinions and assumptions that we bring to our work, especially when we love it so much. Doing something like a founder communication workshop or one thing we do with our team is focus pretty strictly on, especially as we develop this new product, right, hypothesis and testing those hypotheses. Giving yourself a framework to operate within, a neutral third party really helps divorce some of the ego from it and enabling you to bring up questions or challenge ideas in a way that isn’t immediately explicitly or implicitly questioning the validity of someone else’s existence or ideas or intelligence.

Poornima Vijayashanker: You probably also had some pretty challenging times together. What was the last challenge you had and how did you both pull through it?

Bailey Smith: The biggest challenge I think was our time at 500 Startups. I mean it was an amazing experience and also really hard work and like just really trying physically and emotionally. You know we were both working really long hours and driving a lot. We’re both living in the East Bay so we’re driving to the South Bay every day, and just really rapidly making a lot of decisions that would really radically affect what the company would become. You know, you’re concerned that you’re not doing a good enough job, that you’re not doing enough work, that you’re making the wrong decision like that. You just like anything, any insecurity that you have especially in times of high stress I feel like just kind of floats to the top and all of those little ripples are hitting the pond.

Then how did we work through it? I feel like we just worked really hard and worked really hard in particular like helping us get a seed round and, I mean, what we really needed at that time was a bigger team, we needed more people helping and we like, I think kind of without even realizing that we’re doing this, like we’re building a foundation for having those people join us while we were at 500 and we were done. I was just like so ready to have it. It seemed like we just kind of like coasted out of it and everything just started working out, really like a lot of serendipity, like a lot of really good luck.

We hired an engineer, Peter Carmen, not long after we finished at 500 and he was just like the exact right fit, exactly what we needed at that time. Our intern became a full-time employee, we needed to ramp her up to full-time. That was all just really necessary and it really helped alleviate a lot of the pressure and then helped us really hit the ground running.

Poornima Vijayashanker: Nice.

Anne Wootton: I think the most challenging moment in all of that was when we were thinking really hard and questioning the business model around the company we were trying to build. We had started, you know, like I said, to save all the lost voices, and then we were faced with, you know, I mean and had been faced for a while with these fundamental questions about how you build a company and pay bills and pay employees, and then depending on your investors, appease your investors, too. We thought about that a lot, I mean, we really were picky about who we took investments from for that reason because, I think the most challenging moment for example was questioning like, “Should we become an ad tech company for audio?”

It’s something that we revisit on a regular basis because we want to keep abreast of the industry and do the things that make the most sense to support audio, which is near and dear to our hearts. Those challenging moments were times where, and I think we felt fraught and what we did was go home and sleep on it and tell each other, you know, “We’re in this together, it’s going to be OK no matter what, and also we need to think really hard and honestly about what we want to be doing when we wake up every day, next month and then two years, and that helped. Those conversations helped us get through it.

Poornima Vijayashanker: There are probably also times where each one of you has faced a personal setback and maybe losing a customer or investor. Bailey, you know a bug in the code base that causes a fire, how do you each communicate your setbacks and help each other through them?

Bailey Smith: That’s actually a really hard thing to do well, because I know, I sometimes feel like a little like, “It’s not my fault, it just happened,” and I am trying to think of a good example, it feels like especially in the week-long sprints, like one little thing can really just throw off everything that you had planned to do, particularly I feel like this most often happens when like a customer needs something and they need it right away and we had planned very carefully to do a few other things that week and that really throws it off schedule.

We’ve gotten, I think, better at communicating about, you know, this is the reason, like this is pushed and it’s like a completely legitimate reason. We’ve also started carefully ranking the priorities on the tickets that we have. Right now we just got them high, medium, low, but if something needs to get pushed, I know exactly what it is within the milestone. That’s been helpful, I don’t know about from the customer side.

Anne Wootton: I think we try to be really understanding of each other’s, sort of unique problems within the roles we occupy. If Bailey is trying to push a feature and then ends up being way more complicated than anticipated, I never hold that against her. At times that it gets tricky, which I think we do a better and better job of mitigating, are when the expectation around how long something is going to take is unclear or the priority level isn’t clear. Like one thing I can say is true today that probably wasn’t true a year or more ago is that like in that sense, Bailey knows exactly like where the priorities lie and it only gets better and better at anticipating the amount of time things will take. At the end of the day, it all comes down to communication. It’s like those things are better communicated to begin with and then she’s in a better position to communicate like, “I know this thing is important, I have estimated it’s going to take this long, we don’t know, you know, we don’t know for sure,” and then as soon something gets funky, we talk about it.

On the customer side, it’s kind of the same thing. We’ve been in enough of product discovery phase for almost our entire existence because even as Pop Up Archive matures, now we’re developing and doing product discovery for this other podcast, you know, search and discovery intelligence engine. It’s not like we have sales quotas each quarter that we’re reliably established and like a specific growth rate that we’re looking for, we’re still in early days in regard to that. Understanding, I think, we set goals when we were at 500 to do a pilot and secure a certain number of contracts and bring in a certain amount of revenue. To be fair, that really went well but when one or two of those didn’t work out it was, I think like Bailey said, my instinct also can be not to say “It’s not my fault,” but to say, “This bad thing happened and now I am going to tweak out on all of the different ways that I can compensate for it and that maybe that person will end up coming around and that maybe I messed up in my communication with them.” In those moments just to have somebody on the other end that’s like, “Hey, you did your best, it’s OK.” Like, “Let’s look forward what happens next is critical.”

Poornima Vijayashanker: Being there for each other through those setbacks rather than like, “It’s all your fault.”

Anne Wootton: Yeah.

Poornima Vijayashanker: I think that’s important.

Anne Wootton: Yeah, we are hard enough on ourselves as it is and we have pretty high standards for ourselves.

Bailey Smith: Like you know when you work with someone that has incredibly high standards for themselves like—.

Poornima Vijayashanker: Yeah, they’re already beating themselves up, yeah. They’re already beating themselves up, you don’t need to like throw a punch in addition to that.

Anne Wootton: Yeah, exactly.

Poornima Vijayashanker: That’s great, it’s good to recognize that. What do you think that in the years that you’ve worked together at Berkeley and now Pop Up Archive, what have you learned from each other? Just one thing that you’ve learned from each other. I am sure there is many.

Anne Wootton: Well, this one will be easy for me if it’s just one thing, Bailey has taught me how to be more concise.

Poornima Vijayashanker: Very nice.

Bailey Smith: Anne has taught me how to be more communicative, actually that all comes from you.

Poornima Vijayashanker: Oh, wow. Great, so you’ve both improved your communication skills?

Anne Wootton: Yeah. I’ll take this moment to also mention that when we did our first team offsite, when we had grown to five people and we all did Myers-Briggs tests together as a little “get to know to you,” and like what are our personality types exercise, we then mapped them using an app incidentally that one of our developers had built as a project, I think when he was at general assembly maybe before or after. We learned that Bailey in my Myers-Briggs types are exact inverses and complements to each other.

Poornima Vijayashanker: Oh, that’s great.

Anne Wootton: I think we teach each other a lot because we’re…

Bailey Smith: I am INTP and you are?

Anne Wootton: ESFJ. Yeah, we’re opposites and we’re also super complementary in a lot of ways, which, I mean, on that front we’re lucky. We’re lucky that we were in the same 40-person grad program and found each other for sure. I can’t discredit that.

Poornima Vijayashanker: It’s great that you’re doing these offsites and getting the team together and understanding people’s personalities and seems like your team has grown over the past year. How have you thought about making those initial hires?

Anne Wootton: Bailey touched on this a little bit already. I mean we’re running a company with two people, it gets impossible pretty quickly and we benefited from having been in grad school and then having the Knight Foundation grant really just take some time organizing ourselves and our thoughts around all of this. It was really obvious to us what we needed as we went to hire those first people. Bailey is an incredible thinker when it comes to leading the technical side of the company and coming up with ideas and directions that we need to go in, but we needed a lead engineer to help with everything from sysadmin to upgrades to scaling our platform. Then similarly after a few months of taking turns loading the Tweetdeck on our Saturdays off, it was pretty obvious that those types of community management, social media and customer support, which we sunk so much time on when it was just the two of us, we needed help with.

Filling those roles was a pretty obvious need for us early on, and like Bailey also mentioned the intern who had come to us in large part because of the culture and the brand that we built for Pop Up Archive, and it’s something that I know attracted some of our investors to us above and before others is that, you know people really like working with us and I think can tell that we care because that’s true, we do. Being able to attract team members based on that, it’s hiring someone isn’t as easy as having a checklist and checking off the boxes one by one. It’s really a much longer term job and building the company that people actually want to work at, who you want to work with too is like a big work but I think that’s almost come a second nature to us because of the nature of who we are and how we started doing this.

Our lead engineer left American Public Media to come and take a total gamble on us, but one year in it’s like everything is looking good, and same thing with the intern who even first proposed that she work for us as a volunteer because she didn’t want to scare us off by asking if she could intern is now our full-time person who does a little bit of everything and we couldn’t do it without her. As soon as we realized that, we started paying her honestly, but now she’s full time and she also manages Pop Cast, our mini-podcast episodes using archival audio from our partners and customers. She is a burgeoning producer too, it’s amazing.

Poornima Vijayashanker: How do you each interact with your teammates? Is there some sort of division, do you all sort of cooperate as a family, how does that work?

Bailey Smith: There’s a lot of family collaboration and we have time set aside. One of our technical members is remote, he’s in Kansas City, so that’s like pretty far away. We have special time set away for like—I like you called it “family”—for family check-in, I am going to put that on the calendar that way from now on. Then like other times set away for technical check-in, just like the deep dive stuff that you don’t want, like everyone to have to listen and spend time on. I am constantly actually looking for new ways to do this, especially with a remote employee, and it’s the one thing that we like talk about all the time and it was like joked about, like this is like why it’s great to have women-led companies, like we seriously talk about communication all the time.

I hope that’s healthy, I think that it is, I think they appreciate it and there is nothing worse than that lingering, festering resentment that grows on to something greater. Trying to make it so that we all have a really super easy way to communicate has been great. It’s like has been helpful, time set aside for tech check-ins is really helpful more like this is actually one thing that I found really important like to have big structural conversations up front and before anyone starts building or even small structural conversations.

Poornima Vijayashanker: What’s an example of a structural conversation?

Bailey Smith: Let’s see, I am trying to think. For instance, we were working on importing images into the site and we get those from lots of different places, this was for audio search. Sometimes we are getting them from SoundCloud and sometimes we’re grabbing them from Wikipedia. There is decisions to be made about like, we’re resizing all these, we’re creating thumbnails, like what are the sizes that they need to be, what does the JSON response look like for that, how do we make all of this consistent, like do we need a new table, all of those decisions.

Poornima Vijayashanker: Yeah, infrastructure.

Bailey Smith: Infrastructure decisions, we have those together. Then you know like the stuff that’s like a little more trivial. You know you are free to make that decision on your own, mixture of freedom and regulation, I guess.

Poornima Vijayashanker: Yeah, processing, consistency is having standards is always helpful. Yeah, nice. As co-founders, how do you think that your lives are different from your teammates?

Anne Wootton: Our lives? We talked about this a little bit because so much of what we look for in teammates is what we also have come to expect from each other. The one thing that stands out to me really is the tenderness, the fact that we are in this together, we both arguably risked a fair amount to do this, and agreed pretty early on that we were all in. If we were to decide we were quitting, it would seriously mess up the other person’s life in a really big way that our employees don’t necessarily have to deal with, at least on the same level. I think really like that deep emotional connection that our job is really fundamentally tied to our lives is what I would say.

Bailey Smith: People always say like co-founder relationships is like a marriage, it’s for real, like—

Poornima Vijayashanker: Yeah, you’re a true partnership and you’re thinking about it in those terms.

Bailey Smith: Yeah, and any upset in that sort of relationship is just as serious as if it happened in your marriage.

Poornima Vijayashanker: Yeah, so it does impact your life?

Bailey Smith: Yeah.

Poornima Vijayashanker: On a daily basis. Nice. OK, last question for you both. I know we’ve talked about, you really view this as a partnership. For our viewers out there, I am sure they’re wondering, what’s at least one character trait that they should be looking for in a potential co-founder? If you can each share what your one trait is that you look for in a potential co-founder and how that’s different from a teammate. I’ll start with you, Anne.

Anne Wootton: Sure. We’ve talked about tenderness and love, which I would stand behind. The other trait would be a willingness to challenge the other and to get into the weeds on a level that you never fully can with someone who’s your employee, because you’re coming from slightly different positions and that can be a pretty murky place but it’s an important one.

Poornima Vijayashanker: Mmm-hmm. What about yourself?

Bailey Smith: I would say persistence. I mean, founding a company, it takes a lot of time and there are a million times that you probably want to quit. Someone that gets up every morning and recommits to the whole endeavor, that’s super important.

Poornima Vijayashanker: Yeah. I like that a lot. Those are great traits, so persistence and being persistently challenging. Very nice. Anything else you’d like to share with our viewers today?

Anne Wootton: Sure. We’ve talked a lot about Pop Up Archive, we mentioned Audio Search, that’s our newest project. It is a full text search and discovery engine for podcasts. We’ve collected a lot of data about podcasts in one place, we’re building intelligence around it, so you can search podcasts by people, topic, find related shows and what people are talking about on the internet.

Bailey Smith: Yeah, and you can go to Audio Search and check out the tools and if you go to the developer.audiosearch, you can play around with API.

Poornima Vijayashanker: Nice. Wonderful. Thanks for sharing that. Just to quickly recap, we’ve covered a lot around co-founders and how to solidify the partnership, but it basically all boils down to communication. We’ve talked about how it’s not enough to just talk to each other, you really want to have a framework for how you communicate and sometimes you need to have a neutral third party to facilitate that conversation. What that looks like is you start by maybe talking about things that you have a difference of opinions. The second is that you start to understand where the other person is coming from through using empathy. Then the third is also incorporating your teammates and communicating with them as well. Thanks again to our guests, co-founders, Pop Up Archive, Anne and Bailey for joining us today.

Anne Wootton: Thanks, Poornima.

Poornima Vijayashanker: Yeah.

Bailey Smith: Thank you.

Poornima Vijayashanker: You are welcome, and of course to you, our viewers for tuning I today and to our sponsor, Pivotal Tracker, for helping us produce this episode of Femgineer TV. If you’ve enjoyed this episode of Femgineer TV, then please share with your friends, your teammates, and your boss, and let us know in the blog comments below what you enjoyed about this episode. Subscribe to Femgineer’s YouTube channel to receive the next episode where I’ll be hosting a special guest, Pauly Ting who’s a product designer. Thanks for tuning in today and I am looking forward to reading your blog comments.

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