“Because Kyle and I have worked together for so long, our professional relationship is sort of frozen in an emotional maturity of ten years ago.”—Aaron Gotwalt

Aaron Gotwalt: Co-Founder, CoTweet, Seesaw, and Everlapse / San Francisco CA

“because kyle and i have worked together for so long, our professional relationship is sort of frozen in an emotional maturity of ten years ago.”—aaron gotwalt

Can you riff on your background with startups?
I left my job at an ad agency in 2008 and moved home with my parents in Lancaster, PA to do consulting and pay the bills. I had this crazy idea that I was gonna build this stupid fashion app on Facebook—it was going to <reverb> change the world </reverb>. In the process of building it, I worked with a friend of mine, Kyle, who was also still in Lancaster at the time. We first started working together around 2002. He didn’t go to college at all. Kyle is one of the best designers I’ve ever met. He is extraordinarily intuitive. For him, design starts with pencil sketches and translates into exquisitely crafted HTML and CSS. If you ask him to theorize his way out of a bag, he can’t. If you ask him why he’s doing things, sometimes he can’t explain it. But he’s really good and we’ve been in a very long-term partnership.

The Twitter thing was sort of happening at the time, and we were using it to promote our fashion app. In doing so, we figured out that there were some real basic problems with using Twitter to represent a product or team. So we decided to build what I describe as a “palate cleanser.” We spent three weeks building something totally unrelated, curious about what would happen. We built what became CoTweet in that period. Kyle and I very quickly realized that there were companies who were trying to buy us out, but we didn’t know how to talk to companies and sell them stuff. That’s when my friend Jesse, who works that angle better than anybody I’ve ever met, offered to help. We started CoTweet in November 2008, raised money in June of 2009, and moved out to San Francisco a few months later.

We hired an engineering team and built a really solid product. Huge brands like Ford, Microsoft, JetBlue, Coca-Cola and others all used it. We quickly found ourselves needing more money to keep building and growing and found ourselves deciding between raising another round of financing or selling. We had a really flattering offer from ExactTarget, and we decided to take it. In retrospect, perhaps the best decision of our collective lives.

It was a strange transition though—our fledgling seven-person team quickly became part a 600-person company. Their IT department was bigger than our original company. Since we delivered a lot of product in such a short period of time, I think they thought that we were bigger. For all of their best intentions, they would say things like, “Hey, we need this to be in Japanese.” So then everything that we were doing would stop, and we would spend two months trying to convert the thing to Japanese because that’s what they wanted and they had no idea of the level of complexity to do that versus to do something that’s actually interesting.

From my perspective, it felt like the product stopped moving forward at the exact point we sold it. It’s interesting how much we accomplished in less than a year leading up to the sale and how little we accomplished in the following 16 months, even when we had much more resources to play with, and despite our best efforts. We had a much larger team, but things got slower and slower. There’s a hustle or drive when it’s your thing and you’re trying to make something. But it’s really difficult to get that out of other people who aren’t as super passionate. I also think that we really struggled to transfer ownership of things, because I had the best and the worst part of being obsessed with my product. I broke up with my fiancé right as this whole crazy thing started, and I think that I channeled all my potentially destructive forces into building things. I came out to San Francisco, worked 80 or 90 hours a week, had a really nice apartment that I never really saw, knew nobody, and felt really isolated. Selling the company for what was a truly life-changing amount of money—just so we’re clear, I’m still Silicon Valley middle class—just was not satisfying. I was manic. It’s a miracle I didn’t get into drugs at the time. The company was something that I ate, breathed, and slept. I still wake up having dreams about what I was going to work on the next day. Few others in the company were like this, except Kyle and Jesse. It was really hard to get anyone else to think of it as more than a day job. And that was really difficult for us, both from top-down pressures to sell more and a personal drive for new products being thwarted. So Kyle and I did our 16 months of earn out there, complete with the startup office excesses of big stereos, a drum kit, guitars, and amplifiers.

I spent about a year afterwards trying to figure out which way was up. Kyle moved back to PA and bought a castle in Lancaster. We’re now doing the “remote thing.” He comes out here about one week out of every month.

Then one day, Jesse called with an idea that later became Seesaw, a collaborative decision-making application. I was never really interested in polling. I don’t care what 14-year-olds think is cooler: a Ferrari or Lamborghini—it just doesn’t matter all that much. What does matter is when you’re at the shampoo aisle and you’re overwhelmed by choice. If I can build something that will always help a consumer pick one brand over another, then I’m actually building an interesting business. That was sort of the thinking behind it, and we raised a lot of money, which was super easy. But we quickly found out that it was stuck somewhere between a utility and entertainment. While we had a lot of Ferrari or Lamborghini stuff, it was also really hard to get people to use it the way we envisioned. For instance, when you’re trying to make a decision, and you haven’t made a decision yet, there are only two people in your life who matter: your significant other and maybe the resident expert on said topic—but that’s kinda it. You don’t need structured data and 400 opinions. People used it more when they were looking for affirmation of decisions that they already made. So we had a lot of, “I just bought this shirt, isn’t it cool?” And you always want to answer, “No.” But people are surprisingly positive in that kind of scenario.

Our investors were super supportive despite the result. Kyle was sitting back in Lancaster at the time when he had this alternate idea for a product called Everlapse. It was like a collaborative flipbook, but with some cool onion skin. The thought was that it would make the barrier to participation really low, because you didn’t have to take that perfect photo. It could just be a circle, so it allowed you to just go and do something. It was fun and our team loved building it. It didn’t do poorly, but I think it made me realize that the market for consumer social startups gets exponentially harder every month. There are so many things competing for peoples’ attention.

When CoTweet happened, Kyle and I initially built it, but Jesse came in super-early to run it, and so that created an interesting set of internal politics. I think Jesse felt (sometimes rightly, in retrospect) like I undermined his authority as the CEO. There never really was any malicious intent, but I can see now how that probably took place at times. So we tried to align things a little bit better in the Seesaw experience. We worked really hard at it, but I think that there was tension in the team and the shuffling of roles. It didn’t help with Kyle always being remote. One downside about remote collaboration that I found, is that the subtle communication and dynamics of in-person communication get lost, even with video calls every day. For instance, sometimes you’re left wondering whether this person is disagreeing with you, or are they a bad human being? You don’t know. And you know in the back of your head that this person has never been evil to you before in the ten years that you’ve known them. But on the other hand, maybe they’re starting now.

There was one moment at CoTweet where Kyle had just flown in, and we were arguing about something. We walked from my house for a mile, screaming at each other, and it wasn’t good rhetoric. It was like, “And, you’re an idiot and here are the 12 reasons why.” We got to this Chinese restaurant, walked in, and had beer and food in silence. Then the argument picked back up once we walked out of the Chinese restaurant. We are fine now on the other side of it, but because Kyle and I have worked together for so long, our professional relationship is sort of frozen in an emotional maturity of ten years ago. It’s really comical on some level, and on another level it’s really destructive for other people because we’ll have these ad hominem attacks floating in otherwise rational professional conversations. When I hired a whole new team for Seesaw, they worried about things like, “Are you going to point those guns at me next?” which was completely unnecessary. Anyway, Kyle and I figured out that we’ll have these terrible arguments but will be fine. Even in these sometimes tense relationships, we’re both on the same team, trying to solve the same problem, trying to get the correct answer, and we’re willing to be wrong.

In between that stuntedness, with Kyle, Jesse, and I being separated, we tried to figure out how to act a little bit more like adults. We actually hired a business coach to help mediate the tension that built up between us. He had all of these frameworks and handwaving ideas that we all kind of laughed at, but he actually really helped. We did a couple of mediated talks to verbalize frustrations in a more productive way. They weren’t easy, but I think we’re all friends at this point because we went through them. It’s amazing how different your own perspective can be from the actual reality of the situation.

That brings us roughly to right now, where I’m starting something new, with a totally new team. I’m having fun working with people that I’ve known really well, but haven’t worked with professionally. I’m probably going to continue working with Kyle, just maybe not on my foreground projects. We work really well together. I tried to work on something without him one time, and it was like not having an arm. But I also think there’s something really healthy about a little professional distance, where you don’t have this body of experience, both positive and negative, to draw upon on a daily basis. The negative side of being too close is that when you’re in conflict, you’re not just dealing with the moment, you’re dealing with all that extra baggage. I think that any suitably interesting career is pretty high tension, and when the stakes are high enough, there will always be conflict. But having a relatively newer professional group, means having different perspectives, but it also means that I can’t cheat on those conflicts. For instance, with Kyle, I draw on both the positive or the negative to affect the outcome. It may not have been constructive objectively, but it solved the problem, so it was hard for us to change that behavior because it worked. But I wouldn’t recommend that to anybody. New people have the ability of forcing you to work fresh and act like a grown-up, or at least varying definitions of grown-up.

How do you choose your team?
A good startup team is a function of time and money. Our high point at Seesaw was eight people. At Byliner, we were roughly 30. The reason why I brought people from the East Coast, and people that I’ve known for a long time, was really just a supply and demand issue. There is so much demand at an early stage, and it’s very hard to find qualified engineers to do things, so often times it’s just easier to pull from your social network, and figure out who is available and who can do what.

By way of comparison, I interviewed down at Yahoo and went to see the head of engineering. This guy was not cool; he wanted me to play the algorithms game with him. He’s the kind of guy who’ll say something like, “Show me how smart you are using a white board.” But like, I make things. I Google the answers when I need to. Anyway, he asked a really interesting question which was, “How do you decide to hire somebody?” And I said, “Well, you know, we share backstories and I ask a whole bunch of out-of-professional gambit questions. I like to talk about Us Weekly among other things. I like to get a feel for how they respond to complete curveball questions. What I’m looking for is how are they going to be under stress?” And this head of engineering guy at Yahoo explained, “No, you don’t understand, we have an infinite supply of people who want a job here. How do you decide who you want?” He said, “Be efficient. Make an algorithm.” And I was like, “I have no idea how to do this.” But now I understand the answer that he was looking for, which was to develop a test, and hire the ones that pass and fire the ones that become insufferable after the test. That is the correct answer to his question. And I guess that is the luxury response to companies that have people falling in the door. However, for earlier-stage companies, that is a little harder. Also, that early-stage thing is also a function of economics, where there’s simply too much money flowing into new companies. There are all of these companies that have $1 or 2 million to spend, but there simply aren’t enough people to build their stupid ideas. People may be very difficult to work with, like me, and have really brilliant ideas, but not as much disposable money, so hiring people from your social network makes sense.

There was a point where agency life was “the thing,” and it was trendy to want to make a startup. I have a bunch of ad agency friends, IDEO-type people, and they usually become lifers. I think IDEO represents an alternative to academia, but it’s not quite the real world. They make you design things that are interesting but totally not commercial, and it was never going to be a commercial product. You know, like in a world where you make tea without using water—that sort of thing. It’s interesting to watch people like that try to make the jump because it’s very trendy to be in startups right now. The IDEO kids will come out after three or four years of completely impractical work and try to jump into something that is usually extremely practical and less comfortable than where they were. All of a sudden, they’re a senior designer and they’re cleaning the toilets. It’s a weird mix of responsibilities. San Francisco’s a big ad world, and we have a lot of ad agencies that have significant investments here, but these folks also have a hard time making the jump from changing clients every few weeks, to investing their soul in doing something that may or may not work.

What is the division of labor and its impact?
I qualify people as either “product people” or “not product people.” Meaning, there are types of engineers who don’t care what they’re working on, they just want it to go extremely fast, and the context is irrelevant; they want something algorithmically challenging. These people are the pixel pushers who just want to make it perfect, and they get lost in the obscure details, but they don’t consider the larger context. You need that kind of person as the company gets bigger. You need worker bees. Worker bees are effective. They get things done and they don’t ask questions.

On the other hand, early on you’re not sure what you’re building, and if you don’t have a lot of people asking constructive questions, then that’s a real challenge. How do you bring together a team of under ten people, where most of them have opinions about the product and business that you’re building? How do you get them to get along? How do you build an authority structure that isn’t entirely destructive? How do you manage that conflict? At that stage, what you’re building could turn into anything. Twitter is now like 2,500-ish people, but I knew them when they were 18. Now, I think there are only two or three people left from that original era, who are still with the company. What happens is, your purest, true believers, your product visionaries, the people who are creating that, “perfect brand,” tend to get disillusioned with the product as it becomes more about optimizing and making the ads work. You want all of those product people in the room for as long as they’ll survive each other, but you sort of have to go in admitting that it’s probably not a long-term thing. As you become a larger company, you need middle managers to deal with scale, and you need drones who do stupid things because that’s what they’re told to do. They are there because they get paid well and the perks are good, not because they have some over-vision of this thing that they’re trying to make. They are very different kind of people.

How much of it is idea versus execution?
What is inventing? Everybody around here has ten billion good ideas, right? Your ideas don’t matter. Some people are really weird because they walk around and before they’ll tell you what they’re working on, they’ll force you to sign an NDA. But ideas are so cheap, and execution is the whole challenge, right? You can shout an idea with a megaphone but nobody else is going to do it. Since Seesaw, I’ve had about three or four fundable ideas, but the execution turns out to be impossible. You start with an idea and everything becomes an extrusion of that, an extrusion of your philosophy. You want to make the core experience really good and avoid adding shiny buttons that don’t do very much.

It’s important to recognize failure, and move on. If I were to review how Seesaw went, I think that we should have recognized that it was failing sooner. If we had been less committed to the core idea, we would’ve had more time. We probably would’ve been a little less emotionally invested, and said, “That’s cool, but no.” Then we could’ve found something else. The economics make a lot of sense, right? In the early stage, you’ll raise a million bucks to figure out your idea. Which sounds crazy, but it’s not once you realize just how expensive it is to live out here. Anyway, you raise the money, then screw around trying to figure out something that has a business model. You look for a hint that there will be revenue flowing. The early stage feels completely insane because it looks like there is no interest in the money side of a business, but the goal is to move very quickly by getting an audience to test your ideas. Then you get to that point where you figure out where the revenue is and adjust from there.

What makes for a good collaborative startup designer?
Pragmatism is a really big part of it. You don’t need to be an expert on CSS or HTML or whatever. What you need is to be smart enough where you can learn faster than people get frustrated with you. One of the great things about Kyle is that he’ll have an idea, we’ll talk about it, and then he’ll go and build a working, applicable prototype. We tag-team back and forth. We’re like the Play-Doh star-making extrusion process. It’s not just a matter of making some mockups because you can. I don’t want to make mockups. I want to make the real thing with the fewest steps in between. There is a certain allowable “just going with your gut” element where you can’t overthink. I would rather take some gambles and fix the things that we discover that we don’t like later, rather than get a perfect-looking thing. I refer to what I do as sort of like painting.

How does a physical working environment influence your collaboration?
You pretty much need people face-to-face, all of the time. Sometimes you need to take a sharp left turn that you weren’t prepared for. If somebody walks into the office, and we go out to lunch having this funny conversation, and then there’s this idea moment that changes everything about how we’re going operate, the remote person will have missed that. It’s hard to get long-distance people to work effectively together, even though there’s some great software out there. But especially at that early creative stage, long distance collaboration doesn’t work well. The best moments at Seesaw were when Kyle was in town, and we would have all these great ideas. If we had more of those times, I think we could’ve gone further.

You need physical space for conflict. There are successful virtual companies, but I think it’s hard. It also depends on the nature of your business. There’s probably some people who are really great at being passionate and virtual all the time. I don’t know how you do that.