Freeing Data to Organize People - Interview with Isaac Holeman and John Wagner from Squarepeg

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A discussion with John Wagner and Isaac Holeman from Squarepeg about their vision of a world of de-siloed information that finds its way to the people who want it the most. Followed by a discussion about why there's no good reason that a 21st century start-up shouldn't create social benefit as it creates wealth.

Jed Sundwall: Tell us a little bit about yourselves and what you're doing with Squarepeg.

Isaac Holeman: I am heading into my senior year at Lewis and Clark College. I'm a biochem major in pre-med. I've been working on Squarepeg for a while now, started back when John and I were roommates back in the dorms. And right from the very, very get go, John had a lot more of a background in technology and especially web design, development and stuff like that. And I'm an activist, I'm quite active. We'd be just discussing things with each other and what works, what doesn't, how do you engage people on the Internet?

And as soon as the ideas we were talking about started becoming a project, forming into a project, my realm was everything not development, so everything from thinking about organizers and the tools they're going to want and going to need and the experience for them and how to market this product and how to create an organization that actually could bring it to people in a timely manner. Organizing, all that work has been what I've been sinking my teeth into.

John Wagner: And for me, I've been handling the flip side of the project, which is—as Isaac does the footwork for how does Squarepeg connect into the community, where do we fit in the bigger picture of activism, both in Portland and in the greater picture of things—I've been working on developing the technology that is actually Squarepeg. I'm a senior at Lewis and Clark as well, and my background is in psychology and design and development. I have four years of professional development experience. And then, my interests revolve around how people process and interpret data on a base level of psychology. That really informs a lot of my development process and my design process, that kind of thing.

SoFrom the get go, Squarepeg was a bit of almost like a really interesting puzzle for me. We have all this data about activism, about how people want to connect with one another, etc. So, what's the best possible way we can get that data to people and help people manage it? I come from a strong interest in activism, as well. That's part of what initially made Isaac and I good friends, was a strong commitment to the community. Using that data set, that activism data set as the base for me to play with this concept of how people process data is really what makes me really excited about Squarepeg.

Squarepeg has gone through a couple different evolutions. As Isaac said, we've been mulling this idea over for a very long time. We only entered active development rather recently. Almost immediately after we entered active development, we had an experience that fundamentally changed some of the things that Squarepeg was designed to do.

At the outset, and I'll let Isaac say more about this in a minute, Squarepeg was designed to be a location social network that allows people to connect to one another, as well as sort events, action, activism data within local communities. It was going to be another social network that was based solely around activism data. It was kind of a clean slate. You weren't on Facebook anymore, competing with frivolous data, in order to do activism and organizing. You were in a completely separate space, working with that data. Isaac, do you want to say more about that?

Isaac: Yeah, the way that I like to talk about it is that we started out, just recognizing a few problems. And really in the beginning, there were three. One was that we hadn't seen the environment we were looking for to engage people online, different reasons, different things going on in some of the change-oriented sites, versus the large corporate networks like MySpace and Facebook. We hadn't seen what we felt was a really ideal environment for engaging people. We wanted to replicate that environment.

Problem number two: we were really frustrated with the way information just dies and gets siloed and trapped in these networks, whether they're the change-oriented ones or the not change-oriented ones. We wanted to be part of this open data movement that's putting them into that. And when people put data on the Squarepeg destination site, we wanted to be able to send it other places, without those people having to put their joints, retype in the data over and over.

And then, finally, once the data's flowing, it creates this huge problem of the information being copied over and over. And it just becomes a phenomenal amount of information. We wanted to look at some ways both with the interface and with the underlying technology, to help people sort it all out: what's fine, what's going to be useful, what's going to be really actionable for them.

And like John said, we had this big change, and that happened at the NetSquared conference this last year, because as much as we're pulling on our own experiences and our own frustrations as activists, we're really all about learning. We're a community of people who are working in these areas and figuring out what they want and what they need, what's going to be practical, in addition to best case scenario. And people are really most interested in what we were talking about doing, addressing the last two problems. Why is data getting trapped still when we have the technology so that it doesn't have to get trapped as much?

And, too, once the data is moving around more freely, we want to figure out how can we help people find meaningful ways to sort it out with recommender systems.

We're a small enough team that we're still really agile. The core ideas were still there, but in terms of the way we were implementing them, it was a pretty big shift for us. And we basically did that over the course of a few fingernail-biting days, and just like, "Yeah, I guess this is what we're doing, then." And since then, people have been more excited than ever about our work, and it's been really heartening. We've been making a lot of progress.

Can you describe for me what your ideal scenario is, especially with regards to data getting siloed and lost within like a certain network? In your mind, in a perfect world, what would be happening instead? Walk me through an example of somebody posting about an event or something.

John: Ideally, when someone posts on an event or an action that they want people to take, they don't have to spend an incredible amount of time devoting their own energy just to getting that out there. In a perfect world, activism is going to be less about finding the tools to organize and more about effectively organizing and actually connecting with people. So, with that as our goal, best case scenario, you're using a tool like Squarepeg, you post an event or an action on one place: on our site.

And then, that would get replicated transparently to social networks, but only to people who have an interest or who we think will have an interest in that event or action, so that, basically, you aren't doing a ton of extra work. You, the organizer, aren't doing a ton of extra work to repost your event on all these social networks. And, you're getting the added bonus of a recommender system, helping you to choose which people are actually going to be interested in following up on your event or action, so you're not wasting time contacting too many people, you're not contributing to that vast amount of information overload, people getting updates and bombarded by information that they're not actually interested in.

So, in a perfect situation, we'd see, basically, a pretty straightforward transaction from an event being posted on a site like Squarepeg, and then, distributed to all the major social networks, to people who will find it interesting.

OK, and now, what if they didn't post it on Squarepeg? What if they posted it on Facebook? Are you doing work to get information out of those silos, as well?

John: Yeah, we are.

Isaac: We'd like to, and let me take a slightly different approach on that perfect world question. John told you a lot about what the first stage of Squarepeg is trying to do, what's in our immediate game plan. Here is a broader picture about what might happen with social change and with the Internet in the next who knows how long? Hopefully, sooner, rather than later. I have this crazy persuasion that there's a fundamental difference between the social sector, people who are using the Internet for social change, and the corporate sector. In the corporate world, you can develop as much technology as you want, but when the business logic isn't there, stuff gets log jammed.

We have the technology to make data open. We don't have the business models for the corporate world. We're getting there, but it's going really slowly. But, I have this crazy hope that in the social sector, by and large, people are going to say, you know what, we don't need to make a profit. And if we can figure out the technology that's going to help people change the world more effectively, then we're just going to do it, and actually maybe even lead the way where the corporate innovators are failing, are getting stuck in the business models and the profit margins.

What that can look like for open data, I might be able to just go on the Internet and I have a place, whether it's Squarepeg or another site that crops up in the near future that I trust, and I've chosen to give them data about me that effectively expresses my tastes, my interests and my areas of expertise. And then, when someone posts an action or an opportunity or an idea that's highly relevant to my tastes, my geography, my areas of expertise, I'll know about it and I won't have to be on the right site or I won't have to go searching, searching and browsing through. I'll just be notified about it in whatever way I've chosen on my Twitter or my e-mail, my blog, wherever.

And the same, if I have an idea, all of a sudden, I decide, you know what, One Laptop per Child isn't working for me—we're going to start one cell phone per child, I'll be able to go out on the big, broad Internet and because maybe a whole ecosystem of services are understanding people's taste data and I'll be able to find who's been talking about cell phones for development and this kind of thing. I'll be able to find them efficiently. I'll be able to sort out who is being listened to more than other people. I'll actually be able to find them and get down to the nitty gritty of doing what I'm trying to do. That's like the bigger picture.

Part of that eventual goal definitely requires that we or someone like us crops up to pull data out of the large, social networks, out of, out of The Point, or wherever, in addition to putting it in.

And now, Isaac, you commented on my interview with Andrew Mason about the way this line is blurring between the corporate world and the non-profit world, let's just say non-profit and for-profit organizations. What makes you guys stand out in that way? Are you trying to run a for profit company?

John: Before you answer that guestion, guys, I am out of time here, I apologize. I don't know if Isaac mentioned this to you, but I'm on my incredibly short lunch break. I'm sure Isaac will be able to answer any questions about our big picture philosophy, as well as more specific questions about the site, itself. If you, or your readers, have any more in-depth technical questions, you should feel free to e-mail me at I'm sorry I have to cut out on you guys.

Ed: We missed John dearly.

Isaac:The whole for profit, non-profit social enterprise, that's the interest I bring to Squarepeg. It's areas I'm interested in learning a lot more in. I don't think the for profit, non-profit distinction is very useful. I think it's outdated, and I'll tell you why. Everybody brings in profit of some kind. What that basically means is you're bringing in more money than your operating expenses. Non-profits, technically, in accounting terms, they make profit all the time. What's really relevant is who's benefiting from the value that's created by the organization? And generally, we think of private enterprises or for profits as saying that goes to investors or whoever owns it. And you say that in the U.S., non-profits are not owned by any individual, they're owned by the public. Technically, the benefit is supposed to be going to the public.

There's another distinction that's also really relevant, and that's ownership in the sense of who gets to benefit from the value that's created. But, there's also ownership in the sense that who has the legal and actual authority to choose to make the day to day decisions that are going to decide how that organization maximizes benefit and who they're maximizing it for. And traditionally, it's just private enterprises maximize financial wealth for the owners of that organization and non-profits maximize other kinds of social capital, social good for their owners. But, we're finding more and more that that's frequently not the best way to create social change.

And particularly, there are broken markets.

I have a good friend, who works in Burundi, and the average income there is less than $1.00 a day. There's really just no way you're going to get people to pay for healthcare. The Internet and social media right now, it's about as mature a market as the world has ever seen, in terms of enabling really effective competition like the free flow of ideas and low entry costs for creative people to bring their ideas to the market. It's a really effective place to create a business if you know what you're about and if you have a good idea.

A start-up is hard in any circumstances, but creating an idea that maximizes social benefit and also creates financial value is not any more difficult hardly than creating any successful start-up that doesn't cause a social benefit. There's no reason why we wouldn't because that profit and access to capital markets and stuff like that is so beneficial if we get to a point where people want us to scale up, really hit the gas and make this go big.

Where we're at, I think it is important to make the distinction. A lot of people say you can have blended value like doing well while doing good. That's a popular phrase. I'm kind of a purist. I think at the end of the day, there are a lot of situations, where you say, with this decision on this day, do we put our priority on money or do we prioritize our social impact? And with Squarepeg, you're going to see 100 percent of the time, we're going to maximize social impact, always. But we're very aware that we'll be able to do that better if we remain financially solvent, if we're able to make enough money to hire a decent lawyer and a decent accountant because we don't have all those skills or the time to do them while we're managing the other aspects of this organization.

But, ultimately, what it comes down to it, the lens we view every decision through is how does this affect our organization's ability to produce a social benefit? So, that's where we're at. The term, "social enterprise," is up for a whole lot of debate. Different people have very different ideas about it means. But, I hope that explains where Squarepeg sits in that.

A few thoughts that went through my head as you were talking, one is Google, which is an enterprise that provides a tremendous amount of social benefit. San Diego's Metropolitan Transit System has the worst website imaginable, it doesn't work.

I wanted to figure out how to take the bus, and Google Transit has it all figured out and it works really well. And I get to use that for free. And I have no idea why they feel like they should provide this service, what they get out of it, but they do and they make a kabillion dollars a day while doing it, somehow. There's number one: the idea that just because a company's making a profit in some regard, doesn't mean that its existence isn't good for society.

And then, the other thing you got me thinking about was have you ever read, The Ownership Of Enterprise?

That sounds familiar, but I don't actually think I've read it.

It's a book about organizations I read in grad school, and it's great. The guy advocates quite a bit for non-profit and co-op type organizations because they can be very effective. There's a guy here in San Diego, who runs a restaurant called, "The Linkery," and I interviewed him for my own personal blog a few months ago. He gave me the greatest metaphor I've heard regarding money when he told me, "You know, we have to make money, but the way we look at it is that money is like air. You don't go around thinking like, 'man, I love breathing this air, I wish I had more air. It's very necessary, it keeps things going, keeps you moving. You need it to live, but you don't go around thinking, oh, man, I need more air.'" And so, when you're describing you need to pay for an accountant, you need to pay for a lawyer, you might need to pay for more developers, and all these things are going to require money and profit, but that's what you treat money like, just as an essential resource and not as something to have just to have more of it.

Yeah, I agree with that, wholeheartedly. That's how I feel, personally, but also, as an organization, where Squarepeg is at, we very much understand the strategic of importance of money. And like I said, because we're working in a market and have a very available business model where we can access some money of our own, it makes total sense to access it that way. But, we're definitely not bound to try to "maximize air" when that would come at the expense of maximizing our social impact.

That's a great way of explaining it. Is there anything you want to say to our readers?

If you're following us on Twitter or our blog, we're going to start some private beta testing very soon, in the next weeks here. Once we start testing some of the basic foundations of this software we're offering, basically allowing people to have actions and events and manage those events from a few different places like our website and Facebook and stuff like that, then we're going to move on to getting more events on there, including cooperating with other NetSquared featured projects like social actions.

And then, we're just going to really focus on honing the recommender system. I would encourage anybody who's interested in checking that out to follow us on Twitter, keep track of our blog. We're pretty excited to be able to offer people something pretty soon.

There's also a place on our website,, where you can leave an e-mail address. Like I said, if you're following us on Twitter or you're reading our blog, then you're going to hear about when we start testing.