I took what must be the most circuitous route to becoming a founder of an internet startup ever.

I didn't learn to code (until very recent efforts), I didn't study computer science or any form of engineering. In college, I studied International Relations with a focus on the Global Political Economy. I second majored in Spanish. I went on to law school and concurrently completed a master's degree in public administration. As you can tell, I wasn't really on the path to becoming the founder of a technology company. However, I've always had an entreprenuerial mindset. I went into my studies fully intending to start a non-profit in focusing on international economic development.

During the summer of my second year of law school, I was given the opportunity to do research on a project to improve direct aid to post-conflict countries for the Center for Strategic and International Studies. Our group was putting together an "ideas bank" for out-of-the-box, innovative ideas for how to achieve important direct aid initiatives. A major problem is lack of security to deliver aid in these environments. After coming up with a couple of ideas that were not quite inventive enough and being inspired by my colleagues' research on delivering low cost, sustainable public lighting solutions and for aid delivery kiosks, I had an idea! I drafted a plan for using technology to improve access to justice. I won't go into too much detail, except to say that it got my gears turning to think of other ways to boost rule of law initiatives.

The Genesis of Yooris

I had an idea for using a social networking platform to build a collaboration tool to connect legal professionals in diaspora communities along with law students in the developed world to legal professionals to provide support in handling of cases given the heavy caseloads and crowded dockets that are prevelant in countries with too few legal professionals. The value proposition for those who volunteered their services would be to allow law students to use some of their limited hours between classes and coursework to gain practical experience doing short research and writing assignments to assist overworked attorneys abroad and to allow lawyers and firms to meet their pro bono hours by supervising these law students and lending their expertise.

Armed with this idea, now I just had to figure out how to build it. I, of course, went to the Internet! I researched already available software and nothing seemed to fit what I envisioned. Eventually, I came across an open-source social networking solution that I thought I might be able to implement. I was lucky enough to find it before they held their annual conference, which was at Harvard University. I drove out to Boston and attended the conference, trying to catch whatever information I could before it flew swiftly over my head. Afterwards, I was asking everyone questions and trying to figure out if this is something I could do. I was in one of those informal circles of conversation that form after a conference before everyone heads to the bar. I mentioned my idea and that I might learn to code so I could implement it. Looking back, it's somewhat disconcerting that most people I spoke to warned that it would be difficult (of course) and suggested, in the subtle way you suggest to a stranger, that I might be better off not learning to code. Fair enough.

Fortunately, one of the people I struck up a conversation with happened to be a young entreprenuer from Germany working on a collaboration tool to allow law students to connect to do research and share their publications. I knew I wanted to get involved because I would be able to learn along the way and could see it being used to accomplish what I had in mind anyways. Even more fortunately, they (he had a cofounder back in Germany) wanted me to join in this endeavor because I had domain expertise as an American law student (the U.S. was the target market). I became an equal cofounder to help make this startup happen.

We worked remotely using email to communicate. I put in a crazy amount of time to gather information, researching the market, discussing what the product should look like, what features to include/exclude, etc. We put together market studies, mapped out our competition, discussed what existing companies could potentially be partners, thought about our customer acquisition strategy... we were killing it. There was just one problem. We never shipped. We were doomed from the beginning. We had too many features in mind and so little focus that it was simply impossible to build a reasonable prototype, let alone a minimal viable product. We committed the rookie entreprenuerial mistake of trying to solve every pain point your target user has without actually solving any. We apparently had never heard about minimal viable product, or if we did, we didn't act like it.

This startup, which we had given the name Yooris before the name even mattered, died in complete anonymity in the early Spring of 2010 after we had worked on it since August, having decided that the players in the market were too big to go up against. Looking back on it, if we had focused and built an MVP around the most compelling value proposition of connecting law students to opportunities to get experience, we may have been able to build something meaningful.

Quentures: Coming close, even with a terrible name.

We went our separate ways after that, or so I thought. I got an email about a month later from the cofounder I met at Harvard. He asked me if Quentures was a good name for a startup. I asked him what the startup was about. He replied with something along the lines of "an app to gamify real life adventures." I had no idea what he meant, so I said "Yeah, sounds okay." Stupid.

A couple months later, I would be asked to join this startup since we had worked well together in our previous startup, even if it was an utter and complete failure. I would handle business development and marketing on the U.S. side for this new app. Sure, I could do that. Wait, no. Nope, I've never done anything like that in my life. Lucky for me, they were about three months out from actually launching a private beta, which gave me about two and a half months to learn everything I needed to know about whatever it was I was supposed to be doing. I started reading every startup blog in existence and listening to every Stanford eCorner podcast. This time around I knew I couldn't rely on domain expertise, which was a very good thing. The most important thing I've learned through startups is that you have to be a quick learner since you're almost never doing the same thing two days in a row. Luckily, I am a quick learner and tend to obsess about whatever it is I am trying to learn like it's a shiny, new toy.

Through this regimen of hyperactive study, I learned more about startups than I had ever known before and I felt more equipped to be part of a startup than ever before. I was able to make important connections to potential investors, to network with other entreprenuers and find people that were interested in signing up for the private beta, all while working insane hours doing document review at a law firm down south (although listening to podcasts while I worked allowed me to be slightly more judicious with my time).

Eventually, we had a private beta up and running with about 200 users assembled mostly through our own networks. It was cool. It got compliments. Although it was cool, we had a hard time adding new users and gaining traction. The idea of the app was to allow users to share activities with those around them so, if they're bored, they hopefully can find something to do and meet new people. The problem with this sort of app is painfully obvious and we both knew it and felt it. It required a high user density, something we had planned for. I had developed a "bowling pin" strategy to open up the app to one university at a time and had also envisioned an idea for unlocking your campus if you could get enough preregistered users on your campus (this is before we knew about Yobongo. Kudos to those guys for actually pulling this strategy off). Of course, by getting preregistrations from friends, you would earn 'points.' No big deal, right?

Wrong. I managed to make some really significant connections with my own university (Syracuse) and with a college in the heart of Boston. I had a meeting with people at my university with the power to sanction and promote the use of our app on campus. I gave an empassioned pitch for why it was awesome and how it was going to change the world... and it could all start right here, folks. See that? See what I did there?

Well, they didn't. Instead of reaching out in support of their newly graduated entreprenuer and lending the resources of the University and the community, they basically rang the death knell that they must've borrowed from a VC... "We think it's too early and there's so many new apps that we like to see how they do before we put the University's support behind them." Ouch. Okay. I'll just go get another school that I have no affiliation with to join up. That should be real easy after being rejected from my alma mater.

And, surprisingly, it was. I connected with a social media professor, David Gerzof, at one of the most hyperactive social media colleges in the country, Emerson College. I wrote an email just to see if we could promote our application on campus. He went one better. He teaches a class where startups are matched with a group of students to come up with a social media strategy to promote our app. RunKeeper is an alumn of this program, and the campaign they came up with for that was brilliant. They did a wonderful job with ours too. They promoted our app across campus, got people to join, came up with a cool viral video to promote our app on YouTube, but we hit the wall. We didn't add users fast enough on our web app and our iPhone app wasn't released prior to the end of the academic year, so our userbase was gone before we could really get them to come back and get hooked on our real value prop, connecting with people wherever you are on the fly. Our timing was terrible. So, we pivoted.

Introducing Liquid Labs!

Our CTO is some kind of algorithms wizard. When we were working on Quentures, he built (maybe overbuilt) a recommendation engine that would not only recommend things to do based on your interests (pulled from Facebook and other sources), but also learn your interests over time based on your activity using Quentures to improve future recommendations. He also built an NLP engine to pull interests from status updates.

We decided that we would release Recommendation API using a SaaS freemium model similar to SimpleGeo (hindsight is 20/20, eh?). Around the same time, our CEO attended a conference in Montreal. He spoke with numerous startups and got the impression that there was a need for access to NLP capabilities at numerous startups, so we were going to release an NLP API too.

We also realized that we had to have some sort of product of our own focused at a big market in order to attract VC money, which was in line with our goal of building something with a significant impact. Everyone was stumped even though the answer was right in front of them, but to me, the answer was obvious. I said we should just build an enterprise solution in order for companies to be able to keep track of their data. What we came up with for an actual product, though, was bigger than anything we would actually be able to build with our small team. Oops.

To make things more complicated, we were meeting with a lot of VCs and potential customers and didn't have anything to demo. So our CTO got the idea for a browser plugin that could summarize long web articles to minimize time spent reading (TextFlight). It suited our purpose and demonstrated to VCs and the like that the underlying technology worked, and we could then explain the more significant applications that could be built on this powerful technology.

This was good enough to get some important people interested, and we got a seat in the Critical Mass space in the Cambridge Innovation Center on a "golden ticket," meaning a VC firm was paying our way.

So, we still had this elaborate solution we would never build. My CEO and I were the only ones in the U.S. (the other two guys stayed in Germany except a brief two week visit to meet with VCs and such). We decided we needed a simpler product. So we brainstormed a few ideas. We were also entertaining conversations with potential partners for an e-discovery solution and for a tool for publications that would summarize content into abstracts for editors.

Our own product ideas were a tool that would aggregate and summarize online content based on the user's interest and learned behavior, as well as an idea for a cloud solution that could automatically organize your files according to topic matter. We did mockups of both designs and thought that the latter solved a more important, more prevalent problem. We could also build it out incrementally using the Google Docs or Dropbox API and then adding other services along the way. It's a good strategy.

Unortunately, the semester in Germany starts in October. Both our CTO and Head of Engineering decided that they needed to return to school and couldn't work full time on Liquid Labs anymore. Our CEO has stayed with me full time in Cambridge the whole time. Right now, we're in a position where we need not only a programmer, but somone with a background in machine learning and NLP to make this work. It's a tall order.