Last Friday I was fortunate to spend 30 minutes talking with Jack Dorsey, who in addition to co-founding Twitter recently launched a product & service called Square. As an electronic device, Square is a mobile credit card reader that plugs into the audio port of compatible smart phones and laptops. As a service, Square is a downloadable application that verifies sellers and provides buyers a measure of security about the transaction itself. From small businesses to political campaigns, the potential applications for Square are virtually unlimited.
A few highlights and then the interview after the jump. Also strongly recommended: Friday Coffee with Square on Ustream
Q1: Can you tell us about inspiration for starting Square- Biggest challenge or unexpected surprise?
"The whole thing has been rather challenging because it is a new industry, something we are learning, and not just learning but learning how to simplify. That has been the biggest challenge. There is a lot of complexity in this industry and when we remove a bit of it, some more just pops up. Our focus is to build an experience that hides all that complexity or does away with it in some way. That has been a challenge to first of all recognize (the complexity) where it is and then get rid of it. There has not been any one particular thing that has really been challenging, it has been all of it."
Q2: Square is available for Apple and Android Devices. Is there something the mobile phone services providers or manufactures could do to make things easier for developers?
“It seems all the platforms are doing their best to make it easy, in particular Windows and Blackberry. They are right in the middle of a transition, they're reworking their API, their SDK to make it easy to address all their hardware platforms instead of having to program for each one. I think it will take some time to get there, but it is something we are definitely excited to participate in once they do get there.”
Q3: You outsourced the manufacturing of Square, if you had to do it again, would a domestic supplier been able to meet demand for the cost and what you needed, or was China still the best way to go?
“The only reason we picked China is because we could not find anyone in the U.S. to do it. There are very few people who make things anymore in this country, especially small electronics like that. We actually went out and tried for many months to find people in the United States to do it. Not really even considering the cost aspect, but we couldn't find it. If we do find it, we would still love to turn that on in the U.S. We just could not find anyone who could meet the demands. “
Q4: You recently sent email to Square users apologizing and explaining the delays in hardware and transaction limits. What has been the overall tone of the response been like?
"It has actually been really constructive. We do have a lot of people who are frustrated with the amount of time it has taken. And I think a lot of that is just our fault in terms of communicating in the right way what is actually out there today, what works and what still needs some work. So that’s definitely been a challenge, but I think what we learn in all these things is that as long as you are talking to people, it minimizes a lot of the frustrations and the issues. So were just intending to do a lot more talking to people and making sure that everyone has a sense of where we are with our application and with the service and what that means for everyone."
Q5: PayPal recently introduced an updated application allowing iPhone users to fist bump payments. Can you talk about what sets Square apart from that as well as past and future mobile credit card processing tools?
"In order to do the bump technology with PayPal, it does require a PayPal account, and there are a number of people who have PayPal accounts and that is definitely a clever way to go about transferring money, but it is just not our focus. Our focus is really speaking to that 90% of what people are using, they're using plastic cards. Our intention is to turn on that other side and really enable those face to face transactions with devices that everyone has in their pocket. So we see ourselves a little bit differently in that light because we do not require any sort of account to actually pay someone. You just use the plastic card in your pocket. And that is really our focus. At the same time, we want to be completely payment network agnostic, so if your really comfortable using PayPal and you want to pay with it, or you want to receive payments through PayPal, but you still want the Square front end experience, that is something we would be interested in implementing and maintaining."
Q6: 
; Act Blue allows you to donate to their candidates with a specifically phrased Tweet. There is a Facebook application called “SquareUp with PayPal” that is geared for collecting money for Facebook events. Any plans for integrating Square with Facebook, Twitter or YouTube?
"Right now were focused purely on the face to face interactions. Once you start getting more into the Internet and virtual interactions you start to lose more identity. We want to make sure that we get the face to face stuff right, because 90% of commerce is still offline, only 10% of it has moved online and we want to address that 90%. There are definitely models on how to extend that to the online and there are obvious integration points, but we are talking this bit first."
Q7: What are your thoughts on politicians use of Twitter? Is it something that is more effective on the state or local level where the representatives themselves actually respond and engage or is there a politician you know who is doing it very well?
"I am really fascinated by this usage, and I love to see it. I went over to Baghdad with the State Department in March of last year and we managed to get the Deputy Prime Minister (Barham Salih) on Twitter and his usage of it was really, really inspiring. It was very frank, it was very direct and it was very transparent and it was him directly. I think in terms of other politicians in the U.S., I am most impressed with three Mayors: Cory Booker of Newark, who has really taken to all these technologies, including Twitter to talk about the issues that his city is facing. He is a champion, he is out at 3am on police beats, walking the streets, reporting. And most importantly, he is replying to people, and he is replying to people in real time that communicate with him… He has been awesome. Mayor Mike Bloomberg has also gotten into it a lot more. He used it very heavily during his campaign run and has started back up in using it during in day to day, which I am really excited to see. For a city like New York it just creates a lot more transparency and connection to, someone who is often removed from the normal citizen's particular day to day, so now he is a lot more approachable and accessible. In my hometown of St. Louis Missouri, Mayor Slay has been using the technology extremely effectively. He has really funny and clever Tweets, but he also really engages the St. Louis community and replies real time. (He is) using it as a way to point out very interesting things about St. Louis that normally people might look over.
Q8: Earlier this month at the Personal Democracy Forum, there was some speculation about the impact of Twitter if it had been around on September 11th. I recall you mentioning that there might be some instances where instant communication like that might be a negative, so I was wondering if you had any follow up thoughts.
“It’s a really good question, and I honestly don't know what effect Twitter would have in that situation, if any. My particular worry, is that the one thing I was really inspired by after 9/11, especially in NYC is how people gathered and really sought each other out face to face. People were just walking the streets and it really united the city in a way no other event has ever done. My concern with relying on the technology would be that it would potentially abstract some of that humanness, and kind of make it a little bit easier not to go out in the streets and not to go out meet your neighbors and really support each other. I think that was a defining moment for NY, New Yorkers and thereby rest of the nation. That would be my only concern in introducing a technology like that…. Certainly technologies were used at that time, IM was huge, and we definitely had cell phones, but I think the most important thing in that situation is that people left their technologies and really focused on their face to face interaction.”
Q9: Is there a particularly surprising or innovative use of Twitter you have seen? Any thoughts on self described ‘gurus’ or social networking ‘experts’ using automated tools to follow tons of people?
“I am surprised everyday on how people use Twitter. There is a different account that springs to my attention on a daily basis. I have a rotating set of favorites but on the latter point, I think any sort of automation or any sort of aspect like that really takes away from the spirit of the technology which is to really share what you think, what your experiencing, what is happening around you, and when we get into more and more automation we get back to these abstractions that Twitter effectively removes. So I don't really appreciate that sort of automation. I think there is a lot of people in the social media space that are trying to consult against that, and I am fully supportive or that. And being more of an effective communicator, using the technology, using the constraints, but it changes on a daily basis.
Q10: What is the best Twitter analytics tool for tracking reach or ranking users?
“I think it is wide open right now, I can't say I have spent a lot of time looking at firms doing that just yet, I think there is something there and it needs to be done. I don’t know who is the strongest at the moment or even what they are looking at, I think it is one of the most fascinating things of Twitter is getting an understanding of reach. There is a lot of work there and it is going to be coming from a lot of different folks. Not just one in particular, so I am excited to see what people come up with."
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