Graduate Report Fall/Winter 2011 cover
Graduate Report: Fall / Winter 2011 - E-Graduates

In the last decade, a growing number UConn Law graduates have founded or taken on top positions in businesses where the Internet and other information technologies are playing a leading role in delivering goods and services, realizing unprecedented efficiencies and productivity and, to varying degrees, replacing traditional business models. Let’s meet five graduates who are making their marks in the world of e-business.

Mark A. Cohen ’79, is co-founder of Clearspire (, a reengineered law practice that “combines advanced business practices with powerful technologies to promote excellence, accountability and value” in the practice of corporate law. Clearspire is comprised of two legally separate companies: Clearspire Law Company, for which Cohen serves as managing director, and Clearspire Service Company, which administers the business side of the company’s operations.

Rudy DeFelice ’91 is interim CEO of Kidworth (, a Web-based financial services company he founded “to help kids develop skills in saving and spending money more intelligently.” DeFelice also is the founder of and an advisor to Practice Technologies, Inc., now known as RealPractice (, a company that provides software and Internet information products for legal and business professionals.

Matthew Small ’99 is the chief business officer and chief legal officer of Blackboard Inc. (, a leading provider of Internet-based learning management systems used worldwide in universities, K-12 schools, corporations and government agencies. Other Blackboard platforms include virtual classroom technology, educational mass communication technology, educational analytics, mobile platforms, and student card systems.

Marianne Reiner LL.M. ’01 is co-founder of TransConnect Translation (, a company that provides accurate, quality legal translation services – primarily from English into French and French into English – to a “world community of lawyers,” as well as to various businesses, nonprofit agencies, publishing houses and international organizations. Currently, TransConnect has clients in the U.S., France, Switzerland, Belgium, Germany and Canada.

Jeremiah (Jeremy) Gall ’01 is the co-founder and chief operating officer of FlipKey (, a leading vacation rental Web site “dedicated to helping people find and plan the perfect vacation.” features more than 130,000 rental properties around the world, as well as “the world’s largest collection of authentic verified vacation rental reviews.”

While these five Law School graduates have much in common today, they traveled different paths to get where they are. For Mark Cohen, co-founding Clearspire followed a 30-year legal career that included serving as an award-winning assistant United States attorney and the managing director of his own litigation boutique firm, Mark A. Cohen Associates. According to Cohen, in 2008 several things occurred that profoundly affected the legal landscape, including the collapse of Lehman Brothers, the “convulsing” American economy, layoffs at law firms that had enjoyed a fifteen-year run of unprecedented growth and a challenge on the part of the Association of Corporate Counsel for law firms to do something about the broken legal system. “What you had were very unhappy corporate clients, an increasingly large number of highly qualified lawyers who were suddenly out of work, looking for work or hating their work...and certain technological advancements that made it possible for a forward-thinking organization to create a platform that would not be so brick and mortar-centric, like so many big law firms that spend fortunes on offices that people rarely go to,” says Cohen, an early adopter of information technology in the delivery of legal services. “Put all of those things together and there was a wonderful opportunity to create something that would address the broken model, a model driven by one thing – profit-per-partner. So we [Cohen and co-founder Bryce Arrowood] set out to create a company that would align the interests of the three stakeholders in the corporate legal delivery system: the lawyers who actually do the work, the law firm that bundles it together, and the clients who consume it. That was the overriding philosophy that propelled us to create Clearspire.”

Both Matt Small and Jeremy Gall began their legal careers at Testa, Hurwitz & Thibeault LLP in Boston. “I was in the corporate group during the Internet heyday, when we were doing a lot of private equity work for technology companies,” recalls Small, who earned a dual M.B.A./J.D. at UConn after completing his undergraduate work at the University of Denver. “The firm was kind of a breeding ground for high-tech in-house counsel at the time. When I learned [in September 2002] that Blackboard was looking for an in-house corporate person I jumped off the cliff and signed on. My wife, DaVina, who was practicing law at Hale and Dorr, had an opportunity to transfer to their federal contracts group, so the two of us moved down to DC.”

“At UConn I was deciding between working for firms in Palo Alto or Boston that specialized in corporate work for high-tech companies and venture funds,” says Gall, a Boston College graduate (and a new dad to Paloma Garden Gall, born days before this magazine when to press). “I decided on Boston and spent five years at Testa, Hurwitz & Thibeault helping start-ups and public companies with funding, licensing and corporate transactions. My interest in helping clients reach their business goals reinforced my drive to start my own technology company. Vacation rentals were the perfect category to benefit from new social media tools like guest reviews and a better user experience.”

Prior to starting Practice Technologies, Inc. (PTI), Rudy DeFelice spent nearly a decade at Kelley Drye & Warren LLP in New York City and McDermott Will & Emery in Los Angeles, where he focused on corporate restructuring, bankruptcy and intellectual property litigation. “I had a fantastic run at some great firms, says DeFelice, the holder of an LL.M. from the University of Exeter. “During that time I watched the world become digitized and globalized. I knew law firms were going to need better tools to live in that world. So I built Practice Technologies.”

Marianne Reiner LL.M. '01

Marianne Reiner, who was born and raised in France, spent several years in the NGO world before co-founding TransConnect late in 2009. “I worked for an immigration law firm after law school,” she says, “and then had the wonderful opportunity to go work for Doctors of the World (DOW) managing a program to help asylum seekers have access to free medical and psychological evaluations to support their asylum claims. I worked for DOW for several years and then managed another program for refugees on behalf of the International Rescue Committee. As fascinating and enriching as it was to work for NGO’s, it was also mentally draining…When my daughter, Lucia, was a year old, I decided to combine my language skills and legal training and became a full-time professional legal translator. I can now say this was the best career decision I have made. TransConnect Translation is sort of my third child.” (Reiner’s son, Etienne, was born three years after her daughter.)

Today, Reiner and her business partner, Cynthia Hazelton, run TransConnect from San Diego and Cleveland, respectively. “Our motto is ‘Translation for Lawyers by Lawyers,’” says Reiner, whose first venture into the world of translation took place during her UConn Law days when she helped translate journal articles written by George J. and Helen M. England Professor of Law Ángel Oquendo. “We provide translation services from English into French and from French into English. We also manage a team of legal translators in our language combinations as well as in Spanish, German, and Japanese.” Reiner adds that her responsibilities include translating, doing research for translation projects, recruiting qualified legal translators, elaborating marketing strategies, and accounting and other administrative tasks. “We are a boutique translation agency, which means that every aspect of our work is carefully reviewed by us,” she emphasizes. “With just the click of a mouse, we communicate with clients from all around the world. Information technology is key to our business. We use translation-specific software that ensures consistency in our terminology and allows us to manage our glossaries to better serve our clients.”

Jeremy Gall '01

Jeremy Gall started FlipKey in 2007 with two co-founders who shared the same not-so-pleasant experiences renting vacation homes. “We knew vacation homes were a great travel option, but finding the right home and renting it was unpredictable and not enjoyable,” recalls Gall. “We created a verified guest review system and a world-class service to find and book the best vacation homes.” As the chief operating officer of Boston-based FlipKey, Gall’s main task is to consistently push the company to out-perform the competition. “Part of this (involves) developing innovative traveler tools or homegrown administrative systems so our customer care team can answer support questions faster and more effectively,” he says. “It’s hard to make it alone in this world. A big part of our growth is based on successful partnerships with vendors and software providers. The most significant of these has been our role powering the vacation rental experience on This puts our rental supply in front of more than 30 million unique visitors a month – fueling enormous traffic to our listings and making us the fastest-growing vacation rental Web site.”

Rudy DeFelice '91

“I started PTI pretty much as the dotcom bubble burst in 2000,” says Rudy DeFelice. “Our first product was called RealPractice, which was based on a sophisticated categorization engine that helped large firms find and use their own documents more effectively – essentially Google for law firms. It was a breakthrough product – but nobody trusted emerging companies around that time since so many were disappearing after the bust. However, we stuck it out long enough that people realized we were serious…Eventually, we had most of the Am Law 100 on our client list…and we were named to the Inc. Magazine 5000 of the fastest growing private companies in America. I literally did everything at one point or another, from hand-drawing the first product screens on a yellow legal pad to raising venture capital, building the team, speaking at conferences, sales and customer service, and moving our products to the Web. I also did some of the legal work, but as we grew we hired my law school classmate, Joe Volman ’91, as our main counsel. Joe is a star in corporate law and was a fantastic resource to us.”

While DeFelice remains an advisor to RealPractice (the former PTI), his focus today is on Kidworth, a Los Angeles-based Internet company he launched a year ago. “Kidworth was born, in a sense, at a five-year-old’s birthday party,” he says. “Everyone showed up with a gift, which was opened excitedly then pushed to the side. A bunch of dads were joking that the kid was sitting in front of a pile of about $700 worth of imported plastic that would end up in a landfill. There was no long-term benefit to the kid…and it wasn’t very gratifying for gift-givers either. It just seemed like a broken dynamic.”

That less-than-satisfying birthday party experience led DeFelice to start thinking about gifts as a form of children’s income. So he developed a simple system that allocated some of the gifts, allowances and chore earnings of his own three children to things that would help them long-term, such as smart products, college savings and charitable giving. “It worked well, and best of all the kids got excited about setting and meeting goals and watching accounts grow,” says DeFelice. “Although I had been cultivating the idea for Kidworth in my own family for a long time, when the wheels fell off the world economy I decided that the world really needed it. So I left PTI and took a year off – much of it spent refining the idea for Kidworth. We launched a simple beta in December 2010. A day after the launch, FOX TV called and said they wanted to do a feature. ABC, Radio Disney and CNN soon followed, so we pretty quickly realized that we were on to something.”

Mark A. Cohen '79

Developing a new business model also is what Mark Cohen had in mind when he co-founded Clearspire in November 2008. “We call our work environment a 21st century workplace, not just a 21st century law firm,” says Cohen. “Basically, we have a two company structure – a service company called Clearspire Service Company LLC that provides our law firm with every imaginable piece of infrastructure that a firm on steroids could ever hope for. The centerpiece of the infrastructure is our IT platform; there’s also H.R., accounting and public relations.”

According to Cohen, when a prospective client sits down with Clearspire, a detailed evaluation is done on the client’s needs and priorities, budget parameters and which of the firm’s lawyers (all of whom typically work from home or other remote locations) have the right expertise and experience to handle the matter effectively and efficiently. “We go to the client and say, ‘Here’s how we plan to execute what we are gong to do, these are the lawyers that will work with you and this is what they are going to charge,’ ” explains Cohen, who did his undergraduate work at Vassar, where he was the college’s first Rhodes Scholar candidate. “The client gets a transparent, fixed-price fee. In ‘big law’ one-third goes to salaries and true overhead costs, one-third goes to rent and other excesses, like corporate art collections, and one-third goes to partners. We saw a tremendous opportunity to change that economic model, do away with the billable hour as the primary method of charging fees, and make everyone much more accountable for what he or she does.”

Cohen sees Clearspire as the “first real alternative” to the Am Law 200. “We already are competing with top law firms in this country and abroad for corporate business,” he says, adding that Clearspire only hires experienced lawyers from those 200 firms or top in-house lawyers from top companies. “Since our hard launch [in June 2011], we have had engagements with eight Fortune 500 companies and several foreign-based global companies, including in Singapore, Korea, the Philippines, India and the United Kingdom. We have such great geographical reach because our IT platform is remarkably scalable and does a phenomenal job doing away with geographical boundaries and constraints.”

Matthew Small '99

Since being founded in 1997, Blackboard has become the world’s leading provider of educational technologies, most notably through its flagship learning management system (LMS) platform, Blackboard Learn, which is used at nearly 6,000 higher education institutions in more than 100 countries. “We are also the leader in virtual classroom technology, educational mass communication technology [used, for example to notify parents and students about a snow day], educational analytics, mobile platforms, student card systems and support and services around academic enterprise,” says Matt Small. “We are the number one provider of educational learning management systems in every country in the world that has an online LMS.”

As chief business officer, Small has operational responsibilities across the entire organization with direct responsibility for business development, corporate development, legal and human resources. He also continues to serve as the company’s chief legal officer. “We have 2,500 employees in our DC headquarters and in offices in London, Amsterdam, Sydney, Beijing, Vancouver and Calvary,” he says, noting that Blackboard was recently sold to a private equity firm for $1.6 billion. “We are truly a global company.”

Doing business via the Internet poses challenges for each of these distinguished Law School grads. “Our biggest challenge (at TransConnect) is to convince our clients, who are spread throughout the world, that even if they have never met us face-to-face, they can still trust us and our work,” says Reiner, who adds that because she and her partner still like doing business the “old fashioned” way, they travel to meet their clients whenever the opportunity arises. “As far as security goes, we have a secured server and an external back-up system that automatically backs-up all of our work twice a day. We take confidentiality very seriously. Every subcontractor who works for us has signed an ironclad non-disclosure agreement.”

Like TransConnect, Clearspire is sensitive to client concerns about limited face-to-face contact. “We have what I would call a hub and spoke system at our headquarters in DC, where most of our lawyers live,” says Cohen, “and we are about to have a New York City presence, which will include an office. Our theory is that once we have a certain critical mass of lawyers in a particular geographic region we will open an office. The difference is that rather have 100,000 square feet of office space with a corporate art collection and all the rest we might have 5,000 square feet, if that.”

Cohen, the father of two teenage daughters, emphasizes that Internet security is essentially a non-issue at Clearspire. “Our system is much more secure than traditional law. We have a proprietary cloud, meaning that our host is a so-called Tier 4 facility, which is what large financial institutions use because they can’t afford to have security lapses. We also have a backup system…and our own dedicated servers so our data is not shared with anyone else. Not only has a client never challenged our security, we were just hired by one of the leading global technology companies to assist them with their own security issues.”

“It’s very important when you have large state institutions as clients to comply with their particular policies and state law, as well as applicable federal law,” explains Small, who lives in DC with his wife and two young sons, Grey and Gunnar. “At Blackboard, we develop our products to ensure that they comply with those regulations. It’s also very important that Blackboard operates in a highly secure environment. For some reason, the hacker community loves to attack grade books to see if they can get to everybody’s grades. We have never been successfully hacked in that way – and we host more than 1,000 universities.”

“As an online media company, FlipKey is at the intersection of traveler and supplier content, and my legal background helps handle the work this creates,” says Gall. “Early on we decided to take an open approach to user-generated content – not only helping suppliers collect reviews with our patented platform, but also publishing those reviews on their own Web sites and other distribution channels. We license content from supplier software partners and distribute back guest reviews and/or rental listings. We have to strike the appropriate balance of letting content live in the wild while maintaining brand control.”

Letting content “live in the wild” also is a concern of DeFelice. “The most obvious challenge (of doing business on the Internet) is that you instantly become a potential target for ne’er-do-wells the world over. You can’t see your enemy and…that’s unsettling. However, the world is online and most of your secrets will be too if they’re not already, so you can’t un-ring that bell. There are pretty sophisticated security protocols that make systems quite secure. Another thing we do is coach users to be careful with what they share. With Kidworth we’re dealing with families with children, so we have to be pretty serious about security and privacy.”

DeFelice continues. “Another big issue is competition. Now everybody can see your product so when you’re teaching your customer about your product you’re teaching your competitor too. It means that you need to continually innovate or you get run over.”

Keeping an eye out on the competition is very much part of the rapidly changing world of doing business on the Internet. “Blackboard is increasingly entering new businesses and markets, and each of those brings with it its own set of competition,” explains Small. “The industry is constantly changing. For example, every college now has a mobile strategy where many universities weren’t even thinking that way just three years ago. That’s an area where we were able to make a big investment early on to get ahead of the market. The ability to keep our ear to the ground and make investments ahead of time is very important…In the software world, you can go from a leading position to a lagging position if you can’t spot and stay ahead of the trends.”

“TransConnect’s competitors are much larger translation agencies who may be able to provide translation services faster,” says Reiner. “But we believe that quality is too often lost in the rush to meet an urgent deadline. We never compromise quality for speed. We have turned down work requests when we believed that the deadline did not meet our quality standard. We also have been hired by clients to cleanup, do damage control or simply redo translation work that had been dashed off by larger translation agencies.

We are not only fluent in two languages, we also know two different legal systems and their intricacies, as we are both trained lawyers in France and in the U.S. Larger agencies cannot offer that specialization.”

Because Clearspire’s model is so unique, Cohen does not see major competitors as a short-term concern. “No other law firm has either our structure or the proprietary IT platform that enables us to implement it,” he says. “Others will claim that they are ‘just like Clearspire’ but they are not. That is not to say, of course, that followers will not pop-up, but the barriers to entry are fairly steep.” Is Clearspire more revolutionary than evolutionary? “I think it’s a little bit of both,” adds Cohen, who was on campus on October 6 to participate in a panel discussion entitled, “From Billable Hour to Bankable Career: What the Next Generation of Lawyers Needs to Know That Law Schools Aren’t Yet Teaching.” “I would call it disruptive in the sense that it is radically different from the way ‘big law’ is delivered. We kept what we think is good about big law firms – which is that they hire really smart people and do very sophisticated work very well. We did away with the things that create an innate conflict between their financial interests and the clients they serve, including the billable hour, the profit-per-partner, and the huge excesses of their opulent offices.”

“In many ways, the vacation rental market is still the wild west of the online travel industry,” says Gall. “With such a fragmented market of literally hundreds of thousands of small, unique vendors, vacation rentals offer the perfect challenge for an Internet business – an opportunity to bring together unique supply across the globe and present a more appealing traveler experience. That’s what we’re doing and it’s a real challenge.”

According to DeFelice, Kidworth also is blazing a relatively new trail. “The youth market is the most underserved segment of the financial services world, so there are really no established players a parent can go to to help kids start using their income more effectively,” he explains. “Therefore, the major competitive challenges stem from reaching the population, rather than from other companies. The kinds of things that most companies in the financial services space worry about – that the world is moving increasingly online…and that the economy is under pressure – are the very foundations of Kidworth’s DNA. So the farther the world heads in its current direction, the better it is for us.”

Small, Gall, Reiner, Cohen and DeFelice all look to the future with a strong sense of optimism that their businesses will thrive for years to come. “There are lots of exciting things on the horizon,” explains Small. “Blackboard just acquired, a very big move in K-12 for us. We also very recently announced a number a partnerships with many of the leading textbook publishers in the United States…all of which have invested in digital platforms that either replace or supplement their texts. These publishers comprise about 95 percent of the higher education textbook industry in America.”

“With an established global inventory of rentals, we’re now working hard to remove the pain of finding and renting the best vacation home,” says Gall. “In the past year, we’ve added map-based search results and filtering to find private homes based on popular amenities, such as hot tubs, private pools or ensuite bathrooms.” Gall also notes that before the year is out, FlipKey will be releasing a new feature “to truly push the industry forward and make it easier to rent your perfect house” (though at the time of publication he wasn’t ready to share the exciting news). “The future for vacation rentals is bright,” he adds. “I think we are just in the beginning of the industry moving closer to a predictable mainstream lodging option. Folks will start to consider a vacation rental not just for family trips to an oceanfront house or cabin next to the ski lift, but for every trip.”

“Machine translation is being perfected and could become interesting for certain areas of translation,” notes Reiner. “But in the area of legal translation, machine translation software is still far from being able to understand the subtle nuances of human speech and the complexities that legal terminology, in any language, implies. As legal translators, we are not terribly concerned about this advance in technology.”

As of today, Clearspire has approximately 50 employees, including more than 20 lawyers. Cohen sees that changing in a big way. “I would say that we are going to have controlled yet quite accelerated growth,” he says. “In the next three to five years we will have several hundred lawyers and a presence in many, if not most, leading global markets, where big companies have a need for our services.”

DeFelice shares the optimistic and entrepreneurial spirit of his fellow UConn Law graduates. “For a long time we have considered earning, saving and spending totally separate activities,” he says. “Kidworth merges them into an integrated whole and provides a system for managing them according to a plan. We think it will lead to a richer life. Lastly, Kidworth is online and social, which is how the youth market lives. The days when a young person walks into a bank and gets a passbook are about over. So my view is we are developing the model for financial services for the future.”

Feature: E-Graduates
Faculty News - Professor Richard Pomp, Internet Tax
Around Campus
Commentary: Joseph C. Steffan '94
Giving Back: Cornelius "Con" O'Leary '82
Giving Back: Emily Bell '02
Class Notes
Remembering - Judith A. Lahey '68


  • Lubbie Harper, Jr. '75, justice, Connecticut Supreme Court
  • Christopher F. Droney '79, judge, United States Court of Appeals for the Second Circuit

graduate report fall 2011 cover - computer screen

Click the cover to read the full issue.