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I traveled to Denver to talk to John Tredennick Jr. about his decision to break away from Holland & Hart, the largest firm in the Rocky Mountain region, and create CaseShare Systems, a now-tiny technology spin-off with big hopes. We eventually got around to talking about CaseShare and its plans to sell cool technology to corporate counsel and other firms. But it was not a simple or straightforward conversation. Randomly and spontaneously, Tredennick, 48, interjected tales of helicopter skiing in the Canadian Rockies; working out with a personal trainer at 6:30 a.m.; jumping in horse show competitions; and playing in a rock-and-roll band in his youth. He free-associated about the beauties of Adobe Acrobat as a law office automation tool, the limitations of Lotus Notes, the power of spreadsheets like Excel, and the complexities of writing programs for the Web but the simplicity of using them. Six-and-a-half hours after arriving, I left with my story and was ready for a nap. I felt like I had just emerged from inside a nuclear reactor. Tredennick was a trial lawyer for 20 years. But in conversation he has more in common with Robin Williams than Warren Christopher. “He’s exhausting,” says Edward Flitton III, Holland & Hart’s managing partner. “There isn’t anyone else exactly like John.” Tredennick brings the same rapid-fire idea generation to his clients, who come to him for ways to simplify, automate, and smooth the way that they practice law. He is paid to think outside the box and inside the Web. About the only thing constant about Tredennick is his line to clients when they complain about the amount of paper that lawyers create and the redundant steps that they take. “You know,” Tredennick says, “there might be a better way to do this.” Tredennick’s Holy Grail is a paperless office, where lawyers, especially litigators, can practice quickly and efficiently, and clients can save money and time. To do this, Tredennick thought — and the firm ultimately agreed — that he needed to be outside the firm and within an entrepreneurial setup to strut his stuff. CaseShare was spun out Oct. 1, 2000. Whether or not it ultimately turns out to be a good business decision, clients are benefiting. Take this example: For a major international insurer involved in a complex series of interrelated cases, CaseShare is eliminating the courier-delivered packages, the incessant trips to the fax machines, and the nearly constant trips to the file and copy rooms. All incoming mail — pleadings, correspondence, briefs, all of it — is scanned and put on a Web site. Each of the 20-30 defense lawyers will receive an e-mail, rather than an overnight delivery or a fax, when a new document has arrived. The client, which does not want to be identified, has put firms on notice that it will not be paying for routine copying, fax, and courier charges for this case, since all the material is just a mouse click away. “Nobody misses the paper,” says one lawyer, whose assistant was spending more than two hours a day handling incoming mail from this litigation. For Sears, Roebuck and Co., CaseShare has likewise eliminated many of the cumbersome steps to review advertising for compliance. Rather than manually route the thousands of advertisements from department to in-house counsel, to outside counsel, and back, Sears uploads each ad once to a secure Web site. (As the fifth-largest U.S. advertiser, Sears produces 20,000-25,000 ads a year.) Lawyers can then review the ad, pass their comments along, and store them, so that the work does not have to be duplicated when a similar ad comes along. The Web-based system is allowing the retailing giant to bring this work in-house. Holland & Hart wasn’t doing the review work, so it was not penalized for building the automation system. CaseShare has also created a secure Web site to track employment disputes at Albertsons Inc., the giant food chain. Employees of Albertsons have one place to go to learn the status of any dispute, whether it is with the National Labor Relations Board, the Equal Employment Opportunity Commission, or a union local. The site also generates automatic e-mail reminders about upcoming deadlines. For the last several years, law firms have toyed with creating stand-alone businesses related to — but not part of — the practice of law. Tredennick, who writes and speaks frequently about technology, may be the best-known executive of one of these operations, but there are several others. Cincinnati’s Dinsmore & Shohl has created a wholly owned unit, DinsNet Technologies, with similar aspirations — but on a smaller scale. And Winston-Salem, North Carolina’s Womble Carlyle Sandridge & Rice just spun out FirmLogic, which will try to offer even more comprehensive services than CaseShare. It is basically a full-scale legal technology consulting and services firm. Womble Carlyle has long sought a competitive edge through the use of technology. It’s too early to tell whether other law firms in particular will come to rely on spin-offs of competing firms for technology services. Hassel Parker, the chief executive of FirmLogic and the former executive director of Womble, says that within North Carolina, it’s a tough sell. “I’m still Womble to them,” he says. The larger issue, however, is whether lawyers should stick to brief writing, risk assessment, and rule-making, or venture into the workflow analyses that now fill Tredennick’s day. For Tredennick the tension between practicing law and making the practice of law more efficient has been building for several years. Since the early to mid-1990s, Tredennick has been working on ways to bring about better lawyering through computers. His work progressed from spreadsheets to automated docketing systems, an idea that grew out of a court deadline that Tredennick missed. He vowed never to let it happen again. “I started thinking of computers as not just a typewriter or an adding machine, but as a strategic weapon,” Tredennick recalls. One of Tredennick’s first breakthroughs was the creation of a litigation support system based on the Adobe Acrobat file format. By tweaking Acrobat, Tredennick’s technology wizards were able to pull together what, in most litigation support systems, are three separate files. The first of those files consists of the images of documents. The second is the text of those documents, generated through optical character recognition. The third is the index of the key words and full text. In simple terms, the technology staff at Holland & Hart was able to sandwich those three files into one Acrobat file. This makes it much easier for lawyers to search and retrieve documents. For example, a typical system creates separate image files for each page. Acrobat permits multiple-page files. Rather than opening and closing 20 files to read a 20-page memo, a lawyer is able to browse through a single file. A second breakthrough was Tredennick’s recognition that the Internet was a giant copy and fax machine. Suddenly, lawyers had a way to share these documents and services easily with clients. “You have the ability to do a shitload of stuff that you couldn’t do before,” Tredennick says. By this time, in the mid- to late 1990s, Tredennick was the firm’s chief information officer while maintaining his law practice. The firm had started to charge clients modest sums to build these extranets to keep track of cases. But Tredennick wasn’t thinking that he was creating a business. “They often talk about how you should bond with clients through golf or hockey tickets,” Tredennick says. This was his way of doing that. In 1999, Tredennick reached a crossroads. “I want to be like Fred Bartlit, and I’m not,” he remembers thinking, a reference to the famed name partner of Chicago’s Bartlit Beck Herman Palenchar & Scott, who is also facile with technology. “The reason I wasn’t, besides not being as smart, is that you have to give it 1,000 percent.” After 20 years as a trial lawyer, Tredennick ultimately concluded that “I don’t have the desire to rummage through boxes and find out who did what to whom.” He considered whether he should raise money from venture capitalists and position the company as a dot-com. But although he was tired of practicing law, he was accustomed to the collegiality, status, and comfort of firm life. “I didn’t want to throw $100,000 parties and do the classic dot-com thing,” Tredennick says. He approached Holland & Hart about spinning off the firm’s Web and litigation support activities. After much internal debate about exposures, conflicts, and all the other things that lawyers get paid to worry about, the partnership approved the spin-off in May. Ninety percent of the partners favored the decision. According to Flitton, the partnership looks at CaseShare as a way to improve client service and a way for Tredennick to expand his business without having to clear every client through Holland & Hart’s conflict system. Holland & Hart gave CaseShare $500,000 in equipment and guaranteed a $1.5 million line of credit. Tredennick and two employees currently own 23 percent of the new company. The law firm owns the rest; the firm’s percentage may shrink to 67 percent over time, to make room for other CaseShare employees, investors, or partners. CaseShare started with 13 employees. Today it has more than 40, as new work keeps pouring in. “This boat is not big enough,” says Bruce Blank, CaseShare’s chief operating officer, a technologist who had been at Holland & Hart. Tredennick continues to receive a draw from Holland & Hart, where he still serves as chief information officer and is an inactive partner. Combined with his CaseShare salary, Tredennick hasn’t suffered a drop in income. “It’s been a risk-free strategy for me,” he says. But not worry-free. Tredennick says that one of his main jobs is to achieve staff contentment, so that they don’t bolt. At the law firm, Tredennick could do everything that needed to be done to prepare a case. His associates could get hit by a bus, his assistant could call in sick, and Tredennick could still practice. Not so today. He can’t do the programming required to bring out the CaseShare products. “I’m at their mercy,” he says of his staff. The company doesn’t have a typical marketing budget other than Tredennick’s travel expenses, flying from venue to venture, extolling the virtues of the paperless office. Most of his new clients are corporations, rather than firms. CaseShare made money its first month of operation, thanks to the work Tredennick brought over from Holland & Hart. It lost modest amounts in November and December, due to equipment purchases. Tredennick says that he expects to bring in somewhat less than $10 million in revenue the first year of operation. Most of CaseShare’s projects came in via the Holland & Hart connection. But both Flitton and Tredennick expect that to change over time. Neither of them, however, expects Tredennick will ever take on a client whose opposing counsel on the matter is Holland & Hart. Over the next few months, the company’s biggest technical challenge is to move its extranet services over to a system based on Microsoft Corporation’s Exchange Server 2000. The benefit is that lawyers, familiar with the Outlook front-end on their desktops, will be able to pick up the system quickly. The downside is that nobody has done with Exchange Server 2000 what CaseShare is trying to do. The product is so new that many of its capabilities aren’t even documented, yet alone commercially exploited. The experiment with Exchange is like Holland & Hart’s experiment with CaseShare itself. Says Tredennick: “It’s a gamble, but a good one.” Sort of like helicopter skiing.

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