Copywriter, technical writer, translator (FR>EN, ES>EN, IT>EN), journalist

Going all-in on legal technology startups

Across the country, a subset of the legal profession also develops software. They develop because they’re driven to build the software they want, tools they consider better than what’s currently available.

In this two-part series, we’ll hear from three Canadian lawyers who have launched, or intend to launch, new legal software offerings between December 2016 and 2017. Each startup’s story started with an itch that the pace of technology innovation in the legal field doesn’t relieve.


“Before I went to law school, I was a graduate student at Harvard,” said Aaron Wenner. “That meant writing a lot of research papers and footnotes and bibliographies. Luckily for me, I personally never had to write a footnote or a bibliography throughout my time at Harvard because I had software that would do it for me.”

A reality check awaited. “When I got to law school at McGill, they taught us how to manually write a footnote.” Wenner, the CEO of CiteRight, a document drafting assistant, goes on to note that in law practice, unlike in academia, you copy as much of your firm’s work as you can, but the need for citations doesn’t disappear. “If you want to save money for your client, you re-use work wherever possible that you and your colleagues have already done.”


“Maritime Law Book is a startup decades in the making,” said Colin Lachance, a veteran of three legal technology startups.

In 2016, the venerable legal research tool (now Compass) stopped print publication soon after Lachance, now its CEO, and his team took over. They then began to transform its online offering. Lachance notes that human editors employed by Maritime Law Book classified cases. The Compass team plans to teach artificial intelligence systems to perform that classification work.

Compass has since taken investments from legal information publishing companies vLex and Justia. It has already launched vLex Open Canada, a free service, and plans to launch paid services vLex Canada and vLex Global.


Barry McMullan’s third application shipped earlier in 2017. An Edmonton-based solo family lawyer at McMullan Law Office, he has been developing the child and spousal support application iGuideline for five years. He now markets it using his company Orsa Software Inc.

Like Compass, iGuideline faces competition. “Other products in Canada do child and spousal support calculations,” McMullan said. “I’ve never been happy with those offerings and thought I could build a better mousetrap.”

Software talent

Getting an application off the ground takes an idea and workable designs. These come from the lawyers. Then software development talent turns ideas and designs into workable prototypes and finished products.

That talent can come from several places. Lachance, for instance, brought in a team he worked with on another venture. McMullan, on the other hand, is a self-taught developer who has already developed two other applications. “I built trust accounting software in 2000 called TrustMate,” he recalled. “It took me about 500 hours. I remember. I logged the hours.”

“I ran this software in my office for more than 10 years before the law society said it didn’t comply with their latest requirements.”

“Before iGuideline, I built another app called iTableAmount, which shipped in 2014,” McMullan continued. “That was a proof-of-concept app I built for both the Mac and iOS to prove that I could create documents that are cross-platform compatible and that could be saved in iCloud.”

Wenner’s coding involvement lies in between Lachance’s and McMullan’s. He noted he’s been coding since he was 11, but unlike McMullan, he doesn’t build the product. “I can recognize the nature of the problem and a possible solution,” he said. “I can code an initial version that I can hand off to developers.”

The importance of networking

People other than developers are helping these lawyers in their tech startup journeys. They bring aptitudes that the ideating lawyer may lack, like management, marketing and other requisite business expertise.

Lachance encourages tech entrepreneurs looking for the right mix of skills to seek tech startup communities in their cities. “There’s a desire for people to merge capabilities and insights,” he said. “We’re residents of the Legal Innovation Zone at Ryerson,” Wenner said. “I’m also on the executive of Toronto Legal Hackers.”

To reassure lawyers who hesitate at the thought of joining a group of “hackers,” legal or not, Wenner distinguishes between hacking — “finding an elegant solution to a technological problem” — and criminal hacking, or cracking.


Lawyers who moonlight may need to write off “work/life balance” as a pipe dream. Wenner, for instance, isn’t currently practising, choosing instead to focus on CiteRight. Lachance only did one file in 2016, “and they sought me out. I said ‘That’s interesting! I’ll fit it in.’ While I remain a practising lawyer, it doesn’t fund my life in any meaningful way.”

McMullan builds his software tools using sweat equity while maintaining his practice, but he candidly acknowledged the difficulty of late nights of coding followed by morning court appearances.

He wouldn’t give it up. “In law, we don’t really build anything,” he mused. “I found personally there was something missing, so I wanted to build something, something I needed.”

Lachance is blunt about his view of the technology entrepreneur’s journey. “There are only two options,” he said. “Keep it as a hobby, or go all in. There’s no in-between.”

Nervous about their prospects, lawyers might want to seek a middle ground. CiteRight’s Wenner understands. “At any early-stage company, you worry about somebody you haven’t heard of scooping you, developing a similar product.”

Lachance acknowledged the risks involved, and insisted lawyers embrace them, even if they do so slowly. “There’s lots of room for hobbyist lawyers who participate in legal hacker communities. I encourage lawyers to indulge their interest in working with other professionals to develop solutions. It’s exciting, it’s engaging and you don’t have to give up your job to do it,” he said.

“If you want to turn this into a business, you must go all in.”

In part two of this series, the three entrepreneurs discuss the markets they face, their marketing insights and their business development tactics.

This article originally appeared on The Lawyer’s Daily website, published by LexisNexis Canada Inc.

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