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

Improving legal service delivery by going online

Lawyers as technology entrepreneurs

Doug Simpson holds a degree in computer science. Engineer Monica Goyal worked for years in the technology industry. Both Michael Bluestein and Michael Carabash profess passion for both business and technology.

These technophile lawyers believe they can improve the delivery of legal services. That’s why they moonlight as founders of software start-ups that serve the legal market.

While what they’re doing isn’t new, they’re banking that a combination of experience practising law plus a business plan will help them succeed as technology entrepreneurs.

Prior experience as a “lawyer on the clock” convinced Bluestein that lawyers “know what the market wants, how the technology is used, how it integrates with current systems.” In his opinion, that gives them an edge over software developers without a legal background.

Unsurprisingly, the market for Time Is Money Billing Systems (, which Bluestein runs during his time away from his job as in-house counsel, includes any professional who tracks time. “We started with lawyers because that’s what I’m familiar with,” Bluestein says.

The other three lawyer/tech entrepreneurs also serve markets they know well: members of the public seeking accessible legal services. Access is “a big failing in the structure of our justice system,” Goyal says, calling the opportunity “a huge market of under-served clients.”

Even market niches can be significant. For instance, Carabash helps dentists buy and sell dental practices. “serves our law firm’s clients (both prospective and actual), is niche in its focus (only for Ontario dentists), and gives our law firm a competitive advantage over other firms that target dentists,” he explains.

“Few lawyers develop specialized knowledge in the dental field,” he says of his firm and website.

The expert system behind the small claims process management service started to form in Goyal’s mind when she noticed that few services were marketed to self-represented small claims court litigants.

Outside events and trends can influence a business plan as well. Goyal’s site came online “around the time when Ontario increased the small claims amount from $10,000 to $25,000,” she recalls. For his part, Bluestein chose to develop for Apple devices owing to his findings that iPhones and iPads are immensely popular among American lawyers. (Android development is next, he says.)

Developing automated time capture for mobile Apple devices proved a high barrier to entry. “It took a lot of development effort,” Bluestein says. “Many competitors saw roadblocks and didn’t bother to solution around it.”

Starting a technology firm while practising law is not for the faint of heart. Carabash’s start-up to-do list included everything from preparing business requirements to process flows to wireframes to hiring developers to testing the software “religiously.”

“There’s nothing worse than having a product that’s full of bugs,” Simpson concurs.

“Very little sleep and no free weekends or evenings,” says Bluestein of his current routine. Goyal is thankful for her family network, given her workweeks of 60 to 80 hours.

As a rule of thumb, “projects take three times as long and twice as much money as you think they will,” Simpson says. To keep timelines and budgets under control, he recommends entrepreneurs prevent scope creep.

For instance, when he started his forms site, he would rather do a good job on just wills and power of attorney, and put off family trusts and other parts of estate planning. “I’ve seen many projects fail because there is no finish line,” he says.

Businesses rarely work out according to business plans and entrepreneurs may need to adapt. For instance, Carabash initially set up a lawyer referral service on his other online business, This part of the site didn’t catch on very quickly.

“It took a few years for me to recognize the issues, and when I did, I changed the business,” he says. He now focuses the site on selling legal forms, which Carabash says poses higher barriers to entry.

Distribution might seem less difficult in the Internet age, but the right deals can improve sales. “Last year we relied on a lot of third-party deals companies like Groupon or WagJag,” Carabash says. “They sold a fair amount, but deal sites have merged or vanished, leaving us with a less robust distribution channel. But we’re seeing sales in line with last year, even without the deal sites.” Carabash assumes that word of mouth has kept sales from falling off.

“I’d like to see my software available in places like Staples, Walmart and Costco,” he adds.

To his surprise, Bluestein found cold calling works well “if you get the right person.” He works his network as well as trade shows to get the word out.

While Goyal primarily markets to the non-legal market, she partnered with the online practice management tool Clio to link the two systems. “(It) allows people who use both of our services to use data…across our two sites,” she says.

Carabash, Goyal and Simpson generate leads for their legal services from their technology ventures, but lead generation might not be the best motive for creating technologies like theirs. Goyal points to more cost-effective lead generation tools like Google Ads. “You’d be surprised at how many lawyers do not even have a website,” she says.

Expanding to the United States gives some entrepreneurs pause. Carabash cites higher levels of competition and a more litigious environment as reasons to delay entry to the American market. “I’d rather be a big fish in a small pond that I’m familiar with,” he adds, noting that he’d rather expand through Canada first.

Bluestein, on the other hand, figures he should have gone after the U.S. sooner. “U.S. firms move on attractive technology more quickly,” he says.

Goyal advises start-ups create a “minimum viable product” to test their markets. “Just get out there,” she urges. “You won’t know if an idea will interest people unless you put it out there.”

“The longer you wait, the more likely somebody else will come up with the same idea and run with it,” she warns.

This article originally published in Lawyers Weekly Magazine. To view a PDF of the printed version, click here.