The magic of starting your own firm // The Insider

Illustration of lawyer daydreaming at their desk
We spoke to three lawyers who left an established firm to start new practices — and are happier than ever

By Conan Tobias

On Tuesday May 25th, 2021

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From the moment he went to law school, Brandon Siegal had been laser-focused on Bay Street. In 2011, opportunity finally knocked. After spending the first five years of his career at the Department of Justice, he received an offer to join McCarthy Tétrault LLP as an associate. “I had the chance to jump up to the big leagues,” he recalls. “That was what I thought I wanted.”

Naturally, Siegal took the job. In short order, he built a practice in tax litigation. He represented sophisticated clients and worked alongside some of the finest legal minds in the city. He was living out his dream.

But within a few years, he started to run up against the bureaucracy that comes with working in a large shop. “Most decisions are made by committees,” he says, “in which I could not always participate.” He lacked the authority to determine which cases to pursue. His files, meanwhile, had gotten so large that he lost some of his passion for litigation.

So, in 2015, he left the stability of McCarthys and opened his own independent firm. “Now, I am responsible for all decisions,” he says. “It’s incredibly exciting and satisfying to always be the decision-maker.”

Quite often, lawyers find themselves hemmed in by the restraints of their organization, unable to take their career to the heights they want to reach. The solution, in many of these cases, is to leave and start something better. This course of action comes with risks, of course, but it’s not an impossible task.

Indeed, Siegal’s career path illustrates this precise point. As the founder of Siegal Tax Law, he handles some of the most high-profile tax disputes in the country. Over the past six years, he’s represented Pepsi Canada, Corus Entertainment and LawPro, proving that it’s possible to build an elite client roster without the backing of a blue-chip legal brand. He also drives the direction of his practice. “Today,” he says, “I’m in a situation where I can be flexible in doing what I want to do.”

How did Siegal arrive at such an enviable place? To start, he had to master his craft. And he’s the first to admit that he didn’t accomplish that by himself. He cut his teeth at the Department of Justice and McCarthys, workplaces that delivered rigorous training. Developing a legal skill set took time and hard work.

The actual logistics of starting a firm, meanwhile, were not as onerous as he had expected. In decades past, new firms had to amass an extensive paper library and take out an expensive lease on office space. These days, there are simpler options. Siegal subscribed to a handful of legal-research services, which was far cheaper and more manageable than creating his own library. He also moved into a co-working space at First Canadian Place that included access to a reception, a mailroom and a boardroom. All at a reasonable price.

Siegal assumed that he would eventually upgrade to a permanent office. But he quickly abandoned that plan. As it turned out, his clients didn’t care all that much about his office. And Siegal discovered that he was just as productive at home. “I tell people that I do 95 percent of my work from my home,” he says. “That’s the same revelation that a lot of lawyers are having now during COVID.”

He netted his first batch of clients through referrals, sent his way by connections he made in the first decade of his career. As he got to work, he relished the freedom to handle the files his way. Because he doesn’t have an army of associates to keep busy, for instance, he performs the document review on each case himself. Most large firms assign this task to the junior members on the team, but Siegal’s clients are comforted by the fact that a senior lawyer is performing this vital work with expert hands. Best of all, his low overhead has driven down his hourly rate. “I’m able to charge a rate closer to that of a senior associate,” he says. “The actual costs to the client are not increased that much if I do all of the work.”

Illustration of lawyer jumping from one cloud to the nextBy 2015, Kavita Ramamoorthy had built a stellar career in litigation. At the time, she was a partner at an intellectual-property boutique, where she handled high- stakes disputes on behalf of major pharmaceutical companies. Much like Siegal, however, she felt disconnected from the decision-making process at the firm. “Even when you’re a partner, you don’t necessarily get a say in how the business is run,” she says. “That’s true in big and small firms alike.” Eventually, she reached a blunt conclusion. “If I’m not completely happy, I should be trying to figure out why — and changing that situation.”

In 2017, a solution appeared. Around that time, one of her law-school friends, Neil Fineberg, struck out on his own, launching a small firm in her exact practice area. He asked Ramamoorthy to join. Though she was cautious, she decided to make the move. “Neil was very persuasive,” she says. He had a concrete business plan and a path to developing a client list.

Ramamoorthy was also confident that, after more than a decade in her field, she could generate her own book of business. That would not have been the case at an earlier stage in her career. In her telling, the world of pharmaceutical litigation is hostile to newcomers. “You’re talking about products that could be worth millions of dollars,” she says. “You want to make sure you’re giving your clients confidence that they can entrust you with this type of high-stakes litigation.”

Fineberg Ramamoorthy LLP has been a resounding success. What began as two partners and one associate has blossomed into a team of eight. Now at the helm of her own firm, Ramamoorthy has total control over her work, including the files she accepts and the legal strategies she deploys. Her impressive client list includes several top generic drug companies, such as Sandoz, Pharmascience and Accord Healthcare.

“With our own shop, we decide how to run the business,” says Ramamoorthy. “I hope part of what clients see in us, and hopefully value, is the priority we put into relationships — making sure that we’re giving them not just our best knowledge, experience and expertise, but also making sure they know that if they phone me,
I will pick up. That’s important, especially when you’re trying to build.”

In 2018, Daniel Nauth was feeling unhappy. Fourteen years removed from law school, he was working at the Toronto office of Dorsey & Whitney, a major American corporate law firm. Not only did he lack autonomy over his work, but also his life. “I was just kind of over Big Law,” he says. “It wasn’t fulfilling. It didn’t jibe with who I was and what I wanted.”

Nauth’s career up to that point had been a whirlwind. After graduating from law school at Queen’s University, he had short stints at Goodman and Carr LLP (which he left one year before the firm’s implosion in 2007) and Stikeman Elliott LLP. After he got a call from a recruiter, he moved to New York to join Milbank, Tweed, Hadley & McCloy, a large international firm. He wrote the New York bar exam, earned his licence and hoped to find fulfillment in his work. Then the collapse of Lehman Brothers in 2008 triggered a global economic meltdown and cost Nauth his job. Unemployed, he returned to Canada.

That’s when he saw his ability to practise in New York as a competitive advantage. He could handle the American side of cross-border transactions, working from an office in Toronto. He eventually landed at Dorsey & Whitney, where he did this exact work.

After his six years at the firm, though, he was feeling dissatisfied. He was also optimistic that, if he went out on his own, he had the reputation to land clients. “Not many firms do what I do,” he says. “There was an opportunity for me to carve out business. I was already doing it at Dorsey, so why not do it for myself?”

That is precisely what he did. He rented a small office and founded Nauth LPC. Since leaving Big Law, there are certain deals he doesn’t have the capacity to handle — such as U.S. public M&A transactions — but there’s more than enough work to keep him busy.

And he’s more satisfied than ever with his career. “I like control over my life,” he says. “It’s one thing to go into a weekend knowing I have lots of work to do. I can manage my life around that. It’s another thing to have no visibility over what the work pipeline looks like over the weekend.” These days, he might get the odd emergency call, but at least it’s from a client that he has a relationship with. “I don’t have full control,” says Nauth, “but it’s more palatable because it’s something I’ve built.”

Now five years into his solo practice, Brandon Siegal couldn’t be happier with his decision to leave large-firm life. “My biggest fear of leaving a big firm was losing my reputation — the sense that, in being on my own, I would be viewed as taking a ‘step down’ from being at an established firm,” he says. “The most rewarding, and surprising, part of starting Siegal Tax Law is the realization that I have cemented my reputation. It’s an incredible feeling when you see your logo on the letterhead. You’re able to say, ‘Wow. I built this.’”


This story is from our Summer 2021 Issue.


Illustration by Sam Island.