From 25+ Years on Bay Street to Betting on Herself at Dipchand LLP: May Cheng on Leaving Big Law for a Boutique IP Powerhouse, Building a Specialty Practice in Anti-Counterfeiting, and Navigating Bill 96's French Language Requirements
May Cheng is a partner at Dipchand LLP, a Toronto-based IP boutique that Legal 500 describes as "a small but mighty IP boutique that punches well above its weight." But May's path to this woman-led, seven-partner firm came after spending over 25 years at top-tier Bay Street firms including Osler, Hoskin & Harcourt, Fasken Martineau DuMoulin (where she served as Chair and Partner of the Toronto Intellectual Property Group from 1999-2016), Smart & Biggar, and Scott & Aylen (now BLG Gowling WLG).
May is a Lexpert/ALM 500-ranked intellectual property lawyer recognized as "very strategic" and "experienced and effective" in brand protection and enforcement. She's been named an IP Star for the past decade by Managing Intellectual Property Magazine and received a Gold Band ranking in Enforcement and Litigation and Silver Band in Anti-Counterfeiting. Chambers describes her as bringing "a wealth of knowledge and experience across a range of industries" with "exceptional skill set" that makes her "an irreplaceable part of our IP strategy."
In 2023, May received the Lifetime Achievement Award from the Federation for Asian Canadian Lawyers—the organization's highest honour—for her career as a mentor and role model for Asian Canadian lawyers, including her advocacy for Head Tax Redress and other Asian community groups. She was nominated for Canadian Lawyer's Top 25 Most Influential Lawyers 2024, recognizing her exceptional contributions to equity, diversity, and inclusion in the legal profession. May has also received recognition from the Ontario Bar Association for her mentoring of women in law and volunteer work in the field of women's equality.
With nearly three decades of experience, May has established a strong reputation in brand protection and enforcement with a specialty practice in anti-counterfeiting, working across all major industries with particular focus on retail, travel, fashion, and food. Her litigation experience spans patent, trademark, and copyright infringement cases, expungement and injunction cases in federal and provincial courts. She's described as a "fearless advocate" whose goal is to arrive at the best business solution for clients, which often isn't achieved through protracted litigation.
May writes extensively for The Lawyer's Daily about IP issues (including McDonald's aggressive brand protection strategy) and has been featured on the Lawyered podcast discussing Bill 96 and Quebec's new French language requirements for advertising, bad faith trademark registrations, and copyright law regarding AI derivative artworks. She presents regularly at Law Society of Ontario programs on trademark law updates and is recognized as both a rainmaker and an inspiration to countless Asian-Canadian and women lawyers.
In this Q&A, May shares why she left the resources and platform of elite Bay Street firms to join a boutique practice, her framework for deciding when aggressive brand enforcement makes business sense versus when it escalates costs unnecessarily, and practical advice for Canadian businesses navigating Bill 96's French language requirements and bad faith trademark registrations.
From 25+ Years at Top-Tier Bay Street Firms to Joining Dipchand LLP - Trading Big Law for a Boutique IP Powerhouse
You spent over 25 years at top-tier full-service firms on Bay Street (including Osler, Hoskin & Harcourt, Fasken Martineau DuMoulin, and Scott & Aylen (now BLG) before joining Dipchand LLP, a boutique Toronto law firm focused exclusively on intellectual property, corporate law, franchise law, and litigation. You're recognized as a Lexpert/ALM 500-ranked intellectual property lawyer known for being "very strategic" and "experienced and effective" in brand protection and enforcement. For female attorneys considering leaving prestigious Big Law partnerships to join smaller, specialized firms, what prompted your decision to leave the resources and platform of elite Bay Street firms for a six-lawyer boutique? How did you evaluate whether Dipchand LLP's culture, values, and focus aligned with your practice goals, and what advice would you give women about making the leap from established firms to boutique practices without sacrificing professional reputation or client relationships?
Lawyers are a risk-adverse group generally, so I can appreciate how the idea of leaving Big Law can seem daunting. Women lawyers in particular are also even less likely to move firms, because they are less motivated by money and they are extremely loyal both as employees and as partners. I've spoken to recruiters about this paradox, where the women get paid less and yet are not prepared to seek out a promotion or a better platform for their practice, because they feel they do not have the perfect experience level for a promotion or because they do not have the confidence that they can bring their clients with them. Male lawyers will actively seek out options for higher compensation, even just to come back to their current firms to leverage another firm's offer into a compensation level increase. What I noticed as I was rising the ranks in Big Law was that women partners were leaving in higher numbers and did not rise as quickly as the men in the partnership, but many of the women would ultimately leave Big Law for in-house roles. I love the work that I do, and I really had no interest in moving to an in-house role, because I enjoy private practice and the depth and breadth of the files I got to work on. Ultimately, there is a higher price tag for your overhead in Big Law, and while you may attract larger files you also give over a larger proportion of the revenue generated to pay for all the trappings, including the fancy office space, big budget marketing machinery, expensive client events and partner conferences. In one of my moves within Big Law, I realized that I had the relationships and the profile to bring a lot of work with me, because I had developed a loyal client base that was portable. Then the pandemic came along and showed us all that the showy trappings of the big firm were not really valued by clients, that what really mattered to clients was good advice and they no longer wanted to subsidize the fancy offices with the outsized hourly rates. It's a misconception that you don't get the state-of-the art resources outside of Big Law, because small firms actually have the ability to adopt new technology faster and more cost effectively, and with the big firm come tons of conflicts that prevent you from taking a lot of great files. I had a bit of an epiphany during the pandemic that technology had levelled the playing field for small firms in being able to manage deadlines and litigation support functions without the huge teams. I also recognized that I was not truly enjoying the success that I had achieved, as there was constant pressure to take on so many roles internally and externally, particularly as a visible minority woman in a white male dominated environment. I felt pressure to constantly be putting myself out there, while not being recognized for all the extra effort at the end of the day. Ultimately, at a certain age and stage, I also started to ask myself: what am I building and for whom? Did I really just want to build up an enviable practice to hand it off to these managers who viewed it as nothing more than a drop in the bucket? I've always strived for impact in my volunteer work, particularly work that would advance women and minorities, why not do this with my legal practice?
My choice to join Dipchand LLP had a lot to do with the soul searching I was doing mid-pandemic and the fact that I got to know Elizabeth Dipchand on a more personal level during that time. She is the one who asked me "Why don't you bet on yourself?" That question really resonated with me and ultimately fuelled my decision to leave Big Law. Being a partner in a much smaller firm allows for engaging in decisions as an actual partner and not just a glorified employee. Decisions in Big Law are made by an elite Partnership Board or Compensation Committee, where the equity partners get a vote, but not always a seat at the table. I will not only have a say in my succession planning, but the opportunity to train up my successor(s) and build something that reflects my values. I get a direct say in the types of cases we take, and can represent smaller clients on files that I would be forced to turn away in Big Law. I think the message for women looking to make a leap is that you can control your own destiny, because your reputation and skills follow you, so no one can take those from you. We are in a service industry that is all about trusted advisor relationships. Women are generally better than men at building relationships, so remember that if you have done your work well you can trust that those clients will follow you. I was pleasantly surprised by the number of clients that I did not expect would follow me to a smaller shop that sought me out to continue with the relationship following my move. If anything, the move to a boutique environment has allowed me to deepen those relationships and focus on clients and causes that matter to me most. As you become more senior, you need to constantly re-evaluate what is working for you and what no longer serves you, to truly strive to live your best life. Success is not defined by a corner office. My life has always prioritized my relationships with my spouse, kids, family and friends, as well as my community work. I think people who prioritize work and money not only miss out, they become miserable chasing the illusion of success. True success for me is grounded in balance and a rich, fulfilling personal life.
Building a Specialty Practice in Anti-Counterfeiting and Brand Protection - Advising Retail, Travel, Fashion, and Food Companies
You've established a strong reputation in brand protection and enforcement with a specialty practice in anti-counterfeiting, working across all major industries but with particular focus on retail, travel, fashion, and food. Your litigation experience spans patent, trademark, and copyright infringement cases, expungement and injunction cases in federal and provincial courts. You're described as a "fearless advocate" whose goal is to arrive at the best business solution for clients, which often isn't achieved through protracted litigation. For female founders building brands in retail, fashion, food, or travel industries, what are the most critical IP protection mistakes you see startups make early on? How should founders approach trademark registration, anti-counterfeiting strategies, and brand enforcement when they're bootstrapping or in early growth stages, and what's your framework for deciding when aggressive enforcement makes business sense versus when it escalates costs unnecessarily?
My best advice is to start by doing the research on not only your product but your marketing plan. You need to find a product name or company name that will create a value proposition for customers and resonate with the market. My job is not only to file trademarks, but to help out with the choice of the trademark/brand, to conduct the due diligence on the choice of name/mark/logo before the company makes a misstep by not identifying other market players who may already have a stake in a confusingly similar name/mark. Nowadays the federal and provincial governments in Canada are prioritizing trademark and patent protection for Canadian start-ups, so there are funding sources available to new market entrants to be able to go get their trademarks and patents early. All of the good law firms in the intellectual property field know how to tap into these funding sources and can help a new company avoid spending all their early cash on trademark and patent protection by tapping into these government resources. The biggest mistakes I have seen start-ups make in the past are: (1) not clearing a trademark before adopting it and spending a lot on marketing, only to be met with a cease and desist letter; or (2) overspending on trademarking every possible iteration of their logo, in multiple countries, only to run out of money before they can get the product to market by spending too much on legals. Start-ups need to prioritize what is absolutely necessary versus nice to have. Searches and clearance are necessary, trademarks for every single iteration of the logo are just nice to have but should only be pursued if there's cash to burn.
Anti-counterfeiting is mainly a problem for bigger and popular brands, or overnight successes. Sometimes the spending can be wasted on "whack a mole", because imitators crop up from all over, even if you shut a few down. However, going after a few examples more publicly, by filing a claim for instance, against some of the more egregious copycats can go a long way towards deterring others who want to use the same playbook. Enforcement needs to be strategic and advice from senior practitioners is critical in helping to decide who to go after or what methods will have the best return on investment. Sometimes a demand letter is enough to scare off a copycat, but if there's a lot of targets that you're chasing, you may need to tolerate some competition that doesn't really hurt your customer base and allows you to not spend all the profit chasing infringers. Even really successful and famous brands have tight budgets for enforcement and are always looking for ways to avoid anti-counterfeiting spend, but some do so little to protect their brands that dilution leads to diminished value.
Navigating Bill 96's French Language Requirements and Bad Faith Trademark Registrations - Practical IP Strategy for Canadian Businesses
You've been featured on the Lawyered podcast discussing Bill 96 and Quebec's new French language requirements for advertising, bad faith trademark registrations, and copyright law regarding AI derivative artworks. As someone who writes extensively for The Lawyer's Daily about IP issues (including McDonald's aggressive brand protection strategy), you balance strategic legal advice with practical business considerations. For female entrepreneurs expanding into Canadian markets or dealing with cross-border IP issues, what do founders need to know about Bill 96's French language requirements and how does this impact companies' advertising obligations? How should startups approach trademark registration in Canada to avoid bad faith claims, and what are the early warning signs that a competitor's trademark registration might be vulnerable to expungement?
The key for successful market expansion into Canada is to start with the legal advice you need to avoid regulatory and other pitfalls, which can put the whole investment into a new market at risk of failure. On the French language requirements side, one strategy is to avoid selling into the Quebec market initially to not have to make the investment in translation and other regulatory compliance issues at the start. There have been new decisions about trademark protection and signage requirements that really need to be researched and planned out. For example, SWATCH recently managed to avoid having to translate their signage on the basis that SWATCH is a coined word and not an English word. So, choice of trademark and solid advice on signage requirements are really important for a new market entry in Quebec or face costly fines and potential litigation.
Bad faith registration is something that is being used more aggressively in Canada lately as a basis for opposing trademarks or for preventing local companies from trading on the goodwill of famous or successful foreign brands. There are critical considerations, but the main objective has to be clearance searches and doing your homework to ensure that you are not trying to launch with a name/mark that is too similar or likely to be confused with an existing competitor in the market. As the world grows smaller with the reach of online shopping via the Internet, more brands are colliding across platforms or in new markets for foreign brands where their diaspora are migrating to adoptive countries. While it may be tempting to try to mimic the success of a foreign brand from a faraway place, the new remedy for bad faith registration can play a role in preventing the adoption of nostalgic brands in new markets if it's not by the original source from a foreign country.
Expungement is also a useful tool for clearing a trademark that is no longer in use by a competitor or opposer. The Canadian Intellectual Property Office (CIPO) has also launched a new randomized expungement program to try to clear "dead wood" from the Register where a brand owner is no longer using a mark. Previously, a party needed to commence an expungement proceeding, but now CIPO can take the initiative. It's also a cautionary tale for a client who wants to assert a weakly used mark against a third party, only to find itself on the defensive when a cancellation is initiated by the party they have aggressively sent a demand letter to. Expungement can really turn the tables on a market player who is too bullish on its rights. It's always risky to assert rights against a third party without doing the proper research on when they started to adopt and use their mark. Fortunately, there are many tools at the disposal of trademark lawyers to investigate the prior use made by a competitor. One cautionary tale on a file I worked on involved Atomic Energy of Canada, which was aggressive in asserting its "A" Design against Areva when they entered the Canadian nuclear market. Acting for Areva, not only were we successful in having their trademark infringement case dismissed, because it's pretty hard to confuse purchasers of nuclear reactors, but their trademark was vulnerable to cancellation because the Canadian company had not sold a new nuclear reactor in Canada in decades. Even big companies can have weaknesses in their trademark portfolios that can be exploited if they get too aggressive. Ultimately, having experienced counsel guide a new business can make a huge difference in helping to navigate the bumps in the road to success.
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