Becca Brennan grew up in Toronto and recently moved back after almost 15 years in New York City, where she attended undergraduate university and law school. She worked in corporate law in NYC for a couple years before branching out on her own and establishing a solo consultancy practice. She is currently working toward a license to practice law in Canada while transitioning her business to Toronto.

Becca Brennan’s legal studies focused on intellectual property. She dreamt of being a trademark attorney- helping clients establish and defend their trademarks and branding. Right out of law school, she practiced corporate tax law, always trying to be a part of the IP projects that came up while also taking every opportunity to develop expertise in the finance side of things. Becca Brennan’s social life kept leading her to meeting small business owners, many of whom needed legal advice about the ins and outs of owning and running a small business . She quickly realized she loved helping these creative, yet definitely all Type A’s, get their bearings and eventually decided to go out on her own.

Becca Brennan began with trademark prosecution and defence, ultimately expanding to corporate structuring and day-to-day client needs. Her client-base is mainly in the hospitality and entertainment industries, which she says makes sense in that she values true engagement in all aspects of her client’s fields and these are the industries she has interest in outside of work. It means working with creative people in creative fields and ensures no two days are the same. Becca is admittedly not a huge fan of sitting in front of a screen all day, and her job and particular clientele means she is constantly traveling and meeting people face-to-face (this year, excepted, of course).

Why did you return to Toronto?

After spending almost half my life in NY, I needed a change of scenery. I packed up all my belongings and two dogs and drove Toronto to spend time with friends and family, thinking it was a temporary visit while I decided where to settle next. I, of course, ended up loving it here and decided to make it my new home. I wanted to be able to  have always hoped to expand my consultancy to Canadian-based clients and continue to leverage my legal background here, so I’ve spent the past year studying and working towards the licenses I need to practice law in Canada.

Why did you decide to create your own business?

I started my own business because of the flexibility.  I love being able to focus all my energy on clients and projects I’m excited about. I like choosing how to load my plate. This usually means a pretty loaded plate, but I find I work more efficiently when I have a million things going on. I’m not especially fond of sitting in an office all day, so I love being able to travel- whether it be to meet with a client or just work remotely. A couple of years ago I managed to continue working while living in Mexico City for 6 weeks. I don’t think I could have ever done that while working for a firm.

Working for myself and running my own business means I have a practical understanding of the day-to-day issues and situations my clients are going through. My legal background helps me see that big picture, but my personal experiences help me to see the little picture and the little tidbits in between and help my clients strategize and build solutions to tackle the big and small.

The only downside to going off my own is the camarederie of working as part of a team. Especially when I was just starting out, the fact that I was constantly surrounded by and working with brilliant, hard-working lawyers was truly invaluable. Not having a built-in support system like that means I’ve had to work hard to create my own network of experts who I can turn to when faced with a challenge or a topic I’m not familiar with.

Why did you decide on Consulting?

I opted for consulting because it means I get to be a part of every aspect of a business.  Consultants are expected to have a broad expanse of general knowledge and, it sounds corny, but I truly love to learn. And I truly love being a part of helping someone realize their dream. Being a small-business owner is so hard and you need someone in your corner to drown out all the other distractions. I love being that person in your corner- with a metaphorical water bottle and towel. Or actual water bottle and towel, if need be.

Piece of advice I’ve never forgotten

I saw this quote on one of those inspirational Instagram posts that pop up on the Explore feed: ‘the past is like using your rear view mirror;  it’s good to glance back and see how far you’ve come, but if you stare too long you’ll miss what’s right in front of you.’ I’m not one to fall for motivational instagrams, but this really resonated for me. I read it as giving yourself permission to consider your past, but not to use it in moving forward. Especially this year with quarantine and travel restrictions, I can’t help but feel stagnant every now and then, especially with everything going on this year. But, if I’m to have a smooth drive, I need to look forward and work on making sure there are no obstacles in the way.

What do you love most of your industry?

I think I veered towards the hospitality industry because I know it. My first job (at 13) was a waitress at a tiny sandwich shop. I waited tables through college and law school. And I loved every minute of it. I know and can anticipate the challenges owners and managers will face and am able to creatively guide them towards solutions.  To be honest, I just fell into the entertainment industry because that’s where many of my friends worked. This work is more focused on the individual as a small business, and is equally exciting and challenging. No two days are alike and in the end, I helped create something tangible.

Any suggestions for someone starting in your industry?

I’ve often joked that if I wrote a memoir, it would be called ‘You Know What You Should Do.’ Because, if you start your own business, everyone and their mother is going to tell you what you need to do in order to be successful. Don’t listen to them. Listen to yourself and focus on sticking to your own plan and your own gut. You can’t and definitely won’t make everyone happy, and if you try to make everyone happy you’ll only end up making yourself miserable. Take on only what you can and want to, and give it 100%.

What trends in the industry most excite you?

While it’s due to miserable circumstances, I truly believe the shift towards working from home is a godsend for quality of life and quality of this world. I really never understood the whole commute-to-a-little-box-in-the-sky-and-work-for-a-set-amount-of-hours-every-day mentality. I completely respect and understand those who do, but it was just never for me. I work really hard, but sometimes that means waking up at 5am and being done by 3pm because that’s when I work best. And if I have to focus on writing a document, I do it best while sitting on my couch watching Netflix. This doesn’t work for everybody, but if it works for someone I think that it’s great to have that option with this new lifestyle and really hope it continues. Besides that, just the fact that people don’t have to drive to and from work everyday is just so much better for the planet. I remember seeing those photos of L.A. before and after March 2020 and you could actually see the skyline. Just because people weren’t commuting to work! Also, I used to take the subway to and from midtown when I was a corporate attorney. I was constantly sick and only when I stopped my commute did I realize I was just catching a cold from standing shoulder to shoulder with a stranger every morning during rush hour. Anyway, despite the awful reasons for why it took shape, I think that the newly widespread working from home culture is great (despite everything that went it to making it happen) and will lead to increased productivity and a better quality of life for most people.

As someone who has always championed small businesses, another trend I am loving the focus on small, local, and minority and women-led companies that we’ve seen in the media lately. Once I’m licensed to start practicing in Canada, I’m planning to devote at least half of my time to under-represented small business clients on  a pro bono or sliding-scale basis.