From Corporate Law to Retail

From Corporate Law to Retail

After six years of practicing corporate law, Raegan Kennedy left Bay street to start Little White Sneakers, a kids clothing store. They sell pre-owned designer and boutique kids clothing, as well as brand new locally-made clothes and overstock and sample pieces. Starting out as an online store just two years ago, Little White Sneakers has already grown to two bricks and mortar locations in Toronto.

We talked to Raegan about practicing law, how she decided to start Little White Sneakers, and the challenges she experienced in leaving law.

The Road to Law School

Raegan did not originally plan on going to law school. Having studied science in her undergrad, she was headed towards life in a lab or medical school, neither of which appealed to her. She took a couple of years off and spent that time teaching at a boarding school in Switzerland. Although she really enjoyed teaching, she found a lot of difficulty in motivating children that did not love to learn in the same way that she did. Realizing that teaching might not be for her, Raegan began to look into law school with the idea of eventually becoming an environmental lawyer.

“It was a default move. I knew I would learn a lot of great stuff and that it was a valuable education to have.”

After law school, Raegan articled at Torys LLP in Toronto. She practiced corporate law for six years, mostly doing M&A and financing transactions.

Leaving Law

Raegan enjoyed practicing law, but would occasionally question the hours and the stress that comes with working at a big law firm. However, those thoughts never lasted long, and she would “put her head down” and get back to work.

“There were times when I thought I would do it forever but other times the stress would catch up with me and I would think about my options.”

The idea to quit law and start her own business came about when Raegan was on maternity leave for her second child. At the time, Raegan’s cousin, Kara (and later co-founder) was also on maternity leave and they were spending a lot of time together. They began toying with the idea of starting a business together but were unsure about what exactly it would be.

“It was something that was so foreign to me, thinking about leaving my established career.”

They originally were looking into buying a business but ended up coming up with their own idea while talking about their experiences as parents. Raegan had been looking through her eldest daughter’s baby clothes to find hand-me-downs for her second daughter and realized that they had been worn through after only a couple of wears. Meanwhile, Kara’s daughter had just grown out of her white running shoes after only three wears. Drawing on these experiences, the idea for Little White Sneakers was born!

In the remainder of her maternity leave, Raegan started work on the new business, preparing a business model, stocking initial inventory and developing the website. With these pieces in place, she quit her job when they were ready to launch.

“It takes time to build something and I wouldn’t have been able to do it in my busy job.”

Taking on a New Role

Kara and Raegan started with their online store two years ago selling only second-hand kids clothes. Six months later they decided to open a physical store to avoid high shipping costs and allow the customers to see the quality of the clothes in person.

Little White Sneakers buys their clothes from Toronto families, either up front or on consignment. They have also started to bring in some new items to fill gaps in their inventory, including pieces from local and organic lines, and overstock from other established brands.

Raegan and Kara now start their mornings by discussing their goals and what needs to be done that day, and they collaborate on every decision. Of course, because of their strengths and experiences, oftentimes one will be better suited for a specific task. For example, because Kara was a marketing director at Telus, she is very suited for the marketing aspect of the business, while Raegan excels at negotiations and ironing out nitty-gritty details.

One aspect of her job that Raegan appreciates is being her own boss and having the flexibility she needs to raise her family.

“I really like the flexibility now. If I want to be there for school pick-up, I can make that happen.”

The Transition

Raegan felt very prepared to start her own business because of the research she had done and the people she had talked to. She knew from the beginning that retail was a tough business and it would take some time to break even. Like any good lawyer, she was prepared for anything and everything.

She also credits her work in corporate law for preparing her because she had a lot of exposure to different companies and industries, and saw how they strategized and made decisions. Her skills as a lawyer, like being detail-oriented and foreseeing risk, help her everyday in running her business.

One thing both Raegan and Kara found to be essential in growing their business is their ability to learn and adapt when needed.

“We try to be open-minded with our business.”

When they first started out, they didn’t expect to be opening physical locations but they followed the demand and adapted when they needed to make a change.

Not-So-Legal Advice

Raegan’s first piece of advice for lawyers thinking about leaving law is figure out why you want to leave. If you like law but do not like an aspect of working at a firm, then consider looking for in-house counsel positions. If it’s because you do not love the law, then it’s time to start getting creative and figuring out what you’re passionate about.

Her second piece of advice is use your network and learn from others.

“One thing I found so helpful was talking to other entrepreneurs and ‘retired’ lawyers and hearing about their experiences.”

You can learn a lot by listening to other people’s journeys (or reading about them here).

The last thing she stated was do not be scared of change or risk.

“The nature of the profession is avoiding risk and a lot of lawyers are pretty risk adverse, which could be a major hurdle to overcome.”

There will be risk in any change, but lawyers are trained to assess risks and take steps to minimize it. Without taking a risk, you will never know what you can or cannot accomplish.