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Behind the Business with Anna Friend & Jessie Dobson


Annastasia Friend and Jessie Dobson have been the voice for those unable to speak for themselves. They have provided a sense of security through their unique approach to the law field.

Making it Personal

Celebrating its four-year anniversary, Friend and Dobson is a full-service law firm with the exception of criminal. Located in Port Perry and Bobcaygeon, their services include litigation, family law, business law, wills and estates, real estate, and agricultural legal issues. Being a local firm, Friend and Dobson’s main focuses are quality and personalized legal services tailored to the unique needs of their clients.

Founders Anna Friend and Jessie Dobson state the sole intention of the firm is to ‘practice law differently’ — as it is their belief that legal services should be both flexible and cost-effective.

Since their initial start-up in 2018, the firm has expanded, welcoming new members to the team, such as Morgan Arndt, who practices in family law, and real estate.

Upon majoring in history and philosophy at York University, Anna journeyed to Hawaii to complete her Bachelor of Arts in history. Anna then completed her Juris Doctor from the William S. Richardson school of law, later being called to the Hawaii bar in 2001. Anna practices in family law, real estate, wills and estates, corporate law, and agricultural law. One of her many notable achievements is that she is a panel member for the Office of the Children’s Lawyer, a particularly meaningful component of her practice.

Attending the University of Toronto also for a Bachelor of Arts in history, Jessie later went on to obtain her Juris Doctor from the University of Toronto, Faculty of Law. While working with the Toronto Legal Services Branch of the Ministry of Community Safety and Correctional Services, she had opportunities to assist in a number of high-profile legal matters. Jessie practices in civil litigation and family law.

Giving Back

Both Anna and Jessie grew up not far from Port Perry and saw numerous business opportunities throughout the town’s popular main street. Their spacious and newly renovated office provides a sense of security and order to its inhabitants and makes it a welcome place for all. The firm’s unique specialization in agricultural law attracts clients from all across the GTA. They utilized their knowledge of the local traditions and consumer trends, which resulted in them developing a loyal locally based clientele.

Starting out as a two-person firm, Friend and Dobson has grown exponentially since the beginning of the COVID-19 pandemic. The pandemic altered the way many people do business, the same goes for Friend and Dobson. Friend and Dobson offered virtual services throughout the duration of the first lockdown as well as the entirety of the pandemic. They wanted to be the ones not only inspiring change in the industry but also participating and advocating for it.  During the pandemic Friend and Dobson ensured our frontline workers had their minds at ease by offering free wills to all frontline workers. Doing so they conducted over $80,000 in free legal work.

Follow Through

Having the freedom to choose how they approach their practice is one of the major benefits of being a business owner, according to Anna and Jessie. As with everything in life, with benefits there arises challenges. People often utilize the expression “We have all the time in the world”, however people fail to realize that time is in fact an extremely limited resource. In regards to the business world, time can be a challenging thing. Managing time between the office and home, as well as balancing time with quality of services, is the most challenging obstacle for businesses and business owners alike. After all, life is one big balancing act.

“There have been many female lawyers that came before us — we’re fortunate because we didn’t have any major hurdles stopping us from opening our firm or practicing [law], because the women before us paved the way.” — Anna Friend

That said, sometimes challenges can create opportunities. Jessie and Anna believe that it is important to leverage your connections. Utilize the tools, people, and skills around you. Be resourceful and adaptable. Finding someone that inspires you that can act as a mentor can also help motivate and challenge you to always to meet your potential.

Figure It Out, Because You Can

Knowing the area has also been a benefit to Anna and Jessie. The ability to reach clients locally with messages that appeal to them has been very effective, but the best results have always come from word-of-mouth. They say treat your customers well and they will do the advertising for you.

Another way to put your best business foot forward is to hire the right people and treat them well. Good employees know their roles and responsibilities and execute them with care. Trust in your employees, trust that they will do their job and do it well. But most importantly treat them well and with respect.

You also have to be brave and confident in business. Not everyone is going to like everything you say or do, people are going to have an opinion. It’s how you choose the approach that determines whether or not it is beneficial. Feedback creates motivation in the mind of an employer. Businesses are always searching for new ways to improve, therefore making consumer feedback vital.

Although the future may lay uncertain for some, the future of Friend and Dobson is certainly brighter than ever. With the expected addition of more lawyers, increased diversity and representation, as well as the potential for more offices. 

Considering Anna and Jessie’s family-oriented nature, it’s fair to say they’ve formed a new family of their own within the community, as they continue to impact the lives of many.

#FunFact: The life of a lawyer is a hectic and busy one, however, Anna and Jessie have their own ways of winding down after a busy week at the office. Anna is an avid Harry Potter fan and spends her days off curled up with a good book. Whereas, Jessie enjoys spending time in the garden and riding horses. Both value spending time with family.


Festive Downtown Open House

Festive Downtown Open House

Join the festivities at Port Perry's Festive Downtown Open House! Explore local shops, take advantage of the amazing...