Your partner in personalized, full-service wealth management

Your ally in the pursuit of financial freedom

We go beyond managing money—we focus on optimizing your financial journey by fusing technology, modern strategies, and core values like integrity, transparency, and balance. We provide honest, personalized advice and a proactive, high-touch experience.

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Meet the team

Dawn Kennedy

Wealth Planner

Dawn Kennedy

Wealth Planner

Dawn Kennedy has been working in finances for over 30 years, and is still deeply enthusiastic about her work. She prides herself on her extensive knowledge of the industry, letting her tackle any challenges her clients might face.

Her specialties include financial planning, tax planning, and estate planning. Dawn makes it a point to prioritize client education, making sure that complex financial concepts are explained as clearly and concisely as possible. She always takes the time to fully understand her client’s unique goals and circumstances.

Dawn believes that strong communities are made from the charity of individuals, and is active in many local charities, including the Rotary Club of Mildmay, Advocis, the Mildmay Community Health Foundation and Mildmay Carrick Homecoming.

Dawn currently lives on an active beef farm with her parents, husband, children, and grandchildren. Outside of work, she loves travelling, reading, and socializing.

Email: dawn.kennedy@optimize.ca
Phone: (226) 840-3295

Julia Gutscher

Associate

Julia Gutscher

Associate

Email: julia.gutscher@optimize.ca
Phone: (226) 840-3295

Nick Cup, MBA, CFP®, CIM®

Portfolio Manager

Nick Cup, MBA, CFP®, CIM®

Portfolio Manager

Nicholas Cup is a Portfolio Manager at Optimize. He specializes in overseeing investments of clients’ comprehensive financial strategies, making sure adjustments align to their unique goals. With more than 12 years of experience, he’s fluent in retirement cash flow planning, investment management, tax and estate strategies, and insurance planning. Nicholas is an MBA graduate and has acquired both the Certified Financial Planner and Chartered Investment Manager designations.

Nicholas believes financial peace of mind begins with a clear plan and diversified portfolio, not just market returns. He takes pride in helping clients make informed decisions and works closely with advisors to build personalized, long-term solutions.

Outside of work, Nicholas enjoys spending weekends at the cottage with his family and dog, as well as golfing, cycling, and running.

Email: nick.cup@optimize.ca
Phone: (416) 900-3887

Stuart Hinshelwood, CIM®

Associate Portfolio Manager

Stuart Hinshelwood, CIM®

Associate Portfolio Manager

Stuart Hinshelwood is an Associate Portfolio Manager at Optimize who helps clients select investment strategies that match their goals and risk tolerance. He works closely with clients and advisors to create resilient portfolios that adapt as client needs and markets change. He strives to provide clarity on how investment decisions support long-term outcomes.

Early in his career, Stuart was inspired when he listened to a Portfolio Manager speak passionately about his job. He was drawn to the profession’s combination of continuous learning and the opportunity to make a genuine difference.

For Stuart, the most rewarding part of his role is simplifying complex financial concepts into comprehensible action plans. He takes pride in breaking down sophisticated topics into clear, straightforward guidance that helps clients feel confident in their decisions.

Beyond his role at Optimize, Stuart enjoys an active lifestyle of hockey, lacrosse, golf, tennis, cycling, and chess. He also values time with his family and being involved in his kids’ sports and activities.

Email: stuart.hinshelwood@optimize.ca
Phone: (416) 964-5297

Team values

Client-First Approach

The Kennedy Group prioritizes exceptional, personalized service, treating every client as an individual with unique goals and needs. By focusing on building trust and fostering meaningful relationships, we make sure each client feels valued and supported. Our client-first philosophy drives every decision, meaning our strategies are tailored to achieve meaningful outcomes and long-term financial success.

Integrity as a Guiding Principle

Honesty, transparency, and ethical practices are the foundations of The Kennedy Group. Our team is committed to providing clear, unbiased advice and open communication at every step of the financial planning process. By consistently putting our clients’ best interests at the forefront, we create trusted partnerships that inspire confidence.

Our dedication to excellence is
reflected in every aspect of our work

Clients can expect a proactive, high-touch experience designed to simplify and enhance their financial lives. At 4 Pillars Wealth, we believe in consistently going above and beyond to deliver exceptional service and build lasting relationships. This means not only addressing clients' current needs but also anticipating future challenges and opportunities, helping them feel confident and prepared for what lies ahead.

Empowering Clients Through Knowledge

At The Kennedy Group, staying informed and knowledgeable is our top priority. Our team continually tracks industry trends in order to provide expert guidance that reflects the latest developments. By offering up-to-date strategies and empowering clients through education, we make sure that every decision is well-informed. This commitment to education helps our clients pursue their financial goals with clarity and assurance.

Supporting our community

Dawn Kennedy is an active member of the Rotary Club of Mildmay, committed to creating positive, lasting change. Through Rotary, Dawn supports initiatives that strengthen communities locally and around the world. Her involvement helps provide opportunities for young people to build leadership skills, foster global understanding, and inspire service. Dawn’s dedication reflects her passion for making a meaningful difference wherever she can.

Since 2018, Dawn Kennedy has served as an Advocacy Officer with Advocis, Canada's oldest and largest professional association of financial advisors. In this role, Dawn promotes education, professional development, and advocacy within the financial services community. She helps create valuable networking opportunities for advisors from all companies, encouraging collaboration and the exchange of best practices to better serve clients.

Since 2021, Dawn Kennedy has served as Treasurer for the Mildmay-Carrick Homecoming Executive Committee. In this role, she helps organize a five-day celebration held every ten years, welcoming current and former residents back to the community. Through preparing a variety of activities and events, Dawn plays a key part in fostering community spirit and connection, helping make sure that each homecoming is a memorable and meaningful experience.

Your partner in personalized, full-service wealth management

Your ally in the pursuit of financial freedom

Meet the team

Dawn Kennedy

Wealth Planner

Julia Gutscher

Associate

Nick Cup, MBA, CFP®, CIM®

Portfolio Manager

Stuart Hinshelwood, CIM®

Associate Portfolio Manager

Team values

Client-First Approach

Integrity as a Guiding Principle

Our dedication to excellence is reflected in every aspect of our work

Empowering Clients Through Knowledge

Supporting our community

Our dedication to excellence is
reflected in every aspect of our work