Keith Brown



Business Family Advisor

Keith’s passion is creating financially confident family businesses that are set up to successfully and harmoniously transition to the next generation. He has spent a lifetime developing and honing his expertise, starting with working in his parents’ business, and continuing today, as his son becomes deeply involved in the family business.


Keith is the founder and president of Financial Confidence™, his current family business, but it’s not the first business he has founded or transitioned. As a 19-year-old, still young and care-free, he was obliged to suddenly take over and run his parents’ business, one that was lacking supporting structures and was in no way prepared for his leadership as the next generation. There is nothing like experience, and having been thrown into the fire, Keith learned quickly, but not without many challenges and hardship along the way.

However, that experience inspired his entrepreneurial spirit. In 2002, determined to help others avoid his experience as a young, unprepared successor, Keith founded Financial Confidence™ to help clients plan and prepare for the inevitable transition of their businesses and wealth to future generations. The next entrepreneurial venture for Financial Confidence™, is to empower his son, Dylan, to take over the business, in a smooth and structured transition.

In 2003 he co-founded Daystar Financial Group Inc. with another business family and grew it into a thriving business with 75+ staff and over 2200 distributors. They then sold the Daystar business in 2013 and facilitated a smooth transition from a multi-family-run business to HUB International, a large multi-national firm, currently ranked 7th among the world’s largest insurance brokers.

Keith’s experience, combined with his extensive knowledge gained over 35 years of working in insurance and financial planning, has given him a deep understanding of the unique challenges and opportunities family businesses face as they look to the future and the next generation.

With the depth and breadth of his experience, Keith has become a prominent industry leader across Canada; most notably known for a strategic approach that successfully protects wealth and skillfully facilitates a transition of leadership and ownership for businesses and families. As such, he is frequently called upon to speak at industry conferences and events including: ADVOCIS (The Financial Advisors Association of Canada), FEX (Family Enterprise Exchange), CALU (Conference for Advanced Life Underwriters), CAILBA (Canadian Association of Independent Life Brokerage Agencies), CICA (Canadian Institute of Chartered Accountants), AMTC (Agency Management Training course), CAFÉ Family Business, amongst others.

To further support entrepreneurial families, Keith authored “The Business Family Advisor: Providing Structured Transitions for Business and Wealth”. In his book, he identifies the most common challenges family businesses face and provides the framework to ensure a successful transition for their business and personal wealth.


Keith has a fundamental belief that continuous learning is an essential contributor to both happiness and success, and as such, he has achieved many designations including: Certified Financial Planner (CFP), Chartered Life Underwriter (CLU); Chartered Financial Consultant (CH.F.C); Family Enterprise Advisor (FEA) and Certified Exit Planner (CExP™). Keith is a member of the Estate Planning Council and sits on several private company boards. He also participates in various committees within CALU and chairs the Value of Advice Working Group.

Keith embraces a pay-it-forward philosophy in his work and beyond and looks forward to empowering clients as they build a legacy and successfully transition their businesses and wealth to the next generation.