Our guest this episode is Jason Pereira — Senior Partner & Financial Planner at Woodgate Financial and one of Canada’s most prolific voices in the financial planning industry.
Jason has spent over two decades immersed in the world of financial planning — earning nine professional designations, contributing to hundreds of articles and podcasts and becoming a trusted expert on everything from practice management to fintech to insurance strategy.
In this wide-ranging conversation, Dave and Jason explore the evolution of financial advice in Canada including how it compares globally, why many Canadians still have blind trust in big institutions and what younger advisors are doing differently. They also dig into some of the thorniest financial planning topics: over- and under-insurance, capital gains at death, intergenerational wealth transfers, life insurance for children, rental real estate in 2025 and much, much more.
Jason doesn’t hold back — sharing candid insights on the gaps in Canada’s advisory landscape and how consumers can better navigate the system. Whether you’re a new investor or just someone trying to make smart decisions with your money, this episode is packed with thought-provoking ideas and practical takeaways.
Show Notes
(00:00:00) Intro & Disclaimer
(00:00:55) Intro to Jason Pereira
(00:02:13) The Different Ways to Pay for Financial Advice
(00:05:26) How Does Canada’s Financial Advisory Industry Compare to Other Parts of the World?
(00:10:52) Young Advisors Want To Do More Financial Planning
(00:12:57) Canadians Have Misguided Trust in Large Financial Institutions
(00:16:17) Jason Thinks People Are Being Sold Too Much Insurance They Don’t Need
(00:19:06) Term vs. Cash Value Insurance
(00:21:27) Using Insurance to Cover Large Capital Gains Taxes
(00:25:25) Passing On Cottages Can Cause Much Family Friction
(00:26:45) Corporate Executors
(00:29:37) Many Young Canadians Don’t Have Enough Life Insurance
(00:34:50) How Much Life Insurance Do You Need?
(00:41:20) Buying Life Insurance on Young Children
(00:44:54) It’s So Hard to Max Out All of Your Registered Accounts
(00:46:23) AI and Financial Planning
(00:52:59) Rental Real Estate in 2025
(00:55:32) Any Risks with the Rise of Passive Investing?
(00:58:13) Parents Are Gifting More Money
(01:00:39) When Financial Advisor Fees Are Worth It
(01:04:10) Conclusion
