Show Notes
Most retirement plans fail for one reason: they were never actually planned. In this episode of The Up Side with Eli, Eli sits down with portfolio manager and retirement specialist Dylan Rieberer to break down the most common (and costly) retirement mistakes Canadians make. From CPP and OAS timing mistakes to poor RRSP/RRIF drawdown strategies, sequence of returns risk, tax traps, LIRA/LIF planning, income splitting, and retirement portfolio construction, this episode dives deep into the financial decisions that can quietly cost retirees hundreds of thousands...or even millions...over their lifetime. You'll learn: • Why generic retirement advice can be dangerous • How poor drawdown strategies destroy wealth • The biggest CPP & OAS timing mistakes • Why many retirees overpay tax unnecessarily • How sequence of returns risk can derail retirement • The difference between accumulating wealth and drawing it down properly • Why retirement investing is completely different from growth investing If you're approaching retirement, or already retired, this episode could save you from some very expensive mistakes.
More from The Up Side with Eli the Money Guy
What does your bank actually do for your wealth, and what changes when you move to private wealth management? In Episode 18 of The Up Side, Eli Kirchmaier sits down with Myles Martin, Private Wealth Consultant at Up Financial to discuss what he learned from nearly a decade working at a major Canadian bank, why he made the move to private wealth management, and what Canadians should understand about building, protecting, and transferring wealth. From the limitations of traditional banking to the family conflicts that can arise during inheritance and estate planning, Eli and Myles explore the financial decisions that become increasingly important as your wealth grows. They also discuss the growing use of AI tools like ChatGPT and Claude for financial planning, why generic advice can overlook important Canadian tax considerations, and how social media can distort our perception of financial success. In this episode, you'll learn: Why Myles left traditional banking for private wealth management
Selling a business is one of the biggest financial events most business owners will ever navigate, and some of the most valuable planning needs to happen years before the deal closes. In this episode of The Up Side, Eli is joined by Brandon Murphy, CPA, to break down what business owners should be thinking about before a sale. They cover how to determine whether you actually have a sellable business, why planning should begin well before an LOI arrives, share sales versus asset sales, QSBC qualification and the Lifetime Capital Gains Exemption, corporate purification, business valuations and intergenerational transfers. They also discuss what happens after the sale, from managing the proceeds and potential tax obligations to investing for retirement and planning for the next stage of your wealth. If selling or transferring your business could be in your future, this episode will help you understand the decisions worth making before a buyer is at the table.
What actually happens when the CRA audits you, and what can you do if you disagree with their decision? In this episode of The Up Side, Eli sits down with Dove Whitman, Partner in KPMG Law's Tax Litigation and Dispute Resolution practice, to unpack what happens when a tax issue turns into a dispute with the government. Dov explains why getting professional help early in an audit can make a significant difference, what the path from an audit to Tax Court can look like, and one of the biggest misconceptions taxpayers have: that challenging the CRA is pointless. They also discuss how to know when an audit may be escalating, when it makes sense to push back, why documentation can become critical years after a transaction takes place, and the mistakes that can make an already difficult CRA dispute even harder. In this episode: • What actually happens during a CRA audit or tax dispute • When to bring in a tax litigation lawyer • Why Tax Court isn't simply an extension of the CRA • When to cooperate with the CRA and when to push back • Early signs that an audit may be escalating • Why keeping old tax and transaction records matters • What taxpayers should know before taking a dispute further Whether you're a business owner, investor, or high-net-worth Canadian navigating a complex tax situation, this conversation offers a look at what happens on the other side of a CRA dispute and how to better protect yourself before one begins.
Most Canadians know they should probably have insurance, but very few know how much they actually need, what kind to buy, or which policies may not be worth paying for. In this episode of The Up Side, Eli is joined by Dylan to break down the biggest life and disability insurance questions people should be asking before they buy. They cover how to calculate life insurance needs, why "just cover the mortgage" may not be enough, the difference between term and permanent insurance, when insurance starts to make sense, and why employer group coverage often does not tell the full story.
In this listener Q&A episode, Eli Kirchmaier and Brandon Murphy answer real financial planning questions from Canadians.