The Up Side with Eli the Money Guy

The Retirement Planning Mistakes Costing Canadians Millions

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.

How to Transition from Accounting to Wealth Management (& Build a Real Brand)

In this episode, Eli sits down with Brandon Murphy to unpack a career path that more people in finance are starting to consider, but few talk about openly. If you've ever felt stuck in a technical role or wondered what it actually takes to move beyond "just doing the numbers," this conversation is for you. Eli and Brandon break down the transition from accounting into wealth management, including the mindset shifts, skill changes, and real-world challenges that come with stepping into a more client-facing, advisory role. They also get into: * Why many professionals in finance feel stuck (even when they're successful on paper) * The difference between being an expert and being a trusted advisor * How personal brand plays a bigger role than most people think * What to consider before making a move into wealth management Whether you're early in your career or already established and looking for something more, this episode will give you a clearer perspective on what's possible—and what it actually takes to get there. If you enjoy the episode, don't forget to follow the show and share it with someone who's thinking about their next move in finance. Work with Eli / Up Financial Book a call: https://upfinancial.ca/book/ Email: up@upfinancial.ca Instagram: https://www.instagram.com/elithemoneyguy/ Tik Tok: https://www.tiktok.com/@elithemoneyguy Connect with Brandon Instagram: https://www.instagram.com/murphonmoney/ Tik Tok: https://www.tiktok.com/@murphonmoney Subscribe for weekly episodes!

Tax Loss Harvesting Explained: How to Turn Market Losses Into Tax Savings

Markets down? That doesn't mean your portfolio has to lose. In this episode of The Upside with Eli, Eli and portfolio manager Dylan break down how to actually use investment losses strategically — not just take them. They cover: * What tax loss selling actually is * How to use losses to offset capital gains * What "tax loss crystallization" means (and when to use it) * The superficial loss rules (and how to avoid them) * Strategies to stay invested while still capturing tax benefits * Advanced approaches like transferring losses and tax loss purification If you're holding losses or just want to be more tax-efficient — this episode shows how to make the most of a bad market

Should You Take the Commuted Value? Interest Rates, Taxes & Retirement Flexibility

Tens of thousands of federal employees are facing job uncertainty — and many have a defined benefit (DB) pension with an option most people don't realize exists: taking the commuted value (a lump sum) instead of lifetime monthly payments. In this episode of The Upside, Eli sits down with Dylan Reber (Portfolio Manager + CFP®) to break down what a commuted value actually is, how it's calculated, and the biggest decision factors to consider — including interest-rate timing, tax implications (maximum transfer value), locked-in accounts (LIRA), longevity, estate planning, inflation indexing, and investing discipline. If you're approaching age 55, considering early retirement, or navigating a job transition, this conversation will help you ask the right questions before making an irreversible pension decision.

What You NEED to Know Before Tax Season: RRSP Deadline, Deductions & OAS Clawback

Tax season is coming fast — and we're answering your most common Canadian tax questions with CPA Brandon Murphy. In this Q&A, we break down the 2026 tax season deadlines, the RRSP contribution deadline, when to expect T-slips, what deductions people miss (like childcare, home office, and vehicle expenses), why self-employed filers still need to pay by April 30, and how OAS clawback really works (including dividend gross-ups). Have a question you want us to cover next? Send it to us!