Advertise on podcast: The Up Side with Eli the Money Guy

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.     They also get into beneficiary mistakes, mortgage insurance concerns, short-term vs long-term disability, CPP disability, elimination periods, occupation definitions, and what business owners or self-employed Canadians should be thinking about when protecting their income.     This episode is for anyone who wants to understand insurance more clearly and make more intentional decisions before something goes wrong.     For educational purposes only. This is not personal financial, insurance, tax, or legal advice.

In this listener Q&A episode, Eli Kirchmaier and Brandon Murphy answer real financial planning questions from Canadians.   They cover topics including LIRAs, pension transfers, gifting wealth to children, retirement income, taxes, CRA audits, and other common planning questions that can have a significant impact on your financial future.   If you'd like your question featured on a future episode, leave a comment or get in touch with the team at Up Financial.

What separates great financial advisors from average ones? In this episode of The Up Side, Eli sits down with Dylan to discuss the growing importance of technical expertise in financial planning, why education is often overlooked in the industry, and what advisors can do to better serve clients in an increasingly complex financial world. They explore the challenges facing today's advisors, common gaps in industry training, the role of specialization, and why clients need far more than basic investment advice. Whether you're a financial professional, business owner, or someone looking to better understand the value of quality financial planning, this conversation offers practical insights into what truly drives long-term success. Topics discussed: Why education is the ultimate competitive advantage The biggest mistakes new advisors make Why specialization matters Risk tolerance vs. financial goals Building trust with clients The future of financial advice What clients should expect from a great advisor

What happens when you realize you've saved more money than you actually need for retirement? In this episode of The Upside with Eli, Eli sits down with CPA Brandon Murphy to unpack one of the most overlooked financial planning conversations for affluent Canadians: how to strategically manage "excess wealth." From helping adult children with down payments and business capital to estate planning, tax-efficient gifting, and structuring long-term family wealth, Eli and Brandon break down the real decisions wealthy families face once retirement is already secure. They discuss: What "excess wealth" actually means The most common ways affluent families support their children Real estate vs. invested assets Tax considerations around gifting and wealth transfer How retirees think differently once they know they have enough Why intentional planning matters more than ever Whether you're building wealth, approaching retirement, or thinking about your legacy, this episode offers practical insight into how high-net-worth families make smart financial decisions beyond retirement income planning.

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.

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: [email protected] 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!

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

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.

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!

In this episode of The Up Side, Eli sits down with Brandon Murphy, CPA, to break down the real-world tax and accounting questions business owners struggle with most — and the mistakes that quietly cost them thousands. Brandon shares his path to becoming a CPA, why so many entrepreneurs rush into incorporation too early, and how to think strategically about your business structure from day one. Together, they unpack when it actually makes sense to incorporate, how early-stage losses should be handled, and why "looking professional" is rarely a good tax strategy. They also dive into one of the most common questions new business owners ask after incorporating: how do I pay myself? Brandon explains the practical differences between salary and dividends, when simplicity matters more than optimization, and why the "it depends" answer is often the most honest one. If you're a business owner, entrepreneur, or side-hustler trying to make smarter decisions around tax, cash flow, and long-term planning — this episode will help you avoid common pitfalls and take the next right step with confidence.

You've worked hard—now it's time to make every dollar count. Eli the Money Guy and CPA Amal Assad reveal the power moves that can turn your 50s into your most financially rewarding decade yet. From tax-saving hacks to investment tweaks and retirement timing, discover how to retire richer, sooner, and with zero guesswork.

Income splitting is one of the most powerful and legal tax strategies families and business owners can use to save thousands, but it's often misunderstood or underutilized. In this episode, we dive deep into how income splitting works, who qualifies, and the smartest ways to pay family members, use spousal loans, and leverage financial planners to make it all work. We also cover the difference between a financial planner and a tax accountant, and why having the right team can multiply your savings. If you want to stop leaving money on the table and get serious about keeping more of what you earn, this episode is a must-listen.

In this episode of The Up Side, we're unpacking some of the lesser-known but highly powerful tools in the Canadian tax strategy playbook. From maximizing your Principal Residence Exemption to understanding the commuted value of your pension, and getting familiar with flow-through shares, we cover the tax advantages that could be worth thousands (or more). Whether you're planning for retirement, selling property, or investing smarter, this episode is packed with insights you won't want to miss.