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

• The differences between a bank financial advisor and a private wealth manager

• How investment risk and financial priorities change as you build wealth

• Why preserving wealth requires a different approach than accumulating it

• How inheritance, estate planning, and family business succession can create unexpected conflicts

• Why personalized financial planning matters, especially for Canadians

• The risks of relying on AI-generated financial plans

• How social media can create unrealistic expectations about wealth

• Why ongoing relationships with financial advisors matter

Whether you're approaching retirement, managing significant investments, navigating family wealth, or wondering whether your current financial advisor is the right fit, this conversation offers a closer look at what thoughtful wealth management involves.

Learn more about Up Financial: upfinancial.ca/book

Connect with Eli: @elithemoneyguy

Connect with Myles Martin: @milesmoneystrategies

Subscribe to The Up Side for conversations about Canadian wealth management, retirement planning, investing, tax strategies, and financial decisions that matter.

#WealthManagement #FinancialPlanning #CanadianFinance

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

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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