Ellen Bessner's Financial Prosperity Podcast

About Ellen Bessner's Financial Prosperity Podcast

The Financial Prosperity Podcast identifies, analyzes, and solves the most common gaps between investors and financial service providers so that you can build long-term financial prosperity, strengthen your financial literacy, and make informed decisions about your money management and future financial planning. Because investors and financial service providers—whether online platforms, individual financial advisors, financial planners, or Portfolio Managers—sit on the same side of the table, the success of one depends on the success of the other. Each episode uncovers a real-world disconnect between investors (around their savings, investing decisions, financial goals, and confidence in sharing information) and financial service providers (their ability to communicate clearly in person, online, or by email by asking the right questions and using the right language and tone). We explain the gap, why these gaps exist, and offer practical, actionable steps to close them—whether you're trying to understand how to choose a financial advisor, evaluate advice, improve communication, or start building long-term wealth. Hosted by lawyer, author, and industry expert Ellen Bessner, the Financial Prosperity Podcast breaks down financial conversations and services in a way that's human, honest, and easy to apply. Listeners gain clarity and confidence on essential topics such as retirement planning, wealth-building strategies, finding the right advisor, and making informed decisions that lead to real, lasting financial prosperity. Ellen Bessner is a leading Canadian lawyer, author, and expert in financial services practices. With decades of experience advising and defending wealth firms and financial advisors, she brings a clear, practical lens to how investors and financial service providers can better understand and bridge communication gaps. Her focus: helping people make confident, well-informed decisions about their money so they can truly achieve financial prosperity.

Publisher

Ellen Bessner

Category

business · business

Language

en

Explicit

No

First episode

21 Jan 2026

Latest episode

30 Sept 2026

Latest episodes

11 episodes in the feed.

1. 

   30 Sept 2026

   Moms are here to help

   Moms are here to help The Gap We're Solving: This podcast addresses a dual challenge in today's financial landscape. For next-generation investors, it provides warm, trusted guidance to help them set and achieve their goals—and find the right financial service provider to support their efforts. For financial service providers, it's a call to evolve: adapting their services and tools to meet the needs of younger investors, rather than simply applying the same approaches used with the baby boom generation. Topics Covered: • How next-gen investors can set themselves up for financial success • The rise of "finfluencers" and risks of unqualified social media financial advice • The great wealth transfer to younger generations and how they can protect their wealth Key Takeaways: • The importance of forging your own financial path • Verify credentials before following any financial influencer online • Financial advisors should tailor their approach to younger clients Pattie Lovett-Reid, Chief Financial Commentator and entrepreneur

2. 

   2 Sept 2026

   The Planning Gap

   The Planning Gap, with Shannon Lee Simmons This episode focuses on the gab between having a financial plan and implementing it, addressing how every Canadian can get a plan that works for them. Key topics: • Why many Canadians don't have a financial plan – the gaps and challenges • Psychological, affordability, and implementation barriers to planning • Why budgeting and living frugally often don't work • How to "pay yourself first" without traditional budgeting • The impact of social media on investor spending habits • Helping the financial service industry with tips and tools to getting clients to open up about sensitive financial subjects • Suggestions for financial service providers on approaching younger generations of investors Shannon Lee Simmons, CFP, CIM – Founder of New School of Finance, bestselling author, Globe and Mail personal finance writer, and CBC Radio's Metro Morning money columnist

3. 

   5 Aug 2026

   Why couples should not divide & conquer financial investment tasks

   Don't Divide and Conquer Financial Investment Tasks Both partners in a relationship should be involved in financial decisions—don't delegate all investing decisions to one person. Scenario: Karla and Adrian split household tasks by preference, but this "divide and conquer" approach shouldn't apply to finances. The Gap: The more financially literate partner often handles meetings or trades alone, while the less literate partner is happy to skip them—but this creates problems. Four Reasons Both Partners Should Be Involved: 1. It's both of your money—you both need a say in investment decisions. 2. Risk tolerance often differs between partners, even when other values align. 3. Financial service providers need to ensure they understand each person and that the financial plan and investments suit both individuals. 4. Both need to understand investments so neither is left vulnerable if something happens to the other. Takeaway: Work together side by side on financial planning and investing—don't divide and conquer; and for financial service providers, use this podcast to explain why it is so important to have both partners involved.

4. 

   8 Jul 2026

   Don't forget to call your advisor!

   Don't forget to call your advisor! Investors should proactively communicate life changes to their financial service providers. Scenario: Whether it's losing a job (like Tricia) or receiving a bonus (like Saidy), these events warrant a call to your advisor. The Gap: Investors often don't call because they don't think of it, assume it's irrelevant, or see no benefit—but these changes can significantly impact their financial plan and investments. Why It Matters: • Advisors can't read minds and won't know your situation unless you share it. • Life changes (job loss, bonuses) affect how you should manage debt, RRSPs, TFSAs, and tax obligations. • Early communication allows for better planning and minimizing financial damage or tax liability. Takeaway: Call your advisor when circumstances change, and for advisors—create a supportive, shame-free environment that encourages clients to share news.

5. 

   10 Jun 2026

   Do You Care?

   Do You Care??? Why Emotional Intelligence Matters in Financial Planning In this episode of the Financial Prosperity Podcast, Ellen Bessner and guest Bryan Borzykowski* explore one of the most overlooked drivers of successful financial planning: whether your financial advisor truly cares. They unpack why money is emotional, how poor communication increases financial stress, and why investors — especially entrepreneurs and sole earners — need advisors who combine technical expertise with empathy and emotional intelligence. Bryan shares his real-world experience navigating business income volatility and family financial responsibilities, and why traditional advisory models often fail to provide the ongoing support investors need to build confidence and long-term financial prosperity. Key topics: • Why emotional intelligence improves financial outcomes • How investor–advisor communication impacts money decisions • What to look for when choosing a financial advisor • How entrepreneurs can find financial planning support that fits • How caring advisors build trust and reduce financial stress Bryan Borzykowski is the Founder, CEO at ALLCAPS Content; a Toronto-based business writer and editor focusing on investing, personal finance and small business. He writes investing features for CNBC and contributes to the New York Times, CNNMoney, BBC, Canadian Business magazine and the Globe and Mail. Bryan has also authored three personal finance books.

6. 

   13 May 2026

   No Shame Planning!

   No Shame Planning! with Shannon Lee Simmons This episode tackles the "shame game" in personal finance, exploring how investors can avoid feeling ashamed about their financial situation and how financial service providers can approach clients without triggering feelings of shame or inadequacy. Key topics: • Empowering clients to move from hopelessness to hopefulness • Managing client expectations to transform unrealistic wish lists into achievable goals • Raising awareness about hte harmful effects of the "keeping up with the Joneses" mindset across generations • Identifying personal spending triggers, such as feelings of inadequacy, to help prevent overspending • Supporting clients who tend to underspend by encouraging them to pay themselves first and enjoy their lives • Guidance for the financial services industry on assisting clients with plan implementation *Guest:* Shannon Lee Simmons, CFP, CIM – Founder of New School of Finance, bestselling author, Globe and Mail personal finance writer, and CBC Radio's Metro Morning money columnist Contact us: ebessner@babinbessnerspry.com | www.babinbessnerspry.com Follow us: @TheFinancialProsperityPodcast Subscribe to our Financial Services & Securities blog

7. 

   15 Apr 2026

   You Don't Want to Bother Each Other?

   Don't Bother Each Other? Why Advisors and Clients Avoid Talking (and Why this is a BIG Problem) In this episode, Ellen Bessner and Brendan Monahan dig into one of the biggest barriers to effective financial planning: lack of communication between investors and advisors. Both sides often avoid reaching out — investors don't want to "bother" their advisor, and advisors worry about appearing intrusive. But silence can seriously harm financial outcomes, especially when life events, market conditions, or priorities shift. Using real examples, Ellen and Brendan explain why ongoing communication is essential for managing risk, adjusting investment strategies, and supporting long-term financial prosperity. They discuss why annual check-ins aren't enough and how regular conversations help clients stay on track with their goals. Key topics: •        Why advisors hesitate to call clients — and why clients stay silent •        How life changes, market changes, and company changes affect your plan •        What happens when you don't update your advisor •        Why annual check-ins aren't enough •        How communication drives better financial decisions •        How staying connected supports retirement planning, future financial planning, and wealth-building Order Ellen's Books: Advisor at Risk: A Roadmap to Protecting Your Business Communication Risk: How to Bridge the Client-Advisor Gap to Protect and Grow Your Business Contact us: ebessner@babinbessnerspry.com | www.babinbessnerspry.com Follow us: @TheFinancialProsperityPodcast Subscribe to our Financial Services & Securities blog

8. 

   18 Mar 2026

   How to Find the Right Advisor (and the Right Clients)

   How to Find the Right Advisor (and the Right Clients) This episode of The Financial Prosperity Podcast focuses on one of the most searched financial topics: how to choose a financial advisor. Ellen Bessner and Brendan Monahan walk listeners through how to find a qualified, registered advisor or portfolio manager, and how advisors can ensure they're working with clients who genuinely fit their practice. They explore why the search is often overwhelming, how to check advisor registration, and why the advisor–client relationship needs to be the right match on both sides. Ellen shares common mistakes investors make early in their financial journey, while Brendan outlines practical steps for starting your search — from referrals to dealer websites to financial planning portals. They also explain how to combine online financial platforms with human advisors, how to prepare for your first meeting, and what questions help investors identify red flags and assess whether an advisor aligns with their financial goals. Key topics: •        How to know if an advisor is properly registered •        Where to start your search (referrals, bank-owned dealers, independent dealers, planners) •        Common investor mistakes to avoid •        Questions to ask in your first meeting •        How advisors assess whether a client is a good fit •        What makes an advisor–client relationship succeed •        How choosing the right advisor supports long-term financial planning and wealth-building Resources mentioned: Government of Canada – Choosing a Financial Advisor FP Canada — Find a Planner (https://financialplanningforcanadians.ca/find-planner) Ellen's Investor Guide – Communication Risk Order Ellen's Books: Advisor at Risk: A Roadmap to Protecting Your Business Communication Risk: How to Bridge the Client-Advisor Gap to Protect and Grow Your Business Contact us: ebessner@babinbessnerspry.com | www.babinbessnerspry.com Follow us: @TheFinancialProsperityPodcast Subscribe to our Financial Services & Securities blog

9. 

   18 Feb 2026

   Relationship with Money

   Relationship with Money:  Why understanding your money story is essential to financial prosperity In this episode, Ellen Bessner and Brendan Monahan explore one of the most influential — and overlooked — elements of financial literacy: your relationship with money. They break down how childhood experiences, habits, fears, and beliefs shape the way adults save, spend, invest, and plan for the future. Ellen shares how her early experiences created money anxiety, while Brendan explains how recognizing these patterns helps investors make clearer decisions, communicate better with advisors, and improve their long-term wealth-building strategies. They also discuss how individuals using online platforms can self-reflect to improve their financial planning. Key topics: • What "relationship with money" really means • How past experiences impact spending, saving, and planning • Signs your money mindset may be holding you back • Questions advisors can ask to help clients open up • How investors can self-reflect and communicate their needs • Whether and how you can change your money mindset • Why emotional awareness leads to better financial outcomes and planning for the future Order Ellen's Books: Advisor at Risk: A Roadmap to Protecting Your Business Communication Risk: How to Bridge the Client-Advisor Gap to Protect and Grow Your Business Contact us: ebessner@babinbessnerspry.com | www.babinbessnerspry.com Follow us: @TheFinancialProsperityPodcast Subscribe to our Financial Services & Securities blog

10. 

    21 Jan 2026

    Big Fat Questions

    Big Fat Questions: Why advisors ask personal questions — and how to make the conversation more comfortable. In this episode of The Financial Prosperity Podcast, Ellen Bessner and guest Brendan Monahan explore a common challenge in financial planning: the discomfort investors feel when advisors ask personal questions about income, savings, debt, and goals. These details are essential for building a financial plan for the future, yet many adults hesitate to share them. Ellen introduces her "Big Fat Questions" — open-ended, human-first questions that help financial advisors understand clients as whole people, improving money management conversations and strengthening advisor–client communication. Brendan shares why this approach builds trust, reduces anxiety, and leads to better outcomes for investors seeking long-term financial prosperity. Key topics: • Why investors avoid sharing personal financial information • Why advisors legally and practically need these details • How assumptions lead to poor financial outcomes • How "Big Fat Questions" help close the communication gap • How advisors can earn the right to ask sensitive questions • How clear communication supports better financial planning and wealth-building Order Ellen's Books: Advisor at Risk: A Roadmap to Protecting Your Business Communication Risk: How to Bridge the Client-Advisor Gap to Protect and Grow Your Business Contact us: ebessner@babinbessnerspry.com | www.babinbessnerspry.com Follow us: @TheFinancialProsperityPodcast Subscribe to our Financial Services & Securities blog

11. 

    21 Jan 2026

    Welcome to the Financial Prosperity Podcast

    Welcome to The Financial Prosperity Podcast In this first, introductory, episode we kick off by providing real life examples of mistakes made by both investors and investment service providers which create friction and hold investors back from identifying and meeting their  goals. If you are an investor or prospective investor or if you participate in providing financial services (CIRO registered, securities commission registered, insurance registered, financial planners) this podcast is for you. In this podcast we'll break down these gaps and solve for them in a simple, relatable, non-technical way — from building better money habits to improving communication with your financial service providers. By solving for these gaps we aim to achieve: Happy investors and happy financial service providers! Make sure to follow The Financial Prosperity Podcast so you don't miss any episodes. If you find the content helpful, share it with those who could also benefit. Order Ellen's Books: Advisor at Risk: A Roadmap to Protecting Your Business Communication Risk: How to Bridge the Client-Advisor Gap to Protect and Grow Your Business Contact us: ebessner@babinbessnerspry.com | www.babinbessnerspry.com Follow us: @TheFinancialProsperityPodcast Subscribe to our Financial Services & Securities blog

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Spotify

5.0 / 5

2 ratings

Contact Ellen Bessner's Financial Prosperity Podcast

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.