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Ellen Bessner's Financial Prosperity Podcast

Ellen Bessner's Financial Prosperity Podcast

By: Ellen Bessner
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About this listen

 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.2025 Economics Personal Finance
Episodes
  • Welcome to the Financial Prosperity Podcast

    Welcome to the Financial Prosperity Podcast
    Jan 21 2026

    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
    Show More Show Less
    8 mins
  • Big Fat Questions

    Big Fat Questions
    Jan 21 2026

    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

    Show More Show Less
    30 mins
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