The Wealthy Barber Podcast

Our guest this episode is Mike Lipkin — motivational speaker, executive coach and founder of Environics/Lipkin, a Toronto-based research and motivation company. Mike has spoken to more than a million people across 43 countries, authored 18 books on leadership and high performance, and has built his career around helping people play at their best.

In this episode, Dave and Mike dive into what it takes to build a life of purpose in retirement, starting with the sobering statistics linking retirement and depression and why so many men in particular struggle once they stop working. They cover the habits that keep you energetic and fit as you age, including six daily practices that can extend your life span, the case for mini home workouts and the neuroscience behind why personal growth matters more than ever in your later years.

The conversation also gets personal. Mike opens up about his own battle with severe depression and how he rebuilt his life, shares inspiring stories of lifelong learning and choosing impact over comfort, and warns about the atrophy that can set in early in retirement if you don't stay involved. He also reflects on balancing travel and independence in marriage, his spectacular success investing in tech stocks, lessons from 44 years of marriage and a preview of his upcoming book.

Whether you're approaching retirement, already there or simply want to age with more energy and purpose, this episode is full of practical wisdom you can put to work right away. 

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Mike Lipkin

(04:08) Retirement and Depression Statistics

(07:45) Staying High Energy and Fit as You Age

(09:39) Six Daily Habits to Extend Your Life Span

(12:08) The Benefits of Mini Home Workouts

(14:09) Mike's Story About Overcoming Depression and Rebuilding

(17:03) Why Men Struggle with Purpose in Retirement

(18:59) The Neuroscience of the Importance of Personal Growth in Retirement

(21:23) Staying in Shape as You Age

(23:29) Inspiring Stories of Lifelong Learning

(26:17) Impact Over Comfort

(28:06) The Danger of Atrophy in Early Retirement if You Don't Stay Involved

(31:44) Balancing Travel and Independence in Marriage

(33:53) Mike's Spectacular Success Investing in Tech Stocks

(39:51) Lessons From 44 Years of Marriage

(42:35) Mike's Upcoming Book

(45:21) Conclusion

Our guest this episode is Brian Portnoy — behavioural finance expert, founder and CEO of Shaping Wealth and author of "The Geometry of Wealth" and "The Investor's Paradox." Brian holds a PhD from the University of Chicago, is a CFA charterholder and spent more than two decades in the financial industry. His mission is helping people use their money to underwrite a meaningful life.

In this episode, Dave and Brian dive into behavioural finance and the fast-changing world of financial advice. They explore the challenges of building an AI coach that's genuinely helpful, the lessons Brian took from Morningstar and the hedge fund industry, and why "simplicity on the far side of complexity" is worth striving for. They also break down the investor's paradox, choice overload and how thoughtful choice architecture can combat decision fatigue.

The conversation also traces the 50-year arc of financial advice, from product-pushing to planning to the human side of money, and why good financial planning can sometimes feel like marriage counselling. Along the way, Brian shares the difference between being rich and being wealthy, the impact of his "funded contentment" concept and his perspective on growth, hope and defining "enough."

Whether you're an investor, an advisor or simply someone trying to figure out what money is actually for, this episode is packed with thoughtful insights you won't want to miss.

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Brian Portnoy

(03:52) Shaping Wealth and the Lydia AI Innovation

(06:43) The Challenges of Building an AI Coach

(08:50) Partnering with Conquest Planning Software

(13:15) Lessons from Morningstar and the Hedge Fund Industry

(15:53) Simplicity on the Far Side of Complexity

(20:33) The Investor's Paradox and Choice Overload

(24:04) Decision Fatigue & Choice Architecture

(29:03) The 50-Year Arc of Financial Advice

(33:25) Financial Planning Can Be Like Marriage Counselling

(35:35) The Difference Between Being Rich and Being Wealthy

(40:53) The Impact of the Funded Contentment Concept

(42:03) Growth, Hope, and Defining Enough

(44:08) Conclusion

Our guest this episode is Alexandra Macqueen — CFP professional, Vice President of Learning, Development and Professional Practice at FP Canada and one of Canada's leading voices on retirement income planning. Alexandra has been a practicing financial planner since 2005, taught personal finance at York University's Schulich School of Business and co-authored the bestselling book "Pensionize Your Nest Egg."

In this episode, Dave and Alexandra dive into how retirement planning has changed over the years, from the way rising longevity has reshaped Canadians' awareness of retirement risks to the assumptions that underpin every retirement plan. They cover why financial planning has become harder, when professional advice can pay off for retirees, and the roles FP Canada and the QAFP designation play in raising the standard of advice. Alexandra also breaks down the factors to weigh when deciding whether to commute a defined benefit pension and makes the case for annuities as a retirement planning tool.

The conversation also explores reverse mortgages and how they compare to HELOCs, the "Die With Zero" legacy approach, lessons from "The Millionaire Next Door" and why the timing of CPP and OAS is different for everyone. 

Whether you're nearing retirement or simply want to understand the decisions that will shape it, this episode is packed with practical insights from one of Canada's most respected retirement planning experts. 

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Alexandra Macqueen

(03:07) Why Alexandra Specialized in Retirement Income Planning

(04:32) Why Longevity Has Changed the Awareness of Retirement Planning

(06:56) Assumptions in Retirement Planning

(10:14) Financial Planning Has Become Harder

(12:55) Why Professional Financial Advice Can Pay Off for Retirees

(13:51) What Is FP Canada?

(15:23) What Is the QAFP Designation?

(17:45) The Factors When Deciding to Commute a Defined Benefit Pension or Not

(22:15) Annuities as a Retirement Planning Tool

(25:13) Are Reverse Mortgages an Underappreciated Financial Tool?

(26:30) Reverse Mortgages vs. HELOCs: Which Makes More Sense?

(28:08) Evaluating the Die With Zero Legacy Approach

(29:17) Lessons from "The Millionaire Next Door"

(32:01) It's Harder to Navigate Financial Planning Today

(36:17) The Value of an Outside Voice in Financial Planning for Spouses

(37:54) The Role of Active vs. Passive Investing Strategies

(39:23) When to Take CPP and OAS Is Different for Everyone

(41:20) The Increasing Costs of Assisted Living

(42:44) Teaching Financial Planners the Psychological Aspects of Working with Clients

(45:18) The Reality of Family Adjustments After Retirement

(46:03) The Improvement of the Financial Advice Industry

(47:54) Conclusion

Our guest this episode is Brenda Hiscock, a CFP with Objective Financial Partners, one of Canada's leading advice-only planning firms. Brenda's route to financial planning was anything but easy. She lost her mother as a teenager, faced homelessness, battled addiction and overcame a cancer diagnosis, all while building a decades-long career in Canadian financial services. Today, she draws on those experiences to help clients navigate both the numbers and the emotions of money.

In this episode, Dave and Brenda dive into her remarkable life story: the childhood hardship and early family loss that shaped her, and the turning point that came through therapy, mentorship and self-forgiveness. 

The conversation also explores a wide range of retirement topics, including practical tips for people who start their financial planning later in life, retiring abroad, planning for the potential costs of long-term care and the psychology of actually spending your savings later in life. Brenda shares her thinking on protecting parents' retirements before making gifts to their kids, using trusts to protect generational wealth, RRSP meltdowns, delaying CPP and OAS, and facing retirement with a mortgage. 

This episode is packed with practical insights and an inspiring story you won't want to miss. 

 

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Brenda Hiscock

(02:09) Brenda's Childhood Hardship and Early Family Loss

(05:41) The Trauma of Eviction and Developing an Addiction

(07:31) The Turning Point: Therapy, Mentorship and Self-Forgiveness

(10:54) Overcoming a Cancer Diagnosis and Rebuilding Confidence

(11:54) Tips if You Start Financial Planning Later in Life

(14:10) How Brenda's Life Experiences Have Informed Her Views on Insurance

(16:00) Retiring Abroad

(18:29) Managing Client Fears About the Stock Market

(20:54) Planning for the Looming Potential Costs of Long-Term Care

(22:40) The Psychology of Spending Your Savings Later in Life

(25:08) Protecting Parents' Retirement Before Making Gifts to Their Kids

(27:39) Using Trusts to Protect Generational Wealth

(28:29) RRSP Meltdowns and Delaying CPP/OAS

(30:04) Who Seeks Advice-Only Financial Planning?

(31:01) The Impact of "Millionaire Teacher"

(32:00) Raising the Standards in the Canadian Financial Planning Industry

(35:00) Facing Retirement with a Mortgage

(37:23) Embracing Your Authentic Life Story

(39:50) Conclusion

Our guest this episode is Michael J. Wiener — retired cryptologist and the writer behind the long-running Canadian personal finance blog "Michael James on Money." After a high-tech career in cryptography that produced roughly 20 patents, Michael has spent nearly two decades applying an engineer's rigour to investing and retirement math, helping everyday Canadians make clearer, lower-fee, evidence-based decisions with their money.

In this episode, Dave and Michael dive into the real cost of investment fees, from high-fee group RRSPs to how seemingly small percentages quietly erode a portfolio over decades. They cover the evidence for passive investing over active management, how to optimize RESP contributions, strategies for smoothing taxes on retirement income and whether it makes sense to delay taking CPP and OAS.

The conversation also explores how Michael uses the CAPE ratio to adjust his asset allocation, planning ahead for cognitive decline, the debt paydown vs. investing question and why he's skeptical of Dalbar's famous mutual fund underperformance data. Along the way, Michael shares his takes on real estate investing, reverse mortgages, budgeting for healthcare and long-term care costs, and estate planning essentials.

If you want clear, math-driven thinking on investing and retirement from someone with no product to sell, this episode is packed with insights you won't want to miss.

 

Show Notes

(00:00) Intro & Disclaimer

(00:57) Intro to Michael J. Wiener

(03:09) The Impact of High Fees in Group RRSPs

(05:23) The Big Impact of Seemingly Small Investment Fees

(07:09) Active Management vs. Passive Investing

(08:46) Optimizing RESP Contributions: Lump Sum vs. Ongoing

(12:02) Smooth Taxation Strategies for Retirement Income Planning

(14:49) Should You Delay Taking OAS and CPP?

(17:02) How Michael Uses the CAPE Ratio to Adjust His Asset Allocation

(20:40) Addressing Cognitive Decline and Managing Your Investments

(22:25) Balancing Debt Paydown vs. Investing

(24:21) RRSP vs. TFSA Debate

(25:55) Is a 100% Equity Portfolio Right for Young Investors?

(27:19) Evaluating Dalbar's Mutual Fund Underperformance Data

(30:34) The Realities and Hassles of Real Estate Investing

(33:28) The Hidden Risks and Rules of Reverse Mortgages

(35:01) Common Financial Mistakes Savers Make in Retirement

(36:38) Budgeting for Healthcare and Long-Term Care Costs

(39:47) Cash Value Insurance vs. Term Insurance for Canadians

(41:24) Essential Estate Planning and Power of Attorney Tips

(42:15) The Importance of Decluttering for the Next Generation

(44:07) Engineering, Cryptography, and Quantum Computing Threats

(45:01) The Story Behind Michael's Pseudonym

(45:49) Finding an Initial Audience and Blogging Success

(46:34) Conclusion