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Keen on Retirement

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Retirement planning with discipline and perspective.

The gist

Keen on Retirement brings a conversational advisor-table feel to retirement planning. Bill Keen, Steve Sandusky, and Matt Wilson connect market noise, tax rules, family goals, and long-term portfolio discipline to the decisions retirees actually face.

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About Keen on Retirement

Keen on Retirement is a retirement-planning show with the feel of a standing conversation among experienced financial voices. It is calm, but not vague. Episodes often begin with weather, family, travel, or a small joke, then shift into the heavier decisions behind a successful retirement plan. The show spends a lot of time on the tension between safety and growth. Too much cash can feel comfortable while inflation quietly erodes purchasing power. Too much stock exposure can create a different kind of risk when withdrawals are happening at the same time. That kind of tradeoff is where the show tends to live. Bill Keen, Steve Sandusky, and Matt Wilson discuss portfolios, taxes, spending, Social Security, Medicare, insurance, estate documents, cybersecurity, charitable giving, and the personal relationship between families and an advisory team. Their market commentary is usually framed around discipline. AI disruption, international investing, rolling recessions, tariffs, and Dow milestones become prompts for asking whether a plan is diversified, current, and executable. The tax episodes are especially checklist-minded. They stress that rules change, sunsets matter, and seemingly small planning moves can compound over years. The show also widens the definition of retirement beyond balances and brackets. Time with family, travel, sailing, purpose, adventure, and the second half of life are treated as legitimate planning subjects. That gives the show a human rhythm. It is not just about maximizing numbers. It is about making decisions that hold up across markets, laws, health changes, family transitions, and ordinary uncertainty. The conversations are candid and sometimes technical, but they stay grounded in examples that a pre-retiree or retiree can recognize. Listeners looking for hot takes may find it too measured. Listeners who want steady, advisor-led context for consequential household decisions are the natural fit.

Made for: Pre-retirees, retirees, and financially established families who want practical guidance on income, taxes, investing, and life after work. It also fits listeners who prefer steady planning conversations over headline-driven market talk.

What sets it apart: The show blends technical retirement planning with personal context, moving from tax brackets and portfolio allocation to family time, purpose, and long-term discipline. Its strength is the recurring emphasis on executing a real plan instead of reacting to volatility or trends.

In their own words

Do you want to make smarter decisions about your money and your life? Do you want to make sure you have enough money to retire comfortably? Join Founder and CEO of Keen Wealth Advisors, Bill Keen, as we discuss money, life, and everything in between. Whether you're on your way to retirement or already there, these shows will educate and entertain you on your journey.

As heard by us

Based on 6 episodes we listened to · September 2026

Retirement headlines become practical conversations about spending, allocation, uncertainty, and the life a portfolio is meant to sustain.

Keen on Retirement turns big financial questions into planning conversations grounded in the realities of drawing income from a finite pool of assets.

Read our full review in PlayNext →

Why you'd press play

Dow 100,000 gets a rounding referee; your retirement nerves get a reality check.

Press play if you want

  • to test a daunting Dow number against the math instead of your pulse
  • to understand why playing it too safe can leave your savings exposed to inflation
Read the full recommendation in PlayNext →
retirement spendinginflation and volatilityportfolio diversificationtax planningSocial Security and MedicareAI and market disruptionfamily and purpose in retirementadvisor-client relationships

Talks about

Business & FinancePersonal FinanceRetirement Planning

Podcasts like Keen on Retirement

Episodes

  1. 1

    The Power of Purpose in Your 2025 Planning

    ·45m
  2. 2

    Staying the Course Through AI Upheaval, Tax Changes, and Geopolitical Uncertainty

    ·48m
  3. 3

    What Questions Should Retirees Be Asking … BEFORE They Retire?

    ·43m
  4. 4

    Navigating the 2026 Tax Landscape: Why You Need a "Human in the Loop"

    ·45m
  5. 5

    Weighing the Pros and Cons of Medicare Advantage Plans

    ·39m
  6. 6

    How to Feel Confident Living Off Your Assets Rather Than a Monthly Paycheck in Retirement

    ·36m
  7. 7

    Stephany Bening Shares Her Remarkable Story of Faith and Forgiveness

    ·53m
  8. 8

    How to Avoid Getting Caught Up in Financial Fraud

    ·37m
  9. 9

    Love and Community Helped My Mother Thrive in Her Golden Years

    ·30m
  10. 10

    Answering Listener Questions about Security Theft, Double-Dipping Donations, and Tariff Checks for Seniors

    ·42m
  11. 11

    How the "One Big Beautiful Bill" Is Changing the Tax Landscape for Retirees

    ·41m
  12. 12

    Words of Wisdom for Redefining Wealth in 2026

    ·45m
  13. 13

    Is Dow 100,000 Closer Than You Think?

    ·50m
  14. 14

    Are You on Track for an "Average" Retirement?

    ·47m
  15. 15

    Avoid These 3 Wrong Turns from the Kyle Busch Insurance Lawsuit

    ·41m
  16. 16

    Managing Risks and Uncertainty Around the Government Shutdown, Stock Prices, and Market Bubbles

    ·45m
  17. 17

    Will Tax Rates and the Government Shutdown Affect Your 2026 Financial Planning?

    ·39m
  18. 18

    Lessons on Managing Life-Changing Money from Lotto Winners and Successful Retirees

    ·35m
  19. 19

    Special Guest Carissa Keen on How the Keen Wealth Foundation Is Making an Impact and Sharing Guidelines to Help You Evaluate Your Own Charitable Giving Strategy

    ·42m
  20. 20

    One Retirement Question, Two Different Answers: Who Should We Trust?

    ·44m
  21. 21

    Should Private Equity Investments Be Part of Your Retirement Plan?

    ·39m
  22. 22

    A Keen Wealth Case Study: Can We Retire Comfortably at 65?

    ·51m
  23. 23

    Don't Engage: Protecting Your Info and Your Money from the Latest Scams

    ·41m
  24. 24

    What Seniors Need to Know About The One Big Beautiful Bill and Their Retirement Plans

    ·42m
  25. 25

    What to Know and What to Ask When You're Searching for a Financial Advisor

    ·44m
  26. 26

    One, Big, Beautiful Podcast About 2025 Tax Policy

    ·41m
  27. 27

    Should You Consider Taking Social Security Before Age 70?

    ·40m
  28. 28

    Keen Wealth's Q2 Market Update: Who's Driving Market Moves and How Should Investors React?

    ·41m
  29. 29

    4 Warning Signs That You Might Be Receiving Bad Financial Advice

    ·47m
  30. 30

    Should Tariffs and Market Volatility Change Your Retirement Timeline?

    ·39m
  31. 31

    Could Tariff Turbulence Create Opportunities for Your Financial Plan?

    ·46m
  32. 32

    Answering Last-Minute Tax Questions and Preparing for 2025

    ·39m
  33. 33

    4 Common and Costly Tax Prep Mistakes That Your Advisor Can Help You Avoid

    ·33m
  34. 34

    The Hidden Money Traps That Could Derail Your Retirement

    ·36m
  35. 35

    Natural Disasters, Bitcoin, and Market Uncertainty: What Every Investor Needs to Know to Stay Sane and Solvent

    ·36m
  36. 36

    Here's How Social Security, Retirement Planning, and Taxes are Changing in 2025

    ·34m
  37. 37

    Should Your Retirement Spending Change Due to Inflation and Volatility?

    ·47m
  38. 38

    Should Seniors Give It All Away like Buffett or "Die with Zero"?

    ·42m
  39. 39

    A Keen Wealth Case Study: Planning for Early Retirement Before Age 60

    ·47m
  40. 40

    What a Second Trump Term Could Mean for Social Security, Taxes, and Interest Rates

    ·39m
  41. 41

    3 Financial Strategies You and Your Advisor Should Consider Before December 31st

    ·38m
  42. 42

    Answering Your Questions About the Next Recession, AI Investing, and the Federal Deficit

    ·45m
  43. 43

    Will Almost Half of Retirees Run Out of Money?

    ·36m
  44. 44

    Will the 2024 Presidential Election Change How Your Capital Gains Are Taxed?

    ·38m
  45. 45

    Reflecting on the Historical and Financial Lessons of 9/11

    ·33m
  46. 46

    5 Keys to Protecting Your Money and Your Relationships When Lending to Loved Ones

    ·30m
  47. 47

    Weighing the Pros and Cons of Taking Social Security at Age 62

    ·35m
  48. 48

    Get Tax Smart: Insights on Gold, Mistakes, and IRA Forms

    ·48m
  49. 49

    What Impact Will the 2024 Elections Have on Your Financial Plan?

    ·44m
  50. 50

    Customizing Your Estate Plan to Your Family's Unique Needs

    ·39m
  51. 51

    A Keen Wealth Advisors Case Study: "Can We Retire With a $3.3 Million Nest Egg?"

    ·41m
  52. 52

    A Comprehensive Financial Plan for Achieving an Early Retirement Goal

    ·39m
  53. 53

    Using a Team-Based, Comprehensive Financial Planning Approach to Secure Your Retirement Future

    ·38m
  54. 54

    Retirement on the Horizon? Here's What You Need to Know About the Economy in 2024

    ·47m
  55. 55

    Will Hitting "Peak 65" Rewrite the Rules for Retirement?

    ·31m
  56. 56

    Retirement Planning Strategies for Managing Interest Rates, Investment Yields, and 529 Accounts

    ·39m
  57. 57

    Keen on Retirement at 200: Reflecting on Our Favorite Episodes

    ·42m
  58. 58

    Setting New Year's Goals and Ignoring Old Noise in 2024

    ·45m
  59. 59

    Lessons on Smart Investing and Rich Living from Charlie Munger

    ·40m
  60. 60

    Crossing Three Listener Questions Off Your 2024 Financial Planning Checklist

    ·39m
  61. 61

    Add Daily Thanksgiving to Your Holiday Routine

    ·36m
  62. 62

    Coordinating Bonds, Market Returns, and Taxes into a Personalized Retirement Strategy

    ·37m
  63. 63

    How Social Security, Medicare, and Geopolitics Could Affect Your 2024 Planning

    ·37m
  64. 64

    Your Guide to 2023 Medicare Open Enrollment

    ·37m
  65. 65

    4 Case Studies Using Keen Wealth's Comprehensive Planning

    ·41m
  66. 66

    Following Up on Our Latest Webinar on Maximizing Social Security Benefits

    ·37m
  67. 67

    Protect Your Info and Your Money from Fraud with These Cybersecurity Tips from Jeff Lanza

    ·43m
  68. 68

    Busting 4 Myths About the "Sacred Cows" Hurting Your Financial Plan

    ·34m
  69. 69

    Discussing our Q3 Market Outlook, Bonds, Recessions, and Student Loan Debt

    ·39m
  70. 70

    What Taylor Swift's Tour Can Teach Us About the "Eras" of Retirement

    ·39m
  71. 71

    Answering Your Questions About Paying Taxes in Retirement

    ·34m
  72. 72

    The Latest on Interest Rates, Inflation, and Your Retirement Plan

    ·33m
  73. 73

    Can Financial Planning Help You Get More Happiness From Your Money?

    ·40m
  74. 74

    Keen Wealth's Checklist for Caring for Elderly Relatives

    ·34m
  75. 75

    Answering Your Questions About the Debt Ceiling, Bank Closures, and the Market Outlook

    ·42m
  76. 76

    Tax Season May Be Ending But Effective Tax Planning Never Stops

    ·35m
  77. 77

    Answering Your Questions about Retirement Spending

    ·42m
  78. 78

    Insights on Interest Rates, the Banking System, and Your Financial Plan from the 2023 Barron's Summit

    ·41m
  79. 79

    Answering Your Questions About "Timing" the Retirement Transition

    ·40m
  80. 80

    From 38 Years at Black & Veatch to Living a Full Retirement

    ·37m
  81. 81

    Answering Listener Questions on the SECURE Act 2.0 and Maximizing Retirement Resources

    ·24m
  82. 82

    What Can You Expect in a First Meeting with Keen Wealth Advisors?

    ·44m
  83. 83

    What's New for Retirees in SECURE Act 2.0?

    ·41m
  84. 84

    Follow Your Values Towards Better Goals in 2023

    ·32m
  85. 85

    Henderson Engineers Puts People First with New ESOP

    ·49m
  86. 86

    Lessons in Successful Long-Term Planning from the 2nd Edition of Keen on Retirement

    ·33m
  87. 87

    Do Gold and Real Estate Fit Inside Your IRA?

    ·37m
  88. 88

    Reviewing the Latest Changes to Social Security, Medicare, and Inherited IRAs

    ·33m
  89. 89

    Are We Going to Be OK? A Keen on Retirement Case Study

    ·36m
  90. 90

    What Market Fluctuations Mean for Your Retirement Plan

    ·38m
  91. 91

    Answering Your Questions About Maximizing Social Security Benefits

    ·31m
  92. 92

    Anticipating Changes to Social Security and Medicare in 2023

    ·37m
  93. 93

    What Retirees Need to Know About the Inflation Reduction Act

    ·31m
  94. 94

    Creating a Legacy Plan That's More Than Just Your Money

    ·35m
  95. 95

    Answering Listener Questions During a Volatile Summer

    ·46m
  96. 96

    Embracing Optimism and Looking for Investment Opportunities

    ·41m
  97. 97

    Separating the Good News from the Bad Headlines in the Latest Social Security Report

    ·40m
  98. 98

    Developing a Healthy Relationship With Money

    ·49m
  99. 99

    Recession Worries, I Bonds, and More Listener Questions

    ·37m
  100. 100

    Put a Bow on 2025 With Our Year-End Tax Planning Checklist

    Wealth advisor Bill Keen discusses proactive year-end tax planning strategies and the importance of coordinating with CPAs to maximize after-tax returns for retirement.

    ·41m
  101. 101

    Should Your Retirement Spending Change Due to Inflation and Volatility?

    Hidden gem

    Financial advisors discuss how retirees naturally adjust spending during tough economic times and the role of advisors in managing retirement spending.

    Apr 8, 2026·47m·2 clips
  102. 102

    Staying the Course Through AI Upheaval, Tax Changes, and Geopolitical Uncertainty

    Hidden gem

    Bill, Matt, and co-host Steve examine AI tax preparation, including incorrect K-1 readings, outdated tax rules, and uncertainty over taxpayer liability for filing errors.

    Mar 25, 2026·48m·3 clips
  103. 103

    What Questions Should Retirees Be Asking … BEFORE They Retire?

    Wealth advisor Bill Keen discusses the critical financial documents and planning steps retirees should consider before retirement, including vesting schedules, taxation, and benefit coordination.

    Mar 11, 2026·43m
  104. 104

    Navigating the 2026 Tax Landscape: Why You Need a "Human in the Loop"

    Wealth advisors discuss the importance of proactive tax planning for substantial portfolios to achieve significant long-term tax savings.

    Feb 25, 2026·45m
  105. 105

    Answering Listener Questions about Security Theft, Double-Dipping Donations, and Tariff Checks for Seniors

    Bill Keen and his co-hosts answer listener questions about security theft, double-dipping donations, and tariff checks for seniors, while also discussing a recent boat show trip.

    Feb 11, 2026·42m
  106. 106

    How the "One Big Beautiful Bill" Is Changing the Tax Landscape for Retirees

    This episode of Keen on Retirement opens with host Bill Keen describing a family trip to Brisbane and the Gold Coast, Australia — including a 16-hour nonstop American Airlines flight from Dallas, driving on the left side of the road after 30 hours of travel, and watching Bindi Irwin perform the crocodile show at the Australian Zoo.

    Jan 29, 2026·41m·2 clips
  107. 107

    Words of Wisdom for Redefining Wealth in 2026

    In episode 253 of Keen on Retirement, recorded in January 2026, hosts Bill Keen, Matt, and Steve discuss redefining wealth through personal quotes, frameworks, and client stories.

    Jan 14, 2026·45m·3 clips
  108. 108

    Is Dow 100,000 Closer Than You Think?

    Bill Keen, Steve, and Matt examine whether the Dow could reach 100,000 after approaching 50,000 in December 2025.

    Dec 31, 2025·50m·3 clips
  109. 109

    Are You on Track for an "Average" Retirement?

    Hidden gem

    Keen on Retirement uses Warren Buffett, the Dow Jones Industrial Average, and Fidelity’s retirement data to frame how wealth compounds over decades.

    Dec 17, 2025·47m·2 clips
  110. 110

    Put a Bow on 2025 With Our Year-End Tax Planning Checklist

    Hidden gem

    Wealth advisor Bill Keen discusses proactive year-end tax planning strategies and the importance of coordinating with CPAs to maximize after-tax returns for retirement.

    Dec 3, 2025·41m·2 clips
  111. 111

    Avoid These 3 Wrong Turns from the Kyle Busch Insurance Lawsuit

    Nov 19, 2025·41m
  112. 112

    Managing Risks and Uncertainty Around the Government Shutdown, Stock Prices, and Market Bubbles

    Nov 5, 2025·45m
  113. 113

    Will Tax Rates and the Government Shutdown Affect Your 2026 Financial Planning?

    Oct 22, 2025·39m
  114. 114

    Lessons on Managing Life-Changing Money from Lotto Winners and Successful Retirees

    Oct 8, 2025·35m
  115. 115

    Special Guest Carissa Keen on How the Keen Wealth Foundation Is Making an Impact and Sharing Guidelines to Help You Evaluate Your Own Charitable Giving Strategy

    Carissa Keen discusses the Keen Wealth Foundation's local charitable work and offers guidelines for evaluating personal giving strategies.

    Sep 24, 2025·42m
  116. 116

    One Retirement Question, Two Different Answers: Who Should We Trust?

    Sep 10, 2025·44m
  117. 117

    Should Private Equity Investments Be Part of Your Retirement Plan?

    Aug 27, 2025·39m
  118. 118

    A Keen Wealth Case Study: Can We Retire Comfortably at 65?

    Aug 13, 2025·51m
  119. 119

    Don't Engage: Protecting Your Info and Your Money from the Latest Scams

    Jul 30, 2025·41m
  120. 120

    What Seniors Need to Know About The One Big Beautiful Bill and Their Retirement Plans

    Jul 16, 2025·42m
  121. 121

    What to Know and What to Ask When You're Searching for a Financial Advisor

    Jul 2, 2025·44m
  122. 122

    One, Big, Beautiful Podcast About 2025 Tax Policy

    Jun 4, 2025·41m
  123. 123

    Should You Consider Taking Social Security Before Age 70?

    May 21, 2025·40m
  124. 124

    Keen Wealth's Q2 Market Update: Who's Driving Market Moves and How Should Investors React?

    May 7, 2025·41m
  125. 125

    4 Warning Signs That You Might Be Receiving Bad Financial Advice

    Apr 23, 2025·47m
  126. 126

    Should Tariffs and Market Volatility Change Your Retirement Timeline?

    Apr 9, 2025·39m
  127. 127

    Could Tariff Turbulence Create Opportunities for Your Financial Plan?

    Mar 26, 2025·46m
  128. 128

    Answering Last-Minute Tax Questions and Preparing for 2025

    Mar 12, 2025·39m
  129. 129

    4 Common and Costly Tax Prep Mistakes That Your Advisor Can Help You Avoid

    Feb 26, 2025·33m
  130. 130

    The Hidden Money Traps That Could Derail Your Retirement

    Feb 12, 2025·36m
  131. 131

    Natural Disasters, Bitcoin, and Market Uncertainty: What Every Investor Needs to Know to Stay Sane and Solvent

    Jan 29, 2025·36m
  132. 132

    Here's How Social Security, Retirement Planning, and Taxes are Changing in 2025

    Jan 15, 2025·34m
  133. 133

    The Power of Purpose in Your 2025 Planning

    Dec 31, 2024·45m
  134. 134

    Should Seniors Give It All Away like Buffett or "Die with Zero"?

    Bill Keen and his co-hosts discuss whether seniors should give away their wealth like Warren Buffett or spend it all, inspired by the 'Die with Zero' philosophy.

    Dec 18, 2024·42m
  135. 135

    A Keen Wealth Case Study: Planning for Early Retirement Before Age 60

    Dec 4, 2024·47m
  136. 136

    What a Second Trump Term Could Mean for Social Security, Taxes, and Interest Rates

    Nov 20, 2024·39m
  137. 137

    3 Financial Strategies You and Your Advisor Should Consider Before December 31st

    Nov 6, 2024·38m
  138. 138

    Answering Your Questions About the Next Recession, AI Investing, and the Federal Deficit

    Oct 30, 2024·45m
  139. 139

    Will Almost Half of Retirees Run Out of Money?

    Oct 9, 2024·36m
  140. 140

    Will the 2024 Presidential Election Change How Your Capital Gains Are Taxed?

    Sep 25, 2024·38m
  141. 141

    Reflecting on the Historical and Financial Lessons of 9/11

    Sep 11, 2024·33m
  142. 142

    5 Keys to Protecting Your Money and Your Relationships When Lending to Loved Ones

    Aug 28, 2024·30m
  143. 143

    Weighing the Pros and Cons of Taking Social Security at Age 62

    Aug 14, 2024·35m
  144. 144

    Get Tax Smart: Insights on Gold, Mistakes, and IRA Forms

    Jul 31, 2024·48m
  145. 145

    What Impact Will the 2024 Elections Have on Your Financial Plan?

    Jul 17, 2024·44m
  146. 146

    Customizing Your Estate Plan to Your Family's Unique Needs

    Jul 3, 2024·39m
  147. 147

    A Keen Wealth Advisors Case Study: "Can We Retire With a $3.3 Million Nest Egg?"

    A financial advisor discusses a case study about retiring with a $3.3 million nest egg, balancing data and emotions in planning.

    Jun 19, 2024·41m
  148. 148

    A Comprehensive Financial Plan for Achieving an Early Retirement Goal

    Jun 5, 2024·39m
  149. 149

    Using a Team-Based, Comprehensive Financial Planning Approach to Secure Your Retirement Future

    May 22, 2024·38m
  150. 150

    Retirement on the Horizon? Here's What You Need to Know About the Economy in 2024

    May 8, 2024·47m