Your Money, Your Wealth

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Retirement math with a side of banter.

The gist

Your Money, Your Wealth works through real listener retirement cases, from Roth conversions and Social Security timing to 72T withdrawals, pensions, annuities, and big taxable accounts. The tone is loose, but the math is constant: spending, taxes, withdrawal rates, and what can go wrong if the plan is too neat.

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About Your Money, Your Wealth

Your Money, Your Wealth is built for people who bring messy retirement questions, not tidy hypotheticals. The show reads through detailed listener cases and then tests them against the math that actually matters. Ages matter. Account types matter. Spending matters more than almost anyone wants to admit. Joe Anderson CFP and Big Al Clopine CPA spend a lot of time on Roth conversions, Social Security timing, early retirement bridges, required minimum distributions, annuities, pensions, taxable brokerage accounts, and the tax drag that can hide inside a large nest egg. The conversations move fast, but they rarely float above the numbers. A listener might have a large portfolio, a looming layoff, and stock options to sort out. Another might have a smaller portfolio, no heirs, no budget, and a paid-off car. The show gives both cases attention without pretending they are the same problem. It is especially useful for listeners who already know the basics and want to hear how planning choices change when income, taxes, family, and timing collide. Early retirement plans get a skeptical but fair treatment. A 72T election may sound like a clever bridge, but the show asks what happens if the strategy boxes the household in. Roth conversions are treated the same way. Sometimes they are obvious. Sometimes capital gains, future tax brackets, or inheritance goals make the answer less clean. The style is part calculator session, part table talk. Listener nicknames, car details, drink preferences, and old movie references break up the density without replacing the analysis. Andy Last appears as the executive producer presence who sets up episodes and keeps the audience moving into each case. The show can be dry, blunt, and lightly amused by overconfident plans, but it stays anchored in practical tradeoffs. Its best moments come when a complicated question becomes a few levers: spend less, convert slowly, delay claiming, work longer, shift risk, or accept that the plan is probably fine. That makes it a strong fit for retirement planners who want useful uncertainty instead of one-size-fits-all certainty.

Made for: Best for retirement-focused savers, early-retirement planners, and financially curious households who already have real numbers to think through. It especially suits listeners comparing Roth conversions, Social Security timing, tax strategy, pensions, spending rates, and family support decisions.

What sets it apart: The show stands out by doing practical case math in public, with real listener balances, ages, spending targets, and tax questions driving the conversation. It feels less like a lecture and more like experienced planners stress-testing a plan at the table.

In their own words

Making fun of finance. A US News & World Report "Top 9 Personal Finance Podcast" (2025) and "Top 12 Retirement Podcast" (2023). One of the "10 Best Personal Finance YouTube Channels" (CardRates, 2023). "Best Retirement Podcast With Humor" (FIPhysician, 2020-2024). Learn strategies that can help you retire successfully. Financial advisor Joe Anderson, CFP® and certified public accountant Big Al Clopine, CPA answer your money questions and spitball on your 401k, IRA, Roth conversions and backdoor Roth IRA, how to pay less taxes, asset allocation, stocks and bonds, real estate, and other investments, Social Security benefits, capital gains tax, 1031 exchange, early retirement, expenses and with…

As heard by us

Based on 6 episodes we listened to · September 2026

Detailed listener finances become approachable retirement case studies, with taxes, withdrawal choices and timing tested against the numbers.

Your Money, Your Wealth turns detailed listener scenarios into practical retirement analysis. Joe Anderson and Big Al Clopine work directly from household savings, spending, pensions and account balances, testing choices against tax brackets and the years money may need to last.

Read our full review in PlayNext →

Why you'd press play

A $2.2 million retirement account becomes a bee sting; your tax questions get numbers and jokes.

Press play if you want

  • Joe and Big Al to test an early retirement date against what you actually spend
  • your Roth conversion hunch challenged with tax bracket math
Read the full recommendation in PlayNext →
Roth conversionsearly retirement bridgesSocial Security claimingrequired minimum distributionstaxable brokerage strategypensions and annuitiesinheritance and gifting decisionsretirement spending rates

Talks about

Best episodes of Your Money, Your Wealth

Short reviews from the PlayNext desk, based on the episodes we processed.

Could You Lose Half Your Retirement Income to Taxes?Mar 10, 2026

A $2.2 million balance looks smaller once taxes and timing start taking their cut.

Your Money, Your Wealth spends the hour on a simple but useful warning: retirement balances can look far larger on paper than they do after taxes and timing get their say.

Retire Early in Your 40s or 50s: Green Light or Reality Check?Mar 3, 2026

Early retirement plans are tested against bridge money, spending, and retirement-account strategy.

Early retirement is the real center of the conversation, with the focus staying on bridge money, spending burn, and whether a brokerage account can realistically carry someone from 53 to Social Security.

Retirement Planning for Aging Parents - and Can You Retire Early?Feb 24, 2026

Retirement math gets personal when aging parents, pensions, and early exits share the same spreadsheet.

Retirement planning turns personal here before it turns technical. Daniel in Texas is 40 and looking ahead to the possibility of supporting aging parents if their money runs out, while Gemma considers whether guaranteed income would help her 82-year-old mother or cause…

Retirement Changes at These 5 Major Financial CrossroadsFeb 17, 2026

Five retirement crossroads are tested against cash flow, taxes, timing, and the lifestyle a portfolio needs to support.

Retirement timing gets worked from several angles: a 42-year-old considering a private-equity offer, David managing a million-dollar portfolio on his own at 66, Bebe and Shell planning their last year of retirement contributions, Joel looking at required minimum distributions,…

0% Capital Gains Tax vs. Roth Conversion vs.... a Cruise?

A grounded retirement-money discussion about taxes, inheritance, Social Security, bonds and one very specific cruise decision.

Retirement advice is at its clearest when tax strategy runs into a real household choice, and this episode stays in that useful territory. Nancy in Washington is looking at a 401(k) loan that would pay herself back at 9% interest, while Brian in Naperville, Illinois, asks…

When Roth Conversions Don't Make Sense (And When They're a No-Brainer)

A practical Roth conversion discussion for listeners balancing tax brackets, RMDs, and spending needs.

Roth conversions are treated here as a planning question, not a default recommendation. Jill Anderson, CFP, and Big Al Clopine, CPA, move through several listener situations: TJ in PA with large capital gains, a New England couple over 70, Viking Barnsey's tax-deferred accounts,…

Podcasts like Your Money, Your Wealth

Episodes

  1. 1

    How Much Money Do You Need to Retire in 2026?

    ·35m
  2. 2

    When Should You Take Social Security? (Don't Screw This Up)

    ·45m
  3. 3

    Could You Retire Tomorrow If You Had To?

    ·40m
  4. 4

    Could You Lose Half Your Retirement Income to Taxes?

    ·51m
  5. 5

    Retire Early in Your 40s or 50s: Green Light or Reality Check?

    ·45m
  6. 6

    Retirement Planning for Aging Parents - and Can You Retire Early?

    ·46m
  7. 7

    Retirement Changes at These 5 Major Financial Crossroads

    ·44m
  8. 8

    Tax-Smart Investing at Every Age: Starting Young or Catching Up

    ·44m
  9. 9

    Rising Costs and Retirement Unknowns? Here's What to Do - 567

    ·50m
  10. 10

    High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It)

    ·53m
  11. 11

    48 and Worried About Early Retirement? This Changes the Math

    ·43m
  12. 12

    Social Security Timing and When Family Wrecks Retirement

    ·43m
  13. 13

    How to Beat the "Fire Hydrant" of Future Taxes: YMYW Best of 2025

    ·1h 3m
  14. 14

    I'm 42 and Burned Out with $2.25M. Can I Retire Early from My Toxic Job?

    ·38m
  15. 15

    Retirement Finances Whether You're Married, Separated, or Single

    ·54m
  16. 16

    The Truth About High Income Investments and Retirement Safety

    ·37m
  17. 17

    Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings?

    ·52m
  18. 18

    UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused

    ·41m
  19. 19

    Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap?

    ·31m
  20. 20

    Retiring Before Social Security? Consider These Portfolio Changes

    ·41m
  21. 21

    Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins?

    ·35m
  22. 22

    Should You Convert to Roth Before or After You Retire?

    ·41m
  23. 23

    Where Should You Take Retirement Money First If You've Saved $2M?

    ·50m
  24. 24

    What Retiring With $6 Million Really Looks Like

    ·36m
  25. 25

    Is Financial Software Giving You False Retirement Confidence?

    ·48m
  26. 26

    Roth Conversions: When to Make 'Em, When to Take 'Em

    ·43m
  27. 27

    What The New Law Means For Your Roth IRA!

    ·38m
  28. 28

    What's the Tax Triangle and How to Find Out if Yours is Lopsided

    ·29m
  29. 29

    Can You Retire at Age 57 and Spend Big?

    ·39m
  30. 30

    Are You Cutting Retirement Too Close?

    ·36m
  31. 31

    Are These Millennials Saving Enough to Retire Before 60?

    ·49m
  32. 32

    Smart Strategies to Retire Early and Spend More

    ·33m
  33. 33

    How Much Money Do You Need to Retire ASAP?

    ·50m
  34. 34

    Alternative Investments, Annuities, and Real Estate Syndications

    ·48m
  35. 35

    Can You Retire? Here's How to Calculate How Much You Need

    ·51m
  36. 36

    Good Tax Planning Can Save You HOW Much?! Find Out From IRA Guru Ed Slott, CPA

    ·49m
  37. 37

    Market Timing Retirement Withdrawals and Roth Conversions

    ·49m
  38. 38

    Should Siblings Take Out Life Insurance on Parents Before Inheriting $10M?

    ·52m
  39. 39

    Retirement Planning With a Large Age Difference: A Case Study | YMYW Extra - 6

    ·42m
  40. 40

    Spousal Social Security, Retirement Expenses and Roth Conversions | YMYW Extra - 4

    ·15m
  41. 41

    Spitballing Retirement During the Expensive Kid Years

    ·34m
  42. 42

    Roth Conversions vs. Required Minimum Distributions

    ·38m
  43. 43

    Asset Location & Roth Conversion Retirement Spitball | YMYW Extra - 1

    ·31m
  44. 44

    Slopes Vs. Suits: How Couples Bridge the Retirement Gap

    ·39m
  45. 45

    FDIC vs. SIPC, Annuities, SSDI & Early Retirement Strategies

    ·44m
  46. 46

    Will Buying Your Dream Home Ruin Early Retirement?

    ·48m
  47. 47

    Exchange Funds Explained, Roth Conversion Timing

    ·47m
  48. 48

    Spitballing Retirement From Apple to a Tax-Friendly State | YMYW Extra - 5

    ·16m
  49. 49

    Don't Let Money Anxiety Ruin Your Retirement

    ·37m
  50. 50

    What's a Safe Withdrawal Rate in Retirement? (So You Won't Run Out of Money)

    This episode discusses safe withdrawal rates in retirement planning, addressing listener questions about financial phases, Social Security strategies, and tax implications.

    ·46m
  51. 51

    How to Accomplish Your Retirement Goals - Even Without a Fat Wallet

    Joe and Big Al discuss retirement strategies for people with modest savings, addressing specific listener cases and their financial goals.

    ·51m
  52. 52

    How to Reduce the Widow's Tax Penalty

    ·36m
  53. 53

    Happily Ever After in Retirement? | YMYW Extra - 3

    ·18m
  54. 54

    0% Capital Gains Tax vs. Roth Conversion vs.... a Cruise?

    Joe Anderson and Big Al Clopine answer listener questions on retirement strategies in episode 517 of Your Money, Your Wealth.

    ·38m·3 clips
  55. 55

    Where to Invest for Pre-Retirement and a GO-GO Lifestyle?

    ·27m
  56. 56

    When Roth Conversions Don't Make Sense (And When They're a No-Brainer)

    Hosts Joe Anderson and Big Al Clopine analyze listener questions about Roth conversions for retirement planning.

    ·43m·4 clips
  57. 57

    Financial Planning for Marriage, Separation, and Singlehood

    ·52m
  58. 58

    Die With Zero: Are You Giving Your Kids Too Much?

    ·44m
  59. 59

    Early Withdrawals, Tech Stocks vs. International, Annuities, ESOP and NUA

    ·34m
  60. 60

    How to Pay Less Tax and Invest for Retirement

    ·46m
  61. 61

    Is Your Roth Conversion Timing All Wrong? (Financial Blunders)

    ·49m
  62. 62

    Asset Location, Investing Property Sale Proceeds, and Maxing Tax-Free Retirement

    ·36m
  63. 63

    Social Security vs. Pension No More

    ·17m
  64. 64

    When Do Roth Conversions STOP Making Sense?

    ·27m
  65. 65

    Roth Conversions vs. IRMAA, Using Retirement Funds to Pay the Mortgage, Retirement Spending Plan

    ·28m
  66. 66

    "The Payoff is Huge": Jonathan Clements' Final Initiative to Empower Lifelong Savers

    ·20m
  67. 67

    Tariffs Killed My Portfolio. Should I Claim Social Security Early?

    ·26m
  68. 68

    Portfolio Drift, Avoiding Capital Gains, and a $6M Retirement

    ·37m
  69. 69

    When to HOLD OFF on Doing Roth Conversions

    ·37m
  70. 70

    Retirement Savings: When to Take Your Foot Off the Gas

    ·34m
  71. 71

    Taxable Income, Dividends, Roth & SMA: What's Missing in Your Early Retirement?

    ·42m
  72. 72

    Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why?

    ·51m
  73. 73

    Risks Threaten Retirement. Rewire Your Plans

    ·55m
  74. 74

    Will the Tax Cuts and Jobs Act Be Extended?

    ·47m
  75. 75

    These Three Investments Make for a Happier Retirement

    ·43m
  76. 76

    Choosing Your Retirement Income Style and Top 5 Ways to Manage Market Volatility

    ·43m
  77. 77

    What's the Future of Social Security Under the New Administration?

    ·42m
  78. 78

    Haven't Yet Saved a Million. Can We Still Retire Early?

    ·50m
  79. 79

    Should You Switch Retirement Contributions to Roth?

    ·40m
  80. 80

    Mutual Funds vs. ETFs, Bonds to Bourbon

    ·33m
  81. 81

    Deferred Comp, Roth Strategies, Asset Protection (and Gold)

    ·31m
  82. 82

    I Work in a Toxic Office. Can I Retire Early?

    ·36m
  83. 83

    Choosing the Right Investments for You

    ·37m
  84. 84

    Grow Your Wealth Tax-Free & Retire Sooner: YMYW Best of 2024

    ·1h 2m
  85. 85

    Defusing a Future Tax Bomb With Roth Conversions

    ·33m
  86. 86

    When to Claim Social Security and the Truth About Annuities

    ·43m
  87. 87

    Bonds and Annuities, Social Security and Retirement Spending

    ·41m
  88. 88

    9 Answers to Boost Tax-Free Roth Retirement Income

    ·35m
  89. 89

    How to Plan for 35 Years of Retirement Spending With Smart Roth Conversions

    ·51m
  90. 90

    How to Retire ASAP - and Where to Save to Get There

    ·32m
  91. 91

    Rules for Inheritances and Making Roth Contributions for Others

    ·40m
  92. 92

    When to Pay Off Your Home, Retire, and Do Roth Conversions

    ·53m
  93. 93

    Spitballing Early Retirement for the One Percenters

    ·33m
  94. 94

    Top Funniest Moments From the Your Money, Your WealthPodcast, Vol. 2

    ·51m
  95. 95

    How to Get Into Real Estate Investing, Spitballing Retirement

    ·34m
  96. 96

    Spend RMDs, or Reduce Distributions and Taxes With Roth Conversions?

    ·39m
  97. 97

    Tax-Savvy In-Plan Roth Conversions and Inherited IRA Withdrawals

    ·43m
  98. 98

    Age Plus 20 Rule for Retirement Contributions

    ·37m
  99. 99

    3 Strategies to Pay Roth Conversion Taxes

    ·34m
  100. 100

    How to Get Into the Stock Market: Dollar Cost Average or Go All In?

    ·43m
  101. 101

    Can You Retire Early? With $475K at 42, You Need a Gap Plan

    Sep 29, 2026·41m
  102. 102

    Retirement Withdrawal Strategy: Is $100K a Year at 63 Wrong?

    Sep 22, 2026·50m
  103. 103

    Retirement vs. House Down Payment: Are You Getting the Timing Wrong?

    Sep 15, 2026·37m
  104. 104

    Can You Retire with $1M at 42? The Early Retirement Lie

    Sep 8, 2026·40m
  105. 105

    We Have $12 Million. Should We Do Roth Conversions?

    Sep 1, 2026·41m
  106. 106

    4 Retirement Questions That Expose Real Money Risks

    Aug 25, 2026·44m
  107. 107

    When to Claim Social Security and Why Full Roth Conversion Might be a Mistake

    Aug 18, 2026·47m
  108. 108

    He Has $10M and Can't Spend It. Here's Why.

    Aug 11, 2026·45m
  109. 109

    Roth vs. Traditional 401(k) at $275K Income: What's the Right Move?

    Aug 4, 2026·46m
  110. 110

    We Reverse-Engineered Their $6.5M Retirement. Here's What We Found

    Jul 28, 2026·45m
  111. 111

    Roth Conversions and RMDs: Are You Ready to Retire?

    Hidden gem

    Your Money, Your Wealth episode 591 examines Roth conversions and retirement timing through cases involving B and S in Maryland, V in Oregon, and Chandler and Monica in Texas.

    Jul 21, 2026·34m·2 clips
  112. 112

    Got a Pre-Tax Fortune? Nobody Warns You About the Retirement Tax Bomb

    Jul 14, 2026·45m
  113. 113

    Retirement Margin Loans: Is Buy, Borrow, Die Worth the Risk?

    Jul 7, 2026·44m
  114. 114

    $500K Income, $900K Saved: Will FIRE at 55 Work?

    Jun 30, 2026·48m
  115. 115

    Roth Conversions vs. RMDs: Which Tax Bill Hurts More? - 587

    Jun 23, 2026·44m
  116. 116

    Roth Conversions: When to Pay Taxes NOW

    Jun 16, 2026·44m
  117. 117

    Don't Overcomplicate Retirement: Margin Loans, Whole Life, Roth Mistakes

    Jun 8, 2026·43m
  118. 118

    These Tax Strategies Let You Spend More in Retirement

    Jun 2, 2026·47m
  119. 119

    $1.6M in One Stock? Here's How to Get Out Without Getting Crushed

    May 26, 2026·47m
  120. 120

    Safe Withdrawal Rate Debate: How Much Can You REALLY Spend in Early Retirement?

    May 19, 2026·43m
  121. 121

    Roth Conversions, Pension Lump Sums & Annuities: Is Bigger Always Better?

    May 12, 2026·38m
  122. 122

    You Have Enough to Retire Before 60. Why Are You Still Working?

    May 5, 2026·46m
  123. 123

    Too Much 401k Money? The $3M Roth Conversion Problem

    Apr 28, 2026·46m
  124. 124

    The Retirement Question Every Couple Asks: Can We Afford It?

    Apr 21, 2026·44m
  125. 125

    This Early Retirement Strategy Could Be a Huge Mistake

    This episode discusses the potential pitfalls of using the 72T tax election for early retirement, featuring listener questions about withdrawal strategies, asset allocation, and financial planning for layoffs.

    Apr 14, 2026·45m
  126. 126

    When Roth Conversions Don't Make Sense (And When They're a No-Brainer)

    This episode discusses the pros and cons of Roth conversions for various listener scenarios, including those with high capital gains, nearing retirement, or aggressive strategies.

    Apr 7, 2026·43m
  127. 127

    Die With Zero: Are You Giving Your Kids Too Much?

    This episode discusses retirement planning strategies, including the Die With Zero philosophy, with callers seeking advice on balancing personal retirement goals with financially supporting their children.

    Mar 31, 2026·44m
  128. 128

    When Should You Take Social Security? (Don't Screw This Up)

    This episode analyzes Social Security claiming strategies for different retirement scenarios, featuring listener questions about timing benefits with financial situations.

    Mar 24, 2026·45m
  129. 129

    Could You Retire Tomorrow If You Had To?

    This episode analyzes multiple retirement scenarios including a 68-year-old single man with $1.6 million saved who has never budgeted, exploring how much he can actually spend in retirement.

    Mar 17, 2026·40m
  130. 130

    Could You Lose Half Your Retirement Income to Taxes?

    Tyrone is looking at $2.2 million before taxes.

    Mar 10, 2026·51m·3 clips
  131. 131

    Retire Early in Your 40s or 50s: Green Light or Reality Check?

    Julie Anderson CFP and Big Al Clopine tackle five early-retirement plans.

    Mar 3, 2026·45m·3 clips
  132. 132

    Retirement Planning for Aging Parents - and Can You Retire Early?

    Joe Anderson and Big Al Clopine work through several retirement questions with real-life pressure behind them.

    Feb 24, 2026·46m·4 clips
  133. 133

    Retirement Changes at These 5 Major Financial Crossroads

    Hidden gem

    ["Your Money, Your Wealth episode 569 follows five retirement crossroads, from a 42-year-old Illinois business owner with a $14 million offer to a 65-year-old couple choosing Roth versus traditional contributions.", "Fine and Dandy describes about $4 million in taxable brokerage, about $4 million in tax-deferred accounts, a $550,000 rental, a $500,000 condo with a $180,000 mortgage, and a planned $2.5 million vacation home.", "Joey Anderson, CFP, and Big Al Clopine, CPA, say a 36% current tax bracket usually favors pre-tax contributions, while January-versus-December RMD timing is mainly a cash-flow and market-growth choice.", "Brian in Albany, New York and David in Logan, New Mexico push the episode toward retirement logistics, asking how much cash to hold and how to simplify finances before cognitive decline or assisted living."]

    Feb 17, 2026·44m·4 clips
  134. 134

    Tax-Smart Investing at Every Age: Starting Young or Catching Up

    Feb 10, 2026·44m
  135. 135

    Rising Costs and Retirement Unknowns? Here's What to Do - 567

    Feb 3, 2026·50m
  136. 136

    High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It)

    Jan 27, 2026·53m
  137. 137

    48 and Worried About Early Retirement? This Changes the Math

    Jan 20, 2026·43m
  138. 138

    Social Security Timing and When Family Wrecks Retirement

    Jan 13, 2026·43m
  139. 139

    How to Beat the "Fire Hydrant" of Future Taxes: YMYW Best of 2025

    Jan 6, 2026·1h 3m
  140. 140

    I'm 42 and Burned Out with $2.25M. Can I Retire Early from My Toxic Job?

    Dec 30, 2025·38m
  141. 141

    Retirement Finances Whether You're Married, Separated, or Single

    Dec 23, 2025·54m
  142. 142

    The Truth About High Income Investments and Retirement Safety

    Dec 16, 2025·37m
  143. 143

    Will Buying Your Dream Home Ruin Early Retirement?

    Dec 9, 2025·48m
  144. 144

    Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings?

    Dec 2, 2025·52m
  145. 145

    UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused

    Nov 25, 2025·41m
  146. 146

    Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap?

    Nov 18, 2025·31m
  147. 147

    Retiring Before Social Security? Consider These Portfolio Changes

    Nov 11, 2025·41m
  148. 148

    Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins?

    Nov 4, 2025·35m
  149. 149

    Should You Convert to Roth Before or After You Retire?

    Oct 28, 2025·41m
  150. 150

    Don't Let Money Anxiety Ruin Your Retirement

    Oct 21, 2025·37m
  151. 151

    Where Should You Take Retirement Money First If You've Saved $2M?

    Oct 14, 2025·50m
  152. 152

    Is Your Roth Conversion Timing All Wrong? (Financial Blunders)

    Oct 7, 2025·49m
  153. 153

    What Retiring With $6 Million Really Looks Like

    Sep 30, 2025·36m
  154. 154

    Is Financial Software Giving You False Retirement Confidence?

    Sep 23, 2025·48m
  155. 155

    Roth Conversions: When to Make 'Em, When to Take 'Em

    Sep 16, 2025·43m
  156. 156

    How to Accomplish Your Retirement Goals - Even Without a Fat Wallet

    Sep 9, 2025·51m
  157. 157

    What The New Law Means For Your Roth IRA!

    Sep 2, 2025·38m
  158. 158

    What's the Tax Triangle and How to Find Out if Yours is Lopsided

    Aug 26, 2025·29m
  159. 159

    Can You Retire at Age 57 and Spend Big?

    Aug 19, 2025·39m
  160. 160

    Are You Cutting Retirement Too Close?

    Aug 12, 2025·36m
  161. 161

    Are These Millennials Saving Enough to Retire Before 60?

    Aug 5, 2025·49m
  162. 162

    Smart Strategies to Retire Early and Spend More

    Jul 29, 2025·33m
  163. 163

    Where to Invest for Pre-Retirement and a GO-GO Lifestyle?

    Jul 22, 2025·27m
  164. 164

    How Much Money Do You Need to Retire in 2026?

    Jul 15, 2025·35m
  165. 165

    Asset Location, Investing Property Sale Proceeds, and Maxing Tax-Free Retirement

    Jul 8, 2025·36m
  166. 166

    Social Security vs. Pension No More

    Jul 1, 2025·17m
  167. 167

    When Do Roth Conversions STOP Making Sense?

    Jun 24, 2025·27m
  168. 168

    Roth Conversions vs. IRMAA, Using Retirement Funds to Pay the Mortgage, Retirement Spending Plan

    This episode addresses three listener questions about retirement planning, focusing on Roth conversions versus IRMAA considerations, using retirement funds to pay off a mortgage, and optimizing withdrawal strategies from different accounts.

    Jun 17, 2025·28m
  169. 169

    Early Withdrawals, Tech Stocks vs. International, Annuities, ESOP and NUA

    This episode addresses listener questions on retirement strategies including 72T early withdrawals, tech stock portfolios, annuities, and ESOP/NUA explanations.

    Jun 10, 2025·34m
  170. 170

    "The Payoff is Huge": Jonathan Clements' Final Initiative to Empower Lifelong Savers

    Jun 3, 2025·20m
  171. 171

    Tariffs Killed My Portfolio. Should I Claim Social Security Early?

    May 27, 2025·26m
  172. 172

    Portfolio Drift, Avoiding Capital Gains, and a $6M Retirement

    May 20, 2025·37m
  173. 173

    When to HOLD OFF on Doing Roth Conversions

    May 13, 2025·37m
  174. 174

    Retirement Savings: When to Take Your Foot Off the Gas

    May 6, 2025·34m
  175. 175

    Taxable Income, Dividends, Roth & SMA: What's Missing in Your Early Retirement?

    Apr 29, 2025·42m
  176. 176

    Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why?

    Apr 22, 2025·51m
  177. 177

    Risks Threaten Retirement. Rewire Your Plans

    Apr 15, 2025·55m
  178. 178

    Will the Tax Cuts and Jobs Act Be Extended?

    Apr 8, 2025·47m
  179. 179

    These Three Investments Make for a Happier Retirement

    Apr 1, 2025·43m
  180. 180

    Choosing Your Retirement Income Style and Top 5 Ways to Manage Market Volatility

    Mar 25, 2025·43m
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  183. 183

    What's a Safe Withdrawal Rate in Retirement? (So You Won't Run Out of Money)

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    Should You Switch Retirement Contributions to Roth?

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  185. 185

    0% Capital Gains Tax vs. Roth Conversion vs.... a Cruise?

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  186. 186

    Mutual Funds vs. ETFs, Bonds to Bourbon

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  187. 187

    Financial Planning for Marriage, Separation, and Singlehood

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  188. 188

    Deferred Comp, Roth Strategies, Asset Protection (and Gold)

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  189. 189

    I Work in a Toxic Office. Can I Retire Early?

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  190. 190

    Choosing the Right Investments for You

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  191. 191

    Grow Your Wealth Tax-Free & Retire Sooner: YMYW Best of 2024

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  192. 192

    Defusing a Future Tax Bomb With Roth Conversions

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  193. 193

    When to Claim Social Security and the Truth About Annuities

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  194. 194

    Bonds and Annuities, Social Security and Retirement Spending

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  195. 195

    9 Answers to Boost Tax-Free Roth Retirement Income

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  196. 196

    How to Plan for 35 Years of Retirement Spending With Smart Roth Conversions

    Dec 3, 2024·51m
  197. 197

    How to Retire ASAP - and Where to Save to Get There

    Nov 26, 2024·32m
  198. 198

    Rules for Inheritances and Making Roth Contributions for Others

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  199. 199

    When to Pay Off Your Home, Retire, and Do Roth Conversions

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  200. 200

    Spitballing Early Retirement for the One Percenters

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  201. 201

    How to Reduce the Widow's Tax Penalty

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  202. 202

    Top Funniest Moments From the Your Money, Your WealthPodcast, Vol. 2

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  203. 203

    How to Get Into Real Estate Investing, Spitballing Retirement

    Oct 15, 2024·34m
  204. 204

    Spend RMDs, or Reduce Distributions and Taxes With Roth Conversions?

    Oct 8, 2024·39m
  205. 205

    Tax-Savvy In-Plan Roth Conversions and Inherited IRA Withdrawals

    Oct 1, 2024·43m
  206. 206

    Age Plus 20 Rule for Retirement Contributions

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  207. 207

    3 Strategies to Pay Roth Conversion Taxes

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  208. 208

    How to Get Into the Stock Market: Dollar Cost Average or Go All In?

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  209. 209

    How Much Money Do You Need to Retire ASAP?

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  210. 210

    Exchange Funds Explained, Roth Conversion Timing

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  211. 211

    Alternative Investments, Annuities, and Real Estate Syndications

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  212. 212

    Can You Retire? Here's How to Calculate How Much You Need

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  213. 213

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  214. 214

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  215. 215

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  216. 216

    How to Pay Less Tax and Invest for Retirement

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  217. 217

    Retirement Planning With a Large Age Difference: A Case Study | YMYW Extra - 6

    Jul 9, 2024·42m
  218. 218

    Spitballing Retirement From Apple to a Tax-Friendly State | YMYW Extra - 5

    Jul 2, 2024·16m
  219. 219

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  220. 220

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  221. 221

    Spitballing Retirement During the Expensive Kid Years

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  222. 222

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  223. 223

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  224. 224

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  225. 225

    FDIC vs. SIPC, Annuities, SSDI & Early Retirement Strategies

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  226. 226

    Which Account Should Fund Living Expenses in Retirement?

    May 14, 2024·44m
  227. 227

    401(k) vs. Roth: Where to Save for Retirement

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  228. 228

    Tax Loss Harvesting, Tax Gain Harvesting, Financial Advisor Value

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  229. 229

    How to Manage Taxes When You Win the Lottery

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  230. 230

    What's the Break-Even Point on Roth Conversions?

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  231. 231

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    Apr 9, 2024·50m
  232. 232

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  233. 233

    How to Take the Uncertainty of Taxes Off the Table

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  234. 234

    Does Your Financial Advisor Just Want to Collect Fees?

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  235. 235

    Will Roth Conversions Put You On Track to Retire Early?

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  236. 236

    How Much Should You Convert to Roth IRA?

    Mar 5, 2024·54m
  237. 237

    Spitballing Retirement for Fat Wallets

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  238. 238

    401(k) Ins & Outs, Roth Conversion Benefits, and Divorce Finances

    Feb 20, 2024·51m
  239. 239

    How Much to Save in Tax-Free, Tax-Deferred, and Taxable Accounts?

    Feb 13, 2024·46m
  240. 240

    What Does Retirement Look Like for You?

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  241. 241

    Roth Conversions to Pay Less Tax on Retirement Withdrawals

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  242. 242

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  243. 243

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  244. 244

    Retirement Investing, Roth Conversion Pros & Cons: YMYW Best of 2023

    Jan 9, 2024·1h 11m
  245. 245

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  246. 246

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  247. 247

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  248. 248

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    Dec 12, 2023·52m
  249. 249

    Retirement Spending and Timing Your Mortgage Payoff

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  250. 250

    How to Cut Your Taxes Before Year-End

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  251. 251

    How to Bridge the Gap to Retirement Income: Pension Spitball

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  252. 252

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  253. 253

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  254. 254

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  255. 255

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  256. 256

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  257. 257

    Retirement Withdrawals: What's a Safe Distribution Rate?

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  258. 258

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    Oct 3, 2023·45m
  259. 259

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    Sep 26, 2023·47m
  260. 260

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  261. 261

    DIY Early Retirement Planning

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  262. 262

    Market Timing, Pension, & Roth Conversion Retirement Spitball

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  263. 263

    What Are the Rules for Taking Money From a Roth IRA?

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  264. 264

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  265. 265

    RSU, Mutual Funds, Bonds, and Annuities

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  266. 266

    Early Retirement Withdrawals & Capital Gains Tax Explained

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  267. 267

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  268. 268

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  269. 269

    When Will You Be Able to Retire?

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  270. 270

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  271. 271

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  272. 272

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  273. 273

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  274. 274

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  275. 275

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  276. 276

    How to Calculate Your Retirement Needs in Future Dollars

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  277. 277

    How to Consider Your Pension Options for Retirement

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  278. 278

    HSA to Roth, RMD Investing, and Social Security Strategies

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  279. 279

    What to Do With Inheritance Money?

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  280. 280

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  281. 281

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  282. 282

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  283. 283

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  284. 284

    What to Do When There's Too Much Money in Your Traditional IRA

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  285. 285

    How to Reduce Taxes and Get Better Investing Returns? Asset Location

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  286. 286

    Roth Conversions & Retirement Spitball Analysis

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  287. 287

    Mutual Funds vs. ETFs, SECURE 2.0 & Capital Gains Strategies

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  288. 288

    How to Start Planning for Retirement

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  289. 289

    "Will I Ever Be Able to Retire?"

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  290. 290

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  291. 291

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  292. 292

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  293. 293

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  294. 294

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  295. 295

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  296. 296

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  298. 298

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  300. 300

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  301. 301

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  302. 302

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  303. 303

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  304. 304

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  305. 305

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  306. 306

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  307. 307

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  308. 308

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  309. 309

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  310. 310

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  311. 311

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  312. 312

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  313. 313

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  314. 314

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  315. 315

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  316. 316

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  317. 317

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  318. 318

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  319. 319

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    Aug 2, 2022·45m
  320. 320

    Pay Tax on This Move Now to Potentially Have More to Spend Later

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  321. 321

    A Model Retirement Plan Spitball Analysis

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  322. 322

    Should We Hold Off on Retiring Until the Markets Recover?

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  323. 323

    Bonds and Series I Bonds, High Inflation, and High Interest Rates

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  324. 324

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  325. 325

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  326. 326

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    Jun 14, 2022·36m
  327. 327

    Don't Retire Until You Can Answer These Five Practical Questions

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  328. 328

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  329. 329

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    May 24, 2022·49m
  330. 330

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    May 17, 2022·42m
  331. 331

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    May 10, 2022·45m
  332. 332

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  333. 333

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  334. 334

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  335. 335

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    Apr 12, 2022·38m
  336. 336

    Retirement Spitball: Social Security, Pension, and Self-Employed

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  337. 337

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    Mar 29, 2022·35m
  338. 338

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  339. 339

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  340. 340

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  341. 341

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  342. 342

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  343. 343

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  344. 344

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  345. 345

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  346. 346

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  347. 347

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  348. 348

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    Jan 11, 2022·35m
  349. 349

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  350. 350

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  351. 351

    Does the 5 Year Rule Apply to Each Roth Conversion?

    Dec 21, 2021·46m
  352. 352

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  353. 353

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    Dec 7, 2021·33m
  354. 354

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    Nov 30, 2021·55m
  355. 355

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  356. 356

    Dividends, Asset Classes, and Diversification: How to Invest for Retirement?

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  357. 357

    Estate Planning, Social Security, and TSP to Roth Conversions

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  358. 358

    Spitballing the Sequence of Retirement Savings

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  359. 359

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  360. 360

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  361. 361

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    Oct 12, 2021·38m
  362. 362

    Buying and Selling Your House or Real Estate

    Oct 5, 2021·32m
  363. 363

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  364. 364

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    Sep 21, 2021·47m
  365. 365

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    Sep 14, 2021·39m
  366. 366

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  367. 367

    Early Retirement Spitball Analysis

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  368. 368

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    Aug 24, 2021·50m
  369. 369

    Should We Do a Roth Conversion?

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  370. 370

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    Aug 10, 2021·43m
  371. 371

    Is It Crazy to Be Happy Paying Tax on Massive Stock Market Gains?

    Aug 3, 2021·44m
  372. 372

    How to Spitball Your Most Tax-Efficient Retirement Withdrawal Strategy

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  373. 373

    Which States Are the Most Tax-Friendly in Retirement?

    Jul 20, 2021·46m
  374. 374

    Are We On Track for Retirement? Financial Plan Spitball Analysis

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  375. 375

    Are Financial Advisors Really Worth the Money?

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  376. 376

    Roth Conversions, Medicare, and Required Minimum Distributions

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  377. 377

    What is the Best Age to Retire, Financially Speaking?

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  378. 378

    Has the Government Ever Reduced Social Security Benefits?

    Jun 15, 2021·49m
  379. 379

    How to Protect Investments Against a Stock Market Crash?

    Jun 8, 2021·45m
  380. 380

    Should People in High Tax Brackets Save in Roth Retirement Accounts?

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  381. 381

    How to Avoid a Tax Time Bomb: Retirement Plan Spitball Analysis

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  382. 382

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  383. 383

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  384. 384

    Which Asset Classes Are Good Investments to Hedge Against Inflation?

    May 4, 2021·30m
  385. 385

    Real Estate: Should We Sell Rental Property to Buy a Primary Residence?

    Apr 27, 2021·33m
  386. 386

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    Apr 20, 2021·37m
  387. 387

    Inflation, Variable Annuities, Real Estate: How to Invest Against Risk

    Apr 13, 2021·38m
  388. 388

    Early Retirement: Can You Afford to Retire Now?

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  389. 389

    Roth IRA Excess Contributions and the Pro-Rata Rule

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  390. 390

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  391. 391

    Charitable Giving and Roth Conversion Retirement Tax Strategies

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  392. 392

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    Mar 9, 2021·50m
  393. 393

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    Mar 2, 2021·52m
  394. 394

    Is the Backdoor Roth IRA a Good Strategy For You?

    Feb 23, 2021·44m
  395. 395

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    Feb 17, 2021·59m
  396. 396

    "Super Roth": Should You Overfund Supplemental Executive Retirement Plan Insurance?

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  397. 397

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  398. 398

    [SPECIAL] Gamestop: Stocks Gone Wild! Should You Join the Day Trading Craze?

    Jan 30, 2021·17m
  399. 399

    What's the Best Way to Take Retirement Distributions?

    Jan 26, 2021·43m
  400. 400

    Retirement Plan Spitball Analyses for Side Hustles, Clergy & Grandkids

    Jan 19, 2021·50m
  401. 401

    How to Do the Mega Backdoor Roth IRA

    Jan 12, 2021·45m
  402. 402

    How to Choose Your Pension Options and Retirement Withdrawal Strategy

    Jan 5, 2021·49m
  403. 403

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    Dec 29, 2020·42m
  404. 404

    What's the Best Retirement Withdrawal Strategy?

    Dec 22, 2020·42m
  405. 405

    5 Last Minute Ways to Cut Your 2020 Taxes

    Dec 15, 2020·41m
  406. 406

    How to Use Tax Diversification in Your Retirement Portfolio

    Dec 8, 2020·43m
  407. 407

    Should You Pay Off the Mortgage? First Consider Your Tax Strategy

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  408. 408

    Borrow Money to Pay Tax on a Roth IRA Conversion?

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  409. 409

    Top Funniest Moments From the Your Money Your Wealth Podcast

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  410. 410

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  411. 411

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  412. 412

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  413. 413

    YMYW Spitball Analysis 3: Tax Diversification and Asset Allocation

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  414. 414

    All About the Backdoor Roth IRA Strategy

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  415. 415

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  416. 416

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  417. 417

    Will Estate Tax Law Changes Affect Your Family Financial Plan?

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  418. 418

    Roth Conversions, Annuities and Inherited IRAs

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  419. 419

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  420. 420

    Backdoor Roth IRA Conversions, Stimulus and Self-Employed Retirement

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  421. 421

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  422. 422

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  423. 423

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