All episodes

Is 4% Too Conservative? How Much You Can Really Spend in Retirement - 604

Is a $400K Roth Conversion at Peak Income a Mistake? - 603

Should You Do Roth Conversions in a Down Market? - 602

Can You Retire Early? With $475K at 42, You Need a Gap Plan - 601

Retirement Withdrawal Strategy: Is $100K a Year at 63 Wrong? - 600

Retirement vs. House Down Payment: Are You Getting the Timing Wrong? - 599

Can You Retire with $1M at 42? The Early Retirement Lie - 598

We Have $12 Million. Should We Do Roth Conversions? - 597

4 Retirement Questions That Expose Real Money Risks - 596

When to Claim Social Security and Why Full Roth Conversion Might be a Mistake - 595

He Has $10M and Can't Spend It. Here's Why. - 594

Roth vs. Traditional 401(k) at $275K Income: What's the Right Move? - 593

We Reverse-Engineered Their $6.5M Retirement. Here's What We Found - 592

Roth Conversions and RMDs: Are You Ready to Retire? - 591

Got a Pre-Tax Fortune? Nobody Warns You About the Retirement Tax Bomb - 590

Retirement Margin Loans: Is Buy, Borrow, Die Worth the Risk? - 589

$500K Income, $900K Saved: Will FIRE at 55 Work? - 588

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

Roth Conversions: When to Pay Taxes NOW - 586

Don't Overcomplicate Retirement: Margin Loans, Whole Life, Roth Mistakes - 585

These Tax Strategies Let You Spend More in Retirement - 584

$1.6M in One Stock? Here's How to Get Out Without Getting Crushed - 583

Safe Withdrawal Rate Debate: How Much Can You REALLY Spend in Early Retirement? - 582

Roth Conversions, Pension Lump Sums & Annuities: Is Bigger Always Better? - 581

You Have Enough to Retire Before 60. Why Are You Still Working? - 580

Too Much 401k Money? The $3M Roth Conversion Problem - 579

The Retirement Question Every Couple Asks: Can We Afford It? - 578

This Early Retirement Strategy Could Be a Huge Mistake - 577

When Roth Conversions Don't Make Sense (And When They're a No-Brainer) - 576

Die With Zero: Are You Giving Your Kids Too Much? - 575

When Should You Take Social Security? (Don't Screw This Up) - 574

Could You Retire Tomorrow If You Had To? - 573

Could You Lose Half Your Retirement Income to Taxes? - 572

Retire Early in Your 40s or 50s: Green Light or Reality Check? - 571

Retirement Planning for Aging Parents - and Can You Retire Early? - 570

Retirement Changes at These 5 Major Financial Crossroads - 569

Tax-Smart Investing at Every Age: Starting Young or Catching Up - 568

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

High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It) - 566

48 and Worried About Early Retirement? This Changes the Math - 565

Social Security Timing and When Family Wrecks Retirement - 564

How to Beat the "Fire Hydrant" of Future Taxes: YMYW Best of 2025 - 563

I'm 42 and Burned Out with $2.25M. Can I Retire Early from My Toxic Job? - 562

Retirement Finances Whether You're Married, Separated, or Single - 561

The Truth About High Income Investments and Retirement Safety - 560

Will Buying Your Dream Home Ruin Early Retirement? - 559

Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings? - 558

UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused - 557

Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap? - 556

Retiring Before Social Security? Consider These Portfolio Changes - 555

Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins? - 554

Should You Convert to Roth Before or After You Retire? - 553

Don't Let Money Anxiety Ruin Your Retirement - 552

Where Should You Take Retirement Money First If You've Saved $2M? - 551

Is Your Roth Conversion Timing All Wrong? (Financial Blunders) - 550

Can You Retire on $6 Million? Here's What It Looks Like - 549

Is Financial Software Giving You False Retirement Confidence? - 548

Roth Conversions: When to Make 'Em, When to Take 'Em - 547

How to Accomplish Your Retirement Goals - Even Without a Fat Wallet - 546

Your Roth Conversion Strategy Needs This Update - 545

Your Retirement Tax Strategy is Probably Unbalanced - 544

Can You Retire at Age 57 and Spend Big? - 543

Are You Cutting Retirement Too Close? - 542

Are These Millennials Saving Enough to Retire Before 60? - 541

Retire Early and Spend More Without Running Out of Money - 540

Where to Invest for Pre-Retirement and a GO-GO Lifestyle? - 539

How Much Money Do You Need to Retire in 2026? - 538

Late Start on Roth Savings? Here's What to Prioritize - 537

Social Security Rules Changed: Your Pension Doesn't Matter Anymore - 536

When Do Roth Conversions STOP Making Sense? - 535

Roth Conversions vs. IRMAA, Using Retirement Funds to Pay the Mortgage, Retirement Spending Plan - 534

Early Withdrawals, Tech Stocks vs. International, Annuities, ESOP and NUA - 533

"The Payoff is Huge": Jonathan Clements' Final Initiative to Empower Lifelong Savers - 532

Tariffs Killed My Portfolio. Should I Claim Social Security Early? - 531

Portfolio Drift, Avoiding Capital Gains, and a $6M Retirement - 530

When to HOLD OFF on Doing Roth Conversions - 529

Retirement Savings: When to Take Your Foot Off the Gas - 528

Taxable Income, Dividends, Roth & SMA: What's Missing in Your Early Retirement? - 527

Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why? - 526

Risks Threaten Retirement. Rewire Your Plans - 525

Will the Tax Cuts and Jobs Act Be Extended? - 524

These Three Investments Make for a Happier Retirement - 523

Choosing Your Retirement Income Style and Top 5 Ways to Manage Market Volatility - 522

What's the Future of Social Security Under the New Administration? - 521

Haven't Yet Saved a Million. Can We Still Retire Early? - 520

What's a Safe Withdrawal Rate in Retirement? (So You Won't Run Out of Money) - 519

Should You Switch Retirement Contributions to Roth? - 518

0% Capital Gains Tax vs. Roth Conversion vs.... a Cruise? - 517

Mutual Funds vs. ETFs, Bonds to Bourbon - 516

Financial Planning for Marriage, Separation, and Singlehood - 515

Deferred Comp, Roth Strategies, Asset Protection (and Gold) - 514

I Work in a Toxic Office. Can I Retire Early? - 513

Choosing the Right Investments for You - 512

Grow Your Wealth Tax-Free & Retire Sooner: YMYW Best of 2024 - 511

Defusing a Future Tax Bomb With Roth Conversions - 510

When to Claim Social Security and the Truth About Annuities - 509

Bonds and Annuities, Social Security and Retirement Spending - 508

9 Answers to Boost Tax-Free Roth Retirement Income - 507

How to Plan for 35 Years of Retirement Spending With Smart Roth Conversions - 506

How to Retire ASAP - and Where to Save to Get There - 505