Retirement Starts Today
Benjamin Brandt CFP®, RICP®
Do you want to spend more money in retirement, while paying less taxes? Great news, you're in the right place!
I'll also teach you the benefits of retiring TO something, while most retirees only solve half the equation by retiring FROM something. Tune in every Monday morning - hosted by Benjamin Brandt CFP, RICP.
Join my "Every Day is Saturday" weekly newsletter for show notes, free book giveaways and other great retirement content: www.retirementstartstodayradio.com/newsletter
I'll also teach you the benefits of retiring TO something, while most retirees only solve half the equation by retiring FROM something. Tune in every Monday morning - hosted by Benjamin Brandt CFP, RICP.
Join my "Every Day is Saturday" weekly newsletter for show notes, free book giveaways and other great retirement content: www.retirementstartstodayradio.com/newsletter
Episodes
Mentioned books
Mar 30, 2026 • 20min
Estimated Taxes Are a Pain. Let's make it Easier
They dig into rising estimated tax penalties and why retirees and investors are getting caught. Practical tactics for avoiding penalties like withholding, safe-harbor rules, and annualized income reporting are discussed. The conversation shifts to balancing growth and income in retirement portfolios and how to build a multi-year cash/bond runway. A listener story highlights active, optimistic retirement life.
9 snips
Mar 23, 2026 • 16min
The Hidden Cost Of Investment Income
They explore how interest and dividends can quietly reduce after-tax wealth for high-net-worth investors. The show contrasts forced income with tax-deferring appreciation and highlights step-up and charitable giving benefits. Tax timing, capital gains rules, and the flexibility of taxable brokerage accounts get a clear breakdown. A heartwarming story about puppy raising for the blind closes the conversation.
Mar 16, 2026 • 22min
The Medicare Charge That's Taking a Bigger Bite Out of Social Security Checks
They unpack how rising Medicare premiums and IRMAA surcharges can eat into Social Security COLA increases. They explain IRMAA brackets, projected premium hikes, and why top tiers may rise faster than benefits. Practical moves to manage MAGI and avoid costly income cliffs are covered. They also discuss persuading older relatives to spend more and a story about finding purpose teaching tango in retirement.
6 snips
Mar 9, 2026 • 22min
Tax Return Red Flags
They treat tax returns as diagnostic tools and flag four common signs of missed proactive tax planning. Topics include very low taxable income, charitable giving strategies like QCDs and gifting appreciated securities, and when municipal bonds may not be optimal. They also discuss a practical cash-burn calculation to evaluate scaling back work and share an inspiring retire-to-something story.
5 snips
Mar 2, 2026 • 18min
Stop Chickening Out
A provocative take on why retirees over-layer safety around withdrawal rules and should stop chasing impossible certainty. A breakdown of why safe withdrawal rates are conservative by design and how psychology drives doom stacking. A practical debate about using Traditional IRA withdrawals versus Roth conversions. A feel-good listener story about finding purpose after retirement.
Feb 23, 2026 • 23min
8 Tips to Stop Worrying About Running Out of Money in Retirement
Concrete anchors to replace constant fear with practical retirement moves. Tips on confirming a sustainable spending range and staying flexible during market downturns. Ideas for building a recession buffer, reducing tax uncertainty, and maximizing guaranteed income. Strategies for protecting against long-term care costs and using home equity as a backstop. A discussion on why distribution risks differ from accumulation.
Feb 16, 2026 • 22min
The Best Way to Leave Money Behind
Research-backed withdrawal plans that aim to leave more money behind are explored and compared. Trade-offs between spending now and maximizing bequests are discussed. Practical differences among 401(k), 403(b), and 457 rules are explained. Advice on account consolidation, Roth conversions, and giving smaller gifts earlier rounds out the conversation.
14 snips
Feb 9, 2026 • 18min
The Ideal Level of Wealth
A math-based take on how much money is enough and practical wealth targets using withdrawal rules. A closer look at treating Social Security and pensions when counting net worth. Clear comparisons of lump-sum versus annuity pension choices and how to judge implied returns. A story about reinventing work in retirement and planning purpose early.
Feb 2, 2026 • 21min
Why are You Still Working?
A look at five motivating reasons people keep working as retirement nears, from necessity to unclear purpose. Discussion of using first principles thinking to define ideal days and test retirement plans. Practical talk on timing Required Minimum Distributions and when delaying the first RMD can help. Stories about finding purpose after work and steps to move toward a fulfilling retirement.
Jan 26, 2026 • 20min
Helping Underspenders And "Savers" Understand They CAN Spend More
They explore why lifelong savers often fear spending in retirement and how psychology, not math, drives undersaving behavior. Psychological barriers covered include fear of dependence, doom forecasting, and saver identity. A practical “experiments” method is offered to test low-stakes spending decisions. There is also a clear breakdown of Medicare Parts B and D enrollment rules and penalties.
