Retirement Planning Education, with Andy Panko

Listener Q&A tackles portfolio rebalancing cadence, when to check big-picture finances, and ways to handle highly appreciated stock positions. Practical rules for keeping or rolling old 401(k) plans, tracking Roth contributions and inherited Roth rollovers. Discussion of RMD impact, using pre-tax money to pay a mortgage, mutual-fund-to-ETF conversions, and rental property versus CDs for legacy planning.

Jim Kellerman, a retiree and former patent attorney from Cincinnati who now teaches and volunteers in prisons while doing part-time estate planning. He talks about shifting from full-time law to purposeful encore work. He describes daily life, health insurance before Medicare, deferred compensation and Roth conversion thinking. He stresses phased retirement, structure, and the value of disciplined saving.

Bradley Hilton, CFP and founder of Sonas Financial Planning in Atlanta, offers flat‑fee retirement and pre‑retirement planning. He discusses overlooked retirement blind spots, healthcare and long‑term care cost risks, tax‑aware distribution strategies, annuities and insurance tradeoffs, investment philosophy, wellness (purpose, passion, people), and how to pick and price the right advisor.

Clear breakdown of what legally counts as a gift and common examples like cash, property, and securities. How basis transfers work when you give appreciated assets. Rules around the federal lifetime exemption, annual gift exclusion amounts, and when Form 709 must be filed. Tactics for maximizing exclusions, spousal splitting, community property nuances, and why keeping Form 709 records matters.

A rapid-fire Q&A covering bond accrued interest and 1099 adjustments. Discussion of Roth catch-up versus taxable brokerage saving. Clarifies taxation timing for retroactive Social Security lump sums. Debates paying off a mortgage now versus investing. Explains step-up in basis differences by state and how to gift without triggering a return. Looks at direct indexing and tax-smart charitable timing.

Kevin Sebesta, an early retiree and Rock Retirement Club coach who left work at 43 and blogs at LifeInFIRE.com. He talks about starting the FIRE journey, living well on one income without major sacrifices, health insurance and long-term care planning after early retirement, the role of community in sustaining FIRE, and practical tactics like Roth conversions and flexible spending.

Jason Cutitta, retirement planner and principal of ToBa Financial who hosts the Hawaii Retirement Show, joins to tackle timely retirement puzzles. They discuss treating potential inheritances, limits of the Die With Zero idea, new in-plan Roth conversions for TSP, strategies for which accounts to tap first with age gaps, RMD timing, tax filing reasons, and when to hire an advisor.

A deep dive into how after-tax IRA contributions are converted into Roth accounts and the two-step mechanics involved. Clear explanations of MAGI limits, contribution caps, and timing rules. A close look at the pro rata rule, year-end balances, and pitfalls when moving funds between IRAs and 401(k) plans.

He traces a long finance journey from sales and pensions to market risk, hedge fund analysis, and private credit research. He tells how researching Social Security for his mother triggered a shift toward fee-only, planning-focused advice. He explains launching an advisory firm, early marketing flops, and growing an engaged Facebook community that fueled his educational channels.

Listeners dive into the complexities of spousal Social Security benefits and the rules surrounding them. Andy demystifies how to view pre-tax retirement accounts after taxes and discusses naming minors as beneficiaries. He shares insights on cognitive biases in investing, highlighting the most prevalent ones he encounters. The episode also covers tips for changing state tax domicile and the implications of guaranteed income like Social Security on asset allocation. Lastly, he reexamines the 4% rule for retirement withdrawals.