Medicaid Myths, IRMAA, & Proper Long-Term Care Preparedness (5/9/2026)

The Retirement Calculator Problem (Plus RSUs, Stock Options & Company Stock Tax Surprises) (5/30/2026)

Can you really know if you're ready to retire? Jeremiah and Alex spend much of this episode unpacking one of the most commonly misunderstood tools in financial planning: retirement projections and Monte Carlo simulations. They explain what an 85% or 90% probability of success actually means, why those numbers can be useful, and where they can create a false sense of certainty if they're viewed in isolation. They explores sequence-of-return risk, retirement spending assumptions, inheritance surprises, and the reality that successful retirement planning requires far more than simply hitting a target number. Later in the show, Jeremiah and Alex tackle another area where people often misunderstand the rules: company stock compensation. They break down how RSUs, stock options, and employee stock purchase plans work, why taxes can catch employees off guard, and the planning opportunities available when company stock becomes a meaningful part of your net worth. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com [https://www.therealmoneypros.com] Hosts: Jeremiah Bates & Alex Lundgren ————— Ataraxis PEO https://ataraxispeo.com [https://ataraxispeo.com] Tree City Advisors of Apollon: https://www.treecityadvisors.com [https://www.treecityadvisors.com/] Apollon Wealth Management: https://apollonwealthmanagement.com/ [https://apollonwealthmanagement.com/] —————————————————————

When the Paycheck Stops, Then What?

For decades, most people focus on one side of retirement planning: Saving money, building investments, and growing retirement accounts. But eventually the question changes: "How do I actually live off this?" Nic talks about one of the biggest and most overlooked transitions in retirement: replacing a paycheck with income created from your own portfolio. From dividend-paying investments and automated distributions to cash reserves, taxes, Roth flexibility, and income coordination, Nic explains what retirement income actually looks like in the real world and why it's often much more complex than simply "living off dividends." He also dives into the emotional side of retirement income planning, including why so many people struggle with touching principal, spending from their own assets, and maintaining confidence once the steady paycheck disappears. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com [https://www.therealmoneypros.com/] ————————————————————— Ataraxis PEO https://ataraxispeo.com [https://ataraxispeo.com] Tree City Advisors of Apollon: https://www.treecityadvisors.com [https://www.treecityadvisors.com] Apollon Wealth Management: https://apollonwealthmanagement.com/ [https://apollonwealthmanagement.com/] —————————————————————

AI Scams, 401(k) Tax Mistakes, & Expensive Financial Missteps to Avoid (5/16/2026)

Financial problems don't always come from bad decisions—they often come from not understanding the rules. Jeremiah Bates and Nic Daniels break down the costly financial mistakes people make when acting without a clear strategy. The conversation starts with the growing threat of AI scams, wire fraud, romance scams, and why even younger, financially savvy individuals are getting caught off guard. From there, the show moves into retirement planning mistakes—how improper 401(k) rollovers can trigger unnecessary taxes and penalties, why understanding account rules matters, and when consolidating scattered retirement accounts makes sense. The hosts also tackle highly appreciated stock positions, Roth conversion strategy after age 65, Medicare premium impacts, Social Security coordination, and tax-efficient ways to unwind concentrated positions. The broader theme throughout the episode is simple: many of the most expensive financial mistakes are completely avoidable with proper planning… Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com [https://www.therealmoneypros.com] Hosts: Jeremiah Bates & Nic Daniels ————— Ataraxis PEO https://ataraxispeo.com [https://ataraxispeo.com] Tree City Advisors of Apollon: https://www.treecityadvisors.com [https://www.treecityadvisors.com/] Apollon Wealth Management: https://apollonwealthmanagement.com/ [https://apollonwealthmanagement.com/] —————————————————————

I'd Retire Tomorrow… If It Weren't for Health Insurance

"I'd retire tomorrow… if it weren't for health insurance." It's one of the most common concerns we hear from people approaching retirement, especially those hoping to leave work before Medicare begins at age 65. In this podcast, Nic Daniels breaks down the real planning considerations behind retiring before Medicare eligibility. From COBRA and Affordable Care Act marketplace plans to spouse coverage, bridge employment, and self-funding healthcare costs, Nic walks through the high-level options people should be aware of. But this conversation goes beyond just healthcare, because depending on how retirement income is structured, healthcare costs may be impacted by ACA subsidies, tax strategy, and withdrawal planning decisions. Nic also shares a real planning example involving a household looking to retire early and how outside assets—not retirement accounts—helped create flexibility in bridging the gap to Medicare. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com [https://www.therealmoneypros.com/] Hosts: Nic Daniels ————————————————————— Ataraxis PEO https://ataraxispeo.com [https://ataraxispeo.com] Tree City Advisors of Apollon: https://www.treecityadvisors.com [https://www.treecityadvisors.com] Apollon Wealth Management: https://apollonwealthmanagement.com/ [https://apollonwealthmanagement.com/] —————————————————————

Medicaid Myths, IRMAA, & Proper Long-Term Care Preparedness (5/9/2026)

Jeremiah Bates and Alex Lundgren spent Mother's Day weekend tackling one of the biggest financial issues many families avoid until it's too late: long-term care and the cost of aging. The show opens with Brooke Baker and Jessica Young, Co-Founders of Legacy Navigation, breaking down how Medicaid actually works, what it really covers, and the biggest misconceptions families have around qualifying for benefits. The conversation covers in-home care, assisted living, memory care costs, spousal asset protection strategies, the five-year lookback rule, and why certain estate planning decisions can accidentally create Medicaid problems later on. Going into the second hour, Jeremiah and Alex pivot into another major planning blind spot: letting taxes dictate investment decisions. They discuss concentrated stock positions, large unrealized gains, rental property sales, 1031 exchanges, Medicare IRMAA surcharges, and why many investors hold onto assets longer than they should simply because they fear the tax consequences. Throughout the show, the bigger theme remains the same: most financial problems become significantly harder when planning is delayed. Whether it's long-term care, estate coordination, taxes, or investment decisions, this show focuses on why proactive planning matters before life forces the issue. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com [https://www.therealmoneypros.com] Hosts: Jeremiah Bates & Alex Lundgren Guests:Brooke Baker, RN & Jessica Young, MSW Co-Founders of Legacy Navigation https://legacynavigate.com [https://legacynavigate.com/] ————————————————————— Ataraxis PEO https://ataraxispeo.com [https://ataraxispeo.com] Tree City Advisors of Apollon: https://www.treecityadvisors.com [https://www.treecityadvisors.com/] Apollon Wealth Management: https://apollonwealthmanagement.com/ [https://apollonwealthmanagement.com/] —————————————————————