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

Wealth Traps: Rental Properties, Concentrated Stock Positions & Retirement Income (6/20/2026)

Brian Wiley and Jeremiah Bates open the show with a discussion on concentrated stock positions, portfolio rebalancing, and the challenges investors face after large gains. Using examples ranging from Micron stock to broader market opportunities, they explore diversification, risk management, investor psychology, and the ongoing battle between fear and greed. The conversation also examines what it really means to be wealthy, how to think about financial independence, and why having a plan matters more than chasing the next investment opportunity. The second hour focuses on retirement income planning and highly appreciated assets, particularly rental properties. They discuss capital gains concerns, 1031 exchanges, Delaware Statutory Trusts (DSTs), step-up in basis rules, and strategies for investors who want to simplify their lives without creating unnecessary tax consequences. They also cover Treasury bills, retirement withdrawal planning, income-focused investing, and how to evaluate whether your assets are positioned to support your long-term goals. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com [https://www.therealmoneypros.com] Hosts: Jeremiah Bates & Brian Wiley ————— 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/] —————————————————————

Opportunity Zone Tax Deadlines, Smart RMD Strategies & SpaceX's Record IPO (6/13/2026)

SpaceX officially went public, raising a record $75 billion and becoming the largest IPO in history—and Jeremiah Bates and Nick Daniels spend the first hour breaking down what that means for investors, how IPOs work, whether buying newly public companies makes sense, and how many investors may gain exposure through index funds and retirement accounts. The conversation then shifts to a major tax planning issue approaching at the end of 2026: Qualified Opportunity Zone (QOZ) investments. The guys explain why deferred gains from these investments are becoming taxable, the planning opportunities available before the deadline, and what investors should be doing now to prepare. The show also covers donor-advised funds, highly appreciated stock strategies, the differences between flat-fee planning and traditional asset management, and practical retirement tax planning topics including required minimum distributions (RMDs), qualified charitable distributions (QCDs), Roth conversions, and Medicare-related planning opportunities. 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/] —————————————————————

Why Modern Estate Planning Looks Different

Estate planning used to be relatively straightforward: create a will, establish a trust if appropriate, and make sure your beneficiaries were named correctly. Today, it's much more complicated. We talk about how modern estate planning has evolved beyond traditional documents and why many families may have planning gaps they don't realize exist. Common reasons estate plans become outdated, the growing importance of digital assets, and the challenges families can face when trying to access online accounts, digital photos, cloud storage, payment apps, and other assets that didn't exist when many estate plans were originally created. We also discuss the difference between legal authority and practical access, why estate planning should be reviewed periodically, and simple steps families can take to reduce confusion and stress for loved ones. 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/] —————————————————————

SpaceX's IPO, Estate Planning Without Kids & Tax Gain Harvesting Strategies (6/6/2026)

What happens to your money, your assets, and even your digital life if you don't have children to step in? Jeremiah Bates and Alex Lundgren spend the first hour tackling one of the fastest-growing estate planning challenges in America: planning for incapacity and inheritance when there are no children or obvious heirs. The discussion covers power of attorney decisions, trustees, elder abuse risks, professional fiduciaries, pet trusts, digital assets, online accounts, passwords, and why failing to plan can leave critical decisions in the hands of the court. The second hour shifts to a major market story: SpaceX's highly anticipated IPO. Jeremiah and Alex break down how IPOs actually work, why many investors misunderstand them, the risks of buying into market hype, and how SpaceX could eventually impact index investors and retirement accounts through future index inclusion. The final hour focuses on practical planning decisions, including pension maximization strategies, large income windfalls from business sales and acquisitions, Medicare and tax planning considerations, and tax gain harvesting opportunities for investors sitting on significant unrealized gains. 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/] —————————————————————

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/] —————————————————————