Think First: Better Financial Decisions, Roth Strategies & Long-Term Care Planning (6/27/2026)

Think First: Better Financial Decisions, Roth Strategies & Long-Term Care Planning (6/27/2026)

Brian Wiley is joined by business coach and author Allison Dunn for a conversation about why critical thinking is one of the most valuable financial skills an investor, business owner, or retiree can develop. They discuss how better decision-making applies to retirement planning, leadership, investing, and navigating life's biggest financial choices. The show also answers listener questions on retirement planning, including how to coordinate 401(k)s, Traditional IRAs, HSAs, and Roth conversion strategies to improve tax efficiency. Brian explains why retirement accounts should be viewed both individually and as part of one comprehensive financial plan, while also discussing health insurance planning before Medicare eligibility. Later, the conversation turns to long-term care planning, estate planning, trusts, and the pros and cons of self-funding versus insurance-based solutions. They also explore fiduciary advice, family communication around money, Micron stock and concentrated positions, investor psychology, and why having a thoughtful process often leads to better financial outcomes than simply reacting to markets or emotions. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com [https://www.therealmoneypros.com] Guest: Allison Dunn, Author and Business Coach https://deliberatedirections.com/think-first-allison-dunn/ [https://deliberatedirections.com/think-first-allison-dunn/] ————— 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/] —————————————————————

Navigating Medicaid: How Families Can Protect Assets and Pay for Care

Most families don't think about Medicaid planning until they're facing a health crisis—but by then, some of the best planning opportunities may already be gone. Nic and Jeremiah are joined by Brooke Baker and Jessica Young of Legacy Navigation for an in-depth conversation about the realities of long-term care, Medicaid eligibility, and protecting family assets. Together, they break down the differences between Medicare and Medicaid, the true cost of care, common misconceptions about qualifying for benefits, and why so many families find themselves overwhelmed when a loved one suddenly needs assistance. The discussion explores real-world planning considerations, including asset protection strategies, the five-year lookback period, spousal protections, estate recovery rules, and the challenges families face when trying to navigate the complicated system on their own. Guests: Brooke Baker & Jessica Young Legacy Navigation https://legacynavigate.com/ [https://legacynavigate.com/] 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/] —————————————————————

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/] —————————————————————