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 Hosts: Jeremiah Bates & Brian Wiley ————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————