Alan Grissom: Direct Indexing and Tax-Loss Harvesting (Part 2)

Alan Grissom and Coach Pete D’Arruda examine how direct indexing can create opportunities for tax-loss harvesting. They discuss using individual holdings to coordinate gains and losses, the technology behind managing portfolios at scale, and why wash-sale rules and other tax details require care. H…

Alan Grissom: Index Investing, Railroads, and the History of Wall Street (Part 1)

Tax strategist and entrepreneur Alan Grissom joins Coach Pete D’Arruda and Thomas Lipscomb to discuss how markets developed and why index investing became important. They explore the roots of the financial system, railroad investment, Cornelius Vanderbilt, and the relationship between active and pa…

Cam Harvey: Market Noise, Passive Investing, and Crypto (Part 1)

Duke University professor Cam Harvey joins Coach Pete D’Arruda to examine how fast-moving headlines and online trading can influence investment decisions. They discuss market noise, the growth of passive investing, the information advantage of institutional traders, and why patience matters. Harvey…

Sheridan Murphy: Business Owners, Entrepreneurs, and Planning an Exit

Sheridan Murphy joins Coach Pete D’Arruda and Thomas Lipscomb to discuss the distinction between building a business and running one. They explore how owners can separate personal wealth from the company, diversify beyond the business, plan an eventual exit, and coordinate financial decisions with …

Nile Nickel: AI, Robotics, and the Technology Changing Everyday Life

Technology expert Nile Nickel joins Coach Pete D’Arruda for a conversation about artificial intelligence and what the next wave of technology could mean for work, healthcare, transportation, and life at home. Nickel explains why he treats AI as an assistant whose answers still need review, then dis…

Tony Haynes and Chuck Kaiton: Changing Technology and Retirement Decisions (Part 2)

Tony Haynes and Chuck Kaiton continue their conversation with Coach Pete D’Arruda and Thomas Lipscomb. They discuss how technology is changing everyday life, share stories from the world of sports, and connect those changes with financial and retirement decisions. Hear the perspective of two longti…

Joe Casey: CES 2026, AI, and the Next Wave of Technology

Joe Casey shares his impressions of CES 2026 with Coach Pete and Thomas Lipscomb. They discuss artificial intelligence, robotics, quantum computing, blockchain, and how emerging technology could change work and investing. Call 800-661-7383 or text PLAN to 600-700. Transcript Automatically transc…

Stan Moore: Real Estate Depreciation and Backdoor Roth Questions (Part 4)

Stan Moore returns with Coach Pete D’Arruda for a final discussion of real estate depreciation and Roth IRA planning. They explore the mechanics of a backdoor Roth strategy, why other IRA balances can affect the tax calculation, and the importance of weighing a conversion against your circumstances…

Stan Moore: Cost Segregation, Senior Deductions, and Planning Ahead (Part 3)

Coach Pete D’Arruda and CPA Stan Moore discuss cost segregation for real estate, deductions affecting older taxpayers, and why income phase-outs deserve a closer look. They also consider the value of keeping accounting records current so a tax bill does not arrive as a surprise. Listen for topics t…

J.W. Roth: Building VENU and the Future of Live Music

J.W. Roth discusses his path from the food industry to VENU and the development of modern amphitheaters. The conversation explores financing, the live music experience, and bringing people together through entertainment. Call 800-661-7383 or text PLAN to 600-700. Transcript Automatically transcr…