Tax Loss Harvesting, Direct Indexing, and Smarter Market Strategy

Financial Safari with Coach Pete · May 22, 2026 · 57m

Coach Pete is joined by tax strategist and entrepreneur Alan Grissom for a conversation about indexing, tax strategy, and how technology is changing the way investors manage money. Alan explains the role of indices like the S&P 500 and Dow Jones Industrial Average, why passive strategies often outperform active management, and how direct indexing can give investors more control over their portfolios. The discussion also takes a historical detour through railroads, Wall Street, and Cornelius Vanderbilt to show how markets and wealth-building have evolved over time. From there, the episode digs…