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 into tax loss harvesting and how selling gains alongside offsetting losses may help reduce taxable exposure. For listeners looking to keep more of what they have earned, this episode offers a practical look at tax-aware investing strategies that were once mostly available to the ultra-wealthy.