Most investors chase performance, compare benchmarks, and debate active vs passive strategies but very few actually measure what lands in their pocket after taxes. Gary Pattengale argues that tax drag is one of the most underestimated forces in wealth erosion, often overshadowing market volatility itself. He breaks down why affluent families need to shift their mindset from headline returns to after-tax returns, and how thoughtful tax planning across accounts, assets, and income sources can change long-term outcomes dramatically. From tax-efficient fund selection to strategic asset location and multi-year planning, Gary provides a practical framework for transforming portfolios from “tax-leaky” to “tax-optimized.” Gary brings three decades of tax and wealth experience to help listeners understand how to keep more of what they earn, not just make more.

Equity compensation is a powerful wealth builder, yet many executives unknowingly treat it like income rather than a strategic tax asset. Gary explains why timing, and not valuation, is often the most important variable in maximizing the value of stock options and RSUs. He walks listeners through common pitfalls that lead to unnecessary taxes: exercising too late, holding too long, misunderstanding vesting rules, or triggering AMT exposure without planning. He also explores how executives can design multi-year tax strategies that convert employer-granted equity into long-term, after-tax wealth, whether they’re preparing for retirement, liquidity events, or major life transitions.Gary’s expertise helps executives turn confusing equity awards into tax-smart opportunities for generational wealth.

Retirement planning is often framed around saving and investing, but the withdrawal phase is where most tax mistakes happen. Gary explains how high-net-worth families can coordinate withdrawals across tax-deferred, taxable, and Roth accounts to reduce lifetime tax liability, not just annual taxes. He details when Roth conversions make sense, how to sequence distributions to avoid bracket creep, and why aligning withdrawals with Social Security, RMDs, and Medicare thresholds can materially extend portfolio longevity. Using real-world examples, Gary demonstrates how tax-aware withdrawal planning can unlock tens or hundreds of thousands of dollars in long-term savings. Gary brings a specialist’s perspective on how intelligent withdrawal strategies create more durable, tax-efficient retirement income.