Wealth Strategy: How Better Decision-Making Creates Better Investment Outcomes (With Annie Duke)

What if the greatest measure of wealth isn't your net worth, but how fully you're actually living your life? In this episode, Dave Wolcott welcomes back Eli Facenda, founder of Freedom Travel Systems and creator of the Experiential Wealth philosophy, to explore how entrepreneurs can turn financial success into meaningful experiences. They discuss Eli's six-part framework for creating unforgettable memories, how strategic travel rewards can help make luxury experiences more accessible, and why the ultimate return on investment may be the joy, connection, and freedom you create along the way. What You'll Learn Why financial success doesn't always translate into a fulfilling life—and how experiential wealth can change your perspective

You can have a multimillion-dollar portfolio and still find yourself financially vulnerable when unexpected expenses, taxes, or investment opportunities arise. In this special solo episode of Wealth Strategy Secrets of the Ultra Wealthy, Dave Wolcott explores three critical components of a coordinated wealth strategy: liquidity management, proactive tax planning, and advisor coordination. Discover why successful investors need to look beyond traditional retirement planning, anticipate major financial events, and build a wealth operating system that aligns their cash flow, investments, and long-term financial goals. What You'll Learn How to build a liquidity strategy that prepares you for unexpected expenses, capital calls, and future investment opportunities

What if one of the biggest threats to your wealth isn't market volatility, but the taxes you're unnecessarily paying? In this episode, Dave Wolcott sits down with Julio Gonzalez, founder and CEO of Engineered Tax Services, to explore how entrepreneurs and investors can move beyond traditional tax preparation and build a more proactive tax strategy. They discuss cost segregation, bonus depreciation, tax credits, business investments, and liquidity events—and how coordinating the right specialists can help preserve capital and support long-term wealth creation. What You'll Learn Why proactive tax planning can create more opportunities than simply preparing your taxes at year-end

You can have a growing net worth, multiple investments, and a team of advisors—and still feel like you're not getting any closer to financial freedom. In this special solo episode, Dave Wolcott explores why successful investors often reach a point where accumulating more assets creates more complexity instead of more freedom. From disconnected investments and reactive tax planning to liquidity gaps and siloed advisors, Dave explains how family office thinking can transform a collection of financial products into an integrated wealth operating system designed around your goals. What You'll Learn Why a growing net worth doesn't necessarily translate into greater passive income or financial freedom

What really drives exceptional returns in private equity—the financial model, the asset itself, or the people responsible for executing the strategy? In this episode, Dave Wolcott sits down with Scott Estill, Managing Partner at Lancor and adjunct professor at Columbia Business School, to explore how private equity is evolving and why exceptional operators can be one of the biggest differentiators in creating value. They discuss executive-led investing, evaluating management teams, the growing role of AI, human leadership, intellectual curiosity, and why leveraging your accumulated experience may be one of the most powerful ways to accelerate your wealth trajectory. What You'll Learn Why operational execution and management teams can be critical drivers of value creation in private equity