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The Tax Shift
Most people don’t realize their tax life changes long before retirement. This edition breaks down how your income shifts from W2 to capital gains, where real tax planning opportunities come from, and how to think strategically at every stage. Learn the three levels of tax planning that can help you build lasting wealth and keep more of what you earn.
The AI Paradox
AI investment is fueling historic market growth, but also reshaping jobs and families’ futures. In this edition, we explore how today’s tech titans mirror the industrial giants of the past, what $400B in AI spending means for your retirement, and why investors must weigh both the rewards and risks of this new economic revolution.
The Quiet Market That Rules
Stocks continue to rise on the back of AI, government spending, and IPO momentum, but bonds are sending very different signals. Higher yields, sticky inflation, and heavy government debt are reshaping the fixed income landscape. For retirees, understanding bond exposure is critical because fixed income drives cash flow, stability, and diversification. This edition explains why knowing your bond portfolio may be the key to long-term retirement security.
Why Cash Flow Matters
Cash flow is the overlooked cornerstone of financial health. In this edition, Tom shares why even wealthy families struggle with money stress when cash flow isn’t managed—and how mastering it creates clarity and freedom in retirement. Drawing on real client stories, personal experience, and lessons from top business leaders, Tom explains why cash flow matters more than profits, how it reveals true financial strength, and the biggest traps families face when they retire.From ignoring RMDs to poor timing of withdrawals or overspending early in retirement, these mistakes can quietly erode wealth and peace of mind. Tom highlights that cash flow isn’t about perfection or penny-pinching—it’s about rhythm, consistency, and designing a retirement where wealth serves your life, not the other way around.The clear takeaway: if you don’t measure and control cash flow, no amount of money will ever feel like enough. But if you get the rhythm right, everything else falls into place.This edition is for families who want to transform financial stress into clarity, reduce tax surprises, and create the freedom to retire with confidence.
Cash-Flow Traps
Learn how illiquid, cash‐draining assets can starve even large estates of spendable income, using Jimmy Buffett’s $275M trust dispute as a real‐world case study. We break down the portfolio mix, why minority ownership and hard‐asset overhead crush yield, and the simple moves that restore liquidity and control. Get a practical playbook for targeting dividend yield, sizing a liquidity runway, and selecting trustees to prevent costly conflicts.
What Jimmy Buffett’s Unintended $275M Mistake Can Teach Us
Jimmy Buffett's $275 million estate dispute offers crucial lessons for wealthy families about trust structures and estate planning pitfalls that can tear families apart. This in-depth analysis breaks down the marital trust complications between Buffett's widow Jane and former advisor, revealing how poor trustee selection turned a 47-year marriage legacy into public legal battles. Learn actionable estate planning strategies to protect your family from similar disputes, including trustee selection best practices and communication tactics that prevent inheritance conflicts.