by mdean | Feb 2, 2026 | Tax
THE UNIVERSAL TAX PROBLEM Three Different Paths. One Expensive Problem. Scenario 1: You’ve built a $15M business over 20 years. Sale closes next year. Potential Tax bill: $4M+ Scenario 2: You’re a tech executive. Your stock options vest in 18 months....
by mdean | Feb 2, 2026 | Tax
WHEN SHOULD I START THINKING ABOUT THE TAX IMPLICATIONS? This is the question we get from: Business owners starting the exit process Executives watching their equity grow Early employees sitting on concentrated stock positions Here’s the...
by mdean | Feb 2, 2026 | Risk
THE DIVERSIFICATION DILEMMA There are planning approaches that allow you to diversify while actively managing the tax impact—not just accepting it. This matters if you: Hold stock representing 30%+ of your net worth Are an executive with concentrated...
by mdean | Feb 2, 2026 | Tax
UNDERSTANDING THE APPROACH How Long/Short Tax Aware Equity Strategies Work UNDERSTANDING THE APPROACH How does a “long/short tax-aware” equity strategy work? The Core Concept Traditional investing involves buying stocks you believe will go up...
by mdean | Oct 27, 2025 | Strategy
How Often Should You Review Your Portfolio – and Why It Matters Historical Frequency of Positive S&P 500 Returns (Illustrative data based on historical index perforamnce; past performance does not guarantee future results.) Key...
