Alexander Zimmerman

Meet Alexander, a 58-year-old former tech executive who has retired after a successful career at a major Silicon Valley firm. He has accumulated $5 million in liquid assets through his salary, bonuses, and stock options. However, his financial situation presents certain challenges:

1. Concentrated Position: Alexander has $2 million invested in his former employer's stock, which represents 40% of his portfolio. This position has appreciated significantly from a low cost basis of $500,000, resulting in an unrealized capital gain of $1.5 million.
2. Current Allocation: His portfolio follows a traditional 60/40 split, with 60% in equities and 40% in bonds. Specifically, this includes $3 million in equities ($2 million in concentrated stock and $1 million in broad-market ETFs) and $2 million in investment-grade fixed income.
3. Goals: Alexander aims for steady growth to support a comfortable retirement, with annual withdrawals of approximately 4%. He seeks to minimize volatility, taxes, and the risk of a market downturn affecting his concentrated holding. He is in a high tax bracket, subject to a federal long-term capital gains rate of 20% plus a 3.8% Net Investment Income Tax.
4. Challenges: The concentrated stock exposes him to company-specific risks, such as sector downturns in tech, with historical volatility around 40% annually, which is significantly higher than the market's 15%. Selling the stock outright to diversify would result in approximately $357,000 in immediate taxes, reducing his principal. His current expected annual return is 7.6%, based on 10% for equities and 4% for bonds, but with elevated risk (standard deviation of 18.8%). Without intervention, a 30% drop in his concentrated stock, which is plausible in a tech correction, could result in a $600,000 loss, jeopardizing his retirement.

A Shift to 60/20/20 with Advanced Tools
Alexander's recommendation could include transitioning to a more sophisticated 60/20/20 allocation (60% equities, 20% alternatives, 20% bonds) to enhance returns, reduce risk, and optimize taxes. Key elements include:

• Direct Indexing for Equities ($3 million): Instead of ETFs, we use direct indexing to own individual stocks replicating the S&P 500. This allows systematic tax-loss harvesting—selling underperforming stocks to realize losses that offset gains elsewhere. Historical studies show this adds 1-1.5% in annual "tax alpha" by deferring or reducing capital gains taxes. For Alexander, this means harvesting losses on volatile holdings to gradually offset the tax hit from diversifying his concentrated position.
• Evergreen Private Equity Funds for Alternatives ($1 million): We allocate to evergreen funds (open-ended structures providing ongoing access to private equity deals without traditional lock-ups). These funds invest in mature buyout opportunities, offering liquidity options and diversification across sectors. Based on the Cliffwater Evergreen Private Equity Index, these have delivered ~13% annualized returns over the past five years, outperforming public equities with lower correlation.
• Bonds ($1 million): Retain high-quality bonds for stability, but reduce exposure to free up capital for higher-return alternatives.

To execute, we phased the sale of the concentrated stock over 12-18 months, using harvested losses from the direct-indexed portfolio to offset gains. This minimized the initial tax bite to under $100,000 (vs. $357,000 upfront). The portfolio remains fully invested, with ongoing rebalancing to maintain the 60/20/20 target.

Using historical benchmarks—S&P 500 geometric returns of ~10% (1928-2024), U.S. Treasury bonds at ~4%, and evergreen private equity at 13%— modeled the portfolios. Assumptions include moderate correlations (e.g., 0.6 between equities and private equity) and a 1.5% tax alpha from direct indexing applied to the equity sleeve.

Current 60/40 (with Concentration):

• Expected Annual Return = 7.6%
• Annual Volatility (Std. Dev.) = 18.8%
• Sharpe Ratio (Risk-Adjusted Return, assuming 3% risk-free rate) = 0.25
• 10-Year Projected Value (from $5M starting) = $10.4 million
• Effective Tax Drag on Gains (Annualized) = ~0.8% (due to inefficient harvesting)

Proposed 60/20/20 (Optimized):

• Expected Annual Return = 10.3% (9.4% base + 0.9% tax alpha)
• Annual Volatility (Std. Dev.) = 12.1%
• Sharpe Ratio (Risk-Adjusted Return, assuming 3% risk-free rate) = 0.61
• 10-Year Projected Value (from $5M starting) = $13.3 million
• Effective Tax Drag on Gains (Annualized) = ~0.2% (with direct indexing)

Improvement:

• Expected Annual Return = +2.7%
• Annual Volatility (Std. Dev.) = -35% reduction
• Sharpe Ratio (Risk-Adjusted Return, assuming 3% risk-free rate) = +144%
• 10-Year Projected Value (from $5M starting) = +$2.9 million
• Effective Tax Drag on Gains (Annualized) = -75% reduction

• Return Breakdown: The proposed portfolio's higher return stems from private equity's premium (13% vs. 10% for public equities) and tax savings. Over 10 years, this compounds to an extra $2.9 million in wealth—enough to fund an additional decade of retirement spending at $200,000/year.
• Risk Reduction: By diversifying the $2 million concentrated position, we cut portfolio volatility by over a third. In a stress test (e.g., 2008-like crash), the current setup could lose 25-30% ($1.25-1.5 million); the optimized version limits this to 15-20% ($750,000-1 million).
• Tax Efficiency Example: In year one, direct indexing generated $150,000 in harvested losses (realistic for a volatile market), offsetting 100% of the gains from partial stock sales. Over five years, this saved Alexander ~$250,000 in taxes compared to a DIY approach—directly adding to his net worth.
• Long-Term Growth: Assuming 4% annual withdrawals ($200,000), the current portfolio sustains for ~25 years (Monte Carlo simulation at 95% confidence). The proposed extends this to 35+ years, providing legacy potential for his family.

This case study is just a hypothetical example, but I do hope it has helped illustrate the benefits of partnering with a Morgan Stanley advisor. My goal is to offer more than just asset allocation; but also provide a comprehensive approach to optimizing your financial strategy. For clients like Alexander, this means transforming potential vulnerabilities into strengths through personalized financial planning.

• Enhanced Wealth Potential: By leveraging superior returns and effective risk management, clients can potentially see significant growth in their wealth over time.
• Tax Efficiency: Our proactive strategies, such as tax-loss harvesting and phased diversification, can lead to substantial tax savings, helping to preserve more of your wealth.
• Risk Mitigation: We focus on reducing concentration risk, which can protect your portfolio from significant market downturns, providing peace of mind and financial security.
• Continuous Oversight: With regular reviews and access to exclusive investment opportunities, our advisors ensure that your financial plan adapts to changing market conditions and life events.

If you have concentrated holdings and seek tax-efficient growth, I invite you to explore how I can help tailor a strategy to meet your unique needs. As a Morgan Stanley advisor, my goal is to help you add significant value to your financial journey.