At The Money: Tax Management for Investors

What It Covers

Barry Ritholtz and tax director Bill Artzeronian explain strategies to reduce tax burdens through Roth conversions, equity compensation management, and strategic asset location across different account types.

Key Questions Answered

• •Tax Diversification: Spread assets across pretax 401k accounts, after-tax brokerage accounts, and tax-free Roth accounts to create flexibility in retirement, avoiding situations where every withdrawal triggers taxable income at high rates.
• •Mega Backdoor Roth: Contribute up to 70k total to 401k plans in 2025 by adding 30k after-tax contributions beyond standard limits, then converting to Roth for tax-free growth if your employer plan allows this strategy.
• •Concentrated Stock Management: Use direct indexing to harvest tax losses against concentrated equity positions, or employ 351 exchanges to bundle individual stocks into diversified ETFs while deferring capital gains through basis preservation until death.