Tax Planning Services for High-Net-Worth Families

Strategic tax planning coordinates withdrawals, conversions, and distributions across your taxable, tax-deferred, and tax-free accounts to minimize taxes paid over your lifetime. By modeling Roth conversions during lower-income years, harvesting tax losses to offset gains, sequencing withdrawals to manage tax brackets, and timing charitable distributions for maximum deductions, we ensure every dollar is sourced from the most tax-efficient account each year. This proactive approach can save high-net-worth families hundreds of thousands in taxes compared to reactive, year-to-year planning.

Tax preparation is backward-looking—it files returns based on decisions already made. Tax planning is forward-thinking—it strategically coordinates your financial decisions throughout the year to minimize future tax obligations. While your CPA prepares returns, Sentinel architects the underlying strategy: when to realize gains, which accounts to withdraw from, how to time Roth conversions, and how to structure trusts and charitable gifts. We work collaboratively with your tax preparer, ensuring every decision aligns with current IRS rules and your long-term wealth preservation goals.

Roth conversions strategically move funds from tax-deferred accounts (like traditional IRAs) to tax-free Roth accounts, paying taxes now at potentially lower rates to eliminate Required Minimum Distributions and future tax obligations. For affluent families, this strategy is particularly powerful: it reduces taxable estate size, creates tax-free inheritance for heirs, and provides flexible, penalty-free withdrawals. We model multi-year conversion strategies that fill lower tax brackets before Social Security or RMDs begin, maximizing long-term tax efficiency while preserving liquidity and legacy goals.

Effective multi-generational tax planning uses trusts, strategic gifting, and account structuring to minimize estate taxes and maximize inherited wealth. We design irrevocable trusts to remove assets from taxable estates, implement annual gift exclusions to transfer wealth tax-free during your lifetime, structure step-up basis strategies for appreciated assets, and coordinate beneficiary designations to direct tax-free Roth accounts to younger heirs. Combined with Qualified Charitable Distributions and dynasty trust planning, these strategies preserve family wealth across generations while honoring your values and philanthropic intentions.

Tax-loss harvesting strategically sells investments at a loss to offset capital gains and reduce taxable income by up to $3,000 annually, with unused losses carried forward indefinitely. For high-net-worth portfolios, this creates ongoing tax savings: we identify underperforming positions, harvest losses during market downturns, immediately reinvest in similar assets to maintain portfolio allocation, and use accumulated losses to offset future gains from rebalancing or required distributions. This disciplined approach transforms market volatility into tax advantages, improving after-tax returns without altering your investment strategy.

Qualified Charitable Distributions (QCDs) allow individuals 70½ or older to transfer up to $100,000 annually from IRAs directly to qualified charities, satisfying Required Minimum Distributions without triggering taxable income. For affluent families, QCDs provide triple tax benefits: they avoid income tax on distributions, reduce adjusted gross income (lowering Medicare premiums and Social Security taxation), and satisfy RMD requirements. This strategy is particularly powerful for retirees who don't need IRA income and wish to support charitable causes while minimizing lifetime tax liability and estate size.

Investment in tax planning varies based on portfolio complexity, number of accounts, trust structures, and multi-generational goals. Sentinel operates on a fiduciary, fee-based model—our compensation is transparent and aligned with your success, never tied to product sales or commissions. During your initial consultation, we'll assess your tax situation, project potential savings from coordinated planning, and provide a clear fee structure. For many high-net-worth families, strategic tax planning delivers multiples of its cost in tax savings within the first few years alone.

Absolutely. Effective tax planning requires collaboration across your advisory team. We coordinate closely with your CPA to align investment decisions with tax filing strategies, share projections for estimated payments and withholding, and ensure Roth conversions and distributions are timed optimally. We also work alongside estate attorneys to review trust structures, beneficiary designations, and titling for tax efficiency. This integrated approach ensures every professional on your team works toward the same goal: minimizing lifetime tax liability while preserving your wealth and legacy.