Strategies For Minimizing Taxes On Investment Accounts

Most Family Offices don’t lose wealth by making poor investment decisions—they lose it through inefficiencies. Taxes, fees, and outdated structures quietly erode returns, often without investors realizing it. The most sophisticated Family Offices have figured this out. Instead of focusing solely on higher returns, they prioritize something far more impactful: Structural Alpha. This isn’t about choosing the best hedge fund or private equity deal. Structural Alpha is about optimizing how investments are structured to maximize after-tax returns and eliminate inefficiencies. It’s a way to achieve stronger outcomes not by taking on additional risk but by being more strategic about how capital is deployed. A prime example is Private Placement Life Insurance (PPLI), a tax-efficient structure that allows Family Offices to significantly reduce the tax burden on investments like credit funds. Without it, returns on a credit strategy might shrink from ten percent to seven percent after taxes. With PPLI, those gains can be preserved for a fraction of the cost. Another example is tax-aware investing. Tax-loss harvesting extends far beyond its original application, allowing Family Offices to structure portfolios in a way that minimizes tax liabilities without compromising performance. For Family Offices, this isn’t just an advantage—it’s an essential approach to wealth management. Family Offices exist to preserve and grow generational wealth, yet many still operate within traditional investment frameworks that leave money on the table. By integrating Structural Alpha strategies, they can improve after-tax returns without taking on unnecessary risk, reduce compounding inefficiencies, and ensure long-term capital preservation through smarter structuring. The most forward-thinking Family Offices aren’t just searching for strong investments—they’re refining how they invest. Structural Alpha isn’t a trend; it’s a shift in approach that separates those who quietly optimize their wealth from those who unknowingly give a portion of it away.

If you're a crypto investor, the current bull run may have you considering taking profits. While realizing gains can be exciting, it’s important to think about the tax implications before making any moves. Here are some tax planning ideas to help minimize your capital gains tax liability: 1. **Hold for Over a Year**: If possible, hold your crypto assets for at least one year before selling. Long-term capital gains are generally taxed at a lower rate (0%, 15%, or 20%) compared to short-term gains, which are taxed as ordinary income. 2. **Offset Gains with Losses**: If you have other crypto or investment losses, consider selling those assets to offset your gains. This strategy, known as tax-loss harvesting, can help reduce your taxable income. 3. **Consider Tax-Advantaged Accounts**: If you’re investing in crypto through a tax-advantaged account like a self-directed IRA, any gains might grow tax-deferred or even tax-free (if it’s a Roth account). 4. **Donate Crypto**: Donating appreciated crypto assets to a qualified charity can provide a tax deduction for the fair market value while avoiding capital gains tax on the appreciation. 5. **Strategic Selling**: Spread out your crypto sales across multiple tax years to potentially keep your income in a lower tax bracket. 6. **Leverage Gifting**: You can gift crypto to family members in lower tax brackets, staying within the annual gift tax exclusion limit ($17,000 per recipient in 2024). They may pay lower capital gains tax when they sell. 7. **State Tax Planning**: If you live in a state with high income taxes and are planning a move to a state with no or low income tax, consider waiting until after your move to sell your crypto. 8. **Stay Compliant with Reporting**: The IRS is increasing scrutiny on crypto transactions, especially with new reporting requirements like Form 1099-DA starting in 2025. Ensure all your transactions are accurately tracked and reported to avoid penalties. Crypto tax planning can get complex, especially if you have significant transactions or use DeFi, NFTs, or other advanced crypto strategies. If you need help navigating the tax implications of your crypto investments, let’s connect! Our team specializes in crypto tax planning and compliance, and we’re here to help you make the most of your gains. #cryptotax #taxplanning #cryptoinvestment #capitalgainstax #cryptocpa

Most high-income professionals overpay in taxes not by a little, but by hundreds of thousands of dollars. And the worst part? Most of them don’t even realize it’s happening I recently worked with an executive who was unknowingly missing out on over $500,000 in potential tax savings. Like many high-income professionals, she assumed her CPA was handling everything. But here’s the problem: 🚫 Most CPAs think backwards, not forwards. They file taxes based on what already happened. 🚫 They don’t integrate financial planning, investments, and tax strategy. 🚫 Some of them miss opportunities that can save you money long-term. How We Fixed It & Saved Her Over $500K ✅ 1. The HSA Strategy – $20K+ in Lifetime Tax Savings She had access to an HSA (Health Savings Account) but wasn’t using it. Why does this matter? 👉🏾HSA contributions are tax-deductible. 👉🏾The money grows tax-free. 👉🏾Withdrawals for medical expenses are tax-free. By fully funding it every year, she’ll save $20,000+ in taxes over her lifetime. But here’s the kicker: we also helped her invest it properly so the account grows instead of just sitting in cash. ✅ 2. The Roth Conversion Strategy – $500K+ in Tax-Free Growth She was anticipating losing her job and had multiple old retirement accounts just sitting there. Instead of letting those accounts stagnate, we saw an opportunity: 👉🏾She was having a low-income year, which meant she could convert $100,000 into a Roth IRA at a lower tax rate. 👉🏾That $100K will now grow tax-free—meaning if it reaches $600K or $700K in retirement, she’ll never pay a cent in taxes on that money. ✅ 3. The Bonus Strategy – Tax-Loss Harvesting We also helped her offset investment gains using tax-loss harvesting, a strategy that allows you to sell underperforming investments and use the losses to reduce your tax bill. By combining these strategies, we helped her: 💰 Save $20K+ in taxes on HSA contributions 💰 Unlock $500K+ of future tax-free income through Roth conversions 💰 Offset capital gains and lower her tax bill through tax-loss harvesting And she almost missed out on all of this because she assumed her CPA was handling everything. If you’re making multiple six figures, but you aren’t actively planning your tax strategy, you’re leaving money on the table plain and simple. The best financial strategies aren’t about making more money they’re about keeping more of what you earn. If you want to see where you might be overpaying, shoot me a message. Let’s make sure you’re taking advantage of every opportunity. P.S See the look on my face…don’t make me have to give you that look because you’re paying more than your fair share in taxes. 😂

Many high earners lose up to five figures from poor tax planning. Here’s what to check before year-end: →Equity compensation Plan for taxes on RSUs, ESPPs, NSOs, and ISOs before exercising or selling. → Tax diversification Spread assets across pre-tax, Roth, and taxable accounts for flexibility. → Charitable donations Lump-sum giving can help you exceed the standard deduction and increase tax efficiency. → Tax-loss harvesting Offset gains, deduct up to $3,000 in losses, and clean up your portfolio. → Roth conversions Move funds from pre-tax to Roth when markets or income are lower. → HSAs Triple tax benefit: pre-tax contributions, tax-deferred growth, and tax-free withdrawals for qualified expenses. → 401(k) optimization Choose pre-tax or Roth contributions based on your current vs. future tax outlook. → 529 plans Tax-free growth, Roth rollovers, and the ability to front-load 5 years of contributions. →Real estate Use 1031 exchanges, expense write-offs, and other strategies to reduce taxable income. → Gifting Annual exclusion is $19,000 per person in 2025; larger gifts tap into your lifetime exemption ($13.99 million per individual and $27.98 million per marriage). The earlier you review, the more options you’ll have before December 31st. Which one of these will you be tackling first?