GenCrest celebrates  a year of growth and gratitude.

Ashley Madden leads a comprehensive roundtable discussion on personal financial planning for entrepreneurs, focusing on exit strategies and maximizing success post-business sale through the “three-legged stool” approach. She presents data on business owner demographics and exit planning trends, emphasizing the importance of pre-transition value enhancement and having a formal exit team while noting that many owners regret selling their companies. The session covers various aspects of business transitions, including financial planning, retirement strategies, and the use of tools like Quist’s Spotlight and eMoney software for comprehensive financial planning and exit preparation.

One Big Beautiful Bill – what does it really mean for your wealth and your tax planning?
Ashley Madden and Nora Fitzgerald break it all down in plain language — what’s changing, what’s staying, and where strategic planning can make all the difference.

As we approach the close of another year, many families begin asking the same questions: “How much should I give?” and “Where should those gifts go—to family, church, or charity?” These are meaningful questions that go far beyond tax efficiency. They touch the heart of what legacy truly means—passing on not just wealth, but wisdom and values.

1. The Strategic Side of Generosity
From a financial standpoint, year-end gifting offers a unique opportunity to align your generosity with smart planning. The 2025 gift tax exclusion allows individuals to give up to $19,000 per recipient (or $38,000 per couple) without tapping into lifetime exemption amounts. For families looking to reduce future estate tax exposure, this can be a simple yet powerful tool—especially when gifts are made consistently over time.

For larger gifts, the lifetime estate and gift tax exemption currently passed into law at $13.99 million per individual (double that for married couples).

2. Family Gifting: More Than a Financial Transaction
When gifting to family, remember that you’re not just transferring assets—you’re transferring trust and responsibility. Consider pairing financial gifts with educational conversations or experiences that help the next generation understand stewardship, investment principles, and philanthropy. For example:

• Contribute to a grandchild’s 529 education plan.

• Gift shares of a family investment portfolio and involve them in review discussions.

• Use a donor-advised fund (DAF) to let children help choose charitable beneficiaries.

These acts reinforce values that last far longer than the dollars themselves.

3. Giving Back: Faith, Philanthropy, and Community

Many clients also feel a deep desire to give back—to their church, alma mater, or community causes. Charitable giving remains a cornerstone of legacy planning, not only for its impact but also for its tax efficiency. Strategies to consider:

• Appreciated stock gifts can help you avoid capital gains tax while supporting organizations you care about.

• Qualified charitable distributions (QCDs) from an IRA (for those 70½ and older) can satisfy required minimum distributions while reducing taxable income.

• Donor-advised funds provide flexibility—fund your account this year, take the deduction now, and decide on recipients later.

For those whose faith guides their giving, this is also a time to reflect on stewardship. Giving to your church or faith-based organization not only strengthens your community but aligns your wealth with your values—an essential part of any legacy plan.

4. The “How Much Should I Give?” Question
There’s no single formula for generosity. The best approach balances intent, capacity, and timing. Ask yourself:

• What do I want my wealth to accomplish—for my family, my community, and my beliefs?

• How can I give meaningfully today without compromising long-term financial security?

• Do my giving strategies align with my estate plan, trust structures, and tax position?
Working with your advisory team—financial, legal, and tax—ensures that your generosity is both heartfelt and strategic.

5. The Legacy Beyond the Ledger
Ultimately, legacy planning isn’t about numbers on a balance sheet—it’s about values, stories, and impact. Whether you’re funding scholarships, supporting ministries, or empowering the next generation, your giving reflects who you are and what you believe in.
As you review your year-end strategy, take time to pause and reflect. This season is about gratitude—an opportunity to give generously, plan wisely, and build a legacy that outlives you.

Legacy planning for ultra-affluent individuals is no longer just about wills and distributing assets. The world has shifted. Tax laws, family dynamics, global exposures, digital assets, and social values all play critical roles. If you want your legacy to endure—and be aligned with who you truly are – here are five essential steps to do it right in today’s environment.

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1. Clarify Values, Vision & Goals (Beyond Dollars)

Why it matters now:

• Ultra-wealthy clients increasingly want their legacy to be more than just financial. They ask: What story do I want my children to inherit? What values, what philanthropic causes, what social impact? Oppenheimer.com+1
• With greater mobility, digital presence, blended families, global assets—the intangible parts of legacy (values, mission, purpose) often risk being lost unless made explicit early.

Key actions:

• Write (or update) a legacy mission statement. What matters most: education, entrepreneurship, philanthropy, environmental impact, etc.
• Hold “legacy conversations” with heirs: what they expect, what they know, what they need. Transparency helps avoid distrust or misalignment later. Nerd’s Eye View | Kitces.com+1
• Decide what non-financial assets matter (e.g. family heirlooms, intellectual property, brands, businesses) and how they are to be passed on or preserved.

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2. Build a Sophisticated, Flexible Estate & Trust Architecture

Why it matters now:

• Tax laws are in flux: exemptions for estate, gift, and generation-skipping taxes are scheduled to change. For example, some forecasts show reductions in federal estate tax exemptions in coming years. savvywealth.com+2Colva Insurance Services+2
• Assets are more complex: multiple jurisdictions, passive income, business interests, alternative assets, digital holdings, cryptocurrencies. Existing estate plans often aren’t built to handle these smoothly. Vanilla+1

Key actions:

•  Use a mix of revocable and irrevocable trusts, dynasty trusts, generation-skipping trusts, etc., to control what happens, while managing tax exposure. DK Law Group – Estate Planning Maryland+2Colva Insurance Services+2
• Structure business succession plans for family businesses or partnerships now. Identify successors, train them, align incentives. Avoid last-minute disruptions.
  apsitaxes.com+2First Western Trust Bank+2
• Include powers of attorney, healthcare directives, and mechanisms for incapacity. These are often overlooked until too late. Investopedia+1

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3. Tax-Efficient Wealth Transfer & Gifting Strategies

Why it matters now:

• As mentioned, tax exemptions may shrink; the laws around estate, gift, generation skipping taxes are under pressure. Delaying can cost materially. savvywealth.com+2Colva Insurance Services+2
• Strategic gifting during lifetime not only reduces estate size (reducing tax burden), but also allows you to see your beneficiaries benefit, and potentially shape how they use wealth.  DK Law Group – Estate Planning Maryland+2ocelderlaw.com+2

Key actions:

• Take advantage of annual gift tax exclusions, and regularly make gifts within those limits. Use gift-splitting with a spouse where applicable. DK Law Group – Estate Planning Maryland
• Use specialized trusts (e.g. lifetime or grantor trusts, GRATs, IDGTs) to transfer appreciating assets outside of your taxable estate. Colva Insurance Services+1
• Consider charitable vehicles: charitable remainder or lead trusts, private foundations, donor advised funds – both to support causes you believe in and to gain favorable tax treatment. apsitaxes.com+2rbfcu-org+2

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4. Embrace Technology & Global Risk Management

Why it matters now:

• Many legacy plans are outdated or incomplete; digital assets (passwords, crypto, social media, NFTs, etc.) often are not properly included. Cornerstone Wealth Group
• Global exposure introduces risks: foreign assets, changing tax treaties, currency risk, regulatory risk, geopolitical issues. What works in one jurisdiction may be penalized in another. First Western Trust Bank+1

Key actions:

• Inventory all assets, including digital (online accounts, cryptocurrencies, digital IP, domain names, etc.). Ensure there are secure, documented instructions for access & transfer in the event of incapacity or death. . Cornerstone Wealth Group
• Use secure, collaborative platforms for document management (trusts, wills, agreements) to allow updates, monitoring, and version control. Consider integrating legal, tax, financial data in one system. . Cornerstone Wealth Group
• For cross-border or internationally-exposed families or assets: get advice on multijurisdiction estate & tax law; be mindful of foreign bank account reporting, residency, citizenship, and treaty benefits.

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5. Governance, Education, & Succession: Preparing the Next Generation

Why it matters now:

• One of the biggest risks to legacy is the heirs not being prepared. Often wealth is lost or diluted through mismanagement, family conflict, or lack of alignment. Brady Ware CPAs+1
• As family structures become more complex (multiple marriages, blended families, nontraditional arrangements), without proper communication and governance, disputes or unintended consequences are common.

Key actions:

• Establish a governance framework: family councils, regular meetings, advisory boards, mentoring for successors. Clarify roles, expectations, responsibilities.
  Nerd’s Eye View | Kitces.com+1
• Educate heirs: financial literacy, investing principles, tax awareness, stewardship. Give them exposure to the decision-making process well before they need to act.
• Revisit and update the plan regularly: any major life event (marriage, divorce, birth, death, relocation), changes in laws, shifts in your values or priorities should trigger a review. A static plan is a brittle one. savvywealth.com+1

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Final Thoughts

Legacy planning in today’s climate is as much about control, flexibility, values, and relationships as it is about minimizing taxes or distributing assets. For families with substantial wealth, the cost of inaction or delay is high—not just financially, but
emotionally and reputationally.

If you put these five steps at the center of your planning, you’ll be much better positioned to leave a legacy that endures, that reflects who you are, and that serves your family, community, and chosen causes well into the future.

At the Fed meeting in Jackson Hole on August 22^nd, Jerome Powell’s dovish leaning remarks signaled that the balance of economic risk “may warrant” a policy stance adjustment.  After these remarks, the markets soared and immediately raised the odds on a 25 basis point cut in federal funds on September 17^th.  Markets are currently pricing in an 85% probability of a September rate cut and 54 bp of easing this year.

There is still plenty of scrutiny surrounding this dovish tilt amid lingering tariff-driven inflation concerns, labor market softening, rate-cut uncertainty and political pressure.  The potential tailwinds for the market driven by the Fed easing expectations are countered somewhat by the overhang at the index level, given the growth this year has been concentrated in a few names.

AI is still the biggest thematic tailwind for market sentiment, though more recent focus has been on the capex bubble, competition and monetization concerns.  Trade has moved somewhat to the back burner over the last month or so after a flurry of deal announcements, but tariff headline risk is not going away.  There has also been discussion about how retailers are expecting to start seeing more cost pressure from tariffs and how much of higher prices companies are going to pass on to the consumer.

Amid all this uncertainty, we continue to remain cautious especially considering the high valuations of the current markets and the fact that September is historically the worst month for the markets on an annual basis.  As always, please feel free to contact any of our team if you have any questions.

This material is provided for informational purposes only and is not intended to be investment advice or a recommendation to take any action. The forecasts or forward-looking statements are based on assumptions, may not materialize, and are subject to revision without notice.

Source: Fact Set

• Nothing particularly incremental from a narrative perspective in the wake of the more dovish leaning remarks from Fed Chair Powell on Friday. However, still plenty of scrutiny surrounding this dovish tilt amid lingering tariff-driven inflation concerns, labor market softening, rate-cut timing uncertainty and political pressure. Market currently pricing in a ~85% probability of a September rate cut and 54 bp of easing this year. Rotations driven by Fed easing expectations a positive from a breadth perspective though also a potential overhang at the index level given concentration dynamics. Ahead of Nvidia earnings this week, AI still the biggest thematic tailwind for market sentiment, though more recent focus has been on capex bubble, competition and monetization concerns. While trade has moved somewhat to the back burner over the last month or so following a flurry of “deal” announcements, tariff headline risk not going away with Trump disclosing investigation into furniture (which came roughly a week after a 400+ product/$210B+ expansion of steel and aluminum tariffs). Also further discussion about how retailers expected to start seeing more cost pressure from tariffs and pass along higher prices to consumers. Positive corporate guidance and earnings revision trends, elevated buybacks, seasonal headwinds, elevated tech positioning, hawkish BoJ, China policy support, China stock market breakout, big M&A, private equity fundraising slowdown and biggest decline in government employment since WWII among some of the topics recently discussed by the Street and/or in the financial press.

 

When navigating the dissolution of a high-net-worth marriage, attorneys are often laser-focused on equitable division and legal compliance. But overlooking capital gains tax implications in asset division can lead to costly, unintended consequences for your clients.

High-value portfolios — including real estate, investment accounts, business interests, and collectibles — often come with significant unrealized capital gains. And while transfers between spouses during divorce are generally non-taxable under IRC Section 1041, what happens after is where the real impact lies.

Below is a strategic overview to help you better serve your clients by proactively addressing capital gains during divorce proceedings.

Capital Gains & Divorce: The Essentials

• IRC Section 1041 Transfers
  Transfer of property between spouses or incident to divorce are generally non-recognition events. This means no immediate tax is due at the time of transfer. However, the original cost basis and holding period carry over to the receiving spouse.
• Built-In Gains Trap
  If one spouse receives an asset with significant unrealized gains, and then sells it post-divorce, they may face a large capital gains tax burden — even if they received that asset “tax-free” during the split.
• Property Type Matters
  Primary residences, rental properties, stocks, private equity interests, and art/collectibles all carry different rules, exemptions, and tax treatments. For example:
  • Primary residence exclusion may be lost or limited post-divorce. If the primary residence has appreciation, it could result in additional tax if sold by a taxpayer now filing single or head of household.
  • Carried interests or restricted stock may have complex vesting or valuation implications.
• State Tax Differences
  If spouses reside in different states, state capital gains treatment can differ widely and should be factored into the settlement strategy.
• Rental Real Estate
  Can also carry accumulated depreciation which is taxed additionally at the sale of the property.

Attorney’s Capital Gains Consideration Checklist

Use this checklist to guide your client conversations and collaborate more effectively with financial and tax professionals:

 Asset Review

• Identify all assets with unrealized capital gains or losses.
• Determine cost basis and holding periods for each asset.
• Flag assets with illiquid or complex valuation (e.g., business ownership, private equity).

Equitable + Tax-Efficient Division

• Ensure division is not just equal in value, but fair in after-tax value.
• Run hypothetical sale scenarios to project potential capital gains tax burden for each spouse.

Real Estate Considerations

• Confirm if primary residence exclusion ($250k per spouse) still applies.
• Assess whether post-divorce use affects exclusion eligibility.
• If keeping the house, calculate future capital gains exposure.

Investment & Business Interests

• Clarify ownership of carried interest, restricted stock, or deferred comp.
• Address control, voting rights, and liquidation potential.
• Consider installment sale structures or Qualified Domestic Relations Orders (QDROs) where applicable.

 Client Preparation

• Recommend a joint session with a CPA or tax advisor before finalizing settlement.
• Encourage tax projections to inform decision-making, not just after-the-fact reporting.
• Emphasize post-divorce tax planning to avoid surprises at sale or filing time.

Download your checklist here.

Final Thought

Divorce is already emotionally and financially taxing. For high-net-worth clients, it can also trigger steep and unexpected tax bills if capital gains implications aren’t fully considered. As a trusted legal advisor, you can elevate your counsel by ensuring that asset division accounts for both legal equity and tax efficiency — ideally in collaboration with a qualified tax consultant.

If you’re an attorney seeking strategic tax insights for your client’s divorce proceedings, We are available for consults and white-glove collaboration. Let’s help your client land on both feet — legally and financially.

The “One Big Beautiful Bill Act” (OBBBA) was signed into law by President Donald Trump on July 4^th, 2025. The initial bill, first approved by the House on May 22^nd, passed through the Senate with minimal yet subtle changes, retaining the majority of its original blueprint. The final bill was approved by the House in a close 218-214 vote and encompasses nearly 900 pages.

In our last Tax Update, we shared a number of potential provisions that could impact the high-net-worth clients of GenCrest Capital Partners. Below are final results of those provisions, plus additional ones for tax planning awareness and consideration. At GenCrest Capital Partners, we recognize these potential impacts and are here with you every step of the way. Let’s navigate these changes together to help ensure financial success for you and future generations.

Key provisions:

• 2017 Tax Cuts and Jobs Act (TCJA): OBBBA made permanent (with some modifications) many aspects of the TCJA otherwise set to expire at the end of 2025. These include lower tax brackets, increased standard deductions, termination of personal exemptions, increased estate and tax exemption, and retention of the QBI deduction.

• Tax Brackets: The lowest bracket is retained at 10% with the highest bracket still at 37%. The income amounts for the 10%, 12%, and 22% brackets receive an additional year of inflation adjustment.

• Personal Exemptions: The deduction for personal exemptions is permanently terminated. However, the law includes a temporary deduction of $6,000, through the 2028 calendar year, for individuals 65 years old and older. This deduction is phased out for seniors with modified adjusted gross income over $75,000 ($150,000 for those filing a joint return).

• Standard Deduction: The OBBBA retains the increased standard deduction. Further, the inflation-adjusted standard deduction increased for 2025 to $31,500 (joint filers), $23,625 (head of household), and $15,750 (all other filers).

• SALT Cap: The maximum itemized deduction for state/local taxes (also including property and vehicle taxes) has been expanded from $10,000 to $40,000 and is now indexed for inflation. There is a reduction for taxpayers with modified adjusted gross income exceeding $500,000, but not to be reduced below $10,000 (or $5,000 for those that are married filing separately). The $40,000 limit is temporary and will revert to the original $10,000 cap beginning in tax year 2030 – regardless of income level.

• Charitable Contributions: Beginning in 2026, non-itemizers will receive a maximum of $1,000 deduction ($2,000 for joint returns) for qualified contributions. For itemizers, the deduction will only be allowed if total contributions are more than 0.5% of adjusted gross income for the taxable year.

• 1099 Reporting: Effective starting with tax year 2026, the threshold for reporting payments to certain persons engaged in a trade/business and payments for services (Form 1099 MISC or NEC) has been raised from $600 to $2,000, to be indexed for inflation. Form 1099-K, which reports third-party network transaction income from settlement organizations (i.e. Paypal, Venmo), was originally scheduled to reduce its reporting threshold to aggregate payments exceeding $600 per payee, regardless of the number of  transactions. With the passing of OBBBA, the reporting threshold has increased to aggregate payments exceeding $20,000 per payee on more than 200 separate transactions in a tax period.

• Qualified Business Income (QBI): The new law keeps the QBI deduction at 20%, makes the deduction permanent and adds a new minimum $400 deduction for taxpayers with at least $1,000 of QBI.

• Education Accounts: 529 education savings plan withdrawals have been expanded from $10,000 to $20,000 per year for eligible K-12 qualified expenses. The law has expanded the definition of qualified expenses to include certain non-tuition costs, including online educational materials and tutoring outside the house.

• Savings Program for Children: A new savings program has been created called “Money Accounts for Growth and Advancement” (MAGA), which can also be used for saving for a child’s education. Under the new law, up to $5,000 annually can be contributed to a MAGA account. For a child born between January 1, 2025, and January 1, 2029, the federal government will contribute a one-time amount of $1,000 to the account. Parents and relatives can both contribute to the savings account and the funds will grow tax- deferred until the child reaches age 18. Funds can be used for higher education, small business startup costs, or first-time homebuyer expenses, with withdrawals taxed at the long-term capital gains rate for qualified expenses. Non-qualified withdrawals are taxed as ordinary income with penalties. Any unused funds could be withdrawn for any reason after age 30.

• Child Tax Credit: The bill makes permanent the increased child credit (and income phase-out). Further, the law increases the credit to $2,200 starting with the 2025 tax year, with an inflation adjustment for subsequent years. A social security number of at least one spouse is required to be included on a joint return to claim the credit. The child(s) social security number is also now required.

• Clean Energy Credits: OBBBA accelerates the termination of many clean energy tax incentives including those for primary residences, commercial property, and new/used clean vehicles for personal and commercial use. Termination dates range from September 30, 2025, to December 31, 2027, with the residential clean energy credit, energy-efficient home improvement credit, and new/used clean vehicle credits terminated by year-end 2025.

• Estate Tax: The bill retains the estate and gift tax exemption significantly increased by the TCJA. Starting in 2025 (and adjusting for inflation going forward), the exemption is $15 million for individuals and $30 million for married filing jointly. The portability election for surviving spouse is still in effect.

• Capital Investment Expensing: OBBBA increases the maximum amount a taxpayer may expense under Section 179 to $2.5 million, reduced by the amount by which the cost of qualifying property exceeds $4 million. Bonus depreciation is permanently extended, with the allowance increased to 100% for property acquired and placed in service after January 19, 2025.

• Qualified Opportunity Zones (QOZs): The incentive program created during TCJA has been made permanent and is also expanded with the initial QOZ program set to expire after December 31, 2026. The initial – and also newly created second program set to take effect in January 2027 – offer a 10-year rolling investment and provide investors with tax benefits for investing their unrealized capital gains into eligible distressed communities. Benefits include a temporary deferral on taxes, a step-up in basis of 10% if the QOZ investment is held for 5 years, and for investments held for at least 10 years – taxpayers receive a permanent exclusion of taxable income on gains resulting from their original investment.

For additional OBBBA information, check out this handy guide created by the Tax Accounting Group, which outlines key tax law changes for both individuals and businesses.

Sources: Duane Morris, Economic Innovation Group, Jackson Lewis, JDSupra, Keiter, Kiplinger, Michigan Chamber of Commerce, Reuters, Tax Foundation, USA Today

Securities offered through registered representatives of The Strategic Financial Alliance, Inc. (SFA), member FINRA, SIPC. Advisory services offered through registered investment adviser representatives of Strategic Blueprint LLC. SFA and Strategic Blueprint are affiliated through common ownership but otherwise unaffiliated with GenCrest Capital Partners. SFA and Strategic Blueprint do not give tax or legal advice.

Our very own Ashley Madden is featured in this month’s O’Henry Magazine. Click the headline to read the full article.