Author Archive

Embracing the Paradox of Uncertainty: Wealth, Resilience, and the Wisdom to Navigate Change

“The desire for security and the feeling of insecurity are the same thing.”

– Alan Watts

Affluent American families are increasingly confronting difficult questions as the nation’s global position shifts. The familiar sense of geopolitical and economic certainty is giving way to a more fluid, fragmented world. This unease is not merely emotional—it reflects structural changes long forecast by experienced observers such as Ray Dalio, founder of Bridgewater Associates. In his widely followed analyses of the “Changing World Order,” Dalio maps out how declining empires, rising powers, and cycles of debt and conflict shape the global landscape.

For many families, these aren’t abstract concepts. They are real, immediate, and pressing.

Strategy Provides Structure, But Mindset Drives Resilience

At Bespoke, we support families as they respond to this new era with thoughtful and flexible approaches. We help them design:

  • Investment strategies in hard assets, stable currencies, and globally resilient companies.
  • Estate structures that protect assets and privacy, and enable global custody.
  • Citizenship diversification, including investments that support multiple passports.

These tools are powerful. They provide a sense of agency in uncertain conditions. Yet even when a family is well-positioned structurally, a deeper unease can persist. That discomfort is not a flaw—it’s a signal. Once the tactical decisions are made, more fundamental questions often emerge. What is our role in this new world? What are we trying to preserve? And for whom?

The Role of Discomfort in Strategic Clarity

Alan Watts, a 20th-century philosopher, suggested that our desire for security may itself be the root of our anxiety. True peace, he argued, does not come from eliminating uncertainty, but from learning to live well within it. This insight has become particularly relevant for families stewarding generational wealth.

In our experience, resilience is not simply about predicting the future or defending against risk. It is about cultivating the capacity to engage uncertainty with discipline and openness.

Imagine a family that owns a historic ranch in Montana. News breaks that the government may sell nearby public land. A traditional response might involve immediate legal challenges or a decision to sell. But pausing—allowing space to explore the situation more deeply—might yield something far more valuable. Perhaps a philanthropic land trust emerges, or a regenerative agriculture partnership. What initially felt like a threat may reveal a powerful opportunity for stewardship and leadership.

This is the difference between reacting quickly and responding wisely.

Wealth as a Compass, Not Just a Shield

At Bespoke, we believe wealth should serve not only as a buffer from volatility but as a directional tool. It allows our clients to remain open, to explore different paths, and to lead with intention. This shift from control to curiosity is subtle but transformative.

We encourage families to adopt frameworks that reflect this mindset:

  • Dynamic scenario planning, not rigid predictions.
  • Trust structures with guardrails, not cages.
  • Global mobility, paired with grounded presence.
  • Investment frameworks that reflect values, not just returns.

These are not only tactical choices. They are reflections of a deeper orientation toward complexity—an acknowledgment that certainty is often an illusion, and that strength lies in adaptability.

Preparing for the Unknown

In a time defined by disruption, the families who flourish will not be the ones who chase clarity at all costs. They will be the ones who invest in the capacity to move through ambiguity with clarity of purpose and strength of character.

Security is not about knowing what comes next. It is about knowing you are prepared to meet whatever comes, with courage, insight, and a trusted structure of support.


If you’re interested in learning more about Bespoke’s approach to private wealth management and how we can help you build a secure financial future, we invite you to reach out to us directly. We’d be happy to set up a confidential consultation at your convenience.

Thank you for considering Bespoke as your partner in wealth management. We look forward to the opportunity to work with you.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.

Global Markets at a Crossroads: Why International Equities, Bitcoin, and Private Equity Are Reshaping the Landscape

In recent months, global markets have entered a period of significant divergence. U.S. equities, long the bellwether of global investor sentiment, are struggling under the weight of high valuations and policy uncertainty. In contrast, international equities have shown surprising resilience. Meanwhile, Bitcoin is stepping out of its speculative shadow, and private equity is confronting a long-overdue reckoning. These three themes—international outperformance, digital hard assets, and illiquidity risk—are reshaping how we think about asset allocation in the years ahead.

International Outperformance: A Quiet Shift Takes Hold

One of the most underappreciated developments in 2024 has been the strength of international equities. While U.S. indices such as the S&P 500 have dipped into negative territory, markets like the Hang Seng Index in Hong Kong and the DAX in Germany have remained in solid uptrends. These international indices have weathered the volatility with far greater composure than their U.S. counterparts.

This divergence is not just about market momentum. It reflects deeper structural dynamics: a weakening U.S. dollar, more favorable valuations abroad, and a relative lack of exposure to the large-cap tech names that dominate and increasingly weigh on U.S. benchmarks. In this environment, our approach has been to reduce exposure to broad U.S. indices and reallocate incrementally toward international opportunities—particularly in markets with strong trendlines, solid fundamentals, and better risk/reward setups.

Investors tend to overweight their home markets, but global leadership rotates. With many U.S. equities stretched and speculative fervor concentrated in a narrow slice of tech stocks, international diversification isn’t just prudent—it may well be necessary.

Bitcoin: From Toy to Treasury Asset

While the broader market has been under pressure, Bitcoin has quietly made historic gains. The digital currency recently hit an all-time high when measured against equities, signaling a structural shift in how it is perceived.

Bitcoin is no longer just a speculative playground for tech-savvy traders. It is increasingly acting like a digital counterpart to gold: a decentralized, non-sovereign store of value. Amid global monetary uncertainty and rising concerns about fiat debasement, the case for Bitcoin as a strategic asset allocation tool has grown stronger.

Price action confirms this shift. Bitcoin is breaking out not just in dollar terms, but relative to traditional assets like stocks. This breakout from a long base pattern suggests the beginning of a new structural uptrend. It doesn’t mean Bitcoin is without risk—volatility remains high—but the asset is showing signs of maturation. For investors willing to tolerate drawdowns in exchange for asymmetric upside, Bitcoin has become increasingly difficult to ignore.

Private Equity: A Liquidity Reckoning Unfolds

If Bitcoin represents a new frontier, private equity is a cautionary tale. After a decade and a half of exuberant inflows, the private market ecosystem is showing signs of strain. Endowments and large institutions are quietly exploring secondary sales. Discounts are widening. Illiquidity—once sold as a feature—is now looking more like a bug.

The core issue is twofold. First, the promise of an “illiquidity premium” has not materialized for many investors. Returns have lagged, and recent IPOs of private equity-backed companies have underwhelmed. Second, in an environment of rising uncertainty and shifting priorities, being locked into opaque and inflexible structures is increasingly unattractive.

What we are witnessing is the start of a broader reassessment. Liquidity, once taken for granted, is being revalued. Investors are recognizing the importance of being able to adapt, pivot, and access capital when it matters most. This is especially critical in a world marked by geopolitical shifts, technological disruption, and policy unpredictability.

Our view has been to emphasize a barbell approach: favor public, liquid markets where price discovery and flexibility are real, while reserving private allocations for only the most compelling, early-stage opportunities—where idiosyncratic returns justify the trade-off. The days of blindly allocating to mega-fund buyouts and late-stage private credit are, in our view, numbered.

The Road Ahead: Rethinking Risk and Reward

The investment world is changing. The old playbook—which prioritized U.S. dominance, low volatility, and institutional orthodoxy—is no longer sufficient. Today’s conditions demand new thinking.

International markets are quietly asserting leadership. Bitcoin is maturing into a meaningful strategic asset. And the cracks in the private equity model are becoming too large to ignore.

It’s not about abandoning tradition, but rather updating assumptions. Flexibility, liquidity, and diversification—real diversification—are taking center stage. And for investors willing to step back and reassess, this period of transition offers rare opportunities to get ahead of the next structural cycle.


If you’re interested in learning more about Bespoke’s approach to private wealth management and how we can help you build a secure financial future, we invite you to reach out to us directly. We’d be happy to set up a confidential consultation at your convenience.

Thank you for considering Bespoke as your partner in wealth management. We look forward to the opportunity to work with you.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.

How to Structure Your Charitable Giving

In the previous article, “How to Align Passion with Impactful Giving“, we discussed the fundamental aspects of philanthropic giving. In this article, we take a closer look at the different ways to structure charitable gifts and the advantages of each structure. We’ll start by discussing the role of foundations.

Conduit and Operating Foundations

Private foundations provide many of the same benefits of public charities if they are structured and administered as a conduit foundation or as an operating foundation.

A conduit foundation must distribute 100% of all property contributed to it before the end of the first quarter in the year following the contribution. For example, if you contributed $1,000,000 to a conduit foundation in 2024, the foundation would have to distribute that entire amount by April 15, 2025. Conduit foundations generally only make sense for benefactors who do not want to be directly involved in ongoing charitable activities, and who have several known public charities to which they want to distribute large amounts.

By contrast, an operating foundation does not just award grants; it is actively engaged in providing services that advance the tax-exempt purposes of the foundation. Although operating foundations require higher administrative commitment and overhead, they provide more beneficial charitable deduction opportunities for donors as well as additional flexibility and control. Private operating foundations may also create opportunities for family members to receive reasonable compensation for services they provide to the foundation.

The classification of a private foundation is determined on a year-by-year basis based on the foundation’s activities. In some years a foundation may be treated purely as a “private non-operating foundation” subject to the lower deduction limits and excise tax mentioned above. In other years the private foundation may be managed as a “conduit foundation” if it meets the 100% distribution test. And in other years it may qualify as a “private operating foundation” if it meets a specific two-prong qualification test discussed below. The key is to strategically manage the foundation’s investments and activities in a way that allows it to qualify as an operating foundation – at least in years that are most advantageous.

Private Operating Foundations

The most complex type of private foundation is a private operating foundation. If a private foundation satisfies both parts of a two-prong qualification test, it will be deemed to be an operating foundation. The first prong of the test is a mandatory income test that requires the foundation to spend at least 85% of the lesser of the foundation’s (1) adjusted net income (which does not include long-term capital gain income or contributions made to the foundation) or (2) its minimum investment return, on the “active conduct” of charitable activities. If the foundation does not meet the income test in a given year, it will not be treated as an operating foundation for that year regardless of any other test.

If the income test is met, then the foundation must also satisfy at least one of the following additional tests:

  • Assets test – At least 65% of the foundation’s assets are devoted to the direct conduct of tax-exempt activities; or
  • Endowment test – The foundation distributes at least 2/3 of its minimum investment return in the active conduct of its tax-exempt activities.

The foundation may meet the assets test in some years, and the endowment test in other years. It must meet the income test every year. In each prong of the qualification test, expenditures and distributions must be made in ways that advance the exempt activities of the foundation itself, rather than through grants to other individuals or organizations.

Defining “Active Conduct” for the Qualification Test

The following are general examples of expenditures and grants that may qualify as “active conduct:”

  • Amounts paid or set aside to acquire or maintain assets used directly in the foundation’s exempt activities.
  • Reasonable administrative expenses such as salaries, travel expenses, and other operating costs necessary to conduct the foundation’s exempt activities.
  • Grants made as part of an active program in the foundation.
  • Grants made with continuing supervision by the foundation (and with the grant recipient reporting back to the foundation).
  • Tax on an operating foundation’s net investment income may be treated as a qualifying distribution.

By contrast, administrative expenses and operating costs that do not directly advance the foundation’s tax-exempt purposes do not constitute qualifying distributions.

As the above discussion demonstrates, private operating foundations are complex, but where you wish to fund a cause that is not being adequately addressed by other existing charities, a private operating foundation may be your best choice.

Private Non-Operating Foundations

A private non-operating foundation is a charity that primarily functions as a grant-making entity; i.e., it primarily makes grants to other charities rather than conducting its own operations. Like operating foundations, non-operating foundations are typically funded by an individual or single family.

Private non-operating foundations must annually distribute at least 5% of their net investment assets for charitable purposes, and their investment income is subject to a 2% excise tax. Moreover, when funding a non-operating foundation, you can deduct up to only 30% of your adjusted gross income for cash contributions, 20% for non-cash contributions (e.g., appreciated stock). Significantly, you can carry forward unused deductions for up to five additional years (i.e., six years total). Conversely, with a contribution to a conduit or operating foundation (or any direct contribution to a public charity), you can deduct up to only 50% of your adjusted gross income for cash contributions, 30% for non-cash contributions.

Donor Advised Funds

A popular alternative to non-operating foundations is the Donor Advised Fund (DAF). DAFs are separately identified accounts maintained and operated by public charities, known as sponsoring organizations. Once the donor makes the contribution, the sponsoring organization has legal control over it. However, the donor, or the donor’s representative, retains advisory privileges with respect to the distribution of funds and the investment of assets in the account. Significantly, the donor requests that the sponsoring organization make a distribution, but the sponsoring organization retains the right to deny that request.

DAF assets can be invested and grow tax-free, potentially increasing the amount available for charitable grants. With a DAF, the donor receives an upfront charitable deduction for the amount contributed to the DAF (using the higher deductibility limits), even though the funds may not be distributed to charity for some time. In fact, this benefit has caused DAFs to recently come under scrutiny in Congress, with recent proposals requiring a minimum annual payout and maximum term before all funds must be distributed to charity.

Benefits of Giving Appreciated Assets

Donating appreciated assets, such as marketable securities, provides unique benefits to both the donor and the receiving charity. With a contribution of marketable securities, you will receive a tax deduction for the current fair market value of the stock and any public charity can easily sell the stock, convert it to cash, and not pay any tax. By donating the marketable security itself, as opposed to selling the security and donating cash, the donor may avoid capital gains tax on the sale of the security and receive a charitable deduction, while the charity receives the full value of the security.

Structures for Making Charitable Gifts

As discussed above, a Donor Advised Fund is one structure through which charitable contributions can be made but it may have some limitations. Some DAF sponsoring organizations permit the contribution of other types of appreciated assets, such as real estate or digital assets such as bitcoin. However, not all sponsoring organizations will accept these assets, and with few exceptions, most DAFs will require the sale of these assets upon contribution. Thus, it is imperative that you communicate with the DAF sponsoring organization to ensure it will accept the asset(s) you wish to contribute and/or, that it will hold the appreciated assets for some future sale date.

Capital Gains Deferral Trust

Rather than giving appreciated assets directly to a charity or DAF, another option is to give those assets to a specific type of charitable trust, recognized and accepted by the IRS, that can then sell the assets and not pay the tax. As a result, the full value of the appreciated assets can then be invested.

The trust then pays a fixed percentage, typically to you and/or your spouse for life, based upon the value contributed. At the end of that term, the remaining balance is paid to the charity or charities of your choice.

With this strategy you receive an income tax deduction for the present value of the hypothetical amount going to charity, and the assets are protected from your creditors and are outside of your estate for purposes of the estate tax. This is an excellent way to give to charity in the future, while providing you a tax-deferred income stream now.

For example, suppose as a Colorado resident you own Microsoft stock worth $1 million with zero tax basis. Thus, if you sold the stock today, you would pay $200,000 in federal capital gains tax (20%) and $43,300 in Colorado capital gains tax (4.33%), netting you $756,700. (In all likelihood, the net investment income tax would also apply, further reducing your net by 3.8%.)

If instead you transferred the stock to this type of tax-deferral trust, the trust would sell the stock and have $1 million to invest. There are several options but with the most common type, the trust would pay you (and your spouse, if any) a fixed annuity (say 5%) for your lives. Thus, you would receive $50,000 per year for the rest of your lifetimes(s), subject to tax.

Annuity to Charity Trust

Another option is to contribute assets to a different type of charitable trust–one that pays an annuity to charity for a specified number of years and then transfers the remaining trust balance to your heirs.

This type of trust is perfect to establish a long-term charitable giving strategy during your lifetime (for example, if you want to contribute $x to your favorite charity for the next 20 years).

And under certain circumstances, this trust can even provide you with an upfront income tax deduction for the present value of the annuities paid to charity. Additionally, assets within this type of irrevocable trust are protected from creditors and free of gift or estate tax.

Distributions Directly from Your IRA

If you are over 70 1/2, you can distribute directly to charity up to $100,000 per year from your IRA or qualified plan. This reduces or eliminates your required minimum distribution by the amount of the direct charitable contribution (up to $100,000) and, significantly, removes the direct charitable contribution from that year’s taxable income, thereby reducing your taxable income by the amount of the direct distribution to charity, up to $100,000. For example, if your required minimum distribution is $85,000, rather than taking that distribution and turning around and making a cash contribution to charity, consider making the distribution directly from your IRA. By making a direct contribution from your IRA, the $85,000 will not be included in your taxable income, thus reducing your overall taxable income.

Conclusion

Charitable giving is a dynamic process with many different strategies that can be levered to achieve a lasting impact and bring additional meaning to your legacy. The Bespoke Group provides strategic guidance at every step—helping you craft a personalized giving strategy that reflects your values, ideals, and passions. We work closely with you to ensure your philanthropy drives meaningful impact in the areas that matter most.


If you’re interested in learning more about Bespoke’s approach to private wealth management and how we can help you build a secure financial future, we invite you to reach out to us directly. We’d be happy to set up a confidential consultation at your convenience.

Thank you for considering Bespoke as your partner in wealth management. We look forward to the opportunity to work with you.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.

How to Align Passion with Impactful Giving

The most meaningful philanthropy starts with a clear ‘why.’ For wealth holders, aligning giving with personal values and long-term vision is essential— not optional. This two-part series offers a blueprint for effective, values-driven philanthropy. In this first installment, we help you define what matters and where to begin. The second, “How to Structure Your Charitable Giving“, will provide a more detailed outline of various types of giving structures and alternative assets that can be gifted.

Identify Your Passion Causes

Some individuals come to us with fully formed views on philanthropy. Others have no idea how they should start their philanthropic journey. For this latter group in particular, the conversation often starts with the following question:

“Assuming a perfect world without limitation, what causes are you passionate about?”

Once you’ve defined these core causes, the question then becomes, “how can you best connect your philanthropy to these causes?”

Unsurprisingly, many individuals have limiting beliefs about their ability to make an impact on the causes they care about. These beliefs include thoughts like: my cause is too large or, conversely, my cause is too small; I don’t have the resources to impact my cause; my cause is too difficult to impact; impacting my cause requires disclosing my identity; etc.

In some cases, these limiting beliefs may reflect objective challenges, but more often, they are based on subjective perceptions. For example, one of our clients is deeply passionate about addressing racial and gender inequality, two massive issues that seem insurmountable, even with unlimited resources. However, through several conversations with various experts, the client learned that human trafficking is a socio-economic issue that disproportionately impacts women and people of color. This insight lead the client to address human trafficking in a particular region close to home by funding a center for victims of human trafficking. Today, that center serves a significant numbers of victims daily, making a meaningful impact on the community.

Another client couple is passionate about their church, a relatively small denomination with diocese in only a handful of U.S. cities. Given the small size of this church, the clients require absolute anonymity in making large contributions to their church. Through the assistance of a philanthropy consultant, we ensured total anonymity with their contributions. Further, after numerous conversations we determined that multiple smaller contributions over many years would likely have a much greater impact than a fewer number of large contributions, given the relatively small size of the endowment – and vision – of the church.

Once we align the client’s passion causes with potential philanthropy, we then explore the many ways in which the client can approach that philanthropy from a structural perspective. The first question is, are there charities that are addressing this cause, or does the client need to create a charity to address it? From there, we discuss various types of private foundations and their best use case to fit the client’s objectives.

Private Foundations Generally

At the risk of oversimplifying, there are three general classifications of private foundations: 1) private non-conduit, non-operating foundations, 2) private “conduit” foundations, and 3) private operating foundations. Of these, conduit and operating foundations enjoy many of the same benefits that public charities provide. Non-operating, non-conduit private foundations provide lower levels of deductibility and are subject to additional layers of tax at the entity level.

Private foundations are an excellent tool for managing the family’s philanthropy and incorporating younger family members into family wealth decision making. It should be noted, however, that private foundations are complex with significant regulations and administrative costs, and they are therefore not right for every family.

Ways to Give: Cash and Appreciated Asset Contributions

Cash contributions provide the immediate liquidity to fund charitable operations and thus are vital to many charities. Cash contributions also provide the highest level of deductibility against your adjusted gross income. However, there are other ways you can give . . . which may be advantageous to you from a tax perspective and may allow you to incorporate giving to your passion causes as part of your estate planning.

Rather than donating cash or a check, consider contributing appreciated assets such as marketable securities, which include stocks, bonds or certificates of deposit. Contributing appreciated assets provides additional flexibility and tax advantages when implemented within the correct structure.

Conclusion

A meaningful philanthropic journey begins with clarity of purpose—identifying the causes that matter most and aligning them with a strategy for impact. From there, the focus shifts to execution: how to channel resources effectively, and which vehicles— whether foundations, trusts, or donor-advised funds— are best suited to achieve that impact. This is typically an iterative process that sometimes takes place over many conversations, often over several months or longer. Further, one’s philanthropy is not static and may evolve and/or expand over time.

In this way, philanthropy can not only produce a significant impact, but it can provide tremendous meaning to those who engage in it. Many of our clients find unending joy knowing that they are truly making a difference. At The Bespoke Group, we take great pride in helping individuals and families find this joy.

If you’re interested in learning more, please read “How to Structure Your Charitable Giving” where we break down different types of foundations and trust structures, and how to identify what structure will best serve your values and philanthropic goals.


If you’re interested in learning more about Bespoke’s approach to private wealth management and how we can help you build a secure financial future, we invite you to reach out to us directly. We’d be happy to set up a confidential consultation at your convenience.

Thank you for considering Bespoke as your partner in wealth management. We look forward to the opportunity to work with you.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.

Trump’s Trade War: What Investors Need to Know About Tariffs, Market Volatility & Geopolitics

Authored by Jacob Shapiro, Head of Geopolitical & Macro Research and Senior Client Relationship Manager at Bespoke Group

I know how worried the average person is about market volatility and geopolitical issues when random people in my life ask me some version of, “So what do you think is going to happen?” This morning, I was at my daughter’s school, where I thrilled her class with a riveting reading of The Serious Goose. Afterwards, I helped her build a castle made of blocks whilst wearing a tiara — as one does. While we were building, a teacher started asking me about my opinions on President Trump’s tariff policy and the impact it was having on retirement accounts.

The average person’s worried index is extremely high.

Is the Trump Administration Bluffing?

Open a news website, turn on television news, or — if you are truly brave — hop on social media, and you are greeted with doom and gloom: comparisons of recent market performance to the pandemic, the 2008 Great Financial Crisis, and even the Great Depression. These comparisons are not unreasonable, especially those to the Great Depression, which was likely made worse and longer by the 1930 Smoot-Hawley Tariff Act. If the Trump administration doubles down on its global trade war, the current market drawdown may appear in retrospect to be the early innings of a much longer game.

Which is why I continue to think the Trump administration is bluffing. The comparison is a legitimate one. The Trump administration does not want people like you to think that — it wants the world to take its tariff threats with deadly seriousness. When Kevin Hassett, the Director of the National Economic Council, posted on social media that President Trump was considering a 90-day tariff pause, the White House wasted no time shouting down the assertion as “fake news.” (Hassett has since deleted the post.) But if President Trump doubles down, what awaits him is an economic depression, a bloodbath in the midterms, and an ignominious place in U.S. history books.

At a certain point, it does not matter whether President Trump is bluffing or not. The haphazard, lazy, and mercurial (I use these descriptors objectively, not pejoratively) way the Trump administration’s tariff policy has been rolled out has already cast the dice: Any country that can lessen its dependence on the United States will do so — whether Trump walks back the tariffs or not.

Not all countries can do so. Mexico is celebrating that it wasn’t included on “Liberation Day” because the country remains, as Porfirio Díaz once said, “So far from God, so close to the United States.” Canada still has some reckoning to do. Japan has already reached out to the U.S. and agreed to cabinet-level tariff negotiations. But other countries — like China and Brazil, or the European states that make up the EU — will not take this medicine. They will self-amputate and enroll in physical therapy.

Key Data Points to Consider

Amidst the chaos, there are a few key data points to keep in mind:

From Reuters: “The European Union wants India to eliminate tariffs on car imports under a long-pending trade deal, and Prime Minister Narendra Modi’s government is willing to sweeten its current proposal to seal the talks… ‘The EU has come back asking for a better deal, and India wants to make a better offer,’ said one of the industry sources.” The EU is not turning back. It is embracing a multipolar world and pivoting quickly to establish better trading relations with potential markets.

Also from Reuters: “Several powerful Iranian-backed militia groups in Iraq are prepared to disarm for the first time to avert the threat of an escalating conflict with the U.S. Trump administration.” This comes on the heels of President Trump agreeing in principle to indirect talks with Iran in Oman over its nuclear program. President Trump likely wants to make a deal with Iran rather than start a war in the Persian Gulf.

China has taken off the gloves — retaliating with 34 percent reciprocal tariffs, potentially dumping U.S. Treasuries, devaluing its currency, front-loading fiscal stimulus, and exhorting its people to “focus on doing your own thing.” But according to one commentator writing in The People’s Daily: “The sky will not fall,” and more importantly, China “did not close the door to negotiations with the U.S.” China had four years to prepare for a Trump presidency. It is ready for even higher tariffs than what have been announced… but it is also ready to make a deal with the Trump administration when the White House is ready.

Market Movements and What Lies Ahead

As I type this in the early afternoon of April 7th, the S&P 500 and the Nasdaq are back in positive territory. Bitcoin has pared its losses and is approaching $80,000. The yield on the 10-year Treasury is rising and closing in on 4.2 percent. The dollar is also climbing from its Liberation Day nadir. What happens next depends on the whims of a single man in the White House. If he doubles down on tariffs, the bottom could fall out. If something like the 90-day negotiation reprieve happens, a whipsaw is possible — or even renewed market confidence. My horoscope says it is crucial that I stand up and be a deciding force. It has as much predictive value as anything else in this paragraph.

Geopolitical methodology rejects thinking in such short time periods. I have no insights into what President Donald Trump is feeling or thinking about doing next. I have no one-size-fits-all strategy for my daughter’s teacher or for whoever is reading this. The short term promises to be volatile, unpredictable, and messy — and just how messy depends entirely on the decisions of a single person, which means there is an impossibly huge degree of variance in what is going to happen next.

The Long-Term Outlook

The long term, however, is clear — indeed, becoming clearer by the day. The U.S. will abdicate its role as leader and protector of a globalizing world. Supply chains, trading relationships, and alliances will be upended and remade. The U.S. will remain a powerful, wealthy, and influential country in the world… but global companies that profited from globalization will suffer, and the status of the U.S. dollar and U.S. Treasuries as safe havens will erode. It will be a time of national champions, of vertical integration, of technological and military competition, of scrambles for resources, markets, and advantage.

In other words, it will look a lot like the world usually looks when there isn’t a global hegemon — which has only happened twice in all history: the British Empire in the 19th century and the U.S. between 1990 and 2025. It is a reversion to the geopolitical mean. One can be forgiven for a sense of whiplash — the human mind is not hardwired to accept change easily, and multiple generations have grown accustomed to the present. But the geopolitics that is unfolding for all to see is not the aberration.

That was the last 35 years.

If you’re interested in learning more about Bespoke’s approach to private wealth management and how we can help you build a secure financial future, we invite you to reach out to us directly. We’d be happy to set up a confidential consultation at your convenience.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.

Corporate Transparency Act Update: What to do now?

Updated March 3, 2025

Businesses and professionals are scrambling to keep up with the shifting legal landscape as the Corporate Transparency Act (CTA) undergoes significant – i.e., multiple on again, off again – changes. It appears that the CTA is now permanently off as a result of a March 2, 2025, Treasury Department announcement saying Treasury would not enforce the CTA except as to foreign reporting companies (i.e., non-U.S. business entities that are registered to do business with any U.S. Secretary of State). 

What is The Corporate Transparency Act?

The CTA was passed into law as part of the National Defense Authorization Act for Fiscal Year 2021. The CTA requires most U.S. and some foreign business entities to report their “beneficial owners” to the Financial Crimes Enforcement Network (FinCEN) for the purpose of combating money laundering and terrorism financing; if the business entity is registered with any U.S. Secretary of State or similar agency, it is considered a “reporting company” and likely must file a beneficial owner information report (BOIR) with FinCEN. If a beneficial owner’s information changes, the reporting company must file an updated report with the new information.

Significantly, foreign and domestic business entities that are not registered with any U.S. Secretary of State’s office are not considered reporting companies and are not subject to the reporting requirements of the CTA.

Reporting Companies and Their Obligations

Reporting companies created before January 1, 2024, originally had until December 31, 2024, to report their beneficial owners, but effective January 1, 2024, new reporting companies were required to file within 45 days of the creation of the reporting company by the original filing with a Secretary of State. According to FinCEN’s FAQs, any person who willfully violates the CTA’s reporting requirements may be subject to civil penalties of up to $500 (indexed for inflation) for each day that the violation continues. A person who willfully violates these reporting requirements may also be subject to criminal penalties of up to two years imprisonment and a fine of up to $10,000. Potential violations include willfully failing to file a beneficial ownership information report, willfully filing false beneficial ownership information, or willfully failing to correct or update previously reported beneficial ownership information.

However, via Press Release dated March 2, 2025, the Treasury Department announced that it will not enforce the CTA except as to foreign reporting companies (i.e., non-U.S. companies that register with a U.S. Secretary of State).

Determining Beneficial Owners & Reporting Requirements for Different Entities

As to determining beneficial owners, a reporting company must report the individuals who either (1) exercise substantial control over the reporting company or (2) own or control at least 25 percent of the ownership interests in the reporting company.

Those who exercise substantial control over the reporting company are those individuals who are a senior officer (e.g., the company’s president, chief financial officer, general counsel, chief executive officer, chief operating officer, or any other officer who performs a similar function), those who have authority to appoint or remove certain officers or a majority of directors (or similar body) of the reporting company, and the important decision-makers for the reporting company. According to FinCEN’s FAQs, important decisions “include decisions about a reporting company’s business, finances, and structure. An individual that directs, determines, or has substantial influence over these important decisions exercises substantial control over a reporting company.” Thus, a reporting company must include as beneficial owners its Managers if an LLC, its general partners if a limited partnership, and its President or CEO and CFO, CLO, etc. if the reporting company is a corporation.

If the reporting company is owned at least 25% by another reporting company, the report must include all of the owner reporting company’s beneficial owners in its report. Alternatively, the report may include the owner’s FinCEN identifier, which includes all of its beneficial owner information. If at least 25% of the reporting company is owned by a trust, the reporting company must report as beneficial owners the trust’s Trustee, the trust’s beneficiary (if there is only one beneficiary), and the trust’s settlor if the trust is a revocable trust. Learn more about how trusts are affected by the CTA here.

Corporate Transparency Act: Injunctions, Appeals Court, and Ongoing Enforcement Challenges

Since its passage into law, critics have argued that the CTA is unnecessary, given that much of this information is already collected elsewhere, and further, that the CTA is an unconstitutional infringement on the beneficial owners’ right to privacy.  Thus, numerous lawsuits have been filed nationally seeking to prevent enforcement of the CTA, and several lower courts have issued injunctions preventing such enforcement. One such case (Texas Top Cop Shop, Inc. v. McHenry—formerly, Texas Top Cop Shop v. Garland) was appealed all the way to the U.S. Supreme Court, where on January 23, 2025, the Court granted the government’s motion to stay the nationwide injunction issued by a federal judge in Texas. In other words, the Supreme Court ruled that FinCEN could proceed with CTA reporting enforcement.

However, on January 7, 2025, a second Texas court had also issued a national injunction in Smith, et al. v. U.S. Department of the Treasury, et al., on February 5, 2025, the Department of Justice—on behalf of the Department of the Treasury—filed a notice of appeal of the district court’s order and, in parallel, has sought to stay that order as the appeal proceeds. In a recent Alert, FinCEN indicated that it intends to enforce the CTA reporting requirement if the injunction is lifted in the Smith case:

“If the district court’s order is stayed, thereby allowing FinCEN’s Reporting Rule to come back into effect, FinCEN intends to extend the reporting deadline for all reporting companies 30 days from the date the stay is granted (emphasis added).”

Then, on February 18, 2025, the court in Smith stayed its injunction as a result of the Supreme Court’s ruling in Texas Top Cop Shop. Not surprisingly given FinCEN’s statement above, on February 19, 2025, FinCEN announced the commencement of the 30-day window to file such that for most reporting companies all initial, updated, and/or corrected beneficial ownership reports are due no later than March 21, 2025.

Thereafter, on February 27, 2025, FinCEN announced that it would NOT enforce the March 21, 2025, deadline and that it would issue further guidance by that same date.

Then, on March 2, 2025, the Treasury Department (which oversees FinCEN) issued a Press Release saying it would not “ … not enforce any penalties or fines against U.S. citizens or domestic reporting companies or their beneficial owners” and that it would be issuing new rules limiting the application of the CTA to foreign reporting companies. Thus, as of March 2, 2025, the CTA is off again unless the business entity is a foreign reporting company.

Corporate Transparency Act: How to File

Presuming that the reporting requirements will commence eventually, the best preparation for the filing of the FinCEN beneficial owner report is to obtain a FinCEN Identifier for all of the reporting company’s beneficial owners. The FinCEN FAQs explain this process succinctly:

“Individuals may request a FinCEN identifier … by completing an electronic web form at https://fincenid.fincen.gov. Individuals will need to provide their full legal name, date of birth, address, unique identifying number and issuing jurisdiction from an acceptable identification document, and an image of the identification document. After an individual submits this information, they will immediately receive a unique FinCEN identifier.”

Rather than providing all of the above information in the beneficial owner report, the reporting company need only provide the FinCEN identifier for each beneficial owner, thereby greatly simplifying the reporting process. Further, by using FinCEN identifiers, if a beneficial owner updates his or her FinCEN identifier information, that update will automatically apply to any reporting company’s report which includes that beneficial owner, thereby eliminating the reporting company’s duty to file an updated report.

To file a beneficial owner report, visit FinCEN’s CTA website at https://www.fincen.gov/boi and click on the “File a report using the BOI E-Filing System.” Note that the link to obtain a FinCEN identifier, discussed above, is immediately below.

Click on the link that reads “BOI E-Filing: Beneficial Ownership Information (BOI) Reporting, Get Started.” You now have the option to either complete and file the report in pdf (hardcopy format) or online electronically. There is no difference in the information requested – in fact, the pdf version is identical to the online form, although the pdf option gives you an easy record of your filing. Select the option that is most comfortable for you.  If you select the pdf option, it will download the pdf form. If you select the electronic option, you will be taken to a secure site that tracks the pdf form.

Either way, follow the prompts and complete the requested information. Under Part 1, Reporting Company Information, be sure to select “Request to Receive FinCEN Identifier (FinCEN ID)” for the reporting company, which will simplify filing updates in the future, if necessary.

For detailed, step-by-step filing instructions, visit https://boiefiling.fincen.gov/resources/BOIR_E-File_PDF_Step-by-Step_Instructions.pdf

We’ll continue to provide CTA updates as needed. For more information, visit the beneficial owner information page of FinCEN at https://www.fincen.gov/boi.

This article is intended for informational purposes only. The information shared reflects an evolving situation and does not represent a guarantee or prediction of future outcomes. The results described may not be typical or applicable to every client or situation, and individual results may vary based on a variety of factors. Any decisions made based on this information should be considered in the context of your specific circumstances and investment objectives. Please consult with your investment adviser for personalized advice.

The American Dream is Evolving: Diversifying Beyond Homeownership

In recent weeks, we’ve witnessed devastating fires raging through parts of California, leaving countless families facing the unimaginable. For many, their homes—long seen as the cornerstone of the American Dream—were reduced to ash. It’s a stark reminder that while homeownership is a worthy goal, it shouldn’t be the only focus of our financial journey.

As we move forward, it’s essential to ask ourselves: Are your assets truly protected? Are they diversified in ways that minimize risk? And perhaps most importantly, are you setting up a financial legacy that will ensure your children are well taken care of, no matter what challenges arise in the future?

The harsh reality is that we live in a world where natural catastrophes—like the hurricanes that have impacted Florida or the wildfires in California—are becoming more frequent. With the unpredictability of climate change, geopolitical shifts, and economic volatility, it’s more important than ever to take a proactive approach to your financial planning.

The Power of Diversification

While homeownership has long been a central pillar of financial success, it’s crucial to understand that wealth should be built on a foundation that includes a variety of assets. Diversification is one of the most powerful tools you can leverage to safeguard your wealth. By allocating assets across different investment vehicles—such as stocks, bonds, real estate, gold, Bitcoin, private credit, municipal bonds, and other assets globally you can manage your risk more effectively. This way, even if one sector or geography faces challenges, your broader portfolio remains strong.

Creative Solutions for Liquidity

It’s also important to pay attention to liquidity, but this doesn’t just mean having cash on hand. In fact, one of the most creative ways to address liquidity is by designing a portfolio that can solve for specific needs, such as income generation or funding yearly expenses for your estate. Liquidity is not just about immediate access to cash—it’s about building a portfolio that provides flexibility and access to resources when you need them most.

For example, you can strategically incorporate income-generating assets like private credit, municipal bonds, and dividend-paying stocks, all of which can provide consistent cash flow for ongoing expenses or emergencies. You can also create liquidity through the careful use of non-traditional assets like gold or cryptocurrency, which may be liquidated or converted to cash in times of need or in times of opportunity. Having liquidity means optionality. The key is to think creatively about how your investments can work together to create a comprehensive strategy that meets your cash flow needs while continuing to appreciate over time.

This approach goes beyond just thinking about the stock market or homeownership—two options that are often seen as the default. With the right balance of liquid and illiquid assets, you can build a portfolio that not only protects and compounds wealth but also provides the necessary liquidity to meet your financial goals and those of your heirs.

Protecting Your Legacy with Trusts

One of the most challenging aspects of natural disasters for parents is the worry about what will happen to their children if there is no house to pass down. The loss of a home can feel like the loss of a family legacy—something built with years of effort and sacrifice. But it’s important to remember that your legacy is not limited to real estate. There are many ways to ensure that your children are taken care of, even if a house is no longer part of the equation.

A well-structured trust can be an incredibly powerful tool for protecting your wealth, no matter the asset type. In fact, trusts can hold a wide variety of assets—ranging from real estate to stocks, bonds, gold, Bitcoin, private credit, and even business interests. By placing these assets into a trust, you can not only protect them from creditors, probate, and potential disputes, but you can also ensure that they are distributed according to your wishes.

This strategy allows you to create a legacy for your children and future generations, offering them financial security and peace of mind, no matter what happens to your home. Whether it’s an inheritance of diversified investments, income-generating assets, or other appreciating assets, a trust ensures that your legacy is preserved and protected.

Building Resilience Through Financial Well-Being

In times of uncertainty, it’s natural to feel anxious, especially when your home, your investments, and your future seem vulnerable. But just as we focus on mental well-being to build resilience and cope with stress, the same approach can be applied to our financial well-being. Money, after all, is one of the leading sources of anxiety for many people.

Building a resilient financial foundation—through diversified assets, trust structures, and strategic planning—can offer peace of mind in the face of adversity. It’s about creating a financial framework that supports you through life’s uncertainties, just like mental wellness strategies help us navigate emotional challenges. The more you can plan, diversify, and protect your wealth, the more resilient and confident you’ll feel, even when the unexpected happens.

Start the Conversation Today

The recent events in California and Florida remind us all of the importance of being prepared. If you’re ready to explore how diversification, trust structures, and other wealth-preserving strategies can help secure your financial future, we invite you to start a conversation with us.

Together, we can create a roadmap that not only helps protect your wealth but also gives you the freedom to focus on what truly matters—your family, your passions, and your legacy.

Let’s take the next step in your financial journey—one that goes beyond homeownership and secures a future built on strength, stability, and peace of mind.

If you’re interested in learning more about Bespoke’s approach to private wealth management and how we can help you build a secure financial future, we invite you to reach out to us directly. We’d be happy to set up a confidential consultation at your convenience.

Thank you for considering Bespoke as your partner in wealth management. We look forward to the opportunity to work with you.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.

Wealth Optimization Strategies for Bitcoiners with Will Foxley on The Mining Pod

On this episode of The Mining Pod, Bespoke’s Founder, Matthew McClintock, and Client Services and Trading Support Associate, Jack Jones, sit down with Will Foxley to discuss stock option wealth planning, BTC income planning, early estate planning, and much more. Watch the full video here.

Digital assets like Bitcoin and mining stocks can be part of a strategy aimed at potential growth and long-term wealth preservation, while helping to build a lasting legacy. Our family office and advisory service is tailored to help individuals manage their wealth responsibly, from optimizing tax strategies to designing custom trust structures aimed to preserve privacy and promote seamless asset transfer. This episode unpacks critical strategies like estate planning, charitable giving, and revocable trusts that help avoid probate, maintain privacy, and minimize tax burdens.

Financial Sovereignty Beyond Self-Custody

Achieving greater financial control goes beyond just holding your Bitcoin keys—it’s about preparing for the future with intention and a well-rounded strategy. Without a structured plan, unexpected events like illness or death can leave your loved ones navigating public, court-supervised processes. A trust offers a private, enforceable way to protect your assets and ensure your wishes are honored. At Bespoke Group, we help Bitcoiners create tailored strategies focused on preserving autonomy, privacy, and long term wealth, helping you navigate the complexities of digital assets beyond self-custody.

Strategic Custody Solutions

As Bitcoin’s value grows, so does the need for secure, well-planned custody. While “being your own bank” works for smaller holdings, large Bitcoin stacks require a more strategic approach to mitigate risks and ensure continuity. Bespoke helps Bitcoin holders implement cascading multisig setups and estate-focused trusts, balancing sovereignty with trusted oversight. Thoughtful planning can help secure your assets, minimize tax exposure, and support long-term wealth preservation, allowing you to maintain greater control over your financial future. 

Strategic Planning for Protecting Gains and Supporting Long-Term Wealth for Bitcoin Founders

Planning for Bitcoin equity gains and private company assets requires a flexible, forward-looking approach. Whether you’re holding founder stock, RSUs, or Bitcoin mining equity, it’s important to start with clear financial goals for the wealth you accumulate. If you plan to cash out and enhance your lifestyle, prioritize strategies for privacy and asset protection. But if your focus is on long-term family wealth, consider setting up a dynasty trust to shelter assets from estate taxes across generations.

For Bitcoin miners and similar ventures, strategy involves balancing rewards and equity gains. You’ll need to decide how much wealth to retain in the company versus what to distribute as personal income, which affects both taxes and reinvestment potential. Ultimately, define your end goal first. This sets a foundation to adapt your wealth strategy over time, ensuring that every decision aligns with your vision for the future.

Navigating the complexities of Bitcoin, equity gains, and estate planning requires a thoughtful strategic approach to help manage your assets effectively and support their transfer to future generations. At Bespoke Group, we specialize in helping individuals plan for the long-term, balancing financial sovereignty with trusted oversight. Whether you’re a Bitcoin holder, a founder with significant equity, or someone seeking to build generational wealth, our tailored strategies empower you to build a lasting legacy, minimize tax burdens, and achieve your financial goals with confidence.

This information is intended for general educational purposes only and should not be construed as legal or investment advice. Investing in digital assets such as Bitcoin and other cryptocurrencies involves significant risks, including volatility and potential loss of principal. Secure custody is an important part of a strategy, but it does not eliminate risks. These assets may not be suitable for all investors. Please carefully review your risk tolerance and consult a financial advisor before making any investment decisions.

The Potential Implications of the Corporate Transparency Act (“CTA”) on Individual Privacy

What is the Corporate Transparency Act?

On January 1, 2024, the Corporate Transparency Act (“CTA”) went into effect, requiring the U.S. Treasury Department’s Financial Crimes Enforcement Network (“FinCEN”) to collect beneficial ownership information (“BOI”) from corporations and limited liability companies (“LLCs”) registered in the U.S. 

A beneficial owner is an individual who, directly or indirectly, exercises substantial control over a “reporting company” or who owns or controls at least 25% of the ownership interests of the company. The mandatory disclosures include the individual’s full legal name, date of birth, address, and a unique identifying number such as an EIN or Social Security number, or an identification number issued by FinCEN. BOI information is reported through the Beneficial Ownership Secure System (“BOSS”), which is a “a non-public, secure registry” managed by FinCEN.

The cost of non-compliance can be highly punitive: Failure to disclose the required information to FinCEN may be subject to severe civil and criminal penalties, including a fine of up to $250,000 or imprisonment up to five years.

What is Considered a Reporting Company?

The CTA regulations apply to “reporting companies,” which are further delineated as Domestic and Foreign Reporting Companies. Virtually any company established by filing organizational documents with a Secretary of State of any U.S. state is a “reporting company” and is subject to the reporting requirements. Even single member or trust-owned LLCs created anywhere in the U.S. are subject to the disclosure rules.

Almost all U.S. domestic LLCs are Domestic Reporting Companies, even if they were only established for personal wealth structuring purposes.

A Foreign Reporting Company is an entity established outside the U.S. that is registered to do business with a Secretary of State (or equivalent office). Foreign companies that are not required to register to “do business” are NOT foreign reporting companies under the CTA regulations. Each state’s statutes and the rules enacted by the various secretaries of state determine what level of activity constitutes “doing business” in the state. If a particular locality does not require a foreign company to register to do business, it is not considered a Foreign Reporting Company under the CTA regulations.

How Are Trusts Affected by the CTA?

Importantly, trusts are not “reporting companies” and are not subject to the CTA disclosure rules. Of course, there are scores of different types of trusts and many attractive trust jurisdictions that may provide appropriate planning solutions. The tax characteristics, privacy, and protection offered by a trust depends entirely on the type of trust, where it’s established, and how it’s managed.

Planning for non-disclosure of beneficial owner information to the FinCEN database requires careful analysis to determine if the foreign entity is exempt from the disclosure rules or if a certain type of trust framework achieves broader wealth planning objectives. Clients who place a high premium on privacy and who wish to keep their personal information out of a national “Financial Crimes” database should seek legal counsel to determine how to structure their entities with the CTA in mind. Bespoke Group actively works with its clients to navigate these reporting requirements while optimizing for privacy. 

Why FinCEN’s Regulations Endanger the Right to Privacy 

For decades, LLCs have been used both to enhance asset protection and to provide privacy for personal use holdings like vacation homes, non-mortgaged primary homes, or personal & family investment portfolios. It has been standard wealth planning practice to use trust-owned LLCs in robust privacy jurisdictions like Wyoming or South Dakota to allow affluent clients to hold real estate or other family assets in private structures, often within tax-advantaged irrevocable trusts. Financially and commercially successful individuals understandably seek to preserve their privacy and protect themselves and their family from curiosity seekers or from those with nefarious intent to harm the client or the client’s family.

The requirement for LLCs created and registered in the U.S. to report personal information to a federal database managed by the Financial Crimes Enforcement Network raises valid concerns for individuals focused on protecting their privacy.

These regulations and reporting processes may significantly affect the right to privacy for many individuals and families in the U.S. Personal information stored within a financial crimes database is not guaranteed to be protected from a data breach, and digital records are effectively permanent historical and traceable records. Furthermore, with these regulations in place, efforts to protect one’s privacy through an LLC structure puts individuals in the uncomfortable position of being tracked within a financial crimes database. Many people prefer the ability to protect their privacy without coming under the scrutiny of financial crimes enforcement agencies or any type of criminal enforcement agency.

A Precedent Has Been Set

Another important factor to consider is the potential expansion of this act over time, resulting in additional beneficial ownership information being collected at the federal and state level. Now that a precedent has been set, expanding the scope of information that could be collected in the future is potentially a lower hurdle.

Since the initial rollout of the CTA, various states have been working on their own reporting requirements, often focusing on narrower categories of “reporting companies”. In addition to placing greater administrative burdens on individuals and corporations, state-level BOI collection will likely raise concerns regarding privacy and could potentially increase the risk of data breaches as this information is stored in a separate database. Moreover, states may implement more frequent data collection timelines, and companies that do not adhere to these requirements could face additional fines and penalties.

Our Focus on Privacy

Privacy is generally understood to be a fundamental human right and preserving and protecting the privacy of our clients is central to our services. Our team is dedicated to providing industry-leading wealth management solutions, and privacy is a key factor in every decision we help our clients make. The Corporate Transparency Act presents new challenges for our industry, and in an ever-changing regulatory environment, Bespoke will always look for opportunities to optimize for privacy while maintaining compliance with existing regulations.

Additional Resources: FinCEN Beneficial Ownership Reporting

FinCEN Beneficial Ownership Information Reporting Rule Fact Sheet
https://www.fincen.gov/beneficial-ownership-information-reporting-rule-fact-sheet

FinCEN Beneficial Ownership Information FAQ
https://www.fincen.gov/boi-faqs

Beneficial Ownership Reporting Outreach and Education Toolkit
https://www.fincen.gov/boi/toolkit

If you’re interested in learning more about Bespoke’s approach to private wealth management and how we can help you build a secure financial future, we invite you to reach out to us directly. We’d be happy to set up a confidential consultation at your convenience.

Thank you for considering Bespoke as your partner in wealth management. We look forward to the opportunity to work with you.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.

Enhance Your Philanthropy and Tax Planning with Strategic Giving Tools

On Day 3 of the Onchain Giving Summit hosted by Endaoment, Bespoke founder Matt McClintock speaks to Adam Blumberg, Bespoke Client Services Associate and co-founder of Interaxis, about the importance of incorporating philanthropy into estate planning.

Navigating the intersection of charitable giving and tax planning can unlock significant financial and philanthropic opportunities. Whether you’re looking to maximize your tax benefits, manage appreciated assets, or support causes you care about, various strategies can enhance both your financial plan and charitable impact.

Maximizing Tax Benefits Through Charitable Giving in Estate Planning

Charitable giving is a powerful way to support causes you care about, and it can also play a key role in estate planning. Whether making outright gifts to family members or donating to charitable organizations, there are significant tax benefits available. For cash gifts to qualifying charities, you can deduct up to 60% of your adjusted gross income (AGI). Donations of property, such as real estate, offer deductions ranging from 20% to 50% of AGI, depending on the type of asset and charity. Thoughtful philanthropy not only helps others but can also create lasting tax advantages for your estate.

Navigating Charitable Donations of Cryptocurrency: Timing and Appraisals

When donating cryptocurrency or digital assets to charity, it’s essential to establish the value at the time of the gift. For tax deduction purposes, the gift must be supported by a qualified appraisal, just like any other donation. Fortunately, there are expert appraisers who specialize in valuing digital assets like Bitcoin, ensuring accurate reporting for charitable contributions.

Raise Your Charitable Impact with a Donor-Advised Fund

Donor-advised funds (DAFs) are a smart, flexible option for individuals looking to make large charitable gifts but aren’t yet sure where to direct the funds. After experiencing a major income tax event, many donors want to secure a significant charitable deduction without needing to decide immediately which charities to support. A DAF allows donors to contribute now, receive the tax benefit, and take their time selecting causes to fund later. It’s an ideal solution, especially when gifting non-traditional assets like cryptocurrency. With tools like DAFs, philanthropy becomes more adaptable, offering greater control and financial benefits for donors.

Leverage Charitable Lead Trusts for Tax Benefits and Future Generational Wealth

A charitable lead trust offers a strategic way to support charities while benefiting your heirs. By establishing this trust, you direct it to make fixed annual payments to a qualifying charity, such as a donor-advised fund or family foundation, for a specified term (e.g., 10 or 20 years). At the end of this period, any remaining trust assets transfer gift-tax-free to your chosen beneficiaries, like your children. Additionally, you can receive an upfront tax deduction based on the trust’s initial value. This setup not only supports charitable causes but also provides tax advantages and protects your heirs’ future interests.

Unlock Tax Benefits and Charitable Impact with a Charitable Remainder Trust

A Charitable Remainder Trust (CRT) is a savvy tool for managing appreciated assets like Bitcoin or ETH while supporting charitable causes. By transferring these assets into a CRT, you avoid immediate capital gains taxes when the trust sells them. Instead, you receive an income stream from the trust for a set period or for life. At the end of this term, the remaining assets go to your chosen charity. This strategy not only maximizes your charitable impact but also provides you with tax benefits and ongoing income, making it a powerful option for both philanthropy and financial planning.

This information is intended for general educational purposes only and should not be construed as legal or investment advice.