Category: Cryptocurrency
How One Family Is Future-Proofing a Bitcoin Fortune
The first decade of Bitcoin created wealth at a velocity without precedent in modern finance. For a narrow circle of early adopters, modest experiments in 2010 and 2011 compounded into fortunes measured in hundreds of millions. Yet the true test of this capital lies not in its creation, but in its preservation. How do you translate an asset born in cryptography into a legacy measured in generations?
Our work with one such family illustrates the unique governance challenges of digital wealth, and the strategies required to make it endure.
The Client: A Bitcoin Fortune Without a Blueprint
The family acquired a substantial quantity of bitcoin in its earliest days. By 2017, their holdings had appreciated to levels that far exceeded expectation. Their initial mandate to us was straightforward: estate planning. Yet as we examined their position, it became clear that their needs extended far beyond legal documentation.
They were confronting questions few private banks or wealth managers could answer:
- How to structure holdings to maximize security and tax efficiency?
- How to integrate a volatile, appreciating asset into a broader portfolio without neutralizing its potential?
- How to ensure the next generation could both understand bitcoin and steward it effectively?
From Estate Planning to Fractional Family Office
The engagement rapidly evolved into a broader role as the family’s fractional family office—reflecting the multidimensional complexity of wealth comprised largely of bitcoin and related assets and the lack of established infrastructure to manage it.
Our strategy unfolded across four fronts:
Long-Duration Trust Structures
Using jurisdictions such as Nevada (365-year trusts) and Wyoming (1,000-year trusts), we created vehicles designed to preserve digital wealth over centuries, offering both tax advantages and governance frameworks that can endure through multiple generations.
Custody and Security Protocols
Recognizing that digital asset security is as much human as technological, we implemented custody solutions blending institutional-grade systems with inheritance contingency planning.
Integration with Tangible Assets
We advised on strategic acquisitions—real estate, income-generating holdings—to diversify the portfolio while keeping bitcoin as a central store of value.
Generational Education
We went beyond the mechanical transfer of financial wealth, emphasizing stewardship, impact, and purpose—equipping rising generations to manage Bitcoin with intelligence, responsibility, and success.
Why Bitcoin Wealth Demands a Different Playbook
For highly affluent families accustomed to equities, bonds, and property, bitcoin’s characteristics are both attractive and challenging:
- Absolute control via keys – Unlike many financial assets, bitcoin is a purely digital bearer asset: control of the cryptographic key is control of the asset. Risk management and wealth transition requires extreme care.
- Volatility and timing – Extreme price swings create opportunities for intelligent profit or loss harvesting.
- Regulatory uncertainty – Evolving tax and reporting frameworks demand agile and attentive planning.
Our governance model addresses these head-on, embedding a fragile digital asset in a robust legal, operational, and educational framework.
From Serendipity to Strategy
Bitcoin’s meteoric rise rewarded foresight and conviction. But without disciplined planning, such fortunes can be eroded by taxes, mismanagement, or security failures. With the right structures, they can instead be transformed into enduring legacies.
These engagements are about more than financial engineering. They are about honoring the serendipity of early adoption by ensuring it survives—secure, comprehensible, and aligned with family values—for generations to come.
Note: this case study is based on the solution mix currently managed by Bespoke but is not an exact representation of a current client engagement, in order to provide our client with the level of privacy they expect. The success outlined within this article is not necessarily indicative of future successes. Investing in Cryptocurrency is considered a high risk investment.
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.
Structured Planning for Unconventional Assets like Bitcoin
As digital currencies like Bitcoin gain prominence, attorneys, financial advisors, and trustees must adeptly navigate the complexities of structured planning to manage, protect, and optimize these unconventional assets.
Bespoke’s Co-founder, Matt McClintock, demystifies estate planning for digital assets in this talk with BitDevs.
Here’s what the discussion covered…
The Benefits of Using Creative or Personal Names for Trusts
Using creative or personal names for trusts enhances privacy and security while adding a meaningful touch. By choosing a unique name—like a favorite landmark or character—you obscure your identity, protecting personal details from public records and reducing the risk of identity theft. This approach ensures confidentiality, making it harder for outsiders to connect the trust with your personal affairs. Additionally, a personal name adds significance to the trust, making the estate planning process more engaging and reflective of your values.
Understanding Revocable Living Trusts: Asset Protection and Tax Implications
A revocable living trust doesn’t offer asset protection from creditors or tax benefits. During your lifetime, creditors can access the trust’s assets since you control and can revoke it. Tax-wise, there are no advantages or detriments; assets remain part of your estate for tax purposes, and income or gains are reported on your personal tax return. The main benefit of a revocable living trust is efficient estate management. It helps avoid probate and allows for private, streamlined asset distribution and management in case of incapacity or death, ensuring a smoother transition of your estate.
Revocable Trust Structure: Protecting Assets for Spouse and Children
A revocable trust structure designed to protect assets for both your spouse and children allows your spouse to benefit from and manage the assets without full ownership, safeguarding against misuse. It also ensures that the assets remain in the trust and are available for your children if your spouse passes away first, avoiding disinheritance. Your spouse acts as trustee, balancing control with asset protection. This approach protects assets, supports your spouse, avoids probate, and simplifies transfer, with clear terms and effective family communication being key considerations.
Legal Limits on Trust Provisions
Drafting effective trust provisions requires balancing detailed instructions with legal and practical considerations. Legal limits include public policy restrictions that invalidate provisions based on religion, race, or illegal incentives, and adherence to the rule against perpetuities, which limits how long a trust can last.Practically, granting trustees broad discretion within clear guidelines helps them manage assets flexibly and adapt to unforeseen changes. Avoid overly complex provisions to prevent administrative difficulties and disputes. Collaborate with legal experts to ensure enforceability, communicate your intentions clearly to trustees and beneficiaries, and regularly review and update the trust to reflect evolving needs and circumstances.
Mechanical Transfer vs. Intentional Transfer
The key difference between mechanical and intentional asset transfers lies in the clarity and structure of the transfer process. Mechanical transfers, like handing over a vault combination without further instructions, can lead to uncertainty and unintended consequences. In contrast, intentional transfers involve detailed planning and legal structures, such as trusts, which ensure assets are managed, protected, and distributed according to the original owner’s wishes. Using trusts, clear instructions, and professional advice ensures assets are safeguarded, privacy is maintained, and tax implications are optimized, effectively achieving your estate planning goals.
Mastering Unconventional Asset Management
Structured planning for unconventional assets, like Bitcoin, requires a thoughtful and adaptive approach that integrates security, legal compliance, and asset management. By leveraging creative strategies—such as using personal names for trusts to enhance privacy or crafting intentional asset transfers through detailed estate planning—individuals can protect their assets while ensuring smooth transitions for future generations.
Whether dealing with digital currencies or more traditional assets, Bespoke is committed to help optimize estate planning and safeguarding your legacy.
Strategic Wealth Management for Bitcoin Holders
We are witnessing remarkable advancements on secondary layers within the Bitcoin network. Bitcoin core developers are continually innovating to enhance the scalability and transaction capacity of the network, allowing it to perform a broader range of functions. These developments not only increase Bitcoin’s utility but also have the potential to significantly boost its value.
This blog post summarizes a recent talk our co-founder and executive managing director Matt McClintock shared with the Unchained audience. You can tune into the full video at the bottom of the page.
The Dynamics of Bitcoin Value
Predicting the spot price of Bitcoin in U.S. dollar terms remains a challenging endeavor. However, Michael Saylor’s assertion that “it goes up forever” captures a fundamental belief within the Bitcoin community: as Bitcoin’s network grows and its applications expand, its value is likely to increase. This upward trajectory is compounded by the depreciation of the U.S. dollar, which typically loses value at a rate of 2 to 8 percent per year. As Bitcoin appreciates and the dollar depreciates, the value gap between them continues to widen. This trend suggests that Bitcoin’s long-term value proposition remains robust. For the U.S. to fully leverage this potential, it might need to consider holding Bitcoin as part of its strategic economic reserves.
The Rise of Ideological Investing
Investors, especially the younger generations, are more inclined to align their investments with their personal values and worldviews. This trend is reflected in the growing interest in companies that demonstrate social responsibility, such as having women in the C-suite or implementing sustainable practices. Investors are now willing to prioritize ideological alignment over traditional financial metrics like alpha and beta.
At Bespoke Group, we help our clients uncover the deeper purpose behind their wealth. We explore questions such as: What does this wealth mean to you? How can it be used to express your values through investments and philanthropy? By addressing these questions, we guide our clients in making investment decisions that reflect their ideologies and contribute to a better world.
Planning for Transformative Wealth
Many individuals possess substantial Bitcoin wealth, which necessitates careful consideration of its implications for their families and communities. The case of Mircea Popescu, who allegedly held over a million Bitcoins and tragically drowned without clear succession plans, underscores the importance of strategic planning. Whether one owns 100, 1,000, or 10,000 Bitcoins, these assets represent transformative wealth that demands thoughtful succession and estate planning.
Bitcoiners, especially those who have weathered multiple market cycles and significant industry upheavals (such as the collapses of Three Arrows, Terra Luna, and FTX), often develop a mature and ideological perspective. They view Bitcoin not just as a store of value but as a revolutionary asset with the potential to transform their lives and the futures of their families. Structuring and managing this wealth strategically is crucial for its preservation and growth.
The Generational Shift and Social Upheaval
Our client base is largely composed of individuals younger than 50, reflecting a significant generational shift in attitudes towards wealth and investing. Younger generations, including Gen X and Millennials, are more ideologically driven compared to the Baby Boomers. They possess significant wealth, often accumulated through unconventional means like cryptocurrency investments, and are motivated by a desire to make a positive impact on the world.
This generational shift coincides with a period of significant social upheaval in the United States. The “Fourth Turning,” a concept popularized by William Strauss and Neil Howe, suggests that American society undergoes a major transformation every 80 to 100 years. We are currently in a crisis phase, characterized by societal reimagining and reorganization. This period of transformation is driving affluent individuals to align their wealth with their values, whether through investments, philanthropy, or family legacy planning.
The Role of Bitcoin ETFs
The introduction of Bitcoin ETFs has been a significant milestone, signaling growing acceptance of Bitcoin as a legitimate alternative asset class. While Bitcoin ETFs provide an easier access point for retail investors, there are concerns that they might simplify Bitcoin ownership to the point where investors miss out on understanding its deeper value. The influx of Bitcoin into ETFs could potentially centralize control, but the high HODL rates suggest that many Bitcoiners are committed to maintaining their holdings.
Global Strategies and Regulatory Risk
Navigating regulatory risks within the United States is a critical concern for many Bitcoin holders. At Bespoke Group, we help clients plan for these risks through global custodial relationships and structures, such as trusts in the Cook Islands or foundation companies in Switzerland. These structures can protect Bitcoin assets from regulatory reach while allowing clients to maintain control and benefit from their investments.
Our Approach at Bespoke Group
One of our specialities is sophisticated wealth management tailored for Bitcoin holders. We embrace a Bitcoin-centric ethos and understand the unique complexities and needs of our clients. Our approach is designed to balance traditional wealth management principles with the distinctive nature of Bitcoin assets.
We recognize that many Bitcoiners are ideological about their investments, especially those who have been involved for several years. These individuals often possess a long-term vision for their wealth, viewing it as a means to not only secure their own futures but also to make a positive impact on their families and communities. Our goal is to help these clients strategically plan for the future, ensuring that their Bitcoin wealth is managed and preserved in a way that aligns with their values and aspirations.
The following information is intended for general educational purposes only and should not be construed as legal or investment advice.
Insights on Bitcoin ETFs and Behavioral Finance
In the fast-paced world of cryptocurrency, fortunes can change overnight. In a recent conversation, Bespoke Co – founder Matthew McClintock, a legal expert and advisor to high-net-worth individuals in the crypto space, and Crystal Wampler Bespoke’s Client Services Associate and guest host of the show delve into the significance of understanding the evolving landscape of crypto assets, the potential impact of Bitcoin ETFs, and the crucial role of behavioral finance in wealth management.
Listen to the conversation on the AFO | Wealth Management Forward Podcast with host Rory Henry.
The Dawn of Retail Investment in Crypto
McClintock emphasizes the significance of the evolving landscape of crypto assets, particularly in how it affects retail investors. He notes the challenges that everyday investors face when dealing with cryptocurrency exchanges, from navigating complex protocols to grappling with custody solutions. However, with the emergence of Bitcoin ETFs, McClintock sees a potential turning point. These ETFs could provide retail investors with easier access to Bitcoin price exposure without the complexities of owning and managing the underlying asset.
The Role of Trusts in Crypto Wealth Management
As crypto wealth grows, McClintock highlights the importance of trust structures in estate planning and asset protection. He discusses the various trust vehicles available, from revocable trusts to dynasty trusts, and emphasizes the need for creative solutions tailored to the unique challenges posed by crypto assets. McClintock also explores the role of private trust companies in providing custodial solutions for digital assets, offering increased security and flexibility for affluent crypto investors.
Navigating Behavioral Challenges in Crypto Wealth Management
Crystal asks: “How do you navigate these new millionaires and billionaires, how do you help them navigate their new wealth?” In managing newfound crypto wealth, McClintock underscores the importance of behavioral finance principles. He emphasizes the need for advisors to approach clients with respect, curiosity, and zero judgment, acknowledging the significance of their wealth journey. McClintock encourages clients to explore questions of legacy, impact, and personal fulfillment, guiding them in crafting a holistic wealth management strategy aligned with their values and aspirations.
The Future of Crypto Wealth Management
Looking ahead, McClintock remains optimistic about the potential of Bitcoin ETFs to drive further adoption and investment in the crypto space. He anticipates a significant demand shock on Bitcoin as ETF sponsors acquire assets to back ETF shares, potentially leading to accelerated growth in crypto markets. However, McClintock also stresses the importance of prudent planning and risk management, urging investors to consider the broader implications of their wealth decisions.
As the crypto landscape continues to evolve, understanding the intersection of legal, financial, and behavioral factors will be essential in helping clients achieve their long-term financial goals while embracing the opportunities presented by digital assets.
Grab the full conversation here.
This information is intended for general educational purposes only and should not be construed as legal or investment advice.
Mastering Estate and Legacy Planning for Cryptocurrency Assets
Learn more about estate and legacy planning in the age of crypto assets and digital wealth in Adam Blumberg’s piece Estate and Legacy Planning for Crypto Assets.
The surge in cryptocurrency adoption necessitates proper estate and legacy planning for crypto assets. Despite an uncertain regulatory environment, investment in blockchain-based systems continues in the U.S., and other regions have already enacted crypto-related legislation.
Safeguarding Digital Legacies
A significant number of investors, especially younger ones, possess crypto assets in various forms, requiring advice on estate planning. Often, these investors don’t recognize the need for formal planning due to crypto’s volatility and their perceived wealth. Legacy planning for digital assets differs from traditional assets. The technical aspect, ensuring heirs can control the assets, is more critical than the legal planning. A team like Bespoke can add value by preparing the inventory, creating a tech-focused legacy plan, and educating heirs on the use of keys and investment philosophies.
Unraveling the Complexities of Crypto Asset Planning
Crypto asset planning also presents unique challenges like regulatory ambiguity, rapid innovation, and cost basis considerations. An asset’s potential to increase rapidly in value underscores the importance of legacy planning. Ultra High Net Worth (UHNW) individuals in crypto face additional difficulties, such as tax issues complicated by basis considerations and jurisdictional questions, requiring crypto-literate advisors and attorneys.
In summary, as cryptocurrencies rise in prominence, the role of financial advisors in guiding clients through estate and legacy planning for digital assets becomes vital. It’s essential for estate plans to accommodate digital assets efficiently and legally, requiring a strategic blend of tech-native wealth transfer and protection plans, coupled with collaborative efforts with legal and tax professionals.
The following information is intended for general educational purposes only and should not be construed as legal or investment advice.
Stephan Livera Podcast: UHNW Bitcoin Strategies
Stephan Livera Podcast: UHNW Bitcoin Strategies
Matthew McClintock, executive managing director of Bespoke Group joined Stephan Livera on his podcast to chat about Bespoke’s multi-family office and private trust company services for ultra-high net worth US clients. They discuss:
- What level of wealth qualifies for a family office?
- What are the concerns of Bitcoin-affluent families?
- What kind of structures can they use?
- Benefits of these structures
- Trade offs of the approach
- How the Sovereign Individual thesis may play out
- Should UHNW Americans consider staying out of these structures?
- What’s needed from a technology and culture perspective?
Check out the podcast on Apple, Android, or by clicking the link below.
Wealth Actually Podcast: Crypto and NFT Estate Planning Update
Wealth Actually: Crypto and NFT Estate Planning Update with Matthew McClintock (Part 2)
Matt returned to Frazer Rice’s “Wealth Actually” podcast to expand on their 2020 discussion surrounding inter-generational wealth transfer issues for individuals with large cryptocurrency holdings. The last time Matt and Fraser spoke, “Bitcoin was around $10,000 . . . By August 2021 it was valued in the $48,000 range (having spiked over 60K!). Many other cryptocurrencies and digital assets like Non-Fungible Tokens (NFTs) have seen similar value increases.”
In this podcast, Matt discusses:
- What is different around legacy planning in the crypto world since October 2020 and August 2021?
- What is involved with estate planning in the white hot NFT space?
- How does one properly staff the roles in crypto estate planning structures?
Tune into the podcast here: https://frazerrice.com/blog/ep-91-matthew-mcclintock-part2/
The following information is intended for general educational purposes only and should not be construed as legal or investment advice.