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.
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.