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11 JAN 2022

10:00

Cryptocurrency

Redefining Bitcoin Alpha

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Author: liam

How One Family Is Future-Proofing a Bitcoin Fortune

Posted on by liam

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.

How One Investor Turned Capital Into Real Change

Posted on by liam

Every financial decision leaves a footprint.

Some create opportunity. Some drive progress. Others fade without much consequence. For today’s most sophisticated investors, capital is more than a number on a statement, it’s a lever for building the world they want to see. They expect performance, but they also want precision, clarity, and the ability to see the tangible difference their wealth is making.

A Peak Inside True Impact

Bespoke was fortunate to partner with a values-driven investor who understood her position as a steward of significant capital and the responsibility that comes with it. She knew her resources gave her a rare ability to move the needle on issues she cared about, particularly empowering women and underrepresented communities. But her options, until then, had been uninspired: generic “impact” funds with glossy ESG labels but little substance.

She wasn’t looking for tokenism. She wanted her portfolio to be as intentional and effective as her philanthropic work – a living extension of her values, measurable in both returns and outcomes.

The Challenge: Moving Beyond Surface-Level ESG

When we reviewed her portfolio, it was a standard investment portfolio with just 4% allocated to ESG-labelled ETFs. On paper, it seemed “impact-focused,” but it didn’t reflect the unique mission she had in mind. This isn’t unusual. Many well-intentioned investors are matched with broad, standardized solutions simply because the tools are familiar and easy to implement.

The real gap was clarity. Her vision for creating change hadn’t been fully explored, so her portfolio wasn’t designed to match it. Most investors (even sophisticated ones) aren’t given the full picture of what’s possible and may not know what questions to ask or what’s available to them. At Bespoke, we make it our work to go deeper, uncover overlooked opportunities, and create strategies that are as intentional and distinctive as the people behind them.

Step 1: Understanding the Client

Impact investing is not a template we pull off the shelf; it’s as individual as the person behind the portfolio.

Our first step was to really understand her, not just her net worth, but her story, her ambitions, and the role she wanted her capital to play in the world. We explored the season of life she was in, the level of liquidity she wanted to preserve, her appetite for risk, how public or private she wanted her decisions to be, and how hands-on she hoped to be in the process.

This wasn’t a “fill out a questionnaire and we’ll get back to you” exercise. It was an ongoing, in-depth dialogue that revealed not just numbers, but priorities and boundaries. This created the foundation for building a strategy that would serve both her financial future and her mission.

Step 2: Designing a Comprehensive, Impact-Centered Wealth Strategy

We didn’t just slot her into “impact” funds with a green label. We mapped her entire wealth ecosystem: public equities, private markets, and philanthropic vehicles like a Donor-Advised Fund (DAF) and asked one question at every turn: Is this asset working as hard as it could toward your mission?

From there, we built a portfolio where every allocation had a purpose:

  • Venture Capital: Direct allocations to funds owned and managed by women and minority founders, backing companies that tackle real community challenges – from women’s health to educational access across the country.
  • Municipal Bonds: Targeted investments in healthcare and educational infrastructure in underserved communities.
  • Private Credit: A fund providing essential growth capital to female-led startups at the grassroots level.
  • DAF Strategy: A bespoke public markets approach designed for both impact and returns, providing tax advantages and strategic flexibility for giving.

We also extended her values into the public markets, not with vague “sustainability” screens, but with precision, identifying companies driving ecological balance, human empowerment, and ethical innovation. This gave her portfolio both the liquidity and global reach she needed, without diluting the mission.

The Results: Alignment in Action

The transformation was significant. Today, 95% of her wealth is aligned with strategies that have a clear, measurable connection to her mission of empowering women and underserved communities. Her investments and philanthropy now operate in sync – amplifying each other’s impact, creating change today while laying the foundation for lasting systemic shifts.

Lessons for Other Investors

If you have the capacity to shape the world with your capital, you shouldn’t be offered Just Your Average investment strategy. True impact requires moving beyond labels and into the realm of bespoke strategy – one that honors your liquidity needs, financial ambitions, and vision for the future.

It takes a partner willing to look under every stone, to find the overlooked opportunities, and to hold both the complexity of your wealth and the nuance of your purpose in the same hand. At Bespoke, that’s what we do: craft portfolios that tell a story, reflect your values, and leave a legacy far beyond financial returns.

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.

How One Philanthropic Strategy Is Designed for Enduring Change

Posted on by liam

Philanthropy at the highest level is rarely a matter of annual budgets or short-term campaigns. For institutions with ambitions measured in centuries, the challenge is altogether different: how to finance impact today while ensuring that the capital base not only survives, but grows, in perpetuity. It is a discipline that blends investment sophistication, governance foresight, and mission fidelity.

Our recent engagement with a patron dedicated to preserving cultural heritage and educating future generations offers a case study in this art of longevity.

The Challenge: Balancing Impact and Legacy

The client’s vision was both ambitious and clear: establish a global foundation to safeguard historic artifacts and inspire young minds through education. The investment mandate, however, was far from simple. The foundation required a portfolio resilient enough to weather decades of market cycles, liquid enough to support consistent grant-making, and aligned with values that stretched across geographies and generations.

A complicating factor—though one rich with potential—was the presence of a substantial Bitcoin position. While the asset’s long-term trajectory has been compelling, its volatility and regulatory flux demand a more sophisticated integration than most philanthropic portfolios contemplate.

A Resilient, Rules-Based Framework

The solution was not a static endowment, but a living capital strategy. We constructed a fully liquid portfolio spanning public markets, real assets, and mission-aligned investments, designed to adapt as global conditions shift. The aim was not simply capital preservation, but sustainable growth across market regimes.

The bitcoin allocation was incorporated not as a speculative outlier, but as a strategic core holding—managed via a disciplined, rules-based price cycle framework. This approach tempers volatility risk while preserving the upside potential that drew the client to the asset in the first place.

The resulting structure fuses traditional stability with forward-looking innovation, allowing the foundation to maintain liquidity for its work while benefiting from assets positioned to appreciate over the long arc of its mission.

Stewardship in Action

True perpetuity planning extends well beyond investment mechanics. We serve not only as portfolio architects, but also as active members of the foundation’s Philanthropy Committee— ensuring that capital allocation decisions remain tethered to mission objectives. This alignment between governance, investment, and philanthropy is the quiet infrastructure upon which multi-century institutions rest.

Lessons for the Philanthropically Ambitious

For wealthy patrons seeking to endow their legacies, several principles emerge from this case:

  • Liquidity without fragility – A foundation must be able to fund its mission in any market environment, without impairing its capital base.
  • Innovation with discipline – Modern assets such as Bitcoin can enhance long-term returns, but only when governed by clear, systematic frameworks.
  • Governance as strategy – The longevity of a philanthropic institution rests as much on its decision-making processes as on its balance sheet.
  • Adaptation as a virtue – Investment strategies for century-spanning missions must evolve proactively, anticipating economic and geopolitical shifts.

Preserving cultural heritage is an act of defiance against time. Funding that mission demands an equally durable financial architecture—one that can absorb shocks, capture opportunities, and remain faithful to purpose across generations.

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.