In a world where dreams are broadcast in real time and success is often measured by the size of a contract, the allure of the “finish line” in professional sports is undeniable. Overnight, a rookie becomes a centimillionaire; years of discipline and sacrifice culminate in a signature on a deal that alters the course of a family’s future. From the outside, these moments represent the pinnacle. But within the arena of wealth, they mark the beginning of an entirely new game.
Modern professional sports are defined by scale—of performance, visibility, and compensation. Yet behind the headlines and highlight reels lies a sobering truth: wealth earned quickly, without a clear and adaptive plan, often proves unsustainable. Despite support systems like agents, trainers, managers and family, many athletes lack a comprehensive framework to preserve and protect their wealth.
Curiously, the analogy that best captures this dynamic doesn’t come from football or basketball, but from curling—a sport where fame and fortune rarely follow. In curling, the shooter initiates the play with precision and power, launching the stone toward a distant target. But what ensures success isn’t the throw alone; it’s the team—sweepers and strategists—who work in tandem to guide and optimize its trajectory. The shot may start strong, but it finishes well only when all parties are aligned.
This also applies to wealth planning. The contract may be the catalyst, but it is not the conclusion. What comes next is where real strategy begins.
A New Game, Higher Stakes
Athletes face the complex challenge of managing not just newfound wealth, but an entirely new reality. One marked by higher stakes, limited time horizons, and deeply personal vulnerabilities. While performance may have delivered the paycheck, it’s foresight, patience, and structure that preserve it.
At Bespoke Group, we’ve learned that generational wealth is not built on moments, but on systems. Our role is to serve as a force multiplier—like the sweepers in curling—working quietly and effectively to create the conditions for long-term success. This is not about financial management alone. It’s about constructing an intentional life, designed around security, resilience, and purpose.
And the numbers tell a compelling story. Nearly 78% of NFL players report financial stress just two years post-retirement, as reported by Sports Illustrated. In the NBA, approximately 60% find themselves nearing bankruptcy within five years of leaving the court. These statistics aren’t just cautionary tales, they’re symptoms of a system optimized for short-term gain, not long-term wellbeing.
Vulnerabilities Beyond the Balance Sheet
Financial instability is just one facet of the risk. Privacy breaches, civil litigation, and physical safety threats have become increasingly common among high-profile athletes. Recent headlines involving figures like Patrick Mahomes, Joe Burrow, Luka Doncic, and Travis Kelce underscore a troubling trend: even the most secure-seeming lives are vulnerable.
And the threat doesn’t always come from outside. Divorce rates among athletes are estimated between 60–80%—a sharp increase over the national average. Without thoughtful structures in place, such as prenuptial agreements, asset protection trusts, and discreet legal counsel, wealth can quickly become exposed.
Traditional sports agencies, focused on contracts and endorsements, often lack both the incentive and infrastructure to address these deeper, long-term considerations. Our team views wealth as a living ecosystem. One that requires thoughtful stewardship, not reactive management.
Building Legacy with Intent
At Bespoke, we see wealth not as a moment, but as a continuum. One that begins in earnest when the spotlight fades and the real complexity begins. We focus on what comes next: building structure, resilience, and longevity into that success.
Our role is not to chase opportunity but to design around it. We help clients navigate the financial, legal, and personal complexities that follow sudden wealth—from asset protection and privacy to long-term investment discipline, family governance, and philanthropy. In this context, wealth is not just managed, it is curated, protected, and positioned to endure.
If you’re exploring how to align your wealth with long-term purpose and strategy, we invite you to connect with us. Whether you’re establishing a family office or rethinking an existing structure, Bespoke offers discreet, high-touch advisory tailored to your needs. Contact us to schedule a confidential consultation—we’re here to help you navigate what’s next with confidence and intention.
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.
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.
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.
