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PODCAST QUEUE

PODCAST TRANSCRIPT

11 JAN 2022

10:00

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.

Aligning Wealth with Values in a Changing World

In this episode of the Cognitive Investments podcast, Matt (Bespoke Co-Founder) and Jacob (Partner & Director of Geopolitical Analysis at Cognitive Investments) explore the critical aspects of aligning wealth with personal values, the evolving landscape of estate planning, the rise of cryptocurrency, and broader geopolitical influences on financial strategies.

Tune into the full episode:

Key Concepts and Timestamps

03:00 Matt’s Career Journey

  • Matt shares his professional background, highlighting his path and the experiences that shaped his approach to wealth management.

06:25 The Story of Bespoke Group

  • The founding and evolution of Bespoke Group, emphasizing the importance of tailor-made financial services.

15:00 How to Own VS Where to Own VS What to Own

  • Discussion on different aspects of ownership, focusing on strategic decision-making in wealth management.

16:55 How Estate Planning is an Act of Sovereignty

  • Framing estate planning as an exercise in personal sovereignty, offering control over one’s financial legacy.

20:00 The Flaws of Wills and Probate

  • Critique of traditional wills and probate processes, discussing common pitfalls and inefficiencies. Jacob shares a personal anecdote about the wills his late mother and father left behind.

21:50 Privatizing the Process

  • Why privatized methods to streamline estate management should not be overlooked.

25:45 Understand the Tax Law

  • Tax news and updates. Stay abreast to changes of the tax law that will affect current and future estate planning structures.

31:21 What Type of Impact Do You Want Your Wealth to Have?

  • Exploring the desired impact of wealth on future generations and society, stressing thoughtful planning.

37:54 Why Matt Hates the Word Estate Planning

  • Matt explains his aversion to the term “estate planning” and proposes a more holistic approach.

40:00 A Thoughtful Estate Plan is an Act of Love

  • Emphasizing that estate planning is an act of love and responsibility towards one’s family and legacy.

42:50 Where the Future of Money is Headed

  • Insight into the future of money, particularly the evolution of cryptocurrency and its implications.

46:40 Impact of Bitcoin’s Evolution

  • Discussion on how Bitcoin has emerged as a robust form of money and its role in modern financial systems.

54:02 Widening Delta Between Value of Assets and Value of Our Currency

  • Reflecting on the growing disparity between asset values and currency value, and its implications for financial planning.

Matt and Jacob underscore that estate planning and financial management are more than just technical exercises; they are about holistic life optimization and aligning financial strategies with personal values. They advocate for proactive and dynamic estate planning to ensure long-term well-being and effective wealth management.

e-State Planning for Bitcoin and Other Crypto Assets

How to build trust in an increasingly digital world? With the rapid advancements in technology, the podcast episode: e-State Planning for Bitcoin and Other Crypto Assets explores how trust is both essential and challenging to establish and maintain in various aspects of our lives. Jonathan Mintz, Senior Managing Director of Bespoke Group, delves into the crucial topic of building trust in an increasingly digital world on the “Trust Me” podcast with Kevin Bryce Jackson. 

This blog post is a summary of their conversation. 

Trust in the Digital Landscape

The conversation is kicked off with discussion surrounding the importance of trust in today’s digital landscape. Jonathan highlights how trust forms the foundation for successful relationships, transactions, and collaborations, emphasizing its impact on businesses, institutions, and individuals.

Trust – Eroding Challenges

Drawing on insights from industry experts and thought leaders, Jonathan and Kevin explore the challenges posed by cybersecurity threats, data breaches, and privacy concerns that erode trust in the digital realm. As well as discussing perspectives on the measures individuals and organizations can adopt to protect their data.

The podcast also delves into the role of trust in the context of social media and online platforms. It examines the spread of misinformation, fake news, and the manipulation of online content, shedding light on the critical need for platforms to prioritize trust and integrity.

Rebuilding Trust

Throughout the episode Jonathan discusses practical strategies for rebuilding trust and fostering transparency. He explores the significance of accountability, authenticity, and ethical behavior in cultivating trust among consumers, clients, and partners. Additionally, the podcast discusses the role of technology itself in facilitating trust, such as blockchain and decentralized systems.

“Trust Me” aims to equip listeners with a deeper understanding of the importance of trust and its influence in our digital lives. By addressing the challenges and providing actionable insights, the episode offers a valuable resource for individuals and organizations striving to establish and maintain trust in an ever-evolving digital landscape.

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