Two Stewards

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If you want to go fast, go alone. If you want to go far, go together.
—African Proverb

At Two Stewards, we are dedicated to creating practical, self- and system-powered learning environments. For those in interdisciplinary, high-stakes, long-term, and usually inter-generational human systems, learning environments are transformational and irreplaceable.

While such systems are indeed everywhere, Two Stewards is currently focused on meeting the needs of four concentric demographics:

  • Families contemplating or attempting to transition significant assets, particularly enterprise-based assets. This is the primary demographic on which all others are centered.
  • Professionals who seek to support enterprising families. These are the lawyers, financial planners, accountants, asset managers, insurance professionals, trustees, financiers, psychologists, physicians, clergy, addiction counselors, and the denizens of the enterprise C-suite.
  • Business owners who seek to holistically serve systems of enterprising families and their supporting professionals.
  • Investors seeking to be involved in the above markets.

Why These Demographics?

Among others, two words dominate: complexity and experience.

Complexity

I wouldn’t give a fig for simplicity on this side of complexity, but I would give my life for simplicity on the other side of complexity.
—Oliver Wendell Holmes Sr.

We live in an increasingly complex world, a world in which understanding and integration have never been in greater demand. Family systems have only become the topic of rigorous study since the mid-20th century. Understanding the developmental trajectory of each person involved in these systems is even more nascent. Combine these painfully early understandings with the explosion of wealth and its attending requirements of professional support and compliance, and the result is mind-bending complexity.

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If that wasn’t enough…

The brain weighs only three pounds, yet it is the most complex object in the solar system.
—Michio Kaku

The complexity of the human condition must be considered when dealing with these systems. We must understand ourselves if we are to share that understanding with others. We must understand others if we are to learn and work with them.

Coherence must rise out of complexity. Systemic coherence is founded on individual coherence. We are only as available to others as we are available to ourselves.

Experience

We cannot solve our problems with the same thinking we used when we created them.
—Albert Einstein

There are two frames of experience that apply to these systems:

  1. The experience of those we seek to serve
  2. Our experience

The Experience of Those We Seek to Serve

Never in the history of the planet has such wealth been amassed. Never. In the United States alone, $124 trillion will change hands between now and 2050. As a people and society, we have no idea how to deal with this tsunami of need. Failure rates are catastrophic.

Further, the situation in which each family finds itself is unprecedented. Tolstoy was wrong. This quote is found everywhere in succession literature:

All happy families are alike; each unhappy family is unhappy in its own way.
—Leo Tolstoy, Anna Karenina

Every family must find its own way and every family experiences happiness and unhappiness. Appealing to the experience of others can only facilitate learning—imitation simply doesn’t work. Said another way, no family is prepared for a situation it has never before encountered. The skills required to build a business are different from the skills required to pass it along or receive it. It is akin to learning to ride a bicycle all over again, scraped knees and all. These skills must be learned. They cannot be delegated. Two Stewards cannot help those seeking to delegate the living of their lives.

Our Experience

Nothing fails like success.
—Oscar Wilde

We have lived (and are living) the trauma of wealth transition, centered on enterprise creation, operation, and succession. After searching high and low for “certified” support and then on to non-certified support, we have experienced the dearth of professional know-how.

Two Stewards’ structure and tools are the product of 20 years of work. Of all our strengths, the greatest is our willingness to accompany our clients on their journeys. For those who are prepared to press on with their own work, what we offer is transformational. For those seeking someone to undertake their journey for them, we are not a good fit. Two Stewards is not a delegation target. The expert model can only support. It cannot lead.

No two journeys are the same. There’s nothing routine about any of it. It is as scary for us as it is for those we seek to serve. We, with our clients, learn to use fear—and all other senses—as information.

Judge a man by his questions rather than by his answers.
—Voltaire

We believe that real progress stems from curiosity, from asking the hard questions rather than settling for easy answers. At Two Stewards, we walk alongside those who are willing to engage with the difficult questions, who see that success requires navigating not just the complexity of wealth, but the complexity of humanity itself, starting with themselves.

If you can’t explain it simply, you don’t understand it well enough.
—Peter Drucker

Our approach is built on this belief: simplicity and understanding must emerge out of engagement with complexity, not avoidance of it. Our experience is a testament to this journey—working through the dense thicket of complex systems and personal stories to find a coherence that is both practical and deeply human.