Home Insights Member & Chair Insights [Register Now] Critical Relationships: Navigating Family, Influence, and Control Across Generations

[Register Now] Critical Relationships: Navigating Family, Influence, and Control Across Generations

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TIGER 21

Published On

April 28, 2026

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Member & Chair Insights, Family Office, Webinars, Family & Legacy Planning

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Date/Time:

May 28, 2026

11:00 am ET | 4:00 pm BST | 7:00 pm GST

For many ultra-high-net-worth families, true complexity doesn’t lie in portfolios. It’s found in the people—and the interpersonal dynamics that shape decisions, and, ultimately, define legacy.

While investment strategy often takes center stage, it rarely addresses the deeper questions: Who is in the room making decisions for the family? And how are those relationships being managed?

Join TIGER 21 Family Office Chairs Gil Bonwitt, Heather Gilker, and Christopher Rose for a candid conversation drawn from real insights within the TIGER 21 community of ultra-wealthy investors, entrepreneurs, and single-family office principals, who come together to work through these challenges.

They’ll discuss:

A powerful metaphor for defining who belongs among the decision-makers in your family, who doesn’t, and how to manage those relationships.

How to establish a dynamic that allows all family members to feel seen and heard, without diluting the family’s ability to take action.

Where family relationships most commonly break down—including the timing failures and unspoken expectations that create conflict between generations.

How to recognize overlooked relationships that can have outsized influence on family alignment.

What to consider when navigating generational transitions, including when—and how—to prepare the next generation for stewardship.

Signals that indicate readiness (or resistance) as NextGens step into leadership roles and responsibilities.

Join us for this close look at the human side of multi-generational wealth—and the relationships that either sustain or strain it. You’ll discover how intentional relationship design can support stronger family dynamics, clearer decision-making, and a more enduring legacy.

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Panelists:

Heather Gilker, TIGER 21 Family Office Chair

Heather Gilker is founder and principal of Tokalon Advisors LLC, and Managing Director of Pickwick Capital Partners. She has over 30 years of experience in investing, community involvement, and strategy, with an emphasis on sustainability for families of wealth and impact startups. Heather has worked extensively with family offices, both as a portfolio manager and as a regional executive for Fidelity Family Office Services. She continues to advise families on bespoke projects. Heather also supports the startup community as the North Texas Chapter lead for SWAN Impact Network and serves on advisory boards at FUMC Dallas, the Center for Brain Health, and Southern Methodist University (SMU).

Gil Bonwitt, TIGER 21 Family Office, Fort Lauderdale, and Miami Chair

Gil Bonwitt brings a principal’s perspective to family office leadership and multigenerational wealth stewardship. As a principal of The Scheck Group, a multigenerational family office focused on private equity and real estate, he is deeply involved in governance, capital allocation, deal structuring, and philanthropic strategy—aligning legacy capital with long‑term values and civic purpose. With more than 30 years of experience building, scaling, and advising operating companies and mission‑driven organizations, Gil draws on a foundation in accounting, finance, and law, paired with decades of entrepreneurial leadership. His background informs his work in liquidity planning, succession strategy, governance design, and disciplined capital deployment. He brings practical insight as both a family office principal and operating executive, navigating the complexities of wealth creation, preservation, and transition.

Christopher Rose, TIGER 21 Family Office Chair

Christopher Rose brings extensive experience advising ultra-high-net-worth families on family governance, cross-border investments, and the development of family office strategies. Chris previously led both the Family Office and High Net Worth and Venture Technology practices for Dentons, the world’s largest law firm, in Europe and the Middle East. Recognized by Chambers Europe as a “towering figure” in private equity and venture capital, Chris has advised on over 300 transactions globally. He is also a trained mediator, having studied at Harvard Law School’s Program on Negotiation. A long-standing member of YPO, Chris currently sits on the organisation’s Global Board of Directors. Drawing on a career that combines deep transactional experience, legal expertise and extensive work with global families, Chris is uniquely positioned to help family office principals address the challenges of governance, succession, and wealth preservation across generations.