FOXcast

Today, I have the pleasure of speaking with Teresa Chope and Connor Gribbon of Gallivant, a luxury travel and lifestyle advisory firm serving ultra-high-net-worth families. Teresa is the Founder and CEO of Gallivant. After a successful career as an executive in the biotech and pharmaceutical industries, she recognized that family travel was often missing the depth of engagement and personalization needed to create meaningful shared experiences. More than twelve years ago, she founded Gallivant on the belief that travel is one of the most powerful tools families can use to build human capital, strengthen relationships, and foster a shared sense of purpose across generations.

Connor leads strategy and partnerships at Gallivant. He began his career in luxury real estate before earning his MBA from Columbia Business School and pursuing his passion for bespoke travel. At Gallivant, he works closely with client families, supports rising-generation engagement, and helps cultivate partnerships across the wealth advisory, multifamily office, and family office communities.

Teresa and Connor discuss the evolving landscape of luxury family travel and the trends reshaping how enterprising families approach travel experiences today. They explain how families are increasingly seeking purposeful, highly personalized travel that goes beyond recreation and serves broader family objectives.

A central theme of our conversation is the role of travel as a tool for family engagement and development. Teresa and Connor explain how thoughtfully designed travel experiences can strengthen family bonds, foster communication, expose rising-generation family members to new perspectives, and help families create lasting memories and shared values.

One practical tool they highlight is the Gallivant Mosaic, a visioning and planning framework designed to help families align travel experiences with their goals, interests, and aspirations. They also share practical recommendations for family principals, family office executives, and trusted advisors on how to plan and leverage travel as a catalyst for purpose, connection, and togetherness.

Enjoy this insightful conversation with two leaders in luxury family travel on how families can use shared experiences to strengthen relationships, engage the rising generation, and build family capital across generations.

Today, I have the pleasure of speaking with Robert Raymond, First Vice President and Risk Strategist at HUB Private Client, a privately held personal insurance brokerage firm serving ultra-high-net-worth clients. Bob is an award-winning expert in multigenerational risk management, working with families, their advisory teams, and key stakeholders to help eliminate balance sheet exposure to negative liquidity and other preventable risks.

Bob currently serves as a member of HUB's National Private Client Council and Chair of its Technology Sub-Committee. Prior to joining HUB, he served as Assistant Vice President with Marsh Private Client Services, where he advised international family offices. Throughout his career, Bob has combined deep expertise in risk management with a passion for helping families take a proactive approach to protecting their wealth, assets, and legacy.

Bob introduces the concept of being "left of loss," a risk management philosophy that encourages families to anticipate and address risks before they become costly problems. He explains why proactive planning is often more effective than reactive solutions and outlines how families can build a culture of preparedness across their enterprises and households.

A key theme of our conversation is the broad spectrum of risk management strategies available to families and family offices. Bob discusses why insurance is only one component of a comprehensive risk framework and explores the role of advisory services, self-insurance strategies, governance practices, and other tools that can help families protect both financial and non-financial assets.

Bob also shares practical guidance on managing the increasingly complex risks facing today's families, including property, liability, and cybersecurity concerns. He highlights actionable tools, checklists, and resources that families and their family offices can utilize to strengthen their risk management programs and improve resilience in an evolving environment.

Enjoy this insightful conversation with a leading risk management strategist on how families can embrace a proactive mindset, expand their risk management toolkit, and better protect their assets and legacy for generations to come.

Today, I have the pleasure of speaking with Karen Harding and Stacey Flier of NEPC, a full-service investment consulting firm serving governments, institutions, families, and individuals. Karen is a Partner and Team Leader of NEPC's Private Wealth Team and serves on the firm's Governance Board and Women's Leadership Forum. Prior to joining NEPC, she spent twenty-one years at CTC | myCFO and its predecessor companies in a variety of leadership roles, and previously worked as a Senior Analyst and Investment Manager Specialist at R.V.K.

Stacey is a Principal and Senior Consultant at NEPC with more than 25 years of experience advising private wealth clients and family foundations on investment portfolio strategy. Before joining NEPC, she served as Director of Investment Advisory Services at CTC | myCFO and earlier worked as an Employee Benefits Analyst at U.S. Bank. Stacey is a Chartered Financial Analyst and is actively involved in several professional and community organizations focused on investment management and governance.

Karen and Stacey share their perspectives on how the investment needs, preferences, and expectations of families and family offices have evolved over the years. Drawing on decades of experience advising ultra-high-net-worth families, they discuss the growing complexity of the investment function and the increasingly sophisticated approaches families are taking to achieve their objectives.

A key theme of our conversation is the institutionalization of investment management within family offices. Karen and Stacey explain how this trend is reshaping the way families organize their investment activities and evaluate the outsourced CIO, or O-CIO, model. They discuss the benefits, challenges, and considerations involved in determining whether to build investment capabilities internally or leverage external expertise.

The discussion also explores the impact of family dynamics and generational change on investment strategy and governance. Karen and Stacey describe how the values, priorities, and expectations of rising-generation family members are influencing investment philosophies, organizational structures, and decision-making processes across family offices.

Enjoy this insightful conversation with two experienced investment advisors on how families can align their investment function, governance, and mandate with their long-term goals and evolving needs.

Today, I am delighted to speak with Donald Cunningham, Head of Family Office and Chief of Staff to a senior member of the Qatari royal family. Donald is a family office executive, advisory board member, and trusted confidant with more than 20 years of professional experience spanning single-family offices and investment banking. Over the last twelve years, he has advised ultra-high-net-worth principals and their families, leading operations and multidisciplinary teams, overseen both portfolio and option-value assets, and managing complex projects across multiple global jurisdictions.

Donald has held senior leadership roles in prominent family offices in London and New York, where he advised principals on strategic operations and helped build and lead high-performing teams. He began his career in capital markets and special situations M&A, and his experience combines a strong foundation in banking, hands-on operating experience within family offices and portfolio companies, and a proven ability to cultivate trusted relationships.

Donald shares his insights into the unique psychology of wealth owners and family principals, drawing on years of experience working closely with some of the world's most prominent and influential families. He discusses the cultures these principals create the opportunities and challenges that arise within those environments, and the qualities that distinguish successful family office professionals.

A central theme of our conversation is the importance of matching talent to the principal's culture. Donald explains why technical expertise alone is often insufficient in a family office setting and outlines the characteristics, competencies, and personal attributes that contribute to a successful fit between principals and key employees.

Donald also offers practical guidance for both principals and candidates navigating the hiring process. He highlights the importance of asking the right questions to assess cultural fit and shares his recommendations for evaluating whether a working relationship is likely to succeed. In addition, he discusses the role of face time and personal interaction in building trust, developing strong instincts, and fostering long-term professional success.

Enjoy this insightful conversation with a seasoned family office executive on the art of aligning talent, culture, and leadership within the unique world of enterprise families and family offices.

Today, I have the pleasure of speaking with Jeff Jones, family recovery coach, author, speaker, and founder of The Family Recovery Solution. Unknowingly, Jeff grew up in an addicted family system and never forgot the experience. This inspired him to earn a master's degree in couples and family counseling and pursue numerous counseling and life coaching credentials. Throughout his career, he has focused on two questions: "How do people actually get better?" and "How do families contribute to the solution?" In his latest book, Rethinking Addiction: The New Family Recovery Solution, he answers both questions and introduces a three-phase program for families with a member in active addiction or early recovery.

Jeff describes the realities and challenges families face when a loved one struggles with addiction. He outlines the emotional, relational, and practical issues families must navigate and explains why addiction should be viewed not only as an individual challenge, but also as a family system issue. He also compares traditional approaches to addiction treatment with his Family Recovery Solution, highlighting the advantages and shortcomings of each.

One practical recommendation Jeff emphasizes is the importance of having structure. He explains how healthy boundaries, clear expectations, communication practices, and support systems can help families move from crisis management toward a more constructive recovery process. Jeff shares practical guidance for families seeking to support a loved one while also protecting their own well-being.

Another important topic Jeff discusses is the range of resources and programs available to families dealing with addiction. From treatment and recovery programs to family-centered coaching and education, he explains how families can identify and utilize the support systems best suited to their circumstances.

Enjoy this insightful conversation with a leading family recovery expert on one of the most challenging issues families face today and learn how families can play a vital role in helping loved ones manage and overcome addiction.

Today, I am delighted to speak with Cory Klippsten, Founder and CEO of Swan, a financial services company that focuses exclusively on Bitcoin. Cory is an investor or advisor in more than 50 technology startups and was named to the Top 500 Most Influential list by LA Business Journal in 2024 and 2025. He is a partner in Bitcoiner Ventures, El Zonte Capital, and The Bitcoin Opportunity Fund, and as an angel has funded more than 60 early-stage tech companies.

Before startups, Cory worked for Google, McKinsey, and Morgan Stanley, and earned an MBA from the University of Chicago. He is a frequent guest and contributor to tech, financial and Bitcoin media. Recent appearances include CNBC, Bloomberg, Barrons, The New York Times, and Yahoo! Finance.

Cory explains how Bitcoin features in the asset portfolios of UHNW families and family offices today and how their attitudes and exposure to this foundational digital asset have evolved over the past few years. He also comments on how Bitcoin compares to or stands out from other digital assets families are considering or investing in.

In the grand scheme of things, Bitcoin is still a relatively new asset, and many investors are still coming up the learning curve on how to invest in it. Cory talks about where Bitcoin is today in its maturity curve and its progression from a frontier digital alternative to an established, mainstream asset class.

Cory offers his views on the best tools and platforms for families and family offices to become educated on Bitcoin and to keep up with the latest trends and development in this avant-garde space. He describes the products and providers family offices should consider when investing in Bitcoin and participating in the continued ascendance of this and other major digital assets.

Don't miss this fascinating conversation with a prominent Bitcoin pioneer, innovator, and entrepreneur.

Episode Resources from Cory Klippsten

• "The Bullish Case for Bitcoin" article
• Vigil Protocol family financial orchestration (complimentary trial for FOX listeners)
• "Welcome to Bitcoin video" series
• "Inventing Bitcoin" book
• Stephan Livera "Intro to Bitcoin Austrian Economic Thought"
• "Broken Money" book by Lyn Alden

Today, I have the pleasure of speaking with Esther Greenhouse, CEO of Silver To Gold Strategies, a financial gerontology consultancy working at the intersection of economics and aging. Esther is an environmental gerontologist and longevity strategist. Her work at Silver To Gold Strategies equips financial planning firms to reduce preventable caregiving risks and costs.

Esther applied her unique Enabling Design Method™ to help her mother delay a move to a care facility by 7 years, maintaining dignity and legacy and saving a considerable amount in estimated costs. She has worked on visionary projects, such as the U.S.'s first elder-focused ER, co-created a multiyear initiative for AARP International, served as the strategic director for the nation's first Age Friendly Center for Excellence, and created and taught a course on her unique method at her alma mater, Cornell University.

Esther describes the realities and challenges families face as some of their family members enter their golden years and are choosing to age in place and talks about what this transition means for the families, their caregivers, and their advisors. She outlines how families should be planning for this stage of life and identifies the developments and decisions they will face across so many areas of their life – from home design to finances to the psychology of aging and caregiving, to mention just a few.

One practical consideration – and a difficult one to discuss – is how to design the home environment around the personal hygiene needs of the family member and support their independence and dignity. Esther shares her tips on what families and family offices need to think about to achieve this goal.

Another practical dimension Esther talks about is for families to develop and execute intentional longevity planning and strategy that includes generations and encourages all the difficult conversations, while providing the practical solutions families need. Can you elaborate on this.

Enjoy this instructive conversation on an important, yet difficult topic with a leading expert in the field of longevity and gerontology.

Today, I'm excited to speak with Chris Demaillet. Chris spent 18 years working as a private chef for some of the world's wealthiest families: on yachts, in residences, and across the globe. He founded Montclair Chef to help clients find world-class Chefs such as himself and the culinary masters he's worked with and trained.

Before private service, Chris trained in France and worked in several of the world's best kitchens, including a 3-Michelin-star restaurant once ranked among the top 25 globally. That experience, which was the culinary equivalent of being a professional athlete, taught him what precision, discipline, and world-class execution really mean.

Now, he runs Montclair Chef with that same mindset: placing elite private chefs into ultra-luxury homes and superyachts, with the standards and care of a Michelin kitchen. Chris is the author of The Private Chef Guide - How to Become a Private Chef and Build a Career in Private Dining.

We start with an overview of the world of private culinary services. Chris explains how the need for a personal chef normally arises and when it makes sense for a family or a family office to consider employing a private chef. He describes what UHNW clients and families look for in a private chef and outlines the most common needs and preferences of UHNW clients when they are considering or working with a private chef.

For families who are considering private culinary services, Chris offers his tips on how to find and hire the right private chef. A personal chef can become an integral part of the family's household and everyday life. Chris provides some practical suggestions for families and their family offices on how to retain their chef for many years and what they need to do to take good care of their chef.

Enjoy this informative exchange with one of the best connected and most experienced advisors in the world of private culinary services for UHNW individuals and enterprising families.

Today, I have the pleasure of speaking with Sherri Helmond, Accounting & Financial Outsourcing Director, Equine Industry Leader at Dean Dorton. With more than 30 years of executive management experience, Sherri brings a unique blend of operational leadership, financial expertise, and industry insight to her role as Dean Dorton's Equine Industry Leader. As Equine Industry Leader, she works closely with clients to align financial strategies with the unique demands of the industry.

Sherri's areas of expertise include business planning, financial analysis, forecasting, and outsourced accounting. She is particularly skilled in implementing technology solutions, including Sage Intacct, to streamline financial processes, enhance reporting, and deliver actionable insights that support sustainable growth. Since joining Dean Dorton in 2019, Sherri has specialized in serving equine clients, leveraging her CFO-level expertise to help farm owners, trainers, and equine businesses strengthen operations, improve profitability, and plan strategically for long-term success.

Sherri and her firm, Dean Dorton, are an Advisor Member of FOX, and we are thrilled to have her expertise and thought leadership within our membership community.

We start with Sherri's views on where equine ownership sits in the bigger picture of an enterprise family's life and investment portfolio. She describes the different reasons and models for a family and their family office to be involved with breeding and owning horses.

There are many segments within the equine industry. Shery elaborates on how a family should evaluate and select the right segment, and how they should engage with all the industry players within their chosen segment of equine ownership.

One practical consideration for families who are passionate about owning or investing in horses is all the specialized expertise they need to be successful in this niche endeavor. Sherri offers her advice on how families and their family offices should assemble the right team of advisors with deep and relevant expertise in the equine space.

Do not miss this illuminating conversation with one of the foremost equine experts serving UHNW families and their family offices.

Today, I am pleased to welcome Edward Marshall, Founder and CEO of Presage Global, an intelligence-powered risk and business advisory firm serving C-suites and boards, family offices, and investors. Eddy is a family office insider and a leading family office researcher, advisor, and author. He is also a risk and threat management specialist, working with families to reduce their cyber, physical, financial, operational, and reputational risk profiles.

Eddy is a member of the Advisory Board and co-heads the Family Office Initiative at the UHNW Institute. He co-authored the book, The Family Office: A Comprehensive Guide for Advisers, Practitioners, and Students. Prior to founding Presage Global, Eddy held leading family office roles at Dentons, Credit Suisse, Citibank, and Boston Private.

Eddy has been in the family office industry for a while now and recently released a joint study with Nines on the state of the family office estate security. He shares his view on what's happening in the family office security space and what's changed in the past decade or so.

Eddy provides a synthesis of the overall risk situation facing most family offices, explaining why family offices at risk and what are the major risks they face. He offers his thoughts on whether most family offices are being proactive or are reacting to risks only after a major threat or failure.

Eddy talks about risk management as a cross-domain field and one practical tool he and his firm have put forth is the Ten Domains of Risk framework, which includes elaborate checklists for family offices across multiple risk areas. He describes the framework and shares how family office leaders can apply it in their everyday work.

Eddy works with many family offices and as he looks across all these different cases he has assessed in the past few years, he summarizes the top three things he believes family offices can change to improve their risk management posture and capabilities.

Enjoy this highly relevant conversation with a family office industry veteran and risk management expert serving UHNW families and their complex enterprises.