
Episode #39
Embracing a 'Left of Loss' Risk Management Mindset With Robert Raymond
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.






