Money Can Be a Glue or Solvent, with Gregory Roll

In this episode of Money Tales, our guest is Gregory Roll. What happens when parents tell their two children they can afford to send only one of them to college—so they aren’t going to send either? Greg shares how this pivotal family moment became a guiding lesson for his future money conversations and decisions, especially within his own family. This milestone 250th episode of Money Tales is all about fairness and family dynamics.

Greg is, above all else, curious. An optimistic agent of change, he is a champion of the principle “Show, don’t tell,” and a firm believer in the power of creativity and clarity to drive transformation. Whether summiting mountains or navigating complex business terrain, Greg approaches challenges with a spirit of exploration—always seeking new paths to insight and innovation.

A passionate brand strategist, Greg believes that in today’s crowded and often commoditized investment and wealth management landscape, differentiation is not a luxury—it’s a necessity. As the needs of high-net-worth individuals and families grow in sophistication and complexity, so too must the strategies that serve them. Greg is dedicated to helping entrepreneurs, founders, and business leaders define and execute brand and growth strategies that set them apart and support purposeful, sustained growth.

Greg’s career has been devoted to crafting growth strategies for many of the nation’s most prestigious multi-family offices and leading RIA firms. He brings deep experience working with multi-generational families, focusing on the complex dynamics at the intersection of family, enterprise and wealth. His work often involves direct engagement with high-net-worth families to understand the key factors influencing their decisions around wealth management, investment strategy and family office services.

He has developed particular expertise in data aggregation and consolidated wealth reporting and keeps a close eye on emerging technologies and platforms reshaping the industry. As a management consultant, Greg has partnered closely with a wide range of trusted advisors, including estate attorneys, CPAs, philanthropic strategists and family governance consultants.

Greg is a frequent presenter at industry events hosted by Family Office Exchange, Family Wealth Alliance, and Worthy Circles. He also plays a behind-the-scenes role in shaping thought leadership initiatives for MFO and RIA firms launching their own events for families and advisors. He serves as an Advisory Board Member to StoryKeep and Tapestry, two specialized providers supporting high-net-worth families and is a longtime judge for the Annual Family Wealth Report Awards.