In this episode of 'The Wisdom Of' Show, host Simon Bowen speaks with Ron Diamond, Founder and Ceo of Diamond Wealth. From investing alongside 100 family offices to chairing multiple TIGER 21 chapters, Ron brings decades of experience in wealth management, philanthropy, and private markets. Discover his insights on the true purpose of wealth, the transfer of family legacies, disruptive technologies, leadership evolution, and the five principles that guide his life and decisions.

Ready to elevate your leadership approach? Join Simon's exclusive masterclass on The Models Method. Learn how to articulate your unique value and create scalable impact: https://thesimonbowen.com/masterclass

Episode Breakdown

00:00 Introduction and Ron's extensive background in wealth management

05:24 The origin story: From Drexel Burnham to entrepreneurship

08:50 Loyalty to people versus loyalty to companies

12:30 The evolution of family offices and wealth transfer statistics

16:45 Philanthropy as problem-solving: The Michael Milken approach

22:17 The Five Most Important Things: Ron's life philosophy

29:40 AI and technological disruption in investment strategies

38:50 Leadership evolution: From ego to vulnerability and authenticity

44:10 The governance gap: Why family wealth doesn't survive generations

49:22 Mentoring the next generation and paying it forward

55:16 Final reflections on gratitude and authentic success

About Ron Diamond

Ron Diamond is the Founder and CEO of Diamond Wealth, investing alongside 100 Family Offices ranging in size from $250 million to $30 billion. Diamond Wealth focuses on private markets including private equity, venture capital, and real estate.

Ron serves on numerous advisory boards and chairs multiple TIGER 21 chapters in Chicago. He is the past Chairman of the Advisory Board for the Disruptive Technology and Digital Cities Program at Stanford University, where he also taught entrepreneurship and helped create the Stanford Family Office Initiative.

As a frequent speaker at Family Office and Alternative Investment Conferences globally, Ron has shared his expertise at over 100 events worldwide. He is also the Founder, Host, and CEO of Family Office World Media, providing an informational platform for Family Offices to collaborate, upskill, and innovate in an unmonetized environment.

Earlier in his career, Ron founded Pinnacle Capital, a $250 million hedge fund that outperformed the S&P index for ten consecutive years before being acquired by an international investment firm. Deeply committed to philanthropy, Ron serves on the Leadership Circle of the Aspen Institute and on the boards of various charitable organizations.

Connect with Ron Diamond

LinkedIn: https://www.linkedin.com/in/ronalddiamond/

Website: https://www.diamondwealthstrategies.com

Family Office World Media: https://www.familyofficeworldmedia.com

About Simon Bowen

Simon has spent over two decades working with influential leaders across complex industries. His focus is on elevating thinking in organizations, recognizing that success is directly proportional to the quality of thinking and ideas within a business. Simon leads the renaissance of thinking through his work with global leaders and organizations.

Connect with Simon

LinkedIn: https://www.linkedin.com/in/simonbowen-mm/

Instagram: https://www.instagram.com/officialsimonbowen/

Website: https://thesimonbowen.com/

Get Simon Bowen's Personal Newsletter for Leaders, Thinkers, and Entrepreneurs! 👉 Sign Up Now: https://thesimonbowen.com/newsletter

Join Simon's Masterclass: Unlock your leadership potential with The Models Method. Learn to articulate your unique value and create scalable impact.

👉 Watch it Now: https://thesimonbowen.com/masterclass

2025-06-04- KSR - Hour 2