The Human Side of Wealth — 5 Insights I Learned from Ron Diamond

Family Offices are private wealth management advisory firms that serve ultra-affluent families, offering a wide range of personalized services from investment management to philanthropic planning. With an estimated $10 trillion in global assets, Family Offices are a growing source of patient capital and strategic guidance for entrepreneurs.

A quick search for Ron Diamond will reveal TEDx talks, keynote speeches and podcast episodes where he discusses the evolution of Family Offices, the importance of trust and integrity, and strategic philanthropy.

Having worked closely with Ron Diamond, I’ve gained unique insights into the man behind the thought leadership.

His story covers a range of experiences, from his early influences and corporate beginnings to his impactful mentorships and ongoing commitment to education and community engagement.

1. Balancing legacy with humility

Ron was born and raised in Chicago, where his father and grandfather served as chairmen of prominent financial institutions like Heller Financial and American National Bank.

While his father and grandfather were highly successful in banking, his father prioritized family time despite his demanding career. He dedicated his weekends to his family, demonstrating the importance of balancing work with your personal life and family.

For Ron, the ability to stay humble and keep one’s ego in check is an invaluable asset regardless of industry. The most important lesson he learned from his father was to work hard and take one’s work seriously while remaining humble.

Related: Don’t Let Your Ego Make You a Controlling Leader. Here’s How.

2. Learning from failure

Ron entered the finance industry right from college. He accepted an offer to join Drexel Burnham in his junior year at Northwestern University. It was the early-mid 80s, and Drexel Burnham was the most profitable firm on Wall Street.

Simultaneously, Ron’s father had just published his first book, “Leveraged Buyouts.” The publication explored the emerging field of what is known today as private equity. “My father wanted me to meet John Canning, who was starting Madison Dearborn — now a top private equity firm globally,” Ron recalled. Despite this opportunity, Ron chose Drexel, drawn by its prestige and the chance to work under the legendary Michael Milken.

The firm faced a catastrophic collapse just two years after Ron joined Drexel Burnham. Ron had a front-row seat, witnessing first-hand the demise of what was once a towering institution and seeing seasoned professionals lose their life’s work overnight. This event deeply impacted Ron’s perspective on the volatility and impermanence of even the most esteemed financial firms. From that moment, Ron decided to place his loyalty in people over corporations. Any firm can collapse, but personal relationships will endure.

Related: The F-Word: Why Failure is a Must-Have Key to Success

3. Influential mentorship: Insights from Michael Milken

Milken’s visionary approach to business and philanthropy, focusing on personal connections over mere transactions, left a lasting impact on Ron, who he saw as brilliant and forward-thinking.

“I would just listen intently in meetings, absorbing his insights like a sponge, recognizing his ahead-of-time brilliance,” Ron recalls.

This deep mentorship shaped Ron’s professional outlook, emphasizing the importance of loyalty and deep connections, values that he has carried forward in his career.

Years later, Milken’s strategic approach extended to his philanthropic efforts, particularly in his innovative response to his prostate cancer diagnosis. Rather than following traditional treatment paths, Milken applied a venture capital mindset to medical research, strategically investing in diverse initiatives to maximize impact.

Inspired by Milken’s model, Ron embraced a similar approach in his ventures, focusing on impactful, strategic investments.

4. The relationship business

Ron’s next move was the founding of Pinnacle Capital. With $3 million raised from friends and family, he quickly grew the firm’s assets to $250 million by its second year. This growth was driven by consistently outperforming the S&P 500, earning the trust and satisfaction of his investors.

In the 1990s, the term “Family Office” was not yet commonplace; Ron’s early investors were simply known as “rich people.” This group would evolve into what is now recognized as Family Offices — private wealth management advisory firms that serve ultra-affluent families. Ron’s transition into the Family Office space was marked by his ability to forge strong, trust-based relationships with his clients, aligning with the Family Office ethos of personal connection and long-term strategic engagement.

Through Pinnacle Capital, Ron not only expanded his influence in the financial sector but also set a foundation for his future initiatives.

Focus on building trust-based relationships and providing personalized financial management. By prioritizing personal connections and long-term engagement, you can achieve significant growth and establish yourself as a trusted advisor in your industry.

Related: How Your Entrepreneurial Spirit Can Lead The Way in Crisis

5. Family Offices: Where prosperity meets purpose

Ron’s approach evolved as he realized that Family Offices prioritize trust and integrity over sheer financial acumen. “With Family Offices, the first thing they want to know is if they can trust me, if I’m a good person. The financial models and strategies come later,” he explained. This shift from transactional to relationship-driven interactions marked a significant transformation in his career.

This marked a shift from transactional to relationship-driven interactions, contrasting sharply with institutional investors, who prioritized financial track records first. After the sale of Pinnacle Capital, Ron established Diamond Wealth.

He drew parallels between his resources and the ability to address broader societal challenges. This perspective was reinforced by observing influential figures like Michael Milken and Bill Gates, who used their resources to tackle grand-scale challenges through innovative, targeted impact investments.

Related: 5 Myths About What It Takes to Become a Wealthy Franchisee

As an active keynote speaker and participant in Family Office conferences worldwide, Ron continues to share his insights and experiences. Notably, his TEDx Talk on Family Offices has further cemented his role as a thought leader in the industry. In addition, Family Office World’s podcast and newsletter provide ongoing insights and updates, fostering continuous learning and engagement within the community.

Ron’s latest venture, Family Office World, was inspired after a pivotal conference at Stanford University in 2019. Ron explains how the success of this event highlighted a widespread demand for knowledge exchange in an industry often burdened by siloed information and inefficiencies.

Upcoming Webinar: Work with Family Offices to raise capital and grow your business

If you’re looking to learn more about how Family Offices operate and learn directly from top industry leaders, don’t miss the upcoming Entrepreneur Workshop on Wednesday, October 30, at 2 PM ET.

Speakers like Ron Diamond, Eric Becker, Pete Kadens and Mike Gamson will share insights on raising capital, making strategic connections, and driving business growth through Family Offices.

Register here to secure your spot.