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The Deeper Dive





I have spent the majority of my adult life pursuing two parallel life tracks, each with passion, commitment and effort. I have spent over 30 years as a professional investor charged with managing large private and institutional portfolios with the singular objective of generating consistent returns above industry benchmarks. My style was based on deep fundamental company research, frequent company communications to constantly update my assumptions, relatively few investments to ensure focus, and a relentless examination of risk – the real job of a good money manager. I was fortunate to work in many different work environments, with many different types of clients, in a broad range of market conditions. I managed money in the crash of 1987, the collapse of Long Term Capital Management, the bursting of the tech bubble in 2000 and the great financial crises of 2008. In each case my clients’ capital remained intact.


During this period of professional pursuit I invested an equal commitment of heart and mind working for those less fortunate. I spent many late nights at call centers offering help to those negotiating dark times and darker choices, I volunteered with the Special Olympics, I tutored students in math and English, I served as a mentor, I coached basketball in uptown rec centers, and I created the “American Dream Project.” This undertaking was one of the early nationally recognized mentoring programs. We paired educationally challenged students from public schools in Harlem and students from the “I Have A Dream” program with some of the largest and most influential businesses in New York City. This project gave my wife and me the rare opportunity to influence the lives of over 400 students, helping many advance their educations, find jobs and broaden horizons. Charity and service continue to be an integral part of my life. But nothing comes without a cost.


Over the past ten years I have devoted a large part of my energy and effort trying to reconcile the pain and suffering caused by these two very different, and often times conflicting, pursuits. Why was I compelled to stay connected to a life of service that proved to undermine many of my professional aspirations? The deeper I dove the clearer became the water. I had a problem with trust and it was tearing me apart. All the important decisions in my life were guided by my attitudes and predispositions toward trust and I was completely unaware of this powerful connection. But if I wanted to solve for trust, I needed to learn more, and that is how I became aware of the heartbeat of trust, expectations. Without a clear awareness of the expectations held by all involved in any decision, experience or transaction, durable trust is simply not possible. It is our expectations that lead us to judge a choice smart, an accomplishment meaningful, a connection trustworthy and a life well lived.


I wrote the book “The Meaning of Trust and the Power of Expectations” to help individuals, groups and organizations address these two essential subjects. I am now looking for opportunities to help others capitalize on what I have learned.