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LESSON: Overcoming extreme adversity often demands we make one or numerous pivotal decisions. Yet, if throughout our life we take on challenges others shy away from, and we build as much character and positive success in our memory bank as possible, we may have enough courage to make that truly existential decision we always hoped we could handle. These prior training grounds give us the confidence and energy to be the leader we always hoped we could be.

The below lesson is an excerpt from my upcoming book, When Not If: A CEO's Guide to Overcoming Adversity, Forbes Book, January 2024.

Now that I had lost my billion-dollar firm, rejected three plea offers, and was sentenced to fourteen years in federal prison, I knew I would have to hold on to some form of hope. Focusing on my shame, regret, guilt, and self-pity would accomplish nothing. Worse, it would hold me back. I saw much evidence of this among my fellow inmates. Those who wallowed in their predicament usually gave up and instead of doing the time in a constructive way, they let time do them. And take my word for it, time in prison is a punishing superintendent.


It’s true the prison administration is set up to strip inmates of any power or agency they might possess. I understood that only massive, positive forward progress daily, with a trajectory I did not, necessarily, yet understand, would remedy the pain I had caused by my horrific series of failures. It was like swimming against the tide. Massive riptides could drown me at any time.


When I was the CEO, my goal was to hire and lead only the most qualified professionals. I understood that if I were going to be able to hire and lead A-Players, they would only follow someone they felt to be equal to or stronger than themselves.

I had several quotations ready for any occasion. “Leadership by example is the only leadership which still works in this world,” was my favorite.


As the CEO, I usually got to the office before anyone else. I wanted them to see my car in the parking lot as they drove up. I made coffee for everyone in the office in part to demonstrate that the CEO was not above kitchen duties. I wanted to model a style of leadership they would accept as stewardship in that my main goal was to walk the walk and do everything possible to be a positive example.


As I now had years behind bars to think about it, perhaps some aspects of the corporate culture I was determined to cultivate were over the top. For example, at the firm’s annual retreats, I and my president Steve would wake up the newcomers at 3:00 a.m. and challenge them to push-up contests. This after the entire team had a rollicking night with stupendous consumption of food and drink. I was determined to demonstrate the leaders were stronger and more capable than the rising wolves who we were convinced they would soon challenge for the right to lead the pack. I couldn’t silence the mantra the strength of the pack is the wolf, and the strength of the wolf is the pack.


Others may say my behavior was too competitive. Looking back on it, I’d have to agree. When having the privilege to recruit successful financial advisors from UBS, Morgan Stanley, and Merrill Lynch, I ensured, outside of my CEO role, that my personal book of business always surpassed everyone else to gain the respect of overachievers we desired to recruit. Every time a teammate whined that the work–family balance prevented them from hitting their target, I pulled out my list of every sports team I was currently coaching for my son and the vacations I had recently taken with my family.


It may have been over the top, but I now realize this previous training and competitiveness is what saved me, my family, and my stakeholders.


Now, in a completely different environment and experiential journey, I knew I had to lead myself, and in turn, I could possibly lead so many others to better outcomes. I quickly learned that, at a minimum, just helping other colleagues have hope gave me incredible power and hope to help myself. Courage is contagious. But I also remembered, talk is cheap, and everyone can be motivated for a sprint. I had the marathon to conquer.


Filing over 300 motions and petitions for other inmates, and then over 500 for myself over 7 years, is the only thing that, by a series of seeming miracles, reversed the court’s decisions, released me from a higher-security violent prison, and sent me home to rebuild for everyone.


Take on every challenge you can possibly handle this week.  Then take on even more next week.  You will get stronger and stronger - mentally, physically, and emotionally.  And when your black swan arrives, you will be ready!


Have a great week!




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