Bold, audacious, has own moral compass. Ok with ethical gray areas such as tax evasion and screwing over big companies, but not people. Cares about the person, able to overlook the people. Filled with a spirit of adventure and wanderlust.
Was not strategic at early life, just chasing adventure and relying on his wits - put himself out there with immense chances to become lucky and he eventually did. His entire fortune was built on exploiting arbitrage which began when he chose to exploit a roulette table scheme in Reno instead of taking a job after graduating from Cornell.
Then moved to Europe on a whim and pursued a grad degree in France that enabled him to keep adventuring. Stumbled upon arbitrage opportunities to resell due to his connections. Mulled his network well - so many of partners came from Cornell or met after reading the Cornell alumni newsletter to see who was in the parts of Europe that he was living in at the time.
Constraints create creativity - Chuck found this great arbitrage opportunity to sell duty free liquor sales to military due to esoteric regulations, that expanded to cars and tobacco as his business grew. So much of his success came from taking advantage of weird taxes and duties and exploiting them with tax havens from Lichtenstein to France to Spain with unauthorized businesses. Same with the case of recognizing currency arbitrage with Japanese tourists during the 80's boom, before recognizing the domestic opportunity for duty free, especially through Hawaii. He capitalized on expansion of the Asian tigers with trade and prosperity in Hong Kong becoming central to his business.
Key to Chuck Feeny's life was anonymity. From his early days as a hustler, he recognized that publicity would not be in his service. And he had the adventurous mentality and self-awareness to recognize that the spotlight would be more of a hindrance to him than a benefit going through to his days running DFS. By the time he was a billionaire, it was impossible for him to avoid publicity due to his donations to resolve the conflict with the IRA, philanthropy in building modern health in Vietnam, and $1B given back to Cornell. Amazing to hear about the incognito meetings that he held with David Skorton about the $350M donation given to build Cornell Tech. I remember vividly when Cornell was in the running for this, and to hear how impactful Chuck's underground efforts were is a modern mark on history that is was close to me. And of course General Atlantic - learning the story of George Parker who handed me my diploma from GSB makes me wish I had read this earlier to be able to ask about stories behind the scenes.
The other legacy of his story is how business success affected relationships. His closest partners that he began with who were the ones he trusted and genuinely enjoyed breaking into new adventures with when he was younger drifted apart as friends - a common thread throughout his businesses. Building his billions led him to realize the why in his life, and followed the mantra that managing success is harder than managing failure.
Chuck Feeny was both strong and powerful. Strong enough to recognize that strength was more important to power, and powerful enough to wield it when he needed to exert his influence. He had an immense ego, but was not driven more by adventure and experience than ego. He clearly was driven by ego as well, evidenced by his outwardly stated intervention with Sinn Fein and Limerick University. What I question is how did he choose what to care about?
I recognize the need for choice - what to dedicate your passion to, who to love. There are limited hobbies, limited people that you can choose to dedicate your time to. Wealth for Chuck meant being able to care for what he loves. How did he choose Ireland, Vietnam, Queensland?