The Life Choices of Wealthy Men, Part Two


In the ‘90s, I interviewed 17 men who knew at an early age they had some independent wealth. In Part One of this three-part series, I provided the following table on their backgrounds along with information how their parents influenced their life choices and how they dealt with “money issues”.

 Table 1. – Education of Men Interviewed

Parts Two and Three will cover:

  • important early influences from schools and military service;
  • alternate life choice strategies they used and the outcomes;
  • the chance element in the choices they made, and
  • the significance of these men’s experiences for today’s parents and children.

But first, I want to provide a bit more background on the men interviewed. While they were all from wealthy, well-established families, they still had their share of problems. The following bulleted items were included in an unfruitful proposal to a book publisher back in ‘90s. All true.…

  • how sister’s suicide led man to reject career he wanted;
  • various men took over the family enterprise: a shipping company, a biscuit  company, a law firm, and a museum;
  • how the shipping company became the primary compiler of minor league  baseball statistics;
  • how one man who left Harvard twice (never finished), became a  tennis bum but ended up happily running his father’s company;
  • what several did after getting thrown out of Harvard;
  • for several, financial independence created ambiguity and ultimately serious mental problems;
  • how fear of failure caused several to make “safe” career  choices;
  • how some parlayed family status and connections into secularly successful careers;
  • how one turned away from a lucrative career in commercial real estate  to find ways to increase employment in depressed urban areas;
  • how several found being an undergraduate at Harvard completely overwhelming;
  • how one used “getting his mother’s jewels out of a safe” as an excuse  to get a visa to spend a summer in Paris at the end of WWII;
  • how one spent every summer as a child traveling in luxury throughout  Europe with his parents  and never returned;
  • one brought the college paper home with his picture and those of four other people nominated to be class secretary/treasurer; his father’s reaction was: “that is fine: let’s see you get it.”
  • One, an adopted child, became a fashion model at an early age, was gang-raped at a prominent men’s college, never finished college, but ended up becoming the CEO of a  large corporation;
  • one who was blocked from joining an exclusive club because at work he showed up several of its members as incompetent in their jobs;
  • one who left a senior job in a family firm after a decade to return  to business school because he felt incompetent;
  • one, a prep school graduate, chose to be an administrator in the public school system because he viewed prep schools as elitist;
  • one who wished he had not made a career in his father’s law firm  because “it was too easy”;
  • one who gave up an exciting and lucrative opportunity to run a  prestigious newspaper to try a new form of journalism that ultimately failed;
  • one who regrets not using “connections” to be a lawyer at the  Nuremburg trials;

Powerful Educational Experiences

a. Prep School

All were asked where they had their most impactful educational experience – the real wake-up call. The answers ranged from prep school or below to college and for some, the military. Several who boarded at their prep schools fell into a structured existence that they enjoyed. Two had exactly the same educational experience (Dexter, Groton, and Harvard) and they both singled out their time at Groton as special:

  • C8 – “Groton gave me a sense of responsibility;
  • M4 – “Groton was very disciplining and enlightening….I discovered I had some strengths. I came in with the lowest grades. I was jokingly referred to as the anchor man, but by the time of graduation, I ranked 17th out of 40 in my class. Groton was my premier educational experience. Overall, I felt I was a member of the community. Harvard was not focused enough for me.” [M4 got thrown out of Harvard for drinking].

Of the 17 men interviewed, 7 saw their life at prep school as being their best educational experience. C3 is a good example: “Loomis had fine teachers with a profound perspective on life, and the ability to motivate students.”

C4 had a very different view of his prep school experience: “My mother wanted me to go to Nobles because it was close by. It was “a third rate school intellectually. It was a WASP schools with no Blacks, no Catholics or Jews”.

Elliott: I boarded at Milton Academy and the school did nothing for me. I went there because it was one of the first prep schools to have an artificial ice hockey rink. The only reason I cared about grades at prep school was because if you were not on the honor role, you had to go to a public study hall for a couple of hours after dinner instead of going back to your dorm.

b. After Prep School

S4 had a somewhat unusual education: “I was miserable at Taft; I couldn’t wait to get out. There was nobody there who was influential in the usual sense: a Mr. Chips who changes your life. I did like music, and during my three years before Harvard, I spent seven months working with a pianist in Germany.  His name was Franz Wagner, and he was a great concert pianist. He really adopted me. To my consternation, he had me practicing eight hours a day, which today is unthinkable to me, and I still can’t believe it happened. The other thing is he was a great bon vivant; he became a surrogate father. He was enormously influential in bringing me to early maturity. He took me traveling. At the age of 17, I learned something about women and worked my ass off.”

S4 continued: “I was not a great scholar. I had some illusions about becoming a concert pianist. I quickly realized I was not up to it. But music has always been a part of my life. Art had also been important. I tried etching during the summer periods in Rome. When I came to Harvard I was not career minded, I was just trying to have a lovely time and take as many gut courses as I could. I was not good at math or physics, so I barely got into Harvard because I couldn’t pass the college boards in algebra.”

c. College Experiences

For a number of men, the college experience was extremely important.

C2: “Going to the University of Virginia put me in touch with a new group of people. We just didn’t all come from the same prep school. I had Richmond friends and friends from other parts of Virginia. From that point of view, I am much worldlier today. And of course, there was more horseback riding down there.”

For M4, college was problematic: “At Harvard, I took a nose-dive, I had my low beams on. I didn’t have a foggy notion of what I wanted to do. I found it too unstructured, daunting, and confusing. I was a typical preppy; I had all I could do to keep my life together. I had tremendous anxieties that I relieved with alcohol. In my freshman year, being well prepared at Groton, I didn’t have to go to more than 25% of my classes. I did badly but survived my freshman year. I was a savage drinker, full of anger. Finally, I got in fight with a member of the police force and got tossed out. It was not an all- bad experience: the next morning, before going to see Dean of students to get expelled, I vowed to stop drinking for a year and I have never had a drink since.”

At Harvard, he was in the Porcellian Club. M4: “That is a bunch of dinosaurs, an antediluvian group, a socioeconomic pariahdom. While they drank, they didn’t like my public displays. A particularly reptilian member, Theodore Roosevelt IV (known as T4) advised me after a wild night that ‘it reflected badly on the Club’. You could drink so long as you did not get into trouble.”

M4’s parents were not critical of his drinking, but his mother was embarrassed and horrified when he got tossed out of Harvard. His father cared more about him: “Whenever I got in a pickle, he would fly up [he lived in NYC] and help me out. The day I got tossed out of Harvard, father flew up, took me for lunch at the Ritz, and asked if there was anything he could do. He was very helpful. We weren’t very close because father’s second wife was jealous.”

M1 also had a rocky college career: “Williams College didn’t work out: I was gang-raped by a group of men, and never graduated. President Baxter of Williams was a friend of my father’s and used his connections to get me enrolled in Harvard for summer school. That was fun, but I got involved in a panty raid and was not permitted to stay at Harvard. Northwestern was my next college. I had trouble with the dorm situation at Northwestern and moved off campus. I never related to the other students, especially the male students. I maintained a heavy social life, and actually ran a dating service in 1948. At Northwestern I switched majors to economics (theory) and computers. I ended up teaching statistics. I was accepted at the London School of Economics, but did not go.”

Elliott: My liberal arts education at Williams was very important. At the time, I was struggling with “meaning of life” issues. In my sophomore year, I took a lecture course comparing religions. It raised more questions than it answered. And in lecture courses, the number of questions one can ask is limited by class size. So I told my faculty advisor I would leave Williams if I had to take another lecture course. Much to my amazement, he said OK and from then on just seminars.

My “meaning of life” questions were resolved by a moral philosophy course taught by Robert Gaudino, the greatest teacher I ever had (others view Gaudino the same way: when he died, a fund was established to carry on his ideals). In his courses, he required students to read and discuss the texts of the greatest philosophers from Plato on. It was very enlightening. I concluded that Albert Camus was right:

  • There is no evidence to suggest that one set of beliefs is any better than any other;
  • Religion is good for most humans because it provides structure and a moral compass;
  • But no religion or other belief structure can be shown to be superior to any other;
  • Therefore, you alone should decide what is important, and that decision will make it important for you.

After Williams, graduate school in economics was all about learning “techniques”, like learning how to be a plumber or electrician. So despite the bad career advice I got from my economics professors, my Williams liberal arts education gave me the understanding and confidence to do interesting things and enjoy life.

d. The Military

For a number of men, military service was very important. It allowed them to meet other “types” of people and some liked the structure the military offered.

S4, who went on to a career in music and the arts: “Military experience: simply extraordinary and philosophical. I had led a very cloistered life of social and economic privilege. We were not extraordinary wealthy, but we did all the polite things. Two things happened. For the first time I met GIs and sailors and realized they had values and that got rid of a huge amount of snobbism I had. The second thing I realized, after being involved with submarine warfare, was that I could probably do anything I wanted with the rest of my life. That had a profound effect on me.”

C2 on his Army duty: “…a fascinating time. I was a Private at Fort Dix thrown in with everybody. That was an interesting experience, seeing how everybody was treated. It was so inequitable because there were some people there who never should have been drafted. Later, I was posted at Fort Devons as one of the official photographers. My wife and I lived in Groton. And from there I was able to arrange to go sailing so life wasn’t really too tough.”

C4: “”Joining the Navy was a common thing for people to do. An older cousin had gone into the Navy and the family looked upon it as a good thing to do. There was a sense you had a military obligation to fulfill…It was a way to get adventure. I wanted to be a pilot, but couldn’t pass the eye test.

C4 went to Officer Candidate School: “Why waste time as a grunt, if you could be an officer”?

“People change a great deal between ages 20-30: it is when they begin to isolate what they want to do. The Navy offered me the chance to honor one’s draft responsibilities, travel and learn a little more.

C4 re-enlisted in the Navy for a second tour, attracted by the chance to learn foreign languages. He negotiated to be in Naples where he could study languages. If the language studies had not been available, he said, he probably would not have re-enlisted. In Naples, C4 was as an Admiral’s aide. “I polished fire engines for fires that never occurred”.

C6 also benefited from joining the military. When he got to Italy, he put in to be a liaison officer to France (his mother had spent a few years in France and he spoke French). He got to go to Paris for a couple of months. Later, when he got to Germany, the Army was sending people to Sorbonne for education, and he got sent a second time to Paris for the summer. C6: “I was always a terrible student but an avid reader, and those two trips to Paris were very important in molding my interests going forward”.

S3: “Army was a major experience for my generation. I had grown up in such a protected environment. My whole high school life had been in DC and I only had one year at Yale.

The army was an eye opener and clarified some of my thinking. I wanted to somehow break out of the Eastern establishment mold.

S2: “I spent three years in Japan and found the experience much more difficult than Harvard, but they were tremendously enriching years. S2 was first on a mine sweeper and then a communication officer. “I have stated ever since that it was probably the most important 3 years of my life.”

C3 was the only man interviewed who thought his military experience was not fruitful. He found it “stultifying”.

Elliott: “My war was Vietnam. While I was teaching at UMICH, I was draft-exempt. But when went to work at the IMF, I became draft-eligible. I was called to take a physical at Ft. Belvoir. I figured I would be drafted. But I thought the Vietnam was a horrific mistake: we should have recognized Ho Chi Minh as the President of Vietnam. As a result, I had decided to be a conscientious objector. I figured I would go to jail and had already chosen books I would take with me. Miraculously, I failed the physical – I was told my weight was too low for my height. This was of course ridiculous – I was a runner and would have fared far better in the hot Vietnamese jungles than heavier men. The day after I failed the exam, I got a call from an Army office in downtown DC. The officer suggested that I enroll in a physical fitness program they ran. I said “thanks, let me call you”.

Avoiding Risk Versus Taking Chances

There was a real split between those who made life choices based on avoiding risk and those who were looking for something out of the ordinary. For this group of well-established and wealthy men, there was every reason to not to change anything. The following quote from C5 epitomizes how many non-risk takers felt. C5 went to Harvard. When asked if thought of any other college at that time, he said: “None whatsoever, I didn’t give a thought to a single other college. I was singularly unimaginative about the whole process, but that is what distinguished my generation from the later ones. We just followed a routine. We were very staid, very conventional. Most of us wouldn’t think of kicking over the traces and doing something completely unexpected because that would have rippled the water too much in our families.

S1 was perhaps the extreme non-risk taker: he said he went to Harvard Medical School because data showed that once accepted to Medical School, few were tossed out.

Perhaps the two who did best by not taking risks and using family and other connections are C1 and C2. Précis on each follow.


C1 went to St. Mark’s because it was founded by a relative. He followed in his father’s footsteps and went to Yale as an undergraduate. While there, he asked a well-established lawyer in NYC what he should do. The lawyer said “if you want to be a little frog in a big pond come to New York, if you want to be a big frog in a little pond stay in New Haven, and if you want to be a medium sized frog in a medium sized town goes to Boston.” C1 ended up in Boston. After getting a law degree from Harvard, he joined the largest law firm in Boston where his father was a senior partner.


After getting out of the Army, C2 took six months off to go sailing. C2 then started an investment club with a couple of friends. C2: “Initially, we each invested $2,000. It was quite successful so we formed a corporation. We set the minimum size of an account that we managed at $150,000. In five years, they had $36.5 million of our own monies invested and $200 million invested overall.” Today, the company manages more than $700 billion. C2 did not need to take risks. Instead, he took full advantage of his situation.

Consider now those who took risks.

S2 came from a well-established North Shore Boston family. As indicated in his life summary appearing in Part One, almost everything he did was high risk – choosing Japan for his tour of duty, becoming one of the first international radio correspondents, turning down the managing editor’s position of a major East Coast newspaper to start a paper to publish pieces written by non-US correspondents….

M1 and M4 had a lot of early trauma in their lives. Both got thrown out of schools more than once. For them the “avoiding risk” strategy was not an option.

M3 had aspirations of being a great tennis player. He did not care about anything else. When he finally realized this was not to be, it took him some time to resign himself to going to work at his father’s steamship company.

Elliott: My family life was not pleasant and I never felt comfortable in Boston society. I think M4 was right when he said “Yankees are not successful because they kill their own, especially the talented ones”. I would add that for the most part, they are nasty, mean and embittered snobs. I left home to board at Milton at an early age and did not return to Boston until 1985 – a mistake. But when it comes to risk, I bore easily. So I have worked in 46 countries. I don’t worry much about risk: we win some and lose some. I am reminded of Shakespeare’s great words for Macbeth:

“…Out, out, brief candle!

Life’s but a walking shadow, a poor player

That struts and frets his hour upon the stage

And then is heard no more. It is a tale

Told by an idiot, full of sound and fury

Signifying nothing.


Interviewees differed on the time of their most important educational experience: some had it at prep school, a few at college, and a larger number who found their military experience most important. And not surprisingly, most of these wealthy and well-established men were not risk-takers.

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