Category 3. Business


I have had several conversations with a person who manages an enormous amount of money for one of the country’s wealthiest families. Along with his money management role he is involved with the family’s philanthropic efforts.

He would like to know if I would be interested in a management role in an effort that they are putting together through the family’s charitable foundation to address one of our nation’s biggest and most complex social/economic/structural problems. Or perhaps I should have written ‘sets of problems’ since, in fact, the problem they intend to address is a spaghetti of differing issues and interests, winding through many industry segments and demographics.

I like the people behind the effort, respect the resources that they intend to put into it and have genu...

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A Contrarian Bet

In the beautiful valley by the lower reaches of the Connecticut River, the rich are a diminished tribe. Too many are passing away or moving to the sunbelt; their numbers are not being replenished by locally generated wealth or fresh influxes from New York or Boston. More people are leaving the area than are coming – and evidence suggests that this trend is much more pronounced at the top end of the income spectrum than elsewhere.

High-end real estate prices reflect these changes: immaculate, million-dollar-plus homes on stunning properties can now be bought for half their former values. Many cost less than what it would cost to replace the existing buildings, with the land thrown in for free – never a good sign.

Sure, somebody will eventually buy these homes, and one man’s loss is anothe...

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By the time I landed my first professional-track job, I had a great deal of experience with the working world.

When I was 14, I got my first summer job. Despite being the son of a prosperous lawyer, I took an opportunity to work as a janitor in a lower middle class housing complex – I wanted the spending money that a job would give me.

My responsibility was to clean out all of the trash rooms daily. It was a dirty, smelly job, especially on hot days, and it taught me all about how badly some people behave when they think nobody is watching. Some assumed that because I was their janitor, a long-haired kid (hey, it was the early seventies) wearing t-shirts, jeans and sneakers that were often pretty dirty, I was far beneath them socially; I was somebody to whom they could behave thoughtless...

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A Paean to Risk

A former colleague of mine once said something wonderful:

“If you are not making any mistakes, it’s because you’re not making any decisions.”

When I consider the single characteristic that is most vital to the success of an individual, an organization or a society, I conclude that it is a willingness to innovate. Whenever we try to freeze time, and lock in the benefits of now, we consign ourselves to a future failure that will be far more painful for our efforts to avoid the change that is inevitable.

What is this innovation, then, that is so important at every level of society? It is, quite simply, the product of risks that have been taken. Note that I do not assert that it is the result of risks taken successfully, because it is also the end product of all the risks that were ta...

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