Category 3. Business

19. Two Men, A Difference and A Strategy

“My faith! For more than forty years I have been speaking prose while knowing nothing of it, and I am the most obliged person in the world to you for telling me so”. Molière, Le Bourgeois Gentilhomme

For many years, it was my job to tell the CEO that he was speaking prose.


Some people are born to be entrepreneurs. Put them in any environment and, operating mostly on instinct, they will find ways to make money. The CEO was such a man.

His first job was evidence for this proposition – he got himself hired to park cars for a minimal salary and – more important – big tips at a beach club in Long Island. Nothing so special about that, you may think, but wait: he was 15 at the time. No license, not even a learner’s permit...

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18. Very Personal Relationships

It would be hard to overstate how close we were in those years. For a couple of guys who seemed to have little in common, the CEO and I had established an extraordinary level of personal trust.

When, in early 1996, the head of one of the larger companies that was gobbling up smaller competitors in the CEO’s industry offered him $120 million for his business, numbers unseen, I talked him out of taking the offer seriously. I told him that his company was worth at least $150 million and was still growing fast. Why would he want to sell it and pay huge taxes? What would he do then that would be more fun than what he was doing now? A strange line for a success-fee-earning banker to take, to be sure, but I believed every word I said...

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17. An Unforgettable Scene

Imagine hosting a fancy party at which you’re surrounded by sixty of your nearest and dearest. Almost all of your guests assume that the reason for your having such a grand gathering is simple – a joint decadal birthday celebration for you and your wife – but that supposition is wrong. Only four know that for many who are present, the economic facts of their lives are about to change in unpredictable ways; the party marks the end of one era and the beginning of another.

If the unwitting guests knew of the changes that are in motion, which they won’t learn about for a few more days, they would be speaking of little else, trying to sort out what it all meant for them or making sure that they talk with people who would suddenly be more – or less – important to their lives...

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16. You Can’t Lose ‘Em All

Almost two decades ago, we had another experience of doing business directly with the government; this one was very different from the experience described in Accused, but no less revealing in its own ways.

A part of the government that controls tens, or maybe hundreds, of billions of dollars worth of assets throughout the country decided to try to impress Congress by using some of those assets to earn a little money in a manner with which our company was broadly familiar. They put out a request for proposals that was breathtaking in its scope; it wasn’t clear whether what they had in mind was a $100,000 program or something a thousand times bigger. 

The CEO was skeptical from the start but I was intrigued...

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15. Accused

On one otherwise placid morning in the middle of the good years – the ones in which the company that we were building was growing like wildfire – a prominent official went on television to accuse us of having defrauded the government. The CEO and I sat watching the official’s performance; we were seated in one of our conference rooms with a couple of dead silent colleagues, all of us in shock.

Unless you’re new to adulthood, you know something about the man who was accusing us. You have read about him in the newspapers; you probably followed his campaigns with at least mild interest. He was a somebody. He was running for higher office at that time and, as the CEO remarked, wearing his best suit for this particular television interview.

This morning, he was explaining that our company –...

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14. A Fuller Picture

I can’t continue to write these little stories from my career in complete isolation from what was happening in other parts of my life when the events I’m describing took place. We are not uni-dimensional; pictures that present us as such are false.

For example, over the course of our married life, the Beloved Spouse has often commented that during those periods during which I wasn’t exercising on a regular basis, I was much more difficult to live with. She has even put the matter more strongly than that, hard though that may be to believe.

Two things figure into the facts behind her assessment...

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13. Worlds I Left Behind

I was on top of the world.

The Beloved Spouse and I were vacationing in San Francisco with our first child – a beautiful baby girl. I had just finished a four-year program of getting a law degree at night while working at the bank full time. My job had been going exceptionally well – so much so that I had just been promoted in title and given a grand new opportunity – I was to be one of the leaders of our institution’s move into investment banking. A huge honor for a guy who was only twenty-eight.

We were staying in a fabulous apartment (today it would probably go for ten or fifteen million) owned by a friend of the older of my two brothers...

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12. Six Dark Years

I had six dark years. Six years during which my professional prospects and my earning power were diminishing relative to my personal responsibilities. That’s a long time.

(This will be an overview post – the only one in this series; I think it’s more interesting for you and more challenging for me to try to put you into individual scenes in which tough decisions were made, but this post seems necessary as a connect-the-dots bridge between some of the older vignettes and the more recent ones).

Beginning in 1987, facts began to emerge about the deal described in Troubles that cast a long shadow over my career at the bank. A deal that had briefly enhanced my reputation as a leader instead came to make me look stupid or worse...

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11. Never is Almost Forever

In the first flush of my apparent triumph in the deal described in yesterday’s post – Troubles – I embarked on another deal opportunity. This one would also change my life profoundly in ways that would only become clear over the course of many years. The deal described in Troubles would ruin my career at the bank; this new one – a seeming failure at the time – would ultimately make me a wealthy man.

In this new opportunity, I got to know the man with whom I would probably spend as much daylight time over the following thirty years as I would with the Beloved Spouse. Maybe more.

I had already met him briefly at an industry gathering – a big, brash Jewish entrepreneur who spoke in outer-borough cadences. He was roughly ten years older than I was, so in his late thirties at the time...

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10. Troubles

I didn’t always do the right thing.

This post will be an effort on my part to capture in fewer than 1,500 words an experience that took me 150 pages of self-reflection to sort out back in 1991, after I had left the bank. I needed to understand how I had screwed up a career I loved.


In the mid-1980s, the big commercial banks were beginning to work their ways back into the investment banking world; Glass-Steagall, the Depression-era law that had split commercial and investment banking, was going away. My employer was one of the banks trying to learn new dance moves. I was one of the bright young things sent out onto the dance floor.

I was five or six years into a management-track job that senior management still thought of as a presumptively permanent, almost familial relationship...

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