How sad that Bruce Wasserstein died just as it appears that the M&A market is heating up again. I got to know Bruce when I was editing Harvard Business Review; with one of my colleagues, Gardiner Morse, I produced one of HBR’s trademark in-depth interviews, published in January 2008. 

Bruce was a curious guy, in both meanings of the word. His extraordinary mind was able to see deals through multiple dimensions simultaneously - he compared deals to prisms that should be turned and examined from every angle.  The very complexity of his insight left him almost inarticulate sometimes; unable to express everything he saw, he would speak in what sounded like koans or riddles.

He was the ultimate power-player among investment bankers; but he was usually alone on his walk across Rockefeller Plaza to the 21 Club for lunch, not surrounded by aides and acolytes. He was a fierce and aggressive capitalist - but also a long time supporter of Ralph Nader’s work and co-author of a “Nader’s Raiders” report, The Closed Enterprise System, calling for more aggressive enforcement of antitrust laws.  He was 24;  I, 23, edited it.

Above all, though, he was a man you’d want on your side in a deal, whether you were buying or selling. And because he’s not here to offer his advice - and because many smaller companies couldn’t have afforded him if he were - here are a few things he said that stand out in my memory, and that entrepreneurs might value.

*  Examine the premises of a deal. Ptolemic astronomy is proof of the fact that you can construct a perfectly coherent, consistent, logical belief system on the basis of a false premise. Business history is littered with similar faulty-premise mistakes. I write as an alumnus of Time-Warner. 

*  In the heat of deal-making, broad questions get too little attention. Macroeconomic shifts obviously affect the value of a company, no matter how great it is; but the link between macro cause and micro effect might not be obvious. Wasserstein talked about advising a CEO who wanted to buy a doorknob manufacturer: “It didn’t occur to him that many knobs are bought as replacements. Well, if people can’t get mortgages, they can’t do home improvements, and that affects the knob business.” Or think about changes wrought by globalization. You’d figure that nobody in his right mind wants to be in the automobile industry; but if you take off your OECD blinkers and look globally, you might discover, as my Booz colleagues argue, that “The Best Years of the Auto Industry Are Still to Come.”

*  Every deal has more risk factors than you think. Strategic risk is not the same as operating model risk is not the same as financing risk is not the same as people risk - all of which  have both quantitative and qualitative dimensions.

*  No one deal fits all. The value of an asset - and if you’d like to be bought, you are now an asset-in-waiting - varies enormously depending on whose portfolio holds it. Take, for example, New York magazine. Bruce bought it in 2003 for $55 million. I’ve no idea whether the magazine will be put up for sale now. But if it were, one could imagine bidders from big media companies; from small companies that collect niche magazines;  from the New York city real estate industry (one of whose tycoons recently acquired the weekly New York Observer); or from any number of other businesses. For each, New York would serve a different purpose; each might have a different monetary value; and each would certainly trigger a different set of calculations and judgments  about strategic, operating model, financing, and people risk - all of which you as a seller should think through. As Bruce said in the HBR interview, “When we’re presenting on a client’s behalf to potential buyers, we tailor our presentations to suit each prospect. One may want to focus on cost synergies, another on opportunities in China.”