It’s tough to outdo the ancients: entrepreneurs in the classic sense. Alexander the Great and Julius Caesar – the names that we all recognize and that are part of our culture – and even the less familiar ones, the likes of Sulla, Crassus, and Pompey, were all equally well versed in matters of strategy, tactics, execution, and leadership. Most of all, these gentlemen understood venture capital. We moderns tend sometimes to give ourselves great airs, we take pride in our modernity and sophistication. We act as though we invented risk and return, portfolio diversification. We act as though we invented investment and payback, when thousands of years before us, the Roman generals were negotiating private deals in order to finance their armies, in order to secure positions of potential profit to themselves and their backers, based on preferential return structures not unlike present-time venture finance, with all but the 3x liquidation preference in place. And more: these ancient CEOs even had something like a board of directors to report to, off and on: the Roman senate.
It would be nice if our business schools would encourage familiarity with such classics as Plutarch’s Lives, which profile these entrepreneurs in surprisingly modern nuance. It would have been nice if, back in the day, I would have been assigned The Discourses on Livy, not as a substitute for current business or entrepreneurial texts, but as a complement. In its discussion of the founding and expansion of Rome, this book can easily be read as an entrepreneur’s “how to” guide, just as The Prince, in its treatment of the conquest, takeover, defense, and operation of expanding principalities, can be read as a book about M&A.
In some ways, a lighter and more flashy equivalent of historical battle lessons, and a field that provides an ongoing commentary about leadership, management, and even finance, is that of professional sports. Having for a long time now made it my hobby to study the local [cough] NBA franchise, in all its [cough] glory, close calls and near misses, trades and roster management, coaching changes, playing style adjustments, and payroll (salary cap) issues, I feel like an education in strategy has been there for the grasping all along. And here also, issues of risk, return, diversification, forecasts, are not as far removed from venture investing and business planning as may be supposed. Nor are the issues far removed from the ancients.
I don’t, of course, mean to compare the Roman Empire to the Chicago Bulls dynasty, or either of these to Twitter. I would like only to suggest that important business teaching is all around us and sometimes in surprising places. Many such lessons have, moreover, withstood the test of time for much longer than, say, The Black Swan or Modigliani/Miller finance theories. (On the other hand, if the current trend continues, the likes of Steve Jobs and Jeff Bezos are projected in a thousand years to be studied as though lords from a magical time and place, so we may as well start brushing up.)
