I've won some and I've lost some. Along with some partners, I started ADWEEK in 1979, at the beginning of the long expansion of the 80s. Were we smart or were we lucky? A little of the former, a lot of the latter, I think. I'm absolutely certain, had we been in the economy of the past 3 years then, with our limited financial resources we would have failed (and there'd be no ADWEEK Magazines today). We managed to sell in 1990 at the top of the advertising economy expansion, just before the first Gulf War crash. I was also one of the early investors in AdTech and managed to sell out a time when the internet expansion still seemed like it would go on forever.
I've had many losses along the way as well. I've bet at the commercial real estate table and lost big by having to sell out in down markets buildings that proved to be big winners later in up markets. I invested heavily in internet stocks and startups in 1999 and 2000 with the now well-known (and widely-shared) disastrous results. Even worse, I invested in those days in startups that were both internet and advertising based just before the precipitous fall of both industries. I've probably started more magazines than anyone else still active in the industry today. Only a few survive.
It all started early for me. While going to grad school in Miami in the 60s, I had an actual "system" for real-life gambling. I worked out a way to predict the likely winners at Jai-Alai. I bet hundreds each evening, way beyond my means, by borrowing money from classmates and promising big guaranteed returns. By virtue of luck, not any system, I was running way ahead while living the high life on Miami Beach. But then luck turned, I lost it all and had to borrow money from parents to get out of town and back to the North to go to work.
So, with all these credentials for winning and losing at games and the game of business, what have I learned? Business is not much different from one of the casino games. You put up your money, you play your system and you hope for the best. Sure, you think you can rig the outcome by virtue of your smarts and having good people at your side. But, timing is everything. And timing is mostly luck. A good idea executed by good people in a crummy economy will fail as easily as a bad idea in any economy.
Unlike Bill Bennett, I haven't given up my kind of gambling as yet. I'm having too much fun. And, until it's all over and you can total up the score, it can actually seem like you are doing something worthwhile.