Published in the San Diego Union-Tribune, October 21, 2019
“What is the biggest mistake you have made?”
Hundreds of chief executives have been asked this question, and one answer consistently rises to the top above all the rest: I waited too long. I waited too long to hire, to fire, to merge, to pivot, to declare bankruptcy, to raise money, to step down — and so it goes. There are countless “waiting too long” stories. Here are a few.
• “My biggest mistake, probably of my whole career, was not closing down our mortgage broker business sooner.” — Jamie Dimon, JP Morgan Chase.
• “My biggest mistake by far was not moving faster.” — Jack Welch, GE.
• “I find it very difficult to think of mistakes … but Virgin soda, that was a big one.”— Richard Branson, Virgin Group.
• “I didn’t fight the board hard enough to stop it (expansion of Gap stores).” — Mickey Drexler, J.Crew.
• “I wish I had started having children younger.” — Carol Bartz, Yahoo.
• “I should have bought Fannie Mae sooner; we would have made $1.5 billion.” — Warren Buffet, Berkshire.
• “Hiring Bob Eaton from General Motors, biggest mistake of my business career.” — Lee Iacocca, Chrysler.
• “I shouldn’t have brought Time Warner into the cable consortium, but I was tired and when you’re tired you don’t make the best decisions.” — Ted Turner, TBS and CNN.
• “I should have bought Square.” — Marc Andreessen, Netscape.
• “I personally think patents are for the most part worthless, but if I had done it at Broadcast.com it would have been a ton of money.” — Mark Cuban.
• “I phased out DVDs too soon, lost lots of customers.”— Reed Hastings, Netflix.
• “Hiring mistakes. I have put too much weight on talent and not enough on personality.” — Elon Musk, Tesla.
There are a hundred more, but you get the idea. The CEO comments above reinforce the idea of how hard it is to not only make decisions, but also to know when to make them.
So the puzzler is, when do you know you’ve waited too long? I think this a tough one. For example, you are going along and business is good and decisions are percolating and it is not too late yet, and then some more time passes and it is still not too late. And then, all of a sudden, in an instant you look up and you realize you have waited too long, missed the moment.
The image I like to use is Mount Everest. The actual top is a knife edge. If you miss a step, well like in the side-view mirror, objects (and decisions) are closer than they appear. And talk about waiting too long — when is it time to start down? If you get that one wrong, the ballgame could be over very shortly.
Let’s think about deals that turn bad. They do not start out bad. Each one starts out with good intentions and a firm belief in doing the right thing. Then something happens and there is a moment where you need to make the key decision, the one that will inform the next period of your life. Do you cook the books, do you rob Peter to pay Paul, do you keep your pal as VP of whatever, even though he is incompetent, do you wait too long to raise money etc.? Hoping is not a business strategy and waiting too long — well, the risk is that next step can’t be redeemed and the slide down the other side of Everest begins.
This stuff fascinates me. Knowing that instant when you still have time and then the sudden realization it’s too late and you cannot turn back, I’m not sure that can be easily explained or taught. Maybe it is like Justice Potter Stewart’s definition of hard-core pornography, “I’ll know it when I see it.”
This last couple of weeks has been the High Holy Days for the Jews, and one of the themes is regret, confession and then redemption. Our deal with God is you get a new set of cards each year, you get 52 new ones to play as well as you can, but in our secular life, that is not the case. You have to live with your decisions — the ones made and the ones not made. And you can’t wait too long.
Senturia, a serial entrepreneur who invests in early-stage technology companies, writes weekly about entrepreneurship in San Diego. Email ideas to [email protected]
Rule No. 632
Jokers are in every deck.