The year is 1972. It’s early afternoon at SlantFin, a company that manufactures baseboard heating. Two men are standing in the room. One is Barry Minkin, head of personnel. The other is the executive vice president, who as it happens, was my grandfather. The rest of the story has become something of family lore, but it goes something like this:

A salesperson comes into my grandpa’s office, bursting with excitement. “Mr. Goldman, Mr. Goldman! We got the order!”

“That’s great!” says my grandfather. “Let’s see the paperwork.” At that, the salesperson pauses. He shifts a little uncomfortably.

“Well, Mr. Goldman,” he begins. “The thing is, it’s 99 percent sure…”

My grandfather, in what I can only assume was a very kind way — for he was always a kind man — looks at the salesperson. “Well, we have law around here.”

“We’re going to call it… “At that, my grandfather looks around the room, and always with a knack of illustrating a point, he spots Barry. He continues. “Minkin’s Law.” He pauses for effect, as both the salesperson and Barry wonder what he’s up to. “And do you know what that law is?”

“Ninety-nine percent sure is as good as lost.”

Practicing Prudence and Patience

I believe what my grandfather was trying to impart to the young salesman was a sense of prudence and patience, which is a skill that takes time to build up in business.

It’s easy to get ahead of ourselves. When something good happens we want to shout it out, but think about the fallout when we’re incorrect. We risk losing credibility. This is particularly important when are you first starting out. Ernest Brod, Managing Director of Alvarez & Marsal Global Forensic and Dispute Services, knew my grandfather when the “law” originated.

“Earlier in my career I was a co-founder of a startup company marketing telecommunications systems to hotels and motels,” Brod said when I spoke with him. “We were tremendously successful selling, but it turned out our product didn’t work. We tried to salvage the venture by pivoting into a broad array of technology systems for the hotel of the future. We found an investor, but the day before the closing he said there would be a slight delay, but he was 90 percent sure it would still go through. A friend who was in the M&A business told me that once a deal is delayed, the odds are strongly against it ever happening. He was of course correct. Later, when colleagues in the investigations business would tell me a great new case wasn’t in yet, but that it was right on the doorstep, I would use the quote frequently.”

My grandfather often quoted Voltaire: “Don’t let the perfect be the enemy of the good.” You need to maintain a sense of optimism that you can make extraordinary things happen. The nuance is in finding out how to get the deal closed and knowing that you can figure how to make it even better later on. This optimism is key to keeping sanity in business, but it needs to be tempered with experience. As Brod put it to me: “Blind optimism is destructive. You can’t sit back and say it’s almost certainly going to happen. You have to keep doing what will make it more likely to happen.”

When I was running my startup, I often found myself learning the hard way. I would be so sure something good was right around the corner and wind up being so disappointed. There is no better example than in trying to raise funding. Venture capitalists will almost never say no. I had to learn how to filter out the “noise” from what is actually possible.

Pay close attention to how quickly someone responds to you. If they are genuinely interested in doing a deal, they will usually respond fairly quickly. I found very good luck with using a mail tracking tool like Yesware to see how quickly people were opening my emails. This usually gives you a good indication of interest and an important bit of insight into how hard you should push and where you should focus your attention. If the person you are trying to do business with keeps delaying or finding excuses not to respond, chances are they just aren’t that interested. Apply the same rules you would in dating. Cut your losses and move on.

And that’s what separates the winners from the might-have-beens. To be smart in business, we must have enough optimism and faith to go for things that seem impossible, but enough discipline to keep driving the ball forward until it goes over the line. That requires us to make smart decisions about where we put our efforts.

And do you know what? I never did think to ask my grandfather if the salesperson ever closed that deal.