My dad passed earlier this week at age 90. In the 1950s through the 1980s he ran a small business in New York that started out as a high-end deli on the Upper East Side of Manhattan and ended as a multimillion-dollar party equipment rental business. (The photo is of my mom. There are no photos of Dad in the store -- he wasn't standing still long enough to be photographed.) The business was taken over by my brother and still exists today.

Reflecting on Dad's life as an entrepreneur, I realize his success came down to a few simple lessons, both positive and negative.

1. Never let them see you sweat. No matter what might be going on in your life, your demeanor as an entrepreneur is a performance. If you're in retail, that means you can't let your customers see that you're exhausted, or that you had an argument with your teenage son or your wife, or any other problem. You have to focus on the performance, on the show, and compartmentalize the distrations. (If you work in the catering business or around other sharp objects, this is especially true -- fail to compartmentalize and you might lose a finger in the meat slicer.)
2. Be a man/woman of the people. When you're the boss, whether you have 10 employees or 100,000, you have to show people your humanity. Culture flows from the top. Dad knew where to draw the line between friendship and supervision, (although his manager, Herb, became his closest friend). At closing time, I remember the truck drivers and the counter men coming into the office and Dad pouring them a Scotch in a Dixie cup, after which they'd toast. A little Mad Men perhaps; the idea of drinking at work seems antiquated now. But whether it was the drink, or his willingness to give anyone a pay advance for any reason, no questions asked, no interest charged, he was respected by his staff. That's a prerecquisite for the success of any business.

1. Be curious and act on your curiousity. Every single family vacation we took in the 1960's included stops at local food stores and small supermarkets, because that's where the food giants test-marketed the products they'd be introducing over the next year. At one such detour, Dad found something called Maxim freeze-dried coffee being test marketed. He cleaned out the local grocery of their three or four cases in stock and convinced the manufacturer to send him as much as they'd part with during a test market phase. He displayed it in the store window and sold it for 20 times what he paid. He had a six-month lead on everyone else. Another time the same thing happened with salty snack foods called Bugles and Whistles. Another time it was sourdough bread "imported" from San Francisco, which until he flew it in was unavailable except in San Francisco.
2. Take big risks and be willing to lose. Which is something Dad did not always do. As a depression-era man, he was afraid of credit, credit cards and debt. His landlord offered to sell him the building, on Lexington Avenue at 73rd Street, for $75,000. He declined. Mistake, big mistake. He also never owned a home, and rented apartments his entire life. He also invested once in the stock market, in a company called Square Industries, and lost it all. So he put his money only in guaranteed or low-return investments. Subsequently, he missed the biggest payoffs. I don't fault him for this, but it's worth noting that not all entrepreneurs are big risk takers, and sometimes that's to their detriment.
3. What got you here won't take you there. Dad was in the catering business. One day a regular customer called and asked that he send a dozen folding chairs with her food order. He said, "Of course." Nevermind that he didn't own any folding chairs and no one had ever asked before. He took out the Yellow Pages, found a rental place, and had the chairs sent over. The next day she called and was furious, because the ratty, poorly maintained chairs had nearly ruined her Park Avenue party. So he made another call and bought a few dozen chairs he could rent himself. Then tables, then glassware, then silverware, and more. And then he thought, "Chairs aren't ruined if a delivery truck stops short -- but tea sandwiches are." And so, over a few years, he exited the food business and went 100% into the rental business. I'm oversimplying the cause of the change -- there were other reasons, too: less waste, higher returns, scalability, and the opportunity to work six days a week instead of seven, among others. But giving up what you know in your bones -- in this case, the food business -- and changing the business model completely, is not an easy thing to do.
4. Encourage your children to kick the tires, but don't force it. When I was 12, I started going to the store every Saturday to help out my dad -- a pattern that lasted until I went away to college and when I was between jobs after college. My brother became a lawyer but wasn't happy, so he went into the business. My dad didn't pressure either one of us to get involved, but was accepting of our interest when it happened organically. There is nothing quite like a family business. If you have the opportunity to invite your children to smell the coffee, operate the machinery, or take part in the art of whatever your business is about, you should do it. Whether it takes or not doesn't matter. They'll never forget it.