by Kim Hackett

Photography by Alex Stafford

TOM SHEPARD INHABITED THE REAL WORLD of Mad Men, the TV show about the glamorous 1960s-era Madison Avenue men and women who created modern advertising. Shepard, now 96 and living part time on Longboat Key, once traveled the country selling Vick’s VapoRub to druggists and convinced farmers to let him put Vick’s signs on their barns before outdoor advertising became common.

Later, Shepard worked with such iconic American brands as Zippo Lighter, Coca Cola, Sunkist and General Electric, convincing them to advertise in Look magazine.

Shepard ascended to publisher and reigned during Look’s most influential years until it folded in 1971 as advertisers flocked to TV. He then became president of the Institute of Outdoor Advertising as it evolved from barn signage to sophisticated billboard campaigns. Shepard recently published his fourth book, Making the Sale, the Art of Salesmanship.

“I’ve been selling for over 70 years; I’ve sold hundreds of millions of dollars in products, and what I tried to do in this book is help the reader understand the cardinal principles of selling.”

“As a salesman for Look in the 1940s, I followed two rules and I follow them to this day: Never be too busy to say hello; and No. 2, if you’re talking, you’re not learning.”

“We’ve lost the art of conversation and it’s hurting our country. People are doing the ‘how are you?’ bit and walking right by you.”

“Since I started in business as a traveling salesman for the Vick Chemical Company, technology has transformed communication. Yet the most fundamental element in the art of good salesmanship is still the human aspect. A salesperson who takes the time to focus on the customer’s needs and preferences and who presents an agreeable personality—the one who says hello and listens carefully—is still the salesperson who finishes on top.”

“When Look folded, it taught us a lesson in the magazine business. After TV emerged, we were in a circulation race to get numbers; consequently, we lowered the price of our product in order to attract more circulation in order to compete with TV. We charged in the last days only 75 cents a copy for Look. It cost $3 to produce it.”

“When you go looking for a job, the tendency has been to present a resume and talk about yourself. They’re not interested that you were president of the debating club or a hockey player; they’re interested in what you can do for them.”

“Nothing happens in American business until something is sold. Proctor & Gamble, the biggest package goods company in the world, would go out of business if it didn’t sell a product.”

“If you have something important to say, say it importantly, because if you don’t, people may not think it’s a significant product, service or announcement.”

“Know your product inside and out; know your customer’s needs inside and out. Read the chairman of the board’s annual letter because he will tell you what his dream is for the company.”

“Approach top management. When I started at Look, we were getting bits and pieces of Sunkist Oranges, a huge operation on the West Coast, while other companies were winning major contracts from them. And I noticed that we weren’t getting any Del Monte food advertising. After looking over those two accounts, it struck me that one of the reasons we weren’t getting those accounts was that we didn’t have contacts with senior management. So part of my strategy for our salesmen was to see that they had the guts and know-how to approach top management.”

“Creativity has to be within, but if you can develop a curiosity about life, about people, it’s powerful. Be wide in your interests. That leads to inspiration.”

“The producers of Mad Men had fun with that period and they got it right. Underneath, those were the wonder days of magazines and newspapers; TV had yet to emerge, or it was just starting to, so we had the world to ourselves.”