Jack Connors, on Pitching CEOs, Making Friends and Acting Like a Trapper

A Candid Chat With the Advertising Hall of Famer

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Rance Crain
Rance Crain

Willie Sutton robbed banks because that 's where the money was. Jack Connors pitched CEOs because that 's where the decisions were made -- and CEOs lasted longer than CMOs and ad directors.

That, in a nutshell, is Jack 's business strategy, and it helped him build Hill Holliday Connors Cosmopulos into the most successful agency in Boston and all of New England. Jack was inducted into the Advertising Hall of Fame this year, and I took the occasion to chat with him about his career.

If he weren't such a consummate ad-agency guy, Jack would have made a great Boston pol. He's funny, candid, self-deprecating -- just the right combination to roll up the votes. He told me he'd thought about throwing his hat in the ring over the years, "but I think that we ought to leave politics to the pros, and I like the money in the private sector, to be honest with you," he laughed.

Jack admits he offended his share of ad directors. "But I think the proof is in the pudding. We have a very impressive record at Hill Holliday of retaining clients, and I think it's because we built those relationships with the top people, and it wasn't just to do their advertising. That was obvious. But it was really to enhance their reputation. To make the CEO stock more important. . . . If you could make the CEO look better, then you can go and ask him for a raise once in a while. And you can improve the margins."

Jack Connors (right)

In the early days of his agency, Jack said "the only people who would hire us were the people who didn't know better." One of his agency's techniques was to handle charity work for free, "and we really didn't care, to be painfully honest with you, what they intended to cure. We wanted to know who was on their board. . . . Because the chairman of the bank, the chairman of the insurance company, the chairman of the mutual fund of those organizations were on the board. And after a couple of years of doing free work for them, they'd go back and say, "We're getting great work from this Hill Holliday. Why can't we have some of that here at the company?'" The agency worked for Liberty Mutual, Bank of America and a number of mutual funds over the years. "So it worked," Jack told me.

In the very early days of his career, when he was working at BBDO as a account guy on the regional Dodge business, he was doing such a good job that he was summoned to Detroit. They told him he was being promoted to VP and moving to Detroit. He quit the next day.

In 1998 Interpublic bought Hill Holliday and Interpublic CEO Phil Geier tried to get Jack to come to New York. He turned him down, just as he turned BBDO down. "I'm an entrepreneur. I'm not sure I can spell it, but that 's what I am. And I love Boston. I wanted to be home. And I had the opportunity to build a big business in my hometown. . . . So I monitored all those public companies, and I wanted to sell to Interpublic, but I never wanted to run Interpublic. That would be too much like herding cats."

Jack said ad agencies are different from when he was building his business because they have more layers today. "So the friendships and the relationships and the closeness that once was is a little more challenging." He added that people think they're at an agency to service a particular account "as opposed to really building the company."

That isn't a function of size but of attitude. "You know, it's like anything else. There are trappers and there are skinners. To be a trapper you've got to put on snow shoes, you've got to go out in the cold, you've got to set those traps, and then you've got to go back and see if there's any animals in them. And it's cold out there."

Most people sign up to be skinners, Jack said, because you can stay warm and you don't have to be tramping about. But he characterized himself as an "old fashioned trapper. I love the hunt. And I think it's been said on occasion that my interest peaks once we sign a contract. I don't think that 's quite fair, but there's a little bit of truth to it."

His agency's ability to handle rejection was one of its keys to success, Jack said. He likes to say that even Boston Red Sox great Ted Williams, who set the batting average record of .406 in 1941, failed six out of 10 times.

"And so the dirty little secret of my career is that with all the great agencies I competed with . . . no one ever kept score of all the losses I had, the pitches I made and lost, or made a fool of myself, or wound up in third place or tenth place. . . . So I'm thinking it's about getting up to bat."

Of his three partners, Jack was the last to leave. "I was the survivor, if you will. Alan Holliday left after six months. Steve Cosmopulos left in 1978 after 10 years, and my partner Jay Hill died, after we worked together for 28 years, of cancer.

"So, I began thinking, "I'm next.' There were three gone and I was the survivor. And then when I'd go into meetings with clients or prospects, everyone was 30 years old, and I wasn't 30 anymore. And there was a nice respect and I built some friendships. But when you build relationships you build them with people your own age, from your own generation. So it was time to exit stage left."

What's he proudest of ? "Well, I think maybe two things. One, that we've endured. Now that Hill Holliday is 43 years old I would say endurance is significant.

"The second thing I guess I'd be most proud of is that we really made a difference." The people at Hill Holliday honored the company values, which were based on the line from the scripture, "From those to whom much has been given, much is required."

Jack believes that "we're the ones that made the money. We're the ones that had success. Now we've got to help those that weren't as fortunate as we were."

For the past five summers Jack has been operating a day camp for disadvantaged kids 11 to 14 years old called Harborview.

"That's what they do with public-service work, and that 's what I do with my life."

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