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Creating an Image of Success

So, you want to tap into the affluent market? You’ve got to invest in yourself first.By Howard B. Cowan, CLU, ChFC

By Howard B. Cowan, CLU, ChFC

Think of two young associates—we’ll call them Bob and Jim. Each wants to work with affluent clients. When Bob goes off to meet prospects, he drives a Honda, while Jim drives a Mercedes. Bob wears a suit from Sears, Jim wears one from Barneys. Bob wears a Swatch, Jim a Rolex. Now, based on this snapshot, ask yourself: Which of these two associates do you think an affluent prospect will be more inclined to do business with?

Certainly a good deal of success goes back to the basics, like prospecting and keeping your word—that’s a given. But there’s another ingredient, equally important: creating an image of success. The truth is people are more likely to trust you with their money if they think you are already successful. And appearing successful entails two things: living large and getting out there. Let’s explore both.

Living large
As the founder of a financial services firm in New York City, I often hold workshops for my associates and offer them this advice: Live large to attract the kind of people you want to do business with. Wear well-tailored suits. Drive impressive cars. Live in upper-middle class neighborhoods. Granted, this advice may sound like an unnecessary risk, especially when you’re just starting out. But early on in my career, I learned an important lesson: You have to spend money to make money. And one of the first things I ever did was borrow as much money as I could to invest in my image. Here are a few suggestions on how you can invest wisely:

  • Lease a car. So, let’s say your budget is tight, and you can’t afford a Mercedes or other high-end car. Then lease one. When one of my colleagues pulled up at a prospect’s home in a Mercedes, the prospect turned to his wife and said, “He drives a better car than we do.” The prospect was clearly impressed with the associate’s apparent success, and soon did $50,000 worth of business with him.
  • Live in an upper-middle class neighborhood. One of my associates took out a loan and rented an apartment on the Upper East Side of Manhattan, a trendy part of town filled with boutiques. Inside his apartment, he had one piece of furniture, but that hardly mattered. He had an address that would send prospects a message of success. When you strike up a conversation with a prospect, after all, he may well ask you, “So, where do you live?”

Getting out there
The other step toward creating an image of success is getting out there; you increase the likelihood that you’ll be in the right place at the right time. Again, here are a few suggestions:

  • Get involved in high-profile organizations, clubs or groups outside our industry. This can include sitting on the board of a local United Way chapter or serving as president of your college alumni association. One associate I know hosts a dinner at his house each year to benefit the American Diabetes Association. His involvement benefits the association, and helps him make contacts.
  • Vacation at the best resorts. This means places like Vales in South Wales and Nevis Island in the Caribbean. And when you do, check into a hotel like the Four Seasons, the Ritz-Carlton or the Mandarin. You’ll invariably strike up a conversation with fellow vacationers. As soon as the talk leads into “So, what do you do?” you’ve got your in. Also, in your hometown, join the local country club, sports or yacht club.

In the end, you probably know better than most that reaching the top of this industry is not easy. It takes prospecting, cold calls, training and long hours. Still, my guess is you do all these things because you understand that’s just what it takes to succeed. Think of investing in yourself the same way, and make it a normal course of doing business.

Believe me, by investing in yourself you’ll be doing what many other associates—like our friend Bob—write off as too risky. And by taking that leap, that image of success will become a reality.

Howard B. Cowan, CLU, ChFC, founder and president of Cowan Financial Group, has received MassMutual’s National Chairman’s Trophy a record 18 times for managing the No. 1 agency in the company based on production. He can be reached at 212-536-6100 or at

Cowan is a registered representative and offers securities, investment advisory and financial planning services through MML Investors Services, Inc., member SIPC, 530 Fifth Avenue, 14th Floor, New York, NY 10036, 212-536-6000. Insurance offered through Massachussetts Mutual Life Insurance Company and other fine companies.

The views expressed here are of Howard B. Cowan. Howard Cowan's views are not necessarily those of Massachussetts Mutual Life Insurance Company or its subsidiaries.



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