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Lessons in Cruising Wealthy Circles

“The first step in getting to where you want to be is acting as if you are already there.” This age-old advice holds a valuable lesson for successful agents and advisors.

You are successful. You’ve built your business. Your economic situation has improved dramatically. Although you live in a great house, drive a luxury car and drop your children off at private school, you feel you are in a rut. Ten years later, you are socializing with the same people. Everyone knows you sell insurance. How do you attract wealthy friends? Live the “Lifestyles of the Rich and Famous”?

It’s Not About Business

You aren’t looking for another prospecting channel. You have a different objective: to mix and mingle with the seriously wealthy, make friends and develop social relationships. If business comes, it has its own timetable. You want access.

The Luxury Cruise Vacation

Years ago, I learned about a financial advisor who built his business by taking exotic vacations priced to attract wealthy travelers. He made great friends, some of whom became clients. Focusing on the friend part first, consider taking a cruise.

Once considered the preserve of “the newlywed and nearly dead,” cruising is now hot.  In 2012, the Daily Telegraph reported 20.6 million holidaymakers chose cruising, up 10 percent from the previous year. Cruising lets you rub elbows with the wealthy and successful, but choose your cruise wisely.

Lesson One: Pick the line most likely to attract the crowd you want to meet.

Cruise lines have personalities aligned to target audiences. Carnival brings to mind cheap fares, young people and partying. Cunard reminds you of transatlantic elegance and formality. Seabourn is small ship luxury. Please note:  All three brands are owned by Carnival Corp.

Lesson Two: Certain routes attract a different clientele who can afford to be away for longer periods

Different routes attract different clientele. In most cases, the longer the trip, the better.  Those short “cruises to nowhere” attract more of a partying crowd. Point-to-point trips attract a better heeled crowd because airfare is an additional cost. The same rule applies to voyages departing from foreign ports.

Lesson Three: Look well-groomed and successful.

Let’s assume you book a cabin, board the ship and start relaxing. You’re having fun meeting lots of people. Even though you’re on vacation, you must always dress well in clothing appropriate to your body style and age. Elderly European men might wear Speedos by the pool, but it’s not a pretty sight.

Lesson FOUR: Focus on meeting people by engaging in thoughtful group activities.

You aren’t dating, but you want to meet people. Skip hanging out at a bar and asking, “Come here often?” Seek out activities that attract thinking people, such as lectures and shipboard quizzes. Visit the dining room for breakfast and lunch during open seating. Request to be seated at a large table. If the ship has special lounges for passengers traveling in higher grade cabins, visit the ones you can.

Lesson Five: Give to get. Entertain to get to know people better.

Start entertaining. Ships can provide many services few people know about. Host a cocktail party in your cabin before a formal night. The ship can supply flowers and appetizers. Cabin too small?  Ask about renting or reserving one of the smaller lounges for your exclusive use. Can they provide music? The ship should be able to provide invitations and hand delivery.

Lesson Six: Let them talk. “The person talking is the one having a good time.”

Listen. The people you will meet are well traveled and like to talk. The wealthy have a travel language all their own. Sharing some of your own stories or confirming details gets you into the game. Where are they going next? If you’ve never been there, express interest. How did they choose that destination? Have they been there before? If you have visited there previously, share details and recommendations.

Lesson Seven: Treat the staff well. They will respond by showing you the respect normally given to the very wealthy. People will notice.

Be nice to the staff. Learn the names of people you see often. Greet them by name. Smile. Remember to tip. In the Old World, one of the signs of good breeding was the respect the wealthy showed to their staff. They will like you if you treat them as peers instead of servants. There are many little things they can do to make your vacation enjoyable.

Lesson Eight: Establish an enduring bond that will last beyond the vacation.

Identify interests in common. The people you will meet are wine/travel/cooking/golf fans. If possible, enjoy these pursuits on your vacation. Enthusiasts enjoy sharing their passion with fellow fans regardless of economic status. 

Lesson Nine: Make promises to do things. Commit yourself.

Plan to see your new friends again or keep in touch. You have a great book on a city they plan to visit or a map to pass along. You have a great wine they might like. Take photos of everyone having a good time. Get contact information.

Lesson Ten: Make the first move. Deliver on your promises. Establish a new friendship.

Reach out afterwards. Print and send those photos. Opening an envelope and handling pictures brings back memories that viewing a computer image doesn’t. Send that book or the article clippings you promised. Call and stay in touch using common interests to get the ball rolling. If they live nearby, plan on getting together. If not, will they be passing through your area or vice versa?

In The Background

Do the wealthy make new friends? Yes. Are they on guard because people want something? Yes. It’s likely they have checked you out. One person we met (retired law enforcement officer) would learn where you lived and quietly check out a satellite photo of your home on Zillow! Google or LinkedIn is the more likely approach they will use early in the trip. They know what you do. You haven’t pushed business or set off alarm bells by asking too many questions. You let them do the talking. If you select an environment populated by wealthy people and you make friends, it’s logical that those new friends also will be wealthy.


is president of Perceptive Business Solutions in New Hope, PA. His book "Captivating the Wealthy Investor" is available on He can be reached at [email protected].

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