Say what? Advisers share clients’ craziest stories

  • August 31 2016, 3:48pm EDT
Like psychologists, bartenders and hairdressers, financial planners sometimes hear some interesting tales. We asked planners for a peek into their most surprising client experiences. Click through the list to read their stories.

Like psychologists, bartenders and hairdressers, financial planners sometimes hear some interesting tales. We asked planners for a peek into their most surprising client experiences. Click through the list to read their stories.

Keith Singer

Owner and President
Singer Wealth Management
Boca Raton, Fla.

Singer met with an 87-year-old client who said his wife of 62 years had died the previous year. “Thank God,” the man added.

“He explained that he had never loved her,” Singer says, “and added that he had told their grown children the same thing.”

The client went onto explain that his true love was a girlfriend he had lost touch with after he went overseas during World War II.

“After his wife died, he hired an investigator and found his first girlfriend, who was also widowed. They got married and he was finally happy,” Singer says.

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Geoffrey VanderPal

Founder and CEO
VanderPal Capital Management, LLC.

VanderPal came across a very Vegas-specific client while working there: A professional gambler.

"He told me that he wore disguises to fool security and get into casinos, where he counted cards to beat the house at blackjack,” VanderPal says.

Jason Kirsch

Financial Adviser
Marcum Financial Services
Deerfield, Ill.

A client very nearly went to the dogs at Kirsch’s practice.

“He told me that he was planning on investing seven figures in an app called Woof, which was essentially Tinder for dog owners,” Kirsch says. “He didn’t go through with it.”

David Hunter

Horizons Wealth Management
Asheville, N.C./Greenville, S.C.

When Hunter was 24, he and a 74-year-old client had an uneventful meeting—or so he thought.

“She called my boss a month later and said that she was extremely upset over the fact that I’d accused her of sexually harassing me during our meeting. I was lucky that she didn’t tell the story the other way around,” he says.

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Dennis Crowley

Vitruvius Capital Consultants
Greenville, Del.

Early in his career, Crowley met a prospective client and asked to speak with his accountant to discuss his tax strategy.

“He answered, ‘I don’t have a tax strategy. I just don’t pay them,’” Crowley says. “He said that his research had shown that, while it is a crime to fail to file tax returns, it is not a crime to fail to pay taxes. So he dutifully filed proper tax returns every year and refused to send the IRS a nickel.”

Joe Henderson

Senior Financial Planner
Vintage Financial Services
Ann Arbor, Mich.

Henderson remembers clients who asked him for a few moments of privacy in his office.

“When I returned, they were engaged,” he says.

Scott Smith

Principal and Senior Financial Adviser
Olympia Ridge - Personal Financial Advisers
Rochester Hills, Mich.

A couple visited Smith for routine estate planning. They ended up having a meeting that was anything but routine.

“I kept seeing an unfamiliar name listed as the contingent beneficiary on the wife’s accounts and insurance policies. I asked her who this person was,” Smith says. “She began to cry, saying that this was the child she had when she was 16-years-old. She had never discussed this with her husband. I left them in the room to talk; they were there for four hours.”

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Tim Brennan

Tim Brennan
Ariadne Wealth Advisors
Pembroke, Mass.

Brennan got a call from a woman who said she needed help investing inherited money.

“She said that she had met a guy from Venezuela online who said he would trade options for her and return 10% a month, but figured she should look around,” Brennan says.

Brennan said her needs weren’t a good fit for his practice, but strongly advised her against giving the man any money.

“Two weeks later she called me back and told me that she gave some money to that guy and he lost it all in two days. He didn’t know that could happen, she said, and promised to pay her back.”

Nate Byers

JBC Wealth Advisors
Madison, Wis.

During a meeting with a married client couple, the husband asked Byers if they needed long-term care insurance.

“The wife responded that, if she is ever at the point of needing long-term care, she knows what she needs to do, and if she can’t do it, her sister knows what to do,” Byers says. “I can still remember the embarrassed look on the husband’s face. I’ve had other clients say things like that, but clearly in jest. Her comment felt real.”

Leslie Ransom

Indie Financial Planning

Account rollover? Not for this client, Ransom says.

“I had a client who had saved some money and wanted advice for what to do with it. The nest egg, this person said, was about $20,000 — in cash, sitting in a safe deposit box.”