When friends, family beg for bailouts © Photodisc/SuperStock

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When friends, family beg for bailouts

Having plenty of money in a down economy can create a special kind of stress -- when people you know come looking for financial aid. How much should you help?

[Related content: debt, debt reduction, credit cards, bills, loans]
By BusinessWeek

After the economy tanked in 2008, Rob DeSantis' phone began ringing. Suddenly friends, family and neighbors were begging him for financial help. It's not hard to see why. DeSantis is ultrawealthy, having co-founded Ariba, a dot-com-era startup that pioneered online purchasing for large companies.

In one week in October 2008 alone, DeSantis says, the requests totaled half a million dollars. An additional $1.5 million in pleas came in December of that year.

The cries for help moved him profoundly. "My first thought when they call is, 'Oh, no, not you, too,' and it makes me want to help," says DeSantis, who is working on a book and looking into green technology. "They want to keep their house, their company, whatever. It pulls on your heartstrings."

DeSantis has plenty of company recently. There's the billionaire whose brother-in-law stopped speaking to him after he refused to increase the man's small-business loan. The two friends who fell out after one asked the other to pay off her mortgage.

Then there's the 21-year-old trust-funder whose strapped friend was caught shoplifting. DeSantis hadn't heard from her for a year, and suddenly she was on the phone asking whether he could bail her out of jail. "This hurt," he says, "because it told me she looked at me as a sort of bank."

As the government has stepped in to bail one industry after another, America's affluent have done the same for their friends and families. And just as the feds' largesse has had unintended consequences, often so does the personal bailout. Givers can feel put upon, recipients beholden. Like many in his position, DeSantis sought professional help. He called his wealth therapists: Joan Indursky DiFuria, a commodities executive turned family counselor, and psychologist Stephen Goldbart, who together run San Francisco's Money, Meaning & Choices Institute.

AS the Great Recession got rolling, DiFuria and Goldbart say they found themselves rushing from mansion to pied-à-terre, helping the moneyed class figure out how to deal with down-and-out friends and relatives without turning them into welfare cases. DiFuria says clients are plagued with thoughts like: "Should I be helpful? In what way should I be helpful?"

Fixing others' lives

Like many people who start life in humble circumstances, DeSantis says he has struggled with "being good at being rich." When Ariba went public in 1999, DeSantis fleetingly became a paper billionaire at age 38. It was a head trip for a guy who grew up in a 900-square-foot house. That, in part, is why DeSantis' financial adviser introduced him to Goldbart and DiFuria in 2002. At the time, the therapists were helping other extremely rich people handle what Goldbart and DiFuria had dubbed "sudden wealth syndrome."

DeSantis' first impulse was to shower the people he loved with lucre -- to transform lives with one check. It wasn't long before his largesse began to backfire. One recipient in particular stands out. DeSantis paid off all of the person's debt -- an act of generosity that cost him about half a million dollars.

"I wanted to give him a get-out-of-jail-free card," recalls DeSantis. When the economy tanked, guess who came knocking? DeSantis' beneficiary was looking for another handout, pleading that without it, he would lose his house and slide into bankruptcy.

DeSantis set up a session with Goldbart and DiFuria. He was torn up with anxiety. He felt that if he didn't help the guy, no one would. Over sandwiches and bottled water in DeSantis' home office, Goldbart and DiFuria reminded him of the best practices they had worked on for giving: analyzing each request on a case-by-case basis, outsourcing the negotiation and management of the requests to a third party, and seeing if there were nonfinancial ways to help friends in need.

Continued: 'I've hurt him more than I have helped him'

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