When the economy tanked this fall, Rob DeSantis's 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 alone, DeSantis says, the requests totaled half a million dollars. In December came another $1.5 million in pleas.

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 at deals in green technology. "They want to keep their house, their company, whatever. It pulls on your heartstrings."

DeSantis has plenty of company these days. 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.

The 21-year-old trust-funder's strapped friend was caught shoplifting just before Christmas. He hadn't heard from her for a year, and suddenly she was on the phone asking if 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 bails out one industry after another, America's affluent are doing the same for their friends and family. And just as the Fed's largesse can have unintended consequences so, too, can 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.

In recent months, DiFuria and Goldbart say they have been rushing from mansion to pied-a-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, the then 38-year-old fleetingly became a paper billionaire. 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 this 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 this fall, 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 in November. 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, seeing if there were nonfinancial ways to help friends in need.

They discussed what had happened the last time DeSantis had helped this person. How after bailing him out DeSantis had watched the man quit his executive-level job at a major corporation, run up his credit cards, and use his house as an ATM. How DeSantis had tried positive persuasion to get him to change his free-spending ways: "Hey, you're in a great position to be thinking about what you'll be doing," DeSantis would say. How the message never seemed to take.

"I feel like I've hurt him more than I have helped him," DeSantis told Goldbart and DiFuria. The therapists were emphatic. "If you don't break off this trust-fund syndrome, Rob, you'll always be enabling him," Goldbart said. Armed with that advice, DeSantis turned down the request. And then something amazing happened: After being cut off, DeSantis' supplicant got a job and saved his house from foreclosure. "I have made the decision to not help anyone to just make it go away," says DeSantis. "If there is acute short-term pain I can bridge, I've done that. But if it's a 50-year problem, there are other ways."

Former Charles Schwab chief executive officer David Pottruck and his wife, Emily, an author and social activist, are among the Bay Area's leading philanthropists. Besides donating millions of dollars to charities over the years, the Pottrucks have given generously to friends and family, often to people David grew up with.

In most cases, the Pottrucks bailed out people with no questions or strings attached. But now and then, Emily was rankled by some recipients' seeming sense of entitlement. "I think there are people out there who think, 'Oh well, he's so rich, what does he care?' "

Even before Wall Street collapsed in September, the couple was inundated with requests for money. The amounts ranged from thousands to hundreds of thousands of dollars, for everything from living expenses to tuition to house payments. Like most couples, the Pottrucks sometimes argued about money, especially their philanthropic choices. After hearing them agonise over how much money to give their children, a banker friend recommended they see Goldbart and DiFuria.

At first, Emily was deeply skeptical about how two therapists could help with financial matters. "I thought, 'Gag me with a spoon,' " she recalls. Then, during a six-hour retreat at the Pottrucks' San Francisco home, Goldbart and DiFuria investigated the couple's values about money, what was important to them in life, how much money they should give their kids, and how they could strategically go about achieving their philanthropic goals.

By the end of the session, Emily felt she and David understood each other's money values better than they ever had. They had different priorities--but that didn't mean they had to judge each other.

Gift, loan or refusal?

As all the requests for money began rolling in, Goldbart and DiFuria counseled the couple to provide for needs, not wants. They told the Pottrucks it was not necessary to give carte blanche; in some cases, loans would be appropriate. They also taught them how to ensure that the gift and loan agreements were on their terms, not the recipient's.

Emily put this advice to use with two people this fall. After hearing the requests and empathising with the circumstances, Emily politely responded that they would be happy to extend a loan, but that they should also talk about a reasonable repayment plan. One person took them up on the offer. The other, "we haven't heard back from," says Emily.

Every four months, Goldbart and DiFuria meet with two twentysomething siblings at the Executive Inn & Suites in Oakland. Two adjoining rooms become their makeshift retreat centre. Three years ago, the brother and sister lost their father, a self-made multi-millionaire. They began seeing the therapists because the trustee of their estate didn't want the wealth to negatively effect them. This fall, the son mentioned that he had a friend who needed several thousand dollars. "He wanted to sort of look at it as if I was a bank loaning him money," he told the therapists.

Goldbart and DiFuria reminded the son of an earlier occasion on which he had lent money to a friend. "They reminded me of how it changes the relationship when you do that," the son says. He recalls feeling as though he were playing the father role. Goldbart and DiFuria proposed giving anonymously.

The son had another idea: "If a friend is spending more money then they own, I'd be more than willing to pay for a couple of sessions with a professional regarding debt and money management," he says. "Treating the symptom, throwing money at it, isn't going to provide long-term benefit for anybody."