The writer at the W Hotel: "It had become my family's hotel California. We could check out any time we liked. But we could never leave."

The housing bubble. The dot-com stock craze. The Florida land rush. The Dutch tulip mania. Throughout history, men have jumped at the opportunity to get rich quick, even when the opportunity was clearly too good to be true. Why do we fall for it every time?

Blame the reward centers in your brain. The nucleus accumbens and ventral tegmentum. Both areas flood with the neurotransmitter dopamine when you have a chance to make money from a gamble, says Russell Poldrack, Ph.D., an associate professor at UCLA’s Brain Institute. As potential riches increase, so does the dopamine flow. “Dopamine is the target for cocaine and amphetamines,” says Poldrack. “It’s what really drives people regardless of the consequences.”

Perhaps worse, success begets even riskier behavior. In other words, successfully flipping one house makes your desire to flip another even more intense, says Poldrack.

How can you rein in your reward centers? It’s not easy. Humor and sex are great distractions, because they trigger the same midbrain response, says Poldrack. But the best advice is to retain your objectivity and historical perspective. “It’s fun to swing for the fences,” says Robert Strong, Ph.D., a professor of investment education at the University of Maine. “But before you do, remind yourself of all the things that can go wrong.”

Then go have sex.

REBECCA SHILLENN

A Flip Too Far

The writer at the W Hotel: “It had become my family’s Hotel California. We could check out any time we liked. But we could never leave.”

By Mark Millhone Photos by MacKenzie Stroh

If you have to be homeless, there are worse places to do it than in a four-star hotel. At least you’ve got a roof over your head and a swell complimentary breakfast. If you wake up early, you can hit the buffet twice without too many people noticing and save the extra for lunch. For dinner, you learn to skip room service and live with the stares you get carrying groceries past the doormen, with your kids in tow.

The Union Square W Hotel in Manhattan had become my family’s personal Hotel California—we could check out any time we liked, but we could never leave. We had no place to go.

We checked in when our developer promised our new apartment would be ready “in a week or two.” That turned into a month, then two. Nothing to do but sit tight, and I do mean tight—a family of four plus our dog, Spike, wedged into a cramped hotel room—and keep racking up the hotel bills, waiting to move into a new dream home that we could no longer afford to actually live in.

Strange as it may seem, I was okay with that. I didn’t see it as losing a home. Not anymore. I saw it as winning an argument.

FUZZY MATH

My marriage to my wife, Rose, is a passionate disagreement over almost everything. Case in point: our home finances. She’s a big believer in “paying it forward”—that is, buying things today that you hope to afford tomorrow. According to her revolutionary supply-side economics, a.k.a. “Rose Math,” the need for money somehow creates a supply, as if the capital she’s tied up in her shoe collection is what she leveraged to attain her enviable success as a business executive. Sure, it’s fuzzy logic, but for a surprisingly long time, Rose Math has worked.

Thanks to her theory, we enjoyed a very good ride on the ever-expanding Manhattan real-estate bubble, flipping our way through three different residences in 5 years, each home nicer than the last. Okay, fine, I’m no victim. Flipping is addictive. You start to think that if you’re not overextended, you’re underinvested, that the only way to stay ahead of the game is to get behind the eight ball. It’s a rush. When the flip is on, you feel like Tarzan, swinging from one place to the other, buying low and selling high, your feet never touching the ground.

Problem is, eventually you hit a tree. Ours came in the form of a sudden $3,200-per-month assessment on the loft we were selling. The building needed a new elevator, and the condo board had to take out a big loan.

No one wants to buy into a troubled building. Unless, of course, the price is right. We slashed our asking price until it hurt, then until we bled, and finally, to the bone. By the time we sliced off enough to attract an eager buyer, we were far south of where we thought we’d be when we made our commitment to buy the new apartment. And we had no idea how we’d make up the difference.

FOUR-STAR BANKRUPTCY

Staying at the W was Rose’s idea. Yes, it was a splurge, but Rose argued that unloading the loft was so stressful we deserved a mini-vacation. Plus, the W’s convenient location would save us hundreds in cab fare. From our 17th-floor hotel room, I could look down upon the handsome redbrick office building where our accountant, Abe, had his offices. Having him right across the street would be terrifically convenient when it came time to file for bankruptcy.

A month into our stay, with our developer coming up with increasingly creative reasons why the new place wasn’t ready, I declared this flip officially flopped. We had flown too high on mortgaged wings. Even Rose had to accept it now.

I set up a meeting with Abe to discuss our only realistic option: Put the new place on the market immediately, find a cheap rental, and crawl under a rock until the storm blew over. I said my piece and then offered Rose my big, strong shoulder to cry on.

She pushed me away. “I will die before I give up that apartment!” Think Scarlett O’Hara in Gone with the Wind: “I will never be hungry again!” Then, as if to underscore her willingness to die for the apartment, she succumbed to a massive coughing fit. She’d caught some kind of bug during our stay at the W.

Abe and I looked at each other and shook our heads. “What’s our bottom line?” I asked.

“Well, since Rose’s income looks fairly fixed for this next year, basically it’s up to you. To afford that apartment, you will need to double what you made last year.” Gulp.