04/24/2012 09:20 am ET Updated Jun 24, 2012

Daring Deals and the Art of Taking Risks

I love hearing stories about people who take risks to make life-changing deals. Wasn't it Donald Trump who once said, "Deals are my art form. Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals. That's how I get my kicks"?

The legendary Brazilian Court Hotel in Palm Beach inspired some great deals. The Spanish Mediterranean-style hotel, hidden behind high stucco walls, lush tropical foliage and serene courtyards has had a storied past. In the early 1950s, Eugene Meyer, who owned The Washington Post had an initial meeting at the Brazilian Court to buy The Washington Times-Herald. The ultimate purchase and merger of the two papers would alter the history of The Washington Post, send circulation skyrocketing and give the paper a 70 percent share of the DC market.

Actually, some say that after the stock market crash of 1929, investor Vincent S. Mulford, more or less obtained the Brazilian Court in a high stakes bridge game for $125,000. And as far back is 1926, when the hotel was built, New York architect Rosario Candela didn't follow the de rigueur Palm Beachy ethic of Addison Mizner, so his deal was to keep the blueprints of the property hidden behind velvet ropes. Even now, the baroque centerpiece of a fountain, suites with bronze fixtures and Provence-style wood shutters still evoke an earlier time at the hotel (Café Boulud restaurant there and the hotel's art gallery adds a fetching touch too.)

So thinking about great deals, I asked some people about some of their best ones and here's what they shared with me.

Mario Batali, award-winning celebrity chef, author, restaurateur and television personality:

The best deal I ever made was opening my first restaurant Po in New York City in 1993 for $35,000. I had borrowed my share of the money from friends. So my business partner and I had to make the restaurant work within our small budget. We took over the lease of an Indian restaurant that had already been there, but thankfully, we didn't have to pay any key money. The restaurant was kind of a dreamy hole-in-the-wall. The bar was covered in tin ceiling tile that I found on the Lower East Side for $40. I managed to put in a new ice cream freezer and refrigerator. I went shopping at the green market for food. I created a six-course tasting menu for $29. The pasta dishes like the white bean ravioli were $10. It was wonderful planning menus and taught me how much adored every aspect of restaurant ownership. I was the only chef. It was a risky venture, but I loved it. After a slow few months, Eric Asimov with The New York Times reviewed us and that changed everything. The restaurant suddenly became very successful. The word of mouth was incredible. In 2000, I sold my share in Po and made many, many, many times more than what I originally put into it. Having that restaurant made me realize that this was my calling and how much passion I have for my craft. My dream of owning restaurants was put into play.

Dan Myrick, co-director of the blockbuster independent film, The Blair Witch Project:

Just a few years after we graduated from film school, my classmate, Eduardo Sanchez and I co-directed a movie called The Blair Witch Project. We made the entire film for $35,000, which we scraped together, so we were ecstatic when Artisan Entertainment bought the movie at Sundance for $1 million. As a bone, they threw in a percentage of the box office if the movie made more than $10 million. No one in his or her right mind thought it would make that much. The first weekend, the film made $29 million (and has since grossed more than $240 million worldwide). To this day, I'm still flabbergasted that Blair Witch was so successful and became part of the culture and was featured on the cover of TIME magazine. In fact, my phone was turned off while I was selling the movie at Sundance and I was able to pay off a lot of bills. It helped me create my own production company, Gear Head Pictures. And I was able to buy a house for my mother in Florida, purchase my own house and get married. The best part is being able to take care of all the people who you love.

David Heyman, producer of the entire Harry Potter film series, which has grossed billions of dollars worldwide:

I was a struggling film producer and had moved back to London from New York. I had produced a small independent film called, The Daytrippers, and miraculously, Warner Bros. set me up with an office and staff for two years. (In fact, once the deal ended with Warner Bros. I was so broke that I had to pay for the office myself with my credit cards. And I was living in my sister's spare room. I love to read, so I decided to make books a focus of my business and read them before they were published to see if they would make good films. In early 1997, one of my employees read in a trade paper about an upcoming novel in which a boy goes to wizard school. I got the manuscript, but I thought the title was silly, so I placed it firmly on the low-priority shelf. Every weekend my staff and I took books home to read and discussed them on Monday. One Monday, a few weeks later, my secretary, who had loved the book, suggested I take it home over the weekend. As soon as I read the first paragraph, I was hooked. I stayed up all night reading it. I had no idea that it would become a phenomenon, but I related to the theme of being an outsider, and looking for a place where you belong. I felt a bit like Harry. I immediately called my friend at Warner Bros. telling him about this book. About a month later we began negotiating the film. I bought the movie rights to the entire Harry Potter series. I can't say what I paid for them, but I can say that I'm no longer living with my sister.

Bonnie Brown, author of Giigle: How I Got Lucky Massaging Google:

In 1999 I interviewed for a position as a massage therapist at a unknown start-up company that had just 40 employees called Google. I had just moved to the Silicon Valley, had gotten divorced after a 20-year marriage and was starting a brand new life. I was hired as a contract employee for 10 hours a week and my salary was $45 an hour. But usually I get $60 hour. I had dabbled a little in the stock market and knew a little about value of stocks. And since they weren't paying as well as other companies, I said, "in addition to my salary, I want options." My options were not only approved, which is unusual for a contract employee, but they were available monthly so I was immediately vested. Since I was paid hourly, I was given more options each hour I worked. My ten hours a week turned into five full days a week working at three different Google offices. In August 2004, the company went public and I was allowed to exercise my options six months later. On Valentine's Day in 2005, I remember hitting the send button to sell some of my shares. And at that moment, I became a millionaire. I cannot say how much I have, but I have enough money that I don't have to work another day in my life. I retired in 2005. Now I'm able to use my money to travel and I set up a private foundation so I can help people around the world. I helped finance a water purifying system at an orphanage in Uganda so the orphans no longer have to walk to a river for water. I have a private pilates instructor and get regular massages. But I still fly coach. I don't mind. I'm little.