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one of the primary joys of my life for the past 20 years. I am endlessly fascinated by my fellow members’ stories and ever grateful for their willingness to share in a way that I, and other members, can learn from and grow. Not only were the many chairs at Tiger 21 helpful in identifying members with great stories, but a few of them also shared their own important experiences. (Thank you, Cal Simmons, Barbara Roberts, Charlie Garcia, and Chris Ryan, for your stories and insights.) I also want to recognize the key professionals on the Tiger 21 staff with whom I have worked for the last decade and more. We could not have created the platform from which this book springs without your creativity, dedication, and brilliant execution.

      A first book project is an entirely new experience, and at each stage, expectations have to recalibrated. My agent, Jim Levine, has been a great guide along the way. We were extremely lucky to have received interest from Steve Isaacs at Bloomberg Books, and Tula Weis and Sheck Cho at Wiley. I am indebted to the whole Bloomberg and Wiley teams for giving me this opportunity.

      I am sure I have forgotten or omitted many others along the way whose insights added immeasurably to the finished product. Over the past three years, I sought and received input from countless people, many of whom made critical differences along the way. Thanks to all of you.

      While I am primarily responsible for the creation and evolution of Tiger 21, as an organization, it has grown far beyond my specific contributions. My initial partner, Richard Lavin, ran Tiger 21 for its first five years. His attention to detail and commitment to the concept allowed us to get up and running. He taught me a lesson based on his deep restaurant experience: Kiss your customers on all four cheeks. We simply could not have grown into the organization we have become today without Richard’s initial participation. Then Tommy Gallagher stepped in. In a remarkably short time, Tommy took a small New York–based organization and created a national footprint. We saw remarkable increases in our membership and our staff during his tenure. Tommy has been a steadfast partner for almost all of Tiger 21’s history, and one of my best friends to boot. I have been pleased to share this journey with him. In 2009, Jonathan Kempner joined Tiger 21 as president and brought experience we simply never had. While providing a steady hand for the six years he was at the helm, he was almost always a real pleasure to work with. When he insisted on developing our annual conference, despite my objections, it turned out to be one of the most transformational activities in our 20-year history. Jonathan forever changed Tiger 21 with his insights about how to build a large organization and how best to serve our members interests’. We now are being led by Barbara Goodstein as CEO, and under her leadership, we are growing even faster. We have just opened London, and I can’t wait to see what evolves in the coming years.

      I have had the good fortune of being associated with Harley Frank for almost 35 years. Over that time period, we have worked together in almost every business I have been involved with, and he has always brought a unique perspective and unmatched creative energy. The idea of translating the wisdom from our members’ experiences into a book was Harley’s, and for a number of years he relentlessly pushed me to write it. Without Harley’s initial energy pushing me forward in the early stages, there would never have been a book. Harley impresses me with his interesting, creative one-off marketing, branding, and promotional ideas more than anyone else in my orbit. While I hope this book turns out to be the best of them, it is only one of many of his ideas that I have benefited from over all these years.

      Finally, it is my wife, Katja, and our four children to whom I am personally most indebted. All the sacrifices, schedule changes, trip cancellations, missed dinners, interrupted dinners, and endless distractions that my personality has driven me to accept have most often come at the expense of spending time with each of them, and most of all, with Katja. Without their support, encouragement, acquiescence, and acceptance, the activities and events I have shared in this book, and the book itself, would never have come to be. For that and so much more I am forever grateful.

      Introduction

      Every year in the United States, half a million men and women decide to take the biggest risk of their lives in pursuit of a dream. To get there, some of them take out a second mortgage on their homes. Some of them wipe out their savings. Others borrow money or seek investments from friends and family. Some drop out of college. Others uproot their families. And some leave high-paying jobs with corner offices at prestigious companies.

      They all do this in order to start a business of their own. To be their own boss. To create jobs for people in their communities. To make something entirely new, or perhaps just something much more efficient. And, yes, frequently with the hope of making millions of dollars.

      These risk-takers decide to leap despite the fact that the odds they face are, by any reasonable measure, absolutely dismal. About two-thirds of the businesses they start, according to the Small Business Administration, will fail within 10 years. And that’s a sunny estimate! Forbes magazine claims that the number of deaths is closer to 90 percent.1 A Harvard Business School professor recently studied 10 years of data on more than 2,000 startups that were so well planned and positioned that they received venture capital funding. But even 75 percent of these best picks failed to return their initial capital.

      When you read those statistics it seems a miracle that so many Americans even try to start a business, knowing it might mean going broke; losing money borrowed from family, friends, and investors; or potentially damaging or destroying their reputations.

      Who are these seemingly delusional people who dwell among us? We have a fancy word for them —entrepreneurs– but that title doesn’t begin to capture this unique breed of exceptionally gritty people.

      Chances are when you hear the word entrepreneur you think of Facebook’s Mark Zuckerberg in his Harvard dorm room or Apple’s two Steves (Jobs and Wozniak) tinkering in a Los Altos garage. Or perhaps the scrappier startups of Shark Tank leap to mind.

      Me? I think of people like Gary Mendell, who started flipping burgers and went on to build a hotel management and development company that sold a $300 million hotel portfolio to Starwood. Or of Pete Settle, a lawyer and engineer, who founded a school-bus company that became one of the nation’s largest student-transportation providers. I think of Will Ade, who lost his job at a Texas oil firm and started his own wildcat exploration consultancy based in Singapore, giving him a net worth beyond anything he could have ever dreamed of.

      If you’ve picked up this book, chances are you see yourself as a future Zuckerberg or Jobs or Mendell or Settle or Ade. Or perhaps you’re wondering if you have what it takes to become a professional daredevil.

      Maybe you’re a bit further along your journey – 5 or 10 years into your successful startup. You’re wondering whether or not to sell or go public and finding that even though you’ve got lots of friends in finance, their advice is coming up short. Or maybe you’re like me: a person who’s built a successful career on taking risks that others deemed crazy.

      I got in the game at 24 years old after two jobs. I wanted to pursue a real estate development opportunity that I had been noodling on since I was 17, right after I dropped out of freshman year at the University of Michigan. That summer, I was working in a warehouse on the Jersey City waterfront. Only a few thousand feet across the Hudson River from the end of the pier where I took my lunch breaks, Wall Street was bursting at the seams with new data centers and expanding operations. Those expansions were starting to leapfrog the Jersey waterfront to remote suburban campuses, which felt like Siberia to employees. The railroads had owned most of the Jersey waterfront across from Manhattan, and their midcentury bankruptcies and reorganizations had blinded developers to the obvious advantages of setting up data centers and back offices five minutes from Wall Street.

      My idea was so bold that most real estate veterans did not think anyone could pull it off – never mind a no-name twenty-something who’d never developed anything in his life. I wanted to convert a rundown, 2.5-million-square-foot warehouse into the new home for lower Manhattan’s high-tech office expansion plans.

      After 18 months and a couple of false starts, the $25 million deal went through and the Harborside Terminal quickly became America’s largest commercial renovation project. Little could I have known that the project, which over the next three decades evolved into a mixed-use

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