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 office, retail, hotel, and condominium complex, would be viewed as a vanguard in terms of waterfront development and one of the most successful real estate deals in New York metropolitan history.

Four and half years after we bought Harborside, my partner and I cashed out. We had achieved a level of success beyond anything we could have imagined.

In the decades that followed, I had a few more victories, but I also endured some painful defeats. Along the way I was forced to come to grips with my own limitations. If you’re smarting from a business that went bust or learning the hard lesson of what risky really means, trust me. I’ve been there.

One important lesson I realized early on was that the undergraduate and graduate degrees I proudly earned at MIT’s Sloan School (after returning to college following an 18-month stint of work I did after dropping out of Michigan) rarely provided the critical difference in the making of a deal. Don’t get me wrong, having B.S. and M.S. degrees from MIT has been one of the fastest ways to build credibility during my career, and the amazing education I received there gave me perspective and knowledge that I could not have easily duplicated elsewhere, and I am proud, to this day, to be an MIT alum. But what saved me, time and time again, wasn’t my education, but the wisdom of other people who had already been through something I was wrestling with for the first time and their perspectives gained over decades of experiences I was yet to have.

See, that first deal of mine would never have happened without my mentor and partner, David Fromer. He was twice my age: I was in high school while the Vietnam War was raging; David had won three Purple Hearts and a Bronze Star during World War II. He’d then spent 30 years buying, building, and selling real estate in Los Angeles, London, and Saudi Arabia. Without David’s wisdom, experience, and penchant for risk taking, that New Jersey waterfront project, and all the dozens of deals that came after that for me, wouldn’t have been possible.

Common wisdom has it that the best teacher is experience. Indeed, in my 40-year career as an entrepreneur, I have found that the best teacher is experience—someone else’s experience. Each and every time, what helped me build multiple businesses (and nonprofit organizations, too) was the hard-won advice of other entrepreneurs.

Nineteen years ago, after I sold my second company, I felt that I was more than a little at sea, and I was in desperate need of advice from others who had traveled the same road before me.

I decided to do something about it.

The Investment Group for Enhanced Results in the 21st Century (Tiger 21)—what is today the premier peer-to-peer learning network for high-net-worth wealth creators in North America—was the result. It began with a single group of six entrepreneurs in New York City who had all sold their businesses. All of us were post our liquidity event, and we all felt challenged to wisely preserve our wealth, while also exploring issues of relevance, legacy, family, philanthropy, and the big what’s next.

It turns out that I wasn’t the only entrepreneur who craved the advice and community that only fellow entrepreneurs could provide. Unlike those who work in hedge funds, banks, or traditional businesses, entrepreneurs lack the structure and institutional knowledge that these more established businesses provide.

Entrepreneurs need guidance—and not just when they’re starting out. They need guidance when they’re growing their companies and pulling them through the inevitable crises that pop up. Those lucky few whose businesses become valuable enough to sell need it even more. The right advice can position a sale to yield multiples of after-tax or philanthropic dollars that might have been lost because of poor planning or missed opportunities. It can save an entrepreneur from jumping into a sale prematurely and help prepare him or her for what comes next—which is often even more challenging. There are any number of people and firms who will offer you investment and management advice for a price. But objective, disinterested guidance from fellow entrepreneurs who have already built and sold companies of their own is awfully hard to come by.

Today, Tiger 21 has grown beyond my wildest expectations. We have 40 groups in 35 cities across the United States and Canada. All told, our 500-plus members have a collective net worth of over $50 billion (and control assets with value in excess of $100 billion, when you add the financial and real estate assets some of them manage for others). We are currently expanding around the globe. Our first London group convened in the spring of 2017.

Although we have our share of current and former partners in Wall Street firms and major real estate companies who bring critical insights from the front lines of finance to our meetings, the majority of our members—some of whom you will meet in these pages—made their fortunes on Main Street, in fields ranging from coin-operated washing machines and medical supplies to payday loans, tax liens, and legal services. The majority of them come from working- and middle-class families; many are still friends with their high school classmates. Most are justifiably uncomfortable about discussing the unique challenges and opportunities that come from having made it big, and when they do open up, they tend to be more inclined to talk about their screwups than their successes.

Once a month, all of us break away from our businesses, investments, philanthropies, hobbies, and families to spend the day speaking frankly and confidentially with one another about everything relating to our businesses and even our lives and families. Many members refer to Tiger 21 as their “personal board of directors”—their most reliable source for honest, no-holds-barred advice in just about every important aspect of their lives. I’ve come to think of it as a one-of-a-kind laboratory of success.

This book started when I asked myself a question: What have I learned from my nearly 20 years of intimate connection to some of North America’s most successful and creative entrepreneurs?

A lot, it turns out. Beyond the business tips and investment advice and support that I was looking for in the beginning, I’ve gained a deep and highly personal understanding of what makes me and other entrepreneurs tick—knowledge that would be incredibly useful to anyone who has their own idea for a startup, is building a business, is thinking about selling one, or who already has.

Access to this formidable brain trust generally requires a minimum of $10 million in investible assets and an annual fee of $30,000. Until now! In the following pages I will take you deep inside our exclusive network—and happily waive the fee.

Sharing this wisdom has never been more important. That’s because we are at a very precarious economic and political moment in our nation’s history. The wealth gap between the rich and poor is starker than ever. And our country’s once-thriving middle class is eroding, largely thanks to globalization and the advent of brilliant new technologies.

Concern over the lack of good jobs here at home reached a fever pitch during the 2016 presidential election, in which candidates of both parties promised to bring jobs back—even if it meant passing protectionist policies that, in reality, would actually harm the very people they are trying to help. Such promises create false hopes.

The hard truth is that the jobs that have been offshored to China, Mexico, and the rest of the developing world only represent about 15 percent of the job losses everyone is talking about. The rest—85 percent—were gobbled up by automation. No one is going to retire the robots that play a growing role in our factories. No one is going to unlearn the technology behind self-driving cars, and no one is going to unplug the computers that run so much of our lives.

If we want to create jobs in this country, we can’t look to steep tariffs on imports or impenetrable borders. We need to look to entrepreneurs.

Historically, entrepreneurs have created many of the private-sector jobs that have underpinned our economy, contributing mightily to the steepest rise in standards of living that the world has ever seen. The same has been true of the past 70 years. Jobs haven’t primarily been created by the big, established firms, but by the entrepreneurial enterprises that continue to be the engine of American economic growth.

This will be the case even more in the future. The primary source of new, sustainable jobs will be small companies founded by entrepreneurs, some of which will grow into behemoths in the years to come.

Those entrepreneurs will need all the support they can get from political leaders in Washington and statehouses across the nation. Some would define the challenge as removing all the obstacles that have been erected. The problem is that right now, far too many members of the political class, even the most pro-business among them, have a faulty understanding of who entrepreneurs are and why they do what they do. My hope is that the stories in this book will give policy makers a better understanding of how we tick and, thus, what we—as a country—need the most.

Entrepreneurs are not saints, of course, nor are we public servants, even though the enterprises we’ve created have contributed mightily to our nation’s prosperity.

But if working on this book has taught me anything, it is that successful entrepreneurs are a special species in the world of business. They are different from corporate leaders (though many of the best entrepreneurs are also great leaders) and from professional investors (though many talented investors have built their own companies). And while the best entrepreneurs do display certain psychological and character traits that are common to success stories in other fields—like self-discipline, grit, and tolerance for risk—I would bet that if you took a random sample of entrepreneurs, you would find that the most successful among us tend to have even higher levels of those traits, supercharged by an optimism that psychologists would label delusional. When you add to that mix the ambition that a poor or lower-middle-class background or a broken home can nurture, a unique set of traits comes into focus.

If you come up short on too many of those traits, even years of study, planning, and dedication will not suffice to make you an entrepreneur. But if you do have them—and I suspect you might if you picked up this book—you can cultivate and develop them.

To those people who can’t stomach the idea of going back to school, or formal education in general, take heart: Many of the most successful entrepreneurs I know are not book smart, but are quite brilliant in their own ways, and they are often particularly well endowed with a level of emotional intelligence that makes them inspiring leaders. They are often endlessly curious, too. I’ve also detected a high incidence of learning issues, such as dyslexia and attention deficit disorder, among entrepreneurs. It seems the more obstacles they have successfully overcome, the more likely entrepreneurial success becomes.

One of the most important lessons I’ve learned can be summed up in a quote from David Russell, one of our original Tiger 21 members: “When I was young, they used to say on TV, ‘The smart money is doing this, the smart money is doing that.’ I finally got to be wealthy, and I find out that ‘the smart money’ is just as stupid as everyone else.” Amen to that. As smart as you and I might be in one area or maybe two, we are likely to be clueless in many others. I’ve been humbled enough times to admit that I have my own blind spots—and I’ve relied on other entrepreneurs to help shine a light on them. I sincerely hope this book will help you do the same, no matter where you are on your journey as an entrepreneur.