Modern capitalism was born at the beginning of the 17th century in what is now the Netherlands. In a bold and revolutionary move, the Dutch East India Company (formed in 1602) distributed the risk of sending ships out to buy nutmeg, cinnamon, cloves and other exotic spices in the faraway ports of the Indian Ocean and the South China Sea by selling shares in the company on the Bourse, one of the first iterations of a stock exchange. This was a profound economic transformation from the feudal model, in which ownership and wealth were concentrated in the crown and the gently born. By the 1660s, those shares, purchased by Holland\u2019s endlessly energetic burghers, were earning annual dividends of 40 percent to 60 percent. Consequently, the Dutch became the richest people on earth.And they took that wealth and invested it in...tulips.It seemed like a good idea, a bold but reasonable investment strategy. Thanks to its sandy, well-drained soil, Holland was an ideal place to grow tulips. The cost of entry into the market was low, and a single, particularly prized bulb could sell for as much as 2,500 guilders\u2014at the time, the yearly yield of a good-sized farm. But unlike the Dutch East India Company model, the tulip business lacked the sine qua non of any bold endeavor: risk mitigation. Once one\u2019s entire wealth had been converted into tulip bulbs or tulip futures (which many did), once one had converted one\u2019s entire farm to tulip cultivation (as many, many did), there was no turning back, no exit strategy. And when the bubble burst (the bulbs had, of course, minimal intrinsic value; they were, after all was said and done, just flowers), the country and its people were devastated.From this sad tale comes a calculation that hundreds of years later is embedded in all the applications we received for this year\u2019s 18th annual CIO 100 Awards: To be bold is to assume risk; without risk, there can be no reward. But there\u2019s no reward that justifies an endeavor lacking a plan to transfer, diminish or distribute risk.Time for BoldnessWhen the Internet became the rage in the 1990s, the need for boldness in thought and action was assumed. It was the price of admission to the great wealth-gathering game. Every day seemed to bring forth a new, transformative technology. Every other day brought forth a new business, a new paradigm and a spate of periodicals (including this one) chronicling and celebrating the new, new thing, whatever it may have been. The accepted wisdom was that companies that did not act boldly, did not innovate, did not change restlessly and relentlessly would not survive. Who had time to worry about risk? While you were worrying, the market\u2014and your competitors\u2014would pass you by.And then the bubble burst. And almost overnight everything changed, including the accepted wisdom. Caution, especially as it concerned IT, became corporate America\u2019s watchword. Or, as Joanne Yates, distinguished professor of management in MIT\u2019s Sloan School and president of the Business History Conference, 2004-2005, says, "No one wants to be on the bleeding edge. People on average are afraid of technology and change."But now at long last, the wounds are healing. We once again look to the future of information technology with something approximating optimism. And when we\u2019re hopeful about the future, we\u2019re more willing to take risks. In this changing climate, CIO sought to identify enterprises that were choosing to be bold.We picked 100.Bold LeadershipWe surveyed these enterprises, asking them to identify the factors that contributed to the success of their bold endeavors and helped them create a self-sustaining culture of boldness. (Read the complete survey.) Overwhelmingly, they pointed to leadership. For leadership expert Michael Useem, director of the Center for Leadership and Change Management at the Wharton School, bold leadership entails "a willingness to get into the game, a willingness to take on responsibility" as well as "a self-disciplined ability to face the big decisions and make them."How We Chose The Bold 100\n\nRead MoreUseem, who is a mountain climber and takes his grad students trekking in the Himalayas to impart leadership lessons, believes these abilities can be learned. "Companies can teach it," he says.Useem, who is a mountain climber and takes his grad students trekking in the Himalayas to impart leadership lessons, believes these abilities can be learned. "Companies can teach it," he says."The sign of a good mountaineer is that they have learned from the prior mountains what cliff not to step off. It\u2019s the same in business," says Useem. "Going with your gut is a terrible idea unless it\u2019s informed by past experience; experience-informed intuition is a great platform for making bold decisions."For insights on how bold habits can be developed, nurtured and inculcated in your staff and your enterprise, see Senior Editor Alice Dragoon\u2019s "8 Tips for Bold Leadership," derived from a number of our Bold 100 CIOs. In "IT Rocks the Web," honoree National Gypsum\u2019s CEO, Tom Nelson, describes the key decisions he made and the expectations he set for IT to ensure that the company succeeded in its bold bid to convince customers to do their business online.Bold FlavorsOur honorees have been bold in many ways in the pursuit of many objectives. They\u2019ve transformed their business models. They\u2019ve created new products and services. They\u2019ve looked to generate new revenue while reducing their operating costs. They\u2019ve attempted to enter new markets and develop new business capabilities. They\u2019ve looked to attract new customers while strengthening their ties to those customers they already have. To achieve all these varied goals, they\u2019ve leveraged technology\u2014both new and old. They\u2019ve deployed their staffs and managed their budgets in creative ways. And because we believe that boldness is learnable, we\u2019ve endeavored to extract the lessons these companies have learned in the process of recreating themselves.In "At Play in the Fields of the New," by Technology Editor Christopher Lindquist, we look at three organizations that are using technology to reconfigure the competitive landscape in their respective markets. In "A New Blueprint for IT," also by Lindquist, we look at how several companies took the considerable risk of tearing up their old infrastructures in order to implement service-oriented architectures and, in so doing, made their businesses more agile and responsive to customers\u2014both internal and external. In "Putting People in Their (Right) Place," Senior Writer Meridith Levinson focuses on four enterprises that changed the rules for their employees in order to meet new business demands, and in "Bold on a Budget," Page 72, by Senior Writer Ben Worthen, we learn that bold endeavors do not necessarily require huge financial investments. Bold, Not FoolhardyIn all these stories, we keep in mind the lesson of the Tulpenwoede, the tulip mania, and never take our eye off the risk. Neither did our honorees. Some mitigated risk through relentless testing of new applications; others refused to sunset old systems until the new ones had been fully accepted. In most cases, change was introduced incrementally. In almost every case, business leaders and end users were brought into the process early. In all cases, the mitigation plan was kept firmly in the project\u2019s foreground.As Useem puts it, when you begin to scale a mountain, "you need drive and boldness to get up. But you also need to look at the weather, make sure you have the right equipment and know how to use it. Everyone on your team needs to know the risk and what to do, and only then do you leave the parking lot. You want people who are bold but not foolhardy."On a mountain, getting to the top is optional."Getting down safely is required." Managing Editor David Rosenbaum can be reached at firstname.lastname@example.org.