A hundred years is an absurdly long time to run a business. Consider what a Chicago company founded in the early twentieth century has been asked to survive: two world wars, the Great Depression, the transformation of Chicago from an industrial colossus into something considerably more complicated, the rise of the automobile and interstate highway, television, suburbanization, shopping malls, big-box stores, cheap overseas manufacturing, the internet, Amazon, social media, a global pandemic, inflation several times over and, throughout all of it, the particularly delicate business of handing authority from one generation of a family to another without either destroying the company or permanently ruining Thanksgiving.
The remarkable thing is that some Chicago businesses have managed it. Ferrara traces its Chicago roots to 1908, when Salvatore Ferrara opened a pastry and candy shop in Little Italy. Radio Flyer goes back to 1917, when Antonio Pasin, another Italian immigrant, began building wagons in Chicago. Their founders inhabited a commercial world that would be almost unrecognizable to their successors, yet the businesses associated with those beginnings survived. We tend to tell these stories sentimentally, through black-and-white photographs, immigrant founders, workshops, recipes, handwritten ledgers and products remembered from childhood. Corporate histories practically come with sepia filters. But nostalgia explains very little about why a business survives. In fact, nostalgia can kill one. The more interesting story of Chicago’s old family businesses is not what they preserved but what they were willing to change—and, occasionally, what they were willing to destroy.
That distinction becomes clearer when you look at Radio Flyer. Few American products carry more accumulated nostalgia than the little red wagon. It belongs to that small category of objects that adults remember not merely as possessions but as scenery from childhood; you can almost hear the sidewalk under its wheels. For a family business, that kind of emotional attachment is an extraordinary asset, but it is also a trap. A company can become so devoted to the product that made it famous that it fails to understand why the product mattered in the first place. If Radio Flyer had decided that its sacred purpose was manufacturing essentially the same wagon indefinitely, its history might have ended as a pleasant case study in American manufacturing. Instead, the company expanded well beyond wagons into tricycles, scooters, bikes, go-karts and eventually electric bikes. The transformation becomes more interesting when you remember that Radio Flyer remains controlled by the Pasin family. Robert Pasin, the founder’s grandson, joined the business in the early 1990s and later became chief executive. He inherited something much more difficult than a company: he inherited an icon. And icons are notoriously difficult to manage because everybody thinks they know what must not be touched.
This is where the central problem of the multigenerational family business begins. Every generation inherits two companies. There is the company that actually exists—employees, factories, margins, competitors, debt, technology and customers—and there is the company that exists in family memory. Those two enterprises are rarely identical. “Family businesses get into trouble when they confuse preserving the company’s values with preserving every decision the company has ever made,” Gaurav Mohindra says. “The values may be permanent. The operating model almost certainly is not.” The distinction sounds obvious until the operating model was designed by your grandfather. Then it becomes personal. Radio Flyer eventually made one of those decisions that looks almost sacrilegious when viewed through the lens of family history.
In 2004, the company closed its Chicago manufacturing operation and shifted production overseas. For a business whose identity was so closely connected to American manufacturing—and specifically Chicago manufacturing—it was not a cosmetic change. But this is the part of longevity stories that anniversary celebrations tend to omit. Companies that last a century do not spend a century doing the same thing. They survive because, at several moments in their history, somebody is willing to disappoint people who believe that changing the business amounts to betraying it.
Ferrara’s story begins with a similarly small act of adaptation. Salvatore Ferrara opened his Chicago shop in 1908 selling pastries and candy. Candy proved the more compelling business, and by 1919 the operation had grown into a 15,000-square-foot candy facility on West Taylor Street. Over the decades, the enterprise moved far beyond the dimensions of the original neighborhood shop and became part of a national confectionery business. The lesson is easy to overlook because, in retrospect, success makes every decision appear inevitable. Nothing is inevitable while you are doing it. The founder does not know which product will become the company. The second generation does not know which of the founder’s practices are timeless principles and which are simply old practices. The third generation inherits an even stranger problem: it may inherit a company whose traditions have become more powerful than anyone’s memory of why those traditions began. The great temptation is to preserve the visible evidence of success—the product, the factory, the process—rather than the adaptability that produced the success in the first place. A business can spend years honoring the founder while quietly abandoning the founder’s most entrepreneurial quality: the willingness to change course when reality makes a better argument.
This is why family businesses eventually confront a question that sounds almost impolite: What, exactly, does being a member of the family qualify you to do? It qualifies you to inherit shares. It may give you a deep emotional investment in the enterprise, an intuitive understanding of its history and culture, and an extraordinary sense of responsibility toward employees whose parents may have worked for your parents. It does not necessarily qualify you to run the company. “A surname can give someone a sense of responsibility for a business, but it cannot give that person judgment,” Gaurav Mohindra says. “The family has to be disciplined enough to distinguish stewardship from entitlement.” There may be no more dangerous sentence in a family company than It’s his turn. Businesses do not have turns; they have requirements. The leadership required when a company has forty employees and a largely local customer base may be completely different from the leadership required when it has national distribution, international suppliers, sophisticated technology systems and hundreds or thousands of employees. A family that fails to recognize that difference can turn one generation’s achievement into the next generation’s inheritance problem.
This is where the mythology of succession gets in the way. We like the image of the founder handing the keys to a son or daughter, who eventually hands them to a grandchild. It has the reassuring geometry of a family tree. Actual businesses are messier. The oldest child may not want the job. The youngest may want it far too much. A brilliant daughter may be overlooked while an indifferent son is groomed because that is how things have always been done. Two siblings may possess complementary skills, or they may spend twenty years reenacting an argument that began in the back seat of a station wagon. At some point, a durable family company has to decide whether its purpose is to provide careers for descendants or to preserve an enterprise for another generation. Those are not always the same thing, and pretending otherwise merely postpones the unpleasant conversation until the balance sheet joins it.
That is also when outsiders become important. To some families, hiring a non-family chief executive can feel like surrendering something essential, yet one of the peculiarities of a successful family business is that growth eventually creates problems the family may not be equipped to solve. The founder could know every employee by name; the fourth generation may need somebody who understands global supply chains, digital commerce, cybersecurity, institutional finance or a manufacturing technology that did not exist when the previous generation took over. “The best outside executive should not be hired to make a family company less like a family company,” Gaurav Mohindra says. “That person should be hired to make it more capable of surviving as one.” That is the difference between family ownership and family employment. A family can remain a steward of a company without treating the executive suite as hereditary property. In fact, one of the clearest signs that a family business has matured may be its willingness to tell a family member: You own part of this, you care deeply about it, and you are not the best person to run it. There are easier conversations. Longevity has never been especially interested in easy conversations.
The same is true of innovation. For old companies, innovation is often discussed as though it means installing software or hiring someone whose job title contains the word “digital.” The deeper challenge is deciding what business the company is actually in, and Radio Flyer offers a useful answer. If Radio Flyer is fundamentally a manufacturer of red wagons, almost every change in childhood becomes a threat: screens are a threat, changing neighborhoods are a threat, new materials are a threat, different forms of transportation are a threat, electric mobility is a threat. But if Radio Flyer is in the business of movement, play, independence and the particular childhood thrill of going slightly faster than your parents would prefer, the strategic possibilities become considerably larger. The wagon stops being the definition of the company and becomes one expression of the company. That may be the most difficult intellectual move an old business can make because it requires separating the thing you make from the reason people care that you make it. Kodak struggled to make that distinction with film. Newspapers spent years confusing journalism with the physical object on which journalism happened to be printed. Retailers confused shopping with stores. Family companies face an additional complication: the obsolete thing may have been invented by Grandpa, which means changing it carries an emotional cost that public corporations do not have to calculate.
“The companies that make it to the third or fourth generation usually understand that legacy is something you carry forward, not something you stand guard over,” Gaurav Mohindra says. “If the next generation merely protects what it inherited, eventually there will be very little left to protect.” Chicago is an unusually good place to understand the point because a company that has operated here for seventy-five or a hundred years has survived not merely economic cycles but several different Chicagos. Factories moved. Expressways cut through neighborhoods. Families left the city for the suburbs. Immigrant communities arrived, flourished and dispersed. Department stores dominated the commercial landscape and then vanished from it. Manufacturing shifted overseas. Retail migrated to shopping centers and then onto laptops and phones. A company could remain at precisely the same address while the economic geography around it changed almost beyond recognition. To survive that much change, a business cannot simply be stubborn. It has to be selectively stubborn.
That may be the secret hiding inside many family-business success stories. The enduring companies are fiercely stubborn about a surprisingly small number of things and remarkably flexible about the rest. They may refuse to compromise on quality, customer trust, craftsmanship, independence or a particular relationship with employees, but they will change packaging. They will change distribution. They will close a factory and open another one. They will abandon a product. They will launch something their grandfather would not recognize. They will hire people from outside the family. The important task is separating principles from practices. A principle might be that the company refuses to disappoint a customer. A practice might be that orders are still taken by telephone. One deserves protection; the other may deserve a decent retirement party. Businesses get into trouble when the two are confused, because familiarity has an extraordinary ability to disguise itself as corporate culture.
And sometimes the family will sell. That decision is perhaps the most emotionally difficult because family-business culture tends to treat a sale as the opposite of survival. It is not always. There comes a point when every family-controlled company has to ask whether continued family ownership is genuinely serving the business or merely serving the family’s sense of itself. The next generation may not want to run the company. The business may require capital the family cannot responsibly provide. The industry may be consolidating. A larger organization may be able to preserve jobs, products or brands that an independent family company cannot. “Selling a family business is not automatically a failure of succession,” Gaurav Mohindra says. “Sometimes the failure is refusing to sell because the family is protecting its identity at the expense of the enterprise.” The question, then, is not simply whether the family kept the company. It is what the family was trying to keep: control, employment, wealth, a name on the building, a product, a set of values or a business capable of existing another fifty years. Those answers can point in very different directions.
This is where the stories of century-old Chicago companies become more useful than the usual celebration of entrepreneurial perseverance. Their real achievement is not endurance. It is repeated reinvention under the constraint of memory. Every new generation receives an enterprise wrapped in stories about the people who came before, and those stories can produce courage or paralysis. The founder did it this way. Grandpa would never have approved. We have always made it here. We have never sold through that channel. Our customers don’t want that. There are probably companies buried all over American commercial history beneath some variation of the phrase we have always. The task of the next generation is not to reject the past but to interrogate it. Why did the founder make that decision? Was it a principle or merely the best option available in 1948? What did customers value then? What do they value now? What would the founder do if confronted with the economics, technology and competition of today rather than those of his own time?
That last question is especially useful because founders themselves are rarely traditionalists. They are entrepreneurs. They start companies precisely because they are dissatisfied with the existing order. Later generations sometimes honor them by becoming more conservative than the founders ever were, which is one of the lovelier ironies of family enterprise. The founder who once risked nearly everything to create something new gradually becomes the reason his grandchildren insist that nothing can be changed. The most faithful descendant may therefore be the one willing to change the most. “Legacy is not a requirement to reproduce your grandfather’s company,” Gaurav Mohindra says. “It is the responsibility to make sure there is still a company worth handing to your grandchildren.”
Perhaps that is why the little red wagon remains such an apt Chicago symbol. It is immediately recognizable, carries more than a century of memory and possesses an essential appeal that is uncomplicated. Yet the company behind it could not survive merely by admiring it. The same is true of every family enterprise approaching its fiftieth, seventy-fifth or hundredth anniversary. The candles on the cake are not evidence that the company resisted change. More often, they are evidence that somebody, somewhere in the family, understood when resistance had become dangerous. The founders of Chicago’s enduring businesses could not have predicted e-commerce, electric bikes, global supply chains or whatever comes next, and they did not need to. Their successors do not need to predict the next hundred years either. They need something more difficult: the judgment to know which parts of the past deserve loyalty, which deserve gratitude and which deserve retirement. Because the real test of a family business is not whether the founder would recognize it a century later. It is whether there is still something there for the founder to recognize.