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Over 160 years, the Richardson family has quietly built a $9-billion prairie powerhouse. Now they just have to figure out who will run it next

Hartley Richardson, president and CEO, James Richardson & Sons

Aidan Richardson was at the front of a raft full of teenage cousins when he saw a towering wave ahead. The whitewater guide in his boat yelled, "Paddle faster!" Nobody in the family had expected the Rouge River near Montebello, Quebec, to be so fierce that day in early July 2000.

Moments later, the boat was upside down. A second boatful of cousins saw the flip and gleefully overturned their raft as well. Thirteen-year-old Aidan and his kin—members of the sixth generation of one of Canada's wealthiest and most enduring business families—floated downriver, exhilarated.

It was the climax of an epochal three-day gathering at the stately Château Montebello resort for 40-plus descendants of James Richardson. The 19th-century Irish immigrant founded what is today Canada's largest independent, privately owned enterprise. Winnipeg-based James Richardson & Sons, Ltd. (JRSL) is a Prairie powerhouse: It handles more than a third of the country's grain trade, owns one of the top-performing Canadian mid-size oil and gas producers and co-owns one of Canada's largest independent wealth management firms. The family's charitable foundation is the top benefactor in its hometown, giving away $14 million last year.

While little known outside Canada's agricultural heartland, JRSL, with $10 billion plus in annual revenue, is among this country's 50 largest companies—bigger than Canadian Pacific Railway or National Bank of Canada. Its estimated value of between $7 billion and $9 billion makes JRSL's owners—the families of 11 of the founder's great-great-grandchildren—one of Canada's 10 wealthiest clans. "There's so much humility in the way they conduct themselves that I don't know if many people in Canada fully understand the extent of their enterprise and the impact they've had," says Mark Chipman, executive chair of True North Sports & Entertainment, co-owner of the Winnipeg Jets and a partner with JRSL in a $400-million development set to transform downtown Winnipeg.

Laying the groundwork to pass on this legacy to the young Richardsons began in earnest that weekend in Montebello. It was the first time the 11 first cousins who compose the fifth generation of the company's controlling shareholders—and collectively label themselves "the G5"—had gathered together all 28 of their children (there are now 29). While most of the G5s were raised in Winnipeg, their kids—the G6s—grew up all over the country. They were all 21 or younger, and some were meeting their extended family for the first time; everyone wore name tags and received a copy of the family tree, printed on a towel. Several G6s had little knowledge of the family's illustrious past.

The emphasis in Montebello was on fun and camaraderie, but the gathering's true purpose was to prepare the scions for their destiny. "That trip was a pivotal moment for us," says Aidan. One day, the youngsters would be fellow owners and stewards of a family enterprise older than Canada. To steer the company to continued success, they would have to maintain the familial social fabric that had held their parents' generation together. "People tend to think the success or failure of a family business transition relies on hard issues," such as the financial performance of the enterprise, says Olivier de Richoufftz, president of the Montreal-based Business Families Foundation. "The reality is that 80% of it is soft issues, like whether the siblings or the cousins like each other."

The odds are against them. There's an old saying that business families typically go "from shirt sleeves to shirt sleeves in three generations." Many dynasties that once dominated the Canadian corporate landscape—the Eatons, the Bronfmans, the Bassetts—have been chased into the history books following the takeovers or failures of their businesses. It's not just a Canadian phenomenon. According to the U.S. Family Business Institute, fewer than one in three family enterprises makes it to a second generation, and just 3% last into the fourth or beyond. Those that do are often well past their prime.

Carolyn Hursh is chair of the family company and Hartley Richardson is president and CEO. But not one member of the next generation has joined the firm.

Not so with James Richardson & Sons. Over the past quarter-century, the family's fifth generation—led by CEO Hartley Richardson—has navigated the business through its most prosperous course yet. Since Hartley took over from his father, George, in 1993, the company's value has increased 30-fold, thanks largely to a series of contrarian moves informed by the kind of long-term view few public-company CEOs, judged on quarterly results, can afford.

For decades, the family has kept a low profile as their company grew. But this year, as JRSL marks its 160th anniversary—making it 10 years older than Canada itself—the Richardsons allowed Report on Business magazine unprecedented access. In a series of interviews, 12 members of the notoriously discreet clan, along with several JRSL directors and executives, candidly reflected on their successes, their failures and their outlook. The Richardsons, it turns out, are quietly grappling with some major quandaries that will affect both the company's and the family's future.

The biggest issue is succession. Hartley is 63. In three years, he will become JRSL's second-longest-serving top executive, after the founder. He is the only G5 still employed in the business, and while he plans to stay at least five years, he doesn't intend to "stick around here just for the sake of sticking around." At this point, it's not evident who, if anyone, from the sixth generation could replace him—because none of them work for the family firm. Not one.

"I don't think, as a family, we know how to have the first person in my generation work for the family business," says G6-er Raif Richardson. Whether the next boss of JRSL—now a Fortune 500–size company—should even be a Richardson is an open question. Many, including Hartley, would like to see that, but, as he observes: "It's going to be challenging to please everybody."

You might expect an athletic, six-foot-four tycoon to make a big entrance. But Hartley Richardson appears in the sedate boardroom on the 30th floor of the Richardson Building in downtown Winnipeg almost as if out of thin air: entering silently, a modest, serious presence. True North's Mark Chipman describes him as a man who listens before he speaks, a trait evident in his quiet voice and halting, weary tone. It's as if Hartley feels the watchful gaze of his grandfather James Armstrong Richardson, eternally captured in a bronze statue in the corner, ensuring the family's unblemished reputation remains that way. Hartley fully expects the next generation's 29 kin to view the company as he does. "It's a privilege. It's a responsibility," he says. "What they do with it is up to them, but they've got to remember where it's come from."

If Hartley stepped down as CEO today, he'd leave his descendants a company significantly larger, more financially fortified and better positioned than it was when he took the helm 24 years ago. But over its long history, JRSL has faced numerous "inflection points," as Hartley calls them, where tough decisions had to be made, and there were lean periods in which its businesses struggled and the family received no dividends at all (as a private company, JRSL does not publicly disclose financial information). "Most of my generation have only witnessed successful years for the company," says Aidan, the eldest of Hartley's three children. "Dad always cautions that there were many difficult years in the past."

The JRSL story begins with Hartley's great-great-grandfather James Richardson, who arrived in Upper Canada in 1823 as a child and grew up a friend of future Prime Minister John A. Macdonald in Kingston. James started as a tailor before discovering he could make a decent profit by selling the sacks of grain he accepted as payment from his farmer customers. He became a grain merchant and founded the company in 1857. He supplied the Civil War–era American market and expanded to Winnipeg in 1880, three years before the CP Railway reached the city. Richardson's Pioneer grain elevators became staples of the Prairie landscape.

The founder's sons, George and Henry, grew the company, and his grandson James Armstrong Richardson moved its executive offices to Winnipeg shortly after assuming control in 1919. James Armstrong was the first Richardson to ascend to the top echelons of the country's business elite, serving on major corporate boards, expanding the company into the stock brokerage business and financing new technology ventures, including radio stations and the Technicolor motion-picture process commercialized by an engineer from Queen's University (where James A. later served as chancellor). He also founded one of Canada's first commercial airlines, Western Canadian Airways (Winnipeg's airport is named after him). Meanwhile, the family remained a fixture in grain, even as a major consolidation during the Depression felled many competitors and gave rise to farmer-owned co-operatives and a federal monopoly called the Canadian Wheat Board.

Following the death of James from a heart attack in 1939 at age 53, his wife, Muriel, took over. She was a trailblazer—the first woman to run a large Canadian corporation—and a pragmatic, commonsensical matriarch who defined the cultural mores of both family and company. "To whomsoever much is given, much is also required," she told her kin repeatedly. (Several Richardsons, who were obviously raised on the directive, quoted the line in their interviews.) During her 27-year tenure as president, JRSL introduced an employee pension and group insurance plan, ahead of most corporations, and established a charitable fund.

The mid-1960s marked the first challenging succession for the Richardsons. Muriel's two sons, James and George, who worked in different parts of the company, were unsure which of them would ultimately get the reins, says Carolyn Hursh, James's daughter and the current chair of JRSL. "My grandmother seemed to delay that [decision] for quite some time," says Hursh. She doesn't think "it was a peaceful co-existence" for the two brothers as they awaited the transition. In the end, the elder James succeeded Muriel as head of the company, but his tenure was brief: He quit after two years to run in the 1968 federal election, becoming a cabinet minister under Pierre Trudeau and leaving George to run the company. Entering politics was "something my dad really wanted to do, probably more than running the company," says Hursh. "It was a way of recognizing what's best for the big picture."

The next generational transition was not without its tensions. Three G5s applied to succeed George: Hartley, who had shovelled grain during summers in high school and later worked in the family's grain and real estate divisions; his cousin James, who had worked for the family's brokerage, and oil and gas interests; and James's brother, Royden, who had also worked for the brokerage. To make the process as objective as possible, the board—which by then had expanded to include former executives—asked an independent consultant to review the candidates and make a recommendation. In April 1993, Hartley was named CEO and cousin James became vice-president, remaining in the position until 2002. Not everyone was happy. All Hartley will say is that "whatever issues were there have been worked through."

Indeed, while the family has had its share of disagreements—"To say there aren't differences of personalities and jealousies would be naive," concedes Hartley—harmony is usually quickly restored. There have been no public spats, internecine lawsuits or formal moves to split the empire, nor have family members ever contested elections to the boards of directors of JRSL or its subsidiaries. "We don't hang our laundry out in public; we don't bring in consultants to advise us on every step," says Hursh. "We discuss amongst ourselves, and we resolve things."

Much of that approach traces back to a decision Hartley's generation reached during a retreat at Ontario's Minaki Lodge 30 years ago—the G5's version of Montebello. It was the first time the 11 had met to discuss their future responsi-bilities, and they committed to continuing the Richardson family's exclusive ownership of the company so they could pass it on to their kids. Orderly transition wasn't a divine right; it required a renewed commitment with every Richardson generation. That's why the job of JRSL chair comes with a dual responsibility: to oversee not only the board but also the family. In 2000, Hursh, a social worker and family peacemaker, was the overwhelming choice of her G5 peers to succeed her uncle George in that position. Asked which job is harder—running the company or running the family—Hartley replies: "On any given day, it's a coin toss."

It was not the best of times for JRSL when 38-year-old Hartley Richardson became CEO in 1993. Over the previous decade, the balance sheet had weakened and the company was overly diversified, with holdings in construction, transportation, printing, fertilizer, retail and real estate. The two largest operations were the investment brokerage, Richardson Greenshields, and the grain business—and neither was performing particularly well. Richardson Greenshields had suffered margin losses in 1987 and was put up for sale a year later, but the offers were tepid and JRSL pulled it off the block.

Hartley was well aware of the pressure. "We didn't want to be the generation that messed up," he says. His first order of business was to divest non-core assets.

Like his predecessors, Hartley was able to profit from the family firm's inherent advantage: With no outside shareholders to answer to, JRSL could take a long-term view. It could wait out market downturns and make contrarian moves, such as entering new businesses by paying fire-sale prices when everyone else was selling or consolidating existing ones, such as the grain business, when competitors were weak and vulnerable. Hartley also depended heavily on experienced industry executives drawn from outside family ranks to develop growth plans for JRSL's business units, and he let them reinvest profits in their businesses rather than pulling out cash to pay dividends to family. "He relies on management to understand the business, and once you have his confidence, he gives you a lot of flexibility to run your business," says Bryan Lankester, who heads JRSL's pipeline division, Tundra Energy Marketing Ltd.

Richardson Greenshields delivered the first major success of the Hartley era. Chuck Winograd, who headed the business, moved the brokerage to Toronto from Winnipeg and overhauled operations following the scrapped 1988 auction. Results improved and, in 1996, Royal Bank of Canada bought the unit for $480 million—equal then to roughly half the value of the entire JRSL. Hartley joined the bank's board, and Winograd became president of its capital markets business. The family received cash and millions of shares. The Richardsons held on to most of the shares and today own about $1 billion in Royal Bank stock.

Improving the grain business would take more time and resolve. Those vintage Pioneer elevators may have been picturesque, but they were small and outdated. In the early 1990s, Richardson was the fourth-largest player in a crowded grain-handling market. To lead the transformation, Hartley recruited Curt Vossen, a gregarious Saskatchewan-born agriculture executive who had spent 18 years with global giant Cargill. Vossen proceeded to pour capital into the business to keep up with modernizing rivals and replaced the company's 172 aging wood elevators with far fewer, but much larger, facilities. When back-to-back droughts hit the Prairies in the early 2000s, most grain merchants, constrained by their modernization campaigns, lost money. It was one of those tense inflection points for the Richardsons. "Everybody was scratching their heads and saying, 'Have we done the right thing? Have we overcommitted?'" Vossen recalls.

At a family shareholder gathering in Vancouver in 2002, some G5s suggested selling the grain division. Hartley dug in, pointing out that the grain business had broken even at the worst of times and that the recent investments had put the company in a strong position. He asked for more time, and the dissidents relented. Had Hartley given in, "it would have been a great tragedy for this company and for the family," says Vossen. The business soon bounced back and Richardson International, JRSL's grain handling subsidiary, emerged as a leading consolidator. The company lost a takeover battle for competitor Agricore but managed to buy $350 million worth of its facilities from victor Saskatchewan Wheat Pool to satisfy regulators. Then, when the Pool (renamed Viterra) sold out to global giant Glencore International, Richardson again stepped up, buying elevators, stakes in terminals and other assets from Glencore in 2013 for close to $1 billion. "They cherry-picked really good-quality modern locations" where the company had lacked a presence, says Kevin Klippenstein, CFO of rival Winnipeg grain merchant Parrish & Heimbecker. "That just made their business stronger."

Richardson is now the largest grain handler in Canada, with a roughly 35% share in Western Canada, and its expansion into food processing in 1999—another Hartley–Vossen move that was initially met with a cool reception from some G5s—has paid off. The company now owns a canola-processing business worth about $1 billion, producing such brands as Canola Harvest oil and Mirage margarine.

James Richardson & Sons has made similarly opportunistic—and lucrative—bets in energy. In the late 1990s, with oil drifting toward $11 a barrel, it bulked up its Tundra Oil and Gas unit, a small producer started by Hartley's cousin James. By the late 2000s, 25% of JRSL's total assets were in energy, up from 3% a decade earlier. Tundra made a major oil discovery in 2004 in Manitoba's southwest corner and continued investing in the business after oil prices tanked in 2014. "We've spent more on acquisitions [in the past three years] than we did in the previous 30 years," says Tundra CEO Ken Neufeld. Tundra is now the largest producer in Manitoba, and its offshoot, Tundra Energy Marketing, operates an extensive pipeline network in Manitoba and Saskatchewan whose assets were largely assembled through acquisitions.

The Richardson family's return to financial services last decade brought more mixed results. A foray into private equity in 2003 was a disappointment, and JRSL ended up refunding investors' money. More successful was a push into wealth management just as many independents began selling out to big institutions. Today, Richardson GMP Ltd., a co-venture with investment bank GMP Capital, manages close to $29 billion in assets. Less successful has been JRSL's investment in the stock of publicly traded GMP; its stake has lost more than $100 million on paper, as all resources-focused dealers have suffered recently. "It's been a challenging sector," says Hartley.

Despite some missteps, JRSL has grown and matured under Hartley's guidance. Its structure now looks less like that of a family business and more like a publicly traded conglomerate, with stand-alone enterprises that set their own courses for growth and have their own boards, comprising both independent directors and family members. What's missing among their ranks, however, are members of the next generation of Richardsons.

Thor Richardson, 29, has a lot in common with his father. Like Hartley, he is tall, handsome and carries himself with a down-to-earth demeanour that belies his privileged upbringing: He attended private St. John's-Ravenscourt School in Winnipeg, sailed at the elite Royal Lake of the Woods Yacht Club and studied law at the University of Cambridge, where he was captain of the hockey team. But like his parents' generation, he says,"we were raised to be very humble and stay below the radar." He reflects during a meeting at his office in Toronto's hip King and Spadina area, casually dressed in a striped shirt with rolled-up sleeves, jeans and moccasins. "I think we did a pretty decent job of just being normal."

Thor insists his father never pushed the family business on his three kids. "He's always said, 'Do what makes you happy, find fulfillment in whatever it is that you do,'" he says. For Thor, that was being an entrepreneur. As a teenager, he and a friend started a community newspaper, which they delivered by boat to fellow cottagers on Lake of the Woods. They even hauled away the cottagers' garbage for $3 a bag. Once, he stashed 20 trash bags in a shed on the family property without telling his parents, storing them up so he could take one big load to the dump. A bear had other plans and tore into the stockpile. Hartley was not pleased.

Had he been born into the previous generation, Thor would likely have entered the family business after graduation, along with several of his 28 siblings and cousins. But that option wasn't available because of a rule his father's generation adopted in the early 2000s: Anyone in the G6 who wanted to join JRSL had to first work for five years somewhere else. The general wisdom at the time was that family companies stood a better chance of developing future leaders if they let them prove themselves initially in a neutral setting.

So Thor joined a startup. While vacationing in the Bahamas in 2012, he met a wealthy developer who was in the process of co-founding a tequila company with George Clooney. Thor downed a shot, liked the product and wanted in. "I didn't know a thing," about the liquor business, he says. Despite that fact, he sought distribution rights for Canada. In 2013, with the support of his father and family advisers, he turned down offers from Bay Street law firms to join Casamigos Spirits. Soon, he was overseeing 22 territories from Toronto and was an equity partner. When Diageo PLC bought Casamigos this year for $1 billion (U.S.), Thor opted to stay on.

Although he will hit the five-year mark next summer, Thor is in no rush to move back to Winnipeg and join the family company. He plans to eventually settle down in his hometown and join JRSL, but right now his focus is Casamigos. "I wanted to [achieve something] for nobody but myself and prove that I was capable of being successful completely separate from the family."

Many of Thor's fellow G6s have similar stories. The 10 who spoke with us—future stewards of a vast fortune—come across as modest, thoughtful and well-mannered. They speak of being raised to be mindful of their place in society, devoid of any sense of entitlement—and to be discreet. Some didn't even realize they were wealthy until they attended private school. Ronald Richardson recalls one of his classmates at a tony prep school north of Toronto getting a Jet Ski as a present for barely passing a test. By contrast, Ronald and his two brothers had earned 25¢ as kids for doing chores, like emptying the dishwasher.

Another trait the millennial Richardsons share is a drive to succeed on their own terms. In that sense, they're not unique: A 2015 global survey by Ernst & Young of school-age kids in business families found that fewer than one in five saw themselves as potential successors, down 13% from three years earlier. Several Richardson G6s are entrepreneurs. Others are corporate executives or doctors or work in the arts. One is a chef. Most were encouraged by their parents to pursue their interests. Thor's older brother, Aidan, works for a Calgary alternative-energy startup; second-cousin Laurel Thomson is an executive with a film production and finance company. Carolyn Hursh's son Dan heads operations for the Winnipeg Jets' farm team. "There's an abundance of talent" in the younger generation, says family adviser Harvey Secter, chancellor of the University of Manitoba. "Over the next five to 10 years I think some of them are going to really blossom."

But will they bring that talent to the family enterprise? In the past two years, the Richardsons have been forced to rethink their well-intentioned five-year rule—not one G6 member has yet joined the company, even though the prohibition is now over for many. "In retrospect, maybe five years was too long," says Hursh. Many young Richardsons have moved well down their chosen career paths and planted roots—typically not in Winnipeg, nor in industries in which JRSL operates. "You can't parachute into the top," says Thor, who agrees with the rule in principle. "So you will inevitably have to take a haircut and come in lower and work your way up in a different industry, with a different set of contacts, most likely in a different city. Those are the realities of setting out that sort of policy."

The waiting period has created complications few Richardsons foresaw. Winnipeg-born Sprague Richardson (a nephew of Hursh), for example, was the one G6 who actually wanted to be a grain trader. He couldn't work for the family company—and none of the other family-owned western grain firms would hire him because they didn't want to train a competitor. The one company that was willing was Viterra, but when it entered into negotiations to sell assets to JRSL, Sprague decided to withdraw his application. Instead, he earned his commercial pilot's licence and became a crop-duster. Today, he owns his own company with 19 planes.

Another G6-er who tried to fully follow the five-year policy ran into a roadblock. Sprague's older brother Raif grew up in Winnipeg, thinking he might work for the family company after graduating from school. With that door closed because of the new rule, he got an MBA and worked in corporate development for a retailer. After seven years, he followed the established protocol of contacting the JRSL board's special advisory committee, which then put him in touch with the business heads who would help him find opportunities within the company.

It was a frustrating experience. Raif, now 34, had ad-vanced far enough in his career that a lateral transfer to an equivalent position at JRSL would have been difficult, given his lack of requisite knowledge and experience in its industries. In the end, he didn't find a position that made sense career-wise. "There were a lot of jobs shovelling grain," he says. "I was in my early 30s and had a family. It wasn't time to reset and go backwards." He ended up moving to Toronto, where he purchased a small company that helps automate distribution centres.

The board has responded to Raif's experience by creating a development program to make it easier for the young generation to find their way into the company. "It's still a work in progress, and we haven't had anybody test the new system," says Hursh. Beyond that, the sixth generation can get involved by attending JRSL shareholder meetings once they turn 21. A recently formed "observer director" program also allows them to join the boards of JRSL's operating companies for two years, where they can ask questions or make comments, but they can't vote.

It may not be enough. Hartley's father, George, used to say, "When you are born into this family you have grain dust in your blood." But the G6s recognize that may not be the case any more. One recently wrote to JRSL chair Hursh to express concern that his generation lacked the ingrained "hallway culture"—the intimate knowledge of the company picked up in casual interactions, the kind absorbed by their predecessors, whose lives revolved around the business. Reflecting on his cousins' successful careers, Raif sees a "missed opportunity" for JRSL. That same success could have happened within the family firm if they had "gone through the full experience of working in the business from shovelling grain all the way up," he says. "That type of industry is rooted in the very first job on the hierarchy. It's something we're missing at the moment."

While several G6s say they would consider throwing their hats in the ring to replace Hartley one day, some accept that the next CEO could come from outside the family. "At this point, the company has grown to a scale where I don't think a single one of us could take it on in the near future," says Colby Richardson, a nephew of the CEO. Hiring a non-Richardson as CEO would constitute a big cultural shift, as part of that role has always been ensuring the family's values were reflected in JRSL decisions. Yet other considerations may be more important. "We tend to think it's better to be a good owner than a bad manager," says de Richoufftz of the Business Families Foundation. "There are plenty of very talented mangers out there."

Whether or not their generation produces a CEO, the G6 will have to learn how to make decisions together as fellow shareholders. Those 21 and older have been meeting quarterly for years, but found they had little business to discuss—until fellow G6 Bryden Richardson suggested they give themselves a project. Now, they make formal recommendations to the Richardson Foundation on some of the charities it should support. That requires them to make decisions together, says Bryden, and "understand the complexities of trying to come to a consensus."

There are now 29 members of the latest Richardson generation,called the G6. They’re scattered around the country and some have found their attempt to join the firm frustrating

It's a good step, but the stakes are low. The G6 are friendly with one another, but it's unclear how they will fare when the 29 of them have consequential decisions to make as shareholders. In the years to come, for example, JRSL's focus in agriculture will likely shift from consolidating the Canadian grain trade to expanding into value-added food processing and international operations, following its first overseas purchase last June. The family is also bound to debate its ownership of energy assets, as at least two G6 members admit they aren't entirely comfortable with inheriting a fortune built in part on carbon-emitting fossil fuels. "There is certainly a dissonance," says Colby Richardson, who works for an electric bus manufacturer in Vancouver. Colby says he respects the energy industry's role in Canada's and the family's growth, but "I think it's time for a change, and I think that change has to happen sooner than most people may be ready for."

Most family businesses that survive for multiple generations end up "pruning the tree" of shareholders, typically by buying out descendants. It has happened before in the Richardson clan. When James Armstrong—part of the G3, in the family nomenclature—became president in 1919, he decided to consolidate. His brother, George, had planned to work alongside him but was killed in the First World War, and his other surviving sibling, a sister, had no children. So James A. bought out the shares of the founder's remaining descendants. The resulting payments strained JRSL's finances for years but returned ownership to a single family line. "Had that not happened, we could be 200 [owners] now," says Hursh, "and chances are we might not be here."

The family has multiplied to the point where it might be time for such a consolidation to take place again, but it wouldn't be easy. The G6s interviewed for this story say they are committed to remaining shareholders—a testament to their parents' efforts to promote family unity—and the value of the company has increased dramatically. Today, a meaningful consolidation would be "a very expensive proposition," says Hartley. And if just one or two of the current 11 other shareholder groups (the nine surviving G5s, plus the family holding companies of two cousins who died unexpectedly four years ago) were to sell, it wouldn't really change the dynamics around the table.

But at some point, things will get unwieldy. James Armstrong and Muriel Richardson had four children, who in turn had 12 G5 offspring (one of whom died before having children). There are 29 in the next generation, and there are already seven G7s. Family members estimate this newest generation could swell to more than 60 people. Yet there will only be so many positions in the company for family, particularly if meritocracy is maintained. The number of board seats has also been limited since JRSL adopted governance standards that call for inclusion of outside directors. Younger Richardsons with smaller stakes and no position in the company or on its boards may well be tempted to cash in what would still be a considerable fortune.

Separating the assets from the birthright, the family pride and the legacy has been a struggle. Years ago, JRSL's independent directors advised the family that the company needed a share buyback plan, whereby JRSL could buy and cancel shares from family shareholders who wanted out. So the company reluctantly established a buyback policy, and each year it would declare the number of family shares it would purchase. But, says Hursh, "for many years that number was zero"—the prospect of anyone cashing out was too much for the family to contend with. Outside directors made another push. "So then we picked a number [of shares]," she says. Still, nobody sold.

That finally changed about two years ago, when one G5 member—nobody will reveal who—tendered some shares. It caught many relatives off guard. "We had one sale. One single sale. And it was fairly traumatic," Hursh says. It meant one cousin had more liquidity than others but still owned a significant stake and remained an equal voice at the table, which didn't sit well with everyone. There were questions about loyalty to the family and responsibility to the company—after all, the cash came from JRSL's treasury. "It was gut-wrenching for some of us," says Hursh. The buyback program was suspended pending review. But the topic is bound to resurface. "You don't want shareholders to feel trapped," says G6 member Laurel Thomson, "and it would be foolish to think that when you're dealing with, say, 60-odd shareholders one day, that all of them will feel the same connection to the company."

Succession and shareholder consolidation are two of the biggest stresses on any family business, and the Richardsons don't seem to have either one figured out yet. "There's no manual," says Thor. "We're pretty much writing the rule book on this on our own." While the Richardsons' business longevity may be unusual in Canada, there are many examples of family companies in Europe and Asia that have lasted 20 or more generations and have managed both succession and consolidation successfully. The Richardsons have made the case that families can find leadership talent from within through at least five generations, managing to successfully expand their interests while keeping the clan together. Soon it will be the G6s' turn, and they are acutely aware of the stakes. "It's so tremendous to be part of that—you don't want to be the ones to screw it up," says Thor, echoing his father's fears during the earlier transition. "It's not lost on anybody…how much responsibility is coming."

Inside the Family Business

James Richardson & Sons is one of Canada's largest multinationals, with subsidiaries operating in four core sectors

Richardson International Ltd., Winnipeg
Canada's largest agribusiness owns grain elevators and port terminals in several cities, including Vancouver, and employs more than 2,600 people. Its divisions include:
* Richardson Pioneer Helps farmers grow, ship and sell grains and oilseeds, and provides crop planning, seed and fertilizer, financing and grain marketing
* Richardson Milling North America's largest oat miller, with five processing facilities located in Canada, the U.S. and the U.K.
* Richardson Oilseed One of the world's biggest canola oil processors with the capability to manufacture canola-based oils, margarines and shortenings

Tundra Oil & Gas (Winnipeg)
Manitoba's largest oil producer, it oversees the operation of more than 3,500 wells and facilities in southwestern Manitoba and southeastern Saskatchewan, producing about 27,000 barrels daily
Tundra Energy Marketing Ltd. (Calgary)
A mid-stream oil company that stores and transports oil to refiners in the North American market

Richardson Financial Group Ltd. (Winnipeg)
A major shareholder in:
* Richardson GMP A 30% stake in Canada's largest independent wealth management firm, located in Toronto, with more than $29 billion in client assets
* GMP Capital Inc. A 22.3% stake in the Toronto-based investment dealer serving corporate and institutional clients in Canada, the U.S., the U.K., Asia and the Bahamas
* Wynward Insurance Group A 100% stake in the Winnipeg-based insurer focused on commercial property with more than 34,000 policyholders across Canada

Richardson Centre Ltd. (Winnipeg)
A property owner and manager anchored by Winnipeg's landmark 34-storey Richardson Building office tower. Richardson Centre also manages the parent company's interest in True North Square, a $400-million mixed-used development in downtown Winnipeg.