#44 Gerald Schwartz

Net Worth: $1 B
Age: 78
Source: Finance
Industries: Finance & Investments

Gerald Schwartz runs Onex, one of Canada’s largest private equity firms. He got his start working with buyout legends Jerome Kohlberg, Henry Kravis and George Roberts at Bear Stearns in the 1970s. The Americans left to start KKR in 1976; Schwartz went home to Canada and cofounded the media company CanWest in 1977. In 1984 he started Onex, which has quietly outperformed many of the vaunted American private equity shops. Today the firm boasts $38 billion in assets, which Schwartz manages as chairman and CEO.

Net Worth: $1.1 B
Age: 57
Source: Steel
Industries: Manufacturing

Alan Zekelman owns a stake in his family’s steel business, Zekelman Industries. The $2.8 billion (revenues) company is one of North America’s largest steel pipe and tube makers. Alan and his brothers, fellow billionaires Barry Zekelman and Clayton Zekelman, split 100% ownership of Zekelman Industries. They sold the company to the Carlyle Group in 2006 for some $1.2 billion, but bought the business back in 2011. One of Zekelman Industries’ subsidiaries, Atlas Tube, is producing steel for the stretches of the Mexican border wall going up in Arizona.

Net Worth: $1.1 B
Age: 76
Source: Drugstores
Industries: Food & Beverage

Louie presides over grocery retailer H.Y. Louie and drug store chain London Drugs. His Vancouver-based holding company H.Y. Louie is the third-largest private firm in British Columbia, with an estimated $4.2 billion in revenue. His grandfather, Hok Yat Louie, immigrated to Vancouver from China in 1896 and worked as a farm laborer. Hok Yat eventually saved enough money to open a small general store in the city’s Chinatown in 1903. Louie joined the family business in 1972 and became president in 1987.

Net Worth: $1.1 B
Age: 63
Source: Software
Industries: Technology

Mark Leonard is chairman of Canadian tech company Constellation Software, which he founded in 1995. Constellation Software, also known as CSI, acquires, manages and builds software businesses. In 2019, the firm acquired nearly 100 tech companies. Constellation Software, also known as CSI, acquires, manages and builds software businesses. In 2018, the firm acquired 8 tech companies. After getting his MBA from the University of Western Ontario, Leonard worked in venture capital for 11 years.

Net Worth: $1.1 B
Age: 60
Source: Cirque du Soleil
Industries: Media & Entertainment

In 1984, Guy Laliberté, a former street performer, cofounded Cirque du Soleil, which would become one of the world’s biggest entertainment companies. His empire began with a show, funded by $1 million from the Canadian government, put on for the 450th anniversary of the discovery of Canada. The celebration went global, and the shows have been performed for more than 180 million spectators across more than 400 cities on six continents. He sold much of his 90% stake to U.S. private equity firm TPG Capital and Chinese investment group Fosun in 2015, but kept 10% of the company. In 2017, he founded Lune Rouge, which develops and invests in projects in arts, technology and entertainment. Laliberté was briefly held in custody in Tahiti for growing cannabis at his French Polynesian residence in November 2019.

Net Worth: $1.1 B
Age: 81
Source: Shoes
Industries: Fashion & Retail

Aldo Bensadoun is the founder of Canadian retailer ALDO, best known for its footwear and accessories. The son of a shoe merchant and grandson of a cobbler, Bensadoun was born in Morocco and spent most of his childhood in France. Upon moving to Montreal for college, he opened ALDO as a concession within a chain of popular fashion boutiques in 1972. His son, David, who is now the CEO, joined the company in 1996 and became the fourth generation of his family to work in the shoe business. ALDO pulled in an estimated $1.5 billion in sales in 2019 and has more than 3,000 stores across the world.

Net Worth: $1.3 B
Age: 68
Source: Finance & Investments
Industries: Finance & Investments

Stephen Smith is the founder, chairman and CEO of Canadian mortgage lender First National Financial. Smith launched the company in 1988, just four years after being personally bankrupt, and took it public in 2012. He also owns about half of Canada Guaranty Mortgage Insurance Company and a stake in publicly-traded Canadian bank Equitable Group. In 2018, he bought half of Walmart Canada Bank from Walmart and put up over $110 million to start the private equity fund Peloton. In 2015 he donated $50 million the Queens University, where the business school is named after him.

Net Worth: $1.3 B
Age: 77
Source: Telecom
Industries: Telecom

A dual-UK Canadian citizen, Terence (Terry) Matthews made his fortune with telecom firms Mitel and Newbridge Networks. In December 2018, he left his Chairman role at Mitel, the company he co-founded with Michael Cowpland, after it was acquired for $2 billion. In 1986, Matthews founded data networking business Newbridge Networks before selling it to Alcatel in 2000 for $7.1 billion. He claims to have funded or founded more than 100 companies, many through his Ottawa-based investment firm Wesley Clover. A resident of Canada, his UK property portfolio includes Celtic Manor Resort, which hosted the 2010 Ryder Cup and 2014 NATO Summit.

Net Worth: $1.3 B
Age: 79
Source: Real Estate, Private Equity
Industries: Finance & Investments

A South African native and trained accountant, Jack Cockwell is a famed dealmaker in Canada. From the 1970s through the early 1990s he built the Bronfmans’ Edper conglomerate, acquiring massive holdings in real estate, forestry and mining. Now known as Brookfield Asset Management, one of the world’s biggest money managers, he handed the reins to fellow billionaire Bruce Flatt in 2002. His wealth comes from a large holding in Brookfield shares, much of it in a partnership shared with other board directors and management. Cockwell is a member of Ryerson University’s board of governors and governor of the Royal Ontario Museum.

Net Worth: $1.4 B
Age: 51
Source: Steel
Industries: Manufacturing

Clayton Zekelman owns a stake in his family’s steel business, Zekelman Industries. The $2.8 billion (revenues) company is one of North America’s largest steel pipe and tube makers. Clayton and his brothers, fellow billionaires Barry Zekelman and Alan Zekelman, split 100% ownership of Zekelman Industries. They sold the company to the Carlyle Group in 2006 for some $1.2 billion, but bought the business back in 2011. One of Zekelman Industries’ subsidiaries, Atlas Tube, is producing steel for the stretches of the Mexican border wall going up in Arizona. He also owns two telecoms companies in Ontario.

#32 (tie) Pierre Karl Péladeau

Net Worth: $1.4 B
Age: 58
Source: Media
Industries: Media & Entertainment

The son of Quebecor’s founder, Pierre Karl Péladeau is the largest individual shareholder in the media company, which prints Le Journal de Montréal. Péladeau has spent 16 years as the company’s CEO–taking a three year break between 2014 and 2017. In 2015, he won and led the separatist Parti Québécois for nearly a year, before resigning in May 2016. In February 2017, he returned as CEO of a very healthy Quebecor, as shares rose 70% during his political stint.

Net Worth: $1.4 B
Age: 87
Source: Insurance, Investments
Industries: Finance & Investments

Hal Jackman and his family are the largest shareholders of E-L Financial Corporation, a Toronto investment and insurance holding company. His father, former Parliament member Harry Jackman, built a financial services empire, which Hal continued to expand over his decades at the helm. His son, Duncan, now runs the business as chief executive officer, president and chairman of E-L Financial. Jackman followed in his father’s footsteps into politics, serving as the 25th lieutenant governor of Ontario from 1991 to 1997.

Net Worth: $1.4 B
Age: 70
Source: Information Technology
Industries: Technology

Serge Godin is chairman of Canadian tech firm CGI Group, which he founded in 1976 at age 26. One of nine children, Godin started working for his father (who had just a fifth-grade education) at the family’s sawmill at age 12. He studied computer science and got an MBA from Quebec’s Université Laval, then worked in consulting before using $5,000 in savings to start CGI. Godin serves as chairman of the $9.3 billion (revenue) company; he was president and CEO until 2006. He has overseen more than 70 acquisitions, including the 1998 purchase of Bell Sygma, which nearly doubled the size of the company at the time.

Net Worth: $1.5 B
Age: 94
Source: Money Management
Industries: Finance & Investments

Stephen Jarislowsky made the bulk of his fortune at the helm of Jarislowsky Fraser, the investment management firm he founded in 1955. He stepped down as CEO in 2012 but remains chairman emeritus of the company and president of the Jarislowsky Foundation. Canadian bank Scotiabank bought Jarislowsky Fraser for about $750 million in stock and cash in April 2018. He owns a sizable art collection that is largely comprised of Canadian art, but also includes Chinese jade and French impressionism. His foundation has endowed over $220 million and has established 40 university chairs across Canada.

Net Worth: $1.5 B
Age: 63
Source: Retail
Industries: Fashion & Retail

Jacques D’Amours co-founded Canadian convenience store conglomerate Alimentation Couche-Tard in 1980. He retired as VP of administration in 2014, but remains on the company’s board and is its second-largest shareholder. Couche-Tard has ballooned by snatching up competitors, including Minnesota-based Holiday Stationstores for $1.6 billion in December 2017. The company now boasts annual sales of $59 billion and more than 14,000 owned or franchised stores worldwide.

Net Worth: $1.5 B
Age: 99
Source: Real Estate
Industries: Real Estate

One of Canada’s most prolific real estate investors, Marcel Adams founded Iberville Developments in 1958. Iberville owns and manages nearly 8 million square feet across some 100 shopping centers, office spaces, industrial properties and residential assets. Born in Romania under the last name “Abramovich,” Adams survived Holocaust labor camps during World War II before coming to Canada. He got his start working in the leather industry, but began investing in local real estate by the mid 1950s. His son, Sylvan Adams, a “Giving Pledge” signatory who now lives in Israel, has since taken over the business.

Net Worth: $1.7 B
Age: 41
Source: Uber
Industries: Technology

Uber chairman Garrett Camp cofounded the ride-hailing startup with Travis Kalanick in 2009. The Uber mobile phone app lets users request a ride and a driver-contractor is routed to pick them up — with Uber getting a cut of the fare. Camp owns about 4% of Uber, which listed its shares on the New York Stock Exchange on May 10, 2019. Before Uber, Garrett Camp founded web discovery tool StumbleUpon, which he sold to eBay in 2007 for $75 million.

Net Worth: $1.8 B
Age: 38
Source: e-commerce
Industries: Technology

Peter Szulczewski owns about 18% of e-commerce marketplace Wish, which connects shoppers with merchants who are mostly in China. In August 2019, Wish raised a reported $300 million round that valued the company at over $11 billion. Szulczewski grew up in an apartment block in Tarchomin, a district of Warsaw, then immigrated with his family to Canada at age 11. The computer science grad joined Google, where he helped build software that helps advertisers target people’s searches. He quit Google in 2009 to start his own software company, ContextLogic, which looked at a person’s browsing to predict their interests. In 2011 Szulczewski and college friend Danny Zhang re-launched the company as Wish.

Net Worth: $1.8 B
Age: 74
Source: Electronics Components
Industries: Technology

Canadian Robert Miller cofounded electronics distributor Future Electronics in 1968. In 1976, he bought out his partner for $500,000; now the Quebec-based company is one of the world’s largest electronics distributors. Future Electronics has a reported $5 billion in revenues from operations in 44 countries. Its products include adapter boards for LED screens, microcontrollers and LED lighting.

Net Worth: $1.8 B
Age: 69
Source: Homebuilding
Industries: Construction & Engineering

Peter Gilgan has built houses for some 90,000 homeowners since founding Mattamy Homes in 1978. Gilgan, who grew up as one of seven children in a middle class family, worked as an accountant before going into building. Inspired by the New Urbanism movement, he set out to construct suburban dwellings that broke from the bland and impersonal developments. Mattamy (named after the two oldest of his eight children, Matt and Amy) began designing and building planned communities from the ground up in 1986. Gilgan remains CEO of the $3 billion (revenues) business.

Net Worth: $1.9 B
Age: 54
Source: Money Management
Industries: Finance & Investments

Bruce Flatt is one of the biggest and best investors you’ve likely never heard of. Flatt runs Brookfield Asset Management, the $540 billion (assets) alternative manager with real estate, infrastructure and private equity operations. A Winnipeg native, he joined an accounting firm out of college, then took a job at Canadian conglomerate Brascan, which soon nearly collapsed. He helped revive Brascan through a series of savvy real estate deals and became CEO in 2002, refashioning the firm into Brookfield Asset Management. His winning deals include buying Olympia & York in 1996 and London’s Canary Wharf in 2015, and recapitalizing General Growth Properties in 2010.

Net Worth: $2 B
Age: 69
Source: Mutual Funds
Industries: Finance & Investments

Michael Lee-Chin made a fortune investing in financial companies like National Commercial Bank Jamaica and AIC Limited. The native of Jamaica acquired AIC in 1987, when it had less than $1 million in assets under management. Under Lee-Chin, the Canada-based wealth management and mutual fund business managed more than $10 billion in assets by 2002. But the firm was hit hard by the 2008 recession, and Lee-Chin sold AIC to Canadian financial services group Manulife in 2009 for an undisclosed price. He managed to hold onto a valuable 65% stake in National Commercial Bank Jamaica, which now makes up the majority of his wealth.

Net Worth: $2.1 B
Age: 65
Source: Real Estate
Industries: Real Estate

Carlo Fidani runs Orlando Corp., the Toronto-area real estate company he took over following his father’s death in 2000. The company has interests in construction and development, plus manages some 44 million square feet of industrial, office and commercial space. His grandfather founded the business as Fidani and Sons in 1948; Carlo took over in 2000 following his father’s death. Fidani was made a Member of the Order of Canada in September 2018, an honor recognizing his achievements and service to the country.

Net Worth: $2.2 B
Age: 53
Source: Steel
Industries: Manufacturing

Barry Zekelman took over his family’s steel business at age 19 and has since grown it into one of North America’s largest steel pipe and tube makers. He sold the company to the Carlyle Group in 2006 for some $1.2 billion, but continued to help run it. He and his family bought it back in 2011. Today Barry and his two brothers, Clayton and Alan Zekelman, split 100% ownership of the $2.8 billion (revenues) firm, now named Zekelman Industries. He made headlines when he was captured on a secret recording of a 2018 Trump donor dinner, bending the president’s ear about the steel business. One of Zekelman Industries’ subsidiaries, Atlas Tube, is producing steel for the stretches of the Mexican border wall going up in Arizona.

Net Worth: $2.2 B
Age: 58
Source: Real Estate
Industries: Real Estate

Mitchell Goldhar founded real estate firm SmartCentres in the early 1990s, then developed more than 265 shopping centers in the ensuing two decades. In May 2015, he sold most of SmartCentre’s assets to SmartREIT (formerly Calloway REIT), for about $880 million in shares, cash and assumed debt. Goldhar, who chairs SmartREIT, also owns various developments across Canada through his private company Penguin Investments. This includes a stake, along with SmartREIT, in the Vaughan Metropolitan Centre, a 100-acre master planned development north of Toronto. Goldhar owns Israeli soccer team Maccabi Tel Aviv FC, which won the Israeli club league in 2019. He plays squash, tennis and hockey.

Net Worth: $2.3 B
Age: 88
Source: Liquor
Industries: Food & Beverages

Charles Bronfman is long removed from the 2000 deal in which he and nephew Edgar Jr. sold their family’s Seagram spirits to Vivendi for $34 billion. His father Samuel Bronfman, a Russian immigrant to Canada, started a small distillery in 1924 and eventually bought out competitor Seagram. Since the sale, Charles, who once co-chaired Seagram, has turned toward philanthropy, authoring two books on the matter and signing The Giving Pledge. Bronfman has given away or pledged at least $350 million, mostly toward promotion of Canadian culture and the Jewish community’s connection to Israel. Bronfman’s son, Stephen, now runs Claridge, the Montreal-based private investment firm that Charles founded in 1987.

Net Worth: $2.4 B
Age: 92
Source: Drugstores
Industries: Fashion & Retail

The billionaire in the white lab coat, Jean Coutu founded the Canadian drugstore chain that bears his name. In October 2017 Coutu agreed to sell his publicly-traded company to supermarket giant Metro for $4.5 billion in cash and stock. Son of a pediatrician, he opened his first pharmacy in 1969, merging low prices on wide-ranging products with customer service and extended hours. Coutu, who was chief executive until 2002 and then again from 2005 to 2007, grew The Jean Coutu Group by acquiring many of his competitors. The company was once a leading shareholder of U.S. drug store operator Rite Aid but sold the last of its stake in 2013.

Net Worth: $2.5 B
Age: 90
Source: Oil
Industries: Energy

New Brunswick native Arthur Irving owns 100% of Irving Oil, which operates gas stations and oil refineries, through the Arthur Irving Family Trust. Arthur is a third-generation member of a Canadian dynasty. His grandfather, James Dergavel Irving, started the family business in the late 1800s. His dad Kenneth Colin (K.C) Irving added oil operations in 1920s; Arthur and his 2 brothers reportedly divided up the empire after KC’s death in 1992. Arthur’s brother James Irving, also a billionaire, took over a conglomerate that spans shipbuilding to forestry. A third Irving brother, John (known as Jack), headed the family’s construction operations and owned part of Irving Oil. He passed away in 2010. In 2018, The Arthur Irving Family Trust bought out Jack Irving family’s stake to assume 100% ownership of Irving Oil.

Net Worth: $2.5 B
Age: 79
Source: Hotels
Industries: Real Estate

Bob Gaglardi founded Northland Properties, which has interests in hotels, restaurants, sports, and construction. Gaglardi launched the business in 1963 with a $5,000 loan, opening his first Sandman Inn hotel four years later in British Columbia. He continued to put up Sandman Inns throughout Canada, plus expanded into real estate and restaurants. In 2011 he and his son, Tom, purchased the then-bankrupt Dallas Stars NHL team in a $240 million deal.

Net Worth: $2.6 B
Age: 60
Source: Fashion Investments
Industries: Fashion & Retail

Lawrence Stroll masterminded Michael Kors’ hugely successful IPO in 2011 with business partner Silas Chou, a Hong Kong fashion tycoon. The bulk of Stroll’s fortune comes from selling his shares in the American fashion brand; he sold the last of his stake in 2014. In Aug. 2018, Stroll led a group of investors to buy Formula One racing team Force India for £90 million plus assumption of £15 million in debt. After leading a $235.6 million (£182 million) investment in car company Aston Martin in early 2020, Stroll will become executive chairman. His 20-year-old son, Lance Stroll, one of the youngest members to compete in Formula One, is joining Force India in 2019. Stroll collects vintage Ferraris, one of which he purchased for a record-breaking $27.5 million in 2013.

Net Worth: $3 B
Age: 39
Source: e-commerce
Industries: Technology

Tobias Lutke founded and runs Shopify, the Canadian e-commerce firm that helps companies set up and run online stores. He owns 6.7% of Shopify, which went public in 2015. Businesses that use Shopify technology for online sales include Kylie Cosmetics and shoe retailers Rothy’s and Allbirds. Lutke grew up in Germany, where he learned to code by age 12 and left school at 16 to enter a computer programming apprenticeship. Shopify had over $1 billion in 2018 revenue; it has 1 million businesses as customers from 175 countries.

Net Worth: $3.1 B
Age: 71
Source: Retail
Industries: Fashion & Retail

Alain Bouchard cofounded convenience store conglomerate Alimentation Couche-Tard with a single Quebec shop in 1980. As executive chairman, Bouchard still oversees the $59.1 billion (sales) company, which boasts more than 14,000 owned or franchised stores worldwide. Bouchard, who grew the business rapidly by snatching up competitors, retired as president and CEO in September 2014. In 2017, Couche-Tard acquired Texas-based CST Brands for $4.4 billion (including debt) and Minnesota-based Holiday Stationstores for $1.6 billion. Couche-Tard is reportedly pursuing the Australian fuel retailer Caltex Australia and is eyeing the cannabis industry.

Net Worth: $3.2 B
Age: 63
Source: Lululemon
Industries: Fashion & Retail

Dennis “Chip” Wilson, the founder and former CEO of Lululemon, opened Lululemon’s first store in Vancouver in 2000. He took the firm public in 2007 but resigned as chairman in 2013 and removed himself from the business completely in 2015. In 2013, Wilson blamed Lululemon’s too-sheer pants on women’s body types, causing an uproar among fans. Although Wilson has no management role in Lululemon, he remains its biggest individual shareholder. Wilson is currently involved in Hold It All, which has businesses in apparel, real estate and private equity. His investments include stakes in Finnish sporting goods firm Amer Sports and Chinese sports apparel company Anta Sports.

Net Worth: $3.2 B
Age: 58
Source: Pharmacies
Industries: Diversified

Daryl Katz amassed a fortune in the pharmacy business, buying the Canadian rights to U.S. franchise Medicine Shoppe in 1991. A few years later he snatched up struggling Canadian drugstore chain Rexall, then expanded to the U.S. market. Katz, the son of a drug store owner, has since sold off all of his pharmacy operations, pivoting his Katz Group to real estate and entertainment. He has been co-developing a $2 billion, 25-acre complex in Edmonton’s downtown that will include offices, condos and retail, among others. Katz also owns his native city’s NHL team, the Edmonton Oilers.

Net Worth: $3.3 B
Source: Alcoholic Beverages
Industries: Food & Beverages

Anthony von Mandl created the ready-to-drink alcoholic beverages White Claw Hard Seltzer and Mike’s Hard Lemonade through his Mark Anthony Brands. von Mandl told Forbes his U.S. business is estimated to deliver close to $4 billion in revenue in 2020. He began his career in the Canadian wine business as an importer in the 1970s at age 22. He currently owns five wineries in Canada, including Mission Hill Winery in British Columbia’s Okanagan Valley. Through his company Mark Anthony Wine & Spirits, von Mandl is a leading figure of Canada’s alcohol importing and distribution sector.

9 Emanuele (Lino) Saputo & family

Net Worth: $3.8 B
Age: 83
Source: Cheese
Industries: Food & Beverages

Emanuele (Lino) Saputo chaired his family’s eponymous dairy company from 1969 until his August 2017 retirement. His son, Lino Jr., who has served as president and CEO since 2004, succeeded him as chairman. The elder Saputo’s father, Giuseppe, founded the business in 1954 with $500 and a bicycle for deliveries after immigrating to Canada from Sicily. Lino grew the company in the following decades, taking it public in 1997; today its products are sold in more than 40 countries. The family also has a stake in Major League Soccer’s Montreal Impact.

Net Worth: $4.3 B
Age: 91
Source: Diversified
Industries: Diversified

Jim Pattison oversees a sprawling group that operates 25 divisions including packaging, food and entertainment. Pattison’s first business was a GM dealership he bought in 1961. The Canadian billionaire also controls more than 40% of publicly-traded forest products company Canfor. His entertainment division includes Great Wolf Lodge, Guinness World Records and the Ripley’s Believe It Or Not! chain.

Net Worth: $4.5 B
Age: 92
Source: Diversified
Industries: Diversified

James Irving owns J.D. Irving, a conglomerate with more than two dozen companies in frozen foods, retail, shipbuilding, transportation and more. His timber and forestry operation, based in New Brunswick, has planted over a billion trees since 1957. His family’s fortune dates back to the 19th century, when his grandfather left Scotland and launched a general store and lumber and farming companies. His father added to the empire with oil operations in the 1920s; upon his 1992 death the three brothers James, Arthur and John split the assets. Irving Woodlands, a division of J.D. Irving, is the sixth-largest landowner in the U.S. with 1.25 million acres of land. Jim and Robert Irving, James Irving’s sons, are co-CEOs of the J. D. Irving empire, which also includes one of Canada’s biggest shipbuilders.

Net Worth: $4.9 B
Age: 46
Source: Online Gaming
Industries: Gambling & Casinos

Mark Scheinberg cofounded PokerStars with his father, Isai, and built it into the world’s biggest online poker company before cashing out in 2014. Scheinberg, who owned 75% of Rational Group at the time, pocketed more than $3 billion from the sale. He helped launch PokerStars in 2001, at age 28, and benefited tremendously from the poker boom that soon swept the U.S. and the rest of world. Scheinberg is investing some of the proceeds in Madrid, where he is helping restore seven historic buildings for commercial and residential use. In 2018, Scheinberg bought a stake in the Ritz-Carlton Yacht Collection from majority owner, private equity firm Oaktree Capital. He also owns the One Hotel in Toronto, Canada, which is set to open its doors in late 2020.

Net Worth: $5.1 B
Age: 61
Source: Real Estate
Industries: Real Estate

Huang Chulong chairs Galaxy Group, a privately held business based in the southern Chinese city of Shenzhen. Huang’s business interests span hotels, shopping malls, office leasing, parking-lot operation and real estate development.

Net Worth: $5.5 B
Age: 69
Source: Google
Industries: Technology

“Professor Billionaire” David Cheriton, who teaches at Stanford University, made his fortune thanks to an early investment in Google. Cheriton and Andreas von Bechtolsheim (also now a billionaire) each invested $100,000 in Google when it was just getting started. The pair cofounded 3 companies: Arista Networks (IPO in 2014), Granite Systems (sold to Cisco in 1996) and Kealia (sold to Sun Microsystems in 2004). Cheriton resigned from Arista’s board in March 2014 and has been unloading his stock; he still owns nearly 10% through a trust for his children.

Net Worth: $7 B
Age: 79
Source: Retail
Industries: Fashion & Retail

Galen Weston is chairman emeritus of George Weston, the Canadian food and retail giant founded by his grandfather in 1882. After successfully running grocery and retail stores in Ireland, his father handed him the reins to the struggling Loblaws supermarket chain in 1972. He turned the company around, by lopping off underperforming stores and redesigning the rest. His son, Galen Jr., now runs both George Weston Ltd. and Loblaws, which acquired Canadian drugstore chain Shoppers for about $12 billion in July 2013. Weston also owns a group of upscale retailers: Canada’s Holt Renfrew, Ireland’s Brown Thomas and UK department store Selfridges.

Net Worth: $10 B
Age: 56
Source: e-commerce
Industries: Technology

He is vice chairman and cofounder of Alibaba Group, and ranks as its second-largest individual shareholder after chairman Jack Ma. In 2018, he bought 49% of the Brooklyn Nets National Basketball Association team; the following year he purchased the remaining 51%. He holds two degrees from Yale University–an undergraduate degree in economics and East Asian studies and a law degree. Taiwan-born Tsai carries a Canadian passport.

Net Worth: $31.6 B
Age: 62
Source: Media
Industries: Media & Entertainment

David Thomson and his family control a media and publishing empire founded by his grandfather Roy Thomson. The family’s biggest holding: more than 320 million shares of Thomson Reuters, where Thomson serves as chairman. In 2018, Thomson Reuters announced it was selling a controlling stake in Refinitiv, a financial data provider, to Blackstone for $17 billion. The family also holds a stake in telecom giant Bell Canada and own the Toronto-based Globe and Mail newspaper.