Dick Portillo opened a hot dog stand in Chicago with $1,100 and built it into a billion-dollar regional chain, Portillo’s. After cashing out in 2014, he bought back some stores and built a new real estate and restaurant empire—now, he sits back and collects the rent.
It’s been 11 years since Richard “Dick” Portillo sold Portillo’s, the restaurant chain offering up Chicago-style hot dogs and Italian beef sandwiches that he founded in 1963. Sitting in the living room of his 9,000-square-foot home in the Chicago suburbs—a short drive away from the location of the original Portillo’s he opened more than 60 years ago—the 85-year-old former Marine is feeling nostalgic.
“I’m sorry I sold. I didn’t owe 10 cents to anybody,” he says. But ultimately, he knew it was the right decision to make. “There were 24 private equity groups that were interested in buying Portillo’s. The timing was right.”
Portillo had spent more than five decades building the company from a single hot dog stand in a 6-by-12-foot trailer without running water into a regional chain so beloved that the city of Chicago officially declared April 5th—the day it was founded—as “Portillo’s Day.” By 2014, the company was bringing in about $300 million in revenues from 38 locations in four states. The chain had no debt and Portillo owned every single restaurant himself. He cashed out that July, pocketing nearly $1 billion from Boston-based private equity firm Berkshire Partners.
Suddenly he found himself with a lot of cash and not much to do. He negotiated soon after the sale to buy back the land and buildings of 20 Portillo’s restaurants and commissaries in Illinois and Arizona for more than $100 million, locking in 20-year leases at some of the chain’s highest-grossing locations. (The average Portillo’s brings in about $7.6 million, more than fast-growing giants such as Chick-fil-A and Raising Cane’s; Chicago area locations, where the brand is better-known, rake in an average $11 million.) He also stayed on as a consultant through 2021, earning $2 million a year.
He’s since reinvested the rest of his proceeds into dozens of different businesses including everything from strip malls in the Chicago suburbs and industrial properties in Indiana to Houston apartments and spec homes in Naples, Florida. He’s the majority owner of the Boathouse at Disney Springs, America’s third-highest-grossing independent restaurant with $47 million in revenues last year, and an investor in an iconic Chicago steakhouse. And he’s also bought four more Portillo locations, with plans to buy more. “This is some of the stuff I own,” he says, leafing through photographs of his properties across the country and rattling off his most successful businesses: “Not bad for a kid with no education.”
All that plus his portfolio of bonds, private equity and stocks plus his homes, jet and yacht (named Top Dog) has made Portillo richer than ever, worth more than $1 billion, based on Forbes’ estimates.
Still, even with this much success, he readily admits it’s a less exciting life than the days when he was building his first business. “Portillo’s was fun. A lot of work, my God, the hours and the sacrifices,” he recalls. “I’m sorry I sold, I was happier. I’m happy now, but it was more fun.”
Born in Chicago to a Greek immigrant mother and a Mexican immigrant father who worked in factories and sold insurance, Portillo grew up poor in a public housing project. He wasn’t a great student, and seven days after high school graduation in 1957 he enlisted in the Marines.
After two years at Camp Pendleton in California, he moved back to Chicago and married his high school sweetheart, Sharon. Then he got to work, toiling at junkyards and factories, driving trucks and unloading box cars, while Sharon worked as a waitress.
But with one child and another on the way, Portillo wanted to turn his life around. “Most of my parents’ arguments were about money, and I did not want to be poor,” he says. “I thought, ‘boy, that’s where I’m going with all these jobs.’ I wasn’t trained for anything.”
Noticing how many hot dog stands littered Chicago’s streets, he decided to set up his own—but in the suburbs, where there was much less competition. He opened his first stand in the suburb of Villa Park in 1963. Then 23 years old, he convinced his wife to pour their life savings of $1,100 (about $11,600 today) into the business, which he named “the Dog House.” His brother, Frank, put in an equal amount, but Portillo bought him out four months later.
Portillo knew nothing about restaurants or hot dogs so he stalked rival spots to figure out where they bought their meat, buns and condiments, and eventually the business started growing. Sales doubled each year, and by 1967 he moved to a brick-and-mortar building and renamed the business Portillo’s. (Another upgrade: he finally got a bathroom installed.)
He used every trick he could think of to beat his competitors. After opening the first drive-through location in 1983, he told his son Michael to buy walkie-talkies from Radio Shack so that one of them could take orders from customers waiting in line while the other got the kitchen to make their food. “I remember thinking, ‘that’s the stupidest idea I’ve ever heard in my life.’ And by God, if he wasn’t right. We saw immediate results,” says Michael, 65, who still works at Portillo’s today as the vice president of restaurant support.
Portillo also made the business as complex as possible by adding more menu items, seeing it as the best way for him to stand out from national fast-food chains. “I thought, ‘Portillo’s not only can compete with McDonald’s and Burger King, but beat the daylights out of [them].’ It’s not just hot dogs, it’s two kinds of chicken, two kinds of Polish sausage, burgers, salads,” he says. That also required relentlessly training his employees—a 1988 manual instructed them in minute detail on how to wash pots and talk to customers—many of whom stayed on to work for him for decades. “In the Marines, I learned the value of teamwork, organization and training,” he adds.
By 1988, Portillo was bringing in $20 million a year in sales. That same year Forbes profiled him as an “up & comer.” The article detailed how he decorated every Portillo’s location with antiques, giving each one a different theme ranging from a 1930s lunchroom to a 1950s diner. “These are things the average fast-food company wouldn’t do,” Portillo told Forbes at the time.
Forbes first profiled Portillo in 1988 when he was an ambitious 49-year-old with 11 restaurants in Illinois and big plans to expand to Japan. He abandoned the latter venture after three years but his business became a huge success regardless. The reason why: “I worked my behind off.”
Forbes; Photo by Gary Sigman/Black Star
Portillo’s expanded outside of Illinois for the first time in 2005, opening a restaurant in California. The company had started shipping nationwide five years earlier, and Portillo targeted cities where he knew there were a lot of customers who had moved there from Chicago. By 2013 he’d expanded to Indiana and Arizona, where a new restaurant in Scottsdale brought in $82,000 on opening day with hundreds of people waiting in line. “I opened up four units in one year without borrowing a dime, I paid cash,” he says. “So when we opened up, they went bananas. It was printing money.”
Portillo’s ability to keep growing sales—even as he kept the complex menu and moved beyond his home region of Chicago—caught the attention of outside investors like Berkshire Partners. “He created a restaurant concept that’s one of a kind in a very crowded field,” says Mike Miles, a director at Berkshire who serves on Portillo’s’ board and helped take the company public in 2021. “An average Portillo’s does as much delivery volume as a Domino’s. It does way more drive-through than a McDonald’s. [Portillo] was very purposeful in having menu variety that was appealing to different guests but not so difficult to execute that it couldn’t be done well.”
Since he sold, Portillo has applied the same approach to his investments. That means diversifying as much as possible, even within the same piece of real estate. “You never want to put all your eggs in one basket,” says Portillo, pointing to one of his suburban strip malls, where tenants include a car wash, a Mexican restaurant, a beauty shop and a FedEx. “There’s no one big major guy where if he closes you’re in trouble. That’s my safety net.”
Starting in 2014, he built up a portfolio of about 2,000 apartments in Texas, Florida, Georgia and Kentucky. Then the Covid-19 pandemic sent waves of people moving to the South, sending rents soaring across those states. Portillo sold most of the apartments as values rose between 2021 and 2024 but held on to 270 units in Houston, which are 97% occupied. In 2016 he also started buying up industrial real estate in Indianapolis, amassing nearly 4 million square feet and attracting tenants ranging from Amazon to FedEx as demand for warehouse space surged during the pandemic years.
It’s a successful playbook for entrepreneurs looking for a new mission after selling their life’s work. “He taught me to go out and pick the best real estate and build whatever’s relevant and flip it and sell it,” says fellow billionaire Jimmy John Liautaud, who sold his own sandwich chain Jimmy John’s a few years after Portillo between 2016 and 2019 and considers Portillo a mentor.
He’s also been prudent with his cash, keeping 63% invested in bonds, 22% in stocks and 15% in other investments including private equity. When he has taken risks, they’ve often turned out well: he invested $5 million in Uber in 2014—five years before it went public in 2019—a stake that’s now worth about $13 million.
Not that Portillo is that excited about any of it. “They’re all kind of boring,” he laughs. What he has found more fun lately is building homes in Naples, designing them from the ground up. “My hobby is building houses, decorating them. I had a lot of fun doing that.”
Those houses are also the investment he’s the least confident about. “Two or three years ago, Naples was one of the hottest real estate markets in the country. I put $54 million into these houses, only sold one of them so far. The rest of them, the market went down,” he says. “You want to buy one? I’ll give you a good deal.” David Hoffmann, a fellow billionaire who lives across the water from Portillo in Naples and has his own real estate empire in the area, is more bullish: “I’m a huge believer in the market. It’s the best place to live in America.”
Even as he complains about being bored, retirement has given Portillo the time to indulge his passions. A World War II buff, Portillo filmed a PBS documentary searching for the wreckage of Japanese Admiral Isoroku Yamamotu—the architect of the Pearl Harbor attack—on the Pacific island of Bougainville. He’s also an avid art collector with centuries-old Aztec, Chinese, Egyptian, Greek and Roman antiquities. And he’s given nearly $13 million to organizations including the Chicago Diabetes Foundation (his wife, Sharon, has type 1 diabetes), his old high school and the Wounded Warrior Battalion in Camp Pendleton.
As for the company he built and ran for 51 years, Portillo is more stoic. He doesn’t own any stock in Portillo’s and he doesn’t go to the restaurants much anymore. As it keeps expanding without him—the $711 million (2024 revenue) chain now has 94 locations in 10 states— he now sees the locations he owns for what they are: just another good investment.
“If they default or go under, I still have a good piece of property and I like being a landlord,” he says. “And there’s always somebody that’s looking for a great piece of property.”
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