In the bustling world of fast food and quick bites, few names resonate as strongly in Chicago as Dick Portillo. The man behind the iconic Portillo’s restaurant chain, known for its mouthwatering Chicago-style hot dogs and Italian beef sandwiches, has had quite the journey. After building his business from the ground up starting over sixty years ago, Portillo reflects on the bittersweet experience of selling his beloved empire nearly a decade ago.
Portillo, now an 85-year-old former Marine, recently shared his thoughts from the comfort of his sprawling 9,000-square-foot home in the Chicago suburbs. With nostalgia flooding back, he admits that he sometimes wishes he hadn’t sold the business. It’s not about debts or obligations; it’s about the joy and excitement he felt while running Portillo’s. At one point, 24 private equity groups were chomping at the bit to snag his successful creation, and he ultimately decided it was time to cash in. After all, he had spent more than fifty years turning a simple hot dog stand into a beloved regional chain, earning a special recognition from the city of Chicago with “Portillo’s Day” officially celebrated every April 5th.
In 2014, Portillo’s was pulling in a staggering $300 million in revenue across 38 locations in multiple states. With no debts to speak of, Portillo made a bold move and sold his business to Boston-based Burkshire Partners for nearly $1 billion. Suddenly, he found himself flush with cash and faced with a new chapter. Rather than kicking back and sipping piña coladas on a beach somewhere, he astutely negotiated to buy back the land and buildings of 20 of his restaurants, securing 20-year leases at some of the highest-grossing locations. These Portillo’s restaurants are not just surviving but thriving, racking up sales that rival even the best in the business. In fact, a typical Portillo’s location rakes in about $7.6 million annually, with Chicago-area hotspots pulling in an impressive $11 million.
After the sale, Portillo didn’t sit idly by; he put his money to good use. He diversified his investment portfolio, putting cash into everything from strip malls and industrial properties in Indiana to luxurious apartments in Houston and vacation homes in Naples, Florida. He’s even the majority owner of The Boat House at Disney Springs, which stands as America’s third highest-grossing independent restaurant. While investing in an iconic Chicago steakhouse and buying back more Portillo locations, he also took on a consulting role for a few years, raking in a cool $2 million annually. It’s safe to say this savvy businessman has proved time and again that he knows how to make smart moves.
Despite his financial success and vast empire of investments, Portillo acknowledges that life after the mega-deal isn’t quite as thrilling as the days of scraping together every last dime to create his beloved chain. He fondly remembers the hustle and bustle of building Portillo’s with its long hours and sacrifices, admitting that he misses the excitement. Growing up poor with immigrant parents in a tough Chicago neighborhood, he worked tirelessly after leaving high school to support his growing family. But driven by the desire to succeed, he took the plunge into the restaurant business, eventually creating a beloved institution that Chicagoans and beyond cherish.
While Dick Portillo has certainly moved on to new adventures and amassed a fortune, his heart remains tied to the hot dog stand that started it all. As he navigates his diverse portfolio of businesses and enjoys his lavish lifestyle, the lessons he learned in those early years continue to shape who he is today. After all, nostalgia may tug at his heartstrings, but the legacy he built ensures that Portillo’s will remain a cherished part of Chicago’s culinary landscape for generations to come.
