Bernard Spain, 86, a successful retailer who founded a popular card shop, held the copyright for the iconic smiley face, and launched the Dollar Express chain that grew to more than 100 stores, died Wednesday of congestive heart failure at his home in Philadelphia.

A lifelong Philadelphia resident, Mr. Spain and his brother, Murray, sold 50 million buttons with the yellow smiley face after obtaining the copyright in 1971. Although the original symbol was designed by someone else, Mr. Spain added the slogan “Have a Happy Day” and copyrighted the revised mark, which he printed and sold on pins and countless other products, from posters to pajamas, according to Smithsonian Magazine. He later gave Walmart permission to use the mark so the retailer could resolve a legal challenge in Europe, his family said.

“He was always ahead of the curve,” said his daughter Dana Spain of Philadelphia. “He was always looking at what the appetite of the American consumer was looking for. Somehow he was always on that horizon. Always on that cutting edge.”

The smiley face may be Mr. Spain’s most recognizable success, but he also grew two retail chains that each operated in multiple states. He founded Spain’s Cards & Gifts in 1960, with the first store in the Cheltenham Shopping Center. The corner store concept sold cards, gifts, candy, and novelties — and grew to 30 locations in Pennsylvania and New Jersey. It became the largest Hallmark card chain on the East Coast, according to a family obituary.

Mr. Spain later founded Dollar Express in 1990 and, along with his brother, grew the company to 106 stores and $200 million in annual revenue, according to Temple’s Fox School of Business, where he graduated as a certified public accountant in 1956. At its peak, the chain employed 2,300 people before the Spains sold it and the gift shops to rival Dollar Tree for $300 million in 2000, Dana Spain said.

Launched near the dawn of the dollar store industry, Mr. Spain’s Dollar Express offered a wider breadth of products than its rivals, including groceries and seasonal items that cost more than a buck, said Seth Lehr, cofounder of the Philadelphia private equity firm LLR Partners and Mr. Spain’s investment banker at the time. Lehr helped the Spain brothers raise capital for the chain.

“They didn’t constrain themselves by only being $1,” he said. “They made their stores a weekly destination for shoppers because of consumables, not just one-off stuff.”

The relationship with Lehr came full circle when the Spain brothers became original investors in LLR Partners. Mr. Spain invested in several other Philadelphia-based companies, including the Cuba Libre restaurant chain, just as it was looking to expand outside the city. In addition to his money, Mr. Spain gave invaluable advice, usually over lunch or cocktails, where he would literally sketch business plans on the back of a napkin, Dana Spain said.

“As an investor, he was flexible and honestly in it for us rather than himself. He wanted us to succeed,” said Cuba Libre cofounder Barry Gutin. “I’d say that he quickly became family to us, and we hope to him as well that we were family. I genuinely loved the man, and that’s more than an investor.”

The son of Russian immigrants, Mr. Spain was born in Philadelphia on Nov. 6, 1934, to Harry and Mollie Spain. He grew up in the city’s Strawberry Mansion neighborhood, graduated from Central High School in 1952, and Temple four years later before serving in the Army, according to his family. He married Joan Feldman in February 1962, six months after meeting her, and they were married for nearly 59 years.

Mr. Spain was also a philanthropist, founding the Joan and Bernard Spain Foundation. The family championed many Philadelphia charities and institutions, including the National Museum of American Jewish History, the Hospital of the University of Pennsylvania, and the Philadelphia Orchestra. Central High School was especially important to him, and the Spains spearheaded a new library, auditorium, and lockers, among other renovations, according to his family.

Mr. Spain died at his home in Society Hill, Dana Spain said. In addition to his daughter Dana, Mr. Spain is survived by his wife, Joan, daughter Debbie Kelly, and two grandchildren, Brian and Megan Kelly.

Services will be held privately for immediate family. In lieu of flowers, donations can be sent to Central High School’s Bernard and Joan Spain Scholarship Fund, in care of AACHS, for Bernard Spain Class 198, Box 26580, Philadelphia, Pa. 19141; or online at https://bit.ly/35eUa6l.