The Long Game

Revere is a gritty blue-collar town, and Kelly’s Roast Beef sums up the city’s lunch-bucket ethos with its “three-way” sandwich, a whopping pile of sliced beef on a butter-grilled bun with mayo, cheese, barbecue sauce, and onion rings. A beachfront fixture, Kelly’s had been serving this artery-clogging delight for over a quarter century when the 18-year-old Dan Riccio landed a job there in 1980.

Newly graduated from Revere High School, Riccio was at loose ends. He’d been a sharp student, but no one in his family had ever attended college—his father was a cab driver, his mother a homemaker—and come graduation day, he hadn’t even bothered to look into the option. “Imagine that,” he marvels. “I was almost valedictorian, and I didn’t apply to any colleges!”

Uncertain what to do, he spent a few months working at nearby Boston Logan International Airport, loading meals onto planes, then landed at Kelly’s, making those monster sandwiches. On crowded nights when the restaurant’s one register got overwhelmed, Riccio would add up orders and figure the tax, all in his head. Along with honing his math skills, his gig at Kelly’s brought him to a realization: He didn’t want to do odd jobs for the rest of his life. “I knew I had to get serious about education,” he recalls. “So, I asked a bunch of people for college recommendations.”

One came from a cousin who was a student at UMass—an engineering student. Visiting, Riccio fell in love with the campus and the town and decided to apply. It was the only school he applied to.

“I got admitted,” he says with a shrug. “And the rest is history.”

The video shoot concludes after stops at Riccio’s old high school and his boyhood street, its ramshackle multifamily houses stooped beneath a maze of power lines. From there, it’s a short drive up the North Shore to Marblehead, where he now lives with his wife, Diane, in an enclave of glossy homes perched on a bluff over the ocean. Riccio comes off as uninterested in the trappings of wealth, even dismissive. “I’m a Revere kid,” he says. “I live here because I’m loaded.” His house is sparsely furnished and decorated, almost spartan—Riccio dislikes clutter—and the main point of interest for him when he looks out his living room is not the spectacular terrace with infinity-edge pool, but the adjacent property where he thought about building a tennis court to accommodate a lifelong passion.

“It was 20 feet too short,” he says.

You can learn a lot about someone from how they play a sport, and I ask Riccio to describe himself as a tennis player. “First of all, I'm very competitive,” he says. “And I know that the longer that I’m out there, the better my chances are to win.” His strategy is to engineer longer rallies—15 shots or more—where he can prevail through persistence and minimizing mistakes. “I learned early on in tennis that winning a point by somebody else’s error is equal to hitting a winner yourself. Even at the pro level, more points are won on unforced errors than on winners.”

To Steve Jobs’s obsession with aesthetic perfection, Riccio added his own obsession with engineering.

Riccio’s long career in tech was driven by these same principles. Thrive on competition. Eliminate unforced errors. Play the long game. And bring your intensity. Riccio has plenty of that. However hesitant he may be in discussing his personal life, when the topic shifts to Apple and the blockbuster projects he headed there, he speaks with a hard-charging, raucous enthusiasm. Spend a few hours talking with him about his career, and you can’t help but be caught up in the excitement of it—the drama of high-stakes product design and development, conducted in circumstances of maximum pressure, that was his life at Apple.

He arrived in 1998, shortly after founder Steve Jobs returned to the company following a 12-year hiatus. Jobs returned with a mission to revive Apple, which was struggling at the time, and Riccio was put in charge of a 35-person product design team, tasked with supporting what he calls “Steve’s ultimate goal for the company—to design insanely great products for our customers that can improve their lives and uplift humanity.” He quickly decided that Apple’s creative young industrial design team was being “stymied” by its engineers, mid-career employees who lacked the risk-taking vision Steve Jobs wanted to implement.

Riccio took quick action, firing 90 percent of the team and rebuilding it from scratch. He had to make these drastic personnel changes even as he oversaw new product development and helped manage ongoing production of what was then Apple’s lead product, the iMac. It was a hectic time in his life. “I was building the engine while driving 60 miles an hour—developing one product and then the next product and the next, by hook and by crook, including me personally having to get on a plane and solve a problem.” When engineers on the iBook laptop were having trouble with the interface between its polycarbonate shell and rubber molding, Riccio flew to Taiwan to address the issue. He ended up staying five weeks. “I was manning the damn molding machine!” he recalls. “Basically, I had to put a cape on to get that done. If I hadn’t, that product would not have shipped.”

“UMass has come a long way, but I firmly believe in my heart of hearts that its best days lie ahead.”

Such emergency actions were not sustainable—either for him personally or for Apple. Something had to change. “When I joined Apple, we had only four products. How to build up that product line and then take all of it up to a million a day? I had to come up with a different process.” A process that would enable Apple to stop surviving paycheck to paycheck, as it were, and play the long game instead.

Riccio ticks off the improvements he instituted. Hiring in-house engineers instead of relying on consultants or equipment manufacturers. Basing product development at Apple’s home in California instead of decentralizing it in far-flung places. Having more time upfront in the design process, using computer-aided tools to “wring a design out” before actually building it. Undertaking several rounds of low-volume prototypes to test a product’s viability before scaling it up. Budgeting more for failure analysis when something did go wrong. And, finally, ensuring that tooling and manufacturing lines were sufficient to turn out products on a massive scale.

To Steve Jobs’s obsession with aesthetic perfection, Riccio added his own obsession with engineering, intent upon products “as elegant on the inside as they are on the outside,” as he likes to say. In the process—or rather, through the process he inaugurated—he helped create the modern Apple. Consider the list of products that would roll out during his tenure: iPhone, iPad, iPod, Apple TV, HomePod, AirPods, Apple Watch, Apple Vision Pro. It remains an astonishing accomplishment. “Every innovation Dan has helped Apple bring to life has made us a better and more innovative company,” Tim Cook said in 2021.

Riccio’s quarter century at Apple witnessed its growth from a maverick start-up to the colossus that sits astride today’s tech world. “The bottom line is that my team and I developed all of it,” he says. “We built the franchise that is Apple today. It’s one of the things I’m most proud of.”

Last October, two weeks before announcing his retirement, Riccio gave a talk at MIT’s Graduate Engineering Leadership Program, which he helped fund with a gift of $10 million back in 2022. When the moderator asked him to enumerate skills that can boost students’ effectiveness as future engineering leaders, Riccio laughed. “How much time do we have?” he joked. Some of the skills on his list were standard graduation speech fare, like curiosity and risk-taking. But others were less obvious, including an unlikely mantra he urged upon the students: “Paranoia can be your best friend.”

Riccio clarifies the concept for me, explaining that while optimism is crucial to envisioning an ambitious new product, when it comes to executing it, you need a process that’s “front-loaded with rigor.” That rigor includes figuring out what can go wrong with a product before you build it and ship it to customers. And that’s where paranoia comes in. “When you have paranoia, you tend to fixate on something at a very, very deep level,” he explains. “You’re looking around the corner to spot things that can bite you in the ass.”

As one instance where that paranoid instinct saved him—and Apple—from being bitten, he cites the first iPhone, back in the mid-2000s. The Apple design team had developed a prototype and was trying it out by using it themselves—a practice Riccio refers to, approvingly, as “eating your own dog food”—when they discovered a flaw. “Originally, it had plastic as its top layer. We were walking around with these, and Steve saw that he had had it in his pocket with his car keys, and he says, ‘It’s all scratched, what the fuck?!’” They spent the next five months developing a glass surface.

I ask whether he thinks another company might have just put the phone out there as is. Riccio cackles. “They all did! They shipped plastic—put a hard coat on it and called it a day!” For those other companies, he says, such a product defect might result in a few pissed-off customers. “But for Apple? If we had something like that, it'd be the front page of The Wall Street Journal.” The danger is manageable with software, he adds, where you can issue a patch. “But if you get a fuck-up in hardware, it’s a product recall. That’s a potential irreparable black eye, with implications for the finances of a company. So, if you're dealing in the hardware domain for Apple, how can you not be paranoid and still have a job for 25 years? You have to be paranoid!”

The problem, he continues, is that when you make paranoia your best friend, it can be hard to shut the friend down. Interestingly, one branch of Riccio’s philanthropy grew directly from this challenge. Some years back, he experienced persistent muscle twitches after running. The cause turned out to be nothing more sinister than insufficient hydration, but for a time, he feared he might have amyotrophic lateral sclerosis (ALS). This worry dovetailed with his wife Diane’s concern about a family history of Alzheimer’s, and the result was the couple’s first large benefaction, a $15 million gift to UMass Chan Medical School, a leading research center for ALS and other neurodegenerative disorders. “My philanthropic work with ALS stems from paranoia that transferred from my professional life to my personal life,” Riccio says. “Paranoia that I could not turn off.”

Dr. Robert H. Brown Jr., chair of neurosciences at UMass Chan, calls the impact of the Riccio funds “spectacular and transformative” in multiple areas, from hiring researchers who target particular categories of therapy to underwriting expensive animal testing and boosting cutting-edge genetic work. Regarding Riccio’s personal role, Brown cites a meeting when he and colleagues updated Riccio on their work. “We gave him our fancy presentation, and he appreciated it. But then he asked key questions about using new technology, like AI, to accelerate our research programs. That was two years ago, and we really hadn’t thought deeply enough about it. Dan put us on the track of thinking in a forward-looking way. I think he's visionary.”

In his retirement, Riccio wants to continue his philanthropy, supporting the rising generation of engineers and product designers by sharing the benefits of his career wisdom—and wealth. The huge gift to UMass—the largest the university has ever received—reflects Riccio’s gratitude for its formative role in his life. He credits his time in Amherst with teaching him a work ethic. In high school, he’d been able to skate by on his smarts with little effort. That didn’t work at UMass, and after a wayward first year, his academic status was precarious. A sophomore-year roommate helped turn him around. The roommate was a straight-A student, and when Riccio asked about the key to his success, his advice was simple: Go to the library every day. “He himself went every day for five hours,” Riccio recalls. “From 4 o'clock in the afternoon to 9 o'clock at night, he'd be in the library.” Riccio started going with him. “And guess what happened? On a dime, I went from a 2.0 to a 4.0.”

The look back at how UMass transformed a brainy but underprepared teenager from Revere drives Riccio’s vision of what his $50 million gift will do—and for whom. “I'm deeply passionate about kids who come from nothing, who work their way up through the public school system and public universities,” he says. Along with funding student scholarships, he’s eager to bolster and extend engineering at UMass on several fronts. Helping the engineering school incorporate product design into its curriculum. Funding lectures, courses, and internships in tech leadership. And focusing on the intersection between technology and health. It’s an area he was beginning to zero in on toward the end of his time at Apple via products like Apple Vision Pro, iPhone, and Apple Watch.

“I've only scratched the surface of what this can be, but I think there's a huge opportunity,” Riccio says. “Not just at UMass Amherst engineering school, but also its sister college at UMass Chan. Whether it’s sensors, generative AI, nanotechnologies, wearables, and eventually implantable devices and more, there's a lot that you can do in this space that can uplift humanity and improve the quality of people's lives.” Riccio is gung ho about building a wider road between Amherst and Worcester, he says. “I want to leverage the passion for this I had at Apple into developing a road map that goes out for 10 years of exciting and innovative stuff.”

His $50 million act of generosity is motivated by a high regard for public education and for UMass in particular. “I think it’s a great school,” he says, praising the leadership of Chancellor Javier Reyes and Sanjay Raman, dean of the College of Engineering. “It’s got world-class facilities. It's got some of the best instructors and professors in the world. If you're a kid who’s got a background in being scrappy and wants to get a great education that can prepare you for the future, UMass today is as competitive as any school out there. Does it get as much notoriety as the MITs of the world and the Stanfords and the Cal Polys? No.”

Riccio hopes to change that via an injection of personal and financial support. “UMass has come a long way,” he says. “But I firmly believe in my heart of hearts that its best days lie ahead.”

“I am deeply indebted to folks who paved the way for people like myself.”

At the end of a marathon day of interviews and videotaping, Riccio relaxes at his house, sitting back in a third-floor study with majestic Atlantic views. His current residence is fewer than a dozen miles from where he grew up, yet it’s worlds away. Riccio first encountered Marblehead when he was a kid and his father would drive him up from Revere, “just to check it out.” The two would clamber on the rocks and gape at the big houses.

I ask him what the adolescent Dan Riccio would have said if someone told him that his future self would be living in one of those houses, and he scoffs.

“’There’s no way in hell!’ There’s not one chance in a million that I thought I could ever be in a position to live here. I thought I’d be somebody who would live paycheck to paycheck, have a 30-year mortgage, and hopefully have enough where I could send my kids to school someday. That’s what I thought when I was a teenager.”

Does he think things could have gone that way? “I think I was remarkably fortunate to happen upon Apple when I did,” he says, after a long pause. “I got recruited because they wanted a mechanical engineer with high-volume PC manufacturing experience. … I got in on the ground floor of a company that had a guy named Steve Jobs running it, at the right time for me to build the teams that I did, develop the processes and deliver the products I did.”

In retirement, it’s a natural thing to contemplate one’s legacy. For Riccio, doing so leads quickly to the example of his Apple boss and mentor.

“What resonated from Steve is that we're part of a society where we have benefited greatly,” Riccio says. “If you're born in the U.S., in many ways, you won the lottery. I’ve been very, very lucky. And much like Steve, I am deeply indebted to folks who paved the way for people like myself to enjoy all the things that I can enjoy today. Steve always felt an obligation to give back, and I deeply agree. I honestly believe that if life's been good to you and you're in a situation where you can help in areas that you're passionate about, why wouldn't you? I'm deeply passionate about education, about what it's done to uplift me from my roots. I'm deeply passionate about what it has meant for me professionally.”

That passion, and his gratitude toward the institution that fostered it, have led Dan Riccio back to his alma mater, with a plan to help it play the long game. He intends to be part of the action. “It's not about just writing a check,” he says. “I also want to give UMass my time.” He grins.

“When I get involved with these things, I tend to be all in.”