The Not-So-Secret Life of Matty Gregg

Plenty of people dream of remaking their lives — Matty Gregg has actually done it. Multiple times, in fact. After running across the country to return home to New Hampshire, he plans what’s next.

Matty Gregg Photo by Kendal J. Bush

In 1994, when Matty Doris was 16 years old, his family moved out of the house he had spent his boyhood in. The house was in Nashua, a mile or two south of downtown, and Matty loved it. His dad, who died when Matty was nine, had built the house. Before going, Matty sought out a neighbor and asked him if he’d keep an eye on the old place. He said he wanted to be told if it ever came on the market. He said someday he was going to live there again.

By then Matty was a student at Phillips Exeter. He was a computer geek in an age when most kids were too shortsighted to realize that it would someday pay to have been a computer geek. The family’s first Apple computer had entered the house shortly after his dad died, and Matty fell in love with computing; it was a way of keeping sorrow at bay. He dreamt of one day working for the company behind the machine that had given him a sense of direction.

At Exeter, Matty’s adviser was the computer science chair. His passion for coding flourished. The dot-com boom was just starting then, and Matty had his adolescent fingertip squarely on its pulse. He understood that lean domain names would be worth something someday. When he discovered that could be had for $300, he called his mom — who ran the precursor to this magazine — to suggest that she buy it. As it turned out, a friend of hers had the same idea and bought it for her. “At the time was also available,” Matty remembers, with a look that says, “So it goes.”

Matty ended up at Exeter, one of the finest schools in the country, thanks to encouragement from the new father figure in his life, his stepfather, who also encouraged him and his brother to make the most of their summers off by spending seven weeks at camp. “It took me a while to forgive him for some of the pushes he gave me,” Matty says, “but looking back on it, I realize it was the right thing to do. It was a good time.” His stepfather was David Gregg, nephew of former governor of New Hampshire Hugh Gregg and first cousin to then-senator Judd Gregg. The Gregg family is the closest thing New Hampshire has to a dynasty. After finishing school, Matty asked his stepfather if he would adopt him. So Matty Doris became Matty Gregg.

The newly christened Matty Gregg went on to study political science at Holy Cross, where he continued to pursue computer science as a hobby. “If I was going to do computer science back then, it was C,” he says, referring to the programming language. “It was procedural. Object-oriented programming was something brand new, so I kind of looked at it and said, ‘Well, I can get a computer-science degree and maybe that will matter to employers, but in reality they’re not going to teach me the things I need to know, so I’m going to try something else.’ And, because of the family, political science just made sense.”

After graduating, Matty moved back to New Hampshire and took a job at New Hampshire Magazine, which had grown since the days when his mom began producing it in the basement of the Nashua house. The magazine had been acquired by the company that owned The Nashua Telegraph, and Matty was hired on as IT director for both publications, exhibiting for the first time a singular ability to parlay a hobby into a profession. Meanwhile, he and Rick Broussard, current editor of New Hampshire Magazine, founded the New Hampshire Theatre Awards, which continue to this day.

Matty runs past the Nashua house where he was raised and where this magazine first took root as Network Publications. Photo by Kendal J. Bush

Musical theatre had long appealed to Matty. In high school he was involved in drama, but what most excited him was enriching the theatrical experience through the use of multimedia and video technology. He dreamt of a production of his own someday.

In 2004, after considerable thought, he moved to New York City. He said he was going to write a musical about the tragedies of 9/11, and he began collecting stories by meeting with survivors and their loved ones. He composed a score and got most of the lyrics down. But in the end he was unable to produce the musical. He had signed nondisclosure agreements before conducting interviews, and some of the subjects ultimately had reservations about making their stories public. Fifteen years later, Matty still hopes that the passage of time will let him revive the project someday.

While in New York, he somehow landed a design job with an architectural firm. “I guess I interviewed well,” he says, when I ask how a political-science graduate with a computer hobby managed to swing a job that gave him a hand in overhauling Saks Fifth Avenue and creating the Top of the Rock observation deck at Rockefeller Center. From there he was offered a retail position in an Apple Store — which looked like a gateway to a dream. The problem was that the job was on Staten Island and required a two-and-a-half-hour commute. Matty seized the opportunity. Apple hired him as what it called a “creative,” and a creative is what Apple got. “It was the time when the video iPod had just come out,” he recalls. “I remember it as a nice, creative time. Traveling on the ferry I was able to come up with presentations and code systems that might actually be useful for Apple as a whole, as a retail organization.”

Matty was eventually promoted to the Fifth Avenue Apple Store when it opened. “It’s the only 24-hour store in the fleet,” he says, “so one of the challenges was that they didn’t really have a system in place for a 24-hour store that was as effective as it could be. So I was basically creating systems as supplements to the ones that we had to find ways to improve things.”

When somebody at corporate headquarters noticed his work, they offered him a job in California. In 2007, Matty was off to Silicon Valley for the fulfillment of another dream. For the next 12 years at Apple, he worked variously as a video producer, a coder, senior manager for retail technology, and finally senior manager for Apple Pay global expansion.

Matty has loved running ever since he was a kid, when his biological father showed him “The Terry Fox Story,” a 1983 film about the young Canadian athlete who lost a leg to osteosarcoma, an aggressive bone cancer that often begins at the knee. On a prosthetic right leg, Fox set out running across Canada, chalking up a marathon a day, to raise money for cancer research. After 3,339 miles the cancer reached his lungs and he could no longer breathe. He was forced to leave the road, and several months later he died at 22. Terry Fox Runs still take place every year around the world and have become the world’s largest one-day annual fundraiser for cancer research.

When I met Matty at his old house — now his new house — in November, he still emitted some of that aura that people accumulate when they’ve been out on the trail doing exceptional things for a long time. Or maybe he glowed because he was finally home.

In California Matty became passionate about obstacle-course running and ultramarathons. Fox had shown him that he could use his personal hobby as a way of raising money to help others. As he put hundreds of punishing off-road miles behind him, sometimes running for 24 hours at a time, he was able to simultaneously direct hundreds of thousands of dollars to the aid of organizations such as the Wounded Warrior Project, Beyond the 11th and St. Baldrick’s Foundation.

But in 2016 the beating he was giving his body caught up with him. He began to experience pain he had never imagined possible and lost feeling and motor function in his left arm. He found himself reduced to tears by nerve pain as he lay in bed for weeks. He suffered chronic headaches. Doctors admitted him to the hospital for emergency surgery to remove a disc from his neck and fuse together the surrounding bones. Lying in a neck brace watching a ceiling fan go round and round while he recovered set the wheels in his mind to turning.

Some people are basically the same person at 18 and 80. They don’t dream and they don’t evolve. They neither seek nor find. They ride a gentle breeze back and forth across life’s harbor, sailing on an even keel. They are what they are.

Anyone who wants to become something more must dream. But just dreaming is not enough.

James Thurber’s classic story, “The Secret Life of Walter Mitty,” is eloquent on the risks of dreaming. The subdued antihero, dragged around town by his wife on her tiresome errands, sporadically lapses into the most outlandish fantasies. One minute he is commander of a Navy hydroplane powering through an ocean storm, the next he’s a sought-after surgeon performing a rare and dangerous medical procedure. He is invariably summoned back to reality by his wife’s nagging. In the final scene of the story, Mrs. Mitty orders her husband to wait for her in the street while she visits one last shop. Walter Mitty stands against the wall, lights a cigarette, and suddenly imagines himself facing a firing squad. “To hell with the handkerchief,” he tells the executioner, and looks into the eyes of fate.

If you want to fulfill your dreams, you have to chase them. Otherwise you may wake up one day to realize you’re living in a nightmare.

But following dreams takes you down another road. Chances are that road will have lots of bumps and curves in it. Matty, long a chaser of dreams, found himself somewhere along that road in 2016, when he posted these thoughts to his blog:

“I am a 37-year-old man who is still ‘connecting dots’ of what makes me a happy human. I had a successful career at 23, gave it up to move to New York City to write a musical at 24, almost bankrupt at 25, married and beginning my journey at Apple at 26, stable at 30, divorced at 32, and starting all over again at 37, at a different place in my life. Roller. Coaster. Ride.”

There is one sure thing about roller coasters though: They always go in circles. They end where they began.

Working at Apple had once been a goal for Matty. Now it was an accomplishment. He was satisfied with the contributions he had made during his 12 years there. He felt like had played an important part in a revolution that had reshaped the world. At the entrance to Apple headquarters, a shred of Steve Jobs’ philosophy is lettered on the wall. After his surgery Matty posted the words to his blog: “If you do something and it turns out pretty good, then you should do something else wonderful, not dwell on it for too long. Just figure out what’s next.” Looking at the fan on the ceiling, Matty thought hard about what was next.

Matty jogs on Rodeo Beach in the Golden Gate National Recreation Area of Marin County at the beginning of his run.

He still had many dreams — ambitious dreams — but one of them had a deadline attached to it. Matty had known for a while that he would stop running by 40. It was too hard on his body. His recent injury seemed to prove the point. And so it was time he got serious about fulfilling a longstanding dream of emulating his childhood hero Terry Fox on his own turf: Matty would run across the United States. But the run, if he planned it right, could coincide with the fulfillment of other dreams. Matty is not the kind of guy to run across a continent just for the heck of it. He needed a reason to run. He needed a plan for what came after the run. And he needed a precise destination. Unsurprisingly, he had dreams to fulfill each of these needs. Now he just needed to fold those dreams together into plans and turn the plans into reality.

A run east from California fit perfectly with Matty’s ambition of someday seeking political office back home in New Hampshire. The ambition was always there. He had studied political science in college and then, well, he’s a Gregg. Now the news said Americans were as polarized as they had ever been, and it was painful for a public-spirited man like Matty to see. Greggs belonged to an old New England tradition of political moderation, but no one seemed interested in moderation anymore. Matty would use his run to get up-close with Americans all across the land to try to find out why they were so at odds.

Since fundraising had become an important facet of Matty’s identity, his run could also become the ultimate fundraiser. He made up his mind that any money raised would go to the Firefighter Cancer Support Network. His respect for firefighters and the dangers they face was born of the same admiration that had led him from New Hampshire to New York to write a musical about 9/11 back in 2004.

But there was still a last piece of the puzzle — an almost-forgotten one way off at the edge of the table, one that would make a particularly satisfying click when it popped into place. And when it did, it happened on its own — serendipitously — outside Matty’s grand plan, like some cosmic vindication of all his meticulous forethought.

It took 24 years, but in 2018 word finally arrived that the house Matty’s father built in Nashua was back on the market. The run was already planned to finish in New Hampshire by then. Matty jumped and made an offer. The offer was accepted on his 40th birthday.

Matty set out from Cupertino on November 6, 2018, the day of the midterm elections, which seemed to highlight the political meaning underlying the journey. It was a meaning he reinforced by insisting that he was running in the spirit of Alexis de Tocqueville, the Frenchman who traveled through the United States in 1831 to study American life in light of its professed political ideals. When he got home, Tocqueville wrote “Democracy in America,” which remains one of the most insightful studies ever made of American civic and political culture. Matty’s goal wasn’t quite the same, but he wanted to understand why people in the US were so at odds. He wanted to look for common ground so that he would know where to put his feet if he ever succeeded in becoming a leader of American people.

After a farewell lap around Apple Park, Matty turned south and ran and ran and ran. He went down the California coast and east across the desert. He zigzagged through the South, going down into Texas, then up into Tennessee, and then back down into Georgia. By the time he reached Concord last August, he had been running for 275 days and had covered 5,400 miles.

When I met Matty at his old house — now his new house — in November, he still emitted some of that aura that people accumulate when they’ve been out on the trail doing exceptional things for a long time. Or maybe he glowed because he was finally home. He’d moved in just three weeks earlier.

Matty poses with the complete family he “acquired” on his run: (from left) Ethan (holding Ash), wife-to-be Alicia, Emma (holding Cinder), Kaya the dog and Noah. Photo by Kendal J. Bush

He introduced me to his partner, Alicia Herndon, whom he had known through friends for several years before his run but grew close to while facing wintry conditions in Arizona and New Mexico. Matty says he felt cold and lonely then, and talking to Alicia on the phone every day made it easier for him go back out and run. They fell in love and are now a couple in Nashua, offering me cookies, one of which was shaped like the United States and decorated with a line of icing marking Matty’s path. Then the three of us sat in the living room to talk.

Matty is writing a book now. “It’s based on the run, but it’s not about the run,” he says, just as Tocqueville’s book based on his journey was not about his journey. He wants to call it “Democracy in America 2.” The book accepts the persistent validity of most of Tocqueville’s analysis and builds on it to say something about America today. “It can be read from both sides,” Matty explains. “There’s a red binder and a blue binder. You’ll be able to start from either side, but in the middle there’s a purple area. The purple area feeds the ideas into the middle. It basically says where the common ground is. That common ground is part of what built this country, and it’s what we build our freedoms upon.”

I ask him whether he’s more sympathetic to one side, expecting he’ll dodge my question, but he doesn’t. “The blue side is easier to talk about because I believe that it’s based more in fact than emotion. Solutions are more possible in the blue area. If you look at something through a blue lens, you’re more likely to have an outcome that’s beneficial for people in general, because — to use the issue of climate change as an example — climate change is real. You cannot deny that it is a problem right now. So you look through a blue lens to find a solution. If I look through a red lens and the answer is take everything down, deregulate everything, destroy any sort of government — it’s very difficult to come up with an overall solution for any problem, because the solution to that is ‘humanity will save itself’ — when in fact we know that hasn’t happened yet, and it certainly doesn’t look like we’re heading toward that anytime soon.”

That said, his experience at Apple showed him something positive on the red side. He remembers a colleague who had a side gig trying to develop a laser capable of converting carbon dioxide into oxygen. He thinks, citing climate change again, that the blue side is mistaken in its belief that emissions control is going to save us. “We’ve gone way past that,” Matty says. “What’s going to save us is ingenuity — some way of actually removing carbon from the atmosphere. So it’s this double-edged sword. It was my time at Apple, in the private sector, which contributed to innovation. We basically were like, there is a major problem here that we need to solve through something we’ve never done before. The flipside is that an overarching solution probably requires some sort of higher body to say, ‘Hey, this is how we’re going to do it.’”

Once we’re done talking about his book and his run, I ask Matty what else he’s been up to. He tells me he just returned from Las Vegas, where he’d been with his touring musical theatre company. He has created his own production of the comedy-horror rock musical “Evil Dead: The Musical.” The distinctive feature of his production is a massive video backdrop and floor — a 3-D model he generated — that enables him to move the set around the actors and give spectators an experience they won’t find anywhere else. “It’s just a fun night for people,” he says. “People spend more money to sit in the first few rows, where we splatter them with fake blood.” Tickets are selling well, and after Las Vegas the show was moving on to San Jose and Chicago.

At the end of his run, Matty poses with his proud parents, Patricia and David Gregg, at the New Hampshire Statehouse.

Matty’s charisma and charm were unfaltering as he told me all this. There seemed to be no question to which he did not have a thoughtful and enthusiastic answer.

“Is he always like this?” I asked Alicia, who laughed and shook her head.

“Yes! He’s like the White Queen in ‘Through the Looking-Glass’ — ‘Why, sometimes I’ve believed as many as six impossible things before breakfast.’ That is Matty Gregg’s life!”

The only difference is that Matty Gregg lives on this side of the looking glass, in Nashua, New Hampshire, where things happen the right way around — and where the impossible things he dreams before breakfast have become possible by lunchtime and by dinnertime are accomplished facts.

When Matty finally shows me to the front door, I notice it has a new coat of purple paint on the outside. I look back him knowingly and snicker. “Yeah,” Matty says, with a quiet smile, and thanks me for coming.

Categories: People