Halfway up Heartbreak Hill—the most famous incline along the route of the world’s most prestigious footrace—a local resident held a handwritten sign that said, “Go Mary Wittenberg!”

While many of her fellow runners overlooked that particular encouragement, more than a few marathoners knew exactly who Mary was. As the director of the world’s largest marathon, Wittenberg was arguably the most famous recreational runner on that course.

Sometime in the late morning on April 21, 2014, Wittenberg crested Heartbreak Hill, looking forward to the last 10 kilometers of the Boston Marathon. She crossed the finish line at 3:32:55, in the top third of the field, the seventy-seventh woman in her age group. She learned that her friend Meb Keflezighi—an elite runner she’d helped cultivate by inviting him repeatedly to run the New York City marathon, which he’d won in 2009—had crossed the line in 2:08:37 to win the race, the first American man to win Boston since 1983. She’d helped Keflezighi become simply Meb. So like thousands of others, Wittenberg needed only two words to capture the ecstasy and import of his victory that year in Boston: “Meb won.”

A few hours earlier, at the starting line in the hamlet of Hopkinton, where each April the 300-year-old town of about 15,000 residents teems with tens of thousands of runners, volunteers, and spectators, Keflezighi and Wittenberg stood, a few thousand people nervously waiting between them.

For the 118th time, runners gathered there for a 26.2 mile footrace to the heart of Boston, past stoic New Englanders sipping coffee, drunken and screaming college students, and Red Sox fans watching the annual Patriots Day late-morning baseball game at Fenway Park.

The Boston Marathon—just Boston to anyone in the marathon world—stands alone in the world of distance running, especially for amateurs. Because of its strict qualifying standards, only a small percentage of those who complete a marathon have a time good enough to make it to the starting line.

What pulsed through the streets in and around Boston that day wasn’t just an athletic marvel. It was also an economic juggernaut. The race’s organizers estimated that runners, their friends, and family pumped $181 million into the local economy. Obvious beneficiaries included Italian restaurants in Boston’s famed North End, where runners and their entourages flocked for Sunday night pre-race pasta dinners, lining the narrow, winding streets clad in sneakers and emitting nervous energy. Hotels across the city were sold out, with some runners making reservations months in advance (some within days of finishing the previous year’s race).

Each runner paid $175 just for the privilege of lining up in Hopkinton, quite literally the cost of entry; international racers paid $225. Tack on marathon merchandise, lodging, food, and tours of the city for families abandoned by their resting-their-legs runners and you start to get a sense that this is big business. By contrast, hosting the World Series in 2013 brought about $23 million to St. Louis; the All-Star Game the following year brought Minneapolis about $75 million. (As befits its status as the uber-event, the Super Bowl is worth about $500 million to its host city.)

The 53-year old Wittenberg, at the time of her first Boston run that year, was the CEO of New York Road Runners (NYRR), the largest nonprofit community running organization in the world. That perch made her one of the single most influential figures in the world of running, present and future. NYRR’s signature event is the New York City Marathon, the biggest marathon in the world. Throughout the year, the group puts on dozens of other races, including a popular half-marathon series with a race in each of New York’s five boroughs.

Her mission: Make it possible for people to “run for life,” a motto she adopted for her entire organization, which is headquartered in a sublet beehive of offices in midtown Manhattan, just a couple doors down from Carnegie Hall. (In a nod to the organization’s work, workspaces and offices are identified by race bibs with the occupant’s name instead of traditional nameplates.)

In 1970, 127 runners suited up to run the first New York Marathon—four consecutive loops of Central Park Drive, the paved road that circumnavigates New York’s iconic park (55 people finished). Thirty-five years later, in 2015, about 50,000 runners snaked from Staten Island to the finish line in Central Park, touching each of the five boroughs. It’s a massive, sprawling, annual autumn happening, bringing athletes from all over the world to test themselves on the largest stage in this particular sport.

That translates to massive economic power, mostly by virtue of bringing big-spending visitors to cities, often for weekends when the city is otherwise without a convention or other major event. Economic impact often totals tens of millions for a marathon host city, and into the hundreds of millions for the largest races. It starts with the entry fee, which effectively ensures an affluent field.

The New York marathon, arguably the best-known marathon due in part to its location and rich history, and the largest by number of runners (a record 50,530 in 2014), charges $255 for a non-New York Road Runners member (members, who aren’t guaranteed entry without completing a prescribed number of other NYRR races and volunteering for another, pay $216). Foreign-based runners pay $347. The marathon has to operate a lottery for entries, owing to the massive number of entries. The high fees clearly aren’t scaring anyone off.

That’s in part because of the race’s participants. The average annual income for a participant in the New York City Marathon is reportedly $130,000.¹ Put another way, that’s well north of double the median income of an American household (roughly $51,000).

An economist would point out that the price for the New York City Marathon (and many others) is inelastic. That is, demand doesn’t markedly change even when the price changes, in this case dramatically over a period of just a few years. (The nonmember rate was $196 in 2011. New York Road Runners increased it to $255 for the 2012 race, citing the need to pay more of its share of the traffic management costs.)²

New York’s marathon is credited with an economic impact of about $340 million, a figure from a 2010 study that was cited around the initial decision to hold the 2012 race, even after Superstorm Sandy ravaged the region. The storm depleted public resources and set up a situation where the footrace would divert men and women from cleaning up and piecing life back together for the region’s residents. The race was eventually canceled.

At least one writer has said the actual economic impact was less than half of that. Writing on Forbes.com, Patrick Rishe took issue with the figure, and made his own calculation of $144 million, including the runners and spectators.³ While significantly less, I’d still argue that’s a lot of money generated by a bunch of people running through the streets of New York while 2 million of their friends and family cheer them on. A more recent NYRR study pegged the marathon’s impact at $415 million.

Anecdotally, a marathon is a festive weekend where happy runners gladly shell out hard-earned money. For several years, I opted to skip the lottery and race-day hassle of the New York City Marathon (getting from the northern suburbs where I live to Staten Island was a brutal way to start a day whose focus was a 26.2 mile run) in favor of running the Philadelphia Marathon. My own economic impact was roughly: train ticket ($150 round trip), hotel ($175), dinner ($40), taxis ($40), post-race cheesesteak ($10). And that doesn’t include the traditional post-post-race visit to the Taco Bell/KFC combo on the way home from the Stamford Amtrak station, because, well, I just ran a marathon.

Since the mid-1990s, long-distance running pivoted from the fringe to the mainstream. The major marathons remain in the hands of local nonprofits that nurtured the races from infancy over decades and in at least one case (Boston), more than a century. Beyond those handful (which also includes New York and London), a thriving for-profit business of races is growing.

Turning races into a business feels like a somewhat obvious opportunity, if only for the demographics. You have a large, captive audience of mostly affluent people who’ve demonstrated their willingness to pay not insignificant sums for the privilege of punishing themselves over a period of many miles and several hours. Once you have them signed up, they’re more than willing to fork out more for a T-shirt, sweatshirt, or sticker to remind themselves, their family, and friends of their accomplishment.

Wittenberg, who in 2015 left NYRR to head a new sport company for billionaire Richard Branson, was among the first to truly recognize the marathon’s economic and social power. She is fiercely enthusiastic, and famously indefatigable in running circles, omnipresent at start and finish lines, a cheerleader for newbies and elites alike. She has marathon bona fides, winning a Marine Corps Marathon in 2:44 in 1987, good enough for a spot in the 1988 Olympic Trials (though she dropped out of the trials due to injury). She’s still a regular runner and does many interviews and meetings while on a run.

Her tenure at NYRR began in 1998, and she served as a deputy to then-CEO Allan Steinfeld, and then as CEO, beginning in 2005, charted a key period of growth in running. She’s watched both New Yorkers and others, of all ages, pour into the sport and presided over growth in her own organization that’s hailed by many and criticized by others as expanding far beyond its stated mission as a local club.

Here is the crux of the debate in New York, which speaks to one of the challenges of being the de facto leader of a high-growth sport on the biggest stage: Locals who loved it as a small club where they could run with their friends deplore its ever-expanding reach, not just throughout the United States, but the world, where Wittenberg traveled to woo the best runners to New York. She’s also an advocate for the sport for the young, as well as the underprivileged, believing that the simplicity and low cost of running make it an ideal weapon against poor health.

Her tenure was marred, if only temporarily, by the decision to cancel the 2013 race in the wake of Superstorm Sandy, which knocked out power across swaths of Long Island and Staten Island and drove many from their destroyed homes. Wittenberg took intense heat from runners and others for the timing and presentation of the decision. That controversy came weeks after a profile of Wittenberg in the New York Times illustrated, at great length, her difficult tightrope act of maintaining a running club’s local flavor in the world’s most famous city that happens to be the host of a giant marathon that runners globally are desperate to take part in.

Wittenberg and I first met, by accident, after overlapping runs in the Rockefeller State Park Preserve in Westchester County, just north of New York City. She’d come up from her home in Manhattan to run the trails that frequently host Olympic hopefuls, college cross-country teams from Fordham University to West Point, and hundreds of eager amateurs. In the high school parking lot where runners gather for weekend group runs, she chatted a couple of us up, and we all marveled at the beauty of the place. (Ben Cheever, a dean of our local running cohort, subsequently wrote a paean to the park for Runner’s World.)

We met later that year again, at a Bloomberg-hosted conference on the business of sports. She was grouped with the chief executive of the World Triathlon Corp., which puts on the Ironman, and the head of U.S. Pro Cycling Challenge.

Almost a year after that, we finally officially got together in her office. Her corner setup illustrated the nature of her job. She kept a standing desk that blends into a conference table; a nod, I imagined to how often she has to gather consensus from the various stakeholders cutting across government officials, runners, sponsors, and colleagues.

Wittenberg came to running competitively by accident, in college. She made good on a late-night dare to run a race the following morning and won (the bet and the race). She continued to run, including through law school at Notre Dame, and then as a young lawyer in Richmond, Virginia at Hunton & Williams. While working there, she won the Marine Corps Marathon up the road in Washington.

Running eventually evolved from avocation to vocation and she joined New York Road Runners in 1998, taking a 2/3 pay cut to pursue what she called a dream job that also allowed her to start a family and live what would theoretically be a less frenetic life.

It’s undeniable that the New York City Marathon, already famous when she took the NYRR helm, has only grown in stature. Wittenberg was among the architects of the World Marathon Majors, which grouped New York with Boston, London, Berlin, and Chicago. Through a point system, the top male and female professional marathon runners can each earn a separate title and $500,000 for winning the overall crown. The designation helped further cement the big five marathons in a class by themselves.

Wittenberg similarly pushed New York into previously untapped sponsorship relationships and, again owing to the race’s prominence, set the standard by which most other marathons are judged.

ING in 2003 became the first title sponsor of a marathon, negotiating its name into the race itself. What was known for more than 20 years as the New York City Marathon became the ING New York City Marathon. A Dutch financial services company, ING went all in on marathons, notching not just New York, but also races in Georgia and Miami. Its bright orange branding was integrated into the New York marathon’s color scheme.

The pre- and post-Sandy criticisms of Wittenberg came at a sensitive time. ING had decided not to renew its deal, so she was in pursuit of a new title sponsor. After months of meetings, she ended up not too far away, in one sense. Tata Consulting Services, known as TCS, already was a sponsor of the marathon. The India-based information technology company provided services related to the logistics of the race, including the ability to track runners in real time.

Wittenberg effectively upsold TCS into a role that was bigger in scope than ING’s title deal. Not only would the November event become the TCS New York City Marathon, Tata would lend its name to other NYRR races and programs.

While TCS wasn’t new, its deepening involvement signaled a shift in the sponsorship landscape, Wittenberg says. Once limited to what she called endemic sponsors, the pool of interested parties expanded. The endemics included shoe sponsors (Asics, in the case of New York, Adidas for Boston) and financial services firms (ING) that often advertise at sporting events with an affluent audience (think JPMorgan Chase and the tennis U.S. Open, and practically every bank in one form or another at many golf tournaments).

Now the roster of marathon sponsors has evolved, as its popularity has grown and the pool is somewhat more diverse. United Airlines is a “Foundation Partner,” making it the title sponsor for the New York City Half Marathon, as well as tagging its brand onto the marathon’s full title: “TCS New York City Marathon, presented by United Airlines.” Perhaps Wittenberg’s most interesting win in 2014 was the addition of Airbnb, the Internet-based service that allows people to rent out their houses, extra rooms (or couches) to visitors.

The deal was a fascinating one, especially as it signaled a change in runner demographics and attitudes. It was a nod to runners who said they wanted to travel to New York in part to be with other runners, especially the locals who might play host to them in a room rental, rather than hotel, set up. Like TCS and United, Airbnb signed on as a year-round sponsor, “to engage with us from events to training to youth programs,” Wittenberg says. In late 2015, her NYRR successors signed New Balance to a similar deal. “It’s a lifestyle connection, not just a one-day race.”

As Airbnb and other efforts illustrated, Wittenberg leaned hard into the young cohort that helps define New York City, beyond running. There’s the younger set—the Millennials who are increasingly filling up races, often in their familiar packs and who represent the surge of women into the sport—and then there’s the actual youth, the kids. There, Wittenberg and NYRR have poured time and resources. The organization’s annual report is filled with pictures and statistics about the youth programs, which help upwards of 130,000 kids in and outside of New York.⁴

NYRR’s also welcoming when it comes to other races and activities, seeing them as additive rather than subtractive to her ultimate cause of getting everyone who possibly can to run. “Free fitness, classes—all of it builds to people being fit for events,” Wittenberg says. “People will stay fitter longer, and it mitigates some injury risk.” For Wittenberg, running sits unquestionably at the center of the modern fitness boom. Its simplicity is its best asset. You don’t have to show up anywhere special or really invest much beyond a pair of shoes.

Maybe most importantly, running is beautifully efficient in the nexus of time and effort. A 20-minute run, especially outdoors, is often enough to take the edge off, to take you just enough outside yourself to feel some mental and physical benefit.

What Wittenberg and her successors at New York Road Runners have is New York itself. While the race is not technically difficult—the biggest inclines and declines are the long bridges between Staten Island and Brooklyn, and Queens and Manhattan—the necessity to touch all five boroughs requires logistical gymnastics that are hard on runners.

Runners spend the least running time, but the most sedentary time, on Staten Island. Since few stay on the island the previous night, the first order of business is getting out there, by bus or ferry from Manhattan. Then it’s a waiting game, punctuated by standing in line for port-o-johns. The scene is surreal, made more so by the setting of a former fort built for protection from Atlantic Ocean–borne invaders: Tens of thousands of jittery runners, some sprawled out reading newspapers, others jogging nervously to keep warm and keep the pre-race nerves in check.

The sheer numbers also provide challenges. The New York City Marathon is the second-largest annual footrace in the United States, trailing only the Peachtree Road Race in Atlanta, a 10-K held every July 4, according to statistics compiled by Running USA. It’s the only marathon in the top five. The differences between the Boston and New York marathons stand as extensions of the cities themselves. New York is big and flashy, often pulling in celebrities by virtue of its location and prominence. Back in 2003 no less than Diddy (aka Puff Daddy, aka Puffy, aka P Diddy) ran New York, complete with an entourage and motorcycle escort, in the middle of the field. He even branded it: “Diddy Runs the City.” More recently, in his post-Tour de France doping denial period, Lance Armstrong ran New York, breaking three hours by a whisker the first time, in 2006 (with a half marathon as his longest training run, he reportedly called it one of the hardest things he’d ever done), then knocked 13 minutes off his time the following year. Each November, it seems, some celebrity or another lines up in Staten Island.

For runners with big plans for a bucket-list race, New York is the most popular race to aspire to run. The race draws thousands of first-timers each year, many of them one-timers who want to check that box.

What New York lays claim to in flash, Boston counters in longevity and elitism. It’s the oldest marathon in the United States, dating back to the nineteenth century. And then there’s the qualifying.

While New York is singular as a city, Boston’s marathon stands alone. There is no single word that inspires more fear, aspiration, and envy for the serious long-distance runner. It’s become the touchstone for the 26.2 mile distance, the test that you must pass to consider yourself a serious marathon runner.

After the 2013 race, Boston became that much more important, owing to the bombings. The marathon that year became a where-were-you-when moment for runners and those who know them. I was thousands of miles away, sitting in a hotel ballroom in Sao Paulo. The private equity conference I was attending was mostly in Portuguese and I’d taken a break from the translation headset to idly peruse my Twitter feed.

As the details began to emerge, in 140-character bursts, I looked around to find an audience of oblivious mostly non-Americans. At a break, I sought out fellow New Yorkers, who had as few details as I did. One thing was clear that day: Like many others—some Boston veterans, others would-be qualifiers—I vowed to be on the starting line the following year.

It wasn’t a sure thing. Despite having a qualifying time, Boston hopefuls faced a new, more complicated process, made more complex by the fact that the 2013 race was stopped before a substantial number of people finished.

The upshot for the 2014 race, having nothing to do with the bombings, was that it was already harder to get in. Facing a race that filled up within hours, Boston dropped qualifying times across the board by almost 6 minutes. For a 40-year-old male like me, what had been a standard of 3:20:59 dropped to 3:15 flat. For a woman the same age, it dropped to 3:45 from 3:50:59.

The next change was how Boston rewarded those who exceeded their qualifying time by 5 minutes or more. Here’s how it worked: The race first opened to those who beat their time by 20 minutes or more. A few days later it was 10 minutes, then 5 minutes. Then, assuming there were still spots left, those within 5 minutes of their time could apply. Those registrants would then be ranked by fastest to slowest.

I fretted. My qualifying time was roughly 3 minutes faster than my qualifier. Boston had expanded the field for 2014, mostly to make room for those who’d passed the halfway mark in 2013 and were therefore guaranteed entry if they so desired. I watched and waited for the numbers to come out from the Boston Athletic Association (the BAA to most runners).

When the time came for me to enter, I realized I would be in a meeting so I neurotically asked my wife to submit my electronic entry. (Though I knew they would take them all in and rank them, what if you somehow got points for being one of the first to submit?) She gamely went to the website and sent me the confirmation of entry. I waited. Days passed. My two closest running friends were already in, by dint of being fast enough for early entry. They sent me encouraging texts.

Walking back from a lunch meeting on a sunny late September day, I checked email on my iPhone. There it was. I was in. Standing on a traffic island halfway across Park Avenue in Manhattan, I threw my hands in the air and whooped, figuring no self-respecting New Yorker would think twice about some idiot screaming for no apparent reason.

I found out later how lucky I was. Because of the demand for the 2014 race—all of us who vowed to show up in solidarity for the victims of the previous year—not everyone who qualified got in. When all was calculated, the effective qualifying time was a minute and 38 seconds faster than the standard (e.g., 3:13:22 for my age cohort). Even with the extra room, 2,976 runners who crossed a finish line sometime in the previous 18 months with a coveted Boston qualifying time (also known as BQ) were denied entry.

Getting into Boston brings the same fleeting joy as getting a really difficult new job. There’s a thrill, and then you realize you have to actually do it, and more important in the case of the marathon, train for it. And for anyone who lives and trains in the northeast United States, Boston makes you work for it all over again.

Training for the New York City Marathon is a relative pleasure. Summers in and around New York are relatively mild (especially from the perspective of a native Southerner). The days are blissfully long, so even 5:15 a.m. runs happen in natural light. Temperatures moderate even more as fall arrives. Long runs double as foliage tours and, once the chill really sets in, the race is upon you.

Boston training is an entirely different matter. Most training plans stretch over 14 to 16 weeks, so work begins just after the first of the year, also known as the period in the north where you question your life choices. Winter in New York, and certainly Boston, stretches out through March, when snowstorms aren’t rare. Darkness is a given. Those long days of summer translate to brutally short days in January and February. And it’s usually cold.

The winter of 2014 was a soul-crushing ordeal. Record snowfalls, polar vortexes, and plunging temperatures made training even more daunting than usual. My running partner Wendy and I ran more than once when it was four degrees, much to the chagrin and pity of family and friends who wondered if we’d been apprised of the invention of the treadmill or had lost our minds altogether. I slipped and fell several times on icy roads. The Adidas poster that I got at the Boston Marathon a few years earlier read “Boston With Swagger;” it hung in my basement and seemed to mock me every morning as I put on layer after layer and checked the batteries in my headlamp. I was swagger-less.

April finally arrived. I navigated the additional security, marveling at the oddity and sadness of going through a metal detector to run 26.2 miles. Even with local police and imported law enforcement everywhere, with bomb-sniffing dogs and strict rules about checking bags—or perhaps because of all that—the morning was electric.

We made the long walk from the high school grounds that once a year become the staging ground for tens of thousands of jittery runners. I stood at the starting line in Hopkinton and listened to a rendition of the national anthem that meant more to everyone that morning. And then race director Dave McGillivray gave us our instructions. “Our job today is to take back the finish line,” he told the assembled runners. It was on.

Here’s the thing about the Boston Marathon: It’s really hard. You work your butt off to get there in the first place and then the Boston Athletic Association presents you with what has to be one of the most technically challenging courses out there, certainly of the major, popular races.

Part of the challenge is that the first half is distinctively not hard. It’s actually shockingly easy, because most of it is downhill. Hardly anyone can resist going out a little too fast. Others blow it out completely. The second half comes with a relentless set of hills, culminating with Heartbreak Hill. The course then turns sharply downhill, and your quads, having been tortured through the inclines, scream. It is somewhere in that next couple of miles, as the outlying neighborhoods give way to Boston proper, as the Citgo sign sits tantalizingly out of reach at Fenway Park, that most of us ask the question of ourselves: What the hell am I doing here? The exhaustion, mental and physical, is acute.

In Boston the answer comes, finally, on Boylston Street, the final stretch. Twenty-six miles behind you, point-two to go. As there were every other year for decades, the throngs of spectators were 5 to 10 people deep in 2014. I crossed the finish line and spent the next 20 minutes hugging and thanking, and being hugged and thanked. My buddy Billy and I—stinky and fit-for-a-marathon thin—posed for a picture with a couple of beefy Boston police officers. It hangs on my fridge to this day; all four of us are grinning like idiots.

It was true that our very presence there, the full-throated, eager, 36,000 of us who endured the long winter, the qualifying drama, and heightened security was a bold statement against the previous year’s horror. But the real show was the classic American response: spending money.

The center of commercial activity for the marathon economy is the race expo, where lean, hungry, amped-up runners show up to collect their race numbers, free T-shirt, and whatever else the sponsors have shoved into the goodie bag. But that’s just the beginning.

The Boston Marathon expo stands as the cathedral of running commercialism. Its icon is the Boston jacket.

No one I’ve met who’s run at least one Boston Marathon doesn’t have at least one Boston jacket. It’s the status symbol that says to your running friends, “Check.” It’s not an attractive piece of clothing, but a glorified windbreaker made by official sponsor Adidas with the marathon logo embroidered on the back and the left breast. It has stripes down the side. Buying one is totally awesome and completely worth the $125 they cost at the 2014 race.

But the jacket is only the beginning. In the Adidas area alone, where runners are funneled first (lead sponsorship has its privileges), there were T-shirts (my favorite, which I bought for each of my three sons, read “My dad is faster than your dad”), pint glasses, flip-flops, sweatshirts, and more.

The Adidas section, while the biggest, is just the beginning. Once through that checkout, the expo becomes a bazaar of booths hawking everything from shoes to energy gels to self-massage devices (some of which look and act like medieval torture devices).

Runners are ferocious spenders, many by virtue of simply having the disposable income to shell out. Like tourists turned out of a bus on New York’s Fifth Avenue, many runners show up ready to throw down cash or credit for a variety of goods that will make them even a little bit faster. (I once spent $20 on a wristband that promised to help me harness my energy; I ran a PR—runners’ abbreviation for “personal record”—the next day, so couldn’t totally dismiss it.)

Figures on how much people spend at expos are difficult to nail down, but I spotted a thread on a Runner’s World message board populated ahead of the 2014 Boston Marathon. The question was simple: “How much money do you think you’ll spend?” Among the several dozen responses were some expo estimates. The low end was $50, but several admitted that they expected to spend $100 or $200, with at least one person conceding they would drop $500. Another commenter, fearful of his own weakness, said he planned to “lock up his wallet.”

Outside of New York and Boston, there are upwards of 750 marathons every year in the United States and Canada, the vast majority of which are smaller. (The 10 biggest races comprise roughly two-thirds of the total participants.) While the biggies slug it out for dominance, a just-as-interesting competitive set lurks one level down.

Patrice Matamoros revived Pittsburgh’s Three Rivers Marathon in 2009 after the race was dormant for five years. Five years after the resurrection, the race was among the fastest growing in the country. It’s a study in how it all comes together, and the challenges and opportunities inherent in the rest of the races.

Pittsburgh is an old-school American city in many ways. Once a dominant economic force owing to its steel mills and other heavy industry, it slumped through much of the late twentieth century. During the early part of the twenty-first, though, it pivoted right into a new urban trend that favors a lower cost of living, work–life balance, and advanced, information-economy jobs. Pittsburgh has a slate of high-profile colleges and universities, notably the University of Pittsburgh and Carnegie Mellon University, the latter of which is well-known for producing high-earning, sought-after engineers. Fitness fits in nicely.

That’s what Matamoros thought back in 2008, when the entire staff of the revived Three Rivers Marathon consisted of her. She’s a former star high school and college runner, sidelined in her thirties by injuries. She gets the running thing. When she was approached about the marathon job, Matamoros was a transplanted, very successful local fundraiser. She immediately fell in love with the marathon.

The race had essentially faded away. But Matamoros found a city still ready to back it, both municipally and commercially. “In the beginning it was me going in and selling the dream,” she says. “With the thought of bringing back, it was more nostalgia. People really didn’t know what it could be.”

Her approach was to shoot the moon. She told her board of directors she could pull in 5,000 runners; they asked to publicly aim for 3,500. In its re-inaugural year, the race drew about 10,500.

Like other organizers, she found a radically changed customer base that was less die-hard. She cited statistics around the increasing average finish times—“The average was 2:52 back in the 80s, now it’s 4:52.” (While slightly exaggerated, the numbers aren’t far off.) There are a lot of people able, and willing to run that speed, and putting on a race became largely about “making it easy and fun,” she says.

Matamoros was competing in a crowded market, aiming to grab a chunk of the spring marathoners. Pittsburgh sits in the midst of the spring marathon calendar, the same weekend as the Cincinnati Flying Pig and a week removed from Cleveland, both within driving distance. Matamoros’s answer was to appeal to the Millennials and women in her backyard and beyond.

What Matamoros found was that Millennials favored a buffet approach to their lives, at work and at play. They wanted the opportunity to sample lots of different things. Social media allowed them to dabble, and to have a slice of this experience or that. With them in mind, Pittsburgh quickly moved past just offering the marathon distance to include a half marathon (now the biggest of the weekend’s events), as well as a relay option and a 5-K.

The Generation X crowd was similar, but distinct. Extending the restaurant metaphor, this group prefers to order a la carte, having done lots of homework about their best options. “They’re very particular about what they pick and choose,” Matamoros says. “They like the VIP experience; they want the option to switch races.” (Unlike some other events, Pittsburgh allows changes among distances up to and including race weekend, and processes roughly 1,000 such switches every year, for a $20 fee.)

While Millennials were the most popular demo, Generation X had set it in the public consciousness, she says. “Gen X was the self-help generation. This was a way to be empowered, to make yourself belong by showing power and self-confidence. It became a way of showing they’re taking their lives back, grieving through a loss or getting over a divorce,” she tells me.

Like many of her fellow race directors, Matamoros came to appreciate women participants, who comprise 60 percent of her runners. “We love them because they commit early,” she says. “They bring their friends.” Often four or five women will register together, creating a tighter connection to the event.

Going forward, Matamoros said she’s focused on several strategies including making the experience last even longer. With Pittsburgh teed up to an Olympic qualifier for the 2016 Olympic Trials, she created a “Game On Pittsburgh” program that hooked runners from sign-up. “From the moment you register with us, you’re connected,” she says. The runners, already connected with many of their fellow racers through social media, will become a more formal part of a race-created ecosystem.

Like Wittenberg, she’s looking to leverage the enthusiasm of nontraditional races like Tough Mudder and The Color Run by converting their newbie athletes into runners. “I love them,” she says. “People who didn’t think they were runners, it converts them. It’s playing a vital role in the marketplace, I just have to make sure the next step is with me.”

Matamoros and Wittenberg both noted that while being not-for-profit has advantages and drawbacks, much of it is on the margin, and few participants make much of a distinction among various races’ business models.

“It’s a business for all of us,” Matamoros says. “What we’re talking about is a classification. My job is to show how we’re different.”

It’s that competitive aspect, both on the course and behind the scenes that eventually led to what may have seemed inevitable or obvious—turning racing into a big, money-making business.

Taking the local club to the world was Wittenberg’s mission at New York Road Runners. She says she always wondered what it would be like to have an even bigger canvas to paint. For that, she needed a singular individual—someone like Richard Branson.

Wittenberg claims she wasn’t looking for a new job when the Virgin billionaire’s reps came calling. Her first signal was a whisper from a headhunter who, without naming names, said there was a notable individual with a deep interest in the area who saw an opportunity to get people moving. With a little more details attached, she thought to herself, “Oh, that’s Virgin, that makes sense,” she says. “And I didn’t think about it again.” A few months later came a more expansive approach, this time with the Virgin name attached. In the spring of 2015, she met Branson and accepted the job. NYRR effectively split her job between two of her lieutenants. Michael Capiraso became the President and CEO of the organization; Peter Ciaccia was named President of Events and the race director of the marathon.

“I always wanted to take this idea of community-based running and fitness on the road,” she says. “To take people from the bucket list and keep it going.”

We’re sitting in the southwest corner of Central Park, a few blocks from Wittenberg’s old NYRR office, but uptown from her new Greenwich Village Virgin digs. She’s in the neighborhood because it’s three days before the New York Marathon, the first one in about two decades when she won’t be some sort of race official. But the same quasi-celebrity status in the running world that made her stand out in Boston is at work here. After seeing me, she’s headed to see Paula Radcliffe at a marathon hall of fame event.

Virgin Sport, her new project, is short on specifics but big on vision, the way Branson ideas usually start out. He’s deeply into wellness and fitness overall already, through a corporate service called Virgin Pulse and a gym business. Virgin Sport, in theory, is a way to tap into the community-building aspect that’s building around running, cycling, and other participatory sports. The opportunity, she says, is in the “gray area of fitness.”

“It’s the day-to-day,” she says. “Everyone can get up for the big race, but how do you weave it in to your life? I believe we’re all better together, with others. Connection with others is key to bringing the fun and play to sport, and getting us out the door.”

Wittenberg’s initial answer is local clubs powered by the trademark Virgin customer experience—something anyone who’s ever flown on one of Branson’s airlines knows well. It’s a cheeky, winking experience that reflects simultaneously the whimsy and purpose of its founder. That experience, she surmises, is especially important to the up-and-coming generation of fitness fanatics, the Millennials who will drive the communities she aims to build. “A sense of purpose is going to remain important,” Wittenberg says. “This is a generation that says, ‘We care about who we shop with and who we support,’” she says.

It’s also a generation that appreciates blending purpose with profit, and the members of the fitness economy are willing to pay for brands and services they believe in. That’s in part what makes Wittenberg’s transition from noble nonprofit to a more capitalistic enterprise possible. Virgin, after all, is a for-profit company, funded initially by the Branson family, but with an eye toward bringing on additional investors down the line. Its success will hinge on Wittenberg’s ability to wow the paying customers.

“The Virgin brand is about what’s amazing for the participant, and the community,” Wittenberg says. Making it amazing will be that much more important as she enters a market that seems to get more crowded with competitors each day. Along with her former colleagues and friends at the big-ticket marathons, there’s an ever-growing pack of entrepreneurs aiming to please that same pool of athletes.