The Founder of 14ers.com Finally Shares His Story

Skiing down the couloir on the north face of 14,268-foot Mt. Blue Sky is all about timing. Avalanche danger on the state’s 14th tallest peak is particularly high in midwinter, so experienced backcountry skiers know to hold out for the comparatively stable snow of May and June. But it’s not just about the time of year; it’s also about the time of day. There’s a magic hour—sometime after the morning sun has softened up the icy crust and just before those same rays turn the steep slope into a sloppy mess—that people like Bill Middlebrook and Nick Gianoutsos know to wait for. Only then do they drop into the narrow, rock-strewn gully.

The sun was popping in and out of the clouds and the wind was tolerable on June 11, 2023, making it a seemingly ideal day for Middlebrook and Gianoutsos to snap on their crampons, lash skis to their backpacks, and bootpack roughly a mile to the summit. But by mid-morning, the snow was refusing to shed its crunch. The men hung out at the top of what expert skiers consider an intermediate big-mountain line, hoping for even a slight improvement in conditions. When the snow finally began to soften, Gianoutsos, 45, decided to clip in and go first. After he came to a stop partway down the couloir, he turned to watch Middlebrook. He had form worth ogling, but Gianoutsos also felt an outsize responsibility for the then-56-year-old.

Middlebrook wasn’t just another ski partner. He was the founder and sole operator of 14ers.com, a website revered by the hiking/climbing/backcountry skiing community for its deeply reported, meticulous trip reports for Colorado’s 58 named mountains that rise above 14,000 feet. Every time Gianoutsos went skiing out-of-bounds with Middlebrook, he carried the weight of bringing home safely the quiet, attention-deflecting man who’d nonetheless become something of a cult hero in Colorado.

So, it was with no small amount of horror that Gianoutsos watched as his friend of eight years caught an edge, fell face-first, and careened over a granite outcropping with a 12-foot drop, his Salomon skis and Black Diamond poles scattering in all directions. Oh crap, Gianoutsos remembers thinking. Please let it be just a broken arm.

Somehow nothing was fractured or shattered, except maybe Middlebrook’s confidence. Knowing his fall had also shaken Gianoutsos—who’d just kept saying “that was scary, man, that was scary”—Middlebrook sent an uncharacteristically verbose yet predictably pragmatic text to his partner the next day acknowledging that his aging body might not be able to handle the terrain like it once had. Maybe, he conceded, it was time to think about slowing down.

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The smell of good coffee suffuses the air well before daybreak creeps through the windows in Bill Middlebrook’s home office. By 4 a.m. on days when he’s not planning to resort ski or make backcountry turns or hike a very tall mountain, the husband and father of two adult children is up and using what he calls “coffee time” to get a jump on his whiteboard checklist. The 14ers.com website—which he launched 25 years ago as a hobby and which currently averages 20,000 unique visitors on summer days—still occupies him for roughly 20 hours a week, not including research time he spends on the trails or sleepless nights spent troubleshooting a server crash.

At five-foot-seven with ruddy brown hair, intelligent eyes, and a coaxable smile, Middlebrook comes across more like the computer whiz he is than the accomplished outdoorsman he also happens to be. Although friends label him an introvert—this is the first lengthy interview he’s given about himself or the phenomenon he birthed with 14ers.com—and say he avoids introducing himself as anything other than “Bill” on the trails, he isn’t shy. Unlike most people who have created something undeniably cool, Middlebrook simply doesn’t want the laurels. He has always preferred any attention to be centered on the site, not on him. His reticence has, paradoxically, only served to catapult him into the-man-the-myth-the-legend status among those who ply the state’s loftiest footpaths.

Icon or not, on any given morning, the retired software engineer might need to update information about new parking rules at some far-flung trailhead or upgrade functionality for one of the site’s myriad tools. It’s just as likely, though, that Middlebrook recently reclimbed a mountain—something he does about 25 times a year—and has new photographs to add to one of the existing route descriptions he has written and rewritten over the years.

In pursuit of those route descriptions, of which there are 179, Middlebrook has reached the summit of a Colorado fourteener 513 times. He has bootpacked up and skied down 46 of the state’s 14,000-foot mountains, including, of course, Mt. Blue Sky. He began laying the foundation for the site way back at the turn of the millennium, when he realized, quite astutely, that websites were going to be able to do something that guidebooks couldn’t: remain up to date. “My grand plan was,” Middlebrook says, “let’s put this on the internet, keep it from becoming obsolete, and provide it in a way that will help people—for free.”

Middlebrook could afford to be charitable because, as he says, “I was set.” In 1998, he and three partners sold their Massachusetts-based e-commerce software and consulting firm for an undisclosed—but life-alteringly large—amount right at the top of the dot-com bubble. Middlebrook stayed on with the new company for a little more than a year before retiring in February 2000. At 33, Middlebrook looked at his bank account and determined it could handle a little passion project. He didn’t want or need to charge users a fee. He was content to buy the domain name and pay the few hundred dollars in annual web-hosting fees to keep his coding skills sharp and his body active.

Except what Middlebrook had created wasn’t trivial at all. As it turned out, people were starving for the highly detailed, user-friendly, continually updated, free content he was publishing. They wanted to know when local trail-building organizations had reworked sections of poorly constructed paths. They craved minutiae about U.S. Forest Service restrictions. They needed to understand the risk factors of this route versus that route.

“It only took a couple of years for me to figure out that this was going to cost a lot of money,” Middlebrook says. That’s because, over time, he had dressed up the basic route descriptions with thousands of annotated photographs and added tools like maps, user-generated content in the form of trip and condition reports, trailhead status updates, and (in 2005) a forum that allowed registered users to communicate among themselves. “I went from using what’s called a shared hosting server to realizing that I needed dedicated equipment and massive amounts of bandwidth to be able to support the volume,” he says, “because people weren’t just surfing text. They were downloading thousands of photos and maps.” With traffic to the site doubling and then doubling again—and then again—costs went from a few hundred dollars a year to upward of $10,000. Middlebrook’s vision had always been a fee- and advertisement-free site, but even he couldn’t justify such an expensive pastime. Still, a retirement spent on the golf course wasn’t going to make Middlebrook happy.

That’s how his wife, Lisa, ended up toiling in what she jokingly calls the “14ers sweatshop.” Headquartered these days in the basement of the couple’s 3,000-square-foot, new-build home in Pine, the sweatshop consists of boxes of T-shirts that Middlebrook designs each year and sells on the site. Over the decades, proceeds from mouse pads, coffee mugs, bumper stickers, and T-shirts emblazoned with “14ers.com” have mostly covered the web-hosting bills. Individual, non-tax-deductible donations and revenue from a few affiliate links have usually helped offset the rest. “I don’t mind folding and shipping shirts,” Lisa says. “It’s for a good cause. He loves it too, even though sometimes when he wears a shirt, he gets recognized, despite how hard he tries to stay incognito. They’ll say, ‘Are you the Bill Middlebrook?’ ”

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It was about a nine-mile bike ride from 14-year-old Bill Middlebrook’s house in Lanesborough, Massachusetts, to the Springs Motel, where for two years he washed dishes in the restaurant’s kitchen. At 15, he added another gig when he began a five-year run of spinning the lifts and slinging rental equipment at Jiminy Peak, the largest ski resort in the state. Middlebrook and his older brother loved to hike and fish and hunt in the Berkshires, but teenagers in his community knew how to work. That was especially true for Middlebrook, who’d lost his father at nine years old and who’d watched his mother labor at a paper products company for his entire childhood. Also, he says, “I was saving up for a car.”

At 18, Middlebrook drove his used Ford Fiesta hatchback a half hour north to North Adams State College, where he enrolled in the school’s new computer science program and quickly found he had a knack for software development. After graduation, he worked for a short time at a local consulting firm—which also employed a young woman named Lisa Pettinichi—before splintering off with three co-workers to open the Kodiak Group, a startup that helped companies integrate e-commerce into their operations.

Middlebrook describes 1994 to 2000 as a blur. Of the four co-founders of the Kodiak Group, he was the one with the technical expertise, but computers and the internet were so new to most people at the time that he often had to go on sales trips across the country to explain to potential clients why, for example, there would no longer be any need to fax a purchase order if it could be delivered via electronic transfer. Those aspects of the job could’ve easily constituted a full-time gig, but Middlebrook was also the guy running cable through the ceilings and rebooting servers when thunderstorms knocked out the power in the middle of the night. He easily logged 70 hours a week. “Each year of that work was equivalent to five years of normal work,” he says. “I don’t remember much of the ’90s. It was very stressful.”

But as the Kodiak Group grew—from four to 100 employees—the expansion gave Middlebrook a chance to live out a dream he’d had since first visiting Colorado in the late ’80s. “We’d stayed in Winter Park but also skied at Vail and Breckenridge,” says Middlebrook, who picked up a few backcountry skiing and hiking guidebooks—such as Gerry Roach’s Colorado’s Fourteeners and Lou Dawson’s Dawson’s Guide To Colorado’s Fourteeners—on subsequent trips to the Centennial State. “I was blown away by Colorado, and I was convinced I was going to move here someday.”

Someday came in 1998, when the Middlebrooks—who’d married in 1993 and had a daughter in 1995—set up base camp in Evergreen and opened a Kodiak Group office in Lakewood. When he wasn’t working, Middlebrook was often skiing or hunting, but he also picked up a new interest: peak bagging.

While still “stuck” in New England, Middlebrook had began paging through those old guidebooks. Quandary Peak quickly caught his attention. The 14,272-foot summit looms large in the Tenmile Range just southwest of Breckenridge Ski Resort, and it looked big and bad to Middlebrook back then—especially when compared with the gentle, rolling loveliness of the sub-3,000-foot Berkshires.

Hiking Quandary for the first time in 1998 ignited in Middlebrook a passion for all of Colorado’s fourteeners. He loved how accessible the state’s mountains are. He delighted in covering ground simply to see what was around the next bend: crystalline lakes, jagged rocks, fields of blue columbine, squeaking marmots. He reveled in the unobstructed views from above 14,000 feet. The draw of the high country was so irresistible, in fact, that the Middlebrooks ultimately moved from Evergreen to Breckenridge, where Quandary sat in his proverbial backyard.

The then-32-year-old hatched his plan to launch 14ers.com in early 1999 and—with Rush, Led Zeppelin, or a little jazz providing encouragement—began clambering up every 14,000-footer in the state. To fashion route descriptions that would better help hikers avoid going off-trail (and, therefore, getting into potentially environment-damaging, frustrating, or dangerous situations), Middlebrook made sure his daypack included a pen and notebook as well as his 35mm Minolta. “There have been days when I gained an extra 700 feet of elevation,” Middlebrook says, “and walked way out of the way just to be able to, for example, take a picture that might show someone why this isn’t the way to go.”

Back in his office, Middlebrook would use a scanner to digitize his four-by-six-inch prints, upload them to the site, and painstakingly embed them into his turn-by-turn route descriptions, the language for which he tried to make uniform and exceptionally clear so site users would come to know what to expect when he wrote “excellent trail” or “difficult terrain” or “semi-exposed area.” Middlebrook didn’t stop at the so-called standard route—the most well-established and usually easiest trail—for each mountain. Instead, he undertook the same arduous process for every possible path on a given fourteener (and, starting in 2004, on thirteeners for 13ers.com, which he merged with 14ers.com in 2015). In some cases, that meant hiking, photographing, and then crafting as many as eight different route descriptions for one peak.

Not only was Middlebrook continuously adding or updating, but he was also enhancing the user experience by posting complementary content (about the easiest mountains for beginners and suggested gear) and offering critical tools (like digital topo maps), all of which was available to anyone who simply keyed in the URL. To access some sections of the site, however, Middlebrook began requiring visitors to create free logins in 2005. By compelling people to fashion usernames and giving them the ability to fill out a checklist of summits they’d tagged, Middlebrook gave rise to something that was arguably as valuable as his route descriptions: a community.

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At 8:31 p.m. on May 6, 2007, colopilot2002 created the first post in a thread titled “Climber injured and stranded on Humbolt Peak” on 14ers.com’s forum. Along with a link to a 9News story, colopilot2002 mentioned that the unnamed 38-year-old climber was stuck somewhere above 12,000 feet. Nineteen minutes later, sdkeil responded: “Hmmmm I hope this isn’t what I think it is about. USAKeller and TalusMonkey went to climb Humbolt this weekend. I think TalusMonkey is 38 and neither are answering their cell phones. Let us all hope for the best.”

Over the next three days, 497 posts told the story of a community that would lose one of its own in David Worthington. A glissading mishap led to catastrophic injuries and a night spent in the elements above timberline, despite the best efforts of Caroline Moore, aka USAKeller, to descend quickly and find help. When a search-and-rescue operation reached the climber alive the next day and asked him his name, Worthington didn’t say “David.” Instead, he whispered, “TalusMonkey.” He died that night at a hospital in Pueblo.

On that heart-wrenching weekend in 2007, the 14ers.com forum gave Colorado’s hiking set a place to deliver and receive updates, offer assistance, tell stories, and grieve. It did the same when 24-year-old Rob Jansen, aka rjansen77, died in a rockslide on Hagerman Peak in August 2012. That same month, the site helped create a happier ending for another injured soul, this one a German shepherd that had been abandoned on Mt. Bierstadt. By coordinating a rescue operation on the forum, 14ers.com users saved the pup.

“Bill has brought a lot of people together,” says Ryan Richardson, who found so many hiking-partners-turned-friends at 14ers.com happy hours in Denver that he began coordinating similar meetups in Boulder. Richardson also serves as a volunteer administrator on 14ers.com’s nearly 80,000-strong Facebook page so Middlebrook—who’s not a fan of the trolls on Meta’s site—can focus on 14ers.com.

Although the Facebook page is often a haunt for newbie hikers, 14ers.com caters to peak baggers of all experience levels. Even expert mountaineers can mine for beta gold on Middlebrook’s pages, particularly in the trip reports and peak conditions sections, where registered users can post narratives detailing their adventures or offer quick-hit notes about how much snow is still on a given trail on a late-summer day. “I love seeing reports from someone who’s ahead of me on the checklists,” says Brad McQueen, who has summited all of the state’s fourteeners and is now chasing the thirteeners. “If wildwanderer has done a peak, I read the report. I know it’s gonna be good.”

More experienced climbers like McQueen also help Middlebrook in his mission to keep hikers safe, especially on the state’s most treacherous peaks. In 2017, when five hikers died on Capitol Peak near Aspen, McQueen soloed the mountain the following summer to try to pinpoint where people were getting off-route—and falling to their deaths. “I figured out one of the problem areas, I think,” says McQueen, who went home and wrote up a trip report to warn prospective hikers. “There’s a gully that looks like a shortcut down to the lake, but it’s a death trap. Hikers cliff out with 800-foot drops below them.”

Middlebrook updated the site’s Capitol Peak route description with similar language, but that 14,138-foot massif isn’t the only troublemaker. “There are just certain routes that require me to look for something that is causing so many calls to search and rescue,” Middlebrook says. “Kit Carson is a good example.”

Since 2010, four people have died on the trail to Kit Carson Peak, a 14,167-footer in the Sangre de Cristo Mountains. Middlebrook has re-hiked the Via Challenger Point standard route several times, always assessing what part of the tricky terrain could be leading people astray. “There’s this one feature called Kit Carson Avenue, which is a long ledge that people use to get to the summit,” he says. “On the way back down, if you don’t pay attention, you can miss it because it kind of peters out. There have been plenty of search-and-rescue missions, and some people have died by missing the Avenue. So, in 2014 and 2019, I made it a point to put extra language in the description.”

A few years after Worthington’s death, Middlebrook also made a point to build a Climber Memorial page on 14ers.com. Tributes to dozens of fallen mountaineers will live in perpetuity on the site—as long as Middlebrook remains its keeper.

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The Robot on Maroon Peak. The V-notch on Mt. Sneffels. The Crux Wall on Mt. Lindsey. The Old Shack on Mt. Belford. Hikers know these landmarks by name because Bill Middlebrook christened them as such. He calls them “milestones” and specifically looks for quirks in any landscape that could provide hikers a point of reference, especially in areas where recreationists tend to get confused. Then, in his route descriptions, Middlebrook inserts a red marker, a quick click of which allows the user to view the milestones on a map. In the mobile apps—he launched iOS and Android versions in 2011—milestones are converted to coordinates to provide location information to the user. “It’s kind of corny,” he says, “but it’s helpful.”

It’s also important, and not just because those milestones do disoriented hikers a solid. “Bill has shaped the way we think about mountains, the way we learn about mountains, and the way we talk about mountains through his website,” says ski partner Nick Gianoutsos, who met Middlebrook through the site. “There’s also an important historical component here. The names of climbers, the people who have passed away, the different trends or concerning issues from year to year, the trip reports people write—all that is documented and serves as a public record of the history of climbing in Colorado.”

Which is partly why people like Gianoutsos and Ryan Richardson—as well as some of Middlebrook’s other skiing and hiking partners, like Craig Lizotte and Otina Fox—fear what will happen to 14ers.com when its founder decides he wants to retire from a retirement that many people never understood in the first place. “That’s because not many people really know a lot about Bill,” says Lizotte, who has summited roughly 100 peaks with Middlebrook. “He has created this site because he loves the research, he loves the quest for knowledge, and he is a caring, giving person who likes helping other people get off the couch.” But that doesn’t mean he wants to do it forever. In October 2022, Middlebrook posted a few paragraphs on the site that addressed the issue, saying he planned to continue managing 14ers.com for “at least the next few years.”

What Middlebrook didn’t mention, but explained at his kitchen table in early 2025, is that he has no obvious successor. There simply aren’t, he says, a lot of computer programmers who have 20 unaccounted-for hours each week who also want to hike 25 mountains every year and do it all for free. Middlebrook acknowledges that there could be someone out there who wants to buy the website—though no one has approached him with a serious offer, and the user-generated content on the site could present ownership issues—but he’s not really looking to sell. “If I sell it to somebody,” he says, “and they start charging people for it or putting advertising on it, it gets away from what I originally wanted it to be. It won’t be my baby.”

What he’d really like to do is give 14ers.com to someone—maybe a few someones—who simply wants to take the torch, even if that person would need to outsource the technical aspects of the site. If he can’t find a beneficiary when he’s ready to log off, a last resort would be to leave it in a read-only form until he finds a suitor. And if that never happens, Middlebrook would shut the site down rather than let it get “stale,” a word he spits out as if it were an expletive. But he’s not ready to reconcile with that future just yet, so in the short term, he’ll keep updating and tinkering and adding. Until he finds an heir, he’ll keep his morning coffee date.