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John continued to pay for Bayard's education, and at fourteen he was sent away to barding school in Deerfield, Massachusetts. Back home on breaks, whatever house they were living in at the time became party central for Bayard, Gren, and their buddies. Bayard was boisterous and physical; moving back an forth between two very different worlds left him feeling that he didn't quite belong in the one where the Winthrops had always stood.

In his teens, Bayard spent a lot of time at the houses of his friends, in a sense adopted by more stable families. The  Kendalls were one such family. Don Kendall, the father of Kent Kendall, Bayard's close friend from Country Day, was a self-made success who had grown up on a dairy farm and served as a navy pilot during World War II. Don went to work for PepsiCo as a delivery driver after being discharged and rose through the corporate ranks to become chief executive. He earned renown as the boardroom mastermind behind the cola wars of the 1980s. "Even though he was a CEO, my dad was very present," Kent Kendall told me. "He was playing football with us. Breaking out the  snowmobile or taking us on the tractor. Bayard was probably like, 'Wow, this is what a happy family and an engaged
dad looks like.' He was definitely looking for that." Mr. Kendall, as Bayard continued to call him even as an adult, became a role model, a blend of old-fashioned bootstrapping and exceptional achievement in business.

When it came time for college, Bayard made a halfhearted attempt to follow in the Winthrop tradition and applied to Harvard, but he'd been an underachieving and directionless student and was waitlisted. He ended up at the University of Vermont, where he came into himself. Bayard's college friends told me that between his sophomore and junior years, an engine of ambition kicked in. He spent a month in Wyoming's Wind River Range as part of a course at the National Outdoor Leadership School, lost a bunch of weight, and set his sights on Wall Street. After interning at Donaldson, Lufkin & Jenrette for two summers, Bayard was accepted into the New York investment bank's prestigious trainee program following graduation, in 1991. He shared a tiny Upper East Side walkup with a college buddy who also worked in finance and a childhood friend from Greenwich. Dressed in a suit and tie, he logged grueling eighty-hour workweeks as a junior analyst. He still didn't care about clothes, but occasionally a colleague's footwear would catch his eye in the elevator. "Every now and then," he said, "I'd find a great pair of shoes and go, Those are awesome fucking shoes!"

Bayard soon grew to dislike Wall Street's culture of macho bluster and punishing workloads, however. "Friday afternoons," he recalled, "there was this staffing guy there. He would wander the halls and look for any analyst that didn't have smoke coming off their computer and assign them stuff. Like ruining your weekends." It instilled a work ethic that has served him well, "But the part I didn't like was it reminded me of the fraternities in college. This idea that you were rewarded for acting really busy as opposed to the actual work." He also found life in New York confining; he longed for a pickup truck and a dog. In 1993, after two unhappy years, he quit his finance career and left the city, turning away from the Winthrop path for good. His plan was to drive cross-country to Seattle and work construction, but then an old friend happened to call. As they chatted, the friend remarked on the new lightness in
Bayard's voice. "You don't have any interest in moving to San Francisco, do you?" the friend asked. "I'm moving out there, and I want a roommate."

* * *

Here's what Bayard was interested in: working for a company that inspired him. He wanted a tangible output to his day, to produce real things—no more selling institutional investors on corporate debt. In San Francisco, he learned through his roommate about a tiny company, Atlas Snowshoe, whose signature product was a spring-loaded binding that reduced drag as you walked. He'd never gone snowshoeing in his life. But it was a product, and the hands-on nature of the enterprise—"a couple of guys in a fucking warehouse in a shitty part of San Francisco making it happen," as he put it—appealed to him. He spent months begging the founders for a job. "I was like, 'Hire me, hire me. I'll clean your fucking toilets.'"

Short and boxy through the trunk, with bristly cropped hair and a ruddy complexion, Bayard had the physical appearance and scrappy intensity of a wrestler. Atlas hired him, and he never stopped working. Now that he'd found his purpose, he was bursting with energy, ideas, and opinions. Always strong opinions. He eventually managed sales, customer service, and production for Atlas. He made peanuts compared with his old Wall Street salary, but, he said, "I
fucking loved it. It felt so real to me in a way that investment banking had not."

In 1996, Bayard left Atlas and networked himself into a job as president of one of the first webchat sites. It was an internet start-up with no product, but he figured it was the next logical career step to becoming a hotshot Bay Area CEO. "It was the first internet wave, and there were all these search engines like Yahoo and Infoseek. Everybody believed that sticky audiences were everything—and we had a huge audience. They would stay online for like ninety minutes a session because they're talking about right-wing politics or whatever the hell they're talking about." He got
two valuable things out of the experience: a million-dollar windfall when the company was sold to Disney a few years later and the realization that he was not destined to be the next Silicon Valley wunderkind. "I hated this internet chat community shit."
_______________________________________________________________

***** TABLE OF CONTENTS *****

Prologue: The 2 Percent

1. A Committed Dude
2. Flight of the Needle
3. Silicon Valley for Socks
4. Bayard and Goliath

5. Heritage Land
6. The Sock Queen of Alabama
7. American Flannel
8. Resilience
9. New Lines
...

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