NEW YORK — Andrew Yang’s office phone rang at 6 p.m. on a Friday.
He reached for it, then stopped. The staffing coordinator at his New York law firm was calling. If he answered, he knew, he’d be at his desk all weekend editing some dull stack of documents.
It was fall of 1999, and Yang, 24, was in the job he had steered toward his whole life. Phillips Exeter Academy, Brown University, Columbia Law — the perfect elite track to land at Davis Polk & Wardwell, one of the country’s premier law firms. His Taiwanese immigrant parents were thrilled. Counting salary and bonus, he was making about $150,000 a year.
But now he looked at the phone, and the nagging whisper in his head was suddenly a screaming alarm: He was in the wrong job. He wanted to be the person creating businesses and deals, not the person writing the contracts.
He let the phone ring and slipped out the door.
That small act of rebellion was his first step toward becoming Andrew Yang, entrepreneur.
Two decades later, Yang’s norm-busting career as an Internet business builder is the foundation for his norm-busting Democratic presidential campaign. He evangelizes about what he’s learned creating start-ups and nurturing businesses focused on the public good. His marquee policy — giving every U.S. adult $1,000 a month in guaranteed income — is the most unorthodox proposal of any major candidate.
It’s the product of a nontraditional career, which began with his decision, in early 2000, to quit his law firm and walk away from all that money, prestige and comfort.
He frequently refers to his lawyer days as “the five worst months of my life.”
“Working at a law firm was like a pie-eating contest, and if you won, your prize was more pie,” Yang said in a recent interview on the Acela train from Washington to New York, between hurried bites of a turkey sandwich.
The law jokes play well, especially because seven of the 12 candidates in the last televised Democratic debate have law degrees.
But quitting law was not really about walking away from something. It was more about running toward something else that was calling to him with a sudden, urgent clarity.
“I thought, ‘Shouldn’t I be someone who builds something?’ ” he said. “That made more sense to me. But how do you get there? I figured there was no way to figure it out except to do it.”
So just before the start of the new millennium, Yang and another refugee from his law firm created an Internet start-up to help celebrities use their fame to raise money for charity.
It flopped. He went broke, lost his apartment, lost weight and confidence, and wondered (along with his worried parents) how he was going to pay off $110,000 in law school debt.
But Yang was remaking himself.
“I have no regrets about not picking up that phone,” he said.
Bookish and bullied
Yang, 44, is the son of parents who emigrated from Taiwan to the United States to attend grad school at the University of California at Berkeley. His father earned a PhD in physics, and his mother earned a master’s in statistics and is now an artist.
They moved to Schenectady, in Upstate New York, where Yang’s father accepted a job with General Electric then later worked for IBM. Yang was born on Jan. 13, 1975, and when he was 4, the family moved to Somers, N.Y., in Westchester County, then later to nearby Katonah.
One of few Asian kids in his town, he was bookish and bullied. He played Dungeons and Dragons, along with piano and tennis because his parents said colleges liked well-rounded students. His mother, Nancy Yang, recalled that Yang and his older brother, Lawrence, now a professor at New York University, played piano duets and regularly won local competitions.
His parents knew he was extremely bright but not especially motivated. They told him, “If you fail, it’s because you didn’t try hard enough.”
“Andy once said to me when he was little, ‘I really don’t care about the grades. But I know you like me to get A’s, so I get those A’s for you,’ ” his mother said.
His family prized education: In addition to his brother, his father, uncle and cousin also became professors.
“For first-generation immigrants, the security of a job is the most important thing,” Nancy Yang said. “And we believe you need a good education to have a good job.”
When he was 12, his parents sent him to the Center for Talented Youth, which Yang calls “nerd camp,” a summer program for academically gifted kids run by Johns Hopkins University. He spent the next five summers there.
To qualify, he had to take the SAT, which students normally take when applying to college. He said he scored 1220 out of 1600 — better than most U.S. high school seniors that year. He said Johns Hopkins officials were so fascinated by his high score that they asked him to take the test in each of the next three summers.
At 13, he scored 1310, he said. At 14, he scored more than 1400. At 15, he scored more than 1500. When he was applying for college, he said, he didn’t bother to take the SAT again because his score at 15 was good enough for even the most elite schools.
When he was in 10th grade, a fellow camper told him about Exeter, the elite boarding school in New Hampshire. Yang thought it sounded like a great ticket to college. His parents gladly paid the college-level tuition, which he said was about $17,000 a year at the time.
“It was something we hadn’t planned for,” his mother said. “But he told me, ‘I want to be the best among the best, and I could really be the best there.’ It was very difficult for me to say no.”
He felt like an odd fit at Exeter, long seen as a preppy conveyor belt of establishment children. In a class photo from the time, Yang slouches in the middle of a crowd of mostly white kids in blazers and ties. He’s wearing a floppy flannel shirt, his hands stuffed into the pockets of baggy jeans.
Exeter academics were rigorous, including classes on Saturdays. Yang made the U.S. national debate team and competed at the world championships in London.
He was accepted to Stanford University and Brown University and chose Brown because he preferred the East Coast and his brother was at nearby Wesleyan University. He cruised through majors in economics and political science and started looking for the next prestigious step.
He took the LSAT law school entrance exam and said he scored 178 out of 180 — in the top 1 percent. He became a double Ivy Leaguer when he was accepted at Columbia Law.
“I wanted to become a smart, successful guy, and law school seemed like a good way to go,” he said. “Getting another degree was going to happen sooner or later, so I thought I might as well do it now.”
Sophia Ruan Gushée, a close friend who met Yang at Brown and is also the daughter of Taiwanese immigrants, said Yang worked hard to please his parents.
“Everything he did was to check a box about what would make his parents happy,” she said. “That’s why he did these really conventional, really impressive things.”
Lawrence Wu, Yang’s Columbia roommate, said Yang was smart enough to get good grades without working very hard. He said they both saw joining one of New York’s “Big Law” firms as inevitable.
Top-tier firms recruit heavily at the big-name law schools. Wu said he and Yang were both interviewed and wined and dined, and “you just naturally wind up falling into the gravity of that.”
The big firms were all paying first-year associates $125,000 a year, plus bonuses could add tens of thousands of dollars more. Yang had borrowed almost $120,000 to pay for Columbia. So a Big Law salary was a smart way to “get some return on investment,” Wu said.
Wu and Yang both accepted offers from Davis Polk.
“It really weighed on him that he wanted to do something purposeful with his life,” Wu said. “He hadn’t thought it through at that time. I think he thought, I’ll try Big Law and get some return on investment. And go from there.”
‘Purposeless and empty’
Yang walked into Davis Polk at 450 Lexington Avenue in Manhattan in September 1999.
“He was pure energy,” said Steven J. Williams, a Columbia classmate who also went to work at Davis Polk. “He was full of excitement. And you knew there was not a chance in hell that he was going to stay being a corporate lawyer for more than 15 minutes.”
Williams, now a partner at Paul, Weiss, Rifkind, Wharton & Garrison, said, “There was too much he wanted to do. Too much he wanted to say.”
Yang was assigned to a small office that he shared with Jonathan Philips, a recent graduate of Yale Law. Philips said Davis Polk’s headquarters was elegant and “seductively cushy.” But he and Yang, the newest hires, shared a space with two desks and a window that looked out on a building next door.
They worked 80-plus-hour weeks reviewing documents and contracts, writing summaries for senior partners, running to the printer. They wore suits, ate meals in the firm’s cafeteria and played basketball to unwind.
Nancy Yang said her son was suddenly paying more for a tie than her husband paid for a suit.
“It felt very purposeless and empty,” Yang said. “I was looking out at New York and thinking, ‘Wow, is this why my parents came to this country?’ ”
Philips was recently married, his lawyer wife was pregnant, and he also had six-figure student debt. He also felt the pressure to stay on the safe and traditional track. But he said he and Yang constantly discussed whether the law firm was the right path for them.
Yang said he did a “test” with himself to see whether he was in it just for the money.
“I went to Bloomingdale’s and bought my family cashmere scarves and some other nice gifts. Then I brought them to them that weekend, and they seemed to like them,” he said. “And I thought: Is this enough for me to do a job I don’t like? Definitely not.”
He knew the work would become more interesting as he became more senior. He liked the firm and the people there. But he couldn’t shake the feeling that he ought to be building a company of his own.
“No one there had the life and career that I wanted for myself,” he said.
Yang said he went home for Thanksgiving and told his parents he was planning to quit.
“What are you going to do about your debt?” his mother asked.
“Let me handle it. You don’t need to worry about it,” he said.
The conversation ended there, but Yang knew why.
When he started wearing an earring for a high school play at age 15, his mother didn’t tell him how much she disliked it until he finally took it out two years later.
“I’ve learned over the years that if I hate something, I should just not talk about it, because if I do, you’re just going to be more attached to it,” she told him.
He said his parents “took that tack with my leaving the firm, too: ‘If we just don’t talk about it, maybe he’ll change his mind.’ ”
Yang remembers feeling bad because his parents had taken out a second mortgage to help pay for his education, and now they thought he was “all set” because he had a prestigious, high-paying job.
“My husband was not happy,” Nancy Yang said. “I had to calm him down. I was a little bit worried, too. But I feel kids have to make their own decisions.”
Broke and in debt
Late one night at the law firm, Philips tried out an idea on Yang.
Davis Polk supported many charitable causes, and tickets to star-studded charity galas were a perk of the job. Philips was amazed at how these black-tie events regularly raised hundreds of thousands of dollars for charities. But he was shocked to learn how much of that was going to the charities’ administration and overhead.
At the dawn of the Internet age, Philips had already started one company — a college admissions consulting firm — when he was in law school. He closed it down to join Davis Polk.
Now he had an idea for a better way to do celebrity charity: an online platform that would connect celebrities and their fans with the charitable causes they supported — with virtually no overhead.
He told Yang they should create a start-up to make it happen.
“Andrew just lit up,” Philips said.
It was the idea Yang had been searching for — his own company, with a strong element of public good.
They called it Stargiving, and they started working through sleepless nights trying to refine the idea. They explained it to the partners at Davis Polk, who agreed to offer pro bono legal support to get it off the ground.
Yang and Philips soon faced a brutal choice. Stay or leave. Safe or risky.
In February 2000, five months after he joined Davis Polk, Yang quit.
“I was determined to figure out how to become the kind of person and builder I wanted to be,” he said. “My parents hated it.”
Yang had about $10,000 in savings. Rent for his studio apartment was $1,600 a month. He owed $1,200 a month on his $110,000 in student debt.
He started working in a “shoe-box” office he and Philips had rented for Stargiving. They raised a little capital from friends. Philips quit the law firm a couple of months later; he and his wife were living on her salary.
Five months later, Yang was broke and maxing out his credit cards. He gave up his apartment and moved in with a high school friend.
He went to Los Angeles to meet with potential investors and stayed with his friend Gushée, now an author who writes about health issues, who said she felt terrible because Yang “seemed really, really poor. He was so thin.”
“I was thinking, ‘You’re nuts,’ ” she said. “But he was so excited and so determined. He just fell in love with this start-up idea, this dream.”
Gushée said she recognized how hard it was for Yang to disappoint his parents.
“Taiwanese immigrants are very risk averse,” she said. “They value financial security, and they want you to be a doctor or a lawyer. It’s not easy for an Asian man to walk away from that.”
Stargiving had some success for a while, then crashed as the tech bubble burst and was out of business by 2002. Yang moved on to other ventures — including a party-organizing business — with mixed success. He eventually ran a business school test-prep company that earned him “in the low millions” when it was sold in 2009 (and allowed him to pay off his student loans). In 2011, he founded Venture for America, a successful incubator for start-ups across the country that supports other entrepreneurs.
President Barack Obama named him a “Champion of Change” and a “Presidential Ambassador for Global Entrepreneurship.” Yang wrote a book about his experiences called, “Smart People Should Build Things.”
He said he doesn’t regret studying law, which made him more “structured and detail oriented.” On the other hand, he said, the cautious analysis taught in law school can get in the way of an entrepreneur who needs to make decisions quickly, often based more on instinct than data. He said he had to “unlearn” some of what his law professors taught him.
Yang is now a kinetic presence in the Democratic race, though he lags behind the front-runners in the polls. On the morning of his interview on the Acela, he had appeared at a climate forum at Georgetown University. When he was introduced, he hopped off the stage and sprinted along the front row, high-fiving the cheering students.
“Even though Stargiving bombed, it was still a very invigorating, energizing process,” he said on the train, posing for selfies with supporters who recognized him.
“It was a period of soul-searching,” he said. “It was easy to feel like a bit of a failure. You’re doing jobs that nobody understands. You’re not making as much money as your friends. But you have to try. It’s the only way anything worthwhile ever gets built.”