Andrew Yang has pitched himself to voters as an entrepreneurial problem solver on quest to save America from automation.Credit...Christopher Lee for The New York Times

MANCHESTER, N.H. — The Andrew Yang on the presidential debate stage, the one who spoke about the need for more women in leadership and the lack of racial diversity among top-tier Democratic candidates, was the same person they’d once worked for.

But for some of his former employees, it seemed almost impossible to believe how far he’d come since a moment a few years ago when he told everyone at his nonprofit about a horror movie he’d read about.

Mr. Yang had been struck by an article about the film, “The Babadook,” which was written and directed by a woman and explores themes of motherhood. Movies like “The Babadook,” he told his employees, were in short supply and thus filled a gap in the market. If only more women were given opportunities, he continued — echoing an argument he made publicly around the same time in a 2015 essay — they would identify different problems than men and similarly help address market demands with their endeavors.

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Members of the mostly female team recalled exchanging glances. To some, it felt as if Mr. Yang were discovering sexism for the first time and explaining it to them.

Seven former staff members, some of whom attended this talk, discussed the episode and other staff meetings in interviews with The New York Times, describing the conversations in general and the movie discussion in particular as emblematic of Mr. Yang’s behavior as a boss.

In his life before politics, they said they saw in Mr. Yang a man who was smart, had good ideas, was a persuasive speaker and was occasionally inspiring. But he sometimes stumbled in his dealings with gender and race, expressing what the former employees said were antiquated and unnerving views for a presidential candidate seeking the nomination from a Democratic Party that has been moving to the left.

On the campaign trail, Mr. Yang has pitched himself to voters as an entrepreneurial problem solver on a quest to save America from automation — a candidate with the ideas to ignite a movement and the business savvy to get things done. Yang supporters have flocked to him, they say, because he has one clear idea: universal basic income. And one clear message about who he is.

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He earned a spot at the debate Friday in New Hampshire mostly on the strength of his rapport with voters here. He arrived from Iowa apparently without any pledged delegates, and in the aftermath of that performance has fired members of his campaign staff. He has signaled repeatedly that the primary Tuesday is of paramount importance in terms of his campaign’s viability.

Regardless of the outcome, the sheer magnitude of what Mr. Yang has achieved seems to be dawning fully upon him. He broke down in tears last week at an event in Iowa as he observed that campaigning for the last two years had been “the journey of my life.” And speaking with voters in New Hampshire on Wednesday, he shared what he said he had been telling his two young boys in recent days: “Daddy’s got a big deadline on Tuesday.”

When the Democrats do eventually pick a nominee and reflect on this process, the rise and staying power of Mr. Yang in this race — outlasting some governors and senators, drawing money and interest far longer than most people expected him to — will offer a clear lesson: In a campaign of maximum anxiety and maximum field size, an outsider with a specific message and a fanciful promise of free money can stand out.

But what was lost in the novelty, his former employees say, was real scrutiny.

Some of his former employees see, in Mr. Yang’s unlikely staying power into the early 2020 nominating contests, not just an odd embrace of an outsider, but a casual disregard for allegations about how he treated women who worked for him. It is a collective shrug, they say, that they find all the more disconcerting given how explosive and relevant gender has become in the race.

At the same time, Mr. Yang’s cavalier use of racial stereotypes about Asian-Americans and what his former employees say is a surprising lack of attention to his record as a chief executive have also gnawed at those who say they watched their boss similarly fumble delicate topics and conversations for years.

Some of Mr. Yang’s former employees describe a jubilant, funny, thoughtful leader who gave high fives and fist pounds, and sought to keep the mood light — a man who resembles the candidate they see on the campaign trail. Mr. Yang does not drink alcohol, but he would buy the first round during company celebrations, they said. He took employees on ski trips and to sporting events. And he encouraged people to do well while holding them to account.

But even years after their time spent working for him, many other former employees still recall specific episodes that they say highlighted Mr. Yang’s shortcomings: several women allege that he treated them unfairly when it came to compensation and employment; he once offhandedly remarked that the nonprofit fellowship program, Venture for America, might simply not be the best fit for black applicants; he convinced his nonprofit to pay for his family to join him on a lengthy fund-raising trip to California that proved largely unsuccessful.

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Ten of his former employees said they harbored deep reservations about his leadership and decision making.

Many of the 20 people who worked for or closely with Mr. Yang who discussed their memories did so on the condition of anonymity, fearing reprisal from the entrepreneur, a negative impact on their work and social circles and virulent online harassment from his supporters, known as the “Yang Gang.”

In an interview, Mr. Yang said he was proud of what he and his teams accomplished over the years at what he called “goal-oriented, high-performing organizations.”

“I think that most people felt that my heart was in the right place,” he said, “even if I mis-stepped at various times.”

‘Ready to make a mark’

On the stump, Mr. Yang summarizes his early years in a matter of minutes: After graduating from Brown University, he went to law school, spent five months as an unhappy corporate lawyer and then co-founded a business that experienced a “mini rise and maximum fall.”

The business, Stargiving, had been designed to help celebrities raise money for their favorite charities and gave Mr. Yang experience pitching and interacting with stars about two decades before an eclectic group of actors — including Dave Chappelle, Donald Glover and Ken Jeong — would find their way into his presidential camp.

Mr. Yang then moved on to work at two more start-ups, but a job at a health care start up hit a dead end in 2005. Around that time Mr. Yang reconnected with Zeke Vanderhoek, the founder of the test-prep company then called Manhattan GMAT where Mr. Yang had previously written curricular materials and sometimes filled in as an instructor. Now Mr. Vanderhoek wanted to start a charter school — and he wanted Mr. Yang to take over the company. Mr. Yang agreed and began running it in 2006, at age 30.

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“I was charged up and ready to make a mark,” Mr. Yang wrote in his first book.

Several people who worked at the test-prep company described a close-knit office of about 15 full-time staff members and several other part-time employees. The atmosphere there was “loose” and “upbeat,” said Jeremy Shinewald, who worked almost daily with Mr. Yang at Manhattan Prep and later served on the board of Venture for America.

Four people who worked with Mr. Yang at the test-prep company said he was socially awkward and prone to overstepping boundaries. They variously recounted moments when he burst out laughing when someone discussed a tragic event or when he pressured employees to participate at company karaoke outings.

Chris Ryan, an executive director at Kaplan who worked at Manhattan Prep as a part-time instructor in 2003 and became full time in 2007, said he believed Mr. Yang’s efforts at team building were “earnest and well meaning.”

“He was like, ‘I’m going to do the goofy teacher role,’” Mr. Ryan said.

The company was sold to Kaplan in late 2009 for what Mr. Yang has said was the “low tens of millions.” After the transfer cleared, he described giving out checks to employees like “Asian Santa Claus” and realizing that he had just been minted a “34-year-old millionaire,” though it is not clear exactly how much he was worth at the time. (In financial disclosure forms filed last summer, Mr. Yang reported assets worth as much as$2.4 million.)

Having completed his work at the test-prep company, Mr. Yang began a new endeavor: Venture for America. The goal of the nonprofit was to create 100,000 jobs by 2025 in the underserved cities where the fellows that the organization selected and trained would work and start businesses.

Mr. Yang has since acknowledged that Venture for America, which continues to operate under different leadership, has fallen well short of its goal. But as a presidential candidate, he puts a positive spin on V.F.A.’s failure to hit the goal, saying it led him to investigate the root causes of job loss and discover the impact of automation.

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Many of Mr. Yang’s former employees said that he worked extremely hard alongside them and that in some cases, Mr. Yang and the people he worked with became personal friends.

Todd Nelson, who was part of the program’s first class of Venture for America fellows in 2012, and later worked for Mr. Yang as part of the organization, said his former boss maintained “high expectations” and praised his integrity. As Mr. Nelson was beginning to mull rabbinical school several years ago, he ran the idea by Mr. Yang, who he said was extremely supportive.

“I will trust him until the day I die,” Mr. Nelson said.

But several former Venture for America employees said there were moments when they questioned Mr. Yang’s judgment.

For example, multiple employees recalled a period in 2016 when he had the nonprofit pay for him, his family and their nanny to stay at an Airbnb in the Bay Area for about 10 weeks on the assumption that he would procure significant new sources of funding for Venture for America. Mr. Yang, they said, failed to generate anywhere close to the $500,000 he had hoped to solicit.

In an interview, Mr. Yang broadly confirmed that the episodes described by former employees took place.

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“I’m now a dad with two boys and so instead trying to lead the team out on a karaoke night, I try to run home and see my kids,” he said. “And that’s probably better for everyone, because it turns out a lot of people don’t want the boss around in their off hours.”

As for his trip to the Bay Area, he said: “We didn’t raise the money I was trying to raise, but it was certainly not for want of trying.”

Claims of gender discrimination

Mr. Yang’s support among men tends to outpace his support among women. And in recent months, claims of gender-based discrimination and harassment have surfaced among campaign volunteers, some of whom wrote a letter to Mr. Yang in which they warned of a “bro-culture problem.”

The Yang campaign said it was assessing the allegations, and would bring in an expert to conduct anti-harassment training.

Those developments have not surprised some of Mr. Yang’s former employees, who said Mr. Yang’s boorish behavior sometimes made him look and sound more like a fraternity brother than a chief executive. And indeed, there have been episodes on the trail that could be described that way.

In one of his books, Mr. Yang described nicknaming his pectorals “Lex” and “Rex” and in another he said he worked out “a little too much” in college. In an interview last fall, he specified that Rex is the right pectoral muscle and Lex is the left one. “Check it out, this is Rex still trying to talk,” he said, flexing the muscle.

At an office opening in December, Mr. Yang sprayed whipped cream into the open mouth of a man kneeling on the ground in front of him, remarking, “It’s just a joke” as he did it. Mr. Yang’s campaign manager sought to intervene moments later as the candidate repeated the stunt with a second person.

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These episodes have struck some as being somewhat at odds with the way Mr. Yang has framed himself as a progressive champion for women. He has won praise for highlighting the value of his wife’s work as a stay-at-home mother and speaking out in favor of paid family leave and closing the gender pay gap.

Ronit Pelman, who was one of Manhattan Prep’s first employees and became part of Mr. Yang’s leadership team there, said that while watching Mr. Yang on the trail, she has been struck by his genuine desire to pitch ideas that “are centered around fixing the world.”

She spoke glowingly about her time working for Mr. Yang years ago. When she was pregnant, she said, he figured out a way to allow her to work remotely from Florida after the birth of her first child.

“We were friends,” she added. “Andrew was the best.”

But not all of the women at Manhattan Prep felt that way. In September, a woman who worked for Mr. Yang there alleged that he had fired her because she had gotten married and he thought her work would suffer.

Mr. Yang and Mr. Vanderhoek have forcefully denied that Mr. Yang engaged in gender discrimination when he fired the employee, saying she was let go because of her job performance.

In an interview, the woman, Kimberly Watkins, said she was “not at all surprised” by what she said was Mr. Yang’s “knee-jerk” impulse to call her a liar.

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“There is no data that I was not executing my job properly,” she said. “He promoted me and I hit every revenue goal, every marker set out for me.”

In November, a second woman who worked at Manhattan Prep alleged that Mr. Yang had engaged in wrongful termination and discrimination when he let her go after multiple discussions about her pay not being in line with that of male colleagues doing commensurate work. Her recollection was broadly confirmed by documents and by a co-worker to whom she relayed conversations about the situation at the time.

At various points, she said Mr. Yang had acknowledged that her pay was inequitable, but refused to increase her salary.

In a statement, a spokesman for Mr. Yang’s campaign said: “Andrew Yang has had the unfortunate task of letting staff go who did not meet the organization’s standards. The information provided by the letter-writer does not reflect the reality of the situation.”

Tense talks about race

For months, Mr. Yang has drawn applause with this line: “The opposite of Donald Trump is an Asian man who likes math.” The son of Taiwanese immigrants, Mr. Yang is one of a small handful of Asian-American candidates ever to run for president.

As such, the way Mr. Yang has discussed race has been the subject of intense scrutiny. His embrace of stereotypes that perpetuate the model-minority myth about Asian-Americans was sharply criticized in the fall over a proclamation he made during a nationally televised debate: “I am Asian, so I know a lot of doctors.”

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Several former employees described being struck by the awkward and sometimes aloof way they said Mr. Yang talked about race. Venture for America had been forced to grapple with diversity and inclusion issues from the outset; the former employees said — and an analysis of information on the organization’s website confirms — that about 60 of the 100 people in the first two classes of fellows were white men, though over the years, the diversity of subsequent fellowship classes improved.

The employees spoke of a perennial tension around how strongly to prioritize diversity and inclusion when it came to selecting fellows. Five former V.F.A. employees recalled that as they were expressing concerns over black fellows’ struggles to procure job placements, Mr. Yang suggested offhandedly that the program might simply not be the best fit for black applicants — a remark that enraged some team members who say he later walked the remark back.

Some also said that Mr. Yang vacillated on whether to categorize Asian-Americans as people of color, an underrepresented minority or underprivileged minority, given that he said they were overrepresented in the start-up and tech worlds.

Mr. Yang confirmed the recollections of his former employees regarding the discussions about black fellows. He also confirmed that he had told his team it should not herald the diversity of its fellowship classes if the diversity amounted mostly to “a bunch of Asian-Americans who are overrepresented in the space.”

Speaking more generally on how to discuss the subject of identity in the workplace and on the campaign trail, Mr. Yang told The New York Times: “I do have very strong feelings and points of view on race. I understand my identity very acutely.”

“But,” he added, “I’m not sure if leading with that is necessarily the most helpful way to move any community forward.”

His identity now, he said in an interview after a long day of campaigning in New Hampshire on Thursday, has been shaped by the two years he has spent on the trail. He opens up more. He is not just about charts and figures.

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He said that people tell him that his run has made them think that better things are possible in this country. And they tell him it has made them think something else, too: “That people who aren’t career politicians can just decide to run for president.”

Stacey Stowe and Isabella Grullón Paz contributed reporting from New York. Kitty Bennett and Alain Delaquérière contributed research.