When Graydon Carter started his digital newsletter, Air Mail, in 2019, the initial advertisers included Hermès, Ralph Lauren and Standard Industries.

The first two names on that list made perfect sense, given the worlds of Hollywood, celebrity and international society that Mr. Carter covered exhaustively while he was editor of Vanity Fair for 25 years — a mix he has since transported to Air Mail.

The third was a head scratcher. Standard Industries? It sounded like a shadowy multinational corporation in a James Bond film.

By 2021, Standard was not only an advertiser in Air Mail but also an investor in the publication. That year, while speaking to a reporter from Business Insider, Mr. Carter shed some light on his publication’s new benefactor. He described Standard as “a very glamorous roofing company.”

Over the past few years, Standard, described on its website as a “global industrial company,” has become a backer of several media start-ups in addition to Air Mail.

They include Pushkin Industries, the podcasting network co-founded by Malcolm Gladwell; Cabana, a lushly produced twice-yearly shelter magazine and e-commerce site; Spiegel & Grau, a book publisher established by two veteran Random House publishers; and Puck, a digital publication that covers wealth and power and has a profit-sharing arrangement with its writers.

A roofing business investing in buzzy media start-ups seemed curious, to say the least. But surprisingly, the connections between Standard and the media world — and the lost kingdom of Vanity Fair under Mr. Carter in particular — don’t end there.

Several former Vanity Fair staffers — what Mr. Carter, in an email, called the VF diaspora — have gone to work for Standard. They include Beth Kseniak, the magazine’s longtime communications director; Sara Switzer, a publicist; and Dan Gilmore, an articles editor and a former assistant to Mr. Carter.

Jon Kelly, a founder of Puck and another of Mr. Carter’s former assistants, even compared Standard to his former employer.

“The vibe of the office feels like Vanity Fair,” Mr. Kelly told The New Yorker last year when interviewed about his new media venture. “People are sharp and sophisticated. It’s just classy.”

How did a roofing company come to be a player in the media business and the next career step for high-achieving magazine veterans?

The answer, it seems, is as much about the aspirations and evolution of Standard as it is about the extinction of the type of career once offered by legacy print media.

More Than a Roofer

Standard Industries’ headquarters are in Midtown Manhattan, and the company is far more than a roofer. Its website says it operates in more than 80 countries and has about 20,000 employees. In 2021, Forbes ranked it the 46th largest private company in the United States.

The business dates to the early 1980s, when Samuel Heyman, a corporate raider, bought GAF Corporation, a manufacturer of roofing materials in New Jersey, and took the company private. GAF later became mired in asbestos-related lawsuits. When Mr. Heyman died unexpectedly in 2009, his sons-in-law, David Millstone and David Winter, who at the time were both 32 and already working for their father-in-law, took over the roofing company.

That same year “the Davids,” as they are referred to internally, founded Standard Industries as a holding company to build upon GAF and Winter Properties, a real estate company in New York started by Benjamin Winter Sr., Mr. Winter’s great-grandfather. The men have added subsidiaries, acquiring W.R. Grace, a chemicals company that has faced its own asbestos lawsuits; Braas Monier, a European roofing manufacturer; and Icopal, a Danish maker of high-end roofing products.

Mr. Millstone and Mr. Winter declined to comment for this article, through a spokesman. (The company also declined to speak on the record but provided background information to The Times.) According to several former employees and associates of Standard, the Davids have aspirations to shake up the humdrum business of roofing and to become technology-focused innovators and disrupters.

Mr. Millstone studied philosophy at Yale, where he rowed crew, and attended Harvard Law School. He is said to be a big fiction reader interested in issues of sustainability and social justice. He and his wife, Jennifer, live in Aspen, Colo., and are philanthropists for public service and Jewish causes.

Mr. Winter grew up in Rye, N.Y., and studied economics and political science at the University of Pennsylvania. He is the one who is most interested in media, associates say. Mr. Winter is divorced from Mr. Heyman’s daughter, Liz, and lives in Manhattan. He is on the boards of the Metropolitan Museum of Art, Carnegie Hall and Conservation International.

In a rare interview, Mr. Winter told Forbes in 2021 that he and Mr. Millstone aimed to “crack rooftop solar” and unseat Elon Musk and Tesla as the new kings of the green technology. Standard recently introduced solar roofing shingles that it said need only a nail gun to install. Another project involves making roofing materials that incorporate 5G technology.

While doing things that felt familiar to the core business, the Davids were also expanding Standard Investments, an investment arm they established, which now manages more than $4 billion. The majority of that money is invested in the public markets, in other industrial companies like Shell. But through Standard Investments, the Davids have also invested in businesses further afield, like MyForest Foods, which makes plant-based meat alternatives; Saildrone, which operates ocean drones for mapping and data; and the electric carmaker Rivian.

Given Standard’s early involvement in Air Mail and its many links to Vanity Fair, one might assume that Mr. Carter, 74, is the person who wooed the Davids to invest in his new media venture and then others.

But in an email from Italy, where he was on vacation with his family, Mr. Carter dispelled that idea. Asked if he made introductions to Mr. Kelly and others who received funding from Standard, or put in a good word for former employees who have gone to work there, Mr. Carter said, “Not at all.”

He said the person responsible for that was Hamilton South, a veteran public relations executive who has worked at Giorgio Armani and Ralph Lauren and later helped found (and eventually sold) HL Group, a communications and consulting agency with fashion and corporate clients.

“Hamilton was on the front lines in this,” Mr. Carter said. “He brought in Beth Kseniak to handle communications and, before you know it, the place was filled with the VF diaspora.”

Stylish and well connected, Mr. South, 59, is also a Vanity Fair alum. He was hired at the magazine in 1989 under the editor Tina Brown, and became one of the few staff members from that incarnation to earn Mr. Carter’s admiration and to stay on when he took over in 1992.

An Enticing Pitch

Mr. South came to Standard as chief of staff in September 2017; the company had previously been a client at HL Group. He has since become Standard’s vice chairman.

He counts Diane von Furstenberg and Barry Diller as close friends. He and his husband, Manuel Bellod Álvarez de Lorenzana, a retired investment banker, own multiple homes in the United States and Spain.

Several people echoed Mr. Carter’s account that it was Mr. South who acted as a consigliere to the Davids, helping to remake Standard’s corporate culture. That makeover was achieved, in large part, by importing the staff and culture that Mr. Carter had built at Vanity Fair, starting soon after he ended his reign as editor in late 2017 and was replaced by Radhika Jones.

In 2018, as part of companywide cost cutting at Condé Nast, which owns Vanity Fair, about 20 of its staff members were let go. Among them were longtime members of Mr. Carter’s inner circle, including Ms. Kseniak along with a deputy editor, Dana Brown. The mass firing, which happened on Feb. 14, has become known in Vanity Fair circles as “the St. Valentine’s Day Massacre.”

Many who lost their jobs had benefited from the largess of Condé Nast — and, to some extent, Mr. Carter — and were staring down uncertain professional lives after years on the mountaintop. Enter Mr. South, who began contacting former staff members with an enticing pitch to work at a company on the rise and at a salary significantly higher than their media jobs.

Mr. Brown, who worked at Vanity Fair for more than two decades, starting as Mr. Carter’s assistant in 1994, said that working there partly required you to be a polymath — to have “specific knowledge” of different industries and social scenes and to know “how the world works.” The job also involved being a living embodiment of the stylish world created by its top editors.

Now, according to Mr. South’s pitch, Standard needed culturally astute storytellers and worldbuilders. People who could burnish the reputation of a company with a subsidiary, Siplast, that worked on the roofs of notable buildings like the Metropolitan Museum of Art and Moynihan Train Hall.

Ms. Kseniak consulted initially and came aboard in late 2019. Already on staff was Harrison Vail, a member of her team at Vanity Fair whom Mr. South had contacted. Others, like Ms. Switzer and Mr. Gilmore, who is now chief of staff for Mr. Millstone, soon followed.

Mr. Vail is now back working for Mr. Carter as the communications director at Air Mail. Ms. Kseniak, Ms. Switzer, Mr. Gilmore and Mr. South, through a spokesman for Standard, declined to comment for this article.

Mr. Brown, 50, who chronicled his time at Vanity Fair in a memoir, “Dilettante,” was initially surprised when he heard some former colleagues were working for an industrial firm, he said, but he understood the appeal. By then, the golden age of magazine publishing was over, killed by the internet and social media, and the famously lavish budgets and salaries were vanishing.

“I tell you, if I had gotten a call from Standard Industries, offering me a job with a great salary and benefits, I would have been, like, ‘Screw it. I’m in the roofing business now,’” Mr. Brown said. (Some of his colleagues who left Vanity Fair did transition into jobs more similar to what they had been doing. Aimée Bell, a deputy editor, became a vice president at Gallery Books, a Simon & Schuster imprint. Krista Smith, the magazine’s executive West Coast editor, went to work for Netflix.)

Another former Vanity Fair staff member who heard Mr. South’s pitch was Lizzie Wolff, who also worked in communications with Ms. Kseniak and joined the digital newsletter theSkimm after Vanity Fair. Ms. Wolff, 40, said she was hesitant to make the switch from media.

“I worked at a place where we did the biggest party in the world,” she said, referring to the annual Vanity Fair Oscar party. “You can imagine me at a cocktail party. ‘Solar, investments, this and that.’”

But after speaking to the Davids, she added, “I remember thinking these were really engaged and engaging guys. They were interested in transforming their business, but also had ideas and an interesting vision.” As at Vanity Fair, Ms. Wolff worked with Ms. Knesiak at Standard. She left the company earlier this year to consult and raise her children.

In 2019, Standard started a webcast speaker series that treated employees in its trucking and roofing subsidiaries — and anyone who wanted to watch online — to events featuring “innovators and thought leaders” in conversation with Mr. Millstone and Mr. Winter. Participants included the author Jennifer Egan discussing curiosity and fiction and the TV host Seth Myers musing on fatherhood. Two Vanity Fair alumni, Matt Ullian and Jane Sarkin, who now run an events company, Boldface Partners, were hired to wrangle some guests.

At the same time, Ms. Kseniak and her team of former Vanity Fair staff members sought interesting stories within Standard’s many businesses to pitch to mainstream media outlets like Forbes to raise the company’s profile.

The team also had to develop relationships with people from the roofing industry and trade publications, which sometimes made for fish-out-of-water moments.

In 2020, Mr. Vail found himself in Dallas to attend the International Roofing Expo. At Vanity Fair, he had also traveled for work — to the South of France, for the Cannes Film Festival.

Building a Media Portfolio

As Mr. South helped remake Standard’s corporate culture in the image of Vanity Fair’s, he also leveraged his connections to bring the Davids opportunities to invest in media — an industry that, though diminished, still had a certain pizazz and power associated with it. (Consider Jeff Bezos and other billionaires who have bought media companies — or Mr. Carter, who left Vanity Fair only to return to media.)

Jacob Weisberg, the former editor of Slate and a founder of Pushkin, which produces such podcasts as “Broken Record” and “Revisionist History,” said he has known Mr. South since his early days working in media. He said that relationship was ultimately how Pushkin’s pitch deck ended up with the Davids in late 2018.

Mr. Kelly has known Mr. South since he was an assistant at Vanity Fair. Mr. South invited him to meet the Davids in May 2018 and, not long after, Mr. Kelly contacted Mr. South to see if Standard wanted to invest in the business that became Puck.

Julie Grau and Cindy Spiegel used to work with Mr. South’s sister, Mary South, at Riverhead Books. In early 2021, the women pitched to Standard their idea for a “content-forward, format-agnostic” publisher that would take a boutique approach to releasing books, as well as create original podcasts and audiobooks.

“We spoke to David Millstone and he communicated very clearly that he believed in what we were doing and that he wanted to support it,” Ms. Grau said.

As for Mr. Carter, he was having dinner with Mr. South in 2021 after completing the initial funding round for Air Mail. Mr. South “mentioned that if we went out for another round,” Standard would be interested, Mr. Carter said in an email.

The media investments represent a tiny fraction of Standard’s portfolio — about $25 million of the investment arm. But they seem to hold a sizable interest for Mr. Millstone and Mr. Winter, who recently made another investment in Puck.

“He’s not there for the wrong reasons,” Mr. Weisberg said of Mr. Winter, who sits on Pushkin’s board, and is a board observer at Puck. “He’s there to learn and because it’s interesting. He gets it. He’s truly curious about how media works.”

In 2020, Standard moved offices, into the space that Mr. Kelly likened to Vanity Fair’s glamorous offices back in the golden days.

The company, which needed more space for staff, relocated from the 30th floor of the Solow Building on West 57th Street, where tenants include Chanel and Apollo Global Management, to the 46th and 47th floors.

The newly designed, open-plan office, which Standard declined to show to The Times in person, features light wood floors, artwork by Ed Ruscha and views of Midtown and Central Park.

“Quiet luxury, as they say these days,” Mr. Carter said of Standard’s headquarters.

Vanity Fair has also moved offices.

In another cost-cutting move, Condé Nast reduced its 1.2 million square feet of office space at One World Trade Center and subleased several floors. As a result, Vanity Fair relocated from a floor-through space on the building’s 40th floor down to the 25th floor, where the staff is now squeezed together with the staffs of Vogue, GQ, Glamour, Self, Allure and other titles.