The day after the Great Blizzard of 2020 dropped a foot of snow on her farm in Bedford, New York, in December, Martha Stewart arose around 4 a.m., like she always does, jumped into her snowplow and got to work. The 79-year-old, who became America’s first self-made female billionaire when her company went public in 1999, has plenty of groundskeepers for her “hundred and fifty fucking acres”—as she once described her vast estate on her cheeky HGTV gardening show, Martha Knows Best—but she’s a gay icon for a reason: She. Will. Work. Plowing her own roads is just so very Martha: taking a problem, attacking it creatively, getting visible results, and, most importantly, doing it yourself.
“Oh, I love to snowplow,” says Stewart. “I was out there actually for three hours before I realized it was three hours, and I was semi-frozen to death. But it was fun.” She’s calling me from the farm, where she sometimes runs into her neighbor Ralph Lauren while they’re both horseback riding. It would be easy to hate blonde, rich, famous Martha Stewart the way people love to hate Gwyneth Paltrow—of whom Stewart said in 2014, “She just needs to be quiet. … If she were confident in her acting, she wouldn’t be trying to be Martha Stewart.” But then there’s the snowplowing, and the burlap curtains she made for her chicken coop, which, who knows if she made them herself, but we at least know that she knows how to do it. And there’s the endless dedication to improving people’s lives, by showing us how to get oil stains out of our clothes or reminding us that we deserve a delicious, easy cocktail (with dried cranberries and a sprig of rosemary!) at the end of the day. So she made a little money while doing it, who could blame her? As we face down a full year of hiding from the coronavirus and being at home, with plenty of time to start loathing our dinnerware or learning how to make sourdough, Stewart and all she stands for have never felt more relevant. Every day she is churning out videos and Instagram posts (not to mention magazine issues and TV shows) about recipes and home decor to get us through the doldrums. Then there is her hilariously self-aware yet also unaware personal Instagram, @marthastewart48, on which she posts photos of her grandkids (Jude and Truman), her Chows and Frenchies (Emperor Han and Empress Qin, and Bête Noire and Crème Brûlée), and occasional viral thirst traps, like the one in her pool in one of her many homes (this one in East Hampton) that she took by accident while trying to take a photo of a blue ceramic pot (“I thought I looked nice, so I just snapped the picture”).
Most people who tell you they’ve invented whole genres of things or were the “first” at anything are probably exaggerating. But with Stewart it’s generally true. She popularized beautifully photographed cookbooks and manuals for living well, of which she’s written 98, and created a lifestyle magazine centered around a single person and philosophy (Martha Stewart Living, which celebrated its 30th anniversary last year), which she then tied to an Emmy-winning TV show. She brought luxurious homewares at affordable prices to big-box stores before anyone else did, and she figured out how to sell those goods through her magazine and TV show in a synergistic (“I love that word”), self-sustaining model of content and commerce she likens to a solar system.
You can see Stewart’s influence every time you scroll through Instagram and spot an artfully lit photo of a frittata or a meticulously arranged tablescape, or in the raft of cooking and home-entertaining hosts who came after, from Ina Garten (six years younger than Martha) and Rachael Ray (“she’s more of an entertainer … than she is a teacher, like me,” Stewart once said), to the entire Food Network and anyone who’s ever posted a how-to video on YouTube. But whatever perfectionist, hardass reputation Stewart once had (owing in no small part to a pervasive sexism that always follows successful, decisive businesswomen) has faded as new generations have come to embrace the looser, wickedly funnier Martha Stewart who’s emerged in the last decade or so, post-prison (more on that later). The Martha who got up, against the advice of everyone she pays to advise her, as the most random guest at Comedy Central’s roast of Justin Bieber and unleashed a profane dunk on the various rappers in attendance, as well as Shaq.
“I love me some Martha. She smoke weed, drink wine, and speak her truth!” says Tiffany Haddish, who grew up watching Stewart on TV with her grandmother. Haddish finally met Stewart a few years ago, upon which she promptly asked what it was like in jail. Now Haddish e-mails Stewart for advice on everything from day trips and gardening, to how to create generational wealth (trademark your name) and negotiate a deal (be prepared to walk away). “Like, I know visually she’s a white woman, but she’s just a woman who has a lot of life experience,” says Haddish. “And she’s not stingy with her knowledge.”
Not to disappoint Haddish, but Stewart doesn’t smoke weed, even though that’s a common perception given her close friendship with Snoop Dogg, 30 years her junior and her costar on VH1’s delightful Martha & Snoop’s Potluck Party Challenge. “What do they call it? A contact high?” Stewart says. “That’s the extent of my getting high with Snoop, is secondhand smoke, which is pretty serious, by the way.”
Being around Snoop, though, did get Stewart interested in cannabis. And her laser-sharp instincts for pushing her brand forward were evident when Stewart launched her own CBD line this past fall, during the pandemic.
Stewart says she’ll leave THC to Snoop, who connected her with Canopy Growth, the Canada-based company making her line. But there’s room to introduce her audience of aspiring domestic gods and goddesses to the stress-relieving, non-psychoactive powers of CBD, which is derived from hemp. In a video on the Canopy site that looks just like one of her cooking shows, overlaid with soothing Muzak and touting Stewart as “the original influencer,” she explains, “as [Snoop] knows, I’m always on the lookout for what’s new and what works.” The line includes CBD oil drops and softgels, but the stars are clearly her Wellness Gummies, which Stewart says she based on the French confection pâte des fruits and can be bought in a colorful, gorgeously packaged, $64.99 sampler box with 15 distinct flavors, like quince, rhubarb, and calamondin.
“Boy, nobody has gummies that taste like that,” Stewart tells me, explaining that “you don’t get high off the gummies; you get relaxed.” Stewart claims she can take 20 at a time. Based on my own experience of trying to write this story while munching on her gummies for “research,” even three would feel like a tranquilizer. But it’s a bold move into a new market, and Stewart knows just the right way to package it.
“Martha’s not static,” says Kevin Sharkey, executive vice president of Martha Stewart Living Omnimedia, who’s been Stewart’s right-hand man for 26 years. “She taught me that legacy isn’t really a past-tense experience; it’s what she’s going to build tomorrow or in an hour or next week.”
A hustler from an early age, Stewart started working as a preteen in Nutley, New Jersey, babysitting for 50 cents an hour—“as much as I could possibly babysit,” she says, because she realized that once she put the kids to bed, she could do her homework and get paid for it until the parents got home. She’s rarely stopped working since, moving on, during her high school years, to modeling, for “not extra money, MO-NEY,” she says, laughing. She appeared in print ads and TV commercials, and even did magazine shoots at the collections in Paris.
Stewart attended Barnard College, where she studied European and architectural history. Protests had just begun against the Vietnam War, but Stewart was not a revolutionary. Instead she got married at 19 to Andrew Stewart, a student at Yale Law, and had her only child, daughter Alexis, four years later, in 1965. “Nobody does that anymore. Nobody! Isn’t that crazy?” she says. “It was so natural for me.… I don’t plot out things. I am a doer. Doers just take it all in stride.” Stewart had thought she’d become an architect, but with her then father-in-law’s encouragement, spent seven years as a stockbroker on Wall Street. She was the only woman at her firm, surrounded by young men under the age of 30. “We were the real thing. You saw the movie Wall Street?” she asks. “I lived it. I mean, every man on Wall Street was trying to get you. Every man was trying to touch you in the cab. We had martinis for lunch.” One broker she knew locked women in his apartment for kinky reasons, like that Kim Basinger erotic thriller 9 ½ Weeks. (“I adopted one of their cats because he wouldn’t let her go home to feed the cat,” she tells me. “So I got Magnolia.”) Stewart, though, “was a modest girl,” she says. “I did not fuck around, if you want to use that word.”
“Do you remember hot pants?” Stewart wants to know. Sort of? “You’re too young; You don’t know anything,” she says. Little, tiny short shorts “where you see plenty of leg and a little bit of your butt.” Stewart says she had two pairs in velvet, one dark brown and one a peachy shade, that she’d wear with an alligator belt and a tight sweater tucked in. “And I looked great in them,” she says. “We would sit with our feet up on our desks, and I had high-heeled shoes on or boots. And that’s what we wore to work.”
After modeling in her teens and 20s, and working on Wall Street in the ’60s and ’70s, Stewart isn’t much fazed by men’s behavior. If she were, she wouldn’t be where she is. Stewart says that getting ahead as a woman in business meant tolerating a certain amount of bad behavior. “You had to keep your cool and just do your thing, and brush them away.”
As with other successful, pioneering women in business who knew no other course than to “brush them away” and compartmentalize the misogyny, the Me Too movement has proved complicated for Stewart. “It has been really painful for me,” she says. “I’ve known almost every single one of the famous guys that has been accused and set aside. Some were certainly guilty of a lot of what was accused. But some were—it’s just their awful personalities. I am not going to mention their names, but I know those people very, very well, and you know the man just talks about sex during dinner. That doesn’t mean anything to me.” In 1971, she and Andy and Alexis, then five, moved to Connecticut. “I was living two very distinctly different lives,” Stewart says. “And the life of the homemaker was more interesting to me than the life on Wall Street.”
So Stewart quit and started a catering business. “The most difficult job ever,” she says. She was catering a lavish 1,200-person party for one of her husband’s book launches (Andy had become a publisher of art books) when he introduced her to another publisher and she pitched the idea for her first book, Entertaining, which came out in 1982. The concept—beautiful color photos and stories to go with the recipes—became not just the template for “every single cookbook” you see on the shelves these days, Stewart believes, but the foundation of her brand concept “to inform and inspire” American women.
Martha Stewart Living, which Stewart launched with Time Inc., would become an extension of that ethos and help create an entirely new category of home magazines. But by the time the first issue appeared, in 1990, Stewart’s own home life had come apart: In 1987, as she was preparing for the release of her fifth book, Martha Stewart Weddings, Andy left her. The couple divorced, and he later married a woman who had worked with Stewart as a consultant.
Living was successful, but seven years later, Stewart bought it back from Time Inc. for an undisclosed sum. “I just wrote the check myself,” she says, and in doing so regained control of her name. She then created Martha Stewart Living Omnimedia, a media and merchandising company, and launched a line of fluffy towels and linens with Kmart—a move so controversial that in 1997 it got her disinvited from a Connecticut country club. (“Because I was too downmarket,” Stewart says.) Now you can find Martha Stewart home goods at Home Depot and Staples and Wayfair.
A fall from grace can only happen if you’re already riding high, and in the early 2000s, Stewart was riding higher than most women in business ever get. For half a decade in the late ’90s and the early aughts, Ana Gasteyer impersonated Stewart on Saturday Night Live, giving out crafting tips in calm, dulcet tones while “suppressing the demons inside.” Gasteyer’s Topless Christmas Special sketch is a classic. If there was ever a measure of Stewart’s cultural clout at her peak, it was those sketches, to an audience who knew her well, playing with the hard edge that always leaks out in her instruction in the soft arts.
Then, in 2004, Stewart began serving a five-month sentence in a federal prison, followed by several months of home confinement and probation, after being convicted of conspiracy, obstruction of justice, and making false statements during an investigation of alleged insider trading. The prison detour could have devastated her reputation and business—and it did for a while—but it also opened her to a whole new set of fans, who respected Stewart for doing her time and refusing to name names.
During a more recent trial, in which rapper Tekashi 6ix9ine cooperated with federal prosecutors in exchange for a reduced sentence on racketeering charges, Snoop wrote this of Martha on his Instagram: “As we watch Tekashi 69 (or whatever his name is) snitch on EVERYBODY, I invite you all to remember Martha Stewart snitched on NOT ONE soul during her trial. Baby girl kept it 10 toes down and ate that prison sentence by herself, like the true baddie she is.” He concluded with a caption reading, “That’s my M.F. Home girl … solid as a rocc.” Stewart, as she always does, tried to make the best of the situation. She left prison wearing a gray poncho crocheted for her by another inmate, and the pattern immediately went flying around knitting circles. After David Spade impersonated her on Saturday Night Live, wearing the poncho, she invited him on her show. He wore the poncho, she wore the poncho, most people in the audience seemed to be wearing the poncho. Even one of her Chows was wearing the poncho.
“I knew I was strong going in and I was certainly stronger coming out,” Stewart says of the period. But she doesn’t want to talk about it. “It was a very serious happening in my life. I take it very seriously,” she says. “I’m not bitter about it, but … . My daughter knows all the problems that resulted because of that. There’s a lot.”
The experience, she’s said, is one of many things that helped her bond with Snoop Dogg, who had spent time in jail on drug charges in the early ’90s. “Yes, that [conviction] helped because people knew how crazy and unfair … all of that was,” she said on CBS’s Sunday Morning in a joint interview with the rapper in 2017. “And in Snoop’s world, it gave me the street cred I was lacking.” Nevertheless, there’s one thing Stewart wishes she could do over. “My only big regret that I can talk about is that Saturday Night Live asked me to host. My probation officer wouldn’t give me the time,” she says. “That really pissed me off, because I would have loved to have hosted Saturday Night Live. I’d like that on my résumé.”
Stewart had been in the process of designing a new headquarters in Manhattan for 150 employees last year when the world stopped. (She still produces tons of content but no longer owns Martha Stewart Living Omnimedia, which has been part of Marquee Brands since 2019.) Since March she has been operating her business from the farm, keeping her entire team on payroll (she says she’s proud to have had no layoffs), initially interacting in person with only three of them: her housekeeper, her driver, and her head gardener, Ryan McCallister, recognizable from her shows and Instagram. McCallister has taken on the additional role of setting up lighting for her Zoom calls. Now they’re up to 30 people on the farm, having essentially turned her home into a TV production studio. Stewart has a concierge doctor come by to do Covid tests twice a week (two people tested positive, and they quarantined away from the farm). Everyone practices social distancing, wears masks, and eats lunch in their cars.
Stewart says the key to harmony with 30 people working out of your (very large) house—but in any business really—is to never think you’re better than anyone else. Creative directors and housekeepers are “all on the same plane,“ she says. “There’s no hierarchy in my life. I will wash the floor if I have to wash the floor. I’ll take out the garbage if nobody else has taken out the garbage. The CEO should be available to everybody at all times, if possible.” Another rule of business: “You should be able to call anybody anytime, even on weekends,” Stewart says. She once called a new employee on a Sunday. He said he was taking a bath and couldn’t talk. “I knew I couldn’t work with that person. I just couldn’t,” she says. “If you can’t talk on a Sunday and you take umbrage that I’m calling you on a Sunday—you know, if you are a terribly religious person, I take that into consideration. But I knew this guy was not a terribly religious person. It’s exciting! Business is exciting. I want people to feel that way about business.”
Speaking of business, it’s booming for Stewart. Her gummies are a hit, and she’ll soon be launching an accompanying CBD skin-care line called 86 Elm after her childhood address. As our conversation winds down, Stewart says, “If you can get some life lessons out of what I’ve done or what I think I’ve done, that would be great.” A week later, she’d thought of one she wanted to impart. “I’ve said it so many times, but take your life into your own hands. Don’t let other people direct you. Know what you want. I really believe in that.”