The tech world's quiet connector

Story by Melia Russell
Photography by Lelanie Foster

Ruzwana Bashir is ransacking her kitchen cabinet for just the right tea. On this fall day in Manhattan, the 40-year-old CEO of Peek, an activities-booking company, looks chic and comfortable in black trousers and a wool turtleneck. She's offered to make tea, and when I tell her I like fruity and black, she seems enthusiastic about the challenge. She's sorting through stacks of tins like it's the most important thing she'll do all day.

While she's distracted, I take in her SoHo apartment. A large white sectional wraps around a coffee table laden with candles, fresh roses and ranunculus, and books on Andy Warhol, Picasso, and the Byzantine empire. In a sun-drenched corner, an ecstatic fiddle-leaf fig reaches toward the 13-foot ceiling. Below it, a dining table has two laptops and a stack of notebooks at one end.

A minute later Bashir retrieves a container of Mariage Frères loose-leaf tea with blue-cornflower petals, sniffs it, and places it on the counter, satisfied.

Being a host is kind of like being a CEO, she says, drawing hot water from an espresso machine. She feels responsible, in both her personal and professional life, for bringing out the best in people, plying them with the right role or the right loose leaf. "Part of your job is to help people find the seat they should be in," she says.

I'm at Bashir's home in part to talk about her company, which, despite my eight years of reporting on startups, I had to Google. Though its name barely registers with laypeople, Peek, which started as a kind of OpenTable for travelers and pivoted to providing software to tour companies and operators, is now basically the Salesforce of tourism.

Each year, about $1 billion worth of ticket sales — a seaplane tour over the Golden Gate Bridge, a visit to the Museum of Ice Cream, a swim with pigs in the Bahamas — goes through the company's platform. This past spring, the venture-capital powerhouse Andreessen Horowitz declared Peek the 14th-largest virtual marketplace for goods and services in the United States. The company has raised $120 million from the likes of Jack Dorsey, Eric Schmidt, and Goldman Sachs. All of which makes Peek's (and Bashir's) near-anonymity more remarkable. In an industry where success is often measured by how much noise a startup makes, Peek has proved it doesn't need the limelight to commandeer an industry.

Even so, I feel dazzled being with Bashir, not least because her apartment has enough fine art to charge admission. She speaks in a lilting British accent and has wide silver-green eyes like eucalyptus leaves. She's a careful listener, leaning in when I offer my observations on the new status shoe for techies (Allbirds are out, Hokas are in. Though Bashir seems to prefer Chloé's Nama sneakers.)

Like her company, Bashir isn't a household name; rather, knowledge of her is passed around in the types of circles that would make the illuminati jealous. She's a conduit for ideas and connection, hobnobbing with tech gods and artificial-intelligence researchers, as well as fashion icons, Hollywood directors, economists, and media moguls. She's played Connect Four with Elon Musk, brunched at Balthazar with the investigative journalist Ronan Farrow, and posed for the September issue of Vogue.

She references her network throughout our two-hour conversation. For three years she's been learning to invest from Roelof Botha, a senior steward of Sequoia Capital's brand and operations. "Mustafa Suleyman sat here," she says at one point, patting the Google DeepMind cofounder's preferred couch cushion, "and we've had conversations about what's going to happen with AI but also what's going to happen in the world."

Bennett Miller, a close friend of Bashir's known for directing films like "Moneyball" and "Capote," says they often watch movies together. In describing Bashir, he references a bit in "The Big Lebowski" in which The Dude bemoans the destruction of an area rug. "There's a line about the rug — how it really tied the room together," Miller says. "Ruzwana is that rug."

I can feel Bashir's penchant for forging connections as she focuses in on me, making me feel like the most important person — and the most discerning tea drinker — alive. ("If it's not strong enough, let me know," she says of the tea. "I can add some more.") She doesn't just host, doesn't just lead; she creates little universes where nothing existed before.

Bashir has built a career connecting people to new experiences. She grew up in a Muslim household in northern England, where she wore a shalwar kameez and a head scarf every day. Her parents didn't read or write in English, and her father sold produce to provide for his wife and their three children.

After high school, Bashir attended Oxford University and became president of the Oxford Union, the famed debate society, where she welcomed speakers such as Madeleine Albright and Tom Ford. Her love of travel bloomed in school. Jared Cohen, a partner at Goldman Sachs and a college friend, recalls studying for exams with Bashir at an Egyptian resort they booked on a budget travel website. Her idea of a study break: waking up early to drive across Israel and visit the ancient city of Petra.

After college Bashir jumped to Goldman Sachs and then to the Blackstone Group, but in 2011, while studying at Harvard Business School, she caught the entrepreneurial bug.

The idea for Peek came to her after she spent 20-plus hours looking up things to do on a birthday trip to Istanbul. There had to be a better way to book activities online, she thought. And so, with the help of an engineering virtuoso named Oskar Bruening, she built one. They launched Peek in the fall of 2012.

Suddenly, Peek was just about everywhere (though not for those of us who were broke college students at the time). So was Bashir: on Forbes' "30 Under 30" list alongside Mark Zuckerberg; in billboard ads for the luggage brand Tumi; in Elle, where she was described as "one of the hardest-working (and chicest) women in tech." It was the age of the Ubers, the Airbnbs, the WeWorks — a moment when "disruptors" were treated with near-total credulity. "This idea of software eating the world was just starting," Bashir says. "It was a moment where people suddenly realized this incredible value creation happening in tech."

The cult of personality that rose up around Bashir wasn't unusual; founders like Travis Kalanick and Adam Neumann were just as inextricable from their brands. But the line can be blurrier for women, especially if they lead consumer companies, which rely on branding to set themselves apart. Ty Haney's bubbly personality helped position Outdoor Voices as the cool-girl queen of the activewear market. Emily Weiss amassed legions of fans through her beauty blog and online presence before launching Glossier.

"Part of building a business was going out and sharing what you were doing with the world," Bashir says. But she says she didn't think much about how her personality melded with her brand. "The only thing that I've always tried to be is authentically myself," she says. "Sometimes that means that you're not fitting into people's stereotypes or the box that they're expecting. And that's OK. Hopefully, we're finding ways to expand that box."

At first, Bashir's team at Peek focused on bringing experiences directly to people. But they soon learned where the real potential lay. "There's an opportunity to help people book experiences, but in some ways it's quite a narrow one," Bashir tells me. "The bigger opportunity is to unlock everything and bring it all online."

In 2013, Peek started putting resources into software to allow travel companies to enable purchases on their own websites and track their reservations — a move that turned out to be the company's saving grace. In 2016, Peek capped hundreds of millions of dollars in annual bookings and opened a second office in Utah. By 2019, downloads of the Peek app, which had spiked at more than 30,000 in December 2013, had dwindled to a few dozen, according to the analytics company Data.ai.

But even as downloads cratered, bookings were mounting. By then, Peek had gone all in on its software sales. "As a startup you have to be extremely intentional about where you put your resources," Bashir says. "When you're seeing success you have to back that horse." Bashir refashioned her startup to meet the needs of an industry that still operated using pen and paper and, in doing so, earned a second shot at overseeing a business worth billions.

Just as Peek got back on its feet, COVID-19 knocked it all the way down. People were terrified and trapped in their houses, and travel bookings fell to nearly zero overnight.

On March 13, 2020, President Donald Trump declared a national emergency, and Bashir caught a flight to Salt Lake City. She and Bruening were on their way to Utah to lay off almost a third of their staff in person. They hoped such a drastic step would get them to the other side of lockdown. "That's the hard part of being a founder," Bashir says. "You have to make tough decisions and then also live with the consequences."

To the delight of investors, Peek rebounded with dizzying speed. During the pandemic, digitization flourished as much of the world moved online. Suddenly a small-business owner with a zip-line park in Costa Rica or a pub-crawl party bike in Atlanta needed software to help them market, process sales, schedule guides, and send emails. For years Bashir's startup had been building muscle around these capabilities; now it had an eager audience.

In 2021, Peek crossed $2 billion in all-time bookings from some 35 million customers. It also landed $80 million in Series C funding from investors including the former Airbnb chief financial officer Laurence Tosi's firm, WestCap. Those who know Bashir say things wouldn't have turned out any other way. "She's not a despairing person," Miller says. "There's a determination there that I would bet on 10 out of 10 times."

"I need wind," Bashir says as a canvas parachute whips around her.

She's standing on the set of her photo shoot at Chelsea's Pier59 Studios in a black bustier dress, metallic pumps, and a red lip. Like Beyoncé asking her team to please for the love of god turn on the fan, Bashir gestures for the hairstylist, who's holding a leaf blower, to come closer.

Through hundreds of interviews, I've grown familiar enough with the trope of the misfit founder to know there's some truth to it. But from where I'm standing, that person is not Bashir. At one point she huddles around a monitor, watching images of herself flit across the screen. She takes a swig of tea and wags a pale-polished finger at a photo she likes.

I ask if she's fazed by the glamor. She shrugs and launches into a story about how, on the set of her Vogue photo shoot, she rejected a wardrobe selection from Anna Wintour.

"Can you say no to Anna?" someone asks.

"I'm not scared of Anna," Bashir replies — though maybe she is, just a little, because she turns to me to ask if we're off the record.

Bashir is the rare entrepreneur who can traverse the cultural zeitgeist, leaping from generative art to the Human Genome Project to Taylor Swift. (Though she's not a Swiftie, her role on the SoFi board ties her to the "Eras Tour" movie, which is set at the company's stadium.) "I've rarely come across so many superpowers in one person," says the investor Katie Haun, who met Bashir at a conference. She says Bashir struck her as a "deep thinker across many disciplines."

Miller met Bashir 11 years ago at a different conference, fresh off her company's founding. "You have every different type of person, and at the center of it was Ruzwana, probably the youngest person there," he says. "By the end, it felt like the entire conference was orbiting around her."

"I just think she's attractive, and I don't mean that in the superficial sense," he adds. "She's generous in her enthusiasm, her spirit, her optimism, her humor. They burn bright and colorfully."

A few years ago Bashir attended a leadership summit in the mountains where, after a day of discussions, she wandered into a room with board games. She sat down to play Connect Four across from Elon Musk. A crowd formed around them, and things got intense. She won, 3-1. "It was great to take the victory," she says. "He has space; I have Connect Four."

She also has a standing invitation to Silicon Valley's most exclusive, semisecret dinner party. Each month, tech's biggest power players — Marc Benioff, Reid Hoffman, Marissa Mayer, Dick Costolo — gather for a Jeffersonian dinner where the conversation ranges from all-knowing artificial intelligence, or AGI, to their industry's impact on geopolitics. Eating at acclaimed restaurants is fine, but Bashir prefers the more-intimate affairs at tech executives' homes because, she says, "you can stay longer." The dinners have the feel of a cool kids' gathering at a hometown bar the night before Thanksgiving — an ease that comes from decades of friendship.

This supper club's guest list has the power to affect policy, inspire innovation, and even shape our digital destiny. Bashir has been attending when she can for several years. "The goal for all of us is to shape our thinking so that we can be purposeful with it," she says. It's this kind of intention that defines Bashir's life, says Cohen, more than any material success. "There are people who take a piece of paper and chart out their path to achieving greatness by the age of whatever," he says. "Then there are people who view ambition through the lens of having a good and meaningful life and measuring impact by what that looks like day to day. And she's much more in that latter category."

Katherine Maher, the CEO of Web Summit, has gone to one such dinner as Bashir's guest. The two met seven years ago as members of the Young Presidents' Organization, an elite social group for business leaders. Maher wanted to attend the organization's retreat, but she couldn't afford it at the time. So Bashir offered to split a hotel room. They bonded over art, book recommendations, travel stories. "Both of us felt like being CEOs of technology platforms weren't the only interests in our lives," Maher says.

The dinners scratch a familiar itch for the startup maven whose curiosity needs constant feeding. It's her reason for traveling — she visited more than 40 countries before turning 30 — and seeking out friends in such disparate fields. She points to one, Daniel Kahneman, a behavioral psychologist who won the Nobel prize in economics. It's not unusual, Bashir says, for laureates to take home prizes in fields where they're not experts. "They have understanding," she says. "But then, they are not beholden to the rules."

At the dinner, Maher noticed that when Bashir spoke, the table listened. "She has this way of reminding people of their core value, as opposed to the value that the world projects on them," Maher says. "She's got everyone's trust."

Credits

Writer: Melia Russell
Photography: Lelanie Foster
Creative Direction: Liane Radel
Styling: Becky Akinyode
Prop Styling: Elaine Winter
Hair: Yukiko Tajima
Makeup: Ayaka Nihei
Production: Tiffany Bloomfield for Dela Revoluciøn
Photography Assistance: Chad Hilliard, Enmi Yang
Digital Tech: Kenny Aquiles Ulloa
Styling Assistance: Cyrenae Tademy, Madison Perez
Prop Styling Assistance: Aidan Lapp, Bashira Webb
Tailoring: Zunyda for Stitched Tailors Agency
Design and Development: Bryan Erickson, Jinyoung Chang-Rodriguez, Rebecca Zisser
Editing: Claire Landsbaum, Emma LeGault, Joi-Marie McKenzie
Editing Assistance: Brea Cubit
Video: Conner Blake, Kyle Desiderio
Social: Victoria Gracie, Nicole Forero, Virginia Alves