50 Most Daring Entrepreneurs

Entrepreneurs
November 2, 2017

50 Most Daring Entrepreneurs

The most inspiring, insightful, and inventive risk takers of 2017.

Entrepreneur

Entrepreneurship is about taking the right risks. In the following slides, we spotlight 50 entrepreneurs who took a leap in the past year–and who can inspire us all.

50 Most Daring Entrepreneurs

1. Alex Bellos

West Elm

West Elm

Breaking out of a comfortably furnished comfort zone

“When you enter a furniture store, the company hopes you sit and stay a while. Now West Elm is betting on it. The Brooklyn-based home furnishings retailer, whose stores are beloved for their pristine styling of sophisticated but inviting furniture and accessories, announced last fall that it’s making a push into the world of hospitality and will debut West Elm Hotels in 2019. Six locations are in development and will result in boutique experiences in which guests will have the opportunity to purchase the furnishings and accessories that surround them.

West Elm, like many furniture retailers, is losing market share to online startups like Wayfair. Company president Alex Bellos knew it needed to create new opportunities that could do what no online retailer could, namely let the customer live with the furniture before buying. “Our stores’ environment and styling are designed to help customers imagine and express their personal style at home,” he says. “The hotels will offer a deeper experience as guests and the community make each property feel like their own.”

The opportunity is bigger than just an ultimate showroom, Bellos says. He believes West Elm has spotted a meaningful gap in the hotel market. By creating homey stays in underserved business hubs like Detroit and Minneapolis, the company is moving into fertile Airbnb territory. Instead of extolling thread counts or rug weaves, its marketing materials gush about “communal spaces” and “community connections.” And with the hotels overseen by DDK, a management company formed by alums of trailblazing Andre Balazs Properties and Ian Schrager Hotels, the accent is firmly on the guest experience. Staff members, who will soon be put through their paces at the West Elm Academy, will be chosen for their conviviality.”

50 Most Daring Entrepreneurs

2. Jeff Bezos

Chrisopher Patey/Getty Images

Amazon

Never stopping, and never being predictable

Jeff Bezos started Amazon 23 years ago as an online bookstore. Today it has grown into the largest internet retailer in the world; it’s home to an Oscar-and Emmy-winning production studio; its subscription service, Amazon Prime, reached 80 million members this year (up from 58 million in 2016); and it’s made Bezos one of the richest men on the planet. This success alone—to see opportunities where others haven’t, and move into them faster than others can—would make him a daring entrepreneur. But alongside that, Bezos has proven himself adept at taking on totally unexpected challenges.

In June, Bezos snapped up organicgrocery purveyor Whole Foods for $13.4 billion and quickly slashed prices (though the full scale of his plans have yet to be revealed). His stewardship of the Washington Post, which he bought in 2013, has become the envy of the media business: Its ad revenue grows double digits each year, traffic has surged and broke the 90-million-monthly-user mark this year, and it’s building technology that other media outlets can now pay it for (like Zeus, which delivers ads at light speed; Heliograf, the PostÕs automated storytelling system; and Clavis, its content recommendation engine). In sum, Bezos doesn’t just buy a company— he uses it to rethink an industry.

To understand how his impact spreads beyond the walls of his own operation, we asked four Amazon alumni—all of whom now head up their own companies—to look back on the priceless lessons they learned from the boldest man they know. — J.J. McCorvey

What four entrepreneurs learned from working side by side with Jeff Bezos.

Lesson 1

Don’t worry about the money.

“My first year at Amazon, I was in charge of ‘space management,’ which meant overseeing how the storage was used in our warehouses. I made a mistake and placed too much product at the very top of our shelves, and when orders came in, workers couldn’t bring items down fast enough to fulfill them. It was a massive mistake, so I presented Jeff with a plan to save us money [while canceling the least number of orders]. I was proud of myself— I thought I was saving the situation. He looked at me and said, ‘Stop. Don’t worry about the money. Ship everything you can as fast as you can; don’t miss a single order. Figure out how much it cost us, and make sure it doesn’t happen again.’ Don’t worry about the money? Most companies claim the customer is the most important thing, but they’ll do what’s right for the company. For Jeff, it’s genuinely what’s right for the customer.”

—Nadia Shouraboura,

founder and CEO, Hointer

Lesson 2

Forget the output, and focus on input.

“When you look at how Jeff Bezos interacts with Wall Street, he says, ‘Look, I don’t care about revenues and profits. If you want to hold me accountable for revenues and profits, then Amazon is not the stock you should be buying.’ Instead, he focuses on the inputs: how new initiatives integrate with Amazon Prime, the number of U.S. households he delivers to, the number of warehouses he’s built. If you look at scriptures and mythologies, many of them talk about warriors doing their duty and not worrying about the outcome. It’s a very powerful concept, being at the top of your game with the things you can control and not worrying about what’s out of your control. I’ve talked to maybe 50 CEOs in the past year during sales meetings, and it unsettles me how the majority of them are so emphatic about growth and revenue or profit but don’t think too much about the inputs it takes to achieve these things.”

—Guru Hariharan, founder

and CEO, Boomerang Commerce

Lesson 3

Be a leader, not just a decider.

“Back in 2003, I was one of a handful of people who got the chance to start Amazon Web Services, which [provides cloud-computing applications and] today is a very large business. I was tasked with figuring out how to monetize Web Services, and I got to work fairly closely with Jeff. About a year in, my team had an idea for a loyalty program. Our CIO, Rick Dalzell, set up a meeting with Jeff, who said that it wasn’t a good idea for Amazon. As meek as I was, I actually asked him, ‘Can you explain why?’ He could have easily dismissed me, but he very patiently and articulately described why our idea wasn’t good for the company but would be good for other businesses implementing loyalty programs at the time. I took away two very big things. One was the clarity of thought I saw from Jeff. It forced me to think—and that’s the kind of clarity of thought I aspire to. Second, it strengthened my belief in him as a leader, because he used the moment to educate me.”

—Vikas Gupta, cofounder

and CEO, Wonder Workshop

Lesson 4

Even as you grow, find ways to stay small.

“If I were to summarize the gist of what it’s like having Jeff Bezos as the leader of the company, it would be ‘Think big.’ Amazon’s internal slogan actually became ‘Work hard, have fun, make history.’ Come with big ideas, but be thorough in how we can achieve them. The key is to keep everyone focused on the needs of the customer. And the way you do that is to organize your workforce into small teams that are close to the customers. In the early days of Amazon Web Services, my team was very focused on customers who wanted payments, while other teams were focused on customers who needed storage. That notion of small teams, to maintain a tightness with customers, was alive even within the bigger team that was AWS. At [cloud communications platform] Twilio, we’ve adapted this as ‘Wear the customers’ shoes.’ Everywhere you walk in our offices, you see actual shoes sent in from our clients. It’s a constant reminder of how to succeed.”

—Jeff Lawson, cofounder

and CEO, Twilio

50 Most Daring Entrepreneurs

3. Bill Brown

New Energy Technology [NET] Power

Fighting global warming with an energy plant

“This December, NET Power will conduct a test of interest to energy companies and environmentalists. It’s the first effort of NET’s 50-megawatt natural gas plant, which aims to capture almost all the carbon dioxide it produces—for about the same cost as a standard plant. Where most carbon-capture processes modify existing steam-powered plants, NET Power’s technology uses high-pressure, superheated CO2 instead of steam as the working fluid. “Everybody told us we were crazy,” says Brown, an ex–Wall Streeter who teamed up with Miles Palmer, a pal from MIT, to form NET Power’s parent company, 8 Rivers Capital. “But we’ll allow the world to meet any climate target it chooses without paying more for electricity.””

50 Most Daring Entrepreneurs

4. Perrin Chiles

Adaptive Studios

Turning unloved film scripts into fresh revenue

Every day in Hollywood, scripts are bought, only to be abandoned at the expense of considerable money and time. That’s where Adaptive Studios sees opportunity. It buys abandoned properties cheap and converts them into fresh content across several platforms. The four-year-old studio saw big payoffs in 2017. For example, it took a discarded script, turned it into a book to generate buzz, and then adapted that into a Netflix movie, Coin Heist. TV and film make up 60 percent of the (profitable) business, but the real growth is in video, “which is really exciting,” says CEO Perrin Chiles. “We want to be the Sundance for the next generation of storytellers.”

50 Most Daring Entrepreneurs

5. David Cohn

Paul Body

Cohn Restaurant Group

Competing against himself—with a nonprofit

David Cohn’s philosophy: A rising tide raises all boats, and more consumer options buoy bottom lines. Unlike many restaurateurs, who scatter locations to spread risk, Cohn clusters many of his two dozen California eateries. He thinks a vibrant dining scene attracts more eaters. For his most recent space in San Diego—in front of his speakeasy and next to his California-French restaurant—he decided to try something even more daring. In May, he opened a taco shop called Libertad that donates all profit to local charities. (A monthlong event in September benefited Hurricane Harvey relief efforts.) And yet, he says, even this feel-good venture betters his for-profit businesses. “People take a break from the speakeasy to grab tacos rather than go elsewhere,” he says. “The synergy is working.”

50 Most Daring Entrepreneurs

6. Catherine Cook Connelly

The Meet Group

Broadcasting a love life

The Meet Group owns four dating apps—its largest is MeetMe—and serves 2.7 million active users a day. But each user visit was averaging about a minute. Could the apps do better? Catherine Cook Connelly thought so. In March, her company launched a live broadcast feature, alerting users if someone popular or new who may be interesting to them is about to go live. It blew up. Now 22 percent of MeetMe users watch for an average of 20 minutes a day. A survey even found that 65 percent of broadcasters feel more attractive afterward. “They’re just getting tons of compliments,” she says.

50 Most Daring Entrepreneurs

7. Tom Cridland

Tom Cridland

Doing PR very, very differently

“When England withdrew from the European Union, British designer Tom Cridland got nervous. His company sells sustainable clothing that he guarantees for 30 years, and since 2014 it has grown into a buzzy label that generates more than £2 million ($2.5 million) annually. But when Brexit weakened the pound, Cridland needed to expand to survive and looked to the U.S. market.

To get his name out there, he didn’t turn to a PR firm—he’d looked into it before and was shocked at the outrageous fees. Instead, over the past two years, he mastered the art of his own PR (he even launched a side hustle, Tom Cridland Public Relations, to help others earn press at discounted rates).

Cridland decided to drum up publicity stateside in an old-fashioned, DIY kind of way: the road trip. In April, he and his business partner and girlfriend, Debs Marx, traveled here, jumped into a rental car, and embarked on a 22-city media tour that meandered from Boston to Las Vegas. Before each stop, they’d send pitches to local reporters and ask for in-person meetings. “We went out there with a plan,” Cridland says.

By booking cheap Airbnbs and motels along the way, they spent less than $6,000 on the whole trip. And thanks to all the press—both local and national—online sales from the U.S. surged tenfold and now make up more than half of Cridland’s business. The road-trip stunt also drummed up new business for his PR operation. “It’s a profit-making business,” says Cridland. “And we use that profit to invest in our fashion brand, which is why it’s 100 percent privately owned.””

50 Most Daring Entrepreneurs

8. Russ D’Souza & Jack Groetzinger

SeatGeek

Writing their own ticket to the ticket wars

This spring, when SeatGeek spent $56 million to acquire Israel-based TopTix, the ticketing industry suddenly got a lot more interesting. Until then, SeatGeek was just another place to buy and sell secondary tickets. But more than 500 clients, from sports venues to music festivals, use TopTix’s software to sell tickets directly to fans. That means SeatGeek just armed itself to go up against the behemoth Ticketmaster. And with its new software platform SeatGeek Open, it’s enabling clients to sell tickets directly on their own apps, sites, and even social media. “Venues realized they can’t just expect someone to go to their website or Ticketmaster,” says SeatGeek cofounder Russ D’Souza. “They need to take advantage of the fact that fans are in all these mobile experiences.”

50 Most Daring Entrepreneurs

9. Amanda de Cadenet

Cedric Buchet

#girlgaze

Creating her own opportunity by creating opportunity for others

“I didn’t set out to start a business,” says Amanda de Cadenet. Instead, she was just a photographer and TV personality trying to make a point. “You look at magazine covers, editorials, ads—they’re all photographed by men, but they depict women,” she says. She wanted to encourage female photographers to share their work online and increase visibility. Her call to action came in 2016 through the Instagram hashtag #girlgaze, and to date, 2.8 million images have been shared. Teen Vogue even handed an entire issue over to the cause. “We curated the September issue and provided more than eight paid photography jobs to girls around America,” she says. “That’s when I knew this could be a self-sustaining business.” This year, #girlgaze evolved into a one-stop creative agency. “We conceptualize the content and use our network of talent to execute it,” she says. Projects with Warby Parker, Gap, and Shinola have created numerous campaigns and jobs for female photographers, and #girlgaze is now building a portfolio-hosting and job-listing site. “People say, ‘Oh, we don’t know where to find girl photographers.’ We’ll tell you where to find them.””

50 Most Daring Entrepreneurs

10. Ellie Dinh & Quang Dinh

Girlfriend Collective

Pricing product at $0

When activewear brand Girlfriend Collective launched in 2016, it wanted to amass loyal customers. “But we didn’t know how to get people to trust us,” says Ellie Dinh, who founded the company with her husband, Quang Dinh. Advertising seemed a gamble…so what if they just gave away product instead? On Facebook, they announced they’d sell pairs of $68 eco-friendly leggings for just the cost of shipping—and received 10,000 orders in hours. The promotion ran for months. “We’re still climbing out of a hole,” Quang says. But now they’re selling at full price, and those first freebie recipients are back (and paying) for more.

50 Most Daring Entrepreneurs

11. Wade Foster

Zapier

Paying new hires to leave

“Many tech companies pay to move new hires to the Bay Area. But this spring the Silicon Valley–based workflow automation software company Zapier offered the opposite deal: $10,000 to help any Valley resident move somewhere else. (Zapier’s workforce is remote.) The offer got so much press that it attracted excellent applicants—from all around the country. Zapier has since hired or made offers to 41 new people, including only one from San Francisco. “We’re ready and willing to make it happen [for more people],” says CEO Wade Foster. But compared to hiring pricey recruiters, Zapier has gotten the deal of the century.”

50 Most Daring Entrepreneurs

12. Piera Gelardi

Refinery29

Proving that a lifestyle brand can be a heavy hitter

When Refinery29 launched in 2005, it was just one in a sea of fashion blogs. But the startup had larger ambitions, and over 12 years it has evolved into a holistic news and lifestyle site, one that’s eager to wade into thorny issues its competitors tend to run from. Refinery29’s unmistakable voice (think an ultra-supportive, ultra-­informed big sister) has attracted a global audience of more than 20 million. Executive creative director Piera Gelardi—who cofounded the site with Christene Barberich, Justin Stefano, and her now-husband, Philippe Von Borries—is the embodiment of that voice, constantly pushing her own limits as much as the brand’s.

In September, you may have followed Gelardi on Instagram as she toured through 29Rooms, Refinery’s Brooklyn art-show-meets-funhouse that promotes up-and-coming artists and causes, including Planned Parenthood and Women’s March. (This December, 29Rooms will set up shop in Los Angeles for the first time.)

Or maybe you’ve seen her speak about the 67% Project, an initiative launched last fall to increase the representation of plus-size women in media and retail—including curating a new stock-photo library—inspired by the fact that while 67 percent of American women are “plus size,” they’re seen in just 2 percent of media.

Or perhaps, in July, you came across Gelardi’s deeply personal story about her own miscarriage, which she suffered this June. On Refinery29 and on social media, she chronicled the trauma and the struggle to move forward, and expressed gratitude for her friends, family, and her company’s health insurance—especially when her hospital bill arrived.

Gelardi shared her story on the same day the U.S. Senate was preparing to vote on the Health Care Freedom Act, otherwise known as the “skinny” repeal of Obamacare. Why? The 20 hours she spent in the ER cost her $150 out-of-pocket, but the grand total without insurance would have been a staggering $40,374.06—more than enough to bankrupt the average American family.

“It’s always important for us to challenge different taboos that create shame in women’s lives and keep them from having the important conversations that move them forward,” Gelardi says. “I want to help dismantle that shame. After my miscarriage piece posted, we had so many submissions from women sharing their own stories and hospital bills, and it really started a conversation about healthcare. So many things in our culture are kept in the dark, but it just perpetuates suffering and keeps people from the connection they deserve in those tough moments.”

Keeping in line with Refinery’s mission, Gelardi’s story came with a call to action. Not only were readers encouraged to share their own #CostOfCare stories, many of which were posted on the website, but they were also given info on access to healthcare, how to contact government representatives, and support groups for traumatic experiences. “We try to strike a balance by providing tools, not rules,” Gelardi says. “We really think about what the resource is.”

Just weeks later, they were guiding their readers through another difficult topic and news event: the deadly white nationalist rally in Charlottesville, Va. Gelardi and her team shared a series of tools to help the Refinery community be an ally to those affected, and provided tips on how to effectively talk about race.

“You have to go into these uncomfortable territories,” Gelardi says, speaking about both life and business. “Sometimes we try and sometimes we mess up. But it’s always going to be important for us to take a stand.” — Stephanie Schomer

50 Most Daring Entrepreneurs

13. Tali Gumbinger & Lizzie Wilson

McCann New York

Challenging the bull, and the ad industry

Tali Gumbiner and Lizzie Wilson had a doozy on their hands: How could their advertising firm help promote State Street Global Advisors’ index fund of gender-diverse companies? Their answer was Fearless Girl, a bronze figure in a power pose that they installed in March in the face of Wall Street’s famous Charging Bull. “It was a delicate moment, a high-profile location,” says Gumbiner. “Either we’d capture lightning in a bottle, or it’d just flop.” The award-winning project delivered—not only did it help its client reach a nearly 400 percent increase in trading volume, but the statue itself became an icon for social movements, and New York City renewed its lease into next February. “Our favorite thing is what it means for the industry,” says Wilson. “The idea that the work can be about doing good in the world.”

50 Most Daring Entrepreneurs

14. Clay Hebert

Crowdfunding Hacks

Giving up the home base

At the end of 2016, Clay Hebert needed a change. So he ditched his apartment in San Diego and hit the road. “I had two months of speaking gigs lined up, and I figured I would clear my head and get a place after,” says the marketing strategist. Nine months later, he’s still at it. “Working on the road has forced function in my business,” he says. Because he isn’t tethered to an office, he’s more proactive about finding opportunities in new cities and spends more time meeting new people—anywhere. “I sat next to a woman on a plane who’s head of innovation at a major consumer goods company. We may work on something,” he says. “I call it business development via plane networking.”

50 Most Daring Entrepreneurs

15. Randy Hetrick

TRX

Taking copycats to court, for the benefit of everyone

Randy Hetrick became famous for TRX, his suspension training equipment, which was originally sold to gyms and trainers. He started selling it on Amazon in 2008, and by 2011 knockoff listings started to appear. Fighting those phonies was a slow process. “Amazon would make you do a test buy, so we’d have to order one of the knockoffs, wait for it to ship, affirm that it was a fake, then spend weeks on bureaucracy to get the listing removed,” he says. It wasn’t just the millions in lost revenue that stung but the brand equity that took a bruising. “Customers would call us for a refund after the equipment failed and find out they bought a counterfeit.” Despite no wrongdoing, “they were furious with us,” he says.

Over the past decade, Amazon’s reporting process has gotten quicker, but fraudsters have grown more sophisticated. Instead of selling product with a fake TRX logo, they manufacture a look-alike product under a different name. “When a fake listing is taken down, within a matter of minutes or hours, these e-commerce parasites put up new ones,” he says. “It’s whack-a-mole in the worst way.” That’s why many sellers on Amazon just take the hit.

But not Hetrick. In 2014, he turned to the federal courts and sued Antioch, Calif.–based Woss Enterprises for patent and trademark infringement, alleging that the manufacturer—the most egregious TRX-knockoff purveyor—manipulated e-commerce platforms to siphon off legit customers, costing Hetrick nearly $6 million in lost profits. This February, a federal jury sided with Hetrick and awarded TRX $6.8 million in damages, setting a valuable legal precedent for intellectual property moving forward.

Woss filed for bankruptcy, but Hetrick says the real victory will come from stronger sales and fewer parasites. “Before, we’d send a cease-and-desist letter, and fraudsters wouldn’t care,” he says. “Now we send one with news of the damages awarded, and they decide to focus somewhere else.” Since the verdict, TRX sales are up 100 percent year over year. “It makes you realize how much has been stolen,” he says.

50 Most Daring Entrepreneurs

16. Nicholas Horbaczewski

Drone Racing League

Creating a 21st-century sport

Two years ago, not many people had heard of drone racing. (You may still have never heard of it.) It’s a sport that drone owners dreamed up and play as a hobby. But self-proclaimed adrenaline junkie Nicholas Horbaczewski saw greater potential. In 2015 he created the Drone Racing League, a tech, sports, and media startup with $32 million in funding whose eclectic investors include Miami Dolphins owner Stephen Ross. “Creating a sport from scratch involved pilots, spectators, broadcasters, sponsors, and venues,” says Horbaczewski. “But first we had to build the actual drones.” For fans, the races look like computer games, with drones flying more than 90 mph, viewable via a live feed from pilots’ headsets. Last year’s inaugural tournament aired on ESPN, and business has soared since then. The 2017 races led to deals with broadcasters in 87 countries and sponsorship deals with Allianz, Amazon, and the U.S. Air Force. The league is investing in tech to deliver a more immersive experience and tying up a gambling partnership with Betfair—for those who find the races aren’t sufficiently nerve-jangling.

50 Most Daring Entrepreneurs

17. Chieh Huang

BOXED

Boxed

Barreling into the future, and bringing his entire team with him

Boxed sells bulk products online at wholesale—like Costco, but digital—and until recently, orders were packed by hand. Sometimes, when it got busy, everyone on staff (execs included!) had to hit the fulfillment floor. But after raising $165 million in funding, founder Chieh Huang built a solution: a 150,000-square-foot automated facility designed for big orders. Despite staff fears, he promised no one would be replaced by robots. “Guess who’s going to operate and troubleshoot these structures?” he’d say. And troubleshoot they did. Huang insisted that the system operate at full speed right away so bugs could be worked out quickly. “The whole thing almost melted down,” he says. Employees slept on the floor for weeks. In time, they fixed the bugs, and Boxed strode into the future. Best of all: No one’s been laid off.

50 Most Daring Entrepreneurs

18. Jackie Hunter

BenevolentBio, a subsidiary of BenevolentAI

Making life-or-death decisions with AI

Discovering a new drug requires combing through reams of data in what can be a 12-year, $1 billion process. And still, things get missed. “Big Pharma’s business model is not sustainable,” says industry veteran Jackie Hunter. “It doesn’t use a fraction of available evidence.” So she’s building a way to use artificial intelligence to process scientific results exponentially faster, enabling researchers to work on many drug programs at once for diseases from ALS to Parkinson’s. It may sound scary, handing such a task to robots. But, she says, “AI can be used as a force for good.”

50 Most Daring Entrepreneurs

19. John Idol

Michael Kors

Walking away from the masses he once courted

John Idol took over as CEO in 2003 and famously embraced a strategy of accessible luxury (selling Michael Kors as a nice brand most people can afford). That led to big sales and hundreds of stores worldwide, but in recent years, sales have plummeted—largely because the brand became too ubiquitous, almost too accessible. So now Idol is steering Kors into a bold new direction—not just by making his brand more exclusive but by laying the foundation for a new luxury conglomerate. Idol is nixing discounts on his products, closing 100 or so outlets to concentrate on the glitzier ones, and, in July, agreed to pay $1.2 billion for British shoe brand Jimmy Choo. Key to this plan is reaching millennials in Asia. According to Accenture, 60 percent of the world’s millennials will live in Asia by 2020 and their disposable income will nudge $6 trillion. Idol wants to be top of their mind. Jimmy Choo’s sales in the region rose 19.2 percent last year, and in August, Michael Kors became the first upmarket brand to accept the Chinese online credit card Huabei on its Asian website.

50 Most Daring Entrepreneurs

20. Ebele Ifedigbo

Mark Coffin

The Hood Incubator

Making pot dealers legit

Legal pot has been a boon to many entrepreneurs—but people who were “underground cannabis entrepreneurs” (a.k.a. pot dealers) have often been left out, lacking the capital, the networks, and, sometimes, the clean records it takes to go legit. Ebele Ifedigbo, along with cofounder Lanese Martin, wants to change that. Their Oakland incubator connects budding entrepreneurs with jobs and apprenticeships, and hosts legal clinics on red tape and cleaning up records. “This is an economic opportunity unlike any that we’ve seen for our community,” Ifedigbo says. “We want to make sure we’re really taking advantage of it.”

50 Most Daring Entrepreneurs

21. Sami Ismail

Sami Ismail

Intellect Events

Staying to support his fellow Syrian entrepreneurs

Entrepreneurship is challenging in any context. But for Sami Ismail, it’s challenging in a way few others can understand: His company, Intellect Events, which puts on cultural, business, and networking events for entrepreneurs, is based in Damascus, Syria. “We’re living in a war zone,” Ismail says.

Ismail, 27, is a veteran of the region’s startup scene, having launched his first company, Findbook, in 2010. He conceived of it as a sort of Amazon for Syria, but when a promotional book fair for the brand brought in more money and buzz than the actual brand did, Ismail realized the entrepreneur community was hungrier for intellectual events and safe spaces to gather and network. So he closed Findbook and launched Intellect Events with a partner in 2011.

“The fabric of our society has been hit hard by the war,” he says. “It has enlarged cultural and social gaps that already existed. People are eager for anything that gives them a chance to engage in conversation and mutual understanding.” He continues to provide this even as civil war ravages his country—because, yes, Syria is a state in crisis, but it is also home to entrepreneurs who are trying to succeed despite extreme challenges, including a lack of financing or global mentorship. Ismail hosts quarterly conferences for entrepreneurs in tech, social media, and public relations, which go on for two to five days and attract hundreds of attendees. He offers a mix of networking and programming, focusing on topics including global entrepreneurship, useful PR tactics, and the challenges that come with growth and scale.

Ismail has attracted speakers from Microsoft and other major companies, as well as researchers and professors from academia, although booking foreign guests isn’t easy, especially American ones. It’s against the law for an American company to attend anything sponsored by the Syrian state, so Ismail has to be explicit that neither he nor his events have anything to do with the government. And even then, people get squeamish about the optics. Once, an investment firm sent a speaker to Ismail’s event, but when the connection received public scrutiny, the investment firm publicly denied any involvement. (Microsoft, on the other hand, has publicly supported Ismail.)

Of course, although Syrian entrepreneurs have much in common with global entrepreneurs, they also face unique problems. A range of hurdles—simply attracting clients, having e-commerce reach outside the country, dealing with painfully slow internet connectivity and regular power outages—means day-to-day operations can feel impossible. “Bandwidth is so bad,” Ismail says. “I’ll attend conferences in Lebanon and hear them talking about their bad internet, and I think, You haven’t seen Syrian internet!” Not to mention, he estimates that more than half the country’s skilled workforce has fled in just two years, leaving huge gaps in the economy and making hiring difficult.

Ismail insists that there are benefits to operating in Syria, however. Those gaps in the economy? He sees them as opportunities—because although there’s no official tally of how many people are now living in Syria, it’s still a country with millions of residents and a lot must be done. “Entrepreneurs who have the ability to adapt and cope with change see the glass half full and make good out of bad,” he says. “Entrepreneurs in any country with internal conflicts can produce results with the right mindset.”

Still, it’s easy to wonder why Ismail hasn’t fled, both for safety and better business opportunities. “It’s the million-dollar question,” he admits. “Ninety percent of my college friends have relocated. If you’re one of the 10 percent left, you need to really know why you’re staying and what you’re going to do with your time.” His answer: He’s loyal to the local entrepreneurs who have come to rely on him, and he wants to find new ways to innovate under unimaginable circumstances. And leaving comes with no guarantees, either; he’s watched countless friends go to Europe, Asia, and Silicon Valley, only to encounter new challenges and prejudices that make it difficult for them to raise money or attract clients. “We’re really afraid of the future,” he says. “We don’t know what’s going to happen. But that doesn’t stop us.” — Adam Elder

50 Most Daring Entrepreneurs

22. Patty Jenkins

Jason Laveris/Getty Images

Wonder Woman

Making the impossible profitable

Patty Jenkins took a film repeatedly deemed impossible to make by Hollywood and turned it into a $400 million box-office hit. But it wasn’t easy. For instance, production execs wanted to cut a pivotal scene in which Gal Gadot’s Diana Prince realizes her own power and becomes Wonder Woman. Dubbed No Man’s Land, the scene shows Gadot marching forward through a battle scene, bravely facing the danger that awaits at the other end – and fighting off countless bullets in the meantime. (The execs thought it would fall flat with audiences because she wasn’t physically battling an actual adversary.) Jenkins fought for her vision and saved what became the film’s most powerful, buzzed-about moment.

50 Most Daring Entrepreneurs

23. Micha Kaufman

Fiverr

Going after an audience he used to dismiss

Fiverr began as a marketplace for $5 services, which often meant cheap offers that undercut professionals. (A much-criticized Fiverr 2014 Facebook ad: “You’re paying too much for design.”) But this June, it launched Fiverr Pro, a platform for the high-skill talent it once pissed off. Now, buyers can more quickly reach and connect with qualified talent, and freelance workers can obtain more regular work and projects – complete with round-the-clock support from Fiverr’s team. It looks like the community is more than willing to forgive and forget Fiverr’s past transgressions: Already, more than 10,000 professionals have joined, charging fees of up to $9,000.

50 Most Daring Entrepreneurs

24. Scott Keyes

Scott’s Cheap Flights

Being faster (and bolder) than the airlines

In September, Air Transat accidentally priced a roundtrip flight from Toronto to Dublin at $98 Canadian. The airline fixed the price almost immediately (up to $600), but not before Scott Keyes blasted it out to his readers. Since 2013, Keyes’ emails have been notifying readers about deals and fare mistakes—a project that exploded this year, as his email list reached one million subscribers and evoked a love/hate view from airlines. “They love us when we help sell unsold inventory but hate us when we get those mistakes out to people,” he says. Could they come after him? Maybe, but he’s undaunted: He’s now launching a mobile app with faster alerts and better customization.

50 Most Daring Entrepreneurs

25. Stephanie Lampkin

Blendoor

Blendoor

Holding Silicon Valley accountable

Stephanie Lampkin is tired of what she calls diversity theater, which she defines like this: “Companies hire someone as a diversity officer, with no budget or team, just to act as a spokesperson for the company.” The rank and file might get padded out with more women and people of color, but those demographics rarely make it to the C-suite.

Lampkin is the CEO of Blendoor, an app that helps companies take bias out of hiring by presenting only candidates’ merits, rather than their names and photos. In recent years, as more tech companies have gone public with hiring data, she’s grown frustrated with Silicon Valley’s tendency to measure diversity by simple headcount, instead of more meaningful metrics like engagement and retention. “So we decided to showcase the stories behind the numbers,” she says.

The inaugural BlendScore was released in May, a ranking of 161 tech companies based on everything from the demographics of the leadership team to retention statistics and recruiting practices. Lampkin’s team built an algorithm based on publicly available information and scoured company websites, LinkedIn, and Glassdoor to learn parental leave policies and the like. They contacted each company to verify their findings and scored them on a scale of 1 to 100.

Intuit topped the list with a score of 82, while Slack (47), Etsy (37), and Netflix (27) hovered near the bottom. “When the list first came out, we got a lot of calls from people concerned about branding,” she says. “That’s a good thing, because now we’re connected to people driving decisions.” But the goal isn’t to shame; it’s to share best practices. These are, after all, the kinds of companies she’d like to be using her service.

The lists will continue. Blendoor’s team is already at work on an updated list and a separate ranking of VC firms. “There really is no silver-bullet solution,” she says. But attention, she reasons, is a good first step.

50 Most Daring Entrepreneurs

26. Kristin Lemkau

JPMorgan Chase

Dropping advertising by 98.75 percent

Chase once advertised on 400,000 websites. In March, Kristin Lemkau made what seemed like a radical decision: She cut that to 5,000. She did so because Chase ads—like many companies’ ads—were appearing on hate sites, the result of how online ads are automatically distributed. Lemkau reasoned that she’d rather have less visibility than the wrong visibility. But as it turns out, she got the best of it all. Those 5,000 ads (on handpicked sites) were seen by almost as many people as the 400,000 ads—an insight perhaps into how poorly trafficked the internet’s seedier corners really are. Eight months later, Chase says its footprint has expanded to 10,000 sites, still a tiny fraction of its past.

50 Most Daring Entrepreneurs

27. Mitch Lowe

MoviePass

Slashing prices harder than Freddy Krueger

MoviePass is a dream product for movie buffs, but it’s been a nightmare for stakeholders. The company, which enables subscribers to see a free movie every day at 91 percent of U.S. theaters, has never been profitable. In 2016, it brought in former Netflix and Redbox executive Mitch Lowe as CEO, and this August he made a bold change: He dropped MoviePass’s monthly plan from between $30 and $50 to just $9.95. In response, its subscriber base reportedly soared from 20,000 to 150,000 in a week. MoviePass hopes to break even on the subscriptions, but Lowe believes the increased attendance will open up new revenue streams from studios and theaters. “It may sound crazy,” Lowe says, but at Redbox he offered $1 rentals while Blockbuster was charging $5. “And we all know what happened to Blockbuster,” he says. Plus, the more people use MoviePass, the more data it can gather—like how many trailer views it takes before someone buys a ticket—which it can then sell to studios and theaters.

50 Most Daring Entrepreneurs

28. Daniel Miller

Duncan Miller Gallery

Saving a country’s cultural history, at a cost

It was supposed to be a simple transaction. Fairfax Media, one of Australia’s largest media companies, wanted to digitize two million photos in its newspaper archives. So it struck a deal with an Arkansas company that would scan the images and could then sell off the originals. In 2013, Fairfax shipped over the photos. A few months later, the FBI raided the Arkansas company and charged it with an unrelated fraud. (Its owner pleaded guilty this March.) Years passed. A bank took control of the photos and would likely sell them off indiscriminately.

When Los Angeles–based photo dealer Daniel Miller heard about the situation this year, he asked to take a look. “To see a collection that was a pictorial survey of the history of a country was amazing,” he says. “My idea was that these should be sent back, but I couldn’t find any entity that could deal with something this big.”

Miller had no connection to Oz but felt suddenly responsible, the last man standing between a country’s cultural history and potential oblivion. He also saw a business opportunity. So in August, he bought the collection (the price was undisclosed but in the millions) and began plotting how to get most of it back to Australia—selling to cultural organizations, nonprofits, museums, and libraries at a subsidized rate, and to collectors at full price, so he could fund the subsidies. So far, 50,000 photos have made it back home, and in September, he launched an exhibition called “The Australians” at his Santa Monica gallery, which he plans to tour around the U.S. Will he make a profit on this? He hopes so, but he knows only one thing for sure: “It was the right thing to do,” he says.

50 Most Daring Entrepreneurs

29. Maria Molland Selby

Thinx

Taking over after the year’s strangest PR crisis

Stepping into a CEO vacancy is never easy—especially when that position is open due to one of the worst PR scandals of 2017. Yet Maria Molland Selby jumped eagerly into Thinx this summer, with big plans to scale its team and expand its product line of leakproof period underwear—all while fixing the toxic culture that made national headlines and imperiled the company’s future.

Thinx’s eccentric founder, Miki Agrawal, left the company in March following employee complaints of below-standard wages, fuzzy leave policies, and inappropriate behavior (including attending meetings via video chat from the toilet). One former employee filed a complaint against the founder for sexual harassment.

“I started talking to the board a few days before the [scandal] broke,” Selby says. “And when it finally did, I thought, Wow, this is certainly an HR challenge.”

Beneath the mayhem, Selby saw something worth fighting for. “I was struck by the strength and passion of the team,” she says. “They really believe in the mission.” It helped that Selby herself was already a believer. Years earlier, a friend had shared that Thinx made her period seem like a nonissue and gifted a bunch to her circle of friends. “Everyone immediately started raving about them,” Selby says.

Now she wants to scale that passion—fast. She has plans to double the team’s 35 members by the end of 2018, has launched a new line of cotton underwear, and is pushing harder into international markets. She is also hiring a head of HR, has published an employee handbook, and has created a workflow for concerns and complaints. “It was a big event,” she says of the scandal, “but the team has moved on. Last May, we had our highest-revenue month ever. That says a lot about the team.”

50 Most Daring Entrepreneurs

30. Rev. Georgiette Morgan-Thomas

American Hats

Saving a dying business

Rev. Georgiette Morgan-Thomas, a 68-year-old retired social worker and hat lover, had never worked in manufacturing before, but when she learned that a Pennsylvania hat factory was at risk of closing down, she felt compelled to do something. So she bought it, figuring she’d let the existing production manager run operations while she took care of the business side. Then the manager quit, a giant wholesale customer left, and she was forced to do everything. So she fell back on her people skills: She showed off hats in coffee shops, befriended boutique owners and designers, and opened a Harlem showroom. Today the once debt-ridden factory makes a profit. “As I write in my journal each day,” she says, “it’s the joy of the struggle.”

50 Most Daring Entrepreneurs

31. Elon Musk

Michael Kovac

SpaceX

Out-of-this-world thinking

Every day seems to bring a new fantastical endeavor from Elon Musk, who has become Silicon Valley’s Willy Wonka. This winter, SpaceX plans to launch Falcon Heavy, a commercial rocket capable of taking crewed missions farther than they’ve ever gone. (Mars, anyone?) The Boring Company, an infrastructure and tunneling company that debuted in January, recently won approval to drill a two-mile test tunnel near SpaceX in Hawthorne, Calif. Over the summer, that town also hosted a competition to build pods for Musk’s proposed Hyperloop. (The vision: People-filled pods would be propelled by magnetic accelerators through tubes at speeds of 700 mph; a trip from New York to Washington would take 29 minutes.) More immediately, Musk’s electric-vehicle and energy-storage startup, Tesla, is gearing up for production of its mass-market Model 3 car, for which there’s already a waitlist 455,000-people strong. And by this past August, he had raised $27 million for his next startup, Neuralink, which could someday help repair neurological damage by linking human brains with computers. What of all this will truly work? The world can’t wait to find out.

50 Most Daring Entrepreneurs

32. Jason Njoku

IROKOtv

Changing everything to chase the right customer

IROKOtv launched as a subscription service streaming Nollywood films—essentially a Netflix for Nigeria. One problem: Few Nigerians have wi-fi strong enough for streaming, so most subscribers were from the far smaller pool of Nigerian emigrants living in the West. To change that, starting in 2015, Jason Njoku built a new product that enables downloads (no more buffering!), created original content (to drive subscriptions), and built wi-fi kiosks across Lagos where subscribers could download content. The investment paid off: This June, Nigeria surpassed the U.S. and Europe as his largest subscriber market. “The disruptive and often painful journey I’d taken the entire organization through was worth it,” Njoku says. He’s now angling to expand across Africa.

50 Most Daring Entrepreneurs

33. Issa Rae

Michael Rowe/Getty Images

Issa Rae Productions

Telling real stories

Issa Rae may be best known for her hit HBO comedy Insecure, which had a season two debut this year that doubled last year’s ratings. But as the first black woman to create and star in a premium-cable series, she’s using her success to push industry-wide change—and stories that look and feel authentic to their creators and target audience, despite Tinseltown pushback. “She’s [always] saying, ‘I only want this shot in Inglewood, and I only want this cast—I don’t care that you’ve never heard of them before,’” says Deniese Davis, head of production at Issa Rae Productions, which also creates many YouTube series. Rae and Davis are also cofounders of Color Creative, which produces TV pilots by people of color.

50 Most Daring Entrepreneurs

34. Bozoma Saint John

Maya Darasaw, MAD Works Photography

Uber

Offering love to a very tarnished brand

Everything Bozoma Saint John touches turns to pop culture gold. Last year, as the head of global consumer marketing for Apple Music, she brought the funk to the Worldwide Developers Conference, leading a sing-along of “Rapper’s Delight” onstage to showcase the service’s new features. In 2012, as head of music and entertainment marketing for Pepsi, she wrangled celeb endorsements with the likes of Nicki Minaj, Eminem, and Kanye West. And in an act of amazing foresight—back in 2002 while working for Spike Lee—she championed a newly solo Beyoncé to star in a Pepsi commercial.

So tongues wagged in Silicon Valley this June when Saint John (or Boz, as she calls herself) took on a newly created role as chief brand officer at Uber, a company whose reputation may charitably be called beleaguered. Mired in accusations of sexual harassment, a toxic internal culture, and cutthroat competitive tactics, the founder and former CEO, Travis Kalanick, resigned around the same time Saint John joined. A new CEO, Dara Khosrowshahi, formerly of Expedia, was brought on in August.

For Saint John, joining Uber was about knowing in her gut that she was ready to take on a full-scale brand turnaround—and genuinely believing that Uber was worthy of one. “I expected to come in to doom and gloom and people walking around with their heads down,” she says. “But overwhelmingly, people are inspiring and want to do great things for the future. It’s a reinvigorated group of people who want to do the right thing.”

Saint John knows authentic reinvention will hinge on internal transformation—no campaign in the world could (or should) paper over the troubles Uber created for itself. “The things that have happened that make people feel like they can’t support the brand need to stop,” says Saint John. “It’s not the job of one; it’s the job of many to change the brand of Uber.” That means working with HR and the company’s leadership team to create a more diverse and inclusive environment. To that end, in August Uber announced a three-year partnership and $1.2 million commitment to Girls Who Code; Saint John will also join its board. It’s a first step, she says, in creating a more robust pipeline of women engineers.

Despite the heavy lifting and time required to revamp Uber’s culture, Saint John thinks there is immediate work to be done closing the gap between how people think about Uber the service and Uber the company. Lots of people love the former; the latter, not so much. Saint John sees it as part of her role to refocus the storytelling.

“I do believe in complicated brands and complicated stories,” says Saint John. “I want to show more than one side of this thing. There are things happening with product, things happening with drivers, things happening with riders, things happening with new partnerships. I want to be able to tell a layered story.”

The first campaign released during Saint John’s tenure features 17 TV spots, one for each of Uber’s official NFL ride-sharing partners. The ads feature real-life Uber drivers in their favorite team’s gear, getting psyched for game day before driving to the stadium. The ads are a love letter to drivers, who have at times had strained relations with their employer. “The drivers are talking to people every single day while they take them from here to there,” she says, “and I want to make sure their humanity is also seen.”

As for the competition, which saw Uber’s bad press as a business opportunity, Saint John says bring it on. “I’ve always been in business with strong competitors, whether it was the cola wars, or Apple versus Android, or Apple Music versus Spotify,” she says. “I almost feel like I can’t do my work unless there is competition. I was a track athlete in high school, and there’s nothing better than having someone three lanes over breathing down your neck to help you run faster.” — Erin Schulte

50 Most Daring Entrepreneurs

35. Oliver Sanchez

Plug

Helping immigrant entrepreneurs flourish in the U.S.

When Mexican entrepreneur Oliver Sanchez ran Plug coworking spaces in Brazil, he realized some startups need more than just a desk and wi-fi—especially when they’re run by immigrants. “Many entrepreneurs from abroad face the same challenges: lack of a network, cultural adaptation, and a different confidence level,” he says. So last year, he opened Plug Cambridge, an incubator that provides space, mentoring, and visa assistance to foreign-born entrepreneurs in Massachusetts. “I want to prove that non–U.S. entrepreneurs are an asset to the economy, that they’re as good as someone from here,” he says.

50 Most Daring Entrepreneurs

36. Ted Sarandos

Netflix

Betting it all on a big vision

If you anticipate a negative cash flow of up to $2.5 billion this year and have long-term debts of $4.8 billion on the books, some advisers might suggest you pull back on spending. Netflix takes a different approach. Chief content officer Ted Sarandos insists that prestige fare brings in more viewers, whom it can then monetize with higher subscription prices. That’s why the company will increase spending on original programming from $6 to $7 billion next year. In August, the network also poached Shonda Rhimes from ABC, cajoled the Coen brothers into TV production, and lured David Letterman out of retirement. Despite the sticker shock, Netflix insists it’s being cost-savvy. By owning content, it can renew hits, ditch flops, and retain rights. It also recognizes that the future of content development is global. Netflix currently has 104 million members in more than 190 countries and produces shows in 19 countries. “Some of them work out great, some of them work out not so great,” said Sarandos in an investor call in July. “We can learn from every single one of them.”

50 Most Daring Entrepreneurs

37. Howard Schultz

Starbucks

Leaving a thing that’s really, really working

Breaking

Howard Schultz saved Starbucks from a downward spiral and could have kept running a caffeinated victory lap. Instead, less than a year ago, he stepped down from CEO (to executive chairman) and is now helping the brand launch upscale coffee bars called Reserve, as well as a new brand of single-origin coffee beans to go with it. (It comes at a price; in stores, a cup can cost up to $10.) Additionally, Schultz will create a handful of ultra-luxe standalone coffee “destinations” called Reserve Roastery – all in an effort to win over the big-spending coffee snobs that may deem Starbucks too mass-market for their morning routine.

50 Most Daring Entrepreneurs

38. Daniel Schwartz

Earl Wilson/The New York Times/Redux

Restaurant Brands International

Taking big bites of a global restaurant market

Daniel Schwartz was 30 and had no restaurant experience when he became Burger King’s CEO in 2010, after his investment firm gained majority ownership. Following months working the grills, swirling soft-serve, and even scrubbing toilets, he instituted changes that led to a tripling of BK’s valuation. In 2014, he merged BK with Tim Hortons and promised big international expansion for that brand—which hasn’t happened as fast as it should have, some analysts grumble. That didn’t stop him from buying Popeyes for $1.8 billion this year, making a big bet on a global demand for Louisiana-style fried chicken.

50 Most Daring Entrepreneurs

39. Tina Sharkey & Ido Leffler

Brandless

Brandless

Taking “stealth mode” to the next level

Tina Sharkey and Ido Leffler had a bold idea: an online store that sells only generic versions of daily essentials for $3 each. The dish soap, say, would just be labeled dish soap. But they shared this with almost nobody. “When you’re taking on the reimagination of modern consumption like we are, it’s better to do it in stealth,” says Sharkey, a serial entrepreneur and venture capitalist. “It’s better to disrupt than announce your disruption and then try to disrupt.” So as they raised money and built their company, Sharkey and Leffler claimed they were building something called Dhosi—and included it on business cards and in LinkedIn profiles, employee recruitment outreach, and investor decks. They even built a Dhosi website. “Dhosi is the name of a historical hill in India where, legend has it, dirt was said to have healing properties. We joked that it was the first known brand,” Sharkey says. “And, you know, the URL was available.” The deception paid off: When they launched their real brand (called Brandless) in July, the press pounced and orders came in from 48 states. By week six, a double-digit percentage of customers were already reordering products.

50 Most Daring Entrepreneurs

40. Stephen Shearin

American Green

American Green

Transforming a desert depot into a marijuana mecca

What if a pot company bought an entire town?

The idea started as a flippant comment during a brainstorming session at American Green, a marijuana-focused technology company. “As we went through the possibilities—to be able to dictate our own future in a town and produce a blueprint for others to replicate in other towns—we fed off our own excitement,” says Stephen Shearin. What if the town could become a manufacturing hub, pumping out cannabis-infused drinking water for nearby distribution? What if it could be reimagined as a tourist destination, with visitors attending ganja workshops, shopping at dispensaries, and staying at pot-friendly rentals?

After months of researching locations, the company settled on the unincorporated Nipton, Calif. It’s home to one general store, a 100-year-old five-room hotel and café, and a handful of houses scattered across 120 acres in San Bernardino County, and it already had an owner that was putting it up for sale. (How does one entity own a town? Answer: Own all of its land.) In August, after four months of negotiations, American Green closed on the purchase for a reported $5 million. But serious challenges are ahead: logistics, regulations, marketing, funding. Nipton has already had more than half a dozen private owners over the years, and efforts to rebrand have so far been elusive.

Adding marijuana to the mix only makes it harder. Even the process to incorporate the town so the company can apply for a grower’s license may be years in the making. And, until now, American Green has had a low profile and relatively discreet products: marijuana-dispensing vending machines, seed-to-sale tracking software, marijuana-infused balms and oils. “What we’re discovering is that the most exciting parts of this project—and the most difficult—are the things we couldn’t really consider until we were in the town,” Shearin says. But he believes that if he builds it, they will come.

50 Most Daring Entrepreneurs

41. Jon Steinberg

Cheddar

Producing TV for an audience that’s everywhere

When Jon Steinberg launched his “post-cable” millennial business channel on Facebook Live in early 2016, no one believed millennials would watch serious news. But Steinberg realized platform, not audience, was the problem. “Facebook is not willing to separate substantive content from viral stunts,” he says. So this year, he forged deals across media—producing “flash videos” for Amazon’s Alexa, segments for local TV networks nationwide, distribution on AirAsia and JetBlue, new live feeds on Twitter, and more. Total viewership has jumped to 148 million. “Facebook may be the 800-pound gorilla,” he says, “but there are tons of 200- and 300- and 500-pound gorillas.”

50 Most Daring Entrepreneurs

42. Rachel Tipograph

Christelle De Castro

MikMak

Changing her business model…right after she got funded

Rachel Tipograph thought she had a digital retail winner. Her app, MikMak, launched in 2015 and created short, funny infomercials to get consumers to laugh all the way to checkout. Brands like GE and L’Oréal signed up to sell products through it. But in 2016, Tipograph realized that dedicated shopping apps weren’t the future. Instead shoppers relied more and more on Google, Amazon, and Facebook to find and buy. So months after closing a 2016 fund-raise, she told investors to forget the app—she was going to license MikMak’s platform to retailers to use on their own. “It’s not an ideal time to change your model,” she admits. “You go out to the venture market with a narrative, and if you change it, that spooks people.” Only one investor ran; the rest cheered. To date Tipograph has raised $4 million.

50 Most Daring Entrepreneurs

43. Alex Tomlin

Diageo

Hablar en otro idioma

Days before the 2016 presidential election, global liquor giant Diageo ran a commercial for Buchanan’s Scotch Whisky during games 6 and 7 of the World Series. The ad contained everything you’d expect from an international booze conglomerate during a prime-time sporting event: a massive pop star, raised glasses, lifted spirits. The difference is that most people who saw the ad didn’t understand it. It was presented only in Spanish.

The ad featured reggaeton superstar J Balvin and the tagline “Es nuestro momento,” which translates to “It’s our time,” a bold statement at a particularly tense moment. While immigration was central to a heated and often nasty national debate, Diageo was embracing Hispanic culture in the U.S. as a triumph.

Alex Tomlin of Diageo wasn’t worried about a backlash. Diageo has found great success in marketing the more than 130-year-old Scotch brand to Latinos of drinking age, and consumer research told the company that young Latinos in the U.S. view themselves as the new face of America but don’t see that reflected in mainstream culture.

“As soon as the ad played, there was this incredible and overwhelming outpouring of emotion on all our social media channels,” Tomlin says. “The response was more positive than anything we’ve ever seen on any communications from the brand.”

The ad did well on paper, too. The brand saw 39 percent growth in the quarter, year over year.

What’s more, Tomlin says the success of a campaign like “Es nuestro momento” encourages creative teams and decision makers across the company’s brands to experiment with daring ideas. “It gives younger brand managers and teams incredible confidence,” he says. “It inspires them that they, too, can create great work to really connect on the biggest platforms in culture.”

50 Most Daring Entrepreneurs

44. Jim VandeHei

Axios

Axio

Betting on readers’ appetite for news

“Everyone is so hangdog about media because they know it through the lens of companies that were around 10 or 20 years ago,” says Jim VandeHei, the cofounder and CEO of digital news site Axios, which launched in January. “I never shared that hangdog view.”

Despite years of consolidation in the industry, with legacy brands struggling to offset declines in advertising revenue and cries of “fake news” sowing mistrust, VandeHei—who a decade ago left the Washington Post to cofound and grow Politico—saw 2017 as an opportune time to hit reset again. Political coverage makes up about a quarter of Axios’ content, and a controversial new president was about to take office. “There was a bit of poetry to it,” he says. “We launched Politico almost to the day of Barack Obama’s 2008 campaign announcement; we launched Axios two days before [Donald] Trump took office.” He says starting from scratch—untethered to print and able to take advantage of cheaper technology and social networks that had no traction 10 years ago—has given him access to bigger audiences than he ever imagined.

While Axios’ coverage areas—politics, tech, business, healthcare, science, and the future of work—mirror competitors’, its approach stands apart, emphasizing what VandeHei calls “smart brevity.” Stories and video from respected journalists supply scoops with a quick hit of context, rather than long-form reporting. “Most people are faking it on a lot of topics and want someone to help them be a little bit smarter, faster,” says VandeHei. On the business side of things, Axios runs punchy native ads that tell readers the “one thing” the advertiser wishes readers knew. So far, it’s working: Eleven months in, Axios—which raised $10 million in financing—was doing 60 million page views a month, and advertising revenue was more than double what it presented to investors prelaunch.

50 Most Daring Entrepreneurs

45. Marcus Wainwright

Astrid Stawiarz

Rag & Bone

Abandoning fashion’s oldest sales pitch

In February, the fashion designer announced that his brand would opt out of runway shows moving forward—essentially saying “no thanks” to the way the industry does business and press—and instead debut new collections through artful portraits and selfies. Rather than polished looks conceived of by fashion stylists, the people featured in the portraits largely selected their own outfits from the brand’s new collection and the resulting photographs were Wainwright’s way of celebrating individuality and personal style. Six months later, when it was time to debut his next offering, Wainwright once again opted out of the runway, and this time added a feel-good feature, making a donation to a charity of each subject’s choice.

50 Most Daring Entrepreneurs

46. Gina Waldhorn

Quirky

Embracing a brand best known for its bankruptcy

Quirky was an innovator’s dream, taking novice inventors’ projects from idea to market, but the high cost of manufacturing so many different types of products led it to bankruptcy in 2015. Now under the leadership of Gina Waldhorn, who previously cofounded innovation startup Evol8tion, Quirky will work exclusively with manufacturers who have expertise in given categories. Inventor royalties will decrease, but higher volumes, Waldhorn says, could earn them more. And Quirky has many inventions to choose from; more than 50,000 were submitted while the company was dormant. “The community wouldn’t quit,” she says.

50 Most Daring Entrepreneurs

47. Alexandra Waldman & Polina Veksler

Xavier Muniz

Universal Standard

Letting customers size up or down as needed

When Alexandra Waldman and Polina Veksler launched their first line of high-quality plus-size women’s clothing in 2015, it sold out in six days. But in 2017, they realized customers need more than just good clothes. “We’d see people in our showroom hesitate to buy that $120 dress because of the anxiety of not being sure they were going to stay that size,”

Veksler says. So this April, they launched a new program: Women can exchange many pieces that no longer fit within a year of purchase for their new size. Returned clothing is laundered and donated to charity. “We don’t know how this will turn out,” says Waldman, “but we felt like it was an elegant solution. We get love letters—it’s incredible!”

50 Most Daring Entrepreneurs

48. Rob Waldron & Frank Ferguson

Curriculum Associates

Giving away the company

Curriculum Associates is a K-12 education technology company whose goal is to improve how students learn. And it’s unusually committed to that goal. The company’s 91-year-old cofounder, Frank Ferguson, was ready to step away from the business but didn’t want to just sell it to a competitor. So he gave a majority share to Iowa State University—a gift valued at nearly $200 million. The university is free to sell the company and keep most of what it earns—with a catch: “I have veto power over any new owner,” CEO Rob Waldron explains. “This was a benevolent move, but it’s also allowing us to think about the mission rather than make a strategic sale.”

50 Most Daring Entrepreneurs

49. Brianna Wu

Giant Spacekat

Trading Gamergate for government

In 2014, game developer Brianna Wu became a prime target in Gamergate, a sustained harassment campaign of women in the video game industry. “It gave me very thick, rhinoceros-like skin,” she says, so now she’s trading one toxic fight for another—by running for Congress. Gunning for Stephen Lynch’s seat representing Massachusetts’ 8th District, Wu is pushing the need for cybersecurity and says government could benefit from a dose of entrepreneurial pragmatism. It isn’t about wins and losses, she says: “As an entrepreneur, we don’t get points if we get our way; we have to make it happen no matter what.”

50 Most Daring Entrepreneurs

50. Yifan Zhang

Loftium

Helping out on mortgages—with a curious catch

The mortgage industry is a big, scary, old one, with little in the way of innovation. But Yifan Zhang’s newly launched Loftium has a surprisingly fresh idea: The startup secured exclusive regulatory approval to provide down-payment assistance for home buyers, so long as they agree to Airbnb at least one spare bedroom for up to 36 months and split the additional income with Loftium. It may sound crazy (and might even be crazy!), but it’s also proving an appealing prospect for young professionals who have previously felt boxed out of the real estate market. “We’re opening a door to homeownership in expensive cities,” Zhang says, “especially for a millennial audience that’s open to sharing their homes.”

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