50 Most Daring

The 50 Most Daring Entrepreneurs in 2018

Get inspired by this year's biggest risk takers, from Elon Musk to Chance the Rapper.
The 50 Most Daring Entrepreneurs in 2018
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Magazine Contributor
15+ min read

This story appears in the November 2018 issue of Entrepreneur. Subscribe »

Entrepreneurship isn't easy. It requires bold action. We spotlight 50 entrepreneurs who dared to go big in the past year -- and who can inspire us all to dare even bigger.

Related: How to Take the Right Risks

Elon Musk

Elon Musk
Image credit: Art Streiber

CEO: Tesla and Spacex

Bold move: All of them

There's no denying that Elon Musk is a visionary. But there's also no denying that he's got room for improvement. Tesla is a well-publicized mess -- behind on production, abandoned by its executives and embroiled in an SEC investigation. Musk, too, often appears to be a mess -- increasingly erratic on Twitter, lurching from one PR crisis to the next. But in 2018, his company SpaceX launched and landed a giant rocket (and then booked the first passenger for a trip around the moon), his hyperloop technology scored a contract with the city of Chicago and his battery-making Gigafactory hit new strides. So is he a model to follow? "Beyond Musk's undoubtable genius and grit, it takes a heavy dose of hubris to devote one's life to pioneer technologies that promote the Earth's sustainability, while simultaneously creating an intergalactic escape hatch if we collectively fail to save the planet," says Leonard Sherman, a professor of business at Columbia University. "In keeping with the breathtaking ambition of his quest, Musk has certainly suffered many personal and technical setbacks along the way. But despite it all, entrepreneurs should remember Steve Jobs' words. Bold, daring entrepreneurship is messy. It's complex. But the crazy ones will get shit done." But other experts think he's more of a cautionary tale. Peter Cohan, lecturer of strategy at Babson College, urges entrepreneurs to learn from Musk's mistakes. "The lessons that entrepreneurs should take from Elon Musk are clear: Put the highest priority on what is best for your company's customers, employees, partners and investors. To do that, you must look at your strengths and weaknesses objectively. If you are not good at a skill that's critical to deliver what stakeholders expect -- now and in the future -- you should partner with an executive who is. For all of Musk's ambition and achievements, he seems unable or unwilling to do this." Still not sure? Read more of their arguments here.

Jen Rubio and Steph Korey

Jen Rubio and Steph Korey
Image credit: Courtesy of Away

Co-founders: Away

Bold move: Expanding their business from product to platform

When U.S. airlines began cracking down on smart suitcases in December 2017, banning bags with built-in batteries from planes, some luggage brands went out of business. (RIP, Bluesmart and Raden.) But Away didn't go away. Within weeks, it announced a program to swap customers' original battery modules (which had to be removed with a screwdriver) with easily removable ones for free, allowing travelers to continue using their bags without hassle.

How were founders Jen Rubio and Steph Korey able to adjust so quickly? Perhaps because it wasn't the first setback they'd navigated. Back in 2016, when they learned that their first production run wouldn't be ready for the holiday season, they created a high-end travel book and sold it with a gift card for a free suitcase, to be redeemed in February. The move worked, and it inspired a shift in how the founders think about their company.

"We knew the perfect suitcase would solve a personal pain point for a lot of people," says CEO Korey. "But it's always been about more than just luggage." In 2017, the company launched its first podcast (Airplane Mode) and a quarterly magazine (Here), and opened a buzzed-about pop-up hotel experience in Paris, timed to fashion week. By creating online and off-line experiences, Away is becoming more than a suitcase company. It's becoming a travel company.

Part of what's helped the startup succeed is a willingness to try things fast, then adjust. When customers asked for a backpack, the team didn't hole up in a studio until the design was perfect; they launched a limited-time collaboration with Karlie Kloss. "We used learnings from that collection to iterate on the design and functionality of the product before debuting it to our core collection," says chief brand officer Rubio.

And prior to launching permanent stores, Away tested a string of pop-up concepts, constantly tweaking the format and collecting every bit of feedback possible. When the doors to each permanent space opened, the team knew they would work. (And they have: Each store is profitable and has lifted regional web sales, too.) As for what's next, the cofounders don't know for sure. "The kind of brand we're creating at Away hasn't existed before, so we've embraced the inevitable ambiguity that comes with that," says Korey.

Delane Parnell

Delane Parnell
Image credit: Playvs

Founder and CEO: PlayVS

Bold move: Bringing video games to school

In October, a new activity rolled out to high schools across five states: It's e-sports, organized into competitions the same way that, say, basketball or football is. And it's all operated by one company: PlayVS, which makes software and infrastructure for e-sports leagues to compete against each other. "This is the first time in a hundred years of history and tradition where one group exclusively operates a sport for them," says Delane Parnell, the man making student gamers' dreams come true. "We get to decide the rules in which these competitions are played." It's all possible because PlayVS scored a deal with the National Federation of State High School Associations. Now it even gets to pick the games students will play. First up: League of Legends.

Tom Lewand

Tom Lewand
Image credit: Courtesy of Shinola

CEO: Shinola

Bold move: Making a very symbolic statement

The Detroit-based lifestyle brand Shinola has been releasing a series of America-themed watches for years -- but this past June, it defined "American" in a way aimed at our political moment. The brand set up cameras at a naturalization service for 100 immigrants in Manhattan, presenting them with Statue of Liberty-themed timepieces. The resulting marketing wouldn't align with some definitions of America, but CEO Tom Lewand felt the message's power outweighed any risk: "So much craftsmanship, design and innovation have come from people who started their lives in other countries and then became Americans."

Jen Gotch

Jen Gotch
Image credit: Ban.do

Founder and chief creative officer: Ban.do

Bold move: Using her fun brand to talk mental health

Related: The Complete, 12-Step Guide to Starting a Business

The founder and chief creative officer of Ban.do -- an online retailer known for its sparkly, playful products that can brighten any day -- has become an unofficial mental health advocate on social media, thanks to her brutally honest Instagram stories in which she discusses her own struggles, sharing her highs as well as her lows. But when Gotch brought that to her company earlier this year, launching a line of necklaces that read "Depression," "Bipolar" and "Anxiety," some fans of the brand were confused -- and worse, some thought she was glamorizing mental health struggles. (She wasn't: all net proceeds benefited mental health nonprofit Bring Change to Mind.) "A lot of it was my mistake, not understanding that people who follow the brand don't necessarily follow me," Gotch says. "There just should have been more forethought on my part." But plenty of the reaction was good -- the necklaces sold out in minutes, and Ban.do customers started writing in to the brand's website and social media outlets to share their own stories and struggles with mental health. "It was like the universe was telling me to wake up and pay attention," she says. "This kind of engagement is different. It just doesn't happen." Now, Gotch wants to make sure Ban.do continues this conversation with its customers. "We're charting a new course," she says. "We've always been about personal betterment and have looked at everything through that lens, but it's become a little diluted. We're just like, Here! Fun! Color! And I don't want to do that anymore. We've got a lot more to offer than just cute cups."

Boots Riley

Boots Riley
Image credit: Robby Klein | Getty Images

Director: Sorry to Bother You

Bold move: Tackling labor issues with laughs

Boots Riley is the rapper turned award-winning auteur behind Sorry to Bother You, this year's satire that hilariously (and horrifyingly) skewers corporate America. Riley's directorial debut (at the age of 47) was inspired by his past experience as a telemarketer and a union organizer. While he's thrilled with the film's critical and commercial reception, he hopes audiences see beyond its absurd laughs. "If you are a business owner -- as most of the folks reading this magazine are -- look at the reasons why you are creating your business," he says. "Explore how labor adds value to the commodities that are sold versus who gets the lion's share of the wealth. There's an injustice there that is built into the economy. We all have a place in that."

Franco Brockelman

Franco Brockelman
Image credit: Carolyn Marut

Co-founder and CEO: Releaf

Bold move: Measuring the effects of marijuana

Franco Brockelman's mother wanted to use cannabis to ease her arthritic pain, but she didn't know which strain would be best -- and neither did anyone else. Because marijuana is still largely restricted, government-sanctioned research organizations face mountains of red tape when trying to study its effects. Brockelman decided to fill the void by building Releaf, an app that collects real-time data from opt-in users. His service then finds patterns of who is helped by what and how, ultimately identifying which varieties of medical marijuana may be best for an individual's illness. "Our big-picture goal is to have the largest and most comprehensive cannabis observational study and efficacy data set in the world," says Brockelman.

Tammy Sun

Tammy Sun
Image credit: Courtesy of Carrot

Co-founder and CEO: Carrot

Bold move: Changing the conversation on benefits

For decades, fertility treatment was a luxury out of reach for most workers; most companies simply didn't include it in their benefits packages. And although Tammy Sun built Carrot's software to help companies include it, a very limited range of businesses actually got on board -- mostly wealthy tech firms like Foursquare and Coinbase. (Carrot helps companies contribute what they can to cover procedures like IVF and surrogacy, and also serves soon-to-be-expectant employees with clinic matching.) But in the past year, she's noticed a shift in culture: Employees are demanding coverage, and companies outside of tech, such as financial services and retail, are turning to Carrot for a solution. "The future of work and of fertility are closely aligned," Sun says.

Mary T. Barra

Mary T. Barra
Image credit: Courtesy of General Motors

CEO: General Motors

Bold move: Racing against Tesla and Alphabet

General Motors may be one of America's oldest carmakers, but these days it's been acting like a moonshot-taking startup. Under the leadership of Mary T. Barra, the only female at the helm of a top-10 Fortune 500 company, GM has a fresh focus on autonomous driving and car sharing, and talks of an ultimate goal of decreasing crashes, emissions and congestion to "zero." Earlier this year, GM's San Francisco-based self-driving-car subsidiary, Cruise, even won a $2.25 billion investment over the next seven years from Japan's SoftBank Vision Fund, which is Uber's largest shareholder. It's a signal that the industry giant isn't just keeping up with Silicon Valley-level innovation but leading it.

José Andrés

José Andrés
Image credit: Ryan Forbes

Chef and founder: World Central Kitchen

Bold move: Running toward a disaster -- and staying

Food has the power to change the world," says chef Jose Andres. It's a credo he lives by, and one that caused him to spring to action in the fall of 2017, when Hurricane Maria ravaged Puerto Rico. "It was not a difficult decision for me," recalls Andres. "I saw that there was a major need, and I knew that I could get involved and help. I am a cook, and we cooks are people who don't wait around to be told what to do. We just act."

Armed with $10,000 of his own money and a wallet full of credit cards, Andres found a kitchen on the island, purchased supplies and corralled enough volunteers to serve 1,000 meals on his first day there. Later, with the help of private donations and government funding from FEMA, Andres and his not-for-profit World Central Kitchen (which he founded in response to the 2010 earthquake in Haiti) would scale up to produce 150,000 meals per day from 26 different kitchens across Puerto Rico. His team has since prepared 3.7 million meals, outpacing the more seasoned disaster relief organizations like the Red Cross and the Salvation Army.

While the need for daily meals in Puerto Rico has diminished, a team from Andres' World Central Kitchen remains on the island to focus on long-term recovery, and Andres recently published a book about his experience, We Fed an Island: The True Story of Rebuilding Puerto Rico, One Meal at a Time. "We saw again and again while we were there," he says, "that a warm plate of food, prepared by and served to the community, can fill people with hope."

Jen Gurecki

Jen Gurecki
Image credit: Julianne Gauron

Co-founder and CEO: Coalition Snow

Bold move: Working very, very remotely

For 70 days this year, Jen Gurecki bicycled across Africa from Nairobi to Cape Town -- roughly 80 miles a day. And on top of that, she worked. She runs a company that makes women's skis and snowboards, and her team needs her. So why take the trip? "People spend their entire lives not doing the things they want to do," says Gurecki. But what's the point of hard work if there's no time to enjoy the spoils? Taking this on taught her a lot about effective remote working -- chiefly that it takes tremendous preparation, with months of developing systems (she used a lot of Slack and Skype) and meeting with team members to firm up relationships. After it all, she says, "everything seems doable, because I did one of the most difficult things."

Kevin Kwan

Kevin Kwan
Image credit: Jami Tarris

Author: Crazy Rich Asians

Bold move: Taking a crazy, rich, culturally significant gamble

In 2016, Netflix offered Kevin Kwan the deal of a lifetime: In a bid to turn his best-selling novel series, Crazy Rich Asians, into a film trilogy, they'd provide up-front seven-figure-minimum payouts for the movie's stakeholders. He turned them down. It sounds crazy, indeed, but Kwan wanted this film to hit the big screen. Crazy Rich Asians would be the first Hollywood studio rom-com to feature Asian leads, and the first studio movie in 25 years to have an all-Asian cast. "We needed to be able to prove to the industry that a movie like this could work," Kwan says. Hollywood studios release their box office numbers -- so if it was a hit, everyone would know. (Of course, if it was a flop, everyone would know that, too.) Netflix never shares viewership numbers, so its results would be secret. So he signed on with Warner Bros., and on the opening weekend of Crazy Rich Asians' August 2018 theatrical release, he learned he'd made the right choice. "They kept having to revise the box office estimates, because the number kept getting bigger and bigger," he says. "That's when I truly knew we had a hit."

Anne Wojcicki

Anne Wojcicki
Image credit: Courtesy of 23andMe

Co-founder and CEO: 23andMe

Bold move: Helping consumers understand their genes -- and take control of their health

Anne Wojcicki wants to give consumers affordable access to potentially lifesaving information. This March, 23andMe became the first company to receive FDA authorization to sell direct-to--consumer cancer-testing kits without a prescription. The company also recently announced plans to study the genetics of depression and bipolar disorder, and has partnered with GSK to use genetic insights to develop new medicines. "In healthcare there is a huge incentive in making money off illness, and very little incentive for preventing illness," Wojcicki says. "When people have access to their information, they can mitigate risk."

Related: 6 Types of Businesses You Can Start With Almost No Cash

Ammin Youssouf and Haweya Mohamed

Ammin Youssouf and Haweya Mohamed
Image credit: Tania Feghali

Co-founders: Afrobytes

Bold move: Getting investors to pay attention to Africa

Ammin Youssouf and Haweya Mohamed believe the future growth of the tech industry is in Africa -- but that vision isn't shared by most investors. To change perception, the duo launched Afrobytes, a series of conferences in Paris, New York, Hong Kong and other cities, which gather African innovators and international investors under one roof. "Our goal has been to bridge the gap between the African tech industry and other international communities," says Youssouf, Afrobytes' CEO. This year, top tech players like Google, Instagram and Alibaba participated in their gatherings. "It was crucial to create a tool for people of African descent to get back their narrative," says Mohamed.

Doug Brenneke

Doug Brenneke
Image credit: Courtesy of Belden

VP of research and development: Belden

Bold move: Providing drug rehab to job candidates

Most companies turn away candidates who fail drug tests. Belden's manufacturing plant in Richmond, Ind., welcomes them. Spearheaded by Doug Brenneke, Belden's VP of R&D, the company's new Pathways to Employment program offers rehabilitation therapy to any successful candidate who tests positive for drug use and promises them employment after completing the program. "We felt a responsibility to take action on an issue that was affecting our community," says Brenneke. "It was impacting our [local] talent pool. We saw a need to address the shortage of workers available."

Gordon Hartman

Gordon Hartman
Image credit: Courtesy of Morgan's Inspiration Island

Founder: Morgan's Inspiration Island

Bold move: Building an amusement park for everyone

Gordon Hartman had already made a first-of-its-kind place: In 2006, inspired by the needs of his physically and cognitively challenged daughter's struggle to make friends at a swimming pool, he called together a group of passionate people -- doctors, therapists, teachers, parents of special--needs children -- "to come up with big ideas," says Hartman. In 2010, he opened Morgan's Wonderland, an ultra--accessible theme park in San Antonio for kids of all abilities. Last year, he came full circle, expanding the successful concept to a water park: Morgan's Inspiration Island, with waterproof wheelchairs, a splash pad for those sensitive to the cold and other inclusive features.

Tim Ellis and Jordan Noone

Tim Ellis and Jordan Noone
Image credit: Courtesy of Relativity Space

Co-founders: Relativity Space

Bold move: Sending a 3-D-printed rocket to space

Tim Ellis and Jordan Noone, college buddies who got their start at USC's Rocket Propulsion Lab, believed they could 3-D-print an entire rocket made of only 1,000 parts -- instead of the typical 100,000. To get their venture off the ground, the pair cold-emailed Mark Cuban to ask for funding. Three years later, they have raised more than $45 million in three rounds of funding (all of which Cuban participated in) and recently announced a partnership with NASA, with plans to launch their first rocket by 2020. "Starting any company is mind-bendingly difficult," says Ellis, Relativity Space's CEO. "A rocket company, extra so. And then a 3-D-printed-rocket company using technology no one has ever developed before, and having to reinvent processes people have relied on for 60 years in building aerospace products? It was borderline crazy."

Julie Wainwright

Julie Wainwright
Image credit: Margot Duane

Founder: The RealReal

Bold move: Convincing luxury fashion brands to embrace a secondhand seller

When making her investment pitch for The RealReal, Julie Wainwright sensed that investors saw four strikes against her: "I was a woman, old enough to be most of their mothers, I wanted to launch a fashion business and I wanted to use an unproven concept," she says. "I knew I'd hear a lot of noes." And she did. But she also had a laser-sharp vision: to bring the luxury consignment market online, handling authentication, appraisals, shipping and sales.

Wainwright is the former CEO of Pets.com, so her background in e-commerce gave her some competitive insight. She suspected that the operation of a secondhand luxury fashion market would prove unattractive to Amazon. She also knew that eBay was cluttered with knockoffs and bad photos. So in March 2011, having failed to hook investors, Wainwright bootstrapped her site and began shipping purchases that June. In the first year, the business did $10 million in sales. "Let's say investors were more interested after that," she says, laughing.

Fast-forward seven years, and The RealReal has raised more than $288 million, grown to a team of more than 1,600 and has a brick-and-mortar retail store on each coast. (Wainwright hints that business is so brisk, a retail expansion is now under way.) But as much as those figures may raise eyebrows in Silicon Valley, it's The RealReal's recent campaign partnership with designer Stella McCartney that's earned the attention of global fashion brands. The initiative -- called The Future of Fashion Is Circular -- marks the first time a luxury brand is actually encouraging consignment rather than turning up its nose at it. When customers consign any Stella McCartney item to The RealReal, they receive $100 to shop at Stella McCartney stores.

"A strong secondary market really does support the primary market," says Wainwright. "When people start consigning, they have more room in their closet and more money in their pockets -- and they tend to buy new things that they know they can ultimately resell." Whenever that moment comes, The RealReal will be waiting.

Daniela Perdomo

Daniela Perdomo
Image credit: Gary He

Co-founder and CEO: goTenna

Bold move: Taking on the telecom giants (when they're at their least useful)

Brazilian-born Daniela Perdomo was living in Brooklyn in October 2012 when Hurricane Sandy struck, leaving large swaths of New Yorkers without power and internet service. "Even in this hyperconnected place, you couldn't get through to anyone," she says. "I remember thinking, Our smartphones are amazing, but without a signal they're just really expensive calculators."

Rather than gripe about the communication gap during times of crisis, Perdomo decided to do what telecom giants couldn't: Close it. She co-founded goTenna with her brother, Jorge, and set out to create "the most scalable, completely mobile mesh architecture that's ever existed." The resulting candy--bar-size piece of plastic, which pairs with a cellphone via Bluetooth, uses radio waves to send and receive text messages and GPS locations up to four miles without the use of cell towers, wi-fi or satellites. The first iteration launched in 2015, and in 2017, goTenna introduced a game-changing upgrade: goTenna Mesh, which adds on mesh-networking capability. Each goTenna acts as a node in a network. The more nodes in your vicinity, the more your range expands and the stronger and more reliable your communications become.

It's tempting to liken the handheld device to a long-range walkie-talkie, but it's decidedly more sophisticated. With a walkie-talkie, messages are broadcast to the public and interfere with everyone's airwaves. But with goTenna, hundreds or thousands of people can send targeted, encrypted communication at once -- without straining the network. More than 100,000 have been sold, and the startup has raised $16 million-plus in funding to date.

Last September, when Hurricane Maria ravaged Puerto Rico, volunteers set up public goTennas so residents could call hospitals for medical help, coordinate supply deliveries, and reassure loved ones they were safe. "It was like I saw everything come full circle," Perdomo says. "These events feel extraordinary, but they're not -- they happen somewhere almost every day. And we should be asking more questions about the resilience of our infrastructure."

Edward Stack

Edward Stack
Image credit: Mike Coppola | Getty Images

CEO: Dick's Sporting Goods

Bold move: Sacrificing sales for safety

In the wake of the Parkland, Fla., shooting in February, activists pressured major retailers to stop selling assault-style rifles and high-capacity magazines. Such calls have come and gone before, but this time an unexpected brand agreed. Dick's Sporting Goods said it would no longer sell the items, and would no longer sell firearms to anyone under the age of 21. Hunting products make up about 10 percent of the company's sales, but CEO Edward Stack was willing to take the hit. "Following all the rules and laws, we sold a shotgun to the Parkland shooter in November 2017," he wrote in a letter explaining the decision. "It was not the gun, nor type of gun, he used in the shooting. But it could have been."

Russell Ladson

Russell Ladson
Image credit: Leyla Ismen

Co-founder and CEO: Drop

Bold move: Building virtual reality's infrastructure

The AR/VR marketplace has become crowded by startups promising to transport users to far-off experiences. But Russell Ladson is thinking closer to home. "We asked ourselves what a browser looks like in a post-smartphone world, when we all have augmented and virtual reality headsets," says Ladson. His app, Drop, offers VR and AR users an immersive way to explore the internet. (Imagine your browser, but as a 360-degree environment.) That's earned investment from HTC, which will make Drop a launch partner in HTC's new Vive Focus headset. But Ladson really sees Drop as a core utility tool for developers. "This enables an ecosystem for even more AR and VR experiences," he says.

Related: Risk or Uncertainty: Which Is Better to Face?

RJ Scaringe

RJ Scaringe
Image credit: Courtesy of Rivian

Founder and CEO: Rivian

Bold move: Going stealth -- for seven years

Back in 2011, RJ Scaringe started an electric vehicle company with one ambition: build a sporty car, and become quickly known. But after raising some money and hiring a team, he asked himself a question. "Why did we exist?" he says. Tesla already did what he'd set out to do. So he pivoted to electric SUVs and trucks built for adventures, and worked quietly for years. "We wanted to make something real first," he says. This month, the secret is out: Rivian will debut vehicles at the Los Angeles Auto Show. The team is excited but adapting. "We've built muscle memory on being stealth," says Scaringe. "Until three weeks ago, we didn't have a sign on our door."

Patrice Louvet

Patrice Louvet
Image credit: Courtesy of Ralph Lauren

CEO: Ralph Lauren

Bold move: Making a classic fashion brand cool again

In 2017, Patrice Louvet walked away from a 25-year career at Procter & Gamble to join Ralph Lauren, a 50-year-old clothing company struggling to reclaim its "cool" factor. To make Ralph relevant again, Louvet is building off what he learned reviving brands like Pantene and Clairol -- but of course, he's now working at a higher price point. To that end, one of his first moves was to pull stock from 25 percent of all department stores -- part of his war on markdowns, which he believes have cheapened the brand. Louvet is also overhauling digital efforts, rebooting e-commerce, developing "smart" in-store changing rooms, hiring a digital chief, and fleshing out the board with Apple and Etsy executives.

Reese Witherspoon

Reese Witherspoon
Image credit: Jon Kopaloff | FilmMagic | Getty Images

Founder: Hello Sunshine

Bold move: Proving that women will watch -- and read, and listen

Everyone knows Reese Witherspoon can make a good movie. The Academy Award--winning actress long ago proved her production chops with the films Gone Girl and Wild. But in 2016, Witherspoon launched production company Hello Sunshine to create wide-ranging content for women and in the past year alone announced a podcast network with Rooster Teeth, an Oprah-style book club and partnership with Audible and a brand-new VOD television channel. With every project, Witherspoon is investing in her big-picture goal: proving that women are valuable, hungry consumers of content.

Cindy Chin and Alexandra Levin Kramer

Cindy Chin and Alexandra Levin Kramer
Image credit: Lyanlex Bernales Photography & Courtesy of CKR

Co-founders: Women on the Block

Bold move: Staking a claim to blockchain

Pick any random tech company and a majority of the time, the executive teams are men," says Cindy Chin, CEO of the consultancy CLC Advisors. "Blockchain and crypto-currency are no different." Upset by the lack of recognition for women in crypto, Chin teamed up with CKR Law partner Alexandra Levin Kramer to put the spotlight on the hundreds of women already thriving in cryptocurrency and blockchain. They gathered an all-women panel and launched Women on the Block, the first all-female blockchain conference; proceeds supported women in technology. "You see the gaps everywhere," says Chin. "The time to close those gaps is now."

Chance the Rapper

Chance the Rapper
Image credit: Daniel Boczarski | Getty Images

Musician

Bold move: Tackling an industry harder than music

Local news can be a revolving door of disappointment. Big-money players come in to buy a local news property, like when TD Ameritrade founder Joe Ricketts bought DNAInfo and Gothamist, and then walk out a little poorer...like when he folded both those properties in 2017. But this past June, Chicagoist (the Chicago offshoot of Gothamist) found an unexpected savior: Twenty-five-year-old hip-hop artist Chance the Rapper, the sole winner of a Grammy for a streaming--only album, bought and relaunched the news site. He says he sees it as an opportunity to give "the people of Chicago an independent media outlet focused on amplifying diverse voices and content."

Evita Robinson

Evita Robinson
Image credit: Pete Monsanto

Creator: Nomadness Travel Tribe

Bold move: Busting stereotypes, in transit

This past summer, Oakland, Calif., played host to the first-ever travel festival for millennial travelers of color -- which created what organizer Evita Robinson admits were some unexpected sights. "So all of a sudden, there's this park in the middle of Oakland, and you see black people rock climbing," she says with a laugh. Members of this demographic have been stereotyped as non-travelers, but statistics show that the black community is traveling in increasingly higher numbers -- so Robinson is taking the lead. Her company began as an online community but evolved into an event producer, consultancy and retailer focused on millennial travelers of color, attracting 21,000 members and partnerships from big brands like GoPro, Hyatt and Airbnb. "We're all about breaking stereotypes and doing things they say people who look like us don't do, because we know it's bullshit."

Misha Nonoo

Misha Nonoo
Image credit: Courtesy of Misha Nonoo

Founder and CEO: Misha Nonoo

Bold move: Going lean in an industry of excess

Misha Nonoo used to be like every other fashion creator: She'd make clothing and then wind up with inevitable extra inventory at the end of each season. Brands from Burberry to H&M just destroy their extras; Nonoo couldn't stomach the thought. In the fall of 2017, she rebuilt her business to ensure there'd be no overstock. Everything would be on-demand, with clothes ordered, produced, shipped and delivered in just five days. "I didn't have a backup plan," she says. "If it didn't work, the business would have failed entirely." But it did work -- in large part because the change forced her to focus on fewer items. Now nearly 80 percent of revenue comes from her Easy 8 collection, eight pieces that mix and match to form a full wardrobe.

Jon Schlossberg

Jon Schlossberg
Image credit: Courtesy of Even.com

Co-founder and CEO: Even

Bold move: Solving our workforce's greatest challenge

About 78 percent of Americans live paycheck to paycheck, which makes them vulnerable to payday lenders and overdraft fees. "Those businesses are hurting people," says Jon Schlossberg. He envisioned a platform that would help people budget, save and get an advance on their paychecks without punishing interest rates. That would require working with employers and banks -- and in December 2017, he got his test case: Walmart made his app, Even, available to its employees. More than 250,000 people signed up, and 75 percent use it every week. Now other companies want it -- and Even is hustling to meet the demand.

Emily Orrson

Emily Orrson
Image credit: Keith Johnson

Senior product marketing manager: Minecraft

Bold move: Asking gamers to step out of the game

Can video games save the ocean? Emily Orrson thinks it's worth a shot. When Minecraft -- the online video game in which users create 3-D worlds -- introduced an ocean-themed update this year, the product marketing manager saw an opportunity to do even more. She launched the Coral Crafters project and partnered with gamers, YouTubers and an elementary class in Monterrey, Mexico, to design real-life structures that were placed off the Cozumel coast. They're made from Biorock, a material that can regenerate coral. "Minecraft players are already using the game to code and design public spaces," says Orrson. "This is an opportunity to engage that initiative."

Fatima Goss Graves

Fatima Goss Graves
Image credit: Courtesy of Times Up Now

Co-founder: Time's Up Legal Defense Fund

Bold move: Heading into battle for women everywhere

In October 2017, allegations of Harvey Weinstein's repeated sexual abuse and harassment led to a chorus of #MeToo stories from women across the country. Household--name actresses, directors and writers -- including Eva Longoria, Shonda Rhimes and America Ferrera -- then came together to form the Time's Up movement to fight continued abuse. And because they wanted to help women far beyond the Hollywood Hills, they enlisted someone they trusted to never stop fighting: Fatima Goss Graves, the CEO of the National Women's Law Center. Goss Graves helped form the Time's Up Legal Defense Fund, which provides legal assistance to women in need. "Since launching [in January 2018], we've heard from more than 3,500 individuals seeking our assistance," she says. "To give perspective, in October 2017 we received about 20 calls a week about harassment -- and we thought that was a lot." It goes to show, she says, that this is not an isolated problem but an ongoing one that needs a significant amount of support. The fund has raised $22 million and assembled a network of 700 attorneys, but there's still work to do. "As large a number as $22 million is, it's not enough to meet the need," she says. So Goss Graves and her team are working to activate their supporters. "We obviously have not reached a place where institutions have made the sorts of reform systematically so that we aren't going to deal with this kind of abuse and these kinds of stories again and again," she says. "So we continue to engage with donors, including small donors. I've been most impressed with people who have gotten together in small groups and held their own fund-raisers to support us." Donations have been in quantities as small as $5 or $10, she says, but every penny counts -- and makes a strong statement. "What they're doing with that small donation is saying, 'I want to be a part of change,' " she says.

Dara Khosrowshahi

Dara Khosrowshahi
Image credit: Courtesy of Uber

CEO: Uber

Bold move: Taking on tech's biggest PR challenge

In 2017, when Dara Khosrowshahi first heard about the CEO opportunity at Uber, he wasn't interested. His predecessor, co-founder Travis Kalanick, had resigned amid a host of scandals including a toxic work culture, systemic sexual harassment and a customer boycott in response to Kalanick's seat on President Trump's economic advisory council. Khosrowshahi knew it would be a lot to take on, and a lot to clean up. And anyway, he was happy in his current position at Expedia. But talking things over with a friend changed his mind. Khosrowshahi realized that pivoting to lead Uber wasn't about being "happy" -- it was about doing something great. "My career advice to people has always been: Look for opportunities where you can make a difference at companies that are making a difference in the world," Khosrowshahi says. "Uber clearly checked both boxes." Now, just more than a year later, Khosrowshahi has used employee input to create a new list of cultural values and hired the company's first ethics officer. He has also directed efforts toward bettering Uber's damaged relationship with the public through ads emphasizing the company's new direction and the implementation of an in-app emergency button for customers. Khosrowshahi is attempting to orchestrate one of the highest-profile company turnarounds in tech history, and he now has his eye on taking Uber public -- possibly as soon as 2019. "You need to make big, bold bets, even if it sometimes means failing," he says. "[That's] how companies avoid being disrupted -- you have to be willing to disrupt yourself."

Nayrouz Talaat

Nayrouz Talaat
Image credit: Ahmed Gamil

Founder: Direxiona

Bold move: Building an all-female driving school -- in Egypt

When Nayrouz Talaat, a Cairo-based journalist, wanted to learn to drive, she had a hard time finding anyone that could teach her: all instructors were male, and she didn't feel comfortable or particularly safe spending that much time alone with an unfamiliar man. She convinced her uncle to instruct her, but knew that many other women in Egypt must feel the same way. So in 2016, she launched Direxiona, a startup employing female driving instructors who teach female students exclusively. "We seek to empower women on the road," Talaat says. "Women in Egypt prefer to learn with other women for security reasons, but it's tough to find professional female drivers, who quickly and unfairly get stereotyped as bad drivers." She's since expanded to 12 neighborhoods across Cairo, and has even started attracting Saudi women who sign up for lessons while visiting the country. Talaat now employs 50 female instructors and serves at least 100 students each month; she expects to triple the size of the company by the end of 2019. In the past year, Direxiona has competed in startup competitions and summits in Egypt and parts of Europe, picking up mentors for Talaat and her team. "At Direxiona, we know very well that it is hard to maintain the success of a women-only startup in a conservative, male-dominated society like Egypt," Talaat says. "But we are adamant about completing our mission to empower women here -- both in the region and on the road."

Related: 5 Ways Mark Zuckerberg Took Risks, for Better or Worse

Morgan DeBaun

Morgan DeBaun
Image credit: Courtesy of Blavity

Co-founder and CEO: Blavity

Bold move: Pushing hard into new media

At a time when news media budgets are shrinking and established publications are getting rescued by tech billionaires, Morgan DeBaun's Blavity, a platform focused on black millennials, is thriving. This summer, she raised $6.5 million from investors like Google Ventures and Comcast Ventures to expand Blavity's empire, which now includes 21Ninety, a lifestyle site for women of color; Shadow & Act, a Hollywood Reporter-esque trade; and Travel Noire, an Instagram brand that Blavity acquired and turned into a bustling travel-and-leisure resource. "We set out to rethink what it means to be a distribution platform for black creativity," says DeBaun. "We're empowering a generation of storytellers."

Oscar Munoz

Oscar Munoz
Image credit: Justin Sullivan | Getty Images

CEO: United Airlines

Bold move: Staying, when everyone said to go

United Airlines last year suffered a seemingly unending onslaught of public relations catastrophes. There was, of course, the violent removal of a passenger from an overbooked flight. Then came news that 75 percent of all animal deaths on planes that year were on United flights. Many called on CEO Oscar Munoz to resign, but he stayed put -- and genuinely got to work fixing problems. First up: Improve customer service with a new employee training regimen, as well as a $10,000 incentive for passengers to voluntarily forfeit seats on overbooked flights. Munoz's efforts are keeping United flying high: As of Q2 this year, United had made enough of a comeback to repurchase $407 million worth of its stock.

Jen Horonjeff

Jen Horonjeff
Image credit: Courtesy of Savvy

Founder and CEO: Savvy Cooperative

Bold move: Looking beyond loyal customers

Medical industry conferences often have a "patient representative" sitting on panels, voicing the needs of the patient. And for a long time, that person very often was Jen Horonjeff. She was a patient-centered outcomes researcher at Columbia University Medical Center, and has had juvenile arthritis since infancy. "I was happy to help, but I also wanted more diverse voices than just mine represented," she says. When she suggested that panel organizers broaden their reach, many said they didn't know where to look. That's when Horonjeff realized: The medical industry may treat patients, but it doesn't do a good job of hearing from them.

Horonjeff figured she could fix this problem. First she reached out to her own networks and found a flood of patients eager to have their voices heard. Then she partnered with Ronnie Sharpe (who grew up with cystic fibrosis and founded a social network for others with the disease), and in 2017 the two officially launched Savvy Cooperative. The platform connects patients with healthcare companies, startups and researchers eager to reach them for focus groups, user testing, surveys, and one-on-one interviews. In the first year, patient "gigs" (as the engagements are called) ranged from testing a wearable device prototype to participating in a market research panel on metastatic breast cancer.

From the start, Horonjeff and Sharpe settled on a co-op model: Anyone can participate, but if people buy a share of the business (for $34), they're a member. The more active members are -- meaning the more gigs they complete -- the larger their portion of the profits at the end of the year. "We didn't want to perpetuate the power dynamic of a small number of people benefiting from a large number of people doing all this work," she says. "Patients should have a voice in what we do, and they should be compensated for sharing their info."

John Foley

John Foley
Image credit: Courtesy of Peloton

Co-founder and CEO: Peloton

Bold move: Doubling down and doubling the price

In just six years, John Foley built a $4.15 billion company by selling a $2,000 stationary bike and streaming boutique fitness classes to living rooms. In early 2018, just as copycats were jumping on the indoor-cycling-at-home bandwagon that Foley built, he picked up the pace. Peloton announced Tread, an at-home treadmill that streams running-based, full-body workout classes (similar to Barry's Bootcamp). It costs $4,000, a price tag that doubters scoffed at, but presales skyrocketed anyway. Foley wasn't surprised. "The treadmill market is five times bigger than the bike market, and customers were asking for it," he says.

Daniel Ek

Daniel Ek
Image credit: Courtesy of Spotify

CEO: Spotify

Bold move: Going public -- without investment banks

When the music-streaming giant went public earlier this year -- a year that, to be kind, has been mixed for tech stocks -- CEO Daniel Ek didn't take the traditional route of working with investment banks to set an initial offering price. Instead, he bypassed Wall Street completely and went public via direct listing, letting the market figure out a fair price on its own. (Spotify didn't need to raise money, so this ultimately saved it unnecessary underwriting costs.) While many expected the company's shares to spike and crash repeatedly as a result, the offering was surprisingly calm: Shares opened at $165.90 and have since climbed consistently, a result that may inspire other startups to ditch the big banks and go direct.

Mindy Grossman

Mindy Grossman
Image credit: Courtesy of Weight Watchers

President and CEO: Weight Watchers

Bold move: Looking beyond loyal customers

This isn't your mother's Weight Watchers.

When Mindy Grossman took the helm of the 55-year-old company in July 2017, she knew the brand needed a healthy makeover of its own. It felt dusty, like the product of a bygone era. So to start, the CEO set about upending common misconceptions about the program. No, you don't have to buy the food. You don't have to attend the meetings. And very critically: Weight Watchers is not only for female clientele of a certain age.

"When you have a heritage brand, you have to myth-bust what you were versus what you are today," says Grossman. "How do you get people to understand that this is a program for them? You have to partner with others who share the same goal -- to inspire people to lead healthier, better lives."

That goal has led Grossman to make decisions that, even just a few years ago, nobody would have imagined from Weight Watchers (including a just-announced name change to WW). For example, through an acquaintance with Roc Nation president Michael Yormark, Grossman had an unexpected meeting with someone who was newly focused on his health: rapper and producer DJ Khaled, who had recently welcomed a son. "He kind of had a revelation and really wanted to be healthier for his son and set a good example," Grossman recalls.

On New Year's Day 2018, Weight Watchers announced its partnership with Khaled. Utilizing his vast social reach -- 11 million Instagram followers and four million Twitter followers -- the 43-year-old DJ would document his progress on Weight Watchers' just-launched WW Freestyle program. "It's been so incredibly positive," Grossman says, "in people both supporting him and saying, 'I want to do this, too.' "

Weight Watchers has since added to its ranks of male brand ambassadors with chef Eric Greenspan and actor-director Kevin Smith, and Grossman has credited these new voices with helping the company achieve a 29 percent subscriber increase year-over-year in the first quarter of 2018.

"We're seeing more men in the program, more diversity, [and] a lot more conversation around the brand in the cultural vernacular," says Grossman. "And that's what's important to us."

Ginni Rometty

Ginni Rometty
Image credit: Christophe Morin | Getty Images

CEO: IBM

Bold move: Redefining Big Blue

Decades have passed since IBM was regarded as a buzzy tech company, but it recently notched a third consecutive quarter of revenue growth after more than five straight years of decline. This Lazarus-like comeback was built around the behemoth's "strategic imperatives" -- its new analytics, cloud, mobile, security and social divisions, which now account for almost half IBM's total revenue. When someone mentions Big Blue today, they're more likely to be discussing artificial intelligence and blockchain than mainframes and servers.

This is just the start for the rebooted company, according to its CEO, Ginni Rometty, who told this year's IBM Think conference in Las Vegas that its latest transformation is in perfect sync with the data analytics revolution. "Probably only once every 25 years, business and technology architecture change at the same time," she told the assembled business leaders in Nevada. "When you put AI together with data, you get something more profound. You get exponential learning. I believe this is the ultimate competitive advantage."

IBM has already become a major player in blockchain, which Rometty is convinced "will do for trust and transactions what the internet did for information." It is one of the drivers of the Hyperledger, a group of businesses committed to building open-source blockchain technologies, and it has unveiled several other industry initiatives. IBM Food Trust is a collaboration with 10 leading food producers and retailers to highlight the "most urgent areas" in the global food supply chain.

Such ventures add credence to IBM's claim that business culture now has more in common with a startup than an organization with more than 360,000 employees. Under its yearly Global Technology Outlook initiative, every project team is encouraged to present ideas in January, the most promising of which help the corporation decide which new areas to invest in for the following year. The blockchain division, in fact, was created as soon as it was discovered that two separate teams were approaching the technology from two completely different perspectives.

Reggie Fils-Aimé

Reggie Fils-Aimé
Image credit: Patrick T. Fallon | Getty Images

President and COO: Nintendo of America

Bold move: Boosting sales of a high-tech product with...cardboard

In March 2017, Nintendo introduced the Switch -- a small, portable gaming console that became an instant hit, selling nearly 18 million units in a year and skyrocketing revenue 500 percent. To keep up that momentum, Nintendo created a lo-fi accessory: a line of cardboard--cutout kits called Labo, which, when assembled, turn the Switch into interactive objects like guitars and robots. North American president Reggie Fils-Aime has said that Labo will not only help keep fans engaged but attract new consumers who are less familiar with gaming and interested in the build-it-yourself aspect of the product.

Glenn Chamandy

Glenn Chamandy
Image credit: Courtesy of Gildancorp.com

President and CEO: Gildan Activewear

Bold move: Creating a future for a seemingly broken brand

When American Apparel collapsed -- spurred by years of scandal and financial struggle -- it seemed nobody would touch such damaged goods. Then came Glenn Chamandy, CEO of T-shirt company Gildan, who scooped up American Apparel at auction in 2017. He has since relaunched with a focus on digital sales (just one store exists to test product), expanded internationally, moved production overseas and improved sizing. The brand was once notorious for its sexy ads, and Chamandy kept the vibe but lost the raunch. Now the world will see: Can a brand outlive its controversy?

Brad Haley

Brad Haley
Image credit: Courtesy of IHOP

Chief marketing officer: IHOP

Bold move: Playing a name game

This past June, IHOP did what brands -- and especially big, play-it-safe brands -- rarely do intentionally: It created confusion. The company announced that it would change its name to IHOb and a week later revealed that the b stood for its new burgers. (Soon after, it admitted the whole thing was a gag.) The campaign was designed to drive post-breakfast business, and although some consumers felt hoodwinked, IHOP felt victorious. "We were top of mind for a lot of people for a long time," says chief marketing officer Brad Haley. The company says it earned north of 40 billion media impressions, but more important, burger sales quadrupled. "If you're going to do something that's brave and daring, it's got to be fun," says Haley.

Marcia Kilgore

Marcia Kilgore
Image credit: Victoria Stevens

Founder: Beauty Pie

Bold move: Lowering prices, then capping sales

Marcia Kilgore has mastered women's cupboards. But the creator of Bliss Spa and Soap and Glory took on her greatest challenge with the launch of Beauty Pie. Most brands sell products at a 1,000 percent markup; Kilgore wanted to slash prices. So she developed products at high-end labs and sold them at drugstore prices thanks to direct sales, membership fees and no expensive marketing campaigns. "First thought was, Industry people are going to hate me," Kilgore says. "Then I realized that women were going to love me." To dissuade resalers from profiting off her prices, Kilgore implemented purchase caps -- starting at $100 of product per month, per person -- to keep her mission pure, even if it meant sacrificing overall sales.

Travis Montaque

Travis Montaque
Image credit: Courtesy of Emogi

Founder and CEO: Emogi

Bold move: Branding consumers' conversations

Travis Montaque wanted to make messaging more meaningful. Text a friend that you want coffee, and his smart emoji app will recommend sending them a coffee-cup sticker. In 2017, he pushed the limits and welcomed brands into the conversation. Now that recommended coffee-cup emoji would be branded with McDonald's McCaf? moniker. "There was a question of whether consumers would be receptive," Montaque admits. But users actually selected branded stickers at a higher rate than non-branded. The startup's client roster has since grown to include Tide, Ikea and Bose, and in May, the company raised a $12.6 million Series A.

Arlan Hamilton

Arlan Hamilton
Image credit: Courtesy of Back Stage Capital

Founder and managing partner: Backstage Capital

Bold move: Not waiting for the tech industry to change

Less than 1 percent of venture-backed founders are black, and female founders received just 2 percent of venture capital in 2017. That's why, in May, Arlan Hamilton announced via Twitter -- with a GIF from Beyonc?'s "Formation" -- that her firm, Backstage Capital, was raising a $36 million "It's About Damn Time" fund to invest in companies founded by black women. She's since created Backstage Studio so she and her team can launch products of their own, further challenging tech's status quo. "A no is just one step closer to the next yes," Hamilton said earlier this year. "One step closer to what I want."

Baiju Bhatt

Baiju Bhatt
Image credit: Bonnie Rae Mills

Co-founder and co-CEO: Robinhood

Bold move: Embracing crypto's ups and downs

Within four days of announcing its cryptocurrency--trading feature in February, Robinhood -- the zero-fee trading app -- had signed up more than one million users for its waitlist. They'd trade crypto using a neon interface, a departure from the design Robinhood uses for stocks. "It was a branding risk," says Baiju Bhatt, co-CEO. But it was more than that: With five million customers, a valuation of $5.6 billion,\ and consumer skepticism toward cryptocurrency, launching into the ever-volatile crypto world could have slowed Robinhood's momentum. Instead, the company is working toward an IPO in the coming years.

David Jackson

David Jackson
Image credit: Courtesy of Fairmont Private Schools

President: Fairmont Private Schools

Bold move: Refunding students' tuition if schools don't deliver

David Jackson knows Fairmont Private Schools provide a top-notch education. The Southern California network of private P-12 schools has sent graduates to top-100 colleges for more than 10 years. "So I made that part of our guarantee," Jackson says. In 2017, he launched the "College Promise": If students who've graduated from Fairmont's high school don't get into a top-200 college or university, they get half their high school tuition back as a scholarship for college. "People thought I was crazy," he says. "But we're already delivering. What are you worried about?"

Jeff Gennette

Jeff Gennette
Image credit: Shawn Ehlers | Stringer | Getty Images

CEO: Macy's

Bold move: Saving hundreds of stores by focusing on 50

When Jeff Gennette seized the reins at Macy's in 2017, the company was in a deep funk. It wasn't just that brick-and-mortar was yielding to e-commerce -- even the newly promoted CEO recognized that the once-famed department stores, crammed with dull and discounted stock, were drowning in a "sea of sameness."

And yet today, 20 months later, Macy's is surpassing expectations. While second-quarter sales were flat at $5.6 billion compared with the year-earlier period, net income was $164 million, up from $108 million in the second quarter of 2017.

How? This has been achieved partly through Gennette's "Growth 50" strategy -- improving the ambience, service, and products inside Macy's best 50 stores (out of 670), while shuttering underperforming ones. It was a move fraught with risks, as a company essentially played favorites within its own organization, surely disappointing or spooking stores outside the favorite 50.

At the same time, Gennette embarked upon other major changes. He invested heavily in mobile and e-commerce. And just as significantly, Gennette modernized Macy's culture, bringing in scrappier entrepreneurs. This year the company took a stake in Silicon Valley startup b8ta, which now showcases trendy gadgets at The Market @ Macy's, a new pop-up concept. It also acquired cult New York concept shop Story, naming its founder, Rachel Shechtman, brand experience officer for the department store; her brief is to woo edgier brands and create more contemporary in-store experiences.

Macy's is also rolling out the stand-alone beauty chain Bluemercury, which it bought in 2015 and is gradually bringing inside department stores. In doing so, Macy's gets to capitalize on one of retail's most dynamic sectors, while also connecting with younger, social-media-savvy customers who likely wouldn't dare stop at a stodgy old beauty counter.

"It is encouraging to see the continued strengthening of our brick-and-mortar business, where we saw trend improvements across the portfolio, led by our Growth 50 stores," Gennette said on a recent earnings call. Nevertheless, he acknowledges that Macy's will not succeed long-term without "robust e-commerce" and the "great mobile experience" he is also committed to developing. But for now, the CEO is upbeat. "Our strategic initiatives are gaining traction," he notes. "We have momentum."

 

 

Shortly after going to press, one of the entrepreneurs included in our 50 Most Daring list was terminated by his company and sued for various alleged corporate misdeeds. We have removed that person from the online version of the list. Therefore, this list represents 49 of the 50 entrepreneurs that appeared in our November, 2018 issue.

 

 

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