Meet the 20- and 30-something founders behind 2019's online retail unicorns: Glossier, Rent the Runway, Casper, and Away

Amy Larocca of The Cut hailed Weiss as the "millennial Estée Lauder." Weiss, she said, realized that social media was "transforming the way beauty products were talked about and bought" and intended to disrupt the industry.

With only 29 products, Glossier focuses on a "no-makeup" look. The brand is known for its signature pink hue, playful marketing voice, and images of diverse women with minimal makeup, reported Mary Hanbury for Business Insider.

Weiss' interest in fashion started young. At age 10, she showed up to school "in thigh-high stockings, a plaid miniskirt from Contempo Casuals and loafers, and ... [with] a feather-topped pen," she told the Business of Fashion.

While interning at Teen Vogue, she was featured alongside Lauren Conrad in the US TV show "The Hills." After graduating in 2007, Weiss worked briefly for W magazine before moving on to become a fashion assistant Vogue, according to Lauren Indvik for Fashionista.

"I was surrounded by so much magic … All these models and makeup [artists]," she told Indvik. She said she noticed a gap in the market for beauty product coverage, which inspired her to launch the blog Into the Gloss.

It soon became popular among beauty mavens who commented on the posts to share their beauty experiences and recommendations, reported Hanbury.

A year in, Into the Gloss was raking in 10 million page views per month, according to Alyssa Giacobbe of Entrepreneur. With a handful of corporate partnerships and a small staff, Weiss quit her job at Vogue to focus on the blog full-time. She re-launched the website and upped the number of posts only to see traffic to the site triple overnight, wrote Hanbury.

Thrive Capital, previous investors in Warby Parker and Instagram, led the company's $8.4 million Series A funding round in November 2014, reported Raisa Bruner for Business Insider.

Glossier set itself apart by committing to brand identity and depending on its user community and feedback to innovate and iterate, Bruner wrote. "Brand is really, really important. It's kind of everything," Weiss told her.

"There are a handful of beauty conglomerates, and it's difficult for them to innovate," she added. Weiss said she spends all day on her smartphone and social media, checking out YouTube beauty tutorials and Instagram snaps."Beauty has really gone online, because that's where the customer is."

Weiss teased the new brand on Instagram about four weeks before launch, reported Elizabeth Holmes for The Wall Street Journal. Within the first week of selling the new products, she had more than 18,000 followers, Holmes wrote. Instagram influencers and celebrities such as Karlie Kloss helped spread the message, posting photos of themselves in Glossier swag.

Instead of aiming at wholesale, Weiss intended to crowdsource — through social-media platforms, affiliate sponsorships and links, and gossip, Larocca reported. As Gaby Del Valle of Vox put it, Glossier's success lies in treating its customers like influencers.

To market a new blush, Cloud Paint, Weiss hired makeup artists to use it on Oscar-attending celebrities and post the results on social media, according to Giacobbe — regrams resulted in 1,700 user-generated images in one week; in one month, Instagram had 6,368 Cloud Paint images.

In a podcast interview, Weiss said that Instagram "has been an incredible tool to show a lot of user-generated content."

Between 2016 and 2018, Glossier raised $76 million in two rounds of funding and opened two stores: a showroom in New York (which transitioned into a permanent flagship store) and a store in Los Angeles, according to Hanbury.

2018 was a particularly big year. The company told Business Insider that it surpassed $100 million in annual revenue, doubling its 2017 numbers; acquired a million new customers; sold one Boy Brow (one of its most popular products) every 32 seconds. The same year, Glossier was valued at $390 million in funding, reported Katie Roof and Yuliyaf for The Wall Street Journal.

In 2019, Glossier launched a new color makeup brand, Glossier Play. It also opened new pop-up locations, including seven inside Nordstrom department stores around the US.

Rent the Runway, which allows women to rent high-end clothing, has made rental fashion mainstream, according to Mara Leighton for Insider Picks. "This is a fundamental evolution in consumer behavior and we expect it will have an impact in the fashion business in the years ahead," Business of Fashion wrote in its State of Fashion report for 2019.

CNBC named Rent the Runway the ninth most disruptive company in the world, right alongside Uber, Airbnb, and SpaceX.

Hyman originally dreamed of being on stage when she was younger, she told Samantha Sutton of Coveteur. But during college, Hyman became passionate about income inequality, urban poverty, and race relations, so she focused on issues related to public policy and the media, she wrote in an essay for Cosmopolitan.

For the next five years, Hyman worked at Starwood Hotels and Resorts, where she began a honeymoon registry; WeddingChannel, her "first hardcore sales role"; and talent and modeling agency IMG, where she was the director of business development.

In 2007, she went back to Harvard for her MBA without a plan, she wrote in her essay. Her sister told her to look up a friend of a friend: Jennifer Fleiss, who happened to be the first person she met by coincidence.

Looking back, Hyman said she wishes she took a few years off after college to travel the world and learn different languages, she told Chanelle Bessette of Fortune in 2014. "I think that once you hop on the career train, it's hard to hop off of it," she said.

Fleiss studied political science at Yale. Post-college, she did strategic planning for Morgan Stanley and Lehman Brothers and founded Carter Admissions, an online college essay editing service, before enrolling in Harvard Business School in 2007.

In an interview with Bethany Biron for Glossy, Fleiss said it was a difficult decision to leave Rent the Runway but that she missed the start-up world. The early stages of businesses, she told Gabriela Barkho of Observer, is where she's her "best self" and has "the most value." She remains a board member and advisor of the company.

Fleiss started Jetblack with Jet founder and CEO Marc Lore, a longtime mentor who reached out to her with the idea, according to Barkho. But Rent the Runway and Jetblack have something in common: "They're both tools that enable women to save time and hopefully be successful at home and at work, if they chose to do that," Fleiss told Barkho.

According to Anne Stych for Biz Women, Fleiss was replaced as Jetblack's CEO in October and stayed on as an advisor, spokesperson, and ambassador.

Hyman cold emailed Diane von Furstenberg and the CEO of Bergdorf Goodman, who respectively gave them insight on how Rent the Runway could attract younger generations to designer brands and fill a hole in the fashion industry, Hyman wrote in her essay.

Hyman and Fleiss didn't start with a business plan — they began by buying dresses at retail in their own size and visiting college campuses to rent them to women, Fleiss told Adrian Granzella Larssen of The Muse. They also interviewed around 1,000 women about the idea, according to Hyman.

They then pitched VCs to acquire funding and sign on designers, which proved challenging, Hyman wrote. This was all while they were still in school.

Hyman and Fleiss rented space from an architecture firm in New York with four full-time employees, 12 interns, and a local dry cleaner as a storage space, Hyman wrote in her essay. They also leveraged media contacts to land a New York Times story on launch day, which helped them sign up 100,000 members in the first week; this number climbed to 1 million within a year.

"Rent the Runway has never spent money [to advertise] our business," Hyman wrote. "It has grown entirely by word of mouth."

Today, Rent the Runway operates out of its 40,000-square-foot Manhattan headquarters. The company has launched three different services, from one-time rentals to unlimited rentals for $159 a month. In the past five years, it's launched five brick-and-mortar stores from New York City to San Francisco.

Sapna Maheshwari of The New York Times was the first to report on the funding round, which was led by Franklin Templeton Investments and Bain Capital Ventures. The year prior, Jack Ma and Joe Tsai of Alibaba reportedly invested $20 million in Rent the Runway through their asset management firm, Blue Pool Capital.

Rent the Runway plans to use the funding to expand into more product categories and open a second distribution warehouse in Dallas and an 8,000-square-foot store in San Francisco, according to Maheshwari. It recently partnered with West Elm to offer customers the chance to rent pillows, duvets, and throws.

"Our goal is really to create the Amazon Prime of rental," Hyman told Maheshwari.

In 2015, Fortune's Daniel Roberts took a deep dive into why seven executive level employees left Rent the Runway within a year. Former employees told him, "It felt like high school, it was very clique-y," that the "culture is unpredictable and erratic," and that there were "frequent screaming matches" in the office between top executives.

Hyman told Roberts that the changes are part of startup life. "There is an openness," she said of the office. "People feel extremely comfortable with me personally. I have office hours where they can come talk to me."

And in fall of 2019, the company announced it won't accept any new subscribers or one-off rental orders until October 15 following customer complaints over delayed orders, reported Hanbury. Hyman told Kim Bhasin of Bloomberg these delays resulted from a "significant" operational shift at the company, which involved changes in its supply chain.

"We are sorry, and we own this," Hyman wrote in an email sent out to customers and obtained by Business Insider's Áine Cain. "Everything we are doing today is to improve your Rent the Runway membership for the long-term."

Hyman told Bhasin that roughly 14% of Rent the Runway's subscriber base was impacted by the problems. The company could lose $2.7 million due to canceled subscriptions, according to web and mobile software expert Bob Buffone, reported Business Insider's Kate Taylor.

Fleiss and Hyman, who both live in New York with their families, each own 13% stakes in Rent the Runway, landing the two on Forbes' Richest Self-Made Women To Watch list in 2016, with estimated fortunes of $80 million each, according to Clare O'Connor of Forbes.

Hyman also serves on the Board of Directors of The Estée Lauder Companies, on the Women, NYC Advisory Board and is a Founding Member of the NYSE Board Advisory Council. Fleiss is an adviser to the Skimm and works with a career coach, she told The Cut.

Hyman told CNN she gets around eight hours of sleep, "but I tend to wake up several times a night with constant dreams, thoughts, and ideas related to Rent the Runway."

"Every night I have a ritual before I go to sleep where I read for at least half an hour because it's the only thing that will help me get my mind off of Rent the Runway," she told Fortune. Her goals, she added, are to inspire more women to become entrepreneurs and to start an urban commune in New York City to live among her friends and family after Rent the Runway.

Casper aimed to disrupt the mattress industry based on a simple idea: making buying a mattress an easy, pain-free process. Shipped in a three-and-a-half foot tall box, Casper's high-quality foam mattresses range from $395 for an essential twin to $2,695 for a California King advanced mattress, and all come with free 100-day trials.

"Casper aims to give customers a better sleep, not a place to sleep," wrote Erin Griffith for Fortune. "It launched itself as 'the Warby Parker of mattresses.'"

The brand has become known for its social media presence, reported Tom Huddleston Jr. for CNBC Make It: Celebrities like Kylie Jenner and YouTube influencers have all flaunted the brand on their channels.

"I was the nerdy kid reading the Wall Street Journal in middle school," Krim, born to an entrepreneur dad, told Griffith. He studied marketing at the University of Texas at Austin, where he taught himself HTML and built e-commerce websites for manufacturers, from sports tickets to mattresses, Griffith wrote.

Krim previously founded The Merrick Group, an e-commerce company, and VocalizeMovile, a mobile tech and advertising company. Griffith described him as "straitlaced" and "levelheaded."

In 2013, Krim realized that the mattress industry hadn't evolved in the past decade and was only dominated by two companies and made a plan with the other four cofounders to eliminate the overhead of stores and salespeople by selling foam mattresses in a box online, Griffith reported.

Chapin wanted to be a scientist growing up and enrolled at Princeton University to study chemical engineering — but a class on structural art inspired him to study civil engineering structures instead, he told Lindsay Friedman of Entrepreneur. In 2000, he went to Stanford University to receive his master's in product design. Here, he had his first business idea, he told Friedman: Furance Surf, a dry glove for surfing.

He worked at IDEO for 10 years, which he called his "most influential job," before founding CommonMade, a design consulting firm. In 2009, Chapin worked with a non-profit on rural sanitation project in Cambodia for six months. "I'm inspired by good citizens — people who contribute to their communities," he told Friedman.

He spotted a trend in wellness and thought there was an opportunity for a company that focused on sleep for overall wellness, Chapin previously said. He told Elizabeth Segran of Fast Company that Casper's products are developed using scientific processes.

He told Friedman he likes working, ignores emails to stay productive, and uses sticky notes to make daily to-do lists. Chapin is the only 40-something on this list.

Parikh was previously Casper's COO. According to Fast Company, he co-authored three NASA patents during his year there working on robotics and co-founded WaterWalla, which gives clean water access to underdeveloped urban communities.

Parikh is well-suited for his position. His father is a sleep doctor. Parikh himself centers his routine around sleep, according to Cameron Albert-Deitch of Inc.: "If he has an 8 a.m. meeting the next day, he'll subtract nine hours — eight for sleeping and one for getting ready in the morning — to determine an 11 P.M. bedtime," Albert-Deitch wrote.

But in Casper's early days, he worked 80 to 100 hours per week, Parikh told Albert-Deitch.

Krim told Riley de Leon of CNBC that of all the founders, Parikh has been the most progressive toward the emerging health trends they've studied. This led to Casper developing its own version of CBD-infused gummies in September 2019.

He spends seven hours a day in meetings and tries to answer all emails, he told Anna Hensel of Inc. His smartphone also helps him stay productive, and he usually works on Casper projects from 8 a.m. to 7:30 p.m. on the weekdays but will occasionally tackle longer projects on the weekends, according to Albert-Deitch.

"Year Two, I would have said, Casper, Casper, Casper," Sherwin told him. "Now, it's like, bicycle, coffee, Casper, Casper, read, eat, sleep."

In 2017, Sherwin co-founded Block Renovation, a start-up that offers quick and affordable bathroom renovations in New York and New Jersey with a just a few online clicks.

Sherwin's father developed brownstones in New York in the 1980s, he told Konrad Putzier of The Real Deal. "I grew up around the opaque, black box of construction and also the subculture of it, and always found it really interesting," he said.

Flateman studied music composition and literary theory at Brown. He's a composer and musician who has performed at Carnegie Hall. Before Casper, he implemented a data visualization project with the Library of Congress.

When working with Casper's cofounders, he told Jon Fine of Inc, "It works for us because we have disparate skill sets, and we are focused on and have domain over different areas. It's not as if we are five MBAs with the same skill sets and the same desired job. We debate, collaborate, and challenge one another's ideas endlessly."

Flateman has previously said his life motto is: "If at first you don't succeed, take a nap and try again."

There is not much known about A New Company yet, but the CEO's LinkedIn reads: "We are keeping a low profile (and avoiding lawsuits) while we are developing a great new platform."

"From this mix of talents Casper was born, combining Krim's sleep-industry savvy, Chapin's design chops, and the Brown trio's skill in creating smooth online user experiences," wrote Ilan Mochari for Inc. The "Brown trio" was also rooming together in Brooklyn at the time with a man named Kasper, who was often tired and slept with his feet hanging off the bed, wrote Diana Pearl for Adweek.

The cofounders initially struggled for investments and used their own cash and credit cards to fund Casper. "We put, like $50,000 to $100,000 on our credit cards, which probably was irresponsible," Parikh told Huddleston. "But we were all in."

They finally received $1.85 million in funding in January 2014 and lined up a bit of press in advance, according to Huddleston's and Griffith's separate reporting. The first day the site went live, they sold out of mattresses; just two months later, they sold what they had hoped to sell in a year: $1.8 million worth of mattresses, according to Huddleston.

After its initial success, Casper quickly attracted celebrity investors like Leonardo DiCaprio, Ashton Kutcher, and 50 Cent, Huddleston wrote.

In 2018, Casper exceeded $400 million in annual revenue, reported Selina Wang for Bloomberg. With its latest funding, Casper has raised a total of $340 million, she wrote. It plans to put the money toward expanding its international physical retail store presence.

"Normally you open a store, have to build presence, then the store loses money and eventually pays back after many years," Krim told Wang. "We have such a productive digital business that we're profitable on day one of opening a store."

Casper wasn't the first to invent the concept, Chapin told Paul Farley of Furniture News, but they were "the first to put the effort into building a phenomenal customer relationship and a brand around sleep."

As Griffith puts it, "Thanks to a mountain of positive press, an estimated $80 million annual marketing budget, savvy social media magic and — oh, right — a product that people seem to really like, America's urban-dwelling, podcast-listening millennial professionals like me are hyperaware of the company."

Rubio and Korey's goal was to sell stylish luggage at a more affordable price than competitors such as Tumi, reported Amy Feldman for Forbes. Their first product: A four-roller hard-shell carry-on bag listed at $225 that included a battery to charge mobile devices.

An online sales strategy involving 1,000 Instagram influencers helped fuel Away's initial success, Feldman wrote. Away's products have been touted as "Instagram worthy" and backed by models including Karlie Kloss, reported Meira Gebel for Business Insider.

Rubio previously intended to become a lawyer but studied supply-chain management instead at Penn State, working for Johnson & Johnson's Neutrogena division through her college's co-op program at age 20, according to Feldman.

After her manager told her she'd need an MBA to join the marketing department, Rubio left school and began working as a social media consultant in LA for food trucks, small businesses, and movies, Rubio told Fortune. She eventually landed a job at a digital agency in New York, working with clients like Ford, Disney, and Estée Lauder, Feldman wrote.

In 2011, she ended up a social media manager at Warby Parker, where she met Korey. "My career has been so weird and nonlinear," Rubio told Christine Lagorio-Chafkin of Inc. "So many times, I was so uncertain."

Korey was born to Romanian and Lebanese parents and traveled the world growing up, according to Fortune. Like Rubio, she originally had other career goals. Korey studied international relations at Brown hoping to work in nonprofits, Feldman wrote, but ended up in retail instead.

One of her first jobs, Korey told Fortune, was as part of an executive development program at Bloomingdale's, where she learned everything from retail markups and wholesaling to licensing and department store supply chain — "the very things we would avoid at Warby Parker and Away," she said.

From there, she went on to become an assistant buyer at Kate Spade and head of supply chain at Warby Parker in 2011, where she met Rubio.

Rubio moved to London to work for fashion retailer AllSaints in 2013, while Korey left in 2014 to get her MBA at Columbia, Feldman wrote. At the time, Korey was also consulting for Casper. "Working for two direct-to-consumer start-ups that are now both valued at over a billion dollars gave me a lot of insight into what it takes to build a rapidly growing business," she told Harper's Bazaar.

Rubio, who has traveled to more than 50 countries, came up with the idea for Away after her old suitcase broke in the airport, according to Feldman. "I started thinking, 'How do we do what Warby Parker did for glasses?'" she told Feldman. "How do we take something really simple, and make people care about it?"

They raised money from friends and family, followed by a VC round, and ended up raising double their goal, Rubio told Bond Street. They found a factory in China to make a few thousand suitcases, according to Feldman, and the first carry-ons were delivered in early 2016.

Both Rubio and Korey have received numerous recognitions. They secured a spot on Forbes 30 Under 30, and Away landed a spot in Forbes' 2018 Next Billion-Dollar Startups.

Away's success, according to Feldman, largely relies on two things: The bulk of its volume is online, meaning they don't have to share revenue with high-overhead department stores, and it focuses on its brand rather than technology.

"When I look back on the early days, I think what fueled our passion and kept us going was the belief in what we were creating and how much potential we saw to transform the travel experience," Rubio previously told Business Insider's Megan Hernbroth in May 2019. "We started with luggage, but our sights have always been set on much more. As the business scales, so will our ambitions."

The investment was first reported on by Katie Roof for The Wall Street Journal. It's the fifth women-led company to become a unicorn in 2019, Hernbroth wrote.

The new injection of cash will allow the company to expand beyond suitcases into a larger "travel brand," Rubio told Hernbroth. The company is exploring new products in the apparel, wellness, and accessories spaces to simplify the travel experience.

"We're excited to figure out how else we can play a role in travelers' journeys, not just focusing on what you use to pack, but also what you might need to bring with you — this might include things like skincare and supplements, or thoughtful apparel for more comfortable travel," Rubio said.

Reporter Zoe Schiffer of The Verge spoke with 14 former employees, who said they were criticized by executives on company-wide Slack channels and pressured to work around the clock. Korey reportedly called one one staff member "brain dead."

An Away spokesperson emailed a statement from Korey to Business Insider's Shana Lebowitz, in which she apologized for messages she sent employees and said Away has been working to create a positive company culture:

"I can imagine how people felt reading those messages from the past, because I was appalled to read them myself. I am sincerely sorry for what I said and how I said it. It was wrong, plain and simple," the statement read, in part.

Read the full message here.

Korey resigned as CEO shortly after the investigation, assuming the role of executive chairman. She will be replaced by Lululemon executive Stuart Haselden on January 13.