Female Founders 100: Serial Entrepreneurs We all know, to be an entrepreneur requires a little bit of crazy. To be a serial entrepreneur is to pair that with the hunger to jump on the next big idea, this time armed with the wisdom of experience. These women are building their second (or third or fourth) company, and it likely won't be their last.
To hear Sharkey tell it, the $240 million in venture capital she raised this summer pretty much just fell into her lap: "A couple of VCs who were friends said, 'I hear you guys are up to something--can we come visit?' " The something--trying to challenge every retailer from Target to Whole Foods with Brandless's own line of consumer staples, like blueberry flax granola or a 6.5-inch Nakiri knife, all for $3 a pop--is as ambitious as it is audacious. This is hardly Sharkey's first time around the block. The Mill Valley, California, resident co-founded iVillage, and then sold it to NBC Universal for $600 million in 2006. With SoftBank behind her and a Brandless outpost on Target's home turf of Minneapolis, run by the retailer's former VP of merchandising, Sharkey's gambit will be either spectacularly disastrous or gloriously disruptive. --Kimberly Weisul
Create & Cultivate
When Johnson's marketing agency threw its first major event in 2015, she faced a choice: "We could do this for cheap in a hotel conference room, or we could make it beautiful and amazing ... and Instagrammable." She aimed for the 'Gram--and attendees loved the affair. So did the sponsor, eager to reach ambitious young women, both in person and on social media. So Johnson sold her agency, and today her $10 million events business--which hosts up to 40 events annually--creates sponsored experiences meant to be both inspiring and shareable. --Burt Helm
Some entrepreneurs will tell you that building their company was so hard they could never do it again. Not Kilgore. She launched her latest beauty venture a year and a half ago, but started her entrepreneurial career in the 1990s, with the spa chain Bliss. After selling a $30 million chunk of it to LVMH in 1999, she started Soap and Glory, which sold for a reported $50 million. FitFlop soon followed. Now, Kilgore is taking on the direct-to-consumer trend in an industry that has plenty of margin to play with. "The retailer takes 60 percent right off the bat," she says. "People don't know that if a factory makes a lipstick, that lipstick is available to any other brand that works with that factory." The common thread through all of Kilgore's businesses: Every one has been entirely self-funded. --K.W.
Serial entrepreneur Naficy founded Minted in 2007, betting that the best way to expose original designs from indie artists was through crowdsourcing. Little did she realize that she'd spend a decade building a lust-worthy data engine. Every week, Minted gets thousands of designs; to date, millions of consumers have voted on them. "We use that data to predict what's going to sell," says Naficy, who founded her first company, online beauty store Eve.com, in the late 1990s. Now retailers such as West Elm and Target are partnering with the online design retailer to create an endless torrent of co-branded products based on 250,000 licensable designs from the Minted archive. These new partnerships are so lucrative, says Naficy, they're now the fastest-growing part of her already profitable business. "It's changing the company radically, and in a few years it will be 50 percent of our revenue." --Tom Foster
The serial entrepreneur and CEO of the warehouse-robot maker has spent her career building better, smarter automatons. A trained mechanical engineer who's regularly hailed as a leading visionary, Wise was an early employee at prominent (now-defunct) robotics accelerator Willow Garage and co-founded Unbounded Robotics before Fetch's founders tapped her to lead their just-launched company. Since 2014, Wise has raised $48 million for Fetch and lined up more than 50 big customers, including Inditex (Zara's parent company) and DHL, which use Fetch's cloud-based software and warehouse hardware to analyze data as well as to sort and ship goods. Now Wise is hard at work on developing a robot with an arm--a component of "the holy grail of robotics in general," as she puts it. --Maria Aspan
Tina Roth Eisenberg
CreativeMornings, Tattly, TeuxDeux, CreativeGuild
Don't complain--create. That's the philosophy of the Swiss-born designer who has made a career out of turning side projects into businesses. In 2008, disillusioned by big, expensive industry conferences, she launched CreativeMornings, a monthly speaker series that has grown to 188 cities around the world. A slew of fussy to-do apps led Roth Eisenberg in 2009 to build TeuxDeux, a more bare-bones, intuitive option. Aesthetic dismay with the temporary tattoos her daughter brought home in a goodie bag prompted her, in 2011, to create Tattly, now a thriving brand of artist-rendered temporary tats for kids and adults. Then earlier this year, she launched her most ambitious venture yet: CreativeGuild, a "LinkedIn for creative people." More than 300,000 creatives, ranging from illustrators to Dropbox product designers, signed on, along with 440 companies. "When people ask me how I come up with startup ideas, I tell them, 'Don't think of it as a financial endeavor, approach it as a labor of love,' " says Roth Eisenberg, "because when you're worrying about money, people can feel it." --Kate Rockwood
Electric cars and energy-efficient power grids need better batteries--and the Swedish-born serial entrepreneur and PhD has spent her career inventing them. She has founded two battery startups: Boston-Power, which makes lithium-ion batteries; and, in 2012, Cadenza Innovation, which is focused on creating better and more energy-efficient packaging for battery power cells. Her new company has raised over $10 million from angel investors, and lined up $6 million in grants from the U.S. Department of Energy and three states. This year, New York's state government agreed to use Cadenza technology to test a clean-energy project: "The energy problem is a global problem--but we're not approaching it as a global problem," says Lampe-Onnerud. "It becomes a local opportunity." --M.A.
As president and CTO of SurveyMonkey, Tobaccowala was among the many people devastated when Dave Goldberg, the company's 47-year-old CEO (and Sheryl Sandberg's husband), died unexpectedly in 2015. For Tobaccowala, Goldberg's death, attributed to heart disease, wasn't just a loss; it was a wake-up call. So she started Gixo, an app that lets users take live-streamed or on-demand fitness classes via their smartphones, a populist alternative to the wave of expensive boutique fitness chains like SoulCycle. "Everyday Americans were getting left out of this health and wellness boom," says Tobaccowala, who previously co-founded Evite. --Jeff Bercovici
CBD for Life
"I wanted to make something more appealing to the mainstream with a Chanel look over a bohemian feel," says Stavola. She's not talking about perfume, but beauty products infused with CBD--cannabidiol, a non-psychoactive compound in marijuana associated with pain relief and anti-inflammation. So three years ago, the former Wall Street executive from New Jersey decided to start CBD for Life (along with her sister), now her third cannabis venture. Her first, a dispensary chain in Arizona, was later sold to a Canadian public company for $25 million (where Stavola is now its COO), followed by Melting Point Extracts, a THC concentrate manufacturing company. Stavola says she sees a lot of parallels between cannabis and internet deals in the late 1990s. "During the early days, institutional investors were not interested in cannabis, and it was only hedge funds and aggressive investors getting in," says Stavola. "Today, Constellation, which makes Corona beer, is in the [CBD] space." --Will Yakowicz
The internet is overwhelmed with websites and forums for mothers, yet mom-shaming--calling out moms for parenting choices, with the implication that they are lousy parents--persists. "Women go into battle when they go on these platforms," says Lacy. "They are not a place where you can be vulnerable." So she's building a community site without upvoting or threaded conversations, both of which she says lead to nastiness. Her San Francisco-based site, Chairman Mom, encourages discussion not just about child care, but also about work, friendship, relationships, money, even divorce. And people are willing to pay a $5-per-month subscription fee to have that safe space. Says Lacy, also the founder of technology media company PandoMedia: "We don't have trolls or bots, because no one is going to pay $5 a month to abuse women when they can do it for free at scale, everywhere else online." --K.W.
Kanter grew Serena & Lily, the airy home retail brand she co-founded in 2004, to more than $50 million in annual revenue, but after over a dozen years as its CEO, she was restless. She'd long dabbled in philanthropy--at one point appearing on the cover of Time magazine next to Bill Gates as the face of the next gen of philanthropists--and then, 18 months after leaving her company, Kanter came across Mixed Bag Designs, a school-fundraising company that hadn't evolved with the times or technology. "I thought, this is a really exciting opportunity to use capitalism as a way to fuel donations for causes," she says. Sites like GoFundMe had proved the power of cause-based crowdfunding, but nobody had married that with the kind of smart and stylish merchandising that Kanter was expert at. She bought Mixed Bag and relaunched it as a new crowdfunding retail brand called Boon Supply. She's able to bypass expensive digital marketing costs because her customers willingly do the marketing for her: People set up a cause, and then invite their friends to shop, with 50 percent of their spend going toward that cause. While her experiment is still early days, Boon Supply has already powered more than $12 million in donations to causes. --T.F.