6 Fearless Female Entrepreneurs Share Their Startup Stories

By Michael M. Clements & Jenn Thorton | October 3, 2018 | People

Women founders dish on making the tough calls—and rising to the occasion.

In startups, the line between success and failure is perilously thin. Sometimes it comes down to one decision—a choice that not only affects an owner’s life but the life of the business and its employees. These are high stakes. For our Innovators and Influencers issue, we head to front lines of leadership to ask women founders to share some of their most harrowing startup moments.

The Pivot

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Powerhouse Maci Peterson is 30 years old and a CEO, but at 27 she was a lot like us—sending a text that she immediately wished to retract. Peterson got the message and co-founded On Second Thought—a delay-recall mechanism for mobile communications platforms that allows users to take back a text. “Running out of money and telling employees that we could not pay them” was a low point for the entrepreneur, but Peterson and her partner’s move to later patent the recall systems to make the technology available to all forms of telecommunications proved a significant pivot. “That was one of the best decisions we’ve made for the company,” says Peterson, who has been named to BBC 100 Women, Inc. magazine’s 30 Under 30 and Washington Business Journal’s 40 Under 40 lists. “We handle adversity by remaining hopeful and persistent.”

The Leap of Faith

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Sarah Jessica Parker, Lena Dunham, Oprah—these are just some of the prolific contributors to the 7 million subscribers of buzzy online newsletter The Daily Skimm, which reports the news but keeps it brief and consumable. Think short, sweet and sassy. Co-founders and co-CEOs Carly Zakin and Danielle Weisberg know how to make headlines—theirs is now the fastest-growing email newsletter on the market and they have spun off an app and a series of product launches that speak to theSkimm’s engaged community of mostly female millennials seeking easy integration of information. “Without a doubt,” they say, “the most terrifying moment of our career was the day we decided to quit our jobs at NBC News and start theSkimm. With two months of savings between the two of us and a gut feeling that we could fi ll a void in the market for millennials, we just went for it.” And is that decision ever paying off —to the tune of $25 million raised since 2012.

The Pitch

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Journalist turned co-founder and CEO Jay Newton-Small is a woman who insists on writing her own narrative. She was inspired to start digital storytelling platform MemoryWell after the experience of moving her father with Alzheimer’s disease into a care facility. There she was asked to complete a long, generic questionnaire about his life. Newton-Small set aside the questionnaire and wrote a shorter, more individualized version of her father’s life story that would become a prototype for the professionally penned profiles of individuals with Alzheimer’s and dementia on her platform. It all really started, though, when Newton-Small faced her fears and pitched her concept at the Mellon Auditorium, where she was one of 1,100 applicants competing for a Creator Award from WeWork. Named a semifinalist, she was then asked to give a final pitch to an audience of 1,500. “Now, keep in mind this was only the third time I’d ever pitched MemoryWell publicly,” she says, noting the business was in its infancy, with one paying client. “Everyone else had metrics and growth rates. I had one minute, and I thought, I’m a storyteller and storytelling is at the heart of what we do.” So she told her own. “It was a gamble,” Newton-Small recalls. “The pitch was a far cry from all the others. But it ended up being the right call. The audience—and judges—loved it. We won $130,000 in cash that night and a year’s free office space—enough to bootstrap our company for the first year.”

The Resilience

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Count on Nicole Gallub—alias DJ Neekola—to find the positive spin. She certainly needed it in 2016, when the founder and CEO of entertainment company Pelonkey came to a crossroads when the technology she had invested in for the company forced her to let go of employees, including her sister. “I thought about closing the company as a whole,” says Gallub of a time she characterizes as “dark days” and “soul searching.” “Then I started realizing I had a lot of other things going for me—I have a successful DJ career, I have experience in cybersecurity, shoot... I can even drop everything and become a Lyft driver if I really wanted to.” Bottom line: “[L]ife goes on, and I had options.” She customized existing thirdparty technology to “create a stable, structured way to become an entertainment production company founded on ethical principles,” she says. “Within less than a month, I was back in the green.” Debts paid, Gallub hired her first employee in 2017 and another two since, sharing an offi ce “full of fluff y pink carpets and neon unicorns.” Now that’s entertainment.

The Scale

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Four posters, four unappealing frames and a cool $1,600 for custom framing, and Susan Tynan had enough. She would no longer purchase anything that needed a frame. Eventually, this idea seemed as crazy as the initial $1,600. So Tynan took matters into her own hands with her own company, Framebridge. Perhaps you’ve seen it in The New York Times? The concept of blending “ecommerce, logistics and an intense focus on the customer experience” for custom framing without breaking the bank might seem completely unrealistic, but not to Tynan. In doing exactly this, the founder and CEO of Framebridge created a good product—and a major production backlog. “Our turnaround time went from [three] days to [three] weeks,” she says. But with the team working day and night, a surge in hiring and communicating with customers, the company overcame an intense time. For Tynan, it’s all about how you choose to frame it. “In the midst of the crisis, we also hired a terrific experienced head of production and began plans for what is now our centralized production facility in Kentucky.” That certainly paints a pretty picture.



Photography by: MACI PETERSON PHOTO BY KEITH MUNYAN; CARLY ZAKIN AND DANIELLE WEISBERG PHOTO BY SHARON SUH; JAY NEWTON-SMALL PHOTO COURTESY OF JAY NEWTON-SMALL; NICOLE GALLUB PHOTO BY JON THORPE; SUSAN TYNAN PHOTO COURTESY OF FRAMEBRIDGE