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The Unique Challenges Of Being A Middle-Aged Woman Entrepreneur

From questions about their family duties to disbelief in their market potential, these women are battling Silicon Valley’s misconceptions.

The Unique Challenges Of Being A Middle-Aged Woman Entrepreneur
[Photo: Hero Images via Getty Images]

In today’s entrepreneurship model, women who start companies in their forties to fifties are a fast-growing group. And this invites a whole new set of challenges, because most people still think successful companies are started by men in their twenties.

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“The people building companies now are not just the 25-year-old male engineers,” says Trish Costello, CEO and founder of Portfolia. “[That idea] has never really been realistic, but it’s certainly not the case now, with so many people starting their businesses at an older age.”

“What happens with women is that we have kids and have much more complex lives when we’re younger,” Costello tells Fast Company. “Once our kids get a little older, we have all this creative energy that we put toward creating really great companies.”

According to a Kauffman Foundation report published last year, people aged 45 to 54 started more companies than any other age bracket. In 2013, 30% of new entrepreneurs were in this age bracket, up from 25.2% in 2003. On the other hand, people aged 20 to 34 started the least number of companies in 2013, at 22.7%, down from 26.4% in 2003.

As more women start companies later in their careers, they find themselves facing unique challenges that deal not only with sexism, but also ageism. Below, Cynthia Schames, founder of AbbeyPost, Sara Schaer, founder of KangaDo, and Anna Zornosa, founder of Ruby Ribbon, share how to overcome the unique challenges of being an older woman entrepreneur and blowing expectations out of the water in their second act.

You’re up against extremely overconfident twentysomethings.

Pattern recognition among investors in Silicon Valley is a very real thing, and if you don’t fit the mold, it often works against you.

“Twentysomething-year-old men have a completely different style of pitching [compared to older women entrepreneurs], where they don’t necessarily know the answers to all the questions but they’re so brash about it, they’re extremely convincing,” says Schaer, who started KangaDo, an app that enables busy parents and their friends to help each other get more done, in her forties. “You need to know this is what you’re up against, so target the right investors and make sure you’re not underconfident, because you have to compensate for being an older woman founder.”

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You’ll be in a lot of situations in which you feel like an outsider.

“It’s weird to go to a meetup and literally be the oldest person in the room,” says Schames, who started AbbeyPost, an Etsy-like company for plus-size clothing, in her early forties last year. “If you sit there and dwell on it, you feel like a total outsider. You feel like, What the hell am I doing here?”

“I’ve been in the tech industry since 1994, so I already knew that I was going to be surrounded by young people,” she continues. “I’m cool with that. But that’s because that’s my individual personality, I’m cool. I’m not a soccer mom. I’m certainly not wearing mom jeans. I don’t let it intimidate me at all.”

One of Schames’s tactics in these situations is to remember that age can work to your advantage because you have experience that the smartest twentysomething-year-olds don’t have.

“Fortysomething women have a ton of juggling abilities, and I think that that makes us essentially the best entrepreneurs,” she says.

You’ll get asked uncomfortable questions.

Both Schames and Schaer have been asked questions about their family life that young male (or female) entrepreneurs probably wouldn’t get asked.

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The first time Schames was asked by an investor how she was going to run a company and have kids at the same time, she was so shocked she didn’t have an answer. The second time it happened, she was prepared and asked the investor how he did it, but Schames recalls this wasn’t the best response.

During these situations, Schaer advises not letting it ruin your day or your conversation.

“This conversation wouldn’t come up in my twenties because I wouldn’t have had kids yet,” she says. “Luckily, no one has made comments about my gender.”

You’ll need to prove a good track record.

There’s a great deal of unconscious bias happening, says Schames, and most male investors can’t identify with the problems older women are trying to solve.

“I’ve actually had an investor say to me plus-sized people don’t have money,” she admits.

Since older women entrepreneurs may find it challenging to connect with male investors, it’s important to already have traction in your own company before pitching for funds, advises Zornosa, who left her corporate job to start Ruby Ribbon in 2011, at the age of 52.

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“In my twenties and thirties, I would not have had the confidence that I do now to create a thriving company,” she tells Fast Company. “When making the decision [to start a company] when you’ve already had a successful career, your eyes are wide open. I knew that doing a startup would be akin to having another baby.” Today, Zornosa has 800 women selling her products in stores, salons, and even in their living rooms.

Once, when Costello asked a contact for an introduction to a well-known, aggressive angel investor, her contact told her it wouldn’t be worth it because the investor is only looking for “the really sexy opportunities.”

“The problem is, the 25-year-old guy is not the main consumer. . . . He’s not even close to being a major consumer in the U.S. unless you’re looking at video games and large-screen TVs,” says Costello, who started Portfolia in her fifties. “Major consumers in the U.S. are women by 85% of all consumer products and they actually buy the majority of enterprise products as well.”

The best investors are the ones who can recognize great companies created by women based on their experiences as main consumers. They also recognize that women who start businesses later in life are proving that entrepreneurial success doesn’t happen only in youth and it certainly doesn’t happen only to twentysomething-year-old males.

“Every time I run into a brick wall, I figure out a way to either climb it, go under it, or smash through it,” says Schames. “Brute force is what I would recommend to any female entrepreneur, especially if they’re starting a company later in life.”

About the author

Vivian Giang is a business writer of gender conversations, leadership, entrepreneurship, workplace psychology, and whatever else she finds interesting related to work and play. You can find her on Twitter at @vivian_giang.

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