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Advice / Succeeding at Work / Getting Ahead

5 Challenges of Being a Female Entrepreneur—and How to Overcome Them, From Women Who Have Succeeded

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Over the last few years, women have become more entrepreneurial than ever before. The global rate of female entrepreneurship has been increasing faster than that of male counterparts, and American women started an average of 1,817 new businesses per day between 2018 and 2019.

Still, women who own businesses undeniably face unique challenges that men don’t, from having a harder time fundraising to mastering work-life balance. That was the case for Sana Javeri Kadri. After moving from India to the United States, Javeri Kadri noticed that the spice trade system in the U.S. was outdated. In 2017, she responded by founding Diaspora Co., a line of spices made by local farmers in India; she also works closely with the Indian Council of Agricultural Research to support the country’s innovations in regenerative and sustainable agriculture.

Despite all her achievements, Javeri Kadri still had a difficult time running and scaling her company. “I have more experience than most of my male counterparts, and yet have to push twice as hard to be considered an expert,” she says. “I’ve lied about my age, my marital status, and my sexuality to gain access to certain tables.”

But just because women face extra challenges as entrepreneurs, it doesn’t mean success is out of reach. Here, four business owners share the hurdles they’ve faced and how they overcame them—and how you can, too.

Challenge #1: Getting People to Take You—and Your Business—Seriously

Between 2014 and 2019, the number of women-owned businesses increased 21% (compared to 9% for all businesses). Yet despite these growing numbers, many female entrepreneurs are faced with skepticism from investors, potential partners, prospective customers, or even their personal network. Lauren Bates, the founder of Wild Terrains—a travel company that plans small group trips for women, with itineraries supporting woman-owned hotels, restaurants, and other businesses—has experienced this first-hand. “When I tell most men what I do, they don’t get it,” she says. “They don’t see why there would be a need for it.”

The Solution

Establishing a strong digital presence is key. For Bates, her Squarespace website is responsible for about 95% of her bookings. And it ended up serving a bigger purpose when the pandemic hit and travel came to a halt. She added a section for virtual gatherings, working with her partners in Mexico City and Portugal to offer classes in cooking, photography, embroidery, and more.

“I think there were a lot of women who were really going through a lot of hard stuff and being able to take an hour and have a cooking class for $10 was a really nice escape for them at the moment,” Bates says.

screenshot of Wild Terrains website
Wild Terrains' website, which founder Lauren Bates built on Squarespace.
| Courtesy of Wild Terrains

Creating a website was the first thing that Kellie Wagner did when launching Collective, a consulting firm that offers diversity, equity, and inclusion training. “I’d built a few Squarespace sites for friends and other entrepreneurs, and I loved doing it, so it was a no-brainer for me as a place to start,” she says. “Having a clear and beautiful web presence immediately created a sense of credibility, but also allowed people to connect on a more emotional, personal level with Collective.”

Gabriel Blitz Rosen also turned to Squarespace when she founded Townhouse Digital, an editorial and social media content studio. “I felt like a website was so important, but I didn’t have the money back then to hire someone,” she says. “Squarespace had easy-to-use templates, and just made it so simple to create a website by myself. It had a polished editorial feel, and it showed potential clients what we can do through content.”

Pull quote: "Having a dialed-in website and an Instagram community are the reasons we're still here and growing."

And instead of relying on conventional ways to sell her product, Javeri Kadri created an easy-to-use website and focused on Diaspora Co.’s Instagram page, which currently has more than 50,000 followers. “Having a dialed-in website and an Instagram community are the reasons we’re still here and growing,” she says.

Challenge #2: Feeling the Need to Be Perfect

Women are more likely to exhibit perfectionist traits than men, so it makes sense that many female entrepreneurs apply that thinking to their businesses. But while it’s important to proofread your website and make sure the numbers add up on your profit and loss statement, Bates believes striving for total perfection can stifle productivity.

The Solution

Instead of waiting for every single piece of your business to fall into place just so, Bates encourages female entrepreneurs to prioritize progress over perfection. “You need to put something out into the universe, get feedback, and keep moving with it,” she says. “Wild Terrains looks really different now from when I first launched it. Half of the battle is committing to something and just doing it.”

Challenge #3: Being Labeled as Too Emotional

A common stereotype about women is that they are too emotional—and this preconception often follows female entrepreneurs into board rooms. The label can play out differently depending on the situation. Male investors, for example, may perceive women as not steady enough to lead a business to success. And male employees may prefer a female boss to lead in a tough, no-nonsense style (in other words, like a stereotypical man).

screenshot of Diaspora Co. website
Diaspora Co.'s website.
| Courtesy of Diaspora Co.

“Vulnerability, transparency, compassion, and accountability are my pillars of good leadership, and all four are traits often brushed aside as ‘soft’ or ‘weak’ by the male-dominated business world,” says Javeri Kadri.

The Solution

Rather than stifle or hide your emotions, embrace them. That’s exactly what Javeri Kadri has done—and it’s worked. “My emotional, vulnerable leadership allows me to form community and relationships with customers and vendors—and in the long term, that’s as powerful as it is profitable,” she says.

Pull quote: "If that's 'emotional' or seen as being too feminine, I'm okay with that because it's the exact emotion that gets the best out of my team."

Wagner has used the same approach at Collective, which has laid the groundwork for a positive, trusting company culture. “I regularly hear feedback that my vulnerability allows my team to feel like they can be human, too,” she says. “It makes them show up in a different way because they know I care about each of them as full people, not just worker bees I pay to show up. If that’s ‘emotional’ or seen as being too feminine, I’m okay with that, because it’s the exact emotion that gets the best out of my team.”

Challenge #4: Finding the Right Investors

Raising funds is an exciting but intimidating process for most small businesses. And it can be especially daunting for women since the majority of venture capital firms are run by men. “It has definitely not been easy,” says Wagner of her experience trying to fundraise. “Not only am I female, but I’m a Black woman without any fancy Ivy League degree or impressive accolades to lean on. I don’t think that a lot of people are willing to take chances on people like me.”

screenshot of Collective's website
Collective's website, which founder Kellie Wagner built on Squarespace.
| Courtesy of Collective

She continues, “I think that one of the biggest challenges in the startup space especially when it comes to getting investors is that the industry relies on pattern-matching to deem investments risky or safe. Because men, especially white men, have had more chances to prove themselves and therefore more chances to succeed, they seem less risky of an investment, even though I’d argue that investing in Black women, many of whom have had to be more resilient and more resourceful than your typical entrepreneur, is actually a pretty solid bet.”

The Solution

When it’s harder to find investors willing to take a chance on you, it can be tempting to jump at the first offer. However, it’s important to make sure they believe in you and your vision for the business. Because if they don’t, you may end up in a situation where “there are expectations about how fast you need to grow, and having to make compromises on quality or brand values along the way to get there,” Bates says.

Pull quote: "You could also focus on finding female-run VC partners—especially since studies have shown that they invest in two times more female founding teams at the early stages than male-run VCs."

You could also focus on finding female-run VC partners—especially since studies have shown that they invest in two times more female founding teams at the early stages than male-run VCs.

And there’s always the chance that your patience in getting investors will pay off in another way: You might realize you don’t even need the capital. Wagner and her team have grown Collective’s revenue 10 times since its first year—without any outside investment. “Not only are we profitable, but I continue to own the entire company as the sole founder,” she says.

Challenge #5: Valuing Your Work Correctly

Women have historically been paid less than men; according to the 2018 Census, they earned 82 cents for every $1 earned by men of all races (a gap that grows even more for women of color). And when you’re so used to being undervalued, you may not even realize that you’re undervaluing yourself—which is what happened to Blitz Rosen.

screenshot of Townhouse Digital's website
Townhouse Digital's website, which founder Gabrielle Blitz Rosen built on Squarespace.
| Courtesy of Townhouse Digital

“When I first started Townhouse, I bent on certain prices because I had imposter syndrome. I didn’t think I should actually charge high prices,” Blitz Rosen says. “As we grew, I had a friend who I was working with say, ‘Are you insane? You should be charging double.’ And when COVID-19 hit, I had several male clients ask me to knock the prices in half because they were two or three months late in paying me. I felt like they just expected me to buckle.”

The Solution

The key is learning not to shortchange yourself, and to value yourself appropriately. Research the market, and figure out what other companies are charging for a similar service or product. You could also join a networking group for business-owning women, which can provide a wealth of knowledge. For example, Blitz Rosen—who has two young children—has found a lot of support through Hey Mama, a community for working moms. “I can go to this network and ask any question I have,” she says. (Bonus: She also finds clients through it.)

At the end of the day, you just have to remember that you are worth every penny that a male counterpart is worth. And getting paid the rates you deserve could be the difference between your company succeeding or not.